US Pat. No. 10,968,252

METHODS OF PROCESSING A FLUID INCLUDING A RECOMBINANT THERAPEUTIC PROTEIN AND USE THEREOF

Genzyme Corporation, Cam...

1. A method of processing a fluid comprising a recombinant therapeutic protein, the method comprising:(a) providing a first circuit system comprising (i) a tangential flow filtration (TFF) unit having first and second inlets, and (ii) a first conduit in fluid communication between the first and second inlets of the TFF unit, comprising at least one port for flowing fluid into or out of, or both, of the first circuit system,
wherein the first circuit system is configured such that fluid can be flowed through the first conduit and the TFF unit, and filtrate not comprising the recombinant therapeutic protein can be collected from the TFF unit;
(b) providing a second circuit system comprising (i) a tangential flow virus filtration (TFVF) unit having first and second inlets, and (ii) a second conduit in fluid communication between the first and second inlets of the TFVF unit, comprising at least one port for flowing fluid into or out of, or both, of the second circuit system,
wherein the second circuit system is configured such that fluid can be flowed through the second conduit and the TFVF unit, and filtrate comprising the recombinant therapeutic protein can be collected from the TFVF unit;
(c) continuously flowing a fluid comprising a recombinant therapeutic protein into the first circuit system through one of the at least one port, and discarding filtrate not comprising the recombinant therapeutic protein for a first period of time;
(d) continuously flowing a diafiltration medium into the first circuit system through one of the at least one port, and discarding filtrate not comprising the recombinant therapeutic protein for a second period of time;
(e) collecting a fluid comprising the recombinant therapeutic protein that is present in the first circuit system after the first and second time periods through one of the at least one port; and
(f) flowing the collected fluid of step (e) into the second circuit system using a connecting conduit in fluid communication between a port in the first circuit system and a port in the second circuit system, recirculating retentate in the second circuit system, and collecting filtrate comprising the recombinant therapeutic protein from the TFVF unit for a third period of time,
wherein rate of recirculating the retentate in the second circuit system and rate of flowing the collected fluid of step (e) into the second circuit system are independently controlled.

US Pat. No. 10,968,251

METHOD FOR PREPARING STEROID DERIVATIVE FXR AGONIST

Chia Tai Tianqing Pharmac...

1. A preparation method for a compound of formula I,comprising:a), reacting a compound of formula 8 with a compound of formula 9 to obtain a compound of formula 10,

b), reacting from the compound of formula 10 to obtain a compound of formula 11, and

c), reacting from the compound of formula 11 to obtain the compound of formula I,

wherein, R1 is selected from H, Cl, Br or F,
P1 and P2 are each independently selected from a hydroxy protecting group, and
M is selected from a metal cation.

US Pat. No. 10,968,250

INTERMEDIATES FOR THE SYNTHESIS OF BILE ACID DERIVATIVES, IN PARTICULAR OF OBETICHOLIC ACID

NZP UK Limited, Bristol ...

1. A compound of general formula (I):
wherein:
is a carbon-carbon single or double bond;
R1 is C1-4 alkyl optionally substituted with one or more substituents selected from halo, OR7a and NR7aR7b;
where each of R7a and R7b is independently selected from H and C1-4 alkyl;
or R1 together with R2 forms an epoxide group;
R2 is selected from the group consisting of ?O, OH and a protected OH or R2 together with R1 forms an epoxide group;
R3 is selected from the group consisting of H, halo, OH and a protected OH;
when is a carbon-carbon double bond, Y is selected from the group consisting of a bond and an alkylene, alkenylene or alkynylene linker group having from 1 to 20 carbon atoms and optionally substituted with one or more groups R13;
when is a carbon-carbon single bond, Y is selected from the group consisting of a bond and an alkylene linker group having from 1 to 20 carbon atoms and optionally substituted with one or more groups R13; or Y, together with R4 forms a group ?CH2;
each R13 is independently selected from halo, OR8 and NR8R9;
where each of R8 and R9 is independently selected from H and C1-4 alkyl;
R4 is selected from the group consisting of halo, CN, CH(OR10)(OR11), CH(SR10)SR11), NR10R11, BR10R11, C(O)CH2N2, —CH?CH2, —C?CH, CH[C(O)OR10]2, CH(BR10R11)2, azide and a carboxylic acid mimetic group selected from —SO2—NHR30, C(O)NH—SO2R30, NHC(O)NH—SO2R30 and tetrazole optionally substituted with one or more substituents selected from C1-4 alkyl, halo, OH, O(C1-4 alkyl), SO2(C1-4 alkyl), SO2-phenyl and SO2-tolyl;
where R30 is selected from H, C1-6 alkyl C3-7 cycloalkyl or aryl optionally substituted with C1-4 alkyl, halo, OH, O(C1-4 alkyl), SO2(C1-4 alkyl), SO2-phenyl or SO2-tolyl;
where each R10 and R11 is independently selected from:
a. hydrogen and
b. C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, any of which is optionally substituted with one or more substituents selected from halo, NO2, CN, OR19, SR19, C(O)OR19, C(O)N(R19)2, SO2R19, SO3R19, OSO3R19, N(R19)2 and a 6- to 14-membered aryl or 5 to 14-membered heteroaryl group, either of which is optionally substituted with one or more substituents selected from C1-6 alkyl, C1-6 haloalkyl, halo, NO2, CN, OR19, SR19, C(O)OR19, C(O)N(R19)2, SO2R19, SO3R19, OSO3R19 and N(R19)2; and
c. a 6- to 14-membered aryl or 5 to 14-membered heteroaryl group either of which is optionally substituted with one or more substituents selected from C1-6 alkyl, C1-6 haloalkyl, halo, NO2, CN, OR19, SR19, C(O)OR19, C(O)N(R19)2, SO2R19, SO3R19, OSO3R19 and N(R19)2; and
d. a polyethylene glycol residue; or
e. when R4 is CH(OR10)(OR11), CH(SR10)(SR11), NR10R11, BR10R11, CH[C(O)OR10]2 or CH(BR10R11)2 an R10 and an R11 group, together with the atom or atoms to which they are attached, may combine to form a 3 to 10-membered heterocyclic ring;
each R19 is independently selected from H, C1-6 alkyl, C1-6 haloalkyl and a 6- to 14-membered aryl or 5 to 14-membered heteroaryl group either of which is optionally substituted with one or more substituents selected from halo, C1-6 alkyl and C1-6 haloalkyl; or
R5 is selected from the group consisting of H, OH and a protected OH group;
R6 is ?O;
and salts thereof.

US Pat. No. 10,968,249

BILE ACID DERIVATIVES AS FXR/TGR5 AGONISTS AND METHODS OF USE THEREOF

Enanta Pharmaceuticals, I...

1. A compound represented by Formula V-A or Formula V-B, or a pharmaceutically acceptable salt thereof:
wherein:
R1 is selected from the group consisting of:
1) Halogen;
2) Hydroxyl;
3) Substituted or unsubstituted —C1-C8 alkyl;
4) Substituted or unsubstituted —C2-C8 alkenyl;
5) Substituted or unsubstituted —C2-C8 alkynyl;
6) Substituted or unsubstituted —C3-C8 cycloalkyl;
7) Substituted or unsubstituted aryl;
8) Substituted or unsubstituted arylalkyl;
9) Substituted or unsubstituted heterocycloalkyl;
10) Substituted or unsubstituted heteroaryl;
11) Substituted or unsubstituted heteroarylalkyl; and
12) —NR10R11;
m is selected from 0, 1, 2 and 3; and
R10 and R11 are each independently selected from hydrogen, substituted or unsubstituted —C1-C8 alkyl, substituted or unsubstituted —C2-C8 alkenyl, Substituted or unsubstituted —C2-C8 alkynyl, substituted or unsubstituted —C3-C8 cycloalkyl, or R10 and R11 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring.

US Pat. No. 10,968,247

METHODS OF SYNTHESIZING SUBSTITUTED PURINE COMPOUNDS

Epizyme, Inc., Cambridge...

1. A crystalline form of (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((((1r,3 S)-3-(2-(5-(tert-butyl)-1H-benzo[d]imidazol -2-yl)ethyl)cyclobutyl) (isopropyl)amino)methyl)tetrahydrofuran-3,4-diol:or a pharmaceutically acceptable salt or solvate thereof.

US Pat. No. 10,968,246

SUBSTITUTED 4-PHENYL PYRIDINE COMPOUNDS AS NON-SYSTEMIC TGR5 AGONISTS

Ardelyx, Inc., Fremont, ...

1. A method of treating a disease or disorder associated with activation of TGR5 comprising, administering to a patient in need thereof an effective amount of a compound of Formula (I?), wherein the disease or disorder associated with the activation of TGR5 is selected the group consisting of diabetes, Type II diabetes, gestational diabetes, impaired fasting glucose, impaired glucose tolerance, insulin resistance, hyperglycemia, obesity, metabolic syndrome, fatty liver, non-alcoholic fatty liver disease (NAFLD), liver fibrosis, non-alcoholic steatohepatitis (NASH), primary sclerosing cholangitis (PSC), liver cirrhosis, and primary biliary cirrhosis (PBC):
or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof,
wherein:
Q is C?(O), —CH2—, —NR5— or —O—;
when Q is C?(O) then Q1 is —NR5—, when Q is —NR5— or —O— then Q1 is —CH2—, or when Q is —CH2— then Q1 is ?O(CH2)0-1— or —NR5—;
X1 is CR6 or N;
X2 is CR7 or N;
X3 is CR8 or N;
X4 is CR9 or N;
Y is CRb or N;
Ra and Rb are each independently H, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, or halogen;
R1 is H, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, halogen, —S(O)p(C1-C6) alkyl, (C3-C8) cycloalkyl, heterocycloalkyl, —O—(C3-C8) cycloalkyl, or —O-heterocycloalkyl, wherein the alkyl, alkoxy, cycloalkyl, and heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting of halogen, (C1-C4) alkoxy, —OH, —NH2, —NH(C1-C4) alkyl, and —N((C1-C4) alkyl)2; or
R1 and Ra together with the carbon atoms to which they are attached form a heterocycloalkyl; or
R1 and R3, when on adjacent atoms, together with the carbon atoms to which they are attached form a heterocycloalkyl optionally substituted with one or more substituents selected from the group consisting of (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, and halogen;
R2 is (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, or (C1-C6) haloalkoxy;
R2? is H, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, or (C1-C6) haloalkoxy; or
R2 and R2? together with the carbon atom to which they are attached form a (C3-C8) cycloalkyl or heterocycloalkyl;
each R3 is independently, at each occurrence, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, halogen, —S(O)p(C1-C6) alkyl, (C3-C8) cycloalkyl, heterocycloalkyl, —O—(C3-C8) cycloalkyl, or —O-heterocycloalkyl, wherein the alkyl, alkoxy, cycloalkyl, and heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting of halogen, (C1-C4) alkoxy, —OH, —NH2, —NH(C1-C4) alkyl, and —N((C1-C4) alkyl)2; or
R1 and R3 together with the carbon atoms to which they are attached form a heterocycloalkyl optionally substituted with one or more substituents selected from the group consisting of (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, and halogen;
R4 is H, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) hydroxyalkyl, (C1-C6) aminoalkyl, halogen, (C3-C8) cycloalkyl, heterocycloalkyl, —OH, —NH2, CN, —S(O)m(C1-C6) alkyl, —NH(C1-C4) alkyl, or —N((C1-C4) alkyl)2;
each R5 is independently H, (C1-C6) alkyl, —C(O)NR10R11, —C(O)(C1-C6) alkyl, or —C(O)O(C1-C6) alkyl;
each R6 and R9 is independently H, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) hydroxyalkyl, (C1-C6) aminoalkyl, halogen, (C3-C8) cycloalkyl, heterocycloalkyl, —OH, —NH2, CN, —S(O)o(C1-C6) alkyl, —NH(C1-C4) alkyl, or —N((C1-C4) alkyl)2;
each R7 and R8 is independently H, (C1-C8) alkenyl, (C1-C8) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, (C1-C6) hydroxyalkyl, (C1-C6) aminoalkyl, halogen, (C3-C8) cycloalkyl, (C3-C8) cycloalkenyl, heterocycloalkyl, —OH, —NH2, —S(O)qNH2, —S(O)qOH, CN, or (C1-C18) alkyl, wherein 0 to 7 methylene of the (C1-C18) alkyl is optionally replaced by a moiety selected from the group consisting of —O—, —NR13—, —S(O)q—, —C(O)—, —C(CH2)—, or —C(NH)—, provided that when any two methylene in the alkyl is replaced, then two —O—, two —S(O)q—, or two —NR13— and —O— and —NR13— are not contiguous, wherein the alkyl is optionally substituted with one or more R12, and wherein the cycloalkyl and cycloalkenyl are optionally substituted with one or more R13;
R10 and R11 are each independently H or (C1-C6) alkyl optionally substituted with one or more substituent independently selected from the group consisting of —NH2 and OH;
R12 is D, —OH, halogen, —NH2, —NH(C1-C6) alkyl, —N((C1-C6) alkyl)2, —C(O)OH, —OC(O)(C1-C6) alkyl, (C3-C8) cycloalkyl, heterocycloalkyl, (C6-C10) aryl, heteroaryl, or R17, wherein the cycloalkyl, heterocycloalkyl, aryl, and heteroaryl are optionally substituted with one or more substituents selected from the group consisting of —OH, —NH2, —NH(C1-C6) alkyl, —N((C1-C6) alkyl)2, halogen, and R14;
R13 is H, —OH, (C3-C8) cycloalkyl, heterocycloalkyl, (C6-C10) aryl, heteroaryl, or (C1-C12) alkyl, wherein 0 to 7 methylene of the (C1-C12) alkyl is optionally replaced by a moiety selected from the group consisting of —O—, —NR13—, —S(O)r—, —C(O)—, or —C(NH)—, provided that a when any two methylene in the alkyl is replaced, then O and N are not contiguous and wherein the alkyl is optionally substituted with one or more R15, and wherein the cycloalkyl, heterocycloalkyl, aryl, and heteroaryl are optionally substituted with one or more substituents selected from the group consisting of —OH, —C(O)OH, —NH2, —NH(C1-C6) alkyl, and —N((C1-C6) alkyl)2;
R14 is (C3-C8) cycloalkyl, heterocycloalkyl, —O—(C3-C8) cycloalkyl, —O-heterocycloalkyl, (C1-C12) alkyl or (C2-C12) alkenyl, wherein 0 to 7 methylene of the (C1-C12) alkyl and the (C2-C12) alkenyl are optionally replaced by a moiety selected from the group consisting of —O—, —NR13—, —S(O)r—, —C(O)—, or —C(NH)—, provided that a when any two methylene in the alkyl or alkenyl is replaced, then O and N are not contiguous and wherein the alkyl and alkenyl are optionally substituted with one or more R15, and the cycloalkyl and heterocycloalkyl are optionally substituted with one or more R16; or
when R12 is cycloalkyl or heterocycloalkyl, two R14 together with the atom to which they are attached form C?(O); or when R12 is cycloalkyl or heterocycloalkyl, two R14 together with the atoms to which they are attached form a (C3-C8) cycloalkyl or heterocycloalkyl optionally substituted with one or more R13; or when R12 is cycloalkyl or heterocycloalkyl, two R14 together with the atom to which they are attached form a (C3-C8) spirocycloalkyl or a spiroheterocycloalkyl optionally substituted with one or more R13; or when R12 is cycloalkyl or heterocycloalkyl, two R14 together with the atom to which they are attached form a (C6-C10) aryl or heteroaryl optionally substituted with one or more R13;
R15 is —OH, —NH2, —NH(C1-C6) alkyl, —N((C1-C6) alkyl)2, (C3-C8) cycloalkyl, heterocycloalkyl, (C6-C10) aryl or heteroaryl, wherein the (C3-C8) cycloalkyl and heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting of (C1-C6) hydroxyalkyl, (C1-C6) aminoalkyl, —C(O)OH, —OH, —NH2, —NH(C1-C6) alkyl, —N((C1-C6) alkyl)2, and oxo;
R16 is —OH, —C(O)OH, —NH2, —NH(C1-C6) alkyl, —N((C1-C6) alkyl)2, (C1-C6) alkoxy, (C1-C6) hydroxyalkyl, (C3-C8) cycloalkyl, heterocycloalkyl, —O—(C3-C8) cycloalkyl, —O-heterocycloalkyl, (C6-C10) aryl or heteroaryl, wherein the (C3-C8) cycloalkyl and heterocycloalkyl are optionally substituted with one or more substituents selected from the group consisting of (C1-C6) hydroxyalkyl, (C1-C6) aminoalkyl, —C(O)OH, —OH, —NH2, —NH(C1-C6) alkyl, —N((C1-C6) alkyl)2, and oxo;
R17 is (C1-C18) alkyl or (C2-C18) alkenyl, wherein 0 to 8 methylene of the (C1-C18) alkyl and the (C2-C18) alkenyl are optionally replaced by a moiety selected from the group consisting of —O—, —NR13—, —S(O)r—, —C(O)—, or —C(NH)—, provided that a when any two methylene in the alkyl or alkenyl is replaced, then O and N are not contiguous and wherein the alkyl and alkenyl are optionally substituted with one or more R18;
R18 is R19, (C6-C10) aryl, or heteroaryl optionally substituted with one or more R21;
R19 is (C1-C18) alkyl wherein 0 to 8 methylene of the (C1-C18) alkyl is optionally replaced by a moiety selected from the group consisting of —O—, —NR13—, —S(O)r—, —C(O)—, or —C(NH)—, provided that a when any two methylene in the alkyl or alkenyl is replaced, then O and N are not contiguous and wherein the alkyl is optionally substituted with one or more R20;
R20 is (C6-C10) aryl or heteroaryl optionally substituted with one or more R21;
R21 is H, (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C1-C6) haloalkoxy, or halogen; or
two R21 together when on adjacent atoms form a cycloalkyl or heterocycloalkyl optionally substituted with one or more R22;
R22 is —C(O)NH2, —C(O)NH(C1-C6) alkyl, —C(O)N((C1-C6) alkyl)2, —C(O) (C3-C7) cycloalkyl, or —C(O)heterocycloalkyl, wherein the cycloalkyl and heterocycloalkyl are optionally substituted with one or more substituents independently selected from the group consisting of —OH and CN;
each m, o, p, q, and r is independently, at each occurrence, 0, 1, or 2; and
n is 0, 1, or 2.

US Pat. No. 10,968,244

SYNTHESES OF ALLYL PHOSPHINE COMPLEXES OF PALLADIUM

Johnson Matthey Public Li...

1. A process for preparing a complex of formula (1), the process comprising the step of reacting a complex of formula (3) with a monodentate biaryl ligand of formula (4) to form the complex of formula (1),
wherein,
R1 and R2 are, independently, substituted or unsubstituted and are straight-chain alkyl, branched-chain alkyl, cycloalkyl, aryl or heteroaryl, wherein the heteroatoms of the heteroaryl are, independently, sulfur, nitrogen or oxygen, or where the substituted or unsubstituted straight-chain alkyl of R1 and R2 are linked to form a ring structure with E;
R3, R4, R5, R6, R7, R8, R9, R10 and R11 are, independently, H or substituted or unsubstituted groups that are straight-chain alkyl, branched-chain alkyl, cycloalkyl, alkoxy, aryl, heteroaryl, —N(alkyl)2 wherein the alkyl groups are, independently, straight-chain or branched-chain groups, —N(cycloalkyl)2 wherein the cycloalkyl groups are the same or different, —N(aryl)2 wherein the aryl groups are the same or different, —N(heteroaryl)2 wherein the heteroaryl groups are the same or different, or heterocycloalkyl; or
R1/R3 or R2/R3 forms a ring structure with the atoms to which they are attached and in this instance R4/R5, R5/R6, R7/R8, R8/R9, R9/R10 or R10/R11 may independently form a ring structure with the carbon atoms to which they are attached;
R12 is substituted or unsubstituted and is straight-chain alkyl, branched-chain alkyl, cycloalkyl, aryl or heteroaryl wherein the heteroatoms of the heteroaryl are, independently, sulfur, nitrogen, or oxygen;
wherein:
at least one of R7, R8, R9, R10 and R11 is not H, and
when R8, R9 and R10 are H, R7 and R11 are not OMe;
m is 0, 1, 2, 3, 4 or 5;
E is P or As; and
X is a coordinating anionic ligand.

US Pat. No. 10,968,243

ORGANOMETALLIC COMPLEX AND APPLICATION THEREOF IN ELECTRONIC DEVICES

GUANGZHOU CHINARAY OPTOEL...

1. An organometallic complex having the structure represented by any one of the following formulas:
where M is a transition metal element;
m is an integer from 1 to 2, and n is an integer from 1 to 3;
Ar1 is an aromatic hydrocarbon or heteroaromatic cyclic hydrocarbon system which is not substituted or is substituted by R1;
R1 is selected from the group consisting of H, D, linear alkyl containing 1 to 20 carbon atoms, linear alkoxy containing 1 to 20 carbon atoms, linear thioalkoxy containing 1 to 20 carbon atoms, branched or cyclic alkyl containing 3 to 20 carbon atoms, branched or cyclic alkoxy containing 3 to 20 carbon atoms, branched or cyclic thioalkoxy containing 3 to 20 carbon atoms or branched, cyclic silyl containing 3 to 20 carbon atoms, a substituted keto group containing 1 to 20 carbon atoms, alkoxycarbonyl containing 2 to 20 carbon atoms, aryloxycarbonyl containing 7 to 20 carbon atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, an isocyanate group,; a thiocyanate group, an isothiocyanate group, hydroxy, nitro, CF3, Cl, Br, F, a crosslinkable group, a substituted or unsubstituted aromatic or heteroaromatic ring system containing 5 to 40 ring-forming atoms, and aryloxy or heteroaryloxy containing 5 to 40 ring-forming atoms;
is a bidentate ligand;x is an integer from 0 to 2;
y is an integer from 0 to 4;
R1 and R2 are each independently selected from the group consisting of H, F, Cl, Br, I, D, C.N., NO2, CF3, B(OR2)2, Si(R2)3, linear alkane, alkane ether, alkane thioether containing 1 to 10 carbon atoms, branched alkane, cycloalkane, and aryl containing 6 to 10 carbon atoms; and
R2 is independently selected from the group consisting of H, D, linear alkyl containing 1 to 20 carbon atoms, linear alkoxy containing 1 to 20 carbon atoms, linear thioalkoxy containing 1 to 20 carbon atoms, branched or cyclic alkyl containing 3 to 20 carbon atoms, branched or cyclic alkoxy containing 3 to 20 carbon atoms, branched or cyclic thioalkoxy containing 3 to 20 carbon atoms or branched, cyclic silyl containing 3 to 20 carbon atoms, a substituted keto group containing 1 to 20 carbon atoms, alkoxycarbonyl containing 2 to 20 carbon atoms, aryloxycarbonyl containing 7 to 20 carbon atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, an isocyanate group, a thiocyanate group, an isothiocyanate group, hydroxy, nitro, CF3, Cl, Br, F, a crosslinkable group, a substituted or unsubstituted aromatic or heteroaromatic ring system containing 5 to 40 ring-forming atoms, and aryloxy or heteroaryloxy containing 5 to 40 ring-forming atoms.

US Pat. No. 10,968,242

CYCLOPENTANE-BASED MODULATORS OF STING (STIMULATOR OF INTERFERON GENES)

Pfizer Inc., New York, N...

1. A method of treating breast cancer in a mammal, the method comprising administering to the mammal a therapeutically effective amount of the compound:or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,241

PROCESS FOR PRODUCING PHOSPHINATES

BASF SE, Ludwigshafen (D...

1. A method for producing
glufosinate, or a salt thereof, wherein a phosphonous acid monoester of formula (I)

is employed as an intermediate, the method comprising:
(a) reacting a compound of formula (II)

with a compound of formula (III)
R2—OH  (III)
to produce a compound of formula (I); and
(b) further reacting the compound of formula (I) with at least one further reactant to produce glufosinate or a salt thereof,
wherein in each case:
R1 represents (C1-C12)-alkyl, (C1-C12)-haloalkyl, (C6-C10-aryl, (C6-C10)-haloaryl, (C7-C10)-aralkyl, (C7-C10)-haloaralkyl, (C4-C10)-cycloalkyl or (C4-C10)-halocycloalkyl,
R2 represents (C3-C12)-alkyl, (C3-C12)-haloalkyl, (C6-C10)-aryl, (C6-C10)-haloaryl, (C7-C10)-aralkyl, (C7-C10)-haloaralkyl, (C4-C10)-cycloalkyl or (C4-C10)-halocycloalkyl, and
R3 and R4 each independently of one another represent methyl or ethyl,
in the presence of an acidic catalyst and in the presence of water.

US Pat. No. 10,968,240

POLYCATIONIC METHYL PHOSPHOLIPIDS FOR IMPROVED DELIVERY OF NUCLEIC ACIDS TO EUKARYOTIC CELLS

MOLECULAR TRANSFER, INC.,...

1. A compound of Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
each X independently is selected from —O—, —OC(O)O—, —C(O)O—, —O(O)C—, —N(R2)C(O)O—, —C(O)N(R2)—, —OC(O)N(R2)—, and —(R2)NCON(R2)—;
Y is independently (C1-C6)alkyl;
each R is independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, and substituted or unsubstituted arylalkyl, wherein each R group is optionally independently substituted by 1-3 substituent groups, each substituent group independently selected from amino, hydroxyl, (CH2)jOR11, (CH2)jC(O)R11, (CH2)jC(O)OR11, (CH2)jOC(O)R11, (CH2)jNR12R13, (CH2)jC(O)NR12R13, (CH2)jOC(O)NR12R13, (CH2)jN14RC(O)R11, (CH2)jN14RC(O)OR11, (CH2)jN14RC(O)NR12R13, and (CH2)jN14RC(NH)NR12R13, wherein each j is independently an integer selected from 0 to 6;
R1 is independently selected from alkyl, (CH2)jOR11, (CH2)jC(O)R11, and CH2CH(OH)CH2(OH);
R2 is independently selected from hydrogen and (C1-C6)alkyl;
R3 is independently selected from: (CH2)jNR12R13, C(O)CH[(CH2)3NH(CH2)3NH2]—[NH(CH2)3NH2], C(O)CH(NH2)(CH2)3NH2; C(O)CH(NH2)(CH2)4NH2, C(O)CH(NH2)(CH2)3NHC(?NH)NH2, C(O)CH(NH2)(CH2)(C3H3N2), C(O)CH(NH2)(CH2)3NH2; C(O)CH(NH2)CH2NH2, —C(O)CH(NH2)(CH2)2NH2, and —C(O)CH(NH2)CHOH;
R11, R12, R13 and R14 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, perfluoroalkyl, and cycloalkyl, where the alkyl or alkenyl is optionally substituted with one or more substituent selected from the group consisting of amino, primary amino, secondary amino, hydroxy, alkoxy, and hydroxyalkyl.

US Pat. No. 10,968,239

FUNCTIONALIZED ALUMINUM REAGENTS

1. A functionalized aluminum reagent of formula 1
wherein R is a linear or branched alkane group containing 1 to 8 carbon atoms, and R1 is phenylene, or a linear or branched alkane diyl group containing 2 to 10 carbon atoms, or a combination of one or more phenylene groups and one or more linear or branched alkane diyl groups containing 1 to 10 carbon atoms; Q is of formula 2

wherein R6, R7 and R8 are independently a linear or branched alkyl group containing 1 to 3 carbon atoms or a group of formula 3

where R3 and R4 are independently phenyl or a linear or branched alkyl group containing 1 to 10 carbon atoms wherein at least one of R6, R7 and R8 is of formula 3, or R3 and R4 taken together with the nitrogen atom represent a nitrogen containing heterocyclic group containing from 4 to 12 carbon atoms; or R6, R7 and R8 taken together with the silicon atom represent a structure of formula 4

wherein R9 is C1 to C4 linear or branched alkanediyl and Z is N or a group of formula 5

wherein R13 is C1 to C8 alkyl.

US Pat. No. 10,968,238

SUBSTITUTED DIHYDROPYRROLOPYRAZOLE COMPOUND

UBE INDUSTRIES, LTD., Ub...

1. A compound represented by the formula (A1) or (A1?):
wherein
P1 and P2 are each a benzyloxycarbonyl group.

US Pat. No. 10,968,236

TYK2 INHIBITORS AND USES THEREOF

Nimbus Lakshmi, Inc., Ca...

1. A method of inhibiting TYK2 in a biological sample comprising contacting the sample with a compound of formula I, or a pharmaceutically acceptable salt thereof:
wherein:
each of X and Y is independently ?C(R6)—, ?N—, or ?N+(?O?)—, provided that X and Y are not simultaneously ?C(R6)—;
Ring A is phenyl; a 5-6 membered heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur; a 3-6 membered saturated or partially unsaturated heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur; or a 4-6 membered saturated or partially unsaturated carbocyclic ring; wherein Ring A is substituted with m instances of R7;
each of R1 and R1? is independently hydrogen, —R2, halogen, —CN, —NO2, —OR, —SR, —NR2, —S(O)2R, —S(O)2NR2, —S(O)R, —C(O)R, —C(O)OR, —C(O)NR2, —C(O)N(R)OR, —OC(O)R, —OC(O)NR2, —N(R)C(O)OR, —N(R)C(O)R, —N(R)C(O)NR2, or —N(R)S(O)2R; or
R1 and R1? are taken together to form an oxo group or with their intervening atoms to form an optionally substituted 3-7 membered spiro-fused ring having 0-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
each R2 is independently an optionally substituted group selected from C1-6 aliphatic, phenyl, a 4-7 membered saturated or partially unsaturated heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, and a 5-6 membered heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
R3 is a group selected from C1-6 alkyl, phenyl, a 3-7 membered saturated or partially unsaturated carbocyclic ring, a 3-7 membered saturated or partially unsaturated heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, and a 5-6 membered heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur; wherein R3 is substituted with n instances of R8;
R4 is hydrogen or optionally substituted C1-6 aliphatic; or
R4 and one instance of R7 are taken together with their intervening atoms to form a 5-6 membered partially unsaturated or aromatic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen and sulfur;
R5? is an 8-14 membered saturated or partially unsaturated heterocyclic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur; wherein R5? is substituted with p instances of R9;
R6 is hydrogen, —R2, halogen, —CN, —NO2, —OR, —SR, —NR2, —S(O)2R, —S(O)2NR2, —S(O)R, —C(O)R, —C(O)OR, —C(O)NR2, —C(O)N(R)OR, —OC(O)R, —OC(O)NR2, —N(R)C(O)OR, —N(R)C(O)R, —N(R)C(O)NR2, or —N(R)S(O)2R;
each instance of R7, R8, R10, and R11 is independently oxo, —R2, halogen, —CN, —NO2, —OR, —SR, —NR2, —S(O)2R, —S(O)2NR2, —S(O)R, —C(O)R, —C(O)OR, —C(O)NR2, —C(O)N(R)OR, —OC(O)R, —OC(O)NR2, —N(R)C(O)OR, —N(R)C(O)R, —N(R)C(O)NR2, or —N(R)S(O)2R;
each instance of R9 is independently oxo, C1-6 hydroxyaliphatic, —R2, halogen, —CN, —NO2, —OR, —SR, —NR2, —S(O)2R, —S(O)2NR2, —S(O)R, —C(O)R, —C(O)OR, —C(O)NR2, —C(O)N(R)OR, —OC(O)R, —OC(O)NR2, —N(R)C(O)OR, —N(R)C(O)R, —N(R)C(O)NR2, or —N(R)S(O)2R;
L1 is a covalent bond or a C1-6 bivalent saturated or unsaturated, straight or branched hydrocarbon chain wherein one or two methylene units of the chain are optionally and independently replaced by —C(R10)2—, —N(R)—, —N(R)C(O)—, —C(O)N(R)—, —N(R)S(O)2—, —S(O)2N(R)—, —O—, —C(O)—, —OC(O)—, —C(O)O—, —S—, —S(O)— or —S(O)2—; or
L1 and one instance of R7 are taken together with their intervening atoms to form a 5-10 membered partially unsaturated or aromatic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, sulfur, and boron; wherein said ring is substituted by q instances of R11; and R5? is attached to any position of the ring formed by L1 and R7;
m is 0-4;
n is 0-4;
p is 0-6;
q is 0-4; and
each R is independently hydrogen, or an optionally substituted group selected from C1-6 aliphatic, phenyl, a 4-7 membered saturated or partially unsaturated heterocyclic having 1-2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, and a 5-6 membered heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, or:
two R groups on the same nitrogen are taken together with their intervening atoms to form a 4-7 membered saturated, partially unsaturated, or heteroaryl ring having 0-3 heteroatoms, in addition to the nitrogen, independently selected from nitrogen, oxygen, and sulfur.

US Pat. No. 10,968,235

N-AZASPIROCYCLOALKANE SUBSTITUTED N-HETEROARYL COMPOUNDS AND COMPOSITIONS FOR INHIBITING THE ACTIVITY OF SHP2

NOVARTIS AG, Basel (CH)

1. A compound, or a pharmaceutically acceptable salt thereof, selected from:

US Pat. No. 10,968,234

COMPOUND CONTAINING TRICYCLIC HETEROARYL GROUP

Hangzhou Innogate Pharma ...

1. A compound of the following formula (I), or the optical isomers, pharmaceutically acceptable salts, prodrugs, deuterated forms, hydrates, or solvates thereof:wherein M is a group having the following formula (II):
wherein in formula (I) and formula (II):
“” represents the attachment site of formula (II) to U in formula (I);
“*” indicates a chiral center;
A is selected from aryl or heteroaryl;
B is

U is NRd, O or S;
X is hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl, C3-6 cycloalkyl, C2-4 alkenyl, C2-4 alkynyl, 3- to 10-membered heterocyclic, ORe, SRe, NReRe, CN, C(O)Re, C(O)ORe, C(O)NReRe, OC(O)Re, NReC(O)Re, or S(O)2Re;
J and G are each independently NRf, O, S, S(O), S(O)2 or CRgRg;
R1 and R2 are each independently selected from the group consisting of hydrogen, halogen, C1-4 alkyl, C3-6 cycloalkyl, 3- to 8-membered heterocyclic, or C(O)NReRe; wherein the alkyl, cycloalkyl, and heterocyclic can be optionally substituted with one or more Rc;
each of the R3 is independently hydrogen or C1-4 alkyl; when two R3 are simultaneously attached to the same carbon atom, the two R3 and the carbon atom to which they are attached may optionally form a carbonyl group (C?O);
n is 0, 1, 2, or 3;
Ra is hydrogen, C1-4 alkyl, C3-6 cycloalkyl, or 3- to 12-membered heterocyclic; wherein the alkyl, cycloalkyl, heterocyclyl may independently be optionally substituted by one or more halogens, ORe, CN, SO2NReRe, as long as the chemical structure formed is stable and meaningful;
Rb is aryl, heteroaryl, C1-4 alkyl, C3-8 cycloalkyl, 3- to 12-membered heterocyclic, C(O)Re, or C(O)NReRe; wherein the aryl, heteroaryl, alkyl, cycloalkyl, heterocyclyl can be optionally substituted by one or more Rc;
each Rc is independently halogen, C1-4 alkyl, C3-8 cycloalkyl, 3- to 8-membered heterocyclic, C(O)NReRe, NReC(O)Re, ORe, CN, or SO2NReRe;
Rd is hydrogen or C1-4 alkyl;
each Re is independently selected from the group consisting of hydrogen, C1-4 alkyl, C1-4 haloalkyl, C2-4 alkenyl, C2-4 alkynyl, C3-8 cycloalkyl, 3- to 8-membered heterocyclic, aryl, or heteroaryl; or two Re together with the nitrogen atom to which they are attached form 3- to 8-membered heterocyclic containing 1 or 2 N atoms, and 0 or 1 hetero atom selected from O and S;
Rf is hydrogen, C1-8 alkyl, C1-8 haloalkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, 3- to 12-membered heterocyclic, aryl, heteroaryl, C(O)Re, C(O)ORe, C(O)NReRe, S(O)2Re, or S(O)2NRhRh;
each Rg is each independently selected from the group consisting of hydrogen, halogen, or C1-4 alkyl; or two Rg together with the carbon atom to which they are attached form a carbonyl group (C?O); or two Rg together with the same carbon atom to which they attached form 3- to 8-membered cyclic structure which optionally comprise 0, 1 or 2 heteroatoms selected from N, O, S;
each Rh is independently hydrogen or C1-4 alkyl; or two Rh together with the nitrogen atom to which they are attached form 3- to-membered cyclic structure;
wherein each of the above alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, cyclic structure, aryl and heteroaryl is optionally and independently substituted by 1 to 3 substituents each independently selected from the group consisting halogen, C1-4 alkyl, C1-4 haloalkyl, C2-4 alkenyl, C2-4 alkynyl, C3-8 cycloalkyl, 3- to 12-membered heterocyclic, aryl, heteroaryl, CN, NO2, ORe, SRe, NReRe, C(O)Re, C(O)ORe, C(O)NReRe, NReC(O)Re, or S(O)2Re, provided that the chemical structure formed is stable and meaningful;
unless otherwise specified, the aryl is aromatic groups having 6 to 12 carbon atoms; the heteroaryl is 5- to 15-membered heteroaromatic groups; and the cyclic structure is saturated or unsaturated cyclic groups with or without heteroatoms;
with the proviso that A is not any group selected from group consisting of:

wherein “**” means connecting to U; “***” means connecting to B.

US Pat. No. 10,968,233

MONOTHIOL MUCOLYTIC AGENTS

PARION SCIENCES, INC., D...

1. A compound represented by formula (Ia):
wherein
R1 and R2 are each, independently, hydrogen, lower alkyl, halogen, trifluoromethyl, hydroxyl-lower alkyl, phenyl, (phenyl)-lower alkyl, (halophenyl)-lower alkyl, ((lower-alkyl)phenyl)-lower-alkyl, ((lower-alkoxy)phenyl)-lower-alkyl, (naphthyl)-lower-alkyl, or (pyridyl)-lower-alkyl;
R3 and R4 are each, independently, hydrogen, lower alkyl, hydroxyl-lower alkyl, phenyl, (phenyl)-lower alkyl, (halophenyl)-lower alkyl, ((lower-alkyl)phenyl)-lower-alkyl, ((lower-alkoxy)phenyl)-lower-alkyl, (naphthyl)-lower-alkyl, or (pyridyl)-lower-alkyl;
each R5 is, independently, hydrogen —O—(CH2)m—NR7R10, —O—(CH2)m—NR7R7, —O—(CH2)m—NR10R10, —O—(CH2CH2O)m—CH2CH2NR7R10, —O—(CH2)m—NR10—CH2(CHOR8)(CHOR8)n—CH2OR8
-Link-(CH2)m—CAP, -Link-(CH2)n(CHOR8)(CHOR8)n—CAP, -Link-(CH2CH2O)m—CH2—CAP, -Link-(CH2CH2O)m—CH2CH2—CAP, -Link-(CH2)m—(Z)g—CAP, -Link-(CH2)n(Z)g—(CH2)m—CAP, -Link-(CH2)n—NR13—CH2(CHOR8)(CHOR8)n—CAP, -Link-(CH2)n—(CHOR8)mCH2—NR13—(Z)g—CAP, -Link-(CH2)nNR13—(CH2)m(CHOR8)nCH2NR13—(Z)g—CAP, -Link-(CH2)m—(Z)g—(CH2)m—CAP, -Link-NH—C(?O)—NH—(CH2)m—CAP, -Link-(CH2)m—C(?O)NR13—(CH2)m—CAP, -Link-(CH2)n—(Z)g—(CH2)m—(Z)g—CAP, or -Link-Zg—(CH2)m-Het-(CH2)m—CAP,
with the proviso that at least one R5 group contains at least one basic nitrogen;
R6 is, independently, hydrogen, —C(?O)—R7, or an amino acyl of the natural configuration;
each R7 is, independently, hydrogen, lower alkyl, phenyl, substituted phenyl, lower alkyl phenyl, —CH2(CHOR8)m—CH2OR8; 2-furyl or 3-furyl;
each R8 is, independently, hydrogen, lower alkyl, lower alkyl phenyl, —C(?O)—R11, glucuronide, 2-tetrahydropyranyl, or

each R9 is, independently, —CO2R7, —CON(R7)2, —SO2CH3, —C(?O)R7, —CO2R13, —CON(R13)2, —SO2CH2R13, or —C(?O)R13;
each R10 is, independently, —H, —SO2CH3, —CO2R7, —C(?O)—NR7R9, —C(?O)R7, or —CH2—(CHOH)n—CH2OH;
each Z is, independently, —(CHOH)—, —C(?O)—, —(CHNR7R10)—, —(C?NR10)—, —(CHNR13R13)—, or —(C?NR13)—;
each R11 is, independently, hydrogen, lower alkyl, phenyl lower alkyl or substituted phenyl lower alkyl;
each R13 is, independently, hydrogen, lower alkyl, phenyl, substituted phenyl or —CH2(CHOR8)m—CH2OR8, —SO2CH3, —CO2R7, —C(?O)NR7R9, —C(?O)R7, —CH2—(CHOH)n—CH2OH, —(CH2)m—NR7R10, —(CH2)m—NR7R7, —(CH2)m—NR11R11, —(CH2)m—(NR11R11R11)+, —(CH2)m—(CHOR8)m—(CH2)mNR11R11, —(CH2)m—(CHOR8)m—(CH2)mNR7R10, —(CH2)m—NR10R10, —(CH2)m—(CHOR8)m—(CH2)m—(NR11R11R11)+, —(CH2)m—(CHOR8)m—(CH2)mNR7R7;
each g is, independently, an integer from 1 to 6;
each m is, independently, an integer from 1 to 7;
each n is, independently, an integer from 0 to 7;
each -Het- is, independently, —N(R7)—, —N(R10)—, —S—, —SO—, —SO2—; —O—, —SO2NH—, —NHSO2—, —NR7CO—, —CONR7—, —N(R13)—, —SO2NR13—, —NR13CO—, or —CONR13—;
each Link is, independently, —O— or, —O(CH2)m;
each CAP is, independently

with the proviso that when any —CHOR8— or —CH2OR8 groups are located 1,2- or 1,3-with respect to each other, the R8 groups may, optionally, be taken together to form a cyclic mono- or di-substituted 1,3-dioxane or 1,3-dioxolane;
and racemates, enantiomers, diastereomers, tautomers, and pharmaceutically acceptable salts, thereof.

US Pat. No. 10,968,232

ANTIDIABETIC SPIROCHROMAN COMPOUNDS

1. A compound of structural formula I:
or a pharmaceutically acceptable salt thereof;
wherein
T is CH;
U is CR1;
V is CR2;
W is CH;
X is selected from the group consisting of:
(1) oxygen,
(2) —CRbRb,
(3) —C?O, and
(4) —C(Rb)ORb, and
(5) N(Rb);
Z is selected from:

Y is selected from the group consisting of:
(1) —C(Rg)—,
(2) —C(F)—, and
(3) —N—;
R1 and R2 are each independently selected from:
(1) hydrogen, and
(2) —C1-6alkyl,
wherein each alkyl is unsubstituted or substituted with one to three substituents selected from RL, and wherein one of R1 and R2 is C1-6 alkyl, wherein —C1-6 alkyl is substituted with R7;
each R3 is independently selected from the group consisting of:
(1) hydrogen,
(2) halogen, —CN,
(3) —CF3, and
(4) —C1-6alkyl;
R4 is independently selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) —CF3, and
(4) —C1-6alkyl;
R5 is independently selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) —CN,
(4) —CF3,
(5) —C1-6alkyl, and
(6) —C1-5spirocycloalkyl,
or two R5 groups, and the carbons they are attached to, form a —C3-6cycloalkyl ring or a —C2-5cycloheteroalkyl ring;
R6 is selected from the group consisting of:
(1) aryl,
(2) aryl-SO2,
(3) aryl-C1-10 alkyl-,
(4) aryl-N(Ri)—,
(5) aryl-C1-10 alkyl-N(Ri)—,
(6) heteroaryl,
(7) heteroaryl-C1-10 alkyl-, and
(8) heteroaryl-N(Ri)—,
wherein each CH2 is unsubstituted or substituted with 1-2 substituents selected from Ra, and wherein each aryl, and heteroaryl is unsubstituted or substituted with 1-5 substituents selected from Ra:
R7 is selected from the group consisting of:
(1) —CO2R8,
(2) —C1-6alkyl-CO2R8,
(3) —C1-6alkyl-CONHSO2Rm,
(4) —C1-6alkyl-SO2NHCORm,
(5) —C1-6alkyl-tetrazolyl, and
(6) a cycloheteroalkyl selected from the group consisting of:

R8 is selected from the group consisting of:
(1) hydrogen,
(2) —C1-6alkyl,
(3) —C3-6 cycloalkyl, and
(4) aryl-C1-6alkyl,
wherein each alkyl, cycloalkyl and aryl is unsubstituted or substituted with one to three substituents selected from Rj;
Ra is selected from the group consisting of:
(1) —C1-6alkyl,
(2) —OC1-6alkyl,
(3) halogen,
(4) —S(O)nRe,
(5) —S(O)nNRcRd,
(6) —NRcRd,
(7) —C(O)Re,
(8) —OC(O)Re,
(9) —CO2Re,
(10) —CN,
(11) —C(O)NRcRd,
(12) —CF3,
(13) —OCF3,
(14) —OCHF2,
(15) —OCH2CF3,
(16) aryl,
(17) heteroaryl,
(18) C3-6cycloalkyl, and
(19) C2-5cycloheteroalkyl,
wherein each alkyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with 1-3 substituents selected from: halogen, —C1-6alkyl, —O—C1-6alkyl, —CF3, CO2H, and —CO2C1-6 alkyl;
each Rb is independently selected from the group consisting of:
(1) hydrogen,
(2) —C(O)Rd, and
(3) —C1-10alkyl,
wherein each alkyl is unsubstituted or substituted with one to five halogens;
Rc and Rd are each independently selected from the group consisting of:
(1) hydrogen,
(2) C1-10alkyl,
(3) C2-10alkenyl,
(4) C3-6cycloalkyl,
(5) C3-6 cycloalkyl-C1-10alkyl-,
(6) C2-5cycloheteroalkyl,
(7) C2-5cycloheteroalkyl-C1-10alkyl-,
(8) aryl,
(9) heteroaryl,
(10) aryl-C1-10alkyl-, and
(11) heteroaryl-C1-10alkyl-,
wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with one to three Rf substituents;
each Re is independently selected from the group consisting of:
(1) hydrogen,
(2) —C1-10alkyl,
(3) —C2-10 alkenyl,
(4) —C3-6 cycloalkyl,
(5) —C3-6 cycloalkyl-C1-10alkyl-,
(6) —C2-5cycloheteroalkyl,
(7) —C2-5cycloheteroalkyl-C1-10alkyl,
(8) aryl,
(9) aryl-C1-10alkyl-,
(10) heteroaryl, and
(11) heteroaryl-C1-10alkyl-,
wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with one to three substituents selected from Rh;
each Rf is selected from the group consisting of:
(1) halogen,
(2) C1-10alkyl,
(3) —OH,
(4) —O—C1-4alkyl,
(5) —S(O)m—C1-4alkyl,
(6) —CN,
(7) —CF3,
(8) —OCHF2, and
(9) —OCF3,
wherein each alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, halogen, C1-6alkyl, cyano and S(O)2C1-6alkyl;
Rg is selected from the group consisting of:
(1) hydrogen, and
(2) —C1-10alkyl,
wherein each alkyl is unsubstituted or substituted with one to five halogens;
each Rh is selected from the group consisting of:
(1) halogen,
(2) C1-10alkyl,
(3) —OH,
(4) —O—C1-4alkyl,
(5) —S(O)m—C1-4alkyl,
(6) —CN,
(7) —CF3,
(8) —OCHF2, and
(9) —OCF3,
wherein each alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, halogen, C1-6alkyl, cyano and S(O)2C1-6alkyl;
Ri is independently selected from the group consisting of:
(1) hydrogen, and
(2) —C1-6 alkyl;
Rj is independently selected from the group consisting of:
(1) —C1-6alkyl,
(2) —ORe,
(3) —NRcS(O)mRe,
(4) halogen,
(5) —S(O)mRe,
(6) —S(O)mNRcRd,
(7) —NRcRd,
(8) —C(O)Re,
(9) —OC(O)Re,
(10) —CO2Re,
(11) —CN,
(12) —C(O)NRcRd,
(13) —NRcC(O)Re,
(14) —NRcC(O)ORe,
(15) —NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C3-6cycloalkyl, and
(20) —C2-5cycloheteroalkyl;
each Rk is independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) —C2-10 alkenyl,
(3) —C3-6 cycloalkyl,
(4) —C3-6 cycloalkyl-C1-10alkyl-,
(5) —C2-5cycloheteroalkyl,
(6) —C2-5cycloheteroalkyl-C1-10alkyl-,
(7) aryl,
(8) heteroaryl,
(9) aryl-C1-10alkyl-, and
(10) heteroaryl-C1-10 alkyl-,
each RL is independently selected from the group consisting of:
(1) —CO2C1-6alkyl,
(2) —C1-10alkyl,
(3) —C2-10alkenyl,
(4) —C2-10alkynyl,
(5) —C3-6cycloalkyl,
(6) —C2-6cycloheteroalkyl,
(7) aryl, and
(8) heteroaryl,
wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with 1-4 substituents selected from C1-6alkyl, halogen, and —OC1-6alkyl;
each n is independently selected from: 0, 1 or 2;
each m is independently selected from: 0, 1 or 2;
each p is independently selected from: 0, 1, or 2;
each q is independently selected from: 0, 1 or 2;
each t is independently selected from: 0, 1 or 2; and
each u is independently selected from: 0, 1, 2, or 3.

US Pat. No. 10,968,231

SUBSTITUTED CYCLYL-ACETIC ACID DERIVATIVES FOR THE TREATMENT OF METABOLIC DISORDERS

SCOHIA PHARMA, INC., Kan...

1. A compound represented by the formula (I):
wherein X is an oxygen atom or a bond;
Y1 and Y2 are each independently CH or N;
Z is an optionally substituted alkyl group, an optionally substituted alkoxy group or a halogen atom;
W is an optionally substituted alkyl group, an optionally substituted alkoxy group, —NRW1RW2, an optionally substituted carbamoyl group or an optionally substituted cyclic group;
RW1 is an optionally substituted alkyl group or an acyl group;
RW2 is a hydrogen atom or a substituent;
L is
andR1, R2 and R3 are each independently a hydrogen atom or a substituent; or
R1 and R2 are optionally bonded to each other to form, together with each adjacent carbon atom, an optionally further substituted 3- to 6-membered ring,
or a salt thereof.

US Pat. No. 10,968,230

SPIRO-STRUCTURED COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING SAME

LG Chem, Ltd.

1. A spiro compound represented by the following Chemical Formula 1:
in Chemical Formula 1,
X is NR9, O, S or CR101R102,
Y is O, S, CR103R104 or SiR105R106,
R9 is -L1Ar1,
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
R4 to R8, R11 to R14, R21 to R24, R31 to R34, R101 to R106, and Ar1 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are optionally bonded to an adjacent group to form a ring provided that when R103 and R104 are phenyl, R103 and R104 are not bonded to each other to form a ring,
r4 is an integer of 1 or 2, and
when r4 is 2, R4s are the same as or different from each other;
with the proviso that the following compound is excluded from the derivatives of Chemical Formula 1:

US Pat. No. 10,968,229

SEVEN-MEMBERED RING COMPOUNDS

Idemitsu Kosan Co., Ltd.,...

1. A compound of formula
wherein B1 is N or a CR81 group,
B2 is N or a CR82 group,
B3 is N or a CR83 group,
B4 is N or a CR84 group,
B5 is N or a CR85 group,
B6 is N or a CR86 group,
B7 is N or a CR87 group,
B8 is N or a CR88 group,
B9 is N or a CR89 group,
B10 is N or a CR90 group,
B11 is N or a CR91 group,
B12 is N or a CR92 group,
B13 is N or a CR93 group,
B14 is N or a CR94 group, and
X is an NR95 group, S or O,
wherein R81, R82, R83, R84, R85, R86, R87, R88, R89, R90, R91, R92, R93 and R94 are each independently: H; F; CN; a C1-C25 alkyl group, which can optionally be substituted by E and/or interrupted by D; a C6-C24 aryl group, which can optionally be substituted by G; a C2-C30 heteroaryl group, which can optionally be substituted by G; or a -(A5)s-(A6)t-(A7)u-(A8)v-R17 group, and
R95 is a -(A1)o-(A2)p-(A3)q-(A4)r-R16 group,
wherein o, p, q, r, s, t, u and v are each independently 0 or 1,
R16 and R17 are each independently: H; an —NR10R11 group; a —C(?O)R15 group; an —Si(R12)(R13)(R14) group; a C6-C24 aryl group, which can optionally be substituted by G; or a C2-C30 heteroaryl I group, which can optionally be substituted by G,
wherein R10, R11 and R15 are each independently: a C6-C24 aryl group, which can optionally be substituted by G; or a C2-C30 heteroaryl group, which can optionally be substituted by G, and
if o, p, q and r are each 0, then R16 is neither H nor the —NR10R11 group,
A1, A2, A3, A4, A5, A6, A7 and A8 are each independently: an —Si(R12?)(R13?)— group; a C6-C24 arylene group, which can optionally be substituted by G: or a C2-C30 heteroarylene group, which can optionally be substituted by G, and
R12, R13, R12?, R13? and R14 are each independently: a C1-C25 alkyl group, which can optionally be substituted by E and/or interrupted by D; a C6-C24 aryl group, which can optionally be substituted by G; or a C2-C30 heteroaryl group, which can optionally be substituted by G,
each D is independently: —CO—, —COO—, —S—, —SO—, —SO2—, —O—, an —NR65— group, an —SiR70R71— group, a —POR72— group, a —CR63?CR64— group or —C?C—,
each E is independently: an —OR69 group, an —SR69 group, an —NR65R66 group, a —COR68 group, a —COOR67 group, a —CONR65R66 group, —CN or F,
each G is independently: E; an —Si(R71)(R74)(R75) group; a C1-C18 alkyl group; a C6-C24 aryl group; a C6-C24 aryl group that is substituted by F, by a C1-C18 alkyl group or by a C1-C18 alkyl group that is interrupted by O; a C2-C30 heteroaryl group; or a C2-C30 heteroaryl group that is substituted by F, by a C1-C18 alkyl group or by a C1-C18 alkyl group that is interrupted by O, E,
wherein R63 and R64 are each independently: H; a C6-C18 aryl group; a C6-C18 aryl group that is substituted by a C1-C18 alkyl group or a C1-C18 alkoxy group; a C1-C18 alkyl group; or a C1-C18 alkyl group that is interrupted by —O—,
R65 and R66 are each independently: a C6-C18 aryl group; a C6-C18 aryl group that is substituted by a C1-C18 alkyl group or a C1-C18 alkoxy group; a C1-C18 alkyl group; or a C1-C18 alkyl group that is interrupted by —O—; or R65 and R66 together form a five or six membered ring,
R67 is a C6-C18 aryl group; a C6-C18 aryl group that is substituted by a C1-C18 alkyl group or a C1-C18 alkoxy group; a C1-C18 alkyl group; or a C1-C18 alkyl group that is interrupted by —O—,
R68 is H; a C6-C18 aryl group; a C6-C18 aryl group that is substituted by a C1-C18 alkyl group or a C1-C18 alkoxy group; a C1-C18 alkyl group; or a C1-C18 alkyl group that is interrupted by —O—,
R69 is a C6-C18 aryl group; a C6-C18 aryl group that is substituted by a C1-C18 alkyl group or a C1-C18 alkoxy group; a C1-C18 alkyl group; or a C1-C18 alkyl group that is interrupted by —O—,
R70 and R71 are each independently: a C1-C18 alkyl group; a C6-C18 aryl group; or a C6-C18 aryl group that is substituted by a C1-C18 alkyl group,
R72 is a C1-C18 alkyl group; a C6-C18 aryl group; or a C6-C18 aryl group that is substituted by a C1-C18 alkyl group, and R73, R74 and R75 are each independently: a C1-C25 alkyl group, which can optionally be interrupted by O; a C6-C24 aryl group, which can optionally be substituted by one or more C1-C18 alkyl groups; or a C2-C30 heteroaryl group, which can optionally be substituted by one or more C1-C18 alkyl groups,
not more than two of B1, B2, B3 and B4 are N, and
not more than two of B5, B6, B7 and B8 are N.

US Pat. No. 10,968,228

METHODS OF PREPARING SUBSTITUTED 12A,13-DIHYDRO-6H-BENZO[5,6][1,4]DIAZEPINO[1,2-A]INDOLES

IMMUNOGEN, INC., Waltham...

1. A method for preparing a compound of formula (I):
wherein:
R1 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R2 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R3 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R4 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R5 is H, F, Cl, Br, I, NR?R?, OR, SR, or R;
R? is H, C1-10 alkyl, (CH2CH2X)nRc, C2-10 alkenyl, C2-10 alkynyl, COR, NR2, OR, C3-10 cycloalkyl, C4-10 cycloalkenyl, C4-10 cycloalkynyl, or 3- to 18-membered heterocyclyl, wherein the 3- to 18-membered heterocyclyl contains 1, 2, 3, 4, 5, or 6 heteroatoms independently selected from the group consisting of N, O, S, and P;
R? is H, C1-10 alkyl, (CH2CH2X)nRc, C2-10 alkenyl, C2-10 alkynyl, COR, NR2, OR, C3-10 cycloalkyl, C4-10 cycloalkenyl, C4-10 cycloalkynyl, or 3- to 18-membered heterocyclyl, wherein the 3- to 18-membered heterocyclyl contains 1, 2, 3, 4, 5, or 6 heteroatoms independently selected from the group consisting of N, O, S, and P;
each R is independently H, C1-10 alkyl, (CH2CH2X)nRc, C2-10 alkenyl, C2-10 alkynyl, C3-10 cycloalkyl, C4-10 cycloalkenyl, C4-10 cycloalkynyl, C6-18 aryl, 5- to 18-membered heteroaryl, or 3- to 18-membered heterocyclyl, wherein the 5- to 18-membered heteroaryl contains one or more heteroatoms independently selected from the group consisting of N, O, and S, and further wherein the 3- to 18-membered heterocyclyl contains 1, 2, 3, 4, 5, or 6 heteroatoms independently selected from the group consisting of N, O, S, and P;
each Rc is independently H or C1-4 alkyl;
each X is independently —NH—, —O—, or —S—; and
each n is independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24;
comprising the following step:
reacting a compound of formula (II):

wherein:
R1 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R2 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R3 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R4 is H, F, Cl, Br, I, CN, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, COR?, NR?R?, NR?COR?, NH(C?NH)NH2, NCO, N3, (XCH2CH2)nRc, OR, OCOR?, OCONR?R?, OSO3H, SR, SOR?, SO2R?, SO2NR?R?, SO3H, C3-10 cycloalkyl, C4-10 cycloalkenyl, or C4-10 cycloalkynyl;
R5 is H, F, Cl, Br, I, NR?R?, OR, SR, or R;
R? is H, C1-10 alkyl, (CH2CH2X)nRc, C2-10 alkenyl, C2-10 alkynyl, COR, NR2, OR, C3-10 cycloalkyl, C4-10 cycloalkenyl, C4-10 cycloalkynyl, or 3- to 18-membered heterocyclyl, wherein the 3- to 18-membered heterocyclyl contains 1, 2, 3, 4, 5, or 6 heteroatoms independently selected from the group consisting of N, O, S, and P;
R? is H, C1-10 alkyl, (CH2CH2X)nRc, C2-10 alkenyl, C2-10 alkynyl, COR, NR2, OR, C3-10 cycloalkyl, C4-10 cycloalkenyl, C4-10 cycloalkynyl, or 3- to 18-membered heterocyclyl, wherein the 3- to 18-membered heterocyclyl contains 1, 2, 3, 4, 5, or 6 heteroatoms independently selected from the group consisting of N, O, S, and P;
each R is independently H, C1-10 alkyl, (CH2CH2X)nRc, C2-10 alkenyl, C2-10 alkynyl, C3-10 cycloalkyl, C4-10 cycloalkenyl, C4-10 cycloalkynyl, C6-18 aryl, 5- to 18-membered heteroaryl, or 3- to 18-membered heterocyclyl, wherein the 5- to 18-membered heteroaryl contains one or more heteroatoms independently selected from the group consisting of N, O, and S, and further wherein the 3- to 18-membered heterocyclyl contains 1, 2, 3, 4, 5, or 6 heteroatoms independently selected from the group consisting of N, O, S, and P;
each Rc is independently H or C1-4 alkyl;
each X is independently —NH—, —O—, or —S—; and
each n is independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24;
with Fe in the presence of NH4Cl, to form the compound of formula (I) above.

US Pat. No. 10,968,227

ISOQUINOLINE ETHER COMPOUNDS AS MGLUR4 ALLOSTERIC POTENTIATORS, COMPOSITIONS, AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTION

Vanderbilt University, N...

1. A compound having a structure of the following formula:
wherein:
X is CH, or N;
X1 is CH, or N;
X2 is CH, or N;
Y is CH, or N;
R1 is tetrahydrofuran optionally substituted by at least one R2, morpholine optionally substituted by one or more R2, dioxane, or alkoxy;
R2 is H, CD3, halogen, alkyl, alkoxy, CONH2, CN, or ?O;
R3 is independently H, halogen, alkyl, CD3, cycloalkyl, CF3, CN, or alkoxy;
R4 is H, halogen, alkyl, CD3, cycloalkyl, CF3, or CN;
n is 0-6;
provided that at least one of Y and X is N; and
provided that one of X1 and X2 is N;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,226

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

UNIVERSAL DISPLAY CORPORA...

1. A compound of Formula I:
wherein
X1 to X23 are independently selected from carbon or nitrogen, wherein at least one of X19 to X23 is nitrogen, and there is no direct bond between X18 and X19 or X23;
wherein if any of the X1 to X23 is carbon, then RA, RB, RC, RD, RE, and RF each independently represent mono to the maximum allowable substitution, or no substitution to each respective ring;
RA, RB, RC, RD, RE, and RF are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; or two adjacent groups RA, RB, RC, RD, RE, and RF can join to form a ring; and
Ar1 is a six-membered aromatic ring that is optionally substituted.

US Pat. No. 10,968,225

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF CYSTIC FIBROSIS

Fondazione Istituto Itali...

7. A method of modulating CFTR protein or ABC protein activities in a mammal in need thereof comprising administering a compound of formula I
or pharmaceutically acceptable salts or solvates thereof wherein:
R1 is hydrogen;
Z is C?O or SO2;
X1, X2, X3 and X4 are independently selected from the group consisting of CRvii and N, with the proviso that the number of nitrogen atoms in the ring is comprised from 0 to 2;
R2 is selected from the group consisting of hydrogen, C1-6alkyl, haloC1-6alkyl, C3-6cycloalkyl, aryl, heteroaryl, CORvii, COORvii, heterocycloalkyl, CONHRvii, CONRviiRix, OH, O—C1-6alkyl, O—C1-6alkylaryl, O—C3-6cycloalkyl, O-heterocycloalkyl, O-heteroaryl, O-aryl, O-haloC1-6alkyl, C1-6alkyl-O—C1-6alkyl, C1-6alkyl-O—C3-6cycloalkyl, C1-6alkyl-O-heterocycloalkyl, C1-6alkyl-O-aryl, C1-6alkyl-O-heteroaryl, CN, NO2, NRxRxi, N(Rix)CORx, N(Rix)COORxi, N(Rix)CONRxiRx, N(Rix)SO2Rx, SO2Rx, SO2NRixRx, halogen, and hydroxy-C1-6alkyl;
A1, A2, A3, and A4, are independently selected from the group consisting of CRxiiRxiii, O, NRxiv, CO and SO2, wherein
Rxii and Rxiii are independently selected from the group consisting of hydrogen, C1-6alkyl, C3-6cycloalkyl, heterocycloalkyl, haloC1-6alkyl, CORviii, COORviii, CONHRviii, CONRviiiRix, OH, O—C1-6alkyl, O-aryl, O—C1-6alkylaryl, O-heteroaryl, O—C3-6cycloalkyl, O-heterocycloalkyl, C1-6alkylaryl, C3-6cycloalkylaryl, C3-6cycloalkylheteroaryl, C3-6cycloheteroalkylaryl, C3-6cycloheteroalkylheteroaryl, C1-6alkylheteroaryl, S-aryl, S-heteroaryl, SO-aryl, SO-heteroaryl, SO2-aryl, SO2-heteroaryl, C1-6alkyl-O—C1-6alkyl, CN, halogen, NRxRxi, N(Rix)CORx;
Rxiv is selected from the group consisting of hydrogen, C1-6alkyl, C1-6alkylaryl, C1-6alkyl-C3-6cycloalkyl, C1-6alkyl-heterocycloalkyl, C3-6cycloalkyl, heterocycloalkyl, hydroxyl-C1-6alkyl, CORviii, COORviii, CONHRviii, CONRviiiRix, SO2Rviii, C1-6alkyl-O—C1-6alkyl, C1-6alkyl-O-aryl, C1-6alkyl-O-heteroaryl, C1-6alkyl-O-heterocycloalkyl, C1-6alkylCOORviii;
or
when each of A1 and A3, or A2 and A4, or A1 and A4 represents CRxiiRxiii, the two groups Rxii can be linked together to form a ring and thus the moiety

has a meaning selected from the group consisting of:

n and m are each independently selected from the group consisting of 0, 1, 2;
B represents an unsubstituted or a substituted aromatic or heteroaromatic ring selected from the group consisting of:
whereinR5, R6, R7, R8, and R9 are independently selected from the group consisting of hydrogen, halogen, C1-6alkyl, haloC1-6alkyl, C3-6cycloalkyl, O—C1-6alkyl, O—C3-6cycloalkyl, O-heterocycloalkyl, O-haloC1-6alkyl, CORviii, COORviii, CONHRviii, CONRviiiRix, OH, CN, NRxRxi, N(Rix)CORx, N(Rix)CONRxRxi and hydroxy-C1-6alkyl
or
when R6 and R7 are present on a 6-membered heteroaromatic ring, taken together with the carbon atoms to whom they are bound, they can form a saturated or unsaturated 5-membered or 6-membered carbocyclic ring or a 5-membered or 6-membered heterocycloalkyl containing from 1 to 3 heteroatoms selected from O, N, and S or a 5-membered or 6-membered heteroaryl ring containing from 1 to 3 heteroatoms selected from O, N, and S;
Y and W are independently selected from the group consisting of O, S, SO2, CRivRv, CRv, N, and NRvi;
R?, Rii, Riii and Riv are independently selected from the group consisting of hydrogen, C1-6alkyl, haloC1-6alkyl, halogen, OH, O—C1-6alkyl and O-haloC1-6alkyl or
when Ri and Rii, or Riii and Riv are taken together with the carbon atoms to whom they are bound, they can represent C?O;
Rv is selected from the group consisting of hydrogen, C1-6alkyl, haloC1-6alkyl, O—C1-6alkyl, halogen, C3-6cycloalkyl, OH and O-haloC1-6alkyl;
Rvi is selected from the group consisting of hydrogen and C1-6alkyl;
Rvii is selected from the group consisting of hydrogen, C1-6alkyl, C3-6cycloalkyl, haloC1-6alkyl, O-haloC1-6alkyl, CORviii, COORviii, CONHRviii, CONRviiiRix, OH, O—C1-6alkyl, halogen, CN, NO2, NRxRxi, N(Rix)CORx, N(Rix)COORxi, N(Rix)CONRxRxi, and N(Rix)SO2Rx;
Rviii is selected from the group consisting of hydrogen, C1-6alkyl, C3-6cycloalkyl, aryl, heteroaryl, heterocycloalkyl, hydroxy-C1-6alkyl and C1-6alkyl-O—C1-6alkyl;
Rix is selected from the group consisting of hydrogen, C1-6alkyl, hydroxy-C1-6alkyl, and C1-6alkyl-O—C1-6alkyl;
Rx is selected from the group consisting of hydrogen, C1-6alkyl, C3-6cycloalkyl, heterocycloalkyl, aryl, heteroaryl, hydroxy-C1-6alkyl, and C1-6alkyl-O—C1-6alkyl;
Rxi is selected from the group consisting of hydrogen, C1-6alkyl, hydroxy-C1-6alkyl, C1-6alkyl-O—C1-6alkyl, aryl-C1-6alkyl, heteroaryl-C1-6alkyl, and heterocycloalkyl-C1-6alkyl;
wherein the compound is not 3-(5-(2-chlorobenzoyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)-N-(6-methylpyridin-3-yl)benzamide, tert-butyl 4-(4-((4-(3-(3-((4-((4-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)phenyl)amino)phenyl)carbamoyl)-6-(methoxymethyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-1-yl)benzamido)phenyl)amino)phenoxy)piperidine-1-carboxylate, or 7-oxo-N-(4-((4-(piperidin-4-yloxy)phenyl)amino)phenyl)-1-(3-((4-((4-(piperidin-4-yloxy)phenyl)amino)phenyl)carbamoyl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide.

US Pat. No. 10,968,224

2,11-DIAZA-[3.3](2,6)PYRIDINOPHANE COMPOUNDS AND THEIR APPLICATION AS LIGANDS OF ESSENTIAL METAL ION BASED MRI CONTRAST AGENTS AND 52MN BASED PET CONTRAST AGENTS

DEBRECENI EGYETEM, Debre...

1. A compound selected from:

US Pat. No. 10,968,223

IMIDAZO[4,5-C]PYRIDINE AND PYRROLO[2,3-C]PYRIDINE DERIVATIVES AS SSAO INHIBITORS

Proximagen, LLC, Plymout...

1. A process for the preparation of a compound of formula (1a) or a pharmaceutically acceptable salt, or N-oxide thereofcomprising reacting a compound of formula (IIIa) or (Va) with a compound of formula (IX) to form the compound of formula (Ia)wherein:Y is selected from hydrogen, hydroxyl, —NH2, —NH—C1-4-alkyl, —NH-halo-C1-4-alkyl, and —C1-4-alkoxy;
Z is selected from hydrogen, halogen, hydroxyl, cyano, C1-4-alkyl, halo-C1-4-alkyl, C1-4-alkoxy, halo-C1-4-alkoxy, —CONH2, —SO2NH2, —NH2, —NHC1-4-alkyl, and —NHhalo-C1-4-alkyl;
R1 is a phenyl ring, or a 5 or 6-membered heteroaryl ring, either ring being optionally substituted with one or more substituents selected from halogen, cyano, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, a 3-7 membered cycloalkyl ring, —OR5, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR4AR4B, —C(O)NR4AR4B, —C(O)R5, —C(O)OR5, and —NR6S(O)2R5;wherein:R4A, R4B, R5, and R6 are each independently selected from hydrogen, C1-4-alkyl and halo-C1-4-alkyl, or
R4A and R4B together with the nitrogen to which they are attached form a 3-7 membered cyclic amino group, optionally substituted by one or more substituents selected from: halogen, hydroxyl, cyano, C1-4-alkyl, halo-C1-4-alkyl, C1-4-alkoxy, halo-C1-4-alkoxy, —CONH2, —SO2NH2, —NH2, —NHC1-4-alkyl, and —NHhalo-C1-4-alkyl;
W is a phenyl ring or a 5 or 6-membered heteroaryl ring selected from pyridinyl, pyridazinyl, pyrazinyl, pyrimidinyl, oxazolyl, thiazolyl, and imidazolyl, any of which rings being optionally substituted with one or more substituents selected from halogen, cyano, oxo, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, —OR5, —NR7AR7B, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR7AR7B, —C(O)NR7AR7B, —C(O)R5, —C(O)OR5, —SO2R5, —SO2NR7AR7B, and —NR6S(O)2R5;
R7A and R7B are independently hydrogen, C1-4-alkyl, or halo-C1-4-alkyl;
V is selected from a bond, —O—, —N(R6)—, —(C?O)—, —CONR6—, —NR6C(O)—, and —C1-4-alkylene-, wherein the C1-4-alkylene group is optionally substituted by halogen, and any one of the carbon atoms of the C1-4-alkylene group may be replaced by —O— or —N(R6)—;
R3 is selected from hydrogen, —C1-4-alkyl, —C1-4-alkyl-C1-4-alkoxy, a 3-7 membered heterocyclic ring, a 3-7 membered cycloalkyl ring, and a 5 or 6-membered heteroaryl ring, any one of the rings being optionally substituted with one or more substituents selected from halogen, oxo, hydroxyl, cyano, C1-4-alkyl, halo-C1-4-alkyl, cyano-C1-4-alkyl, —OR5, —NR4AR4B, —NR6C(O)OR5, —NR6C(O)R5, —NR6C(O)NR4AR4B, —C(O)NR4AR4B, —C(O)R5, —C(O)OR5, —SO2R5, —SO2NR4AR4B, and —NR6S(O)2R5;PROVIDED THAT groups —WVR3 and/or R1 are not:wherein:n is 0, 1, or 2;
R? and R? are independently selected from the group consisting of H, —C1-C6alkyl, —(C?O)—C1-C6alkyl, and —(C?O)OC(CH3)3; and
R?? is H, OH, or C1-C6 alkyl.

US Pat. No. 10,968,222

2-AZABICYCLO HEXANE JAK INHIBITOR COMPOUND

1. A compound of formula:or a pharmaceutically-acceptable salt thereof.

US Pat. No. 10,968,221

SUBSTITUTED [1,2,4]TRIAZOLO[1,5-A]PYRAZINES AS LSD1 INHIBITORS

Incyte Corporation, Wilm...

10. A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

US Pat. No. 10,968,220

FGFR4 INHIBITOR, PREPARATION METHOD THEREFOR AND PHARMACEUTICAL USE THEREOF

ABBISKO THERAPEUTICS CO.,...

1. A compound of formula (IVa-1), a stereoisomer or pharmaceutically acceptable salt thereof:
wherein,
Z is

R2, R3, R4 and R5 are each independently selected from the group consisting of H, deuterium, Cl, F, hydroxyl, methyl, isopropyl, cyclopropyl, 3-oxacyclobutyl, trifluoromethyl, trideuteromethyl and —O—R11,
or R2 and R4, R3 and R5 are taken together with the directly attached carbon atoms to form a 5-8 membered heterocyclyl, the heteroatom is N or O;
R8 is selected from the group consisting of H, deuterium, halogen, cyano, nitro, azido, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, 3-10 membered heterocyclyl, C5-10 aryl, 5-10 membered heteroaryl, —C0-8—S(O)rR10, —C0-8—P(O)(R10)2, —C0-8—O—R11, —C0-8—C(O)OR11, —C0-8—C(O)R12, —C0-8—O—C(O)R12, —C0-8—NR13R14, —C0-8—C(O)NR13R14, —C0-8—N(R13)—C(O)R12 and —C0-8—N(R13)—C(O)OR11,
above groups are further optionally substituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, azido, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, C3-6 cycloalkyl, 3-8 membered heterocyclyl, C5-8 aryl, 5-8 membered heteroaryl, —C0-4—S(O)rR10, —C0-4—O—R11, —C0-4—C(O)OR11, —C0-4—C(O)R12, —C0-4—O—C(O)R12, —C0-4—NR13R14, —C0-4—C(O)NR13R14, —C0-4—N(R13)—C(O)R12 and —C0-4—N(R13)—C(O)OR11, above groups are further more optionally substituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, azido, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, C3-6 cycloalkyl, 3-8 membered heterocyclyl, C5-8 aryl, 5-8 membered heteroaryl, —C0-4-S(O)rR10, —C0-4—O—R11, —C0-4—C(O)OR11, —C0-4—C(O)R12, —C0-4—O—C(O)R12, —C0-4—NR13R14, —C0-4-C(O)NR13R14, —C0-4—N(R13)—C(O)R12 and —C0-4—N(R13)—C(O)OR11;
X1 is —CH— or N;
R10 is selected from the group consisting of H, deuterium, C1-8 alkyl, C2-8 alkenyl, C3-8 cycloalkyl, 3-10 membered heterocyclyl, C1-8 haloalkyl, C5-10 aryl, 5-10 membered heteroaryl, amino, mono-C1-8 alkylamino, di-C1-8 alkylamino and C1-8 alkanoylamino;
R11 is selected from the group consisting of H, deuterium, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, 3-10 membered heterocyclyl, C5-10 aryl and 5-10 membered heteroaryl, above groups are unsubstituted or substituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C3-8 cycloalkyl, 3-10 membered heterocyclyl, C5-10 aryl, 5-10 membered heteroaryl, C1-8 alkylsulfonyl, C1-8 alkylsulfonylamino, amino, mono-C1-8 alkylamino, di-C1-8 alkylamino, ?O or hydroxyl;
R12 is selected from the group consisting of H, deuterium, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkoxy, C3-8 cycloalkyl, C3-8 cycloalkyloxy, 3-10 membered heterocyclyl, 3-10 membered heterocyclyloxy, C5-10 aryl, 5-10 membered heteroaryl, C5-10 aryloxy and 5-10 membered heteroaryloxy, above groups are unsubstituted or substituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C3-8 cycloalkyl, 3-10 membered heterocyclyl, C5-10 aryl, 5-10 membered heteroaryl, C1-8 alkylsulfonyl, C1-8 alkylsulfonylamino, amino, mono-C1-8 alkylamino, di-C1-8 alkylamino, ?O or hydroxyl;
R13 and R14 are each independently selected from the group consisting of H, deuterium, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, 3-10 membered heterocyclyl, C5-10 aryl, 5-10 membered heteroaryl, C1-8 alkylsulfonyl and C1-8 alkanoyl, or R13 and R14 are taken together with the directly attached nitrogen atom to form a 4-10 membered heterocyclyl,
above groups are unsubstituted or substituted by one or more substituents selected from the group consisting of deuterium, halogen, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C3-8 cycloalkyl, 3-10 membered heterocyclyl, C5-10 aryl, 5-10 membered heteroaryl, C1-8 alkylsulfonyl, C1-8 alkylsulfonylamino, amino, mono-C1-8 alkylamino, di-C1-8 alkylamino, ?O or hydroxyl; and
r is 0, 1 or 2;
wherein unless otherwise defined, the heterocyclyl is a saturated or partially unsaturated monocyclic or polycyclic hydrocarbon substituent containing 1 or 2 heteroatoms selected from nitrogen, oxygen or sulfur, the polycyclic cycloalkyl is a spiro, fused or bridged cycloalkyl, and the heteroaryl is a heteroaromatic system containing 1 or 2 heteroatoms selected from nitrogen, oxygen or sulfur.

US Pat. No. 10,968,219

3-SUBSTITUTED PROPIONIC ACIDS AS ?V INTEGRIN INHIBITORS

Bristol-Myers Squibb Comp...

1. A compound of Formula (I)wherein:A, E, and G are independently N, O, S, NR6a, CHR6b or CR6b;
L1 and L2 are each independently C1-4 alkylene;
M and L are independently N or C with the proviso that M and L are not both N;
wherein A, L, E, G, and L form a ring moiety selected from pyrazole, pyrrole, thiazole, imidazole, oxazole, and pyrrolidine;
X is a C1-6 alkylene substituted with 0, 1, or 2 R7b;
Z is a covalent bond, O, S, NH, —O—(C1-3 alkylene)-, —S—(C1-3 alkylene)-, or —NH—(C1-3 alkylene)-, wherein the C1-3 alkylene is each independently substituted with 0, 1, or 2 R7a;
n is an integer of 1 or 2;
r is an integer of 0, 1, 2, or 3;
R1 is an Arginine mimetic moiety selected from the group consisting of
one of the asterisks in each of the arginine mimetics moiety is an attachment point to X, and the other two asterisks are hydrogen;R2 is hydrogen or C1-6 alkyl;
R3 is hydrogen, C1-6 alkyl, 3- to 10-membered carbocyclyl, carbocyclylalkyl, 6- to 10-membered aryl, arylalkyl, 3- to 14-membered heterocyclyl, heterocyclylalkyl, 5- to 14-membered heteroaryl, or heteroarylalkyl, wherein the alkyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl, by themselves or as part of another group, are each independently substituted with 0, 1, 2, or 3 R8;
or R2 and R3 taken together with the atom to which they are attached form a carbocyclyl or a heterocyclyl, wherein the carbocyclyl and heterocyclyl are each independently substituted with 0, 1, 2, or 3 R12;
R4 is hydrogen, C1-10 alkyl, 3- to 10-membered carbocyclyl, carbocyclylalkyl, 3- to 10-membered heterocyclyl, heterocyclylalkyl, 6- to 10-membered aryl, arylalkyl, 5- to 14-membered heteroaryl, heteroarylalkyl, NRaRb, ORa, S(O)nR10, C(O)NRaRb, NHC(O)ORa, NHC(O)NRaRb, NHC(O)R10, OC(O)NRaRb, OC(O)R10, NHS(O)nNRaRb, or NHS(O)nR10; wherein the alkyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl, by themselves or as part of another group, are each independently substituted with 0, 1, 2, or 3 R9;
R5 is hydrogen, R5a, or a structural moiety selected from

R5a and R5b are each independently C1-6 alkyl, phenyl, or 5- to 7-membered heterocyclyl, wherein the alkyl, phenyl, and heterocyclyl are each independently substituted with 0 to 3 R5d;
R5c is C1-6 alkyl or 5- to 7-membered carbocyclyl, wherein the alkyl and carbocyclyl are each independently substituted with 0 to 3 R5d;
R5d, at each occurrence, is independently halo, OH, alkoxy, oxo, or alkyl; or alternatively, two adjacent R5d, together with the atoms to which they are attached, form a carbocyclyl moiety;
R6a is each independently hydrogen, C1-6 alkyl, haloalkyl, alkoxy, amino, haloalkoxy, hydroxyalkyl, aminoalkyl, or C3-5 cycloalkyl, wherein the cycloalkyl is substituted with 0, 1, 2, or 3 halo, cyano, nitro, amino, or OH;
R6b is each independently hydrogen, halo, cyano, nitro, amino, OH, C1-6 alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, aminoalkyl, or C3-5 cycloalkyl, wherein the cycloalkyl is substituted with 0, 1, 2, or 3 halo, cyano, nitro, amino, or OH;
R7a and R7b are each independently halo, cyano, hydroxyl, amino, C1-6 alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, amido, carbamate, or sulfonamide;
R8 is each independently halo, cyano, oxo, nitro, OH, NRaRb, C1-6 alkyl, alkoxy, alkylamino, haloalkyl, haloalkoxy, haloaminoalkyl, hydroxyalkyl, aminoalkyl, alkylsulfonyl, sulfonamide, 3 to 6 membered carbocyclyl, 3 to 6 membered heterocyclyl, 6- to 10-membered aryl, or 5- to 10-membered heteroaryl; or alternatively, two R8 at adjacent positions, together with the atoms to which they are attached, form a carbocyclyl or heterocyclyl; wherein the aryl and heteroaryl, by themselves or as part of another group, are each independently substituted with one or more groups independently selected from halo, cyano, hydroxyl, amino, C1-6 alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, amido, carbamate, and sulfonamide; and the carbocyclyl and heterocyclyl, by themselves or as part of another group, are each independently substituted with one or more groups independently selected from halo, cyano, hydroxyl, amino, oxo, C1-6 alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, amido, carbamate, and sulfonamide;
R9 at each occurrence is independently halo, cyano, nitro, OH, NRaRb, C1-6 alkyl, alkoxy, alkylamino, haloalkyl, haloalkoxy, haloaminoalkyl, hydroxyalkyl, aminoalkyl, alkylsulfonyl, sulfonamide, 3 to 6 membered carbocyclyl, 3 to 6 membered heterocyclyl, 6- to 10-membered aryl, or 5- to 10-membered heteroaryl; or alternatively, two R9 at adjacent positions, together with the atoms to which they are attached, form a carbocyclyl or heterocyclyl; wherein the aryl and heteroaryl, by themselves or as part of another group, are each independently substituted with one or more groups independently selected from halo, cyano, hydroxyl, amino, C1-6 alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, amido, carbamate, and sulfonamide; and the carbocyclyl and heterocyclyl, by themselves or as part of another group, are each independently substituted with one or more groups independently selected from halo, cyano, hydroxyl, amino, oxo, C1-6 alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, amido, carbamate, and sulfonamide;
R10 is C1-6 alkyl, 3- to 10-membered carbocyclyl, 3- to 10-membered heterocyclyl, 6- to 10-membered aryl, or 5- to 10-membered heteroaryl; wherein the alkyl, carbocyclyl, heterocyclyl are each independently substituted with 0, 1, 2, or 3 R11;
R11 is halo, cyano, nitro, OH, amino, C1-6 alkyl, alkoxy, 3- to 10-membered carbocyclyl, 3- to 10-membered heterocyclyl, 6- to 10-membered aryl, or 5- to 10-membered heteroaryl; wherein the aryl, alkyl, and heteroaryl are each independently substituted with 0, 1, 2, or 3 R13;
R12, R13 and R14, at each occurrence, are independently halo, cyano, nitro, OH, amino, C1-6 alkyl, alkoxy, aminoalkyl, haloalkyl, haloalkoxy, haloaminoalkyl, 3 to 6 membered carbocyclyl, 3 to 6 membered heterocyclyl, 6- to 10-membered aryl, or 5- to 10-membered heteroaryl; wherein the aryl and heteroaryl, by themselves or as part of another group, are each independently substituted with one or more groups independently selected from halo, cyano, hydroxyl, amino, C1-6 alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, amido, carbamate, and sulfonamide; and the carbocyclyl and heterocyclyl, by themselves or as part of another group, are each independently substituted with one or more groups independently selected from halo, cyano, hydroxyl, amino, oxo, C1-6 alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxy, haloalkoxy, amido, carbamate, and sulfonamide;
Ra and Rb, at each occurrence, are independently hydrogen, C1-10 alkyl, 3- to 10-membered carbocyclyl, or 3- to 10-membered heterocyclyl; wherein the alkyl, carbocyclyl, heterocyclyl are each independently substituted with 0, 1, 2, or 3 R14;
Re is OH, C1-4 alkyl, halo, haloalkyl, C1-4 cycloalkyl, amino, amido, carbamate, or sulfonamide;
Rf is hydrogen, CH3, CH2CH3, or COOCH2CH3; and
Rg is selected from CH3, CH2CH3, CH2CCl3, phenyl, 4-fluorophenyl, 4-methoxyphenyl, benzyl,
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,218

TETRAHYDROPYRIDOPYRIMIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

Hoffmann-La Roche Inc., ...

1. A compound of formula I,
wherein:
R1 is hydrogen, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl or C3-7cycloalkyl;
R2 is phenyl or pyridinyl, wherein said phenyl or pyridinyl is unsubstituted, or substituted by one, two or three substituents independently selected from C1-6alkyl, cyano, C3-7cycloalkylC1-6alkoxy, C3-7cycloalkyl, haloC1-6alkoxy, amino, C1-6alkylamino, (C1-6alkyl)2amino, halogen, C1-6alkoxy, C1-6alkoxypyrrolidinyl, C1-6alkylcarbonylpiperazinyl, C1-6alkylsulfonylpiperazinyl, C1-6alkoxycarbonylpiperazinyl, morpholinyl, piperazinyl, oxopiperazinyl, oxopyrrolidinylC1-6alkoxy, pyrrolidinylC1-6alkoxy, pyrrolidinyl, oxopyrrolidinyl, tetrahydrofuranylC1-6alkoxy and tetrahydrofuranyl; and
R3 is imidazolyl, oxazolyl, pyrazolyl, thiazolyl or triazolyl, wherein said imidazolyl, oxazolyl, pyrazolyl, thiazolyl or triazolyl is unsubstituted, or substituted by C1-6alkyl, halogen, haloC1-6alkyl, C3-7cycloalkyl, C1-6alkoxy, haloC1-6alkoxy or phenylC1-6alkyl;
or a pharmaceutically acceptable salt, or an enantiomer thereof.

US Pat. No. 10,968,217

TETRAHYDROPYRIDOPYRIMIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

Hoffmann-La Roche Inc., ...

1. A compound of formula I,
wherein:
R1 is C1-6alkoxy, C1-6alkyl, C3-7cycloalkyl, haloC1-6alkoxy, haloC1-6alkyl or hydrogen;
R2 is benzothiophenyl, imidazolyl, indazolyl, indolyl, isoxazolyl, oxazolyl, phenyl, pyridinyl, pyrimidinyl, thiazolyl or thiophenyl, wherein said benzothiophenyl, imidazolyl, indazolyl, indolyl, isoxazolyl, oxazolyl, phenyl, pyridinyl, thiazolyl or thiophenyl is unsubstituted or substituted by one, two or three substituents independently selected from C1-6alkoxy, C1-6alkoxyC1-6alkoxy, C1-6alkyl, C3-7cycloalkyl, cyano, haloC1-6alkoxy, haloC1-6alkyl, halogen, hydroxy, hydroxyC1-6alkoxy, hydroxyC1-6alkyl, nitro and phenyC1-6alkyl; and
Z is CH or N;
or a pharmaceutically acceptable salt, or an enantiomer thereof.

US Pat. No. 10,968,216

4,5-ANNULATED 1,2,4-TRIAZOLONES

BAYER AKTIENGESELLSCHAFT,...

1. A compound of general formula (I)
in which
R1 represents a group selected from
a C1-C8-alkyl group, which is optionally substituted with a group selected from C3-C8-cycloalkyl, phenyl and monocyclic or bicyclic heteroaryl,
wherein said phenyl substituent is optionally substituted, one, two or three times with one or more substituents independently selected from a halogen atom, a C1-C3-alkyl group, a C1-C4-haloalkyl group, a C1-C3-alkoxy group and a hydroxy group,
a C2-C8-haloalkyl group,
a C3-C8-cycloalkyl group, which is optionally substituted, one or two times, each substituent independently selected from a halogen atom, a hydroxy group, a phenyl group and a —N(R7)(R8) group,
wherein said phenyl substituent is optionally substituted, one, two or three times, each substituent independently selected from a halogen atom, a C1-C3-alkyl group, a C1-C4-haloalkyl group, a C1-C3-alkoxy group and a hydroxy group,
a C2-C6-cyanoalkyl group,
a C2-C6-hydroxyalkyl group,
a (C2-C6-hydroxyalkyl)-O—(C2-C6-alky)-group,
a —(C2-C6-alkyl)-N(R7)(R8) group,
a —(C1-C6-alkyl)-C(?O)N(R7)(R8) group,
a 4- to 7-membered, optionally unsaturated, heterocyclic group, which is connected to the rest of the molecule via a carbon atom, and which is optionally substituted one or two times, each substituent independently selected from a C1-C3-alkyl group, a 5- to 6-membered heteroaryl group, a —C(?O)O(C1-C4-alkyl) group, a —C(?O)(C1-C6-alkyl) group, a —C(?O)(C3-C6-cycloalkyl) group, a —S(?O)2(C1-C6-alkyl) group and a oxo (?O) group,
wherein said 5- to 6-membered heteroaryl substituent is optionally substituted, one, two or three times, each substituent independently selected from a halogen atom or a group selected from C1-C3-alkyl, C1-C4-haloalkyl, C1-C3-alkoxy and hydroxy,
a phenyl group, which is optionally substituted, one, two, three, four or five times, each substituent independently selected from a halogen atom or a group selected from C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C2-C6-alkenyl, C2-C6-alkynyl, aryl, —(C1-C6-alkyl)-aryl, -aryl-(C1-C6-alkyl), C1-C6-alkoxy, —O(C2-C6-alkenyl), C1-C6-haloalkoxy, C3-C8-cycloalkoxy, hydroxy, aryl, —O-aryl, cyano, —C(?O)OR6, —C(?O)N(R7)(R8), —N(R7)(R8), —(C1-C6-alkyl)-N(R7)(R8), —(C1-C6-alkyl)-C(?O)OR6, —(C1-C6-alkyl)-C(?O)N(R7)(R8), —SH, —S—(C1-C6-alkyl), —S—(C2-C6-alkenyl), —S(?O)2N(R7)(R8), —S(?O)2(C1-C6-alkyl), —S(?O)2—O—(C2-C6-alkenyl), —S(?O)(?NR14)(C1-C3-alkyl), —N(O)2, —P(?O)(C1-C3-alkyl)2 and SF5,
or wherein two vicinal substituents of said phenyl groups may form together a 5- or 6-membered, optionally heterocyclic, aromatic or non-aromatic ring, having optionally 1-3 heteroatoms independently selected from —N?, —NH—, —N(R7)—, —O—, —S—, and optionally containing a C(?O) group, and wherein the so formed ring is optionally substituted one or two times, each substituent independently selected from a halogen atom or a group selected from
C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, aryl, —(C1-C6-alkyl)-aryl, -aryl-(C1-C6-alkyl), C3-C8-cycloalkyl, C1-C6-alkoxy, —O(C2-C6-alkenyl), C1-C6-haloalkoxy, C3-C8-cycloalkoxy, aryl, —O-aryl, cyano, —C(O)OH, hydroxy, —SH, —S—(C1-C6-alkyl), —S—(C2-C6-alkenyl), —S(?O)2(C1-C6-alkyl), —N(O)2, and —N(R7)(R8)
and
a monocyclic or bicyclic heteroaryl group which is optionally substituted one, two or three times, each substituent independently selected from a halogen atom or a group selected from
C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, —(C1-C6-alkyl)-aryl, -aryl-(C1-C6-alkyl), C3-C8-cycloalkyl, C1-C6-alkoxy, —O(C2-C6-alkenyl), C1-C6-haloalkoxy, C3-C8-cycloalkoxy, cyano, —C(?O)OR6, hydroxy, —SH, —S—(C1-C6-alkyl), —S—(C2-C6-alkenyl), —S(?O)2(C1-C6-alkyl), —N(O)2, and —N(R7)(R8),
R2 represents a hydrogen atom or a halogen atom,
R3 represents a group selected from
a C1-C6-alkyl group,
a C3-C8-cycloalkyl group,
a C1-C6-haloalkyl group,
a C1-C6-hydroxyalkyl group,
a C2-C6-alkenyl group,
a C2-C6-alkinyl group,
a C4-C8-cycloalkenyl group,
a (C1-C6-alkyl)-N(R7)R8 group,
a —(C1-C6-alkyl)-N(H)C(?O)R6 group,
a —(C1-C6-alkyl)-N(H)C(?O)OR15 group,
a —(C1-C6-alkyl)-(4- to 7-membered nitrogen containing heterocycloalkyl) group, wherein said 4- to 7-membered nitrogen containing heterocycloalkyl group is connected to the alkyl group via a carbon atom of the heterocycloalkyl group and wherein said 4- to 7-membered nitrogen containing heterocycloalkyl group is optionally substituted with a C1-C3-alkyl group,
and
a phenyl group,
which is optionally substituted, one, two or three times, each substituent independently selected from a halogen atom or a group selected from C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, aryl, —(C1-C6-alkyl)-aryl, -aryl-(C1-C6-alkyl), C3-C8-cycloalkyl, C1-C6-alkoxy, —O(C2-C6-alkenyl), C1-C6-haloalkoxy, C3-C8-cycloalkoxy, aryl, —O-aryl, cyano, —C(?O)OR6, hydroxy, —SH, —S—(C1-C6-alkyl), —S—(C2-C6-alkenyl), —S(?O)2(C1-C6-alkyl), —N(O)2, and —N(R7)(R8),
R4 and R5 jointly form an optionally unsaturated, heterocyclic ring A of partial formula (i)

whereby ring A in addition to the two mandatory atoms, the nitrogen atom and the carbon atom bridging the two rings, bears additional 3 to 6 members selected from —O—, —S—, —S(?O)—, —S(?O)2—, —S(?O)(?NR14)—, —N?, —N(R7)—, —C(?O)—, —CH?, ?CR11?, —C(R12)2—, —C(H)(R13)—,
R6 represents a hydrogen atom or a group selected from
a C1-C6-alkyl group and a benzyl group,
R7 and R8 represent, independently from each occurrence, a hydrogen atom or a group selected from
a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-hydroxyalkyl group, a haloalkyl group, a aryl group, a (C1-C6-alkyl)-aryl group, and a —(C2-C6-alkyl)-N(R9)(R10) group, or
R7 and R8 together with the nitrogen to which they are attached represent a
nitrogen containing 4- to 7-membered heterocycloalkyl group,
wherein said 4- to 7-membered nitrogen containing heterocycloalkyl group is optionally substituted with a group selected from
C1-C6-alkyl, —S—(C1-C6-alkyl), —S—(C2-C6-alkenyl), —S(?O)2(C1-C3-alkyl), —S(?O)2—(C2-C6-alkenyl), and —C(?O)OR6—,
R9 and R10 represent, independently from each occurrence, a hydrogen atom or a C1-C3-alkyl group,
or
R9 and R10 together with the nitrogen to which they are attached represent a nitrogen containing 4- to 7-membered heterocycloalkyl group,
R11 represents, independently from each occurrence a hydrogen atom, a halogen atom or a group selected from
C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, aryl, —(C1-C6-alkyl)-aryl, -aryl-(C1-C6-alkyl), C3-C8-cycloalkyl, C1-C6-alkoxy, —O(C2-C6-alkenyl), C1-C6-haloalkoxy, C3-C8-cycloalkoxy, aryl, —O-aryl, cyano, —C(?O)OR6—, hydroxy, —SH, —S—(C1-C6-alkyl), —S—(C2-C6-alkenyl), S(?O)2(C1-C6-alkyl), —S(?O)2—(C2-C6-alkenyl), —N(O)2, and —N(R7)(R8)
R12 represents, independently from each occurrence, a hydrogen atom, a halogen atom or a C1-C3-alkyl group,
R14 represents a group selected from
C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, aryl, —(C1-C6-alkyl)-aryl, -aryl-(C1-C6-alkyl), C3-C8-cycloalkyl, C1-C6-alkoxy, —O(C2-C6-alkenyl), C1-C6-haloalkoxy, C3-C8-cycloalkoxy, aryl, —O-aryl, cyano, —C(?O)OR6—, hydroxy, —SH, —S—(C1-C6-alkyl), —S—(C2-C6-alkenyl), S(?O)2(C1-C6-alkyl), —S(?O)2—(C2-C6-alkenyl), —N(O)2, and —N(R7)(R8),
R14 represents a hydrogen atom or a group selected from
a cyano group and a —C(?O)(C1-C3-haloalkyl) group,
R15 represents a group selected from
a C1-C6-alkyl group and a benzyl group,
or a tautomer, an N-oxide, or a salt thereof, or a salt of a tautomer or an N-oxide of said compound.

US Pat. No. 10,968,215

PYRIDO FIVE-ELEMENT AROMATIC RING COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREOF

SHANGHAI HAIHE PHARMACEUT...

1. A compound of formula I, or a pharmaceutically acceptable salt, an enantiomer, a diastereomer, a tautomer, a solvate, or a polymorph thereof,
wherein X1 is CR4 or N;
X2 is CR5;
X3 is CR6 or N; and at most one of X1, X3 is N;
R4 is selected from H, a halogen, substituted or unsubstituted C1-C6 alkyl;
R5 or R6 is selected from H, a halogen, —COOH, —CN, substituted or unsubstituted 5-8 membered aryl, substituted or unsubstituted 5-8 membered heteroaryl, substituted or unsubstituted 5-8 membered aryl fused to substituted or unsubstituted 5-8 membered heterocyclic group, substituted or unsubstituted 5-8 membered heteroaryl fused to substituted or unsubstituted 5-8 membered heterocyclic group, substituted or unsubstituted 5-8 membered aryl fused to substituted or unsubstituted 5-8 membered carbocyclic group, substituted or unsubstituted 5-8 membered heteroaryl fused to substituted or unsubstituted 5-8 membered carbocyclic group, substituted or unsubstituted 4-8 membered saturated or unsaturated carbocyclic group, substituted or unsubstituted 4-8 membered saturated or unsaturated heterocyclic group, substituted or unsubstituted C1-C6 alkylcarbonyl, —C(O)O-(substituted or unsubstituted C1-C6 alkyl), —C(O)(NRaRb), substituted or unsubstituted —(CH2)mNRaRb, substituted or unsubstituted C1-C6 alkyl, boronic acid group, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl; wherein the heteroaryl or heterocyclic group contains 1-3 hetero atoms selected from N, O, S, P; m is an integer from 0 to 5; and said “substituted” means having one or more substituents selected from group A;
Wherein Ra, Rb are each independently selected from H, a halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted 5-8 membered carbocyclic ring, substituted or unsubstituted 5-8 membered heterocyclic ring, or Ra and Rb are bonded to N to form a substituted or unsubstituted 4-8 membered heterocyclic ring; wherein said heterocyclic ring contains 1-3 hetero atoms selected from N, O, S, or P;
R1 is

R2 is selected from halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted aryl;
R3 is

wherein, R7 is selected from H, substituted or unsubstituted C1-C6 alkyl;
R8 and R9 are each independently selected from H, a substituted or unsubstituted C1-C6 alkyl;
Y is selected from

wherein, R12 and R13 are each independently selected from H, substituted or unsubstituted C1-C4 alkyl;
R14 and R15 are each independently selected from H, a halogen, —NH2, —NO2, —CF3, substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C1-C4 alkoxy, substituted or unsubstituted (CH2)nNRcRd, or R14 and R15 are joined to form a substituted or unsubstituted 5-6 membered saturated heterocyclic ring, or R14 and R15 are linked to form a substituted or unsubstituted 5-6 membered aromatic ring; n is an integer of 0-4;
R16 is H, a substituted or unsubstituted C1-C4 alkyl;
R17 and R19 are each independently selected from H, a substituted or substituted C1-C4 alkyl, substituted or unsubstituted C1-C4 alkoxy, —(CH2)nNRcRd; n is an integer from 0-4;
R18 is selected from H, a halogen, —NH2, —NO2, substituted or substituted C1-C4 alkyl, substituted or unsubstituted C1-C4 alkoxy, substituted or unsubstituted (CH2)nNRcRd; where n is an integer from 0-4;
R20 and R21 are each independently selected from H, a substituted or substituted C1-C4 alkyl;
R22 is selected from H, a substituted or unsubstituted C1-C4 alkyl;
or substituted or unsubstituted C1-C4 alkoxy;wherein Rc, Rd are each independently selected from H, a substituted or unsubstituted C1-C4 alkyl;
Z is selected from N or CH;
R10 and R11 are each independently selected from: H, —OH, a substituted or unsubstituted C1-C6 alkyl, —ORe, substituted or unsubstituted 4-8 membered heterocyclic group, substituted or unsubstituted 4-8 membered carbocyclic group, substituted or unsubstituted 5-8 membered aryl, —NRfRg; wherein said heterocyclic ring contains 1-3 hetero atoms selected from N, O, S, or P; and said “substituted” means having one or more substituents selected from group B;
wherein Re is selected from H, a substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted saturated or unsaturated 4-8 membered carbocyclic ring, substituted or unsubstituted saturated or unsaturated 4-8 membered heterocyclic ring, substituted or unsubstituted 5-8 membered aryl, substituted or unsubstituted 5-8 membered heteroaryl, —(CH2)p(substituted or unsubstituted 5-8 membered aryl), —(CH2)p(substituted or unsubstituted 5-8 membered heteroaryl); wherein the heterocyclic or heteroaryl group comprises 1-3 heteroatoms selected from N, O, S, or P; p is an integer from 0 to 3; and said “substituted” refers to one or more of the following substituent: halogen, C1-C4 alkyl, C1-C4 alkoxy, —NO2, —NRsRt;
wherein Rf and Rg are each independently selected from: H, a substituted or unsubstituted C1-C6 alkyl, wherein the substituent is —OH, C1-C4 alkoxy, or —NRsRt;
group A substituents are selected from the group consisting of H, ?O, —CN, —COOH, —NRsRt, a halogen, substituted or unsubstituted C1-C6 alkoxycarbonyl, unsubstituted or substituted C1-C6 alkyl, substituted or unsubstituted 4-8 membered heterocyclic group, substituted or unsubstituted C1-C4 alkoxy; wherein the heterocyclic group contains 1-3 hetero atoms selected from N, O, S or P;
group B substituents are selected from the group consisting of H, —OH, a halogen, unsubstituted or substituted C1-C6 alkyl, —NRsRt, —NO2, substituted or unsubstituted C1-C6 alkoxycarbonyl, substituted or unsubstituted C1-C6 alkylsulfonyl, substituted or unsubstituted C1-C6 alkylcarbonyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted 4-6 membered heterocyclic ring, substituted or unsubstituted C5-C8 heteroaryl, Boc, benzyl; wherein said heteroaryl comprises 1-3 heteroatoms selected from N, O, S or P;
also, in the group A and group B substituents and Ra, Rb, the substitution means having one or more substitutions selected from group C: H, a halogen, —OH, —CN, C1-C4 alkyl, C1-C4 alkoxy, —NRsRt, 5-8 membered aryl, 4-8 membered heterocyclic group, Boc, C1-C4 acyl; and said substitution is one or more substituents;
and, in the R7, R8, R9, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, Rc, Rd, the “substituted” means having one or more substituents selected from the group D:H, a halogen, C1-C4 alkyl, C1-C4 haloalkyl, nitro, —OH, amino;
Rs and Rt are each independently selected from the group consisting of: H, a C1-C4 alkyl, C1-C4 haloalkyl.

US Pat. No. 10,968,214

KRAS G12C INHIBITORS

Eli Lilly and Company, I...

1. A compound of the formula:
wherein m is 0-2;
each R1 is F; and
R2 is selected from: H, F, and Cl;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,212

COMPOUNDS HAVING ESTROGEN RECEPTOR ALPHA DEGRADATION ACTIVITY AND USES THEREOF

Accutar Biotechnology Inc...

1. A compound of Formula (I) or tautomer, stereoisomer, pharmaceutically acceptable salt or hydrate thereof:wherein:X1 is selected from CH2, NR8, O, and S;
R1 is selected from H, C1-C6 alkyl, halo, heterocycle, and heteroaryl, each of which is substituted with 0, 1, 2, or 3 R5;
R2 is selected from H, C1-C6 alkyl, and C3-C6 cycloalkyl, each of which is substituted with 0, 1, 2, or 3 R5;
R3 is selected from H, C1-C6 alkyl, halo, hydroxy, and sulfhydryl, each of which is substituted with 0, 1, 2, or 3 R5;
R4 is selected from H, C1-C6 alkyl, and acyl, each of which is substituted with 0, 1, 2, or 3 R5;
each R5 is independently selected from C1-C6 alkyl, halo, cyano, and hydroxy;
R6, R7, and R8 are each independently selected from H, C1-C6 alkyl, and acyl, each of which is substituted with 0, 1, 2, or 3 R5;
R9 is selected from H, C1-C6 alkyl, halo, hydroxy, and sulfhydryl, each of which is substituted with 0, 1, 2, or 3 R5; and
L* is a linker of 1 to 16 carbon atoms in length, wherein one or more carbon atoms are optionally replaced by C(O), O, NR4, S, C2-alkenyl, C2-alkynyl, cycloalkyl, aryl, heterocycle, or heteroaryl.

US Pat. No. 10,968,211

HEPATITIS B CORE PROTEIN MODULATORS

Assembly Biosciences, Inc...

1. A compound represented by:
wherein
Y is O;
RZ is selected from the group consisting of H, methyl, ethyl, propyl, phenyl and benzyl;
Rm? and Rm are each independently selected from the group consisting of H, C1-6alkyl (optionally substituted by one, two or three substituents each independently selected from halogen and hydroxyl), and C2-6alkenyl (optionally substituted by one, two or three substituents each independently selected from halogen and hydroxyl);
Rc is selected from the group consisting of H, C1-6alkyl and C2-6alkenyl;
R77 is selected from the group consisting of H, halogen, cyano, and C1-6alkyl;
R78 is phenyl (optionally substituted with one, two, three or four substituents each independently selected from the group consisting of R73);
X2 is selected from the group consisting of S(O)w (wherein w is 0, 1, or 2), O, —C(O)— and NR?,
R79 is selected from the group consisting of H, hydroxyl, halogen, C1-6alkyl, —C(O)—O—C1-6alkyl, heterocycle (optionally substituted by one or more substituents selected from the group consisting of halogen, NR?R?, —C(O)—O—C1-6alkyl, carboxy and C1-6alkyl), —C(O)—NR?R?, —C(?NH)—NR?R?, heteroaryl, phenyl (optionally substituted by one or more substituents selected from the group consisting of halogen, NR?R?, —C(O)—O—C1-6alkyl, carboxy, C1-6alkoxy, and C1-6alkyl), C2-6alkenyl, C2-6alkynyl, C1-6alkoxy, carboxy, NR?R?, —C(O)—C1-6alkyl, C3-6cycloalkyl, —NR?—C(O)— C1-6alkyl, NR?—C(O)— O—C1-6alkyl, —S(O)w—C1-6alkyl (where w is 0, 1 or 2), —S(O)w—NR?R? (where w is 0, 1 or 2), and —NR?—S(O)w— C1-6alkyl (where w is 0, 1 or 2));
R73 is selected from the group consisting of H, halogen, hydroxyl, nitro, cyano, carboxy, oxo, C1-6alkyl, —C(O)—O—C1-6alkyl, heterocycle (optionally substituted by one or more substituents selected from the group consisting of halogen, hydroxyl, oxo, NR?R?, —C(O)—O—C1-6alkyl, carboxy and C1-6alkyl), —C(O)—NR?—C1-6alkyl, —C(?NH)—NR?R?, heteroaryl, phenyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy, carboxy, oxo, NR?R?, —C(O)—C1-6alkyl, —C3-6cycloalkyl, NR?—C(O)— C1-6alkyl, NR?—C(O)— O—C1-6alkyl, —S(O)w—C1-6alkyl (where w is 0, 1 or 2), —S(O)w—NR?R? (where w is 1, 2 or 3), —NR?—S(O)w— C1-6alkyl (where w is 0, 1 or 2), C(O)—NR?— C1-6alkyl, C(O)—C1-3alkylene-NR?— C(O)—O— C1-6alkyl, X2— R79; and X2—C1-6alkylene-R79;
R? is selected, independently for each occurrence, from H, methyl, ethyl, cyclopropyl, cyclobutyl, and propyl;
R? is selected, independently for each occurrence, from H, methyl, ethyl, propyl, (optionally substituted by hydroxyl), butyl (optionally substituted by hydroxyl), —C(O)-methyl and —C(O)-ethyl, or R? and R? taken together with the nitrogen to which they are attached may form a 4-7 membered heterocycle optionally substituted by one, two or more substituents selected from the group consisting of halogen, hydroxyl, NH2, —C(O)—O—C1-3alkyl, —C(O)—C1-3alkyl, carboxy, oxo, and C1-3alkyl;
each of moieties R4, R5, R6, R7, R8, R9, and R10 is independently selected for each occurrence from the group consisting of hydrogen, C1-6alkyl, C1-6alkoxy, C2-6alkynyl, C2-6alkenyl, halogen, hydroxyl, nitro, cyano, and NR?R?;
wherein for each occurrence, C1-6alkyl, C2-6alkenyl or C2-6alkynyl may be optionally substituted with one, two, three or more substituents selected from the group consisting of halogen, hydroxyl, nitro, cyano, carboxy, C3-6cycloalkyl, C2-4alkenyl, C2-4alkynyl, C1-3alkoxy, NR?R?, —NR?—S(O)w— C1-2alkyl (where w is 0, 1 or 2), NR?—C(O)—C1-3alkyl, NR?—C(O)— O—C1-3alkyl, and S(O)w—NR?R?(where w is 0, 1 or 2); C1-6alkoxy may be optionally substituted with one, two, three or more substituents selected from the group consisting of halogen, hydroxyl, nitro, cyano, carboxy, C1-3alkyl, NR?R?, —NR?—S(O)w— C1-2alkyl (where w is 0, 1 or 2), and S(O)w—NR?R? (where w is 0, 1 or 2); C1-6alkylene may be optionally substituted by a substituent selected from the group consisting of C3-6cycloalkyl, hydroxyl, cyano, and halogen;
and pharmaceutically acceptable salts and N-oxides thereof.

US Pat. No. 10,968,210

DIAMINO-ALKYLAMINO-LINKED ARYLSULFONAMIDE COMPOUNDS WITH SELECTIVE ACTIVITY IN VOLTAGE-GATED SODIUM CHANNELS

1. A compound of Formula A1, or a pharmaceutically acceptable salt thereof:
wherein:
Het1 is a five or six member heteroaryl moiety comprising up to 5 carbon atoms and one or more heteroatoms selected from N and S, which is optionally substituted on any ring carbon thereof by a halogen or methyl, which methyl may optionally be fluorine substituted, but is not selected to be a moiety of the following formula:

wherein X is —N? or —C(R18A)?, wherein R18A is H, —Cl or —F;R1A to R4A are independently —F, —Cl, —Br, —CN, —H, or a linear, branched or cyclic alkyl of up to 4 carbon atoms which may optionally be substituted on any carbon thereof with one or more fluorine, with the proviso that at least one of R1A to R4A is not —H and at least two of R1A to R4A are selected to be —H;Q1 is(a) a moiety of the formula A1-NH—X1—, wherein:X1 is:
(i) alkyl of three or four carbon atoms which is optionally substituted on one or more carbon atoms thereof with halogen, benzyl, aryl, or a linear or branched alkyl of up to 4 carbon atoms; or
(ii) a moiety of the formula:

 and
A1 is:
(i) R1b—CHR2b—, wherein
R2b is: (ai)-aryl; (aii)—CH3; (aiii)—H; or (aiv) halogen; and
R1b is:
(ai) a moiety of the formula:

 wherein n1 is 0 or 1;
(aii) a moiety of the formula:
R3bNH—CH2—(CHR4b)0-3—,
wherein:
 (ai) R3b is —H; linear or branched alkyl of up to 4 carbon, or a moiety of the formula:

 wherein the moiety is bonded via a carbon beta or gamma to the oxygen; and
 (aii) R4b is —H or —F;
(aiii) a moiety of the formula:

wherein:
 n2 is 1 or 2; and
 R5b is up to two optional substituents bonded to one or more available ring carbon atoms which are independently for each occurrence: —F; —O-aryl; aryl; —CN; —O—CH3; or

 wherein R6b is an optional substituent bonded to an available ring carbon atom which, if present, is halogen or —O—CH3; or
(aiv) aryl, which is substituted on one ring carbon atom thereof with —CH2NH2;
(ii) a moiety of the formula:

 wherein R8b is —H or aryl;
(iii) a moiety of the formula: or

 wherein n3 is 1 or 2 and m3 is 0 or 1;
(iv) adamantyl bonded to the nitrogen via any available carbon atom;(b) a moiety of the formula:
wherein R1c is a moiety of the formula:

wherein:
n4 is 1 or 2; and
R2c is up to two optional substituents which are independently for each occurrence: —F; —O-aryl; aryl; —CN; —O—CH3; or

 wherein R3c is an optional substituent bonded to an available ring carbon atom which, if present, is —O—CH3; or(c) a moiety of the formula A2-X2—, wherein:X2 is a linear or branched alkyl of three or four carbon atoms; and
A2 is:
(i) a moiety of the formula:

wherein:
n5=1-4;
R1d is —H or —CH2NH2; and
R2d and R3d are selected as follows:
 if R1d is selected to be —CH2—NH2, then for all occurrences, R2d and R3d are —H; or if R1d is —H, then at least one of R2d or R3d is: (ai) —CH2—NH2; (aii) —NH—CH3; or (aiii) —NH2, and the others of R2d and R3d are independently for each occurrence: (ai)—H; (ii) linear-, branched, or cyclic alkyl of up to 6 carbon atoms; or (aiii) aryl;
(ii) a moiety of the formula:

wherein:
n6 is 0 or 1;
if n6=0, then A3 is —(CH2)2—;
if n6=1, then A3 is a bond between the two ring carbon atoms;
(iii) a moiety of the formula:

wherein:
p=1-3;
q7 and m7 are independently=0 or 1;
n7=1 or 2;
(iv) a moiety of the formula:

wherein:
m8 and q8 are independently 1, 2 or 3;
n8 and p8 are independently 0 or 1; and
m+n?4; or
(v) a moiety of the formula:

Wherein: (i) both R1e are —H; or (ii) both R1e taken together form a bridge of the formula —(CH2)1-3.

US Pat. No. 10,968,209

TRPV4 ANTAGONIST

GlaxoSmithKline Intellect...

1. A compound which is:1-(((5S,7R)-3-(5-cyclopropylpyrazin-2-yl)-7-hydroxy-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile;

or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,208

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT COMPRISING THE SAME, AND ELECTRONIC DEVICE THEREOF

DUK SAN NEOLUX CO., LTD.,...

1. A compound of formula 1:
wherein:
R1 is

A ring is one of formulas 2 to 4,

X is —O— or —S—,
R2 to R23 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C1-C50 alkyl group, a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, a C2-C20 alkenyl group, a C1-C30 alkoxyl group and a C6-C30 aryloxy group, and neighboring groups of R6 to R23 are optionally linked to each other to form a ring,
L1 is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P,
L2 is selected from the group consisting of a C6-C60 arylene group, a fluorenylene group, and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P,
Ar1 and Are are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and -L?-N(Ra)(Rb),
in -L?-N(Ra)(Rb), L? is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a fused ring formed by a C3-C60 aliphatic ring and a C6-C60 aromatic ring, and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and Ra and Rb are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a fused ring formed by a C3-C60 aliphatic ring and a C6-C60 aromatic ring, and a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and
R1-R23, Ra, Rb, L1, L2, L?, Ar1, Ar2, and a ring formed by bonding neighboring groups of R6 to R23 to each other are each optionally further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a 06-020 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a C7-C20 arylalkyl group, and a C8-C20 arylalkenyl group.

US Pat. No. 10,968,206

CANNABINERGIC NITRATE ESTERS AND RELATED ANALOGS

Northeastern University, ...

1. A compound of formula (IIa):
or a pharmaceutically acceptable salt thereof;
wherein:
ring C is carbocyclic, bicyclic, aryl, heterocyclyl, heteroaryl, or a terpene;
G is a bond, C?O, NH, CH2, CONN, NHCO, C(O)O, OC(O), OCH2, S, SO, SO2, or O;
ring A is:

R2a and R2b are each independently H, OH, SH, NH2, CF3, COOH, alkoxy, halogen, ONO2, alkyl-ONO2, or optionally substituted alkyl, haloalkyl, amine, amide, imide, alkoxy, alkoxy thio, phosphate, phosphonate, carboxyl, formyl, carbamyl, amino, acylamino, amido, imido, aminoalkyl, aminoaryl, heteroarylamino, heterocyclylamino, sulfonate, sulfonamide, sulfonyl, thioalkyl, thioaryl, heteroarylthio, heterocyclylthio, phosphonate, phosphate, or acetate;
Y is a bond; and
R3 is alkyl,
wherein the carbocyclic, bicyclic, aryl, heterocyclyl, or heteroaryl Ring C is optionally substituted with one or more substituents selected from alkyl, alkynyl, alkenyl, alcohol, halogen, hydroxyl, alkoxy, alkenoxy, alkynoxy, aryloxy, aralkyloxy, heterocyclyloxy, heterocyclylalkoxy, oxo, carboxyl, ester, urethane, oxime, hydroxylamine, alkoxyamine, aralkoxyamine, thiol, sulfide, sulfoxide, sulfone, sulfonyl, sulfonamide, amine, N-oxide, hydrazine, hydrazide, hydrazine, azide, amide, urea, amidine, guanidine, enamine, imide, isocyanate, isothiocyanate, cyanate, thiocyanate, imine, nitro, or nitrile.

US Pat. No. 10,968,205

PYRAZOLO AND TRIAZOLO BICYCLIC COMPOUNDS AS JAK KINASE INHIBITORS

1. A method for treating celiac disease in a patient, the method comprising administering to the patient a compound of the formula:or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,204

FLAME RETARDANTS

Bruag Fire Protection AG,...

1. A water- or lacquer-based coating for a flammable material comprising 10-30% of a compound according to Formula 1:
with R=phosphite substituted with alkyl, functionalized alkyl, aryl, functionalized aryl, except halogen-substituted alkyl or aryl;
R?=alkylene, arylene, alkoxy or aryloxy, all unsubstituted or functionalized, except halogen-substituted;
X1 and X2=hetero atoms and X1 and X2 are the same or different.

US Pat. No. 10,968,203

PYRIMIDINYL-PYRIDYLOXY-NAPHTHYL COMPOUNDS AND METHODS OF TREATING IRE1-RELATED DISEASES AND DISORDERS

Genentech, Inc., South S...

1. A compound of the Formula I?:
or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, wherein:
R1 is C3-C12 cycloalkyl, C3-C12 heterocyclyl, C1-C12 heteroaryl, C6-C20 aryl, —(C1-C6 alkyldiyl)-(C3-C12 cycloalkyl), or —(C1-C6 alkyldiyl)-(C3-C12 heterocyclyl);
R2 is H, F, Cl, —CN, —OCH3, —OCH2CH3, or C1-C6 alkyl;
R3 is H, —CN, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C1-C12 heteroaryl, C6-C20 aryl, —O—(C1-C12 heteroaryl), —O—(C1-C6 alkyldiyl)-(C6-C20 aryl), —N(R8)(C1-C6 alkyl), —NR8C(O)R9, —NR8C(O)OR9, —NR8C(O)NHR9, —NR8SO2-(C1-C6 alkyl), —NR8SO2-(C2-C6 alkenyl), —NR8SO2-(C3-C12 cycloalkyl), —NR8SO2-(C1-C12 heteroaryl), —NR8SO2-(C1-C6 alkyldiyl)-(C3-C12 cycloalkyl), —NR8SO2-(C1-C6 alkyldiyl)-(C3-C12 heterocyclyl), —NR8SO2-(C1-C6 alkyldiyl)-(C1-C12 heteroaryl), —NR8SO2-(C1-C6 alkyldiyl)-(C6-C20 aryl), —NR8SO2NR8R9, or —SO2NR8R9;
R4 is H, —CN, C3-C2 cycloalkyl, C3-C12 heterocyclyl, C1-C12 heteroaryl, C6-C20 aryl, —O—(C1-C12 heteroaryl), —O—(C1-C6 alkyldiyl)-(C6-C20 aryl), —NR8R9, —NR8C(O)R9, —NR8C(O)OR9, —NR8C(O)NHR9, —NR8SO2-(C1-C6 alkyl), —NR8SO2-(C2-C6 alkenyl), —NR8SO2-(C1-C12 heteroaryl), —NR8SO2-(C3-C12 cycloalkyl), —NR8SO2-(C3-C12 heterocyclyl), —NR8SO2-(C1-C6 alkyldiyl)-(C3-C12 cycloalkyl), —NR8SO2-(C1-C6 alkyldiyl)-(C3-C12 heterocyclyl), —NR8SO2-(C1-C6 alkyldiyl)-(C1-C12 heteroaryl), —NR8SO2-(C1-C6 alkyldiyl)-(C6-C20 aryl), —NR8SO2NR8R9, or —SO2NR8R9;
each R5 and R7 are independently H, F, Cl, —CN, —CH2H, —C(O)NH2, —OH, —OCH3, —OCH2CH3, or C1-C6 alkyl;
n is 0, 1, 2, or 3;
each R6 is independently H, F, Cl, Br, I, —CN, —NO2, —O—(C1-C6 alkyl) or C1-C6 alkyl;
each R8 is independently H, or C1-C6 alkyl;
each R9 is independently C1-C6 alkyl, C2-C6 alkenyl, C3-C2 cycloalkyl, C3-C12 heterocyclyl, C1-C12 heteroaryl, C6-C20 aryl; —(C1-C6 alkyldiyl)-(C3-C12 cycloalkyl), —(C1-C6 alkyldiyl)-(C3-C2 heterocyclyl), —(C1-C6 alkyldiyl)-(C1-C6 heteroaryl), —(C1-C6 alkyldiyl)-(C6-C20 aryl), or —(C1-C6 alkyldiyl)-O—(C6-C20 aryl); and
wherein cycloalkyl, heterocyclyl, heteroaryl, aryl, alkyl, alkyldiyl, and alkenyl are optionally and independently substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, —CN, —CH3, —CH2CH3, —CH2CH2CH3, —CH(CH3)2, —CH2CH(CH3)2, —CH(CH3)CH2CH3, —CH2C(CH3)3, —CH2OH, —CH2OCH3, —CH2CH2OH, —C(CH3)2OH, —CH(OH)CH(CH3)2, —C(CH3)2CH2OH, —CH2CH2CH2OH, —CH2CH2C(CH3)2OH, —CH2CH2OCH3, —CH2CH(CH3)OCH3, —CH2CH2CH2OCH3, —CH2CH2C(CH3)2OCH3, —CH2CH2SO2CH3, —CH2OP(O)(OH)2, —CH2F, —CHF2, —CH2NH2, —CH2NHSO2CH3, —CH2NHCH3, —CH2N(CH3)2, —CF3, —CH2CF3, —CH2CHF2, —CH2CH2CHF2, —CH2CH2CF3, —CH(CH3)CN, —C(CH3)2CN, —CH2CN, —CO2H, —COCH3, —C2CH3, —CO2C(CH3)3, —COCH(OH)CH3, —CONH2, —CONHCH3, —CONHCH2CH3, —CONHCH(CH3)2, —CON(CH3)2, —C(CH3)2CONH2, —NH2, —NHCH3, —N(CH3)2, —N(CH3)CH2CH3, —NHCOCH3, —N(CH3)COCH3, —NHS(O)2CH3, —N(CH3)C(CH3)2CONH2, —N(CH3)CH2CH2S(O)2CH3, —NO2, ?O, —OH, —OCH3, —OCH2CH3, —OCH2CH2OCH3, —OCH2CH2OH, —OCH2CH2N(CH3)2, —OP(O)(OH)2, —S(O)2N(CH3)2, —SCH3, —S(O)2CH3, —S(O)3H, cyclopropyl, cyclopropylamide, cyclobutyl, oxetanyl, azetidinyl, 1-methylazetidin-3-yloxy, N-methyl-N-oxetan-3-ylamino, azetidin-1-ylmethyl, benzyloxyphenyl, pyrrolidin-1-yl, pyrrolidin-1-yl-methanone, phenyl, piperazin-1-yl, piperidin-1-yl, morpholinomethyl, morpholino-methanone, and morpholino.

US Pat. No. 10,968,202

COMPOUNDS AS NEURONAL HISTAMINE RECEPTOR-3 ANTAGONISTS AND USES THEREOF

XW LABORATORIES INC., Gr...

1. A method of treating cataplexy associated with narcolepsy in a patient comprising administering to a patient in need thereof a therapeutically effective amount of a compound having the structure:
or a pharmaceutically acceptable salt thereof, wherein,
R1 is selected from hydrogen and C1-3 alkyl; and
R2 is selected from hydrogen, hydroxyl, and C1-3 alkoxy.

US Pat. No. 10,968,201

BICYCLIC CARBOXAMIDES AND METHODS OF USE THEREOF

TEMPEST THERAPEUTICS, INC...

1. A compound of Formula (I), or a pharmaceutically acceptable salt, solvate, solvate of the salt, hydrate, a single stereoisomer, a mixture of stereoisomers, a racemic mixture of stereoisomers, isotopic variant or prodrug thereof:wherein:X1 is N;
X3 is CR3;
X4 is CR4;
X5 is CR5;
L1 is —CRb2-;
Ring A is aryl;
R1 is aryl optionally substituted with one, two, or three Ry;
each Ry is independently alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, halogen, —OR8, —NR8R9, —CN, —C(O)R11, —C(O)NR8R9, —NR8C(O)R11, —NR8C(O)OR9, —NR10C(O)NR8R9, —OC(O)NR8R9, —S(O)2R11, —S(O)R11, —S(O)2NR8R9, —S(O)NR8R9, —NR8S(O)R11, —NR8S(O)2R11, or —NR10S(O)2NR8R9; wherein the alkyl is optionally substituted with —OR8 or —NR8R9 and wherein the cycloalkyl and heterocyclyl are optionally substituted with one, two, or three groups selected from halogen, alkyl, and haloalkyl;
each Rx is independently halogen, methyl, C1haloalkyl, or —CN;
R2, R3, R4, and R5 are each independently hydrogen, alkyl, halogen, —OR8, —NR8R9, —S(O)R11, —S(O)2R11, —CN, cycloalkyl, or haloalkyl;
R6 is hydrogen, alkyl, or haloalkyl;
R7 is hydrogen, halogen, alkyl, alkoxy, haloalkoxy, hydroxyl, or haloalkyl;
each R8 and each R9 are independently hydrogen, alkyl, haloalkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein cycloalkyl, heterocyclyl, aryl, and heteroaryl are optionally substituted with one, two, or three groups selected from halogen, alkyl, and haloalkyl; or
R8 and R9, together with the atom or atoms to which they are attached, form a heterocyclyl optionally substituted with one, two, or three groups selected from halogen, alkyl, and haloalkyl;
each R10 is independently hydrogen or alkyl;
each R11 is independently alkyl, haloalkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein cycloalkyl, heterocyclyl, aryl, and heteroaryl are optionally substituted with one, two, or three groups selected from halogen, alkyl, and haloalkyl;
Y1 and Y2 are each independently a bond or —(CRa2)n—, provided that Y1 and Y2 are not both a bond;
Z1 and Z2 are each —CRa2—;
L2 is —(CRc2)m—;
G is —C(O)OR12, —C(O)NHOH, —SO3H, —SO2NH2, —SO2NHRd, —SO2NHC(O)Rd, —NHC(O)NHSO2Rd, -1H-tetrazolyl, —P(O)(OH)2, -1,2,4-oxadiazol-5(4H)-one, -tetrazol-5(4H)-one, or —C(O)NHSO2Rd;
R12 is selected from H, C1-C6 alkyl, aryl, aralkyl, CH(R13)OC(?O)R14, CH(R13)OC(?O)OR14 and a (5-alkyl-2-oxo-1,3-dioxolen-4-yl)methyl group having the following formula:
wherein Re is C1-C6 alkyl;R13 is hydrogen or C1-C6 alkyl;
R14 is C1-C6 alkyl or C3-C6-cycloalkyl;
each Ra is independently hydrogen, alkyl, halogen, or haloalkyl;
each Rb is independently hydrogen, alkyl, or haloalkyl, ortwo Rbs, together with the carbon atom to which they are attached, form a cycloalkyl or a heterocyclyl;each Rc is independently hydrogen or halogen;
Rd is alkyl, haloalkyl, cycloalkyl, aryl, or heteroaryl;
m is 0, 1, or 2;
each n is independently 1, 2, or 3;
p is 1; and
q is 0, 1, or 2.

US Pat. No. 10,968,200

SALTS OF AN LSD1 INHIBITOR AND PROCESSES FOR PREPARING THE SAME

Incyte Corporation, Wilm...

1. A salt which is a hydrochloric acid salt of a compound having the structure:

US Pat. No. 10,968,199

CYCLOALKYL-CONTAINING APOPTOSIS SIGNAL-REGULATING KINASE 1 INHIBITORS AND METHODS OF USE THEREOF

Enanta Pharmaceuticals, I...

1. A compound represented by Formula I or a pharmaceutically acceptable salt thereof:
wherein
R1 is selected from the following:

wherein R4 is selected from the group consisting of:
1) Hydrogen;
2) Optionally substituted —C1-C8 alkyl;
3) Optionally substituted —C2-C8 alkenyl;
4) Optionally substituted —C2-C8 alkynyl;
5) Optionally substituted —C3-C8 cycloalkyl;
6) Optionally substituted aryl;
7) Optionally substituted arylalkyl;
8) Optionally substituted heterocycloalkyl;
9) Optionally substituted heteroaryl; and
10) Optionally substituted heteroarylalkyl;
is selected fromwhereinX2 and X3 are each independently selected from N or C(R5);
R5 and R6 are each independently selected from the group consisting of:
1) Hydrogen;
2) Halogen;
3) —NO2;
4) Cyano;
5) Optionally substituted —C1-C8 alkyl;
6) Optionally substituted —C3-C8 cycloalkyl; and
7) Optionally substituted 3- to 8-membered heterocycloalkyl;
X1 is N or C(R11), R11is hydrogen, halogen or optionally substituted alkoxy;
is selected from —C3-C8 cycloalkyl and —C4-C8 cycloalkenyl, each of which, is optionally substituted with one or more substituents, which are not R3;R2 is selected from the group consisting of:
1) Hydrogen;
2) Halogen;
3) —NO2;
4) Cyano;
5) Optionally substituted —C1-C8 alkyl;
6) Optionally substituted —C2-C8 alkenyl;
7) Optionally substituted —C2-C8 alkynyl;
8) Optionally substituted —C3-C8 cycloalkyl;
9) Optionally substituted aryl;
10) Optionally substituted arylalkyl;
11) Optionally substituted 3- to 8-membered heterocycloalkyl;
12) Optionally substituted heteroaryl;
13) Optionally substituted heteroarylalkyl;
14) —N(R7)(R8);
15) —S(O)2N(R7)(R8);
16) —N(R7)C(O)(R8); and
17) —N(R7)S(O)2(R8);
R3 is selected from the group consisting of:
1) —NO2;
2) Cyano;
3) —N(R7)(R8);
4) —N(R9)C(O)N(R7)(R8);
5) —N(R7)C(O)(R8);
6) —N(R7)C(O)2(R8);
7) —N(R9)S(O)2N(R7)(R8);
8) —N(R7)S(O)2(R8);
9) —C(O)2(R7);
10) —C(O)N(R7)(R8);
11) —C(O)N(R7)S(O)2(R8);
12) —CH2(O)C(O)2(R7);
13) —CH2(O)C(O)N(R7)(R8);
14) Optionally substituted —C1-C8 alkyl;
15) Optionally substituted —C2-C8 alkenyl;
16) Optionally substituted —C2-C8 alkynyl;
17) Optionally substituted —C3-C8 cycloalkyl;
18) Optionally substituted aryl;
19) Optionally substituted arylalkyl;
20) Optionally substituted 3- to 8-membered heterocycloalkyl;
21) Optionally substituted heteroaryl; and
22) Optionally substituted heteroarylalkyl;
wherein R7, R8, and R9 are independently selected from the group consisting of hydrogen, —C1-C8alkyl, —C3-C8 cycloalkyl, 3- to 8-membered heterocycloalkyl, aryl, and heteroaryl, all of which are optionally substituted with 1-3 substituents selected from halo, alkyl, mono- or dialkylamino, alkyl or aryl or heteroaryl amide, —CN, alkoxy, —CF3, aryl, and heteroaryl;
alternatively, R7 and R8 are taken together with the nitrogen atom to which they are attached to form a heterocyclic.

US Pat. No. 10,968,198

BIARYLTRIAZOLE INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR

Yale University, New Hav...

1. A method of inhibiting human macrophage inhibitory factor (MIF) in a subject, the method comprising:administering to the subject an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof:
wherein:X3 is CR3 or N;
X8 is CR8 or N;
R3 is selected from the group consisting of H, halogen, C1-6 alkyl, and C1-6 haloalkyl;
R4 is selected from the group consisting of H, halogen C1-6 alkyl, and C1-6 haloalkyl;
R5, R6, R7 and R8 are each independently selected from the group consisting of H, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl—C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl—C1-4 alkylene, 4-10 membered heterocycloalkyl—C1-4 alkylene, CN, NO2, ORa1, SRa1, c(O)Rb1, C(o)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)NRc1C(O)ORa1, C(?NRc1)NRc1Rd1, NRc1C(?NRe1)NRc1Rd1, S(O)Rb1, S(O)2Rb1, NRc1S(O)2Rb1 and S(O)2NRc1Rd1;
wherein each of said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl, forming R5, R6, R7 or R8 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, NRc2Rd2 NRc2C(O)Rb2, NRc2C(O)NRc2Rd2, NRc2C(O)ORa2, C(?NRe2)NRc2Rd2, NRc2C(?NRe2)NRc2Rd2, S(O)Rb2, S(O)2Rb2, NRc2S(O)2Rb2 and S(O)2NRc2Rd2 and
wherein each of said C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl—C1-4 alkylene, C6-10 aryl—C1-4 alkylene, 5-10 membered heteroaryl—C1-4 alkylene and 4-10 membered heterocycloalkyl—C1-4 alkylene forming R5, R6, R7 or R8 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of C1-6 alkyl, halogen, C1-6 haloalkyl, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C)O)ORa2, OC(O)NRc2Rd2, NRc2Rd2, NRc2C(O)Rb2, NRc2C(O)NRc2Rd2, NRc2C(O)ORb2, OC(O)NRc2Rd2, NRc3C(?NRe2)NR c2Rd2, NRc2C(O)Rb2, NRc2C(O)NRc2Rd2, NRc2C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, NRc2C(?NRe2)NRc2Rd2, S(O)Rb2, S(O)2Rb2, NRc2S(O)2Rc2Rd2;
or any one of R5, R6, R7, and R8 may represent a group of formula Ars;
or R6 and R7 in combination with the atoms to which they are attached may form a 5-7 membered carbocyclic or heterocyclic ring that is unsubstituted or substituted by 1, 2 or 3 substituents each independently selected from R9;
or at least one of R5, R6, R7, or R8 may be each independently a water solubilizing group;
each R9 is independently selected from the group consisting of halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C14 alkylene, 4-10 membered heterocycloalkyl-C1-4 alkylene, CN, NO2, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)NRc1Rd1, NRc1C(O)ORa1, C(?NRe1)NRc1Rd1, NRc1C(?NRe1)NRc1Rd1, S(O)Rb1, S(O)2Rb1, NRc1S(O)2Rb1 and S(O)2NRc1Rd1;
wherein each of said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl forming R9 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, CN, NO2, ORa2, SRa2, C(O)Rb2, c(O)NRc2Rd2, C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, NRc2Rd2, NRc2C(O)Rb2, NRc2C(O)NRc2Rd2, NRc2C(O)ORa2, C(?NRe2)NRc2Rd2, NRc2C(?NRe2)NRc2Rd2, S(O)Rb2, NRc2S(O)2Rb2, S(O)2NRc2Rd2, S(O)2Rb2, NRc2S(O)2Rb2, S(O)2NRc2Rd2; and
wherein each of said C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene and 4-10 membered heterocycloalkyl-C1-4 alkylene forming R9 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of C1-6 alkyl, halogen, C1-6 haloalkyl, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, NRc2Rd2, NRc2C(O)Rb2, NRc2C(O)NRc2Rd2, NRc2C(O)ORa2, C(?NRe2)NRc2Rd2, NRc2C(?NRe2)NRc2Rd2, S(O)Rb2, S(O)2Rb2, NRc2S(O)2Rb2, S(O)2NRc2Rd2, and water solubilizing groups;
Y1, Y2, Y3, Y4, and Y5 are each independently selected from the group consisting of H, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl—C1-4 alkylene, 4-10 membered heterocycloalkyl—C1-4 alkylene, CN, NO2, ORa3, SRa3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)NRc3Rd3, NRc3C(O)ORa3, C(?NRc3)NRc3Rd3, NRc3C(?NRe3)NRc3Rd3, S(O)Rb3, NRc3S(O)2NRc3Rd3;
wherein each of said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl forming Y1, Y2, Y3, Y4 or Y5 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, CN, NO2, ORa4, sRa4, c(O)Rb4, c(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4c(O)Rb4, NRc4c(O)NRc4Rd4, NRc4C(O)ORa4, C(?NRc4)NRc4Rd4, NRc4C(?NRc4)NRc4Rd4, S(O)Rb4, S(O)2Rb4, NRc4D(O)Rb4and S(O)2NRc4Rd4; and
wherein each of said C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene and 4-10 membered heterocycloalkyl-C1-4 alkylene forming Y1, Y2, Y3, Y4 or Y5 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of C1-6 alkyl, halogen, C1-6 haloalkyl, CN, NO2, ORa4, SRa4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4C(O)Rb4, NRc4C(O)NRc4Rd4, NRc4C(O)ORa4, C(?NRc4)NRc4Rd4, NRc4C(?NRc4)NRc4Rd4, S(O)Rb4, S(O)2Rb4, NRc4S(O)2Rb4 and S(O)2NRc4Rd4; or
Y3 is NH, and Y2 and Y3 or Y3 and Y4, in combination with the carbon atoms to which they are attached, forms a 5-membered fused heteroaromatic ring that is unsubstituted or substituted by 1 or 2 substituents independently selected from Y6;
each Y6 is independently selected from the group consisting of halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, 4-10 membered heterocycloalkyl-C1-4 alkylene, CN, NO2, ORa3, SRa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)NRc3Rd3, NRc3C(O)ORa3, C(?NRc3)NRc3Rd3, NRc3C(?NRc3)NRc3Rd3, S(O)Rb3, S(O)2Rb3, NRc3S(O)2Rb3 and S(O)2NRc1Rd1;
wherein each of said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl forming Y6 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, CN, NO2, ORa4, SRa4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4C(O)Rb4, NRc4C(O)NRc4Rd4, NRc4C(O)ORd1, C(?NRc4)NRc4Rd4, NRc4C(?NRe4)NRc4Rd4, S(O)Rb4, NRc4S(O)2Rb4 and S(O)2NRc4Rd4; and
wherein each of said C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene and 4-10 membered heterocycloalkyl-C1-4 alkylene forming Y6 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of C1-6 alkyl, halogen, C1-6 haloalkyl, CN, NO2, ORa4, SRa4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4 NRc4C(O)Rb4, NRc4C(O)NRc4Rd4, NRc4C(O)ORa4, C(?NRe4)NRc4Rd4, S(O)Rb4, S(O)2Rb4, NRc4S(O)2Rb4 and S(O)2NRc4Rd4;
each Ars is:

A1 is N or CZ1;
A2 is N or CZ2;
A3 is N or CZ3;
A4 is N or CZ4;
A5 is N or CZ5;
provided that 0, 1 or 2 of Z1, Z2, Z3, Z4, and Z5 are nitrogen;
Z1, Z2, Z3, Z4, and Z5 are each independently selected from the group consisting of H, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, 4-10 membered heterocycloalkyl-C1-4 alkylene, CN, NO2, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(?NRe5)NRc5Rd5, NRc5C(?NRe5)NRc5Rd5, S(O)Rb5, S(O)2Rb5, NRc5S(O)2Rb5 and S(O)2NRc5Rd5;
wherein each of said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl forming Z1, Z2, Z3, Z4, or Z5 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, CN, NO2, ORa6, SRa6, C(O)Rb6, C(O)NRc6Rd6, C(O)ORa6, OC(O)Rb6, OC(O)NRc6Rd6, NRc6Rd6, NRc6C(O)Rb6, NRc6C(O)NRc6Rd6, NRc6C(O)ORa6, C(?NRe6)NRc6Rd6, NRc6C(?nre6)NRc6Rd6, S(O)Rb6, S(O)2Rb6, NRc6S(O)Rb6and S(O)2NRc6Rd6; and
wherein each of said C3-7 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C3-7 cycloalkyl-C1-4 alkylene, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene and 4-10 membered heterocycloalkyl-C1-4 alkylene forming Z1, Z2, Z3, Z4, or Z5 is independently unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of C1-6 alkyl, halogen, C1-6 haloalkyl, CN, NO2, ORa6, SRa6, C(O)Rb6, C(O)NRc6Rd6, C(O)ORa6, OC(O)Rb6, OC(O)NRc6Rd6, NRc6Rd6, NCc6C(O)Rb6, NRc6C(O)NRc6Rd6, NRc6C(O)ORa6, C(?NRe6)NRc6Rd6, NRc6C(?NRe6)NRc6Rd6, S(O)Rb6, S(O)2Rb6, NRc6S(O)2Rb6 and S(O)2NRc6Rd6;
or wherein any one or two of Z1, Z2, Z3, Z4, and Z5 is independently selected from water solubilizing groups;
provided that at least one of R5, R6, R7, R8, Z1, and Z2 is a water solubilizing group;
Ls is a bond, O NRc6, C1-4alkylene, C(O), NRc6C(O) or C(O)NRc6;
Ra1, Rb1, Ra2, Rb2, Ra3, Rb3, Ra4, Rb4, Ra5, Rb5, Ra6 and Rb6 are each independently selected from the group consisting of hydrogen, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 5-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, 5-10 membered heterocycloalkyl-C1-4 alkylene, and C1-4 alkoxy-C1-4 alkylene, wherein each of said C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, and C1-4 alkoxy-C1-4 alkylene forming Ra1, Rb1, Ra2, Rb2, Ra3, Rb3, Ra4, Rb4, Ra5, Rb5, Ra6 or Rb6 is independently unsubstituted or substituted by 1, 2, 3, 4 or 5 groups independently selected from halogen, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7, C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rab, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7 and S(O)2NRc7Rd7 and wherein said C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 5-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, and 5-10 membered heterocycloalkyl-C1-4 alkylene, forming Ra1, Rb1, Ra2, Rb2, Ra3, Rb3, Ra4 or Rb4 is indpendently unsubstituded or substituted by 1, 2, 3, 4 or 5 groups independently selected from C1-6 alkyl, halogen, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7 and S(O)2NRc7Rd7;
Rc1, Rd1, Rc2, Rd2, Rc3, Rd3, Rc4, Rd4, Rc5, Rd5, Rc6, and Rd6 are each independently selected from the group consisting of hydrogen, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 5-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, 5-10 membered heterocycloalkyl-C1-4 alkylene, and C1-4 alkoxy-C1-4 alkylene, wherein each of said C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, and C1-4 alkoxy-C1-4 alkylene forming Rc1, Rd1, Rc2, Rd2, Rc3, Rd3, Rc4, Rd4, Rc5, Rd5, Rc6, or Rd6 is independently unsubstituted or substituted by 1, 2, 3, 4 or 5 groups independently selected from the group consisting of halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O) NRc7Rd7, NRc7Rd7, NRc7C(O)R b7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7 and S(O)2NRc7Rd7 and
wherein each of said C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 5-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, and 5-10 membered heterocycloalkyl-C1-4 alkylene, forming Rc1, Rd1, Rc2, Rd2, Rc3, Rd3, Rc4, Rd4, Rc5, Rd5, Rc6 or Rd6 is independently unsubstituted or substituted by 1, 2, 3, 4 or 5 groups independently selected from the group consisting of C1-6 alkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7 and S(O)s NRc7Rd7;
or Rc1 and Rd1, Rc2 and Rd2, Rc3 and Rd3, Rc4 and Rd4, Rc5 and Rd5, or Rc6 and Rd6, attached to the same N atom, together with the N atom to which they are both attached, form a 4-, 5-, 6-or 7-membered heterocycloalkyl group or 5-membered heteroaryl group, each optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of C1-6 alkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7 and S(O)2NRc7Rd7;
Ra7, Rb7, Rc7 and Rd7 are each independently selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene and 4-10 membered heterocycloalkyl-C1-3 alkylene,
wherein said C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene and 4-10 membered heterocycloalkyl-C1-3 alkylene forming Ra7, Rb7, Rc7 and Rd7 are each optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of OH, CN, amino, NH(C1-6alkyl), N(C1-6alkyl)2, halo, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl and C1-6 haloalkoxy;
or Rc7 and Rd7 attached to the same N atom, together with the N atom to which they are both attached, form a 4-, 5-, 6- or 7-membered heterocycloalkyl group or 5-membered heteroaryl group, each optionally substituted with 1, 2 or 3 substituents independently selected from OH, CN, amino, NH(C1-6alkyl), N(C1-6alkyl)2, halo, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl and C1-6 haloalkoxy; and
Re1, Re2, Re3, Re4, Re5, Re6 and Re7 are each independently selected from the group consisting of H, C1-4 alkyl, OH, and C1-4 alkoxy;
each water solubilizing group is independently selected from the group consisting of -Lw-ORaw, -Lw-C(O)RbW, -Lw-C(O)NRcWRdw, -Lw-C(O)ORaW, -Lw-OC(O)Rbw, -Lw-OC(O)NRcWRdw, -Lw-NRcwRdw, -Lw-NRcwC(O)Rbw, -Lw-NRcwC(O)NRcwRdw, -Lw-NRcWC(O)ORaw, -Lw-C(?NRew)NRcWRdw, -Lw-NRcWC(?NRew)NRcwRdw, -Lw-S(O)2Raw, -Lw-NRcWS(O)2Rbw, -Lw-S(O)2NRcwRdw, —P(?O)(ORaw)2, —OP(?O)(ORaw)2, —OP(?O)(ORaw)—OP(?O)(ORaw)2, —OP(?O)(ORaw)—OP(?O)(ORaw)— OP(?O)(ORaw)2, and -Lw-Cyw; wherein:
each CyW is unsubstituted 5-10 membered heteroaryl or 4-10 membered heterocycloalkyl, or 5-10 membered heteroaryl or 4-10 membered heterocycloalkyl substituted with one or more (e.g., 1, 2, 3, 4 or 5) substituents each independently selected from C1-6 alkyl, halogen, C1-6 haloalkyl, CN, NO2, ORaw, SRaW, C(O)Rbw, C(O)NRcwRdw, C(O)ORaw, OC(O)Rbw, OC(O)NRcwRdw, NRcwRdw, NRcwC(O)Rbw, NRcwC(O)NRcwRdw, NRcwC(O)ORaw, C(?NRew)NRcwRdw, NRcwC(?NRew)NRcwRdw, S(O)Rbw, S(O)2Rbw, NRcwS(O)2Rbw and S(O)2NRcWRdw;
each -Lw- is a bond or a linking group selected from groups of the formula -Lw1-Lw2-;
the group -Lw1- is attached to the core molecule and is selected from a bond and groups of the formula —O—, —S—, —S(O)—, —S(O)2—, —C(O)—, —NH—, —NRcW, —NRcWC(O)—, —C(O)NRcw—, —O(CO)—, —C(O)O—, O(CO)NRcW—, —NRcWC(O)O—, —O(CO)O—, and —NRcwC(O)NRcw—;
the group -Lw2- is selected from a bond, unsubstituted-C1-10 alkylene-, unsubstituted-C1-10 heteroalkylene, and —C1-10 alkylene and —C1-10 heteroalkylene substituted with one or more (e.g., 1, 2, 3, 4 or 5 substituents) independently selected from the group consisting of H, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, CN, NO2, ORaw, SRaW, C(O)Rbw, C(O)NRcwRdw, C(O)ORaw, OC(O)Rbw, OC(O)NRcwRdw, NRcwRdw, NRcwC(O)Rbw, NRcwC(O)NRcwRdw, NRcwC(O)ORaw, C(?NRew)NRcwRdw, NRcwC(?NRew)NRcwRdw, S(O)Rbw, S(O)2Rbw, NRcwS(O)2Rbw, S(O)2NRcwRdw; —P(?O)(ORaw)2, —OP(?O)(ORaw)2, —OP(?O)(ORaw)—OP(?O)(ORaw)2, —OP(?O)(ORaw)—OP(?O)(ORaw)—OP(?O)(ORaw)2, oxo and sulfido;
RaW, RbW, RcW, and RdW are each independently selected from the group consisting of hydrogen, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 5-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, 5-10 membered heterocycloalkyl-C1-4 alkylene, and C1-4 alkoxy-C1-4 alkylene, wherein said C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, and C1-4 alkoxy-C1-4 alkylene forming Raw, RbW, RcW, or RdW are each optionally substituted by 1, 2, 3, 4 or 5 groups independently selected from halo, CN, ORaw*, SRaw*, C(O)Rbw*, C(O)NRcw*Rdw*, C(O)ORaw*, OC(O)Rbw*, OC(O)NRcw*Rdw*, NRcw*Rdw*, NRcw*C(O)Rbw*, NRcw*C(O)NRcw*Rdw*, NRcw*C(O)ORaW*, C(?NReW)NRcW*RdW*, NRcw*C(?NRew*)NRcw*Rdw*, S(O)Rbw*, S(O)NRcw*Rdw*, S(O)2Rbw*, NRcw*S(O)2Rbw*and S(O)2NRcw*Rdw*and wherein said C6-10 aryl, 5-10 membered heteroaryl, C3-7 cycloalkyl, 5-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkylene, C3-7 cycloalkyl-C1-4 alkylene, 5-10 membered heteroaryl-C1-4 alkylene, and 5-10 membered heterocycloalkyl-C1-4 alkylene, forming Raw, RbW, RcW, or RdW are each optionally substituted by 1, 2, 3, 4 or 5 groups independently selected from C1-6 alkyl, halo, CN, ORaW*, SRaw*, C(O)RbW*, C(O)NRcW*RdW*, C(O)ORaW*, OC(O)Rbw*, OC(O)NRcw*Rdw*, NRcw*Rdw*, NRcw*C(O)Rbw*, NRcw*C(O)NRcw*Rdw*, NRcw*C(O)ORaw*, C(?NReW*)NRcw*Rdw*, NRcw*C(?NRew*)NRcw*Rdw*, S(O)Rbw*, S(O)NRcw*Rdw*, S(O)2Rbw*, NRcw*S(O)2Rbw*and S(O)2NRcw*Rdw*;
or Rcw and Rdw, attached to the same N atom, together with the N atom to which they are both attached, form a 4-, 5-, 6- or 7-membered heterocycloalkyl group or 5-membered heteroaryl group, each optionally substituted with 1, 2 or 3 substituents independently selected from C1-6 alkyl, halo, CN, ORaw*, SRaw*, C(O)Rbw*, C(O)NRcw*Rdw*, C(O)ORaw*, OC(O)Rbw*, OC(O)NRcw*Rdw*, NRcw*Rdw*, NRcw*C(O)Rbw*, NRcw*C(O)NRcw*Rdw*, NRcw*C(O)ORaw*, C(?NRew*)NRcw*Rdw*, NRcw*C(?NRew*)NRcw*Rdw*, S(O)Rbw*, S(O)NRcw*Rdw*, S(O)2Rbw*, NRcw*S(O)2Rbw*and S(O)2NRcw*Rdw*;
RaW*, RbW*, RcW*and RdW*are each independently selected from H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, C6-10 aryl-C1-3 alkyl, 5-10 membered heteroaryl-C1-3 alkyl, C3-7 cycloalkyl-C1-3 alkyl and 4-10 membered heterocycloalkyl-C1-3 alkyl, wherein said C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl C6-10 aryl-C1-3 alkyl, 5-10 membered heteroaryl-C1-3 alkyl, C3-7 cycloalkyl-C1-3 alkyl and 4-10 membered heterocycloalkyl-C1-3 alkyl forming RaW*, RbW*, RcW*and Rdw*are each optionally substituted with 1, 2 or 3 substituents independently selected from OH, CN, amino, NH(C1-6alkyl), N(C1-6alkyl)2, halo, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl and C1-6 haloalkoxy;
or RcW*and Rdw*attached to the same N atom, together with the N atom to which they are both attached, form a 4-, 5-, 6- or 7-membered heterocycloalkyl group or 5-membered heteroaryl group, each optionally substituted with 1, 2 or 3 substituents independently selected from OH, CN, amino, NH(C1-6alkyl), N(C1-6alkyl)2, halo, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl and C1-6 haloalkoxy;
RcW and ReW*are each independently selected from H, C1-4 alkyl, OH, and C1-4 alkoxy; and
with the proviso that when Y1, Y2, Y4, Y5, and R4 are each H, Y3 is F, and X3 is H or C1-6 alkyl, then at least one of R5, R6, and R7 is not H.

US Pat. No. 10,968,197

PHOTOINITIATORS WITH PROTECTED CARBONYL GROUP

3M Innovative Properties ...

1. A protected photoinitiator of the formula:
wherein,
Aryl1 is an aromatic or heteroaromatic ring;
Aryl2 is an aromatic ring;
each R1 is an alkyl, an aryl, an electron donating group or an electron withdrawing group, and subscript a is 0 to 3;
each R2 is an alkyl, an aryl, an electron donating group or an electron withdrawing group, and subscript b is 0 to 3;
Prot is a protected carbonyl group.

US Pat. No. 10,968,196

SUBSTITUTED ?-LAPACHONES FOR TREATING CANCER

8. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and the compound of claim 1, or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,194

EQUIPMENT AND METHOD FOR CONTINUOUSLY PROCESSING PLANT MATERIAL

DELTA SEPARATIONS, LLC, ...

1. A system for separating trichomes from plant material, the system comprising:a metered feed system configured to mix the plant material with a fluid to form a slurry;
a turbulent processor comprising a shear blender and configured to receive and agitate the slurry between rotating and static teeth and shear the trichomes from the plant material to form a mixture of the fluid, the trichomes and the plant material;
a coarse filter configured to remove some of the plant material from the mixture to form an interim mixture; and
a second filter is configured to remove other plant material from the interim mixture and form a resultant mixture comprising the fluid and the trichomes.

US Pat. No. 10,968,193

ANTIDIABETIC BICYCLIC COMPOUNDS

1. A compound of structural formula I:
or a pharmaceutically acceptable salt thereof; wherein
“a” is a single bond;
Y is —CRgRg;
T is CH;
U is CR1;
V is CR2;
W is CH;
A is selected from the group consisting of:
(1) aryl, and
(2) heteroaryl,
wherein each aryl and heteroaryl is unsubstituted or substituted with one to five substituents selected from Ra;
B is selected from the group consisting of:
(1) aryl, and
(2) heteroaryl,
wherein each aryl and heteroaryl is unsubstituted or substituted with one to five substituents selected from Rb;
R1 and R2 are each independently selected from:
(1) hydrogen, and
(2) C1-6alkyl,
wherein alkyl is unsubstituted or substituted with one to three substituents selected from RL, and wherein one of R1 and R2 is C1-6alkyl substituted with R7, or R1 and R2 together with the atom(s) to which they are attached form a C3-6cycloalkyl ring or a C2-5cycloheteroalkyl ring containing 0-2 additional heteroatoms independently selected from oxygen, sulfur and N—Rg, wherein each R1 and R2 is unsubstituted or substituted with one to three substituents selected from RL, and wherein one of R1 and R2 is substituted with R7;
R3 is absent or when present is selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) —ORe,
(4) —CN,
(5) —C1-6alkyl,
(6) —C3-6cycloalkyl, and
(7) C3-6cycloalkyl-C1-3alkyl-,
wherein each alkyl and cycloalkyl is unsubstituted or substituted with one to three substituents selected from Ri;
R4 is selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) ORe,
(4) C1-6alkyl,
(5) C1-6alkyl-O—,
(6) C3-6cycloalkyl,
(7) C3-6cycloalkyl-O—,
(8) C3-6cycloalkyl-C1-10alkyl-,
(9) C3-6cycloalkyl-C1-10alkyl-O—,
(10) C2-5cycloheteroalkyl,
(11) C2-5cycloheteroalkyl-O—,
(12) C2-5cycloheteroalkyl-C1-10alkyl-,
(13) C2-5cycloheteroalkyl-C1-10alkyl-O—,
(14) aryl,
(15) aryl-O—,
(16) aryl-C1-10alkyl-,
(17) heteroaryl,
(18) heteroaryl-O—, and
(19) heteroaryl-C1-10alkyl-,
wherein each alkyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with one to three substituents selected from Rj;
R5 is selected from the group consisting of:
(1) hydrogen,
(2) —C1-6alkyl, and
(3) —C3-6cycloalkyl,
wherein each alkyl and cycloalkyl is unsubstituted or substituted with one to three substituents selected from Rj;
R6 is selected from the group consisting of:
(1) hydrogen,
(2) —C1-6alkyl, and
(3) —C3-6cycloalkyl,
wherein each alkyl and cycloalkyl is unsubstituted or substituted with one to three substituents selected from Rj;
R7 is selected from the group consisting of:
(1) —CO2R8,
(2) —C1-6alkyl-CO2R8,
(3) —C1-6alkyl-CONHSO2Rm,
(4) —C1-6alkyl-SO2NHCORm,
(5) —C1-6alkyl-tetrazolyl, and
(6) a cycloheteroalkyl selected from the group consisting of:

R8 is selected from the group consisting of:
(1) hydrogen,
(2) —C1-6alkyl,
(3) —C3-6cycloalkyl, and
(4) aryl-C1-6alkyl,
wherein each alkyl, cycloalkyl and aryl is unsubstituted or substituted with one to three substituents selected from Rj;
R9 is selected from the group consisting of:
(1) —C1-6alkyl-NRcRd, and
(2) —C1-6alkyl-C2-5cycloheteroalkyl,
wherein each alkyl and cycloheteroalkyl is unsubstituted or substituted with one to five substituents independently selected from: —C1-6alkyl, halogen, OH, —O—C1-6alkyl, —S(O)2—C1-4alkyl, —CN, —OCHF2, —OCF3, —CF3, and —C0-6alkyl-NRcRd;
Ra is selected from the group consisting of:
(1) —C1-6alkyl,
(2) halogen,
(3) —C0-6alkyl-ORe,
(4) —C0-6alkyl-NRcS(O)nRe,
(5) —C0-6alkyl-S(O)nRe,
(6) —C0-6alkyl-S(O)nNRcRd,
(7) —C0-6alkyl-NRcRd,
(8) —C0-6alkyl-C(O)Re,
(9) —C0-6alkyl-OC(O)Re,
(10) —C0-6alkyl-CO2Re,
(11) —C0-6alkyl-CN,
(12) —C0-6alkyl-C(O)NRcRd,
(13) —C0-6alkyl-NRcC(O)Re,
(14) —C0-6alkyl-NRcC(O)ORe,
(15) —C0-6alkyl-NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C0-6alkyl-aryl,
(20) —C0-6alkyl-heteroaryl,
(21) —C0-6alkyl-C3-10cycloalkyl,
(22) —C0-6alkyl —C3-10cycloalkenyl, and
(23) —C0-6alkyl-C2-10cycloheteroalkyl,
wherein each alkyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with one to five substituents independently selected from: —C1-6alkyl, halogen, OH, —O—C1-6alkyl, —S(O)2—C1-4alkyl, —CN, —OCHF2, —OCF3, —CF3, and —C0-6alkyl-NRcRd;
Rb is independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) —C2-10alkenyl,
(3) —CF3,
(4) halogen,
(5) —CN,
(6) —OH,
(7) —OC1-10alkyl,
(8) —OC2-10alkenyl,
(9) —O(CH2)pOC1-10alkyl,
(10) —O(CH2)pC3-6cycloalkyl,
(11) —O(CH2)pC3-6 cycloalkyl-C1-10alkyl,
(12) —O(CH2)pC2-5cycloheteroalkyl,
(13) —O(CH2)pC2-5cycloheteroalkyl-C1-10alkyl,
(14) —O-aryl,
(15) —O-heteroaryl,
(16) —O-aryl-C1-10alkyl,
(17) —O-heteroaryl-C1-10alkyl,
(18) —O(CH2)pNRcS(O)mRe,
(19) —O(CH2)pS(O)mRe,
(20) —O(CH2)pS(O)mNRcRd,
(21) —O(CH2)pNRcRd,
(22) —C(O)Re,
(23) —OC(O)Re,
(24) —CO2Re,
(25) —C(O)NRcRd,
(26) —NRcC(O)Re,
(27) —NRcC(O)ORe,
(28) —NRcC(O)NRcRd,
(29) —O(CH2)pO—C3-6cycloalkyl,
(30) —O(CH2)pO—C2-5cycloheteroalkyl,
(31) —OCF3,
(32) —OCHF2,
(33) —(CH2)pC3-6cycloalkyl,
(34) —(CH2)pC2-5cycloheteroalkyl,
(35) aryl,
(36) heteroaryl,
(37) aryl-C1-10alkyl-, and
(38) heteroaryl-C1-10alkyl-,
wherein each CH, CH2, alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with one to five substituents selected from —C1-6alkyl, halogen, —O—C1-6alkyl and —CF3;
Rc and Rd are each independently selected from the group consisting of:
(1) hydrogen,
(2) C1-10alkyl,
(3) C2-10alkenyl,
(4) C3-6cycloalkyl,
(5) C3-6 cycloalkyl-C1-10alkyl-,
(6) C2-5cycloheteroalkyl,
(7) C2-5cycloheteroalkyl-C1-10alkyl-,
(8) aryl,
(9) heteroaryl,
(10) aryl-C1-10alkyl-, and
(11) heteroaryl-C1-10alkyl-,
wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with one to three substituents independently selected from Rf,
or Rc and Rd together with the atom(s) to which they are attached form a C2-10 cycloheteroalkyl ring containing 0-2 additional heteroatoms independently selected from oxygen, sulfur and N—Rg, wherein each Rc and Rd is unsubstituted or substituted with one to three substituents independently selected from Rf;
each Re is independently selected from the group consisting of:
(1) hydrogen,
(2) —C1-10alkyl,
(3) —C2-10 alkenyl,
(4) —C3-6 cycloalkyl,
(5) C3-6 cycloalkyl-C1-10alkyl-,
(6) —C2-5cycloheteroalkyl,
(7) C2-5cycloheteroalkyl-C1-10alkyl-,
(8) aryl,
(9) aryl-C1-10alkyl-,
(10) heteroaryl, and
(11) heteroaryl-C1-10alkyl-,
wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with one to three substituents selected from Rh;
each Rf is selected from the group consisting of:
(1) halogen,
(2) —C1-10alkyl,
(3) —C0-6alkyl —OH,
(4) —O—C1-6alkyl,
(5) oxo,
(6) —S(O)m—C1-4alkyl,
(7) —CN,
(8) —CF3,
(9) —OCHF2, and
(10) —OCF3,
wherein each alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, halogen, C1-6alkyl, cyano and S(O)2C1-6alkyl;
each Rg is selected from the group consisting of:
(1) hydrogen,
(2) —C(O)Re, and
(3) —C1-10alkyl,
wherein alkyl is unsubstituted or substituted with one to five halogens;
each Rh is selected from the group consisting of:
(1) halogen,
(2) C1-10alkyl,
(3) —OH,
(4) —O—C1-4alkyl,
(5) —S(O)m—C1-4alkyl,
(6) —CN,
(7) —CF3,
(8) —OCHF2, and
(9) —OCF3,
wherein each alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, halogen, C1-6alkyl, cyano and —S(O)2C1-6alkyl;
Ri is selected from the group consisting of:
(1) —C1-6alkyl,
(2) —ORe,
(3) —NRcS(O)mRe,
(4) halogen,
(5) —S(O)mRe,
(6) —S(O)mNRcRd,
(7) —NRcRd,
(8) —C(O)Re,
(9) —OC(O)Re,
(10) —CO2Re,
(11) —CN,
(12) —C(O)NRcRd,
(13) —NRcC(O)Re,
(14) —NRcC(O)ORe,
(15) —NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C3-6cycloalkyl, and
(20) —C2-5cycloheteroalkyl;
each Rj is selected from the group consisting of:
(1) —C1-6alkyl,
(2) —ORe,
(3) —NRcS(O)mRe,
(4) halogen,
(5) —S(O)mRe,
(6) —S(O)mNRcRd,
(7) —NRcRd,
(8) —C(O)Re,
(9) —OC(O)Re,
(10) —CO2Re,
(11) —CN,
(12) —C(O)NRcRd,
(13) —NRcC(O)Re,
(14) —NRcC(O)ORe,
(15) —NRcC(O)NRcRd,
(16) —CF3,
(17) —OCF3,
(18) —OCHF2,
(19) —C3-6cycloalkyl, and
(20) —C2-5cycloheteroalkyl;
Rk is selected from the group consisting of:
(1) hydrogen,
(2) —C1-6 alkyl,
(3) —C1-6alkyl-SO2C1-6alkyl,
(4) —CF3, and
(5) —CHF2,
wherein each alkyl is unsubstituted or substituted with one to three substituents independently selected from: —OH, —OC1-6alkyl, halogen, cyano, and —S(O)2C1-6alkyl;
each RL is independently selected from the group consisting of:
(1) —CO2C1-6alkyl,
(2) —C1-10alkyl,
(3) —C2-10 alkenyl,
(4) —C2-10alkynyl,
(5) —C3-6cycloalkyl,
(6) —C2-6cycloheteroalkyl,
(7) aryl, and
(8) heteroaryl,
wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl and heteroaryl is unsubstituted or substituted with 1-4 substituents selected from C1-6alkyl, halogen, and —OC1-6alkyl;
each Rm is independently selected from the group consisting of:
(1) —C1-10alkyl,
(2) —C2-10 alkenyl,
(3) —C3-6 cycloalkyl,
(4) C3-6 cycloalkyl-C1-10alkyl-,
(5) —C2-5cycloheteroalkyl,
(6) C2-5cycloheteroalkyl-C1-10alkyl-,
(7) aryl,
(8) heteroaryl,
(9) aryl-C1-10alkyl-, and
(10) heteroaryl-C1-10alkyl-;
each n is independently selected from: 0, 1 or 2;
each m is independently selected from: 0, 1 or 2;
each p is independently selected from: 0, 1, 2, 3, 4, 5 or 6; and
each r is independently selected from: 0, 1, 2 or 3.

US Pat. No. 10,968,192

CRYSTALLINE SOLID FORMS OF N-(1-((2-(DIMETHYLAMINO)ETHYL)AMINO)-2-METHYL-1-OXOPROPAN-2-YL)-4-(4-(2-METHYL-5-((2S,3R,4R,5S,6R)-3,4,5-TRIHYDROXY-6-(METHYLTHIO)TETRAHYDRO-2H-PYRAN-2-YL)BENZYL)PHENYL)BUTANAMIDE AND METHODS OF THEIR SYNTHESIS

Lexicon Pharmaceuticals, ...

1. A crystalline form of N-(1-((2-(dimethylamino)ethyl)-amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)butanamide L-proline:

US Pat. No. 10,968,190

PROCESSES FOR PREPARING OXATHIAZIN-LIKE COMPOUNDS

GEISTLICH PHARMA AG, Wol...

1. A method for producing compound 2260 comprising the following reaction:

US Pat. No. 10,968,189

METHOD FOR PRODUCING 2-HYDRAZINOBENZOTHIAZOLE DERIVATIVE

DIC CORPORATION, Tokyo (...

1. A method for producing a compound represented by general formula (I) below, the method comprising:a first step of obtaining a compound represented by general formula (I-C) by reacting a compound represented by general formula (I-B) below with a compound represented by general formula (I-A) below in the presence of at least one compound selected from the group consisting of lithium amide, sodium amide, magnesium amide, potassium amide, calcium amide, cesium amide, lithium diisopropylamide, lithium hydride, sodium hydride, magnesium hydride, potassium hydride, calcium hydride, cesium hydride, lithium aluminum hydride, lithium borohydride, lithium methoxide, sodium methoxide, magnesium methoxide, potassium methoxide, calcium methoxide, cesium methoxide, lithium ethoxide, sodium ethoxide, magnesium ethoxide, potassium ethoxide, calcium ethoxide, cesium ethoxide, lithium propoxide, sodium propoxide, magnesium propoxide, potassium propoxide, calcium propoxide, cesium propoxide, lithium isopropoxide, sodium isopropoxide, magnesium isopropoxide, potassium isopropoxide, calcium isopropoxide, cesium isopropoxide, lithium butoxide, sodium butoxide, magnesium butoxide, potassium butoxide, calcium butoxide, cesium butoxide, lithium tert-butoxide, sodium tert-butoxide, magnesium tert-butoxide, potassium tert-butoxide, calcium tert-butoxide, cesium tert-butoxide, methyl lithium, ethyl lithium, propyl lithium, butyl lithium, sec-butyl lithium, tert-butyl lithium, pentyl lithium, hexyl lithium, and phenyl lithium; and
a second step of obtaining a compound represented by general formula (I) by reacting the compound represented by general formula (I-C) obtained in the first step with a compound represented by general formula (I-D) below:

where r represents an integer of 0 to 4, LW1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH2— or two or more non-adjacent —CH2— may each independently be substituted with —O—, —S—, —CH?CH—, —CF?CF—, or —C?C—, any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and when there are more than one LW1, they may be the same or different,
W2-LG2   (I-A)
where W2 represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH2— or two or more non-adjacent —CH2— may each independently be substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —CH?CH—, —CF?CF—, or —C?C—, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or W2 may represent a group represented by PW—(SpW—XW)kW—, where: PW Represents a Polymerizable Group; SpW represents a spacer group; when there are more than one SpW, they may be the same or different; XW represents —O—, —S—, —OCH2—, —CH2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH?CH—, —N?N—, —CH?N—N?CH—, —CF?CF—, —C?C—, or a single bond; when there are more than one XW, they may be the same or different, however, PW—(SpW—XW)kW— does not contain an —O—O— bond; and kW represents an integer of 0 to 10, andLG2 represents a leaving group,
where, W2, r, and LW1 are the same as those described above,
where R1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which any hydrogen atom may be substituted with a fluorine atom, and one —CH2— or two or more non-adjacent —CH2— may each independently be substituted with —O—, —S—, —OCH2—, —CH2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH?CH—, —N?N—, —CH?N—N?CH—, —CF?CF—, or —C?C—; or R1 represents a group represented by P1—(Sp1-X1)k1— where: P1 represents a polymerizable group; Sp1 represents a spacer group; when there are more than one Sp1, they may be the same or different; X1 represents —O—, —S—, —OCH2—, —CH2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH?CH—, —N?N—, —CH?N—N?CH—, —CF?CF—, —C?C—, or a single bond; when there are more than one X1, they may be the same or different; and k1 represents an integer of 0 to 10,R2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which any hydrogen atom may be substituted with a fluorine atom and one —CH2— or two or more non-adjacent —CH2— may each independently be substituted with —O—, —S—, —OCH2—, —CH2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH?CH—, —N?N—, —CH?N—N?CH—, —CF?CF—, or —C?C—; or R2 represents a group represented by —(X2—Sp2)k2—P2 where: P2 represents a polymerizable group; Sp2 represents a spacer group; when there are more than one Sp2, they may be the same or different; X2 represents —O—, —S—, —OCH2—, —CH2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH?CH—, —N?N—, —CH?N—N?CH—, —CF?CF—, —C?C—, or a single bond; when there are more than one X2, they may be the same or different; and k2 represents an integer of 0 to 10,A1 and A2 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted with one or more substituents L; when there are more than one A1, they may be the same or different; when there are more than one A2, they may be the same or different; and L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH2— or two or more non-adjacent —CH2— may each independently be substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —CH?CH—, —CF?CF—, or —C?C— and any hydrogen atom in the alkyl group may be substituted with a fluorine atom; or L may represent a group represented by PL—(SpL—XL)kL—, where: PL represents a polymerizable group; SpL represents a spacer group; when there are more than one SpL, they may be the same or different; XL represents —O—, —S—, —OCH2—, —CH2O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH?CH—OCO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH?CH—, —N?N—, —CH?N—N?CH—, —CF?CF—, —C?C—, or a single bond; when there are more than one XL, they may be the same or different; kL represents an integer of 0 to 10; and when there are more than one kL in the compound, they may be the same or different,Z1 and Z2 each independently represent —O—, —S—, —OCH2—, —CH2O—, —CH2CH2—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH?CH—, —N?N—, —CH?N—, —N?CH—, —CH?N—N?CH—, —CF?CF—, or a single bond; when there are more than one Z1, they may be the same or different; when there are more than one Z2, they may be the same or different; m1 and m2 each independently represent an integer of 1 to 6 and m1+m2 is an integer of 2 to 6; M represents a substituted or unsubstituted trivalent aromatic group; Y represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH2— or two or more non-adjacent —CH2— may each independently be substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH?CH—COO—, —CH?CH—OCO—, —COO—CH?CH—, —OCO—CH?CH—, —CH?CH—, —CF?CF—, or —C?C— and any hydrogen atom in the alkyl group may be substituted with a fluorine atom; however, the compound represented by general formula (I-D) does not contain an —O—O— bond,where R1, R2, A1, A2, Z1, Z2, m1, m2, M, Y, W2, r, and LW1 are the same as those in general formula (I-C) or general formula (I-D) described above.

US Pat. No. 10,968,188

BENZOTHIAZOL COMPOUNDS AND METHODS USING THE SAME FOR TREATING NEURODEGENERATIVE DISORDERS

1st Biotherapeutics, Inc....

1. A method for treating neurodegenerative disease in a subject, comprising:administering to the subject in need thereof a therapeutically effective amount of a compound of Formula (I) or a pharmaceutically acceptable salt thereof:

wherein:
R1 is cyclopropyl, wherein R1 is substituted with one or more groups selected from the group consisting of halo, alkyl, hydroxyalkyl and haloalkyl,
R2 and R3 are independently —H, halo, alkyl, alkoxy, —CF3, or —OCF3,
R4 is aryl, monocyclic heteroaryl, cycloalkyl, or heterocyclyl, wherein R4 is optionally substituted with one or more groups selected from the group consisting of halo, hydroxyl, alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, trimethylsilylethoxymethyl, —NO2, —NRaRb, —NRaC(?O)Rb, —NRaC(?O)NRaRb, —NRaC(?O)ORb, —ORa, —CN, —C(?O)Ra, —C(?O)ORa, —C(?O)NRaRb, —OC(?O)Ra, —OC(?O)ORa, —OC(?O)NRaRb, —SRa, azetidinyl, oxetanyl, tetrahydrofuranyl, furanyl, pyrrolidinyl, pyrrolyl, pyrazolyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, furazanyl, oxadiazolyl, thiadiazolyl, phenyl, tetrahydropyranyl, pyranyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperidinyl, piperazinyl, morpholinyl and thiomorpholinyl, and
Ra and Rb are independently —H, halo, amino, alkyl, or haloalkyl, and
wherein the neurodegenerative disease is ?-synucleinopathy, Parkinson's disease, dementia with Lewy body, multiple system atrophy (MSA), Alzheimer's disease or amyotrophic lateral sclerosis (ALS).

US Pat. No. 10,968,187

METHOD FOR PREPARATION OF ALKYLATED OR FLUORO, CHLORO AND FLUOROCHLORO ALKYLATED COMPOUNDS BY HETEROGENEOUS COBALT CATALYSIS

Lonza Solutions AG, Visp...

1. A method for the preparation of fluoro alkylated, chloro alkylated or fluorochloro alkylated compound ALKYLCOMPSUBST with heterogeneous catalysis by a reaction of a compound COMPSUBST with an alkylating agent ALKHAL in the presence of a catalyst CAT;ALKHAL is a compound of formula (III);
R3-X  (III)
wherein
X is Br or I;
R3 is C1-20 alkyl;
wherein the C1-20 alkyl residue R3 of ALKHAL is either unsubstituted, or at least one hydrogen residue of the C1-20 alkyl residue R3 of ALKHAL is substituted by F or Cl;
CAT is Co-L1/C;
L1 is 1,10-phenanthroline;
COMPSUBST is selected from the group consisting of a compound COMPSUBST-I, compound of formula (II), compound of formula (IV), polystyrene, ethene and ethine;
wherein
COMPSUBST-I is a ring RINGA or is a RINGA condensed with a ring RINGB;
RINGA is a 5 or 6 membered carbocyclic aromatic or heterocyclic aromatic ring,
when RINGA is a heterocyclic ring, then RINGA has 1, 2 or 3 identical or different endocyclic heteroatoms independently from each other selected from the group consisting of N, O and S;
when RINGA is a 5 membered ring, then RINGA is unsubstituted or substituted by 1, 2, 3 or 4 identical or different substitutents,
when RINGA is a 6 membered ring then RINGA is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substitutents,
any of said substitutents of RINGA is independently from any other of said substitutent of RINGA selected from the group consisting of C1-20 alkyl, C3-8 cycloalkyl, C1-4 alkoxy, OH, N(R10)R11, CN, NH—OH, NO, NO2, F, Cl, Br, I, CF3, (CH2)m—C(O)Y1, S(O)2R50,

CH?C(H)R28, benzyl, phenyl and naphthyl;
RINGB is a 5 or 6 membered carbocyclic or heterocyclic ring, resulting in a bicyclic having 8, 9 or 10 ring members in total,
when RINGB is a heterocyclic ring, then RINGB contains 1, 2 or 3 identical or different endocyclic heteroatoms independently from each other selected from the group consisting of N, O and S;
RINGB is unsubstituted or substituted with 1, 2 or 3 identical or different substituents in case of RINGB being a 5 membered ring, with 1, 2, 3 or 4 identical or different substituents in case of RINGB being a 6 membered ring, which identical or different substitutents are independently from each other selected from the group consisting of C1-10 alkyl, C3-8 cycloalkyl, C1-4 alkoxy, OH, N(R17)R18, CN, NH—OH, NO, NO2, F, Cl, Br, I, CF3, (CH2)n—C(O)Y2, S(O)2R51, CH?C(H)R38,
benzyl, phenyl and naphthyl;any of said C1-10 alkyl substitutent of RINGA or RINGB is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, OH, O—C(O)—C1-5 alkyl, O—Ch1-10 alkyl, S—Ch1-10 alkyl, S(O)—Ch1-10 alkyl, S(O2)—C1-10 alkyl, O—C1-6 alkylen-O—C1-6 alkyl, C3-8 cycloalkyl and 1,2,4-triazolyl;
any of said benzyl, phenyl and naphthyl substitutent of RINGA or RINGB is independently from each other unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, C1-4 alkoxy, NO2 and CN;
m and n are identical or different and independently from each other an integer from 0 to 10;
wherein
the compound of formula (II) and the compound of formula (IV) being

R40 and R41 are identical or different and independently from each other selected from the group consisting of —(CH2)q—C(O)R13 and —CN;
R42 is selected from the group consisting of —(CH2)q—C(O)R13, —CN and R13;
q is independently an integer from 0 to 10;
wherein
the ethene being unsubstituted or substituted by 1, 2 or 3 substitutents selected from the group consisting of C1-10 alkyl, C3-8 cycloalkyl, C1-4 alkoxy, N(R10)R11, CN, NO, NO2, F, Cl,

Br, I, CF3, (CH2)p—C(O)Y1, S(O)2R50, CH?C(H)R28, benzyl, phenyl and naphthyl;
the ethine being unsubstituted or substituted by 1 substitutent selected from the group consisting of C1-10 alkyl, C3-8 cycloalkyl, C1-4 alkoxy, N(R10)R11, CN, NO, NO2, F, Cl, Br, I, CF3,
(CH2)p-C(O)Y1, S(O)2R50, CH?C(H)R28, benzyl, phenyl and naphthyl;p is independently an integer from 0 to 10;
any of the R24, R34, R28 and R38 are identical or different and independently from each other selected from the group consisting of H, C1-10 alkyl, C(R25)(R26)-O-R27;
any of the R25, R26 and R27 are identical or different and independently from each other selected from the group consisting of H and C1-10 alkyl;
any of the R50 and R51 are identical or different and independently from each other selected from the group consisting of OH, C1-6 alkyl and C1-6 alkoxy;
any of the Y1, Y2 and R13 are identical or different and independently selected from the group consisting of H, OH, C(R14)(R15)R16, C1-6 alkyl, O—C1-6 alkyl, phenyl, benzyl, O—phenyl, O—C1-6 alkylen-O—C1-6 alkyl and N(R19)R20;
any of the R14, R15 and R16 are identical or different and independently from each other selected from the group consisting of H, F, Cl and Br;
any of the R10, R11, R17, R18, R19 and R20 are identical or different and are independently from each other H or C1-6 alkyl, or R10 and R11, R17 and R18 or R19 and R20 represent together tetramethylene or pentamethylene.

US Pat. No. 10,968,186

ASCOCHLORIN DERIVATIVE AND USE THEREOF AS AMPK ACTIVATOR

Tatsuo Hoshino, Kanagawa...

1. A compound represented by formula I:
wherein
R1 is formyl, or —CH?N—O—Y, in which Y is a hydrogen atom or C1-6 alkyl;
R2 is C1-6 alkyl that may be substituted with 1 to 5 fluorine atoms;
R3 is a hydrogen atom or C1-6 alkyl;
R4 is hydroxy, C1-6 alkylamino, C3-7 cycloalkylamino, or 3- to 7-membered heterocycloalkylamino which contains —O—, —S—, —NR6—, —SO— or —SO2— as a ring atom, or
R3 and R4 together with the carbon atom to which they are attached form >C?N—O—Z;
Z is a hydrogen atom, C1-6 alkyl, —CO(CH2)n—R5 or —(CH2)n—R5;
n is an integer selected from 1 to 4;
R5 is —CO2R6, —CONH2, —CONR7R8, —OCONR7R8, —SO2NR7R8, —SO2R9, hydroxy, —NHSO2R9, or —NR7R8;
R6, R7 and R8 are each independently selected from a group consisting of a hydrogen atom, C1-6 alkyl, and C3-7 cycloalkyl; or R7 and R8 together with the nitrogen atom to which they are attached form a nitrogen-containing 3- to 7-membered heterocyclic ring which may further contain —O—, —S—, —NR6—, —SO— or —SO2— as a ring atom, in which the heterocyclic ring may be substituted with one or more substituents selected from hydroxy and C1-6 alkyl; and
R9 is C1-6 alkyl, or C3-7 cycloalkyl;
a pharmaceutically acceptable salt or a solvate thereof.

US Pat. No. 10,968,185

SUBSTITUTED THIAZOLES FOR PREVENTING AND/OR TREATING CELL OR TISSUE NECROSIS

ELA PHARMA LTD., Tel Avi...

1. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient and a compound of Formula II:
or a pharmaceutically acceptable salt thereof,
wherein:
G1 is piperidinyl, optionally substituted with one or more substituents independently selected from the group consisting of halogen, NO2, CN, C1-C6 alkyl, C1-C6 haloalkyl, NH2, OH, OC1-C6 alkyl, C(O)H, C(O)C1-C6 alkyl, C(O)NH2, C(O)OH, and C(O)OC1-C6 alkyl; and
G3 is:

wherein:
G2 is pyrrolidinyl or piperazinyl, each optionally substituted with one or more substituents independently selected from the group consisting of halogen, NO2, CN, C1-C6 alkyl, C1-C6 haloalkyl, NH2, OH, OC1-C6 alkyl, C(O)H, C(O)C1-C6 alkyl, C(O)NH2, C(O)OH, and C(O)OC1-C6 alkyl.

US Pat. No. 10,968,184

PYRIMIDINE PRODRUGS FOR THE TREATMENT OF VIRAL INFECTIONS AND FURTHER DISEASES

Janssen Sciences Ireland ...

4. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt, solvate or polymorph thereof according to claim 1 together with one or more pharmaceutically acceptable excipients, diluents or carriers.

US Pat. No. 10,968,183

SMALL MOLECULE FIEL1 INHIBITOR IN INFLAMMATORY AND FIBROTIC LUNG INJURY

1. A method of treating a disease associated with an activated inflammatory pathway selected from a NF-kB, TGF? and JAK/STAT pathway, the disease selected from pulmonary fibrosis, inflammatory bowel disease, and colitis, the method comprising administering to a subject in need thereof a therapeutically effective amount of a compound represented by Formula (I):
wherein:
R is

and
wherein:
W is selected from the group consisting of H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heterocyclic, halogen, amino, and hydroxy;
X is selected from the group consisting of H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heterocyclic, halogen, amino, and hydroxy;
Y is selected from the group consisting of H, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocyclic;
Z is selected from the group consisting of H, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocyclic, and wherein Y and Z optionally bind together to form a ring;
R? is selected from the group consisting of H, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocyclic;
R? is independently selected from the group consisting of H, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocyclic; and
wherein one or more of the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl may be substituted by one or more C1-C6 alkoxy, halogen or deuterium,
or a pharmaceutically acceptable salt thereof,
wherein the compound is capable of inhibiting NF-kB, TGF? and/or JAK/STAT pathways, and
wherein the compound binds to FIEL1.

US Pat. No. 10,968,182

PROCESS FOR THE PREPARATION OF 2-CYANOIMIDAZOLE COMPOUNDS

Adama Makhteshim Ltd., B...

1. A process for preparation of 2-cyanoimidazole compound represented by the following formula (IV):
which process comprises:
a) reacting of compound represented by the following formula (II):

with the reducing agent selected from the group consisting of metal salts of sulfur-containing derivatives to thereby obtain a compound of Formula I:

b) reacting the compound represented by Formula I with a chlorinating agent to thereby obtain a compound represented by Formula III:

c) reacting the compound represented by Formula III with N,N-Dimethylsulfamoyl chloride in the presence of a base and a polar organic solvent, thereby preparing the 2-cyanoimidazole compound represented by the following formula (IV).

US Pat. No. 10,968,181

NRF2 ACTIVATOR

BIOGEN MA INC., Cambridg...

1. A compound represented by Formula I:
or a pharmaceutically acceptable salt thereof, wherein
R1 is —CN, —C(O)Ra, CH3S(O)2— or C1-8alkyl substituted with one or more fluorine atoms;
Ra is H, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, —OR11, —SR14, —N(R12)2, —NR13OR13, —NR13S(O)2R13, —NR13C(O)R13, —N(R13)N(R13)2, —N(R13)C(O)OR13 or —N(R13)C(O)N(R13)2, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl, and heterocyclyl are each optionally substituted with one or more R21;
R2 is H, halo, —NO2, —CN, —N3, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, —C(O)R13, —C(S)R13, —C(O)OR13, —C(S)SR13, —C(O)SR13, —C(S)OR13, —SC(O)R13, —OC(S)R13, —SC(S)R13, —C(O)N(R13)2, —OR11, —SR14, —N(R12)2, —N(R13)OR13, —N(R13)S(O)2R13, —N(R13)C(O)R13, —N(R13)N(R13)2, —N(R13)C(O)OR13, —N(R13)C(O)N(R13)2, —S(O)2R13, —S(O)R13, —S(O)N(R13)2, —S(O)2N(R13)2, —N+(R13)3, —S+(R13)2 or —Si(R13)3, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21;
R3a is H, C1-2alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, —C(O)R13, —C(O)OR13, —C(O)N(R13)2, —OR11, —N(R12)2, —N(R13)OR13, —N(R13)S(O)2R13, —N(R13)C(O)R13, —N(R13)N(R13)2, —N(R13)C(O)OR13, —N(R13)C(O)N(R13)2, —S(O)R13, —S(O)N(R13)2 or —S(O)2N(R13)2, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21; and
R3b is C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, —C(O)R13, —C(O)OR13, —C(O)N(R13)2, —OR11, —N(R12)2, —N(R13)OR13, —N(R13)S(O)2R13, —N(R13)C(O)R13, —N(R13)N(R13)2, —N(R13)C(O)OR13, —N(R13)C(O)N(R13)2, —S(O)R13, —S(O)N(R13)2 or —S(O)2N(R13)2, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21; or
R3a and R3b are taken together and are C2-12alkylene, C2-12alkenylene or C2-12alkynylene; wherein the C2-12alkylene, C2-12alkenylene, C2-12alkynylene and 3-6-membered carbocyclyl are each optionally substituted with one or more R21;
R4 is H, halo, —NO2, —CN, —N3, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a membered carbocyclyl, a heterocyclyl, —C(O)R13, —C(S)R13, —C(O)OR13, —C(S)SR13, —C(O)SR13, —C(S)OR13, —SC(O)R13, —OC(S)R13, —SC(S)R13, —C(O)N(R13)2, —OR11, —SR14, —N(R12)2, —N(R13)OR13, —N(R13)S(O)2R13, —N(R13)C(O)R13, —N(R13)N(R13)2, —N(R13)C(O)OR13, —N(R13)C(O)N(R13)2, —S(O)2R13, —S(O)R13, —S(O)N(R13)2, —S(O)2N(R13)2, —N+(R13)3, —S+(R13)2 or —Si(R13)3, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21;
“” is either a single bond or a double bond, wherein when “” is a double bond, then R5 is absent; and when “” is a single bond, then
R5 is H, halo, —NO2, —CN, —N3, C1-2alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, —C(O)R13, —C(S)R13, —C(O)OR13, —C(S)SR13, —C(O)SR13, —C(S)OR13, —SC(O)R13, —OC(S)R13, —SC(S)R13, —C(O)N(R13)2, —OR11, —SR14, —N(R12)2, —N(R13)OR13, —N(R13)S(O)2R13, —N(R13)C(O)R13, —N(R13)N(R13)2, —N(R13)C(O)OR13, —N(R13)C(O)N(R13)2, —S(O)2R13, —S(O)R13, —S(O)N(R13)2, —S(O)2N(R13)2, —N+(R13)3, —S+(R13)2 or —Si(R13)3, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21; or
R5 and R3b are taken together with the carbons to which they each are attached form a 3-6-membered carbocyclyl, wherein the 3-6-membered carbocyclyl is optionally substituted with one or more R21;
R6, in each occurrence, is independently halo, —NO2, —CN, —N3, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, —C(O)R13, —C(S)R13, —C(O)OR13, —C(S)SR13, —C(O)SR13, —C(S)OR13, —SC(O)R13, —OC(S)R13, —SC(S)R13, —C(O)N(R13)2, —OR11, —SR14, —N(R12)2, —N(R13)OR13, —N(R13)S(O)2R13, —N(R13)C(O)R13, —N(R13)N(R13)2, —N(R13)C(O)OR13, —N(R13)C(O)N(R13)2, —S(O)2R13, —S(O)R13, —S(O)N(R13)2, —S(O)2N(R13)2, —N+(R13)3, —S(R13)2 or —Si(R13)3; or two R6 attached to the same ring carbon to form an oxo, ?NR14 or C1-12alkylidene, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl heterocyclyl and C1-12alkylidene are each optionally substituted with one or more R21;
X is NRb or O;
Rb is H, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, —C(O)Rc, —C(O)ORc, —C(O)NRcRc, —S(O)2Rc, —S(O)2ORc or —S(O)2NRcRc, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21;
Rc, in each occurrence, is independently selected from H, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl and a heterocyclyl, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21;
R11, in each occurrence, is independently selected from H, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl, C1-12acyl and —Si(R13)3, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl, heterocyclyl, and C1-12acyl are each optionally substituted with one or more R21;
R12, in each occurrence, is independently selected from H, C1-12alkyl, C1-12alkoxy, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl and —Si(R13)3, wherein the C1-12alkyl, C1-12alkoxy, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are each optionally substituted with one or more R21;
R13, in each occurrence, is independently selected from H, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, and a heterocyclyl, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl and heterocyclyl are optionally substituted with one or more R21;
R14, in each occurrence, is independently selected from H, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, a carbocyclyl, a heterocyclyl and C1-12acyl, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, carbocyclyl, heterocyclyl and C1-12acyl are each optionally substituted with one or more R21;
R21, in each occurrence, is independently selected from halo, —OH, —S(O)2R16, C1-12alkyl, C2-12alkenyl, C2-12alkynyl, C1-12alkoxy, a carbocyclyl and a heterocyclyl, wherein the C1-12alkyl, C2-12alkenyl, C2-12alkynyl, C1-12alkoxy, carbocyclyl and heterocyclyl are each optionally substituted with 1 to 3 groups selected from halo, —OH, C1-4alkyl and C1-4alkoxy;
R16, in each occurrence, is independently selected from H or C1-12alkyl;
n is 0 or an integer from 1 to 8;
p is 0, 1 or 2; and
q is 1, 2 or 3,
provided that the sum of p and q is not 4 or 5;
wherein the carbocyclyl is a 3 to 6-membered monocyclic cycloalkyl or phenyl and wherein the heterocyclyl is a 3 to 7-membered saturated monocyclic ring having 1 to 4 heteroatoms independently selected from O, S and N, or a 5- to 7-membered monocyclic heteroaryl having 1 to 4 heteroatoms independently selected from O, S and N.

US Pat. No. 10,968,180

PIPERIDINE DERIVATIVES AS HDAC1/2 INHIBITORS

Regenacy Pharmaceuticals,...

1. A compound of Formula III:
or a pharmaceutically acceptable salt thereof;
wherein,
X1 is N;
X2 is N;
R1 is selected from the group consisting of H and C1-C6-alkyl;
R2 is selected from the group consisting of H, C1-C6-alkyl, and C6-aryl;
R3 is selected from the group consisting of H, C1-C6-alkyl, and C6-aryl;
or R2 and R3 together form a C2-C6-heterocyclyl;
R4 is H; and
R5 is C1-C6-alkyl;
or R4 and R5 together form a C2-C6-heterocyclyl, wherein heterocyclyl is optionally substituted by 1 or 2 of C1-C6-alkyl, halo, or hydroxy.

US Pat. No. 10,968,179

CHARGED ION CHANNEL BLOCKERS AND METHODS FOR USE

Nocion Therapeutics, Inc....

1. A compound represented by Formula (I)
wherein:
Y? is a pharmaceutically acceptable anion;
RA and RB are each independently selected from substituted or unsubstituted alkyl, or;
RC are each independently selected from H, D, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, ORI, CN, NRJRK, NRLC(O)RM, S(O)RN, S(O)2RN, SO2RORP, SO2NRQRR, SO3RS, CO2RT; C(O)RU, and C(O)NRVRW;
each of RI, RJ, RK, RL, RM, RN, RO, RP, RQ, RR, RS, RU, RV, and RW is independently selected from H, D, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl; or RJ and RK or RV and RW or RQ and RR can be taken together with the nitrogen to which they are attached to form a substituted or unsubstituted 5, 6, 7, or 8 membered ring;
X1 is —NRZC(O)—;
RZ is selected from H, D, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, and substituted or unsubstituted alkynyl;
each of RD and RE is independently selected from H, D, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, and substituted or unsubstituted cycloalkyl; or RD and RE together with the carbon to which they are attached form a substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted heterocyclic;
RF and RG together with the N+ to which they are attached form an optionally substituted heterocyclic ring having zero, one or more nitrogen atoms in addition to the N+; and
RH is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl.

US Pat. No. 10,968,178

IP6K INHIBITORS

TAKEDA PHARMACEUTICAL COM...

1. A compound represented by the formula:
wherein
ring A is an optionally substituted aromatic ring;
X is CH or Nor a salt thereof.

US Pat. No. 10,968,177

TRICYCLIC SULFONES AS ROR? MODULATORS

Bristol-Myers Squibb Comp...

1. The compound of the formula (I)or a stereoisomer or pharmaceutically acceptable salt thereof, whereinX is —CR4R5—, —(CR4R5)2, —OCR6R7—, —S(O)pCR6R7— or —NR6CR6R7—;
V and Y are independently 5 or 6-membered aromatic or heteroaromatic rings;
R1 is, independently at each occurrence, selected from hydrogen, CD3, halo, OCF3, CN, —O(C1-C6)alkyl, —O(C1-C6)alkyl-OH, -alkoxyalkoxy (e.g. —O—CH2CH2OCH3), S(O)p(C1-C6)alkyl, —S(O)p(C1-C6)alkyl-OH, -thioalkoxyalkoxy (e.g. —SCH2CH2OCH3), NR11R11, C1-6 alkyl substituted with 0-3 R1a, —(CR1bR1c)r-3-14 membered carbocycle substituted with 0-3 R1a and —(CR1bR1c)r-5-10 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p substituted with 0-3 R1a;
R1a is, independently at each occurrence, hydrogen, ?O, halo, CF3, OCF3, CN, NO2, —(CR1bR1c)r—ORb, —(CR1bR1c)r—S(O)pRb, —(CR1bR1c)r—C(O)Rb, —(CR1bR1c)r—C(O)ORb, —(CR1bR1c)r—OC(O)Rb, —(CR1bR1c)r—NR11R11, —(CR1bR1c)r—C(O)NR11R11, —(CR1bR1c)r—NRbC(O)Rc, —(CR1bR1c)r—NRbC(O)ORc, —NRbC(O)NR11R11, —S(O)pNR11R11, —NRbS(O)pRc, C1-6 alkyl substituted with 0-3 Ra, C1-6 haloalkyl, C2-6 alkenyl substituted with 0-3 Ra, C2-6 alkynyl substituted with 0-3 Ra, —(CR1bR1c)r-3-14 membered carbocycle substituted with 0-3 Ra, or —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p substituted with 0-3 Ra;
R1b and R1c are, independently at each occurrence, hydrogen, halogen or C1-6 alkyl;
R2 is

R2a and R2b are, independently at each occurrence, hydrogen, halo, OCF3, CF3, CHF2, CN, NO2, —(CR1bR1c)r—ORb, —(CR1bR1c)r—S(O)pRb, —(CR1bR1c)r—C(O)Rb, —(CR1bR1c)r—C(O)ORb, —(CR1bR1c)r—OC(O)Rb, —(CR1bR1c)r—NR11R11, —(CR1bR1c)r—C(O)NR11R11, —(CR1bR1c)r—NRbC(O)Rc, —(CR1bR1c)r—NRbC(O)ORc, —NRbC(O)NR11R11, —S(O)pNR11R11, —NRbS(O)pRc, C1-6 alkyl substituted with 0-3 Rf, C1-6 haloalkyl, C2-6 alkenyl substituted with 0-3 Re, C2-6 alkynyl substituted with 0-3 Re, —(CR1bR1c)r-3-14 membered carbocycle, or —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p substituted with 0-4 Rf;
R2c is hydrogen, C1-6 alkyl substituted with 0-3 Rf, C1-6 haloalkyl, —(CR1bR1c)r—C(O)Rb, —(CR1bR1c)r—C(O)ORb, —(CR1bR1c)r—C(O)NR11R11, —(CR1bR1c)r-3-14 membered carbocycle, or —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p substituted with 0-4 Rf;
R3 is, independently at each occurrence, selected from hydrogen, halo, N3, CN, —(CR1bR1c)r—OR3b, —(CR1bR1c)r—NR11R11, C1-6 alkyl substituted with 0-3 R3a, C3-10 cycloalkyl substituted with 0-3 R3a; and phenyl substituted with 0-3 R3a, or 4-10 membered heterocycle containing 1-4 heteroatoms selected from N, O, and S(O)p, substituted with 0-3 R3a, or two R3 located on adjacent carbon atoms link to form a 5-7 membered carbocycle or a 5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatom selected from N, O and S(O)p, both optionally substituted with 0-3 R3a;
R3a is, independently at each occurrence, hydrogen, ?O, halo, OCF3, OCHF2, CF3, CHF2, CN, NO2, —(CR1bR1c)r—ORb, —(CR1bR1c)r—S(O)pRb, —(CR1bR1c)r—C(O)Rb, —(CR1bR1c)r—C(O)ORb, —(CR1bR1c)r—OC(O)Rb, —(CR1bR1c)r—NR11R11, —(CR1bR1c)r—C(O)NR11R11, —(CR1bR1c)r—NRbC(O)Rc, —(CR1bR1c)r—NRbC(O)ORc, —NRbC(O)NR11R11, —S(O)pNR11R11, —NRbS(O)pRc, C1-6 alkyl substituted with 0-3 Ra, C2-6 alkenyl substituted with 0-3 Ra, C2-6 alkynyl substituted with 0-3 Ra, C1-6 haloalkyl, —(CR1bR1c)r-3-14 membered carbocycle substituted with 0-3 Ra, or —(CR1bR1c)r-5-10 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p substituted with 0-3 Ra;
R3b is, independently at each occurrence, hydrogen, CF3, —(CR1bR1c)qORb, —(CR1bR1c)qS(O)pRb, —(CR1bR1c)r—C(O)R3d, —(CR1bR1c)r—C(O)ORb, —(CR1bR1c)qOC(O)Rb, —(CR1bR1c)qNR11R11, —(CR1bR1c)r—C(O)NR11R11, —(CR1bR1c)qNRbC(O)R3c, —(CR1bR1c)qNRbC(O)ORc, —(CR1bR1c)qNRbC(O)N R11R11, —(CR1bR1c)qS(O)2N R11R11, —(CR1bR1c)qNRbS(O)2Rc, C1-6 alkyl substituted with 0-3 Ra, C1-6 haloalkyl, —(CR1bR1c)r-3-14 membered carbocycle substituted with 0-3 Ra, or —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, and S(O), substituted with 0-3 Ra;
R3c and R3d are, independently at each occurrence, hydrogen or C1-6 alkyl;
R4 and R5 are independently hydrogen, halo, C1-6 alkyl or C1-6 haloalkyl, or
R4 and R5 together with the carbon atom to which they are attached form a 3- to 6-membered spirocarbocyclyl ring or a spiroheterocyclyl ring;
R6 and R7 are independently hydrogen, C(?O)C1-4 alkyl, C(?O)OC1-4 alkyl, C1-6 alkyl or C1-6 haloalkyl; or
R6 and R7 taken together are ?O;
R11 is, independently at each occurrence, hydrogen, C1-6 alkyl substituted with 0-3 Rf, CF3, C3-10 cycloalkyl substituted with 0-3 Rf, —(CR1bR1c)r-phenyl substituted with 0-3 Rd, or —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p substituted with 0-4 Rd;
or one R11 and a second R11, both attached to the same nitrogen atom, combine to form a heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p substituted with 0-4 Rd;
Ra is, independently at each occurrence, hydrogen, ?O, halo, OCF3, CF3, CHF2, CN, NO2, —(CR1bR1c)r—ORb, —(CR1bR1c)r—S(O)pRb, —(CR1bR1c)r—C(O)Rb, —(CR1bR1c)r—C(O)ORb, —(CR1bR1c)r—OC(O)Rb, —(CR1bR1c)r—NR11R11, —(CR1bR1c)r—C(O)NR11R11, —(CR1bR1c)r—NRbC(O)Rc, —(CR1bR1c)r—NRbC(O)ORc, —NRbC(O)NR11R11, —S(O)pNR11R11, —NRbS(O)pRc, C1-6 alkyl substituted with 0-3 Rf, C1-6 haloalkyl, C2-6 alkenyl substituted with 0-3 Re, C2-6 alkynyl substituted with 0-3 Re, —(CR1bR1c)r-3-14 membered carbocycle, or —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p substituted with 0-4 Rf;
Rb is, independently at each occurrence, hydrogen, C1-6 alkyl substituted with 0-3 Rd, C1-6 haloalkyl, C3-6 cycloalkyl substituted with 0-3 Rd, —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p substituted with 0-4 Rf, or —(CR1bR1c)r-6-10 membered carbocycle substituted with 0-3 Rd;
Rc is, independently at each occurrence, C1-6 alkyl substituted with 0-3 Rf, —(CR1bR1c)r—C3-6 cycloalkyl substituted with 0-3 Rf, or —(CR1bR1c)r-phenyl substituted with 0-3 Rf;
Rd is, independently at each occurrence, hydrogen, ?O, halo, OCF3, CF3, CN, NO2, —ORe, —(CR1bR1c)r—C(O)Rc, —NReRe, —NReC(O)ORc, C(O)NReRe, —NReC(O)Rc, CO2H, CO2Rc, —NReSO2Rc, SO2Rc, C1-6 alkyl substituted with 0-3 Rf, C3-6 cycloalkyl substituted with 0-3 Rf, —(CR1bR1c)r-phenyl substituted with 0-3 Rf or —(CR1bR1c)r-5-7 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p substituted with 0-4 Rf;
Re is, independently at each occurrence, selected from hydrogen, C(O)NRfRf, C1-6 alkyl, C3-6 cycloalkyl, -5-7 membered heterocycle or —(CR1bR1c)r-phenyl substituted with 0-3 Rf;
Rf is, independently at each occurrence, hydrogen, ?O, halo, CN, NH2, NH(C1-6 alkyl), N(C1-6 alkyl)2, SO2(C1-6 alkyl), CO2H, CO2(C1-6 alkyl), OH, C3-6 cycloalkyl, CF3; O(C1-6 alkyl); or an optionally substituted —(CR1bR1c)r-5-10 membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, P(?O) and S(O)p, phenyl or C3-6 cycloalkyl, each group optionally substituted with halo, CN, CF3, C1-6 alkyl or O(C1-6 alkyl);
m is 0, 1, 2 or 3
n is 0, 1 or 2;
p and q are, independently at each occurrence, 0, 1, or 2;
r is 0, 1, 2, 3, or 4;
t is 0 or 1; and
w is 1, 2 or 3.

US Pat. No. 10,968,176

PYRROLIDONE DERIVATIVES, OLIGOMERS AND POLYMERS

NanoSynthons LLC, Mt. Pl...

1. Fluorescent cyclic amide, cyclic urea, cyclic urethane and cyclic amino amide or amino urea compounds of the formula
wherein:
Q is the residue of a compound having at least one primary amine that provides the nitrogen atom in the ring as shown;
W is N, O, S or (CH2)n where n is 0 or 1;
R2 is —C(O)OH; —C(O)O(C1-C4 alkyl); 2-oxazoline; —C(O)—NHR5 wherein R5 is H; —C1-C4 alkyl or an amido group that can be a moiety on a polymer; including pharmaceutically acceptable salts and esters of —CO2H;
m is 1-4; and
with the proviso that the compound of Formula (I) fluoresces after excitation at least 10×the value of its base compound which is QH2 not having such cyclic amides, cyclic urea, cyclic urethanes or cyclic amino amide entities present.

US Pat. No. 10,968,175

RESIST COMPOSITION AND PATTERNING PROCESS

SHIN-ETSU CHEMICAL CO., L...

1. A resist composition comprising a base polymer and a sulfonium salt having the formula (A-1) and/or an iodonium salt having the formula (A-2):wherein R1 is hydroxyl, carboxyl, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 acyloxy, fluorine, chlorine, amino, —NR8—C(?O)—R9, or —NR8—C(?O)—O—R9, R8 is hydrogen or a C1-C6 alkyl group, R9 is a C1-C6 alkyl, C2-C8 alkenyl or C7-C20 aralkyl group,R2 is a C2-C12 alkylene group in which at least one hydrogen may be substituted by a halogen other than fluorine, or a C6-C10 arylene group in which at least one hydrogen may be substituted by a C1-C10 alkyl, C1-C10 alkoxy, halogen or hydroxyl moiety,
R3, R4 and R5 are each independently fluorine, chlorine, bromine, iodine or a C1-C20 monovalent hydrocarbon group which may contain a heteroatom, any two of R3, R4 and R5 may bond together to form a ring with the sulfur atom to which they are attached,
R6 and R7 are each independently trifluoromethyl or a C1-C20 monovalent hydrocarbon group which may contain a heteroatom, X1 is a single bond or a (p+1)-valent C1-C20 linking group which may contain an ether bond, carbonyl, ester bond, amide bond, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety,
X2 is an ether bond,
m is an integer of 1 to 5, n is an integer of 0 to 3, m+n is 1 to 5, and p is an integer of 1 to 3.

US Pat. No. 10,968,174

SYNTHESIS OF A THIOSULFONIC ACID BY A STEP OF PERIODATE MEDIATED OXIDATIVE COUPLING OF A THIOSULFONIC ACID WITH AN ANILINE

WisTa Laboratories Ltd., ...

1. A method of chemical synthesis of a compound of Formula (1):
comprising a step of periodate mediated oxidative coupling, in which a compound of Formula (2):

is reacted with a compound of Formula (3):

and a periodate oxidising agent;
to form said compound of Formula (1);
wherein:
—R1A1 is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R1A2 is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R1B1 is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R1B2 is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R2A is independently —H or —R3AA;
—R2AA is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R2B is independently —H or —R3AA;
—R2BB is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C-1- 4alkyl;
—R3A is independently —H or —R3AA;
—R3AA is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R3B is independently —H or —R3BB;
—R3BB is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R4A is independently —H or —R4AA;
—R4AA is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl;
—R4B is independently —H or —R4BB; and
—R4BB is independently C1-4alkyl; C2-4alkenyl; halogenated C1-4alkyl; C5-10aryl; halogenated C5-10aryl; C5-10aryl-C1-4alkyl; or halogenated C5-10aryl-C1-4alkyl.

US Pat. No. 10,968,173

THIOCARBONYLTHIO COMPOUNDS AS CHAIN TRANSFER AGENTS SUITABLE FOR RAFT POLYMERIZATION

IOWA STATE UNIVERSITY RES...

1. A compound having the structure of formula (I):whereinR1 is aryl or SC1-20 alkyl, wherein the aryl and SC1-20 alkyl can be optionally substituted with 1-5 substituents independently selected in each occurrence thereof from the group consisting of H, C1-6 alkyl, halogen, —OR5, —SR5, and —NR6R7,
R2 is C1-6 alkyl,
R3 is H or C1-6 alkyl,
R4 is H or C1-6 alkyl,
R5 is H or C1-6 alkyl,
R6 is H or C1-6 alkyl, and
R7 is H or C1-6 alkyl,with the proviso that when R4 is methyl then R1 is not aryl or —S-t-Bu.

US Pat. No. 10,968,172

USP30 INHIBITORS

Mitobridge, Inc., Cambri...

1. A compound represented by structural formula (I):or a pharmaceutically acceptable salt thereof, wherein:X is phenyl or naphthyl;
Y is absent, a methylene group, an ethylene group, or an ethenylene group;
R1 is (C1-C4)alkyl, 3-7 membered cycloalkyl, 5-6 membered heterocyclyl, 6-10 membered aryl, or 5-6 membered heteroaryl, each of which is independently optionally substituted with one or more substituents selected from the group consisting of halogen, CN, —CO2H, hydroxyl, (C1-C4)alkyl, halo(C1-C4)alkyl, (C1-C4)alkoxy, halo(C1-C4)alkoxy, methylenedioxy, phenyl, —NO2, —ORc, NRaRb, —S(O)iRa, —NRaS(O)iRb, —S(O)iNRaRb, —C(?O)ORa, —OC(?O)ORa, —C(?S)ORa, —O(C?S)Ra, —C(?O)NRaRb, —NRaC(?O)Rb, —C(?S)NRaRb, —NRaC(?S)Rb, —NRa(C?O)ORb, —O(C?O)NRaRb, —NRa(C?S)ORb, —O(C?S)NRaRb, —NRa(C?O)NRaRb, —NRa(C?S)NRaRb, —C(?S)Ra, and —C(?O)Ra;
R2 is 3-7 membered cycloalkyl, 5-6 membered heterocyclyl, 6-10 membered aryl, 5-6 membered heteroaryl, or bridged 5-10 membered cycloalkyl; each of which is independently optionally substituted with one or more substituents selected from the group consisting of halogen, CN, —CO2H, hydroxyl, (C1-C4)alkyl, halo(C1-C4)alkyl, (C1-C4)alkoxy, halo(C1-C4)alkoxy, (C1-C4)alkylthio, —NO2, —NRaRb, —S(O),Ra, —NRaS(O)iRb, —S(O)iNRaRb, —C(?O)ORa, —OC(?O)ORa, —C(?S)ORa, —O(C?S)Ra, —C(?O)NRaRb, —NRaC(?O)Rb, —C(?S)NRaRb, —NRaC(?S)Rb, —NRa(C?O)ORb, —O(C?O)NRaRb, —NRa(C?S)ORb, —O(C?S)NRaRb, —NRa(C?O)NRaRb, —NRa(C?S)NRaRb, —C(?S)Ra, and —C(?O)Ra;
R3 is isopropyl, t-butyl, 1-methylcyclopropyl, 1-fluoromethylcyclopropyl, 1-difluoromethylcyclopropyl, 1-trifluoromethylcyclopropyl, or 3-methyl-3-oxetanyl;
each Ra and each Rb are independently selected from —H and (C1-C5)alkyl, optionally substituted with hydroxyl or (C1-C3)alkoxy;
Rc is —H, (C1-C5)haloalkyl or (C1-C5)alkyl, wherein the (C1-C5)alkyl is optionally substituted with hydroxyl or (C1-C3)alkoxy; and
i is 0,1 or 2.

US Pat. No. 10,968,171

FRACTURING FLUID COMPRISING A (CO)POLYMER OF A HYDRATED CRYSTALLINE FORM OF 2-ACRYLAMIDO-2-METHYLPROPANE SULPHONIC ACID AND HYDRAULIC FRACTURING METHOD

S.P.C.M. SA, Andrezieux ...

1. A fracturing fluid comprising water, at least one propping agent and at least one water-soluble (co)polymer prepared from a hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid and/or of at least one of its salts;wherein the hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid has a 2-theta powder X-ray diffraction diagram comprising peaks at 10.58°, 11.2°, 12.65°, 13.66°, 16.28°, 18.45°, 20°, 20.4°, 22.5°, 25.5°, 25.88°, 26.47°, 28.52°, 30.28°, 30.8°, 34.09°, 38.19°, 40.69°, 41.82°, 43.74°, and 46.04° degrees, all peak values being +/?0.1°.

US Pat. No. 10,968,169

UREA DERIVATIVE

Daiichi Sankyo Company, L...

1. A compound represented by formula (I) or a pharmacologically acceptable salt thereof:
wherein
Ar represents a group represented by the following formula:

wherein R1 represents a C3-C6 cycloalkyl group, R2 represents a C2-C6 alkyl group or a C3-C6 cycloalkyl group, n represents 0, 1 or 2, and X each independently represents a halogen atom, a cyano group, a halogeno C1-C6 alkyl group, a cyano C1-C6 alkyl group, a cyano C3-C6 cycloalkyl group, a halogeno C1-C6 alkoxy group, a halogeno C1-C6 alkylthio group, a saturated cyclic amino group, a halogeno saturated cyclic amino group, a phenyl group or a halogeno phenyl group.

US Pat. No. 10,968,166

4-(P-QUINONYL)-2-HYDROXYBUTANAMIDE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES

PTC THERAPEUTICS, INC., ...

1. A compound of Formula A:
wherein:
R5 is hydrogen, and R6 is C1-C6-alkyl; where the alkyl group is optionally substituted with —S(O)0-2R10, —CN, —F, —Cl, —Br, —I, —NR10R10, C3-C6-cycloalkyl, aryl, heteroaryl, heterocyclyl, —C(O)—R11, —C(O)—C0-C6-alkyl-aryl, —C(O)—O—R11, —C(O)—O—C0-C6-alkyl-aryl, —C(O)—NR11R11, —C(O)—NH—C0-C6-alkyl-aryl, —NH—C(O)—R11, or —NH—C(O)—C0-C6-alkyl-aryl; where the aryl, heteroaryl, and heterocyclyl ring substituents are optionally further substituted with halo, C1-C6-alkyl, C1-C6-haloalkyl, oxo, hydroxy, C1-C6-alkoxy, —C(O)—C1-C6-alkyl, or —C(O)—O—C1-C6-alkyl;
and where one of the carbons of the R6 C1-C6-alkyl group is replaced with a heteroatom selected from the group consisting of —O—, —N—, and —S—;
and wherein the R6 C1-C6-alkyl group is cyclic or a combination of cyclic and linear or branched;
R10 and R10? are independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, aryl, aryl-C1-C6-alkyl, heteroaryl, heterocyclyl, —C(O)—H, —C(O)—C1-C6-alkyl, —C(O)-aryl, and —C(O)—C1-C6-alkyl-aryl; and
R11 is selected from the group consisting of hydrogen and C1-C6-alkyl;
or a salt, a stereoisomer, or a mixture of stereoisomers thereof.

US Pat. No. 10,968,165

POLYASPARTIC ACID ESTER COMPOSITIONS AND METHOD FOR PURIFICATION

Covestro Deutschland AG, ...

1. A polyaspartic ester composition, comprising: a compound of the general formula (I)
in which
X is an m-valent organic radical obtained by removing primary amino groups from a corresponding polyamine in the molecular weight range from 60 to 6000 g/mol, and which comprises further functional groups that are reactive toward isocyanate groups and/or inert at temperatures of up to 100° C., wherein the m-valent organic radical optionally contains one or more heteroatoms, and wherein the corresponding polyamine comprises aromatically, (cyclo)aliphatically, or araliphatically attached primary amino groups,
R1 and R2 are identical or different organic radicals each having 1 to 18 carbon atoms,
m is an integer >1
wherein the polyaspartic ester composition comprises from 0.01% to <2% by weight of dialkyl fumarate and has a platinum-cobalt color index of <100.

US Pat. No. 10,968,163

ALPHA-TRUXILLIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF

The Research Foundation f...

1. A compound of having the structure:
wherein
one of R1 or R2 is —C(?O)OH and the other of R1 or R2 is —C(?O)OR13 or —C(?O)O-alkyl-R14,
wherein
R13 is aryl, and
R14 is aryl; and
R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are each independently, H, —OR15 or halogen,
wherein R15 is C1-10 alkyl,
wherein when one of R1 or R2 is —C(?O)OH and R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are each H, then the other of R1 or R2 is other than —C(?O)OR13 where R13 is 1-naphthyl or 2-naphthyl, or —C(?O)O-alkyl-R14 where the alkyl is a branched C2 alkyl and the R14 is phenyl,
or an enantiomer or racemate thereof;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,968,162

METHOD FOR THE SYNTHESIS AND PURIFICATION OF ARYL ACID ESTERS

Miami University, Oxford...

1. A method for the synthesis of an aryl ester of formula II,
wherein R1, R2, R3, R4, and R5 each independently represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, a halogen atom, an alkoxy group having from 1 to 6 carbon atoms, a haloalkyl group having from 1 to 6 carbon atoms, a haloalkoxy group having from 1 to 6 carbon atoms, an alkylthio group having from 1 to 6 carbon atoms, an alkylsulphonyl group having from 1 to 6 carbon atoms, a nitro group, a hydroxy group, a cyano group, an amino group, an alkylamino group having from 1 to 6 carbon atoms or a dialkylamino group having from 1 to 6 carbon atoms in each alkyl part,
wherein n is equal to 0 or to an alkyl group having from 1 to 6 carbon atoms,
wherein R6 represents an alkyl group having from 1 to 6 carbon atoms or a cycloalkyl group having from 3 to 6 carbon atoms,
the method comprises:
mixing an aryl acid according to formula I, with an alcohol solvent and an acid catalyst to form a reaction mixture,

heating the reaction mixture for a period of 0.5 to 10 hours,
filtering the reaction mixture to obtain an aryl ester,
and washing the aryl ester with a second solvent,
wherein the molar ratio of aryl acid to alcohol solvent is 1:100 to 1:5, and wherein the molar ratio of aryl acid:acid catalyst is from 1:0.5 to 1:0.01.

US Pat. No. 10,968,159

METHOD FOR MANUFACTURING TEREPHTHALIC ACID

FAR EASTERN NEW CENTURY C...

1. A method for manufacturing terephthalic acid, comprising:providing a titrant receptor solution, wherein the titrant receptor solution includes water, and a pH value of the titrant receptor solution is in a range of 1.0-3.5;
adding a disodium terephthalate aqueous solution and an acid titrant into the titrant receptor solution to form terephthalic acid crystals and an end-point solution, wherein a pH value of the titrant receptor solution is in a range of 1.0-3.5; and
separating the terephthalic acid crystals from the end-point solution, wherein a pH value of the end-point solution is in a range of 1.0-3.5.

US Pat. No. 10,968,153

METHOD OF CONVERTING A BROMINATED HYDROCARBON TO A CHLORINATED HYDROCARBON

Eagle US 2 LLC, Houston,...

1. A method of converting a brominated hydrocarbon to a chlorinated hydrocarbon comprising:(a) providing said brominated hydrocarbon, wherein said brominated hydrocarbon comprises at least one replaceable bromo group, wherein each replaceable bromo group is independently covalently bonded to a sp3 hybridized carbon;
(b) contacting together said brominated hydrocarbon and an ion exchange resin comprising chloride groups, wherein said ion exchange resin comprises water in an amount of less than or equal to 30 percent by weight, based on the total weight of said ion exchange resin and water, thereby replacing at least one replaceable bromo group of said brominated hydrocarbon with a chloro group, and converting at least a portion of said brominated hydrocarbon to said chlorinated hydrocarbon; and
(c) isolating said chlorinated hydrocarbon from said ion exchange resin.

US Pat. No. 10,968,152

SIMPLIFIED PROCESS FOR ISOLATING PURE 1,3-BUTADIENE

BASF SE, Ludwigshafen am...

1. A process for isolating pure 1,3-butadiene from a crude C4 fraction, the process comprising:introducing the crude C4 fraction into a predistillation column comprising a dividing wall running in a longitudinal direction of the predistillation column, and taking off a C3 low boiler fraction, comprising C3 hydrocarbons, as an overhead stream from the predistillation column, taking off a high boiler fraction as a bottom stream from the predistillation column, and taking off a purified C4 fraction as a side stream from the predistillation column;
extractively distilling the purified C4 fraction using a selective solvent to obtain a fraction comprising butanes and butenes and a pure 1,3-butadiene fraction comprising at least 99.5 wt. % 1,3-butadiene,
wherein the purified C4 fraction comprises a lower boiler in an amount equal to or lower than a prescribed maximum lower boiler content and 1,2-butadiene in an amount equal to or lower than a prescribed maximum 1,2-butadiene content, and
wherein the prescribed maximum 1,2-butadiene content is 25 ppm, based on 1,3-butadiene.

US Pat. No. 10,968,151

SYSTEM AND PROCESS FOR RECOVERING METHANE AND CARBON DIOXIDE FROM BIOGAS AND REDUCING GREENHOUSE GAS EMISSIONS

WM INTELLECTUAL PROPERTY ...

1. A process for recovering methane and carbon dioxide from a biogas source for beneficial use or sequestration, comprising the steps of:(a) extracting at least one gas stream comprising a biogas from a biogas-generating facility;
(b) compressing, cooling, and separating the gas stream from liquid water;
(c) removing a majority of trace contaminants from the gas stream;
(d) removing oxygen from the gas stream to produce a deoxygenated gas stream;
(e) drying the gas stream to reduce the water vapor content;
(f) cooling the gas stream in a liquefaction unit to liquefy at least some of the contained carbon dioxide;
(g) utilizing the liquified carbon dioxide as an absorbent to purify the gas stream;
(h) separating any remaining gaseous carbon dioxide from the gas stream and recycling the gaseous carbon dioxide to a point upstream from the liquefaction unit such that the carbon dioxide contained in the gas stream is substantially separated and recovered as a liquid product;
(i) separating nitrogen from the gas stream to produce a biomethane product stream;
(j) sequestering or supplying the carbon dioxide product for sequestration or other utilization;
(k) utilizing or supplying the biomethane product stream as a compressed or liquefied fuel for vehicles, as process heat fuel, as feedstock for fuel or chemical synthesis, or as feedstock for hydrogen generation; and
(l) monitoring the material and energy inputs and outputs from a biogas processing facility to determine reductions in greenhouse gas emissions, wherein at least some of steps (b)-(i) occur in the biogas processing facility.

US Pat. No. 10,968,150

METHOD AND APPARATUS FOR PRODUCING 1,3-BUTADIENE

ZEON CORPORATION, Tokyo ...

1. A method for producing 1,3-butadiene, comprising:a) separating a C4 hydrocarbon mixture by extractive distillation to produce a fraction comprising 1,3-butadiene and a Fraction I comprising butenes and butanes;
b) separating the fraction comprising 1,3-butadiene to produce a Fraction II comprising impurities having a lower boiling point than 1,3-butadiene, a Fraction III comprising impurities having a higher boiling point than 1,3-butadiene, a fraction enriched in vinylacetylene, and a fraction enriched in 1,3-butadiene,
wherein Fraction I, Fraction II, and Fraction III each have a lower vinylacetylene content than the fraction enriched in vinylacetylene;
c) combining Fraction I, Fraction II, and Fraction III to produce a diluent,
d) adding the diluent to the fraction enriched in vinylacetylenes to produce a diluted fraction having a lower vinylacetylene content than the fraction enriched in vinylacetylenes,
wherein the diluent consists of Fraction I, Fraction II, and Fraction III, a concentration of vinylacetylene in the diluted fraction is 15 mass % or less, and a concentration of 1,3-butadiene in the diluted fraction is 20 mass % or less; and
e) passing the diluted fraction to a hydrogenation treatment and hydrogenating the vinylacetylene to produce a hydrogenated mixture comprising 1,3-butadiene.

US Pat. No. 10,968,149

ENHANCED OXYGEN TRANSFER AGENT SYSTEMS FOR OXIDATIVE DEHYDROGENATION OF HYDROCARBONS

EcoCatalytic Inc., Wobur...

1. A method for producing one or more olefins from a hydrocarbon feed comprised of one or more alkanes, the method comprising:a step of contacting a hydrocarbon feed comprised of one or more alkanes with an oxygen transfer agent at a temperature of 825° C. to 1000° C., wherein the oxygen transfer agent comprises i) an oxygen-donating chalcogen agent comprising at least one of a sulfate salt of an alkaline earth metal or a sulfate salt of an alkali metal, and a sulfate salt of manganese, and wherein the oxygen-donating chalcogen agent has an oxidation state greater than +2, and ii) a reducible metal oxide, wherein the oxygen-donating chalcogen agent and the reducible metal oxide are in solid form, and wherein water is formed from oxygen donated by the oxygen-donating chalcogen agent.

US Pat. No. 10,968,148

METHOD OF PRODUCING COMPOUND COMPRISING ALKENYL GROUP

UNIVERSITY COLLEGE CARDIF...

1. A method of producing at least one compound comprising an alkenyl group from at least one compound comprising an alkyl group having two or more carbon atoms, the method comprising:(i) Providing a mixture comprising carbon dioxide and at least one compound comprising an alkyl group having two or more carbon atoms, the mixture comprising at least 5 mol % carbon dioxide; and
(ii) Contacting said mixture with a catalyst comprising (a) one or both of palladium and platinum, and (b) one or more of the lanthanide series of elements, thereby converting at least a portion of the at least one compound comprising an alkyl group having two or more carbon atoms into a compound comprising an alkenyl group, wherein the catalyst comprises at least 2.0 mol % and up to 15.0 mol % palladium, platinum or combination thereof based on a total for palladium and/or platinum relative to total catalyst,
wherein a molar ratio of the one or more of the lanthanide series of elements to the one or both of palladium and platinum is from 1:1 to 15:1 in the catalyst, and
wherein the contacting in step (ii) is conducted at a temperature of at least 300° C. and up to 600° C.

US Pat. No. 10,968,146

LAWN SUBSTITUTE AND METHODS THEREFOR

DLT Growers, Inc., Ontar...

1. A method of propagating or cultivating a variety of Rushia lineolata, comprising:providing a variety of Rushia lineolata; and
propagating or cultivating the variety in a conditioned medium that includes a porous low-density glass component, an acidic organic absorbent component, and a microbial organic component; and
wherein conditioned medium is prepared by mixing the porous low-density glass component and the acidic organic adsorbent component in a ratio of 55-65 wt % perlite and 35-45 wt % peat moss, and wherein 60-70% by volume of the above mixture is mixed with 30-40% by volume of the decomposed organic component to obtain the conditioned medium.

US Pat. No. 10,968,144

SYSTEMS AND METHODS FOR PRODUCING POTASSIUM SULFATE

Marsulex Environmental Te...

1. A method of producing potassium sulfate, the method comprising:providing an industrial waste material that includes at least one metal sulfate or a metal product that has been reacted with sulfuric acid to produce at least one metal sulfate;
reacting the metal sulfate with potassium carbonate to produce a byproduct comprising potassium sulfate;
separating and/or filtering the byproduct to remove metal carbonates therefrom and produce a filtered liquor; and
refining the filtered liquor to produce solid potassium sulfate via a crystallization process.

US Pat. No. 10,968,143

THREE-PART PLANT NUTRIENT SYSTEM

HGCI, Inc., Las Vegas, N...

11. A three-part primary nutrient system for facilitating the growth of a plant in any growing media comprising:a first part comprising nitrogen in the range of 3.0%-6.3% and calcium in the range of 2.6%-6.3%, wherein the ranges provided are by volume;
a second part comprising nitrogen in the range of 1.5%-2.9%, phosphate in the range of 1.2%-3.1%, potash in the range of 2.8%-4.8%, magnesium in the range of 1%-2.1%, sulfur in the range of 1.5%-2.9%, iron in the range of 0.05%-0.35%, and comprising trace minerals in the range of 0.075%-0.125%, wherein the ranges provided are by volume, and devoid of calcium; and
a third part comprising at least one of potassium, phosphorus, sulfur, magnesium, or minor minerals and devoid of nitrogen and calcium, the third part further comprising phosphate in the range of 4.5%-7.5%, potash in the range of 4.5%-7.5%, magnesium in the range of 1.0-2.9%, sulfur in the range of 1.5%-2.9%, iron in the range of 0.08%-0.35%, and minor minerals in the range of 0.075%-0.125%, wherein the ranges provided are by volume.

US Pat. No. 10,968,142

ENHANCED CARBONATION AND CARBON SEQUESTRATION IN CEMENTITIOUS BINDERS

THE REGENTS OF THE UNIVER...

1. A manufacturing process of a cement-based product, comprising:(a) combining at least one cement component that includes portlandite (Ca(OH)2) with aggregates;
(b) shaping the at least one cement component and the aggregates to form a monolithic structural element;
subsequent to the shaping in (b),
(c) disposing the monolithic structural element in a reactor;
(d) exposing the monolithic structural element in the reactor to gaseous CO2 to form a cement-based product,
wherein the exposing in (d) includes converting portlandite to calcium carbonate, and
wherein a partial pressure (concentration) of the CO2 present in the reactor is higher than a partial pressure of CO2 in ambient atmosphere.

US Pat. No. 10,968,140

HIGHLY POROUS CERAMIC AND METAL AEROGELS FROM XEROGEL POWDER PRECURSORS, AND METHODS FOR THEIR PRODUCTION AND USE

1. A method for preparing sturdy, shaped, highly porous metal carbide monolithic aerogel objects, wherein the metal carbide is selected from ZrC, HfC, TiC, and Cr3C2, said method comprising the steps of:(a) preparing a nanoparticulate polyurea-modified metal-oxide composite xerogel powder in accordance with the following steps:
(a1) preparing a first solution comprising a metal oxide-precursor in a first solvent, wherein the metal oxide-precursor is a metal chloride salt, and the first solvent is an alcohol selected from MeOH and EtOH;
(a2) measuring out a portion of the first solution of metal oxide-precursor and treating it under vigorous stirring with an amount of H2O such that the mol/mol ratio of H2O:metal oxide-precursor is between about 5 and about 7, followed with a non-polar solvent selected from hexane and pentane in an amount between about 2000 mL and about 4000 mL per mol of metal oxide-precursor, and with a proton-scavenging agent in an amount such that the mol/mol ratio of proton-scavenging agent:metal oxide-precursor is between about 7 and about 12, and followed by continued vigorous stirring at ambient temperature for a period of time ranging between about 18 hours and about 30 hours, to provide a metal-oxide suspension, followed by subjecting the metal-oxide suspension to between 1 and 5 washings with one or more wash solvents selected from an ester solvent and a ketone solvent, followed by removing the solvents, to provide a nanoparticulate metal-oxide slurry;
(a3) reacting separately the nanoparticulate metal-oxide slurry obtained in step (a2) with one or more polyisocyanate compound in an ester solvent at a temperature between about 55° C. and about 75° C. for a period of time between about 2 days and about 4 days, followed by 1-3 washings with an ester solvent, and drying under vacuum, to obtain a nanoparticulate polyurea-modified metal-oxide composite xerogel powder or a polyurea-modified metal-oxide/boron-oxide composite xerogel powder, wherein the polyisocyanate compound is a compound of the general formula G1-(NCO)q, in which G1 is a moiety selected from C1-C10 straight chain alkyl or branched alkyl or cycloalkyl, alkylaryl, aryl, heteroalkyl, heterocyclylalkyl, or heteroaryl, each of which is optionally substituted, and q is an integer in the range 2-6, and wherein the amount of polyisocyanate compound used is such that the ratio of total NCO groups per mol of metal-oxide precursor is in the range between about 0.5 and about 0.9;
(b) compressing said nanoparticulate polyurea-modified metal-oxide composite xerogel powder in one or more dies under a pressure between about 10,000 psi and about 20,000 psi, to obtain one or more shaped, nanoparticulate polyurea-modified metal-oxide composite xerogel monolithic compacts;
(c) subjecting said shaped, nanoparticulate polyurea-modified metal-oxide composite xerogel monolithic compacts to pyrolysis under flowing Ar gas at a temperature between about 1300° C. and about 1700° C. for a period of between about 24 hours and about 48 hours, to obtain the sturdy, shaped, highly porous metal carbide monolithic aerogel objects.

US Pat. No. 10,968,139

MOLDABLE SILICON NITRIDE GREEN-BODY COMPOSITE AND REDUCED DENSITY SILICON NITRIDE CERAMIC PROCESS

ATC Materials, Inc., Wes...

1. A process for preparing a moldable green-body composite comprising:a) providing silicon nitride powder;
b) providing a surface modifier;
c) providing a binder comprising polysiloxane or polysilazanes,
d) providing an anti-agglomerate;
e) providing a sintering aid;
f) milling the silicon nitride powder and sintering aid with a first solvent to create a mill slurry of silicon nitride particles and milling said mill slurry to produce silicon nitride particles having a first average particle size of no more than 5 ?m;
g) adding the surface modifier to the mill slurry and mixing at an elevated temperature to chemically modify a surface of the silicon nitride particles;
h) adding the anti-agglomerate to the mill slurry and mixing at a first temperature to create a dispersed slurry having dispersed silicon nitride particles;
i) combining the binder and a second solvent to produce a pre-dissolved binder having 25 to 50 volume percent binder;
j) adding the pre-dissolved binder to the dispersed slurry and mixing at a second temperature, that is effectively low to prevent curing of the binder, to create a green body slurry;
wherein the second temperature is below 60° C.:
k) removing the first and second solvents under a vacuum until the green body slurry comprises no more than about 2% by weight solvent; thereby producing a moldable green-body composite, having a binder concentration of between 30% and 50% by volume.

US Pat. No. 10,968,138

GYPSUM SLURRIES WITH LINEAR POLYCARBOXYLATE DISPERSANTS

UNITED STATES GYPSUM COMP...

1. A settable slurry comprising:a mixture of
water;
a hydraulic component comprising at least 80% calcium sulfate hemihydrate by weight based on the dry weight of the hydraulic component, wherein calcium sulfate anhydrite, synthetic gypsum or landplaster is less than 20% of the hydraulic material; and
a linear polycarboxylate anionic dispersant comprising a first monomeric repeating unit A and a second monomeric repeating unit B, and an absence of polyvinyl acetate monomeric units;
wherein the first monomeric repeating unit A is at least one carboxylic acid functional group containing olefinic moiety of formula I:

wherein R is selected from the group consisting of —CH3, and —CH2—C(O)—OH, or a Na, K, or NH4+ salt thereof, wherein linear polycarboxylate anionic dispersant has an absence of acrylic acid monomer; and
wherein the second monomeric repeating unit B is at least one vinyl sulfonate according to formula II:

wherein X is NH or O; R1 is H or —CH3; R2 is a linear or branched alkylene group having the formula —(CnH2n)—, wherein n=2 to 6; M=H, Na, K, or NH4+;
wherein the molar ratio of the first repeating unit A to the second repeating unit B is A is between 1:9 and 9:1;
wherein the weight average molecular weight of the linear polycarboxylate anionic dispersant is 3000 to 100000 Daltons;
wherein the slurry has a water to calcium sulfate hemihydrate weight ratio of 0.1-1.5:1, wherein the dispersant is present in the slurry in an amount of from about 0.01% to about 2% by weight of the dry dispersant calculated as a percentage of the calcium sulfate hemihydrate.

US Pat. No. 10,968,137

PROCESS FOR BENEFICIATING FLY ASH, BENEFICIATED FLY ASH, AND CEMENTITIOUS COMPOSITIONS CONTAINING BENEFICIATED FLY ASH

ROMAN CEMENT, LLC, Salt ...

1. A method of converting a non-conforming fly ash into conforming fly ash, comprising:obtaining an initial fly ash with at least one non-conforming characteristic selected from excess carbon or low reactivity index as defined by ASTM C-618 and having a D10, D50 and D90;
classifying the initial fly ash using one or more air classifiers to produce at least two separate fly ash streams, including fine fly ash and coarse fly ash;
collecting the fine fly ash and the coarse fly ash, the fine fly ash having a D90 approximately equal to or less than the D50 of the initial fly ash and a conforming carbon content and a conforming reactivity index as defined by ASTM C-618; and
blending the fine fly ash with an aluminosilicate source to form a modified fine fly ash.

US Pat. No. 10,968,136

TEMPERED GLASS

NIPPON ELECTRIC GLASS CO....

1. A tempered glass, comprising, on a surface thereof, a compressive stress layer having a compressive stress, and comprising a tensile stress layer having a tensile stress inside the compressive stress layer,wherein the tempered glass satisfies the following expression (1):
DZ/DT<0.65  (1)where DZ represents a zero stress depth (?m) indicating a depth from the surface to a reference position at which a stress becomes zero between the compressive stress layer and the tensile stress layer, and DT represents an alkali metal diffusion depth (?m) indicating a depth of a region layer, which has diffused therein an alkali metal ion that causes the compressive stress, from the surface, andwherein the tempered glass satisfies the following expression (2):
CTM<73  (2)where CTM represents a maximum tensile stress (MPa).

US Pat. No. 10,968,135

LEAD-FREE GLASS COMPOSITION, AND GLASS COMPOSITE MATERIAL, GLASS PASTE, AND SEALING STRUCTURE BODY CONTAINING THE SAME

Showa Denko Materials Co....

1. A lead-free glass composition which contains vanadium oxide, tellurium oxide, alkali metal oxide, iron oxide, barium oxide, and tungsten oxide while containing substantially no phosphorus oxide, the lead-free glass composition further containing at least one of additional components including yttrium oxide, lanthanum oxide, cerium oxide, erbium oxide, ytterbium oxide, aluminum oxide, and gallium oxide,wherein a content of the tellurium oxide is equal to or more than 25 mol %, and equal to or less than 43 mol % in terms of the oxide TeO2; and
a content of the alkali metal oxide is equal to or more than 4 mol %, and equal to or less than 27 mol % in terms of the oxide R2O (R: alkali metal element).

US Pat. No. 10,968,133

METHODS FOR MINIMIZING SHR IN GLASS ARTICLES BY PRODUCING A GAS FLOW DURING PHARMACEUTICAL PART CONVERTING

CORNING INCORPORATED, Co...

1. A method for producing an article from a glass tube having an inner surface, the method comprising:introducing the glass tube to a converter having a plurality of processing stations comprising at least one heating station, at least one forming station, and a separating station;
heating a proximal end of the glass tube at the at least one heating station, wherein alkali is released from the glass tube during the heating;
forming at least one feature of the article at the proximal end of the glass tube in the at least one forming station;
separating the article from the proximal end of the glass tube at the separating station; and
producing a flow of gas adjacent to the proximal end of the glass tube by introducing a gas pulse into the glass tube through a distal end of the glass tube, wherein:
the gas pulse is introduced in one or more of the plurality of processing stations or between any two of the plurality of processing stations; and
the flow of gas is operable to remove at least a portion of the atmosphere in an interior of the glass tube.

US Pat. No. 10,968,132

LITHIUM SILICATE GLASS CERAMIC FOR FABRICATION OF DENTAL APPLIANCES

James R. Glidewell Dental...

1. A method of making a dental restoration comprising:obtaining a lithium silicate glass ceramic blank comprising silicon dioxide (SiO2), lithium oxide (Li2O), and germanium oxide (GeO2), wherein a molar ratio of SiO2/Li2O is between 1.8 and 1.9;
subjecting the lithium silicate glass ceramic blank to a crystal nucleation process;
milling the lithium silicate glass ceramic blank into a shape of a dental restoration to obtain a pre-crystallized lithium silicate glass ceramic dental restoration; and
heating the pre-crystallized lithium silicate glass ceramic dental restoration at a temperature sufficient to cause crystallization of the lithium silicate glass ceramic and to thereby obtain a crystallized lithium silicate glass ceramic dental restoration.

US Pat. No. 10,968,131

METHOD FOR MANUFACTURING GLASS CONTAINER

KOA GLASS CO., LTD., Tok...

1. A method for manufacturing a glass container comprising steps (A) to (E);(A) A step of introducing a gob into a mold through a funnel after fitting the funnel to the mold,
(B) A step of blowing air into the mold through the funnel, bringing a plunger disposed on a side opposite the side to which the funnel is fitted in contact with the gob, separating the plunger from the gob, and forming a recess on the surface of the gob, the recess formed on the surface of the gob having a maximum diameter of a value within the range of 4 to 24 mm and a depth of a value within the range of 3 to 10 mm,
(C) A step of removing the funnel from the mold and fitting a baffle to the mold,
(D) A step of blowing air from the plunger, and forming an inner space inside the gob with the recess as a starting point while simultaneously forming an outer shape by pressing the outer side of the gob to a molding surface of the mold to obtain a glass container of the final shape, wherein
the inner space formed inside the gob includes a passage portion formed in communication with the outside and an accommodating portion formed continuously from the innermost end portion of the passage portion,
the passage portion has a cylindrical shape and the accommodating portion has a spherical shape,
the following relational expression (1) is satisfied in a case where the passage portion has a cylinder diameter C (mm) and the accommodating portion has a sphere diameter B (mm)
7?B?C?15  (1),
(E) A step of transferring the glass container of the final shape to a cooling mold and cooling the same.

US Pat. No. 10,968,130

METHOD AND DEVICE FOR TREATING WASTEWATER CONTAINING ORGANIC MATTER AND/OR WET WASTE CONTAINING ORGANIC MATTER, IN PARTICULAR FOR TREATING SANITARY WASTEWATER IN TRAINS

1. Method for treating sanitary wastewater (15) in trains, characterized bya) purifying the sanitary wastewater (15) in a bioreactor (20),
b) feeding the wastewater (24), at least partially purified in the bioreactor (20), into a conditioning plant (30),
c) at least partial phase separation of the partially purified wastewater (24) in the conditioning plant (30),
d) obtaining a liquid portion and a solid portion of the at least partially purified wastewater (24), whereby
the conditioning plant comprises a vacuum evaporator (40) and in step c) the partially purified wastewater (24) is concentrated and the vacuum evaporator (40), is operated at a temperature of 25° C. to 35° C., wherein the vacuum evaporator (40) is supplied with waste heat from the bioreactor (20) and the partially purified wastewater (24) is heated by means of the waste heat from the bioreactor (20) and
the liquid portion of the at least partially purified wastewater (24) is transported to a train sanitary installation and used as service water.

US Pat. No. 10,968,129

MINIMIZING WASTES: METHOD FOR DE-OILING, DE-SCALING AND DISTILLING SOURCE WATER

1. A method for de-scaling a saline stream that comprises calcium, bicarbonate, magnesium, or silica, and combinations thereof; said method comprising:(a) mixing said saline stream with an aluminum source and releasing the mixture in a first flashing stage to be contacted with a heat source and a first portion of an organic hydroxide source to form a first precipitate comprising calcium carboaluminate, recover the first portion of said organic hydroxide source, and produce first heated brine; and
(b) releasing said first heated brine in a second flashing stage to be contacted with a second portion of said organic hydroxide source to form a second precipitate comprising magnesium hydroxide, magnesium silicates, or magnesium silicoaluminate, and combinations thereof, recover the second portion of said organic hydroxide source, and produce de-scaled heated brine.

US Pat. No. 10,968,128

POWER GENERATION PROCESS

1. A process for the generation of power, the process comprising the steps of:receiving a wastewater stream containing organic matter;
passing the wastewater stream to an anaerobic digester in which the organic matter contained therein is broken down to produce biogas; and
wherein the liquid content of said wastewater stream is reduced before said stream enters the anaerobic digester by passing the wastewater stream through an osmotic power unit in which said stream is passed over one side of a semi-permeable membrane which permits the passage of water but not the passage of salts, an aqueous stream of higher salinity than said wastewater stream being passed over the other side of said membrane such that latent osmotic energy present in said aqueous stream of higher salinity is converted into electricity and wherein the process further comprises extracting a warm saline stream from a geothermal formation and using said saline stream as the aqueous stream of higher salinity.

US Pat. No. 10,968,127

PHOSPHORUS RELEASE REACTOR FOR WATER TREATMENT

Des Moines Metropolitan W...

1. A method of phosphorus and/or magnesium removal comprising:a. providing an influent stream to a plug flow reactor, wherein the influent stream is a waste activated sludge and/or activated sludge mixed liquor;
b. allowing the influent stream to pass through at least two zones of the plug flow reactor;
c. passing the influent stream through a first zone, wherein concurrent thickening and denitrification occurs; then
d. passing the influent stream though a second zone, wherein further thickening, volatile fatty acid production, and/or phosphorus and/or magnesium release occurs; then
e. passing the influent stream through a final zone, wherein solids separation occurs; and
f. removing phosphorus and/or magnesium from the influent stream, wherein the removal is performed by holding the influent stream in the reactor for a defined period of time so that the hydraulic retention time of the reactor is decoupled from the solids retention time of the reactor, and wherein the phosphorus and/or magnesium is released from phosphorus accumulating organisms;
g. removing a phosphorus and/or magnesium enriched effluent stream from the plug flow reactor.

US Pat. No. 10,968,126

PRETREATMENT OF PRODUCED WATER TO FACILITATE IMPROVED METAL EXTRACTION

Katz Water Tech, LLC, Ho...

1. A produced water treatment method comprising:introducing produced water into a unit to subject the produced water to micro gas bubbles, the unit selected from the group consisting of flocculation dissolved gas floatation, dissolved air floatation, induced gas floatation, froth floatation and combinations thereof to remove contaminates and concentrate lithium;
adding coagulants and pH control to precipitate magnesium and calcium compounds;
removing of magnesium and calcium compounds;
introducing the produced water and particular microorganisms into a second vessel of a moving bed biofilm reactor to be disposed on carriers in the second vessel;
introducing nutrients into the second vessel for the microorganisms;
concurrently subjecting produced water that includes organic materials therein, in the second vessel, to:
a biological water treatment process that removes a first set of organic materials from the produced water, wherein the biological water treatment process comprises removing the first set of organic materials by the microorganisms, the first set of organic materials comprise aqueous phase organic materials, wherein the carriers are circulating in the produced water; and
a physical water treatment process that removes a second set of organic materials from the produced water.

US Pat. No. 10,968,124

METHOD FOR CHANGING FILLER POLLUTANT ACCUMULATION OF CONSTRUCTED WETLAND

Dalian University of Tech...

1. A method for changing filler pollutant accumulation of a constructed wetland, wherein a coupling system of a microbial fuel cell and a constructed wetland is firstly constructed, and the coupling system comprises an anode, an electron collection filler cathode, a constructed wetland emergent aquatic plant and an external circuit; the anode is a graphite plate (1), and is buried in zeolite (2); the electron collection filler cathode is a titanium mesh (5), and the titanium mesh (5) is square with an opening at the top thereof and is positioned above the zeolite (2) for packaging a filler layer; the filler layer is filled with columnar active carbon (3) particles; a titanium mesh tube (4) filled with active carbon particles is placed at the middle position of the filler layer and is used for sampling and measuring pollution, and the constructed wetland emergent aquatic plant is planted on the filler layer; the external circuit is connected with a titanium wire, the anode and the cathode are connected, and a closed loop is formed by a loaded resistor (7), whereinthe method is based on the coupling system, uses a microbial fuel cell to change the filler pollutant accumulation of the constructed wetland, and comprises the following steps:
step 1, constructing a coupling system of a microbial fuel cell and a constructed wetland, and starting the coupling system:
a coupling device of a microbial fuel cell and a constructed wetland is constructed, and inoculation is carried out on the coupling device with pond water so that microorganisms are adhered to the graphite plate (1) to generate an electricity generation biological film; pond water enters into the coupling device from the top of the device in an intermittent mode, sewage firstly goes through an active carbon filler layer to adsorb and intercept suspended particles, then goes through the titanium mesh (5) and then goes through a zeolite layer to reach the anode, soluble organic matters are mainly degraded by electricity generation microorganisms at the anode, and electrons and protons are generated; the electrons are transmitted to the cathode through the external circuit, and the protons going through the zeolite to reach the cathode are combined with the electrons and oxygen to form water, so that a cathode reduction reaction is completed;
when a maximum voltage appears and the coupling device can operate stably, an electricity generation biological film is formed, and the coupling system is started successfully; the voltage at two ends of the resistor is measured every day, and the water quality is measured once every three days;
step 2, performing stable operation of the coupling system and measuring active carbon samples:
after the coupling system is started successfully, pond sewage is supplemented once every seven to ten days so that a water surface reaches an initial water surface; no water outlet is formed in the device, and water is reduced by evaporation mainly; after the system operates for a period of time, an active carbon sample at the bottom inside the titanium mesh tube, namely at a position close to the titanium mesh, and an active carbon sample on a near-surface layer, namely at a position close to the water surface, are taken out for carrying out specific surface area and biomass measurement so as to obtain an accumulation distribution condition of pollutants inside the constructed wetland; and the accumulation distribution condition of pollutants inside the constructed wetland can be changed by using the effect of an electric field generated by the electrons collected by the titanium mesh while electricity is generated and sewage is treated.

US Pat. No. 10,968,123

CATALYTIC WATER TREATMENT WITH IN-SITU PRODUCTION OF HYDROGEN PEROXIDE

UNIVERSITY COLLEGE CARDIF...

1. A water treatment process comprising:contacting contaminated water with a catalyst,
introducing hydrogen and an oxygen-containing gas into the contaminated water, and
reacting hydrogen and oxygen at a temperature of from ?20° C. to 50° C. in the presence of the catalyst and the contaminated water to generate radical species that react with contaminants in the water, wherein the radical species include hydrogen radicals.

US Pat. No. 10,968,122

RECOVERY OF METALS FROM INDUSTRIAL WASTEWATER OF LOW METAL CONCENTRATION

1. A method for recovering non-ferrous metals from industrial wastewater, comprising:A: complexing the metal to be recovered by adding siderophores to the industrial wastewater;
B: separating the metal-siderophore complex;
C: releasing the metal from the metal-siderophore complex;
D: separating the metal;
E: recovering the siderophore; and
F: separating the siderophore,
wherein either:
C: releasing the metal from the metal-siderophore complex is executed via adding Fe(III) ions and forming an Fe(III)-siderophore complex; and
E: recovering the siderophore is executed via adding a reductant and/or a chelator or
C: releasing the metal from the metal-siderophore complex is executed via adding a chelator, as a result of which a metal-chelator complex is formed; and
D: the metal is separated as this metal-chelator complex.

US Pat. No. 10,968,121

PROCESS FOR THE TREATMENT OF PRODUCED WATER FROM CHEMICAL ENHANCED OIL RECOVERY

ChampionX USA Inc., Suga...

1. A process for the treatment of produced water from polymer flood chemical enhanced oil recovery, said process comprising:providing produced water (110) comprising water, an anionic polymer and oil;
first treating the produced water with a first reagent (160) to provide first treated produced water (120);
second treating the first treated produced water with a second reagent (260) to provide second treated produced water (220) comprising water and agglomerates comprising oil, anionic polymer, first reagent and second reagent; and
separating the water and agglomerates of the second treated produced water to provide treated water (310) and separated agglomerates (320);
wherein, the first and second reagents are added separately so that the first and second treating steps are separated by a period of at least 30 seconds;
the first reagent comprises a water-soluble dithiocarbamate polymer comprising dithiocarbamate groups and dithiocarbamate salt groups and has a molecular weight of 500 or more, and
the second reagent comprises a metal ion selected from the group comprising a cation of a transition metal, aluminum and lead.

US Pat. No. 10,968,120

APPARATUS AND METHOD FOR ELECTRODISINFECTION

e2metrix Inc., Sherbrook...

1. An electrolytic apparatus assembly for the electro-disinfection of water from a cooling tower, the apparatus comprising:at least one vertical electrolytic unit, each unit comprising:
a vertical tubular reactor having a bottom section and a top section,
an inlet adjacent to the bottom section of the reactor for injecting water to be treated into the reactor,
an outlet adjacent to the top section of the reactor for extracting the water from the reactor,
a plurality of anodes being rods extending longitudinally from the top section of the reactor inside the reactor;
at least one cathode located inside the reactor; the plurality of anodes and the at least one cathode being configured to be operatively connected to an electric power supply providing a continuous current to the anodes and the at least one cathode to electrolyze the water flowing inside the reactor for at least partially kill bacteria present in the water;
wherein each anode is a Dimensionnally Stable Anode (DSA); and
a pump unit operatively connected to the inlet for injecting the water to be treated into the reactor, wherein the pump unit is fluidly connected to the cooling tower in order to extract and treat water that have previously circulated within the cooling tower; the outlet of the reactor being fluidly connected to the same cooling tower for re-injecting the water into the cooling tower after treatment, the electrolytic apparatus assembly and the cooling tower forming a treatment loop.

US Pat. No. 10,968,118

SUBSEA EQUIPMENT CLEANING SYSTEM AND METHOD

VETCO GRAY SCANDINAVIA AS...

1. A subsea water processing system comprising:at least one underwater membrane separation module of a water injection system arranged in a feed line from a seawater or oil field produced water intake to a water injection pump;
an electrochemical acid and base generation unit operable for on-site generation of high PH and low PH cleaning solutions using seawater or oil field produced water in an electrochemical process; and
acid or base flow lines and valves connecting the electrochemical acid and base generation unit on-site with the at least one underwater membrane separation module to supply high PH and low PH cleaning solutions for circulation through the at least one underwater membrane separation module during a membrane cleaning cycle.

US Pat. No. 10,968,117

ELECTROSORPTION PURIFICATION SYSTEM WITH RECIRCULATION

KONINKLIJKE PHILIPS N.V.,...

1. A deionization system configured to deionize an aqueous liquid, wherein the deionization system comprises:a recirculation loop comprising a first loop inlet, a first loop outlet for waste liquid and a second loop outlet for purified aqueous liquid;
a flow generation apparatus configured to generate flow of the aqueous liquid in the deionization system;
an electrosorption cell unit comprising a treatment section for said aqueous liquid, wherein the treatment section comprises (a) a first electrosorption electrode arrangement comprising a first electrosorption electrode, (b) a second electrosorption electrode arrangement comprising a second electrosorption electrode, (c) a first treatment section opening for introduction of the aqueous liquid from the recirculation loop, and (d) a second treatment section opening for releasing aqueous liquid into the recirculation loop, and wherein the treatment section is configured downstream from the first loop inlet and upstream of the second loop outlet based on a flow starting at the first loop inlet, flowing through the recirculation loop and ending at the first loop inlet after a single recirculation;
a first loop part, in the recirculation loop, downstream from the electrosorption cell unit and upstream from the first loop outlet, the first loop part having a first volume (V1); and
a second loop part, in the recirculation loop, downstream from the electrosorption cell unit and upstream from the second loop outlet, the second loop part having a second volume (V2), wherein V1/V2<0.5.

US Pat. No. 10,968,116

LIQUID TREATMENT SYSTEM

Wallenius Water Innovatio...

1. A liquid treatment system, comprising:at least one ultra-violet (UV) light treatment lamp arranged within an elongated protective UV-transparent sleeve provided along a central longitudinal axis A, said elongated protective UV-transparent sleeve having an outer surface and an essentially circular cross-sectional shape; and
an elongated reactor configured to receive said elongated protective UV-transparent sleeve, whereby an elongated liquid treatment chamber for receiving liquid to be treated, is provided between an inner surface of the elongated reactor and the outer surface of the elongated protective UV-transparent sleeve; and
at least one elongated cleaning device provided side by side with the elongated protective UV-transparent sleeve within the elongated liquid treatment chamber and along at least a part of a length of the elongated protective UV-transparent sleeve,
wherein said at least one elongated cleaning device is compressed towards the outer surface of the elongated protective UV-transparent sleeve by the elongated reactor, and wherein at least one of the elongated protective UV-transparent sleeve and the elongated reactor is configured to rotate around the central longitudinal axis A such that the at least one elongated cleaning device will be touching and cleaning the outer surface of the elongated protective UV-transparent sleeve over essentially a whole circumference of the elongated protective UV-transparent sleeve,
wherein the elongated reactor has a partly circular cross-sectional shape with at least one part having an extended inner and outer radius where the at least one elongated cleaning device is provided.

US Pat. No. 10,968,115

WATER DISINFECTION METHOD AND WATER TAPPING POINT ARRANGEMENT THEREFOR

Q One Holding AG, Sarnen...

1. A method for the disinfection of water by means of UV irradiation in water supply systems in buildings or ships having a water tapping point (1) flexibly connected to a hose, and a water tapping point mount (2) for receiving (21) the water tapping point (1) when not in use, where the UV radiation takes place at the water tapping point (1), the method comprising:providing a means for UV-irradiation (3) in the water tapping point mount (2),
depositing the water tapping point (1) in the water tapping point mount (2) after use of the water tapping point (1),
directing UV-irradiation from the water tapping point mount (2) to the water tapping point (1) while the water tapping point (1) is received in the water tapping point mount (2).

US Pat. No. 10,968,114

WATER RECYCLING SYSTEM AND METHOD

1. A device for detecting untreated grey water quality, the device comprising:a first operational sensor that detects an impurity in untreated grey water, wherein the untreated grey water flows through a plumbing system of a building;
a second operational sensor that detects the impurity in the untreated grey water, wherein the untreated grey water flows through the plumbing system of the building;
a directional device associated with said first operational sensor and said second operational sensor, wherein the directional device routes the untreated grey water into a water heating device and a first output filter, wherein the untreated grey water passes through the first output filter as an output of treated grey water;
and an output sensor associated with said first operational sensor, said second operational sensor, and the directional device, wherein the output sensor routes the treated grey water to a plurality of treated grey water tanks for storage prior to reuse in the plumbing system of the building if the treated grey water contains an impurity at or below a threshold for an acceptable impurity level, wherein the output sensor routes the treated grey water to a sewer line through the plumbing system of the building if the treated grey water contains an impurity above the threshold for an acceptable impurity level, or wherein the output sensor shuts down the device if the treated grey water contains an impurity above the threshold for an acceptable impurity level;
further comprising a computer panel configured to receive input on which of the plurality of treated grey water tanks is to be filled with the treated grey water;
said computer panel further configured to receive input that the plurality of treated grey water tanks be filled in sequence with the treated grey water, wherein a first treated grey water tank is filled to capacity with the treated grey water, thereafter a second treated grey water tank is filled to capacity with the treated grey water, thereafter a third treated grey water tank is filled to capacity with the treated grey water;
said computer panel further configured to receive input that the plurality of treated grey water tanks will be filled equally until the first treated grey water tank, the second treated grey water tank, and the third treated grey water tank reach capacity at the same time; and
said computer panel further comprising a switch configured to receive input that will bypass the device and return the plumbing system of the building to its original functionality.

US Pat. No. 10,968,113

LEAD EXPOSURE ASSESSMENT DEVICE

GOVERNMENT OF THE UNITED ...

1. A device comprising:(a) an inlet to receive a lead-containing aqueous feed;
(b) an outlet to discharge a lead-depleted treated aqueous feed;
(c) at least one cartridge positioned so that the lead-containing aqueous feed passes from the inlet and through the cartridge to produce the lead-depleted treated aqueous feed for discharge through the outlet,
(d) a flowmeter configured to calculate the total flow of aqueous feed during a designated time period;
(e) a flow totalizer configured to quantify the amount of water that passes through the device while lead is accumulated in the cartridge over a given period of time,
wherein the cartridge contains sampling media,
the lead comprises both particulate lead and soluble lead, and
the device is configured to determine the average levels of lead in the aqueous feed, to quantify the average lead exposure of humans to the aqueous feed, to remove lead from the aqueous feed, and to identify the presence of lead service lines.

US Pat. No. 10,968,112

METHOD FOR PRODUCING HIGH-PURITY SCANDIUM OXIDE

SUMITOMO METAL MINING CO....

1. A method for producing high-purity scandium oxide, the method comprising:a first calcination step of subjecting a solution containing scandium to an oxalate formation treatment using oxalic acid and calcinating crystals of obtained scandium oxalate at a temperature of 400° C. to 600° C.;
a dissolution step of dissolving a scandium compound obtained by calcinating, in at least one selected from hydrochloric acid and nitric acid to obtain a solution;
a reprecipitation step of subjecting the solution to an oxalate formation treatment using oxalic acid to generate a reprecipitation product of scandium oxalate; and
a second calcination step of calcinating the obtained reprecipitation product of scandium oxalate to obtain scandium oxide.

US Pat. No. 10,968,111

ALUMINA PRODUCTS AND USES THEREOF IN POLYMER COMPOSITIONS WITH HIGH THERMAL CONDUCTIVITY

Martinswerk GmbH, Berghe...

1. An alumina product having a fine alumina particle size component and a coarse alumina particle size component, wherein:the fine alumina particle size component has a d50 particle size in a range from 0.8 to 4.5 ?m, and is characterized by a BET surface area in a range from 0.5 to 8 m2/g;
the coarse alumina particle size component has a d50 particle size in a range from 10 to 35 ?m, and is characterized by a BET surface area in a range from 0.1 to 1.5 m2/g and an average aspect ratio in a range from 1.5 to 30; and
the amount of the fine alumina particle size component in the alumina product is from 10 to 90 wt. %, based on the total weight of the fine alumina particle size component and the coarse alumina particle size component.

US Pat. No. 10,968,110

METHOD FOR PREPARING TITANIUM SILICON MOLECULAR SIEVE

CHINA UNIVERSITY OF PETRO...

1. A method for preparing a titanium-containing molecular sieve, comprising the following steps: irradiating a mixed solution containing a silicon source, a template and a titanium source by a light source containing ultraviolet light before crystallization, and then subjecting the mixed solution to the crystallization and post-treatment to obtain the titanium-containing molecular sieve, wherein the time for irradiating by the light source containing the ultraviolet light is longer than the shortest time required for the ultraviolet light to decompose the titanium source, and is shorter than the time for self-polymerization of a titanium monomer.

US Pat. No. 10,968,109

METHOD FOR SYNTHESIZING MORDENITE MOR MOLECULAR SIEVE, AND PRODUCT AND USE THEREOF

DALIAN INSTITUTE OF CHEMI...

1. A method for synthesizing a mordenite MOR molecular sieve with B acid sites being located in an 8-membered ring side pocket in the presence of an inorganic base, the method comprises:a) mixing an aluminum source in terms of Al2O3, a silicon source in terms of SiO2, an inorganic base M2O, an additional reagent N, and water H2O to form an initial mixture A with the following molar ratio composition:
Al2O3:SiO2=0.005 to 0.1:1
M2O:SiO2=0.05 to 1:1
N:SiO2=0.1 to 1:1
H2O:SiO2=5 to 60:1;
b) adding a seed crystal S of mordenite MOR molecular sieve into the initial mixture A obtained in step a), and stirring uniformly to obtain an initial gel B, wherein the mass ratio of the added seed crystal S to SiO2 contained in the initial mixture A is S:SiO2=0.005 to 0.1:1;
c) crystallizing the initial gel B obtained in step b) at a temperature in a range from 120° C. to 200° C. under autogenous pressure for 12 hours to 240 hours;
d) filtering the solid product, separating and washing the solid product to neutral with deionized water after the crystallization is completed, and then drying the solid product to obtain the mordenite MOR molecular sieve,
wherein M in the inorganic base M2O represents an alkali metal; the additional reagent N matches with the channel size of the 8-membered ring side pocket and is one or more selected from the group consisting of methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, N-methyldiethylamine, N,N-dimethylethylamine, N-methylethylenediamine, N,N-dimethylethylenediamine, N,N,N-trimethylethylenediamine, N-ethylethylenediamine, N,N-diethylethylenediamine, N,N,N-triethylethylenediamine, N-methyl-N,N-diethylethylenediamine, N,N dimethyl-N-ethylethylenediamine, N,N,N,N-tetramethylethylenediamine, n-propylamine, di-n-propylamine, isopropylamine, tetramethylammonium hydroxide, tetramethylammonium bromide, tetramethylammonium chloride, tetramethylammonium iodide, methanol, ethanol, n-propanol and isopropanol.

US Pat. No. 10,968,108

METHOD FOR THE MANUFACTURE OF CALCIUM SILICATE HYDRATE USED AS HARDENING ACCELERATOR IN CONCRETE AND CEMENT-BASED MATERIALS, CALCIUM SILICATE HYDRATE MANUFACTURED WITH SAID METHOD

1. A process for the manufacturing of a slurry containing nucleating agents which comprises reacting at least one source of a Ca containing compound with at least one source of a Si containing compound, in an aqueous media and in the presence of a doping agent selected from the group consisting of a compound containing P, a compound containing B, and mixtures thereof; wherein:(i) the reaction is a hydrothermal reaction carried out at a temperature from 140 to 250° C. and endogenous pressure;
(ii) the total molar ratio of Ca to Si is from 1.8 to 2.4, and
(iii) the total molar ratio of doping agent to Si is from 0.01 to 2; provided that:
(a) when the sole doping agent is a compound containing P, the total molar ratio of P to Si is from 0.1 to 2; and
(b) when the sole doping agent is a compound containing B, the total molar ratio of B to Si is from 0.01 to 2,
wherein the nucleating agents comprise Calcium Silicate Hydrate (C-S-H) in the form of defective tobermorite.

US Pat. No. 10,968,107

METHOD FOR PREPARING SILICON AND/OR GERMANIUM NANOWIRES

1. Method for preparing a material made of silicon and/or germanium nanowires, that comprises the steps of:i) placing a silicon source and/or a germanium source in contact with a catalyst comprising a binary metal sulfide or a multinary metal sulfide, said metal(s) being selected from Sn, In, Bi, Sb, and Ga, by means of which the silicon and/or germanium nanowires are obtained,
ii) optionally recovering the silicon and/or germanium nanowires obtained in step (i);
the catalyst, and optionally the silicon source and/or the germanium source, being heated before, during, and/or after the placing in contact under temperature and pressure conditions allowing the growth of silicon and/or germanium nanowires, the heating being done at a temperature of between 200° C. and 500° C.

US Pat. No. 10,968,106

PRODUCTION OF SI/C COMPOSITE PARTICLES

Wacker Chemie AG, Munich...

1. A method for producing precomposite particles, comprising:dry mixing silicon particles; polyacrylonitrile particles; and one or more carbon additives selected from the group consisting of graphite, fullerene, carbon fibers, glassy carbon, graphene, activated carbon, carbon blacks, carbon nanotubes, carbon nanofoams, and aerographite; optionally one or more organic pore formers, and optionally one or more inorganic adjuvants,
wherein before and during the dry mixing no solvent is added, wherein the inorganic adjuvants are selected from the group consisting of halides of alkali metals and alkaline earth metals, carbonates of alkali metals, zinc oxide, magnesium carbonate, and nickel sulfide, and
wherein the polyacrylonitrile, the silicon particles and/or the carbon additives are entirely or partially initially introduced before the mixing or entirely or partially metered in during the mixing,
with the proviso that if polyacrylonitrile is not present initially, the silicon particles and/or the carbon additives are metered in at least proportionately together with polyacrylonitrile or after addition of polyacrylonitrile,the precomposite particles, when thermally treated, form Si/C composite particles with a degree of aggregation of less than 20%.

US Pat. No. 10,968,105

LOW-TEMPERATURE PYROLYSIS OF ORGANIC ACID SALTS PROVIDING GRAPHENE RICH CARBONS

Board of Regents, The Uni...

1. A method of forming a carbonaceous material, the method comprising:heating, in the absence of air or oxygen, a salt comprising carbon, oxygen, and one or more metal ions to a temperature between about 500° C. and about 875° C. to drive a chemical reaction involving the salt to form reaction products including the carbonaceous material and a carbon templating hexagonal metal oxide, the carbonaceous material comprising graphene sheets;
contacting the reaction products with an organic acid or a mineral acid to dissolve the hexagonal metal oxide and form a liquid phase and a solid phase, the liquid phase comprising the metal ions and the solid phase comprising the carbonaceous material;
separating the liquid phase and the solid phase; and
drying the solid phase to form a dried carbonaceous material.

US Pat. No. 10,968,104

METHOD FOR PRODUCING SHEETS OF GRAPHENE

Universidade De Santiago ...

1. A method for obtaining a sheet of graphene, boron nitride, molybdenum disulfide, tungsten disulfide or mixtures thereof, wherein said sheet consists of a set of strips, wherein each strip consists of between one and five layers of graphene, boron nitride, molybdenum disulfide or tungsten disulfide, wherein said layers have monoatomic or monomolecular thickness, and wherein said method comprises:a) placing powder of at least one multilayer material selected from the group consisting of graphite, boron nitride, molybdenum disulfide and tungsten disulfide, between two solid substrates, wherein at least one of said solid substrates has a roughness between 0.2 and 2 nm; and
b) rubbing the surfaces of said substrates between them and with said powder, wherein said powder is placed between said surfaces,to form said sheet on the surface of at least one solid substrate.

US Pat. No. 10,968,103

COPPER-FILLED CARBON NANOTUBES AND SYNTHESIS METHODS THEREOF

The Florida International...

1. A method of synthesizing copper (Cu)-filled carbon nanotubes (CNTs), the method comprising:providing a Cu substrate in a reaction chamber;
heating the reaction chamber to a predetermined growth temperature;
providing a carbon precursor gas to the reaction chamber;
forming a carbon layer on the Cu substrate; and
performing a plasma-enhanced chemical vapor deposition (PECVD) technique for a predetermined amount of time to simultaneously grow CNTs directly on the Cu substrate and fill the CNTs with Cu, thereby synthesizing the Cu-filled CNTs on the Cu substrate, the Cu filling the CNTs and extending from tips thereof during the PECVD technique, and the Cu substrate becoming porous during the PECVD technique,
the CNTs having a filling rate of at least 70%, and
the Cu substrate being a Cu disk, a Cu foil, or a Cu plate.

US Pat. No. 10,968,102

METHOD FOR PRODUCING BLACK PHOSPHORUS

1. A method of producing black phosphorus, comprising the steps of:(a) weighing reaction raw materials which comprises metallic tin, red phosphorus and monocrystalline iodine, wherein a weight ratio of tin: red phosphorus: iodine is 0.6-3.5: 5-45: 0.1-0.8;
(b) mixing the reaction raw materials uniformly to form a mixture;
(c) feeding the mixture to a glass tube, replacing air inside the glass tube by inert gas, closing a glass tube opening of the glass tube by a plug and then placing the glass tube inside a high-temperature resistant metal reaction tube;
(d) introducing inert gas to the high-temperature resistant metal reaction tube to replace air inside the high-temperature resistant metal reaction tube with the inert gas;
(e) closing and sealing the metal reaction tube tightly; and
(f) placing the metal reaction tube inside a muffle furnace for carrying out calcination reaction by controlling a temperature increase at a rate 50-80° C./h from room temperature to a first reaction temperature, a second reaction temperature and then a third reaction temperature sequentially, and then by controlling a temperature decrease at a rate of 40-80° C./h to a first cooling temperature, a second cooling temperature, and finally to the room temperature sequentially, then obtaining a final product of black phosphorus,
wherein the third reaction temperature is greater than the second reaction temperature; and the second reaction temperature is greater than the first reaction temperature; and the first reaction temperature is greater than the room temperature,
wherein after reaching the first reaction temperature, the first reaction temperature is maintained for a first time period, after reaching the second reaction temperature, the second reaction temperature is maintained for a second time period, and after reaching the third reaction temperature, the third reaction temperature is maintained for a third time period,
wherein after reaching the first cooling temperature, the first cooling temperature is maintained for a first cooling time period, after reaching the second cooling temperature, the second cooling temperature is maintained for a second cooling time period,
wherein a total time of the first time period, the second time period and the third time period is approximately 3-8 hours and the third reaction temperature is 520° C.-760° C.,
wherein a weight ratio of tin: red phosphorus: iodine is 0.8-1.5: 15-25: 0.12-0.25, the reaction raw materials further comprise molybdenum or tungsten having a weight of 0.5-1% of a total weight of the reaction raw materials, the third reaction temperature is 580-660° C., and a volume of the high-temperature resistant metal reaction tube is about 1.5-5 times of a volume of the glass tube.

US Pat. No. 10,968,101

OZONE CELL POWER SUPPLY APPARATUS AND METHOD

Pacific Ozone Technology ...

1. For an ozone generation system having an ozone generation cell, a transformer having a high voltage output connected to the ozone generation cell for powering the ozone generation cell, and a power supply connected to an input of the transformer, the ozone generation system having a resonant frequency during operation, a method of operation comprising:driving current and voltage through the transformer and ozone generation cell at a driving frequency to control power delivered by the power supply to the ozone generation cell by the driving frequency;
determining a phase relationship of current and voltage driven through the transformer and ozone generation cell; and
in response to the determined phase relationship, restraining the driving frequency to a range more than the resonant frequency of the ozone generation system.

US Pat. No. 10,968,100

METHOD FOR PRODUCING SYNTHESIS GAS BY MEANS OF STEAM REFORMING REACTORS

1. A process for producing synthesis gas using at least a first and a second steam reforming reactor each comprising at least one reaction stage enabling the circulation of a reaction mixture and at least one heat supply stage enabling the circulation of a heat transfer fluid, the process comprising the following steps:a) mixing a hydrocarbon feedstock gas and steam thereby forming the reaction mixture,
b) simultaneously supplying the reaction stages of the first and second steam reforming reactors with the reaction mixture obtained in step a),
c) producing combustion flue gases within the steam reforming reactors, wherein the combustion flue gases are used as heat transfer fluid,
d) cooling the combustion flue gases to a temperature below 1000° C.,
e) introducing the combustion flue gases from step d) into the heat supply stage of the first steam reforming reactor,
f) recovering the combustion flue gases at the outlet of the first steam reforming reactor and introducing them into the heat supply stage of the second steam reforming reactor, and
g) recovering synthesis gas at the outlet of the first and second steam reforming reactors.

US Pat. No. 10,968,099

PACKAGE MOISTURE CONTROL AND LEAK MITIGATION FOR HIGH VACUUM SEALED DEVICES

TEXAS INSTRUMENTS INCORPO...

1. A method of forming a device, the method comprising:in a first substrate having a first surface, forming a cavity in the first surface;
forming a microelectromechanical system (MEMS) component in the cavity, comprising:
forming a first metal layer on or adjacent to a perimeter of the cavity;
forminga second metal layer on the first surface of the first substrate, the second metal layer being adjacent to the first metal layer;
on a second substrate having a second surface, forming a third metal layer and a fourth metal layer on the second surface, the fourth metal layer being spaced from the third metal layer;
placing the first and second substrates in a vacuum environment;
positioning the first and second substrates together, the first metal layer contacting or adjacent to the third metal layer, and the second metal layer contacting or adjacent to the fourth metal layer;
sealing the MEMS component in the cavity by heating the first, second, third and fourth metal layers to form a first metal bond between the first and third metal layers, and to form a second metal bond between the second and fourth metal layers; and
adding a getter agent between the first metal layer and the second metal layer or between the third metal layer and the fourth metal layer before heating the first, second, third and fourth metal layers.

US Pat. No. 10,968,098

SELECTIVE FUNCTIONALIZATION OF SENSING SURFACE WITH NANOSCALE SPATIAL RESOLUTION

INTERNATIONAL BUSINESS MA...

1. A nanoscale selective functionalization method, comprising:self-assembling first molecules to nanowires of transistors provided on a wafer such that the first molecules coat the nanowires;
identifying a transistor as a target transistor and transistors neighboring the target transistor as neighboring transistors;
disassembling the first molecules from the nanowire of the target transistor without disassembling the first molecules from the nanowires of the neighboring transistors; and
self-assembling second molecules to the nanowire of the target transistor such that the second molecules coat the nanowire of the target transistor,
wherein:
the disassembling comprises determining a disassembly temperature to which the target transistor is to be heated to disassemble the first molecules from the corresponding nanowire,
the wafer has spacing between the target and the neighboring transistors and the spacing is sufficient to prevent a heating of the target transistor from heating the neighboring transistors to the disassembly temperature, and
the nanoscale selective functionalization method further comprises:
shielding at least one of the target transistors and the neighboring transistors during a heating of the target transistors to prevent an unwanted heating of the neighboring transistors; and
reducing the spacing between the at least one of the target transistors with the shielding and the neighboring transistors,
wherein the shielding comprises interposing FET-shaped shields consisting of tungsten (W) between the target transistors and the neighboring transistors.

US Pat. No. 10,968,097

SUPPORT STRUCTURE FOR MEMS DEVICE WITH PARTICLE FILTER

Taiwan Semiconductor Manu...

1. A microphone comprising:a carrier substrate having opposing sidewalls that define a carrier substrate opening;
a microelectromechanical systems (MEMS) structure overlying the carrier substrate, wherein the MEMS structure includes a diaphragm having opposing sidewalls that define a diaphragm opening overlying the carrier substrate opening;
a filter stack disposed between the carrier substrate and the MEMS structure, wherein the filter stack includes a particle filter layer having a particle filter, wherein a plurality of filter openings extend through the particle filter; and
a support structure layer disposed between the particle filter and the MEMS structure, wherein the support structure layer comprises a support structure having first elongated support segments extending between a first pair of opposing inner sidewalls of the support structure layer, wherein the first elongated support segments are spaced laterally between the opposing sidewalls of the carrier substrate, and wherein the first elongated support segments respectively comprise opposing straight sidewalls that continuously extend between the first pair of opposing inner sidewalls of the support structure layer.

US Pat. No. 10,968,096

MICROELECTRONIC SENSOR DEVICE WITH AN OUT-OF-PLANE DETECTION HAVING A CONTROLLED CROSS SENSITIVITY

1. Microelectromechanical sensor with an out-of-plane detection having a cross sensitivity in a first direction in the plane with a value ST, said sensor comprising a support, an inertial mass suspended from the support by suspension means, a first axis of rotation about which the inertial mass pivots with respect to the support in an out-of-plane direction when the sensor is subjected to a stress in the out-of-plane direction, said suspension means comprising at least one first beam in the plane, said at least one first beam being anchored by a longitudinal end to the support and by another longitudinal end to the inertial mass, in such a way that during a movement of the inertial mass in the out-of-plane direction, said at least first beam is stressed by bending, and means for detection of the movement of the mass in the out-of-plane direction, said detection means comprising at least one first stress gauge suspended by a first end from the inertial mass and by a second end from the support and extending in parallel to said at least one first beam, wherein said to the first beam has a dimension tf in the out-of-plane direction and the inertial mass has a dimension tM in the out-of-plane direction such that
larm being a distance between the centre of gravity of the inertial mass and the centre of the at least one first beam projected onto the first longitudinal direction.

US Pat. No. 10,968,095

CUSTOM BLENDING HOSE FOR MANIFOLD MIXING OF VARIOUS FUELS FOR FUEL DISPENSING SYSTEM

Husky Corporation, Pacif...

1. A custom blending hose and manifold assembly for attaining a predetermined mixing of a first fuel and a second fuel for a fuel dispensing system for a vehicle, including a dispenser, nozzle and dispensing hoses, the custom blending hose and manifold assembly comprising:said manifold assembly including a manifold structure provided within a manifold housing;
said dispensing hoses having an upstream end segment connecting with an entrance to said manifold assembly, and said upstream end segment of said dispensing hoses formed having either concentric or coaxial arranged fuel hoses for delivery of the first and second fuels to said manifold assembly for blending of the first and second fuels;
a unitary manifold structure formed of said manifold structure and said manifold housing, and formed for said manifold assembly, and free of moving components for mixing the first and second fuels together, said dispensing system including said unitary manifold structure provided in said manifold housing having an upstream end connecting with the upstream end segment of the dispensing hoses, with said dispensing hoses conveying separately the first and second fuels to the manifold assembly, with each of the first and second fuels being combined in a region before the manifold assembly and as the fuel passes through said manifold structure of the manifold housing, said manifold housing having a downstream end and connecting with a downstream end fuel dispensing hose for delivery of the blended fuels to the nozzle and dispensing into a fuel tank of said vehicle;
said custom blending hose and manifold assembly including said manifold housing having a series of internal threads within intake end of the manifold housing, for connection of the dispensing hoses, and said manifold housing having an internally threaded opening at an outlet end, for connection with a downstream end fuel dispensing hose;
said manifold structure including a series of apertures formed to allow passage of the first and second fuels for delivery to the manifold structure for mixing of the second fuel with the first fuel and the blended fuels to be delivered to the connected downstream end dispensing hose for delivery of the blended fuels to the nozzle and dispensing into the fuel tank of the vehicle;
said manifold housing includes an outer housing, and an integral internal said manifold structure includes said series of apertures being peripherally arranged within the manifold structure to allow for passage of the blended fuels at increased pressure and quicker velocity during intermixing when passing through said manifold assembly for delivery to the dispensing hose of the fuel dispensing system, said series of apertures being circularly arranged around the perimeter of said manifold structure;
a central aperture in the manifold structure for receiving an internal vapor recovery tube of a vapor recovery system of the fuel dispensing system; and
wherein the manifold assembly can attain a blending of fuels of various grades, different octane ratings, and even different styles, and types of fuels together, as they enter the manifold structure of the assembly to deliver the blended fuel to the fuel tank of the vehicle.

US Pat. No. 10,968,094

UNIVERSAL MANIFOLD FOR DELIVERING HAZARDOUS LIQUID

COLE-PARMER INSTRUMENT CO...

1. A universal manifold system for the delivery and collection of chemical liquid to and from a storage container; the universal manifold system comprising:a storage container, with a fill aperture;
a threaded cap, for attaching to the storage container;
a manifold, for receiving a plurality of supply tubes;
a mating receiving surface, for securing the manifold;
a plurality of screws, for securing into the mating receiving surface of the manifold; and
a plurality of mating washers, whereby a single mating washer, that corresponds with a size of the fill aperture, is removably fixed to the threaded cap and the mating receiving surface.

US Pat. No. 10,968,093

SYSTEM, CARTRIDGE, BEVERAGE PREPARATION UNIT AND METHOD FOR PRODUCING A BEVERAGE

Freezio AG, Amriswil (CH...

1. A system for the production of a beverage comprising:a cartridge which has a reservoir filled with a beverage substance;
a beverage preparation unit having a cartridge receptacle in which the cartridge can be reversibly inserted; and
a cartridge discharge device which causes at least partial transfer of the beverage substance from the reservoir into a mixing chamber;
wherein the beverage preparation unit furthermore comprises a liquid supply which opens into the mixing chamber;
wherein the system comprises a movable plunger which is placed inside the reservoir and can be transferred from a starting position into a final position by means of the cartridge discharge device;
wherein the plunger can be introduced as part of the cartridge discharge device into the reservoir after the cartridge has been inserted into the beverage preparation unit;
wherein the cartridge discharge device comprises a movable ram which can be inserted on an input side of the cartridge into the cartridge in order to press the beverage substance out from the cartridge on an output side of the cartridge;
wherein the cartridge-side end of the ram comprises the plunger;
wherein the cartridge has in a region of an insert side a sealing element which is opened by inserting the plunger;
wherein the sealing element has a sealing film which tears as the plunger is introduced; and
wherein the sealing film is arranged between the plunger located in the starting position, and the beverage substance, so that the sealing film is torn by the plunger as the ram is inserted.

US Pat. No. 10,968,092

DISPENSING APPARATUS WITH VALVE

1. A dispensing apparatus for dispensing a material, comprising:a removable container for holding the material;
a receptacle for receiving the material, the receptacle comprising a top opening and a flange;
a funnel for receiving the material from the removable container and guiding the material to the receptacle, the funnel comprising a valve holder at a lower end of the funnel and a lower opening aligned with the top opening of the receptacle;
a valve member slidably coupled to the valve holder, the valve member comprising a valve aperture;
a valve lever connected to the valve member, wherein when activated, the valve lever is configured to move the valve member to cause the valve aperture to align with the lower opening of the funnel, allowing the material to flow down from the funnel to the receptacle until the receptacle is filled to the top opening;
a lever assembly coupled to the valve lever, wherein the lever assembly is configured to be activated by an operator inserting the flange of the receptacle into the lever assembly, and when activated, the lever assembly is configured to activate the valve lever; and
a gap separating the valve member and the top opening of the receptacle, the gap having a gap width greater than zero and less than a predetermined value, wherein the gap width is chosen according to a first aperture size of a dispending point at the valve aperture, a second aperture size of the top opening of the receptacle, and granular properties of the material to be dispensed such that when the valve lever is activated and the material flows down and fills the receptacle to the top opening, the material further fills the gap, causing the material to stop flowing down.

US Pat. No. 10,968,091

FILLING ELEMENT AND FILLING MACHINE

KHS GmbH, Dortmund (DE)

1. An apparatus comprising a can-filling machine for filling cans with liquid filling-material, said can-filling machine comprisinga rotor that rotates about a vertical machine-axis and that defines filling positions for filling cans,
a filling element disposed in one of said filling positions, said filling element comprising a filling-element housing comprising a first housing-section that defines a liquid channel that extends along a filling-element axis and through said first housing-section to a delivery orifice through which a controlled flow of liquid filling-material enters a can,
a sealing tulip that is movable along said filling-element axis between a raised position, at which said sealing tulip releases said can, and a lowered position, at which said sealing tulip seals against an orifice edge of said can,
a bellows that surrounds said filling-element axis and at least a portion of said filling-element housing and that forms seals with said filling-element housing and said sealing tulip at first and second ends thereof, wherein said bellows seals a transition between said sealing tulip and said filling-element housing, whereby there is no sliding seal to seal said transition between said tulip and said filling-element housing, and
a valve disposed in said liquid channel and configured to control flow of said liquid filling-material through said delivery orifice,
wherein, during operation of said filling element, either a filling pressure or a pre-tensioning pressure acts on inner surfaces of both said sealing tulip and said bellows and also presses said sealing tulip against said orifice edge,
wherein said first housing-section, said tulip, and said bellows cooperate to define an annular gap that extends from a proximal end of said first housing-section to a distal end of said first housing-section, said annular gap having an inner wall formed by an outer surface of said first housing-section and an outer wall having a proximal section formed by an inner face of said bellows and a distal section formed by an inner surface of said sealing tulip,
wherein said can-filling machine further comprises a channel, wherein said channel opens out into said annular gap at a location selected such that liquid cleaning medium that enters through said channel cleans an inner face of said bellows,
wherein said channel comprises an opening that leads into said upper annular gap,
wherein said channel defines a channel axis,
wherein said channel axis forms an angle relative to a plane that is perpendicular to said filling element axis, and
wherein said angle is less than ninety degrees.

US Pat. No. 10,968,090

MODULAR RIB FOR ELEVATING PLATFORM

ALTEC INDUSTRIES, INC., ...

1. A mounting rib on an elevating platform with at least one sidewall cutout comprising:a rib component that includes at least a stem connected to a first arm and a second arm, wherein each arm includes a sidewall contact portion;
wherein the first arm and the second arm extend in opposite and horizontal directions relative to a bottom of the elevating platform;
wherein the sidewall contact portion of the first arm is positioned inside of the elevating platform and contacts an inner surface of the platform sidewall;
wherein the sidewall contact portion of the second arm is positioned outside of the elevating platform and contacts an outer surface of the platform sidewall;
wherein the sidewall contact portion of the first arm and the sidewall contact portion of the second arm create a mechanical interlock holding the rib in place;
wherein the stem extends through the at least one sidewall cutout in the platform sidewall and joins with the second arm on the outside of the platform sidewall;
wherein the second arm is adjacent to a part of the stem that extends through the at least one sidewall cutout, and wherein the second arm extends vertically beyond the at least one sidewall cutout;
wherein the rib component extends away from the platform sidewall such that the rib component provides a removably mountable boom attachment point; and
wherein the rib component supports the elevating platform by bearing a load from the elevating platform.

US Pat. No. 10,968,089

PLATFORM CONTROL BOX

Oshkosh Corporation, Osh...

1. A control box for a work platform, comprising:a housing defined by a first side panel and a second side panel opposing the first side panel, the first side panel and second side panel partially surrounding and extending from a lower enclosure to an upper enclosure spaced apart from the lower enclosure, at least one of the upper enclosure and the lower enclosure supporting a control panel having a plurality of inputs, at least one of the inputs being a platform positioning mechanism in communication with a lift system configured to move the work platform vertically between a stowed position and a deployed position;
a display supported by the housing and in communication with at least one of the plurality of inputs, the display being configured to receive and present output obtained by a sensor monitoring a parameter of the work platform; and
a roof extending between the first side panel and the second side panel and above the upper enclosure, wherein a protective cover is rotatably coupled to the roof and suspended downward from the roof, forward of the display;
wherein the sensor is one of a platform load measuring sensor, a platform tilt measuring sensor, and a platform elevation sensor;
wherein the control panel is a first control panel supported by the lower enclosure, at least one of the inputs on the first control panel being an ignition switch configured to communicate with a main battery positioned externally from the work platform; and
wherein the control box further comprises a second control panel supported by the upper enclosure, the upper enclosure supporting a second plurality of inputs and the display, at least one of the second plurality of inputs being configured to interact with the display.

US Pat. No. 10,968,088

REMOTE-CONTROLLED SHINGLE INSTALLATION JACK

1. A shingle installation device, comprising:a frame having a bottom member for anchoring a pulley, a first slider member, a second slider member, and a top member for supporting a walk board and for anchoring a first end of a spring, wherein the top member is in parallel with the bottom member and the first slider member is in parallel with the second slider member;
a mounting assembly for anchoring a winch motor, wherein the mounting assembly has an upper surface for anchoring a second end of the spring and a lower surface for anchoring an eye bolt;
a cable having an adjustable effective length running from the winch motor, through the pulley, and back to the eye bolt, wherein the adjustable effective length of the cable is controllable by the winch motor; and
the spring spanning from the top member of the frame to the upper surface of the mounting assembly.

US Pat. No. 10,968,087

PARCEL AND ARTICLE SORTING SYSTEM AND METHOD

Tompkins Robotics, Inc., ...

19. A self-propelled transport device configured for transporting an article of a plurality of articles, the transport device having a memory and a processor, the transport device configured to:receive or acquire information from a controller, wherein the controller interacts with an identifier associated with a selected article from the plurality of articles, each article having an identifier that includes a postal address destination,
wherein the received or acquired information is from an interaction with an information acquisition device that is fixedly positioned relative to the plurality of the articles;
receive the selected article from an article transferring device, wherein the controller directs the article transferring device to place the selected article about the transport device;
receive directions to traverse to a destination container of a plurality of destination containers to deposit, with the transport device, the selected article based on the interaction with the identifier; and
deposit the selected article by manipulation of the transport device from a first position in which the selected article is stowed about the transport device to a second position in which the selected article is deposited into the destination container,
wherein the transport device travels along a fixed transport path,
wherein the transport path is devoid of a track arrangement.

US Pat. No. 10,968,086

APPARATUS FOR LIFTING A VEHICLE TOP

1. An apparatus for lifting a vehicle top, comprising:a base frame, comprising:
two or more legs; and
one or more support structures couplable to the one or more legs at a selected angle;
a body frame couplable to the base frame, comprising:
one or more main supports; and
a lifting arm bracket couplable to the one or more main supports; and
a lifting arm couplable to the lifting arm bracket, comprising:
a lifting platform bracket coupled at an end of the lifting arm opposite the lifting arm bracket;
a lifting support couplable to the lifting platform bracket a selected distance from a first end of the lifting support, the lifting support rotatable about an axis through the lifting platform bracket, the lifting support comprising:
a main lifting support section; and
a secondary lifting support section, a first end of the secondary lifting support section being insertable in the main lifting support section, the lifting platform being coupled proximate to a second end of the secondary lifting support section, the main lifting support section and the secondary lifting support section being couplable together, the length of the lifting support being adjustable via the main lifting support section and the secondary lifting support section,
a lifting platform coupled to the lifting support at a second end of the lifting support, the lifting platform configured to engage an underside of a vehicle top; and
one or more stabilizing linkages couplable to the lifting arm bracket, the one or more stabilizing linkages being couplable to the lifting arm a selected distance from the end of the lifting arm, the one or more stabilizing linkages being couplable to the lifting support at the first end of the lifting support,
the lifting arm being rotatable about an axis through the lifting arm bracket,
the lifting platform maintaining an orientation substantially parallel to a ground surface as the lifting arm rotates about the axis through the lifting arm bracket.

US Pat. No. 10,968,085

LIFT ASSEMBLY SYSTEMS AND METHODS

Electronic Theatre Contro...

1. A lift assembly comprising:an article to be lifted between a lowered position and a raised position;
a drive element coupled to the article;
a power mechanism coupled to the drive element; and
a power transfer mechanism coupled between the power mechanism and the drive element, the power transfer mechanism including control electronics comprising:
a first upward limit switch adapted to deactivate the power mechanism when the article is lifted to a first upward height; and
a first downward limit switch adapted to deactivate the power mechanism when the article is lowered to a first downward height,
wherein the first upward limit switch and the first downward limit switch are disposed within a power head housing containing the power mechanism,
further comprising a first cam adjustment rod and a second cam adjustment rod partially extendable outside of the power head housing, wherein the first cam adjustment rod is coupled to a first rotatable cam and configured to adjust the first upward height, and the second adjustment rod is coupled to a second rotatable cam and configured to adjust the first downward height.

US Pat. No. 10,968,084

METHOD FOR MONITORING LIFTING EVENTS AT A CONSTRUCTION SITE

Versatile Natures Ltd., ...

1. A method for tracking lift events at a construction site comprising:accessing a first timeseries of load values output by a weight sensor, coupled to a crane hook, during a first time period;
accessing a first geospatial location of the crane hook during loading of an object onto the crane hook during the first time period;
deriving a lifting profile at the first geospatial location from the first timeseries of load values;
deriving a first weight of the object from the first timeseries of load values;
identifying a type of the object carried by the crane hook during the first time period based on the lifting profile;
accessing a second geospatial location of the crane hook during unloading of the object from the crane hook; and
generating a lift event record defining the type of the object, the first weight of the object, a pickup location of the object at the first geospatial location, and a drop-off location of the object at the second geospatial location.

US Pat. No. 10,968,083

CRANE COMPRISING AN IMAGE ACQUISITION SYSTEM

EPSILON KRAN GMBH, Salzb...

1. A crane comprising:a crane column;
a lifting device arranged on the crane column; and
an image acquisition system which is arranged to be raised and lowered by the lifting device for acquisition of a region of a crane environment, that cannot be directly viewed by an operator of the crane,
wherein the image acquisition system is arranged on a jib of the lifting device, and the jib extends in a straight line,
wherein the image acquisition system is moveable upwardly by an extension of the jib from a lift column, and is lowerable by retraction of the jib into the lift column into a transport position in which the jib is fully retracted and the image acquisition system is moved towards the lift column,
wherein the image acquisition system is arranged on a tip of the jib, the tip forming a highest point of the jib,
and wherein the lift column and the jib include an angle different from zero with the crane column in a vertical plane which has both the lift column and also the crane column.

US Pat. No. 10,968,082

CRANE, CONSTRUCTION MACHINE OR INDUSTRIAL TRUCK SIMULATOR

1. A simulator for a machine comprising:a movement simulation module for determining movements and/or deformations of machine components depending on entered control commands;
a control station comprising:
an input means for entering control commands;
a graphical simulation module configured to generate a virtual representation of a machine environment and/or machine components visible from the control station; and
a display device for displaying the virtual representation; and
a drive apparatus;
wherein the control station is moveably mounted to the drive apparatus for moving the control station depending on the movements and/or deformations determined by the movement simulation module;
wherein the movement simulation module comprises a data emulation apparatus for emulating movement data of the machine to be simulated;
wherein the data emulation apparatus comprises:
an actuator component for performing an actuator movement depending on an entered control command;
a first drive unit configured to perform actuator movements depending on control commands entered at the control station; and
a detection device configured to:
detect movements of the first drive unit; and
provide a movement and/or position signal;
wherein the movement simulation module further comprises a second drive unit coupled with the first drive unit, the second drive unit configured to exert a counter moment and/or a counter load in order to simulate actually occurring loads, resistances or inertia;
wherein the movement simulation module is configured to determine movements and/or deformations of machine components depending on at least a portion of the entered control commands; and
wherein the graphical simulation module is configured to generate the virtual representation:
based upon the determined movements and/or deformations from the movement simulation module; and
under consideration of a performed actuator movement.

US Pat. No. 10,968,081

SPREADER FOR LIFTING INTERMODAL CONTAINER

ELME SPREADER AB

1. A spreader for lifting an intermodal transport container, the spreader comprising:a main frame comprising, in an inner space of the main frame, a first travelling beam guide and, adjacent to said first travelling beam guide, a second travelling beam guide;
a first travelling beam having a proximal end guided in said first travelling beam guide to allow movement along a first guide axis, and a distal end connected to a first twist-lock arrangement; and
a second travelling beam having a proximal end guided in said second travelling beam guide to allow movement along a second guide axis, wherein said first and second guide axes are parallel, and a distal end is connected to a second twist-lock arrangement,
wherein the distal ends of said travelling beams are configured to variably extend from the respective travelling beam guides in opposite directions to allow changing an axial distance between said first and second twist-lock arrangements to accommodate for containers of different axial lengths,
wherein the main frame comprises a main beam formed of:
an upper C-beam of a relatively thicker material thickness, said upper C-beam being oriented so as to define a downwards-facing channel; and
a lower C-beam of a relatively thinner material thickness, said lower C-beam being oriented so as to define an upwards-facing channel, said upper and lower C-beams facing each other to define the inner space of the main frame comprising said upper and lower channels.

US Pat. No. 10,968,080

DRIVE BELT FOR PEOPLE CONVEYORS

OTIS ELEVATOR COMPANY, F...

1. Drive belt for a people conveyor comprising:a load bearing portion extending in a longitudinal direction and having a length extending in the longitudinal direction and a width extending in a width direction; and
a plurality of rollers accommodated within the width of the load bearing portion;
wherein at least a part of the load bearing portion is provided with a drive belt engagement structure, wherein the drive belt engagement structure in particular includes teeth, grooves, and/or openings;
wherein the load bearing portion comprises:
a first cord extending in the longitudinal direction; and
a second cord extending parallel to the first cord in the longitudinal direction; and
wherein roller axles supporting the rollers are mounted to a rear side of the first and second cords, the rear side of the first and second cords being opposite to a front side of the first and second cords, the drive belt engagement structure formed on the front side.

US Pat. No. 10,968,079

TRANSPORTATION DEVICE COMPRISING A SAFETY DEVICE FOR LIMITING DECELERATION

TK Elevator Innovation an...

1. A transportation device comprising:a person conveying unit; and
an electromagnetic linear drive configured to drive the person conveying unit by an electromagnetic drive force along a travel path, the electromagnetic linear drive including,
a stator segment, and
a runner element movably mounted to the person conveying unit and defining an air gap between the runner element and the stator segment, such that a width of the air gap is adjustable by movement of a position of the runner element on the person conveying unit, the runner element configured to:
be driven with respect to the stator segment in a first drive direction, or in a second drive direction opposite the first drive direction, by an electromagnetic field generated by the stator segment in the air gap, and
change position on the person conveying unit, so as to change a resulting width of the air gap, in response to a change in the electromagnetic drive force from the stator acting on the runner element, thereby adjusting a magnetic resistance between the stator segment and the runner element in the air gap.

US Pat. No. 10,968,078

METHOD AND HOISTING DEVICE

Kone Corporation, Helsin...

1. A method of monitoring a condition of a rope of a hoisting device, the rope including one or more load bearing members oriented to extend parallel with a longitudinal direction of the rope throughout a length thereof, the method comprising:reading, via a receiver located adjacent to a rope wheel of the hoisting device, measurements of strains of one or more portions of a load bearing member of the rope as the one or more portions of the one or more load bearing members rests on a circumference of the rope wheel such that the measurements are associated with the strains observed when the one or more portions are arched by the rope wheel; and
comparing the measured strains of the one or more portions of the load bearing member of the rope with at least one reference.

US Pat. No. 10,968,077

ENHANCED GOVERNOR SYSTEM FOR ELEVATOR

OTIS ELEVATOR COMPANY, F...

1. An overspeed assembly for use with a governor assembly for limiting of an elevator system, the overspeed assembly comprising:a rod movable relative to the governor assembly in response to a speed of an elevator car;
a pin coupled to the rod, the pin being movable between a first position and a second position based on a direction of travel of the elevator car, wherein the pin is configured to engage a first component to indicate a first overspeed condition when the elevator car is travelling in a first direction and the pin is configured to engage a second component to indicate a second overspeed condition when the elevator car is travelling in a second, opposite direction, wherein the pin is movable between the first position and the second position in response to a magnetic field of the overspeed assembly.

US Pat. No. 10,968,076

ELEVATOR MAINTENANCE FROM INSIDE ELEVATOR CAR

OTIS ELEVATOR COMPANY, F...

1. A method of operating an elevator system comprising:identifying one or more components in an elevator hoistway requiring periodic maintenance and/or inspection;
programming hoistway component locations of the one or more components into an elevator car control system;
driving the elevator car to a programmed hoistway component location of a selected component of the one or more components utilizing the hoistway component location programmed into the elevator car control system; and
accessing the selected component from inside the elevator car to perform maintenance and/or inspection of the selected component;
wherein programming the hoistway component locations of the one or more components includes:
driving the elevator car to the hoistway component location; and
recording a sensed hoistway component location into the elevator car control system, the sensed hoistway component location indicative of the hoistway component location.

US Pat. No. 10,968,075

ELEVATOR CAR LOCATION ZONES IN HOISTWAY

OTIS ELEVATOR COMPANY, F...

1. An elevator system comprising:a hoistway, the hoistway having a plurality of landing floors each landing floor having a landing floor door;
an elevator car disposed in and drivable along the hoistway; and
a controller to restrict operation of the landing floor doors based on a position of the elevator car along the hoistway;
wherein the hoistway includes a first hoistway zone and a second hoistway zone, such that when the elevator car is positioned in the first hoistway zone the controller allows for opening of a corresponding landing floor door; and
such that when the elevator car is positioned in the second hoistway zone the controller allows for opening of a corresponding landing floor door, without allowing entry of a person into the hoistway via the landing floor door.

US Pat. No. 10,968,074

ELEVATOR CAR WALL IMAGING SYSTEM AND METHOD

OTIS ELEVATOR COMPANY, F...

1. An elevator car wall imaging system comprising:an interior region of an elevator car, the interior region defined by a floor, a ceiling and a plurality of interior side walls; and
an image generator operatively connected to a network, the image generator configured to generate an image on at least a portion of at least one of the plurality of interior side walls, the image representing a weather condition currently present in an exterior environment surrounding a structure within which the elevator car is disposed;
wherein the image generator comprises a projection system;
wherein at least one of the plurality of interior side walls comprises a transparent material layer, a reflective film layer and a backlight layer.

US Pat. No. 10,968,073

TOUCHLESS ELEVATOR KEYBOARD SYSTEM

UNITED ARAB EMIRATES UNIV...

1. A touchless keyboard system for operating an elevator through an existing touch-sensitive keyboard of the elevator, the touchless keyboard system comprising:a touchless detection device comprising at least one sensor for detecting non-touch indications from users for opted floors;
an actuation device comprising at least one actuator for physically engaging buttons of the existing touch-sensitive keyboard of the elevator corresponding to the opted floors, and
a controller in communication with the detection device and with the actuation device for receiving and processing output signals from the at least one sensor and controlling movement of the at least one actuator based on the processed output signals.

US Pat. No. 10,968,072

AUTOMATIC DIVING TENDING SYSTEM

The United States of Amer...

1. An automatic diving tending system (ADTS), comprising:a buoyant sealed torsional apparatus comprising a plate having a perimeter seal to which is affixed a cover with a perimeter flange forming a dry buoyant cavity, a bridge mounted on the plate that is supporting a drive shaft, which is about perpendicular to a bottom of the plate, a locking mechanism, and a constant torque spring motor having a take-up reel with a gear wheel and an unwind reel having a recoil spring, and an overdrive transmission linkage from the gear wheel to the drive shaft; and
a tether spool apparatus comprising a frame having at least one guide,
wherein said frame is mounted on an exterior bottom side of the plate, wherein said frame supports and protects a spool with a spool shaft to support a pair of opposing spool walls and terminates with a top-side coaxial structure connected to the drive shaft, wherein a line wound on the spool that is pulled off the spool has about a constant tension and generates a fractional length of the recoil spring to be wound onto the take-up reel of the spring motor for a length of line pulled off the spool, and wherein a slackening of the line is removed by automatic rewinding of the line onto the spool until the slackening is removed, where energy for the automatic rewinding is provided by the spring motor as a partial fractional length of the recoil spring moves back to the unwind reel.

US Pat. No. 10,968,071

METHOD OF CONTROLLING A COMPENSATOR OF THE DIFFERENCE BETWEEN THE DRAWING-OFF AND WINDING SPEEDS OF YARN WHEN WINDING YARN ON A BOBBIN AT A WORKSTATION OF A SPINNING MACHINE AND A DEVICE FOR PERFORMING THE METHOD

Maschienfabrik Rieter AG,...

1. A method of controlling a compensator of a difference between drawing-off and winding speeds of yarn when winding yarn on a bobbin at a workstation of a spinning machine, the compensator comprising a compensating arm movable between different positions at different stages of operation at the workstation, as well as during service operations at the workstation following filling and emptying of the yarn from an intermediate vacuum storage device at the workstation, the method comprising:before emptying the yarn from the intermediate vacuum storage device, deflecting the compensating arm over a working range thereof across a path of the yarn and into an out-of-the-working-range position of the compensating arm, wherein the yarn is captured by the compensating arm and is also deflected with the compensating arm to the out-of-the-working-range position thereby forming a non-working reserve of yarn;
maintaining the compensating arm at the out-of-the-working-range position with a retaining force while emptying the yarn from the intermediate vacuum storage device; and
wherein upon emptying the intermediate vacuum storage device, the yarn exerts tensile force on the compensating arm that overcomes the retaining force such that the compensating arm returns from the out-of-the-working-range position to the working range and resumes operation.

US Pat. No. 10,968,070

APPARATUS AND METHOD FOR TENSIONING AND THREADING OPTICAL FIBER

Corning Incorporated, Co...

1. An apparatus for tensioning and threading an optical fiber, comprising:a plurality of rollers structured to maintain an optical fiber under tension; and
a compartment that houses the plurality of rollers, the compartment being held under a negative pressure.

US Pat. No. 10,968,069

TUBE HOLDER FOR LINE DISPENSING

Aladdin Manufacturing Cor...

1. A tube holder for supporting a tube while flexible line is drawn off of a spool of flexible line coiled onto the tube, wherein the tube holder comprises:a body portion configured to support the tube thereon, wherein the body portion defines a base end and an opposite distal end and the distal end comprises a contact fastener member; and
an end protector detachably secured to the distal end of the body portion, and wherein the end protector comprises a mating fastener member configured to be secured relative to the contact fastener member; and
wherein the contact fastener member and the mating fastener member collectively comprise a magnet and a magnetic member.

US Pat. No. 10,968,068

RETAIL EDGE MARKER ACCUMULATION AND COLLATION SYSTEM

Xerox Corporation, Norwa...

10. A method for accumulating and collating media strips exiting an upstream source, comprising:providing a plurality of angled baffles with each of said plurality of angled baffles configured to include bins that receive said media strips with each of said media strips extending over at least two of said plurality of angled baffles;
feeding said media strips onto a longitudinal surface of said bins from said upstream source;
wherein said series of baffles includes an upstream angled baffle with each of the remainder of said plurality of baffles configured to cascade from said upstream baffle to eliminate media strip stub points while simultaneously providing a downward slope to enhance media strip sliding down said plurality of baffles; and
providing a pusher configured for movement orthogonally to said bins after said media strips have settled into said bins to pull said media strips in collated form from said bins and into a compiled collated stack in store planogram order.

US Pat. No. 10,968,067

HEAVY DUTY TAPE DISPENSER

SHURTAPE TECHNOLOGIES, LL...

1. An adhesive tape dispenser comprising:a frame including a forward tape guide portion having a generally planar top tape guide surface, a front edge, a first side edge and a second side edge;
first and second flexible sidewall arm portions disposed generally perpendicular to the generally planar top guide surface and extending rearwardly in a generally side-by-side spaced apart relation from the first side edge and second side edge, respectively, the first and second flexible sidewall arm portions each having an interior surface and an exterior surface;
inwardly facing opposed first and second hub portions projecting from the interior surface of the first and second flexible sidewall arm portions, respectively, the first and second hub portions having a generally arcuate shape and including a roll surface, a bottom surface, and an abutment surface, wherein the abutment surface connects the roll surface to the bottom surface, and wherein the roll surface is configured to support core upon which the adhesive tape is disposed;
a first tab disposed on the bottom surface of the first hub portion extending inwardly toward the second hub portion, the first tab including a passage configured to receive a projection disposed on the bottom of the surface of the second hub portion;
a second tab disposed on the bottom surface of the second hub spaced apart from the projection, the second tab extending inwardly toward the first hub portion and configured to slidably contact the bottom surface of the first hub; and
wherein when the first tab is engaged with the projection, the abutment surfaces of the first and second hubs are in contact.

US Pat. No. 10,968,066

MEDIUM DISCHARGE DEVICE AND IMAGE READING APPARATUS

Seiko Epson Corporation, ...

1. An image reading apparatus comprising:a document support section for placing a document in an inclined position;
a feeding roller for feeding the document obliquely downward;
a reading section for reading the document fed from the feeding roller;
a discharge roller that discharges the read document and a discharge tray that receives the document discharged from the discharge roller; and
a guide member having a tip end, a base end supported by the discharge tray, and an inclined portion provided between the base end and the tip end, the guide member being configured to be displaceable in a vertical direction, and guide a leading end of the discharged document,
wherein a distance between the base end and the discharge roller is longer than a distance between the tip end and the discharge roller in both a vertical and a horizontal direction.

US Pat. No. 10,968,065

EMERGENCY STOP CUTTING MECHANISM FOR A WEB REWINDING DEVICE

Tecnau, Inc., Billerica,...

1. A web winder comprising:an input that receives web on a feed path from an upstream handling device;
a take-up roll that is driven to form the web into a roll as the web is delivered at the input; and
an emergency stop cutting mechanism located between the input and the take-up roll that, in response to a stop signal, releases a blade oriented at a non-perpendicular angle to a feed direction of the feed path along a cross-web direction, wherein the blade is engaged with the web in motion, and the blade is biased across the web to separate the web by drawing of the take up roll.

US Pat. No. 10,968,064

WINDING DEVICE FOR WINDING UP A RIBBON OR WEB

HERMA GMBH, Filderstadt ...

1. Winding device (10) for winding a carrier web (92) onto a reel (90),said winding device (10) having a drive shaft (20), a gear (30), a clutch shaft (63), an energy storage means (50), a clutch (60) and an output shaft (80),
said gear (30) being configured, as a positive-engagement gear, to transmit a rotary movement of the drive shaft (20) to a first clutch shaft element (61) assigned to the clutch shaft (63),
said clutch shaft (63) being connected via the clutch (60) with the output shaft (80) in order, selectively, to enable a transmission of torque between the clutch shaft (63) and the output shaft (80) or to prevent a transmission of torque between the clutch shaft (63) and the output shaft (80),
said gear (30) having, at times when the energy storage means (50) is not effective, a first predetermined transmission ratio (i_0) between the drive shaft (20) and the clutch shaft (63),
and said energy storage means (50) being configured
to enable a storage of potential energy with simultaneous increase of the transmission ratio relative to the first predetermined transmission ratio,
and to enable a release of the stored potential energy with simultaneous lowering of the transmission ratio relative to the first predetermined transmission ratio.

US Pat. No. 10,968,063

MEDIUM FEEDING DEVICE AND IMAGE READING APPARATUS

Seiko Epson Corporation, ...

1. A medium feeding device comprising:a placement unit on which a medium is placed;
a pair of edge guides that is provided at the placement unit such that the edge guides are movable in a medium width direction to guide edges of the medium in the medium width direction that is a direction intersecting a medium feeding direction;
feeding rollers that feed the medium placed on the placement unit;
a medium feeding path through which the medium fed from the placement unit passes;
a path state detection section that detects a detection value in accordance with a state of the medium feeding path;
a guide position detection section that detects positions of the edge guides, wherein the guide position detection section is attached to at least one of the pair of edge guides; and
a control section that determines whether or not the detection value detected by the path state detection section has exceeded a threshold value,
wherein the control section changes the threshold value in accordance with a detection signal of the guide position detection section,
wherein the control section is able to detect relative positions of the pair of edge guides and the feeding rollers in the medium width direction on the basis of the detection signal of the guide position detection section, and
wherein the control section sets the threshold value that is applied in a case in which the feeding rollers are not located at the center of the pair of edge guides in the medium width direction to be smaller than the threshold value applied in a case in which the feeding rollers are located at the center of the pair of edge guides on the basis of the detection signal of the guide position detection section.

US Pat. No. 10,968,062

TRANSFER TRANSPORTING DEVICE AND IMAGE FORMING APPARATUS

FUJI XEROX CO., LTD., To...

1. A transfer transporting device, comprising:a plurality of rollers including:
a driving roller; and
a driven roller,
wherein the driving roller is disposed closer to an image carrier configured to carry a toner image, and
wherein the driven roller is disposed apart from the driving roller downstream in a sheet transport direction;
an endless belt wound around the plurality of rollers;
a pair of support members each having an outer wall surface facing a corresponding one of side end surfaces of the belt,
wherein the pair of support members is disposed on both sides of the belt to rotatably support a rotation shaft protruding from side end surfaces of the driving roller; and
a pair of unloading members interposed between the outer wall surfaces of the pair of support members and the side end surfaces of the driving roller,
wherein the pair of unloading members are configured to reduce, while being in contact with a corresponding one of the side end surfaces of the belt, a driving load on the driving roller more than in a case where the side end surfaces of the belt directly contact the outer wall surfaces,
wherein the image carrier and the belt are configured to hold therebetween a sheet transported thereto to transfer the toner image on the image carrier to the sheet,
wherein the image carrier and the belt are configured to transport the sheet downstream in the sheet transport direction,
wherein each of the unloading members is configured to, when projected in a direction of the rotation shaft, extend to cover a portion of the corresponding side end surface of the belt upstream of the rotation shaft in the sheet transport direction,
wherein each of the unloading members is configured to, when projected in the direction of the rotation shaft, cover the portion of the corresponding side end surface of the belt upstream of the rotation shaft in the sheet transport direction, and
wherein each of the unloading members extends downstream in the sheet transport direction to at least a portion of a contact area between the belt and the image carrier.

US Pat. No. 10,968,061

IMAGE FORMING APPARATUS

RICOH COMPANY, LTD., Tok...

1. An image forming apparatus comprising:a sheet container configured to accommodate a sheet bundle including a sheet therein; and
a sheet separating feeder including:
a sheet feeding body having a surface to contact the sheet accommodated in the sheet container and configured to feed the sheet from the sheet container;
a sheet separating body configured to contact the sheet feeding body and form a sheet separation nip region with the sheet feeding body, and to sandwich the sheet in the sheet separation nip region;
a bend applier disposed upstream from the sheet separation nip region in a sheet conveying direction, the bend applier configured to include a leading end forming member, a first body forming member disposed upstream from the leading end forming member in the sheet conveying direction, and a second body forming member disposed downstream from the leading end forming member in the sheet conveying direction; and
a projection configured to contact the sheet, the projection being disposed outside a side end of the sheet separating body in a direction perpendicular to the sheet conveying direction and being disposed outside at a side end of the leading end forming member of the bend applier in the direction perpendicular to the sheet conveying direction,
wherein an uppermost part of the first body forming member is lower than an uppermost part of the leading end forming member,
wherein a leading end of the leading end forming member includes elastic material to contact the sheet,
wherein the leading end forming member contacts the leading end of the sheet,
wherein the leading end forming member further includes a leading extended portion extending from an upright portion of the leading end forming member,
wherein a surface of the upright portion of the leading end forming member on a side of the sheet container is attached to a surface of the first body forming member on a side of the sheet separation nip region,
wherein the leading extended portion of the leading end forming member is supported by the upright portion of the leading end forming member in a cantilever manner without being attached to the first body forming member in a state in which the upright portion of the leading end forming member is located below the uppermost part of the first body forming member in a direction of gravitation, and
wherein the surface of the upright portion of the leading end forming member on the side of the sheet separation nip region is attached to a surface of the second body forming member on a side of the sheet container.

US Pat. No. 10,968,060

SHEET CASSETTE

FUJITSU COMPONENT LIMITED...

1. A sheet cassette that accommodates a recording sheet and is connectable to a printer, the sheet cassette comprises:a first roller that contacts a feed roller of the printer;
a second roller that contacts a recording sheet;
a first gear and a second gear that are attached to a shaft of the first roller;
a third gear and a fourth gear that are attached to a single shaft; and
a fifth gear that is attached to a shaft of the second roller,
wherein the first gear independently rotates relative to the first roller and the second gear, the first gear engages with the third gear, the fourth gear rotates together with the third gear, the fourth gear engage with the fifth gear, and the second roller is rotated by rotation of the fifth gear, and
when the sheet cassette is connected with the printer, the first gear engages with a feed gear of the printer.

US Pat. No. 10,968,059

SHEET STACKING DEVICE AND IMAGING FORMING APPARATUS PROVIDED WITH SAME

KYOCERA Document Solution...

1. A sheet stacking device, comprising:a sheet accommodating unit having a substantially rectangular parallelpipedic box shape with an open top and a bottom part opposite the open top, the sheet accommodating unit accommodating a sheet bundle of stacked sheets therein through the open top; and
a loading plate arranged horizontally in the sheet accommodating unit and having an upper surface, the loading plate being configured such that the sheets are to be placed on the upper surface of the loading plate, the loading plate having first and second side edges extending in a first direction and first and second end edges perpendicular to the first direction, the loading plate being vertically movable in a predetermined moving range from a lowermost position where the loading plate is in proximity to the bottom part of the sheet accommodating unit to an uppermost position where the loading plate is spaced farther above the bottom part of the sheet accommodating unit; wherein
the sheet accommodating unit including:
first and second side walls standing to face the respective first and second side edges of the loading plate;
first and second end walls standing to face the respective first and second end edges of the loading plate;
a first regulating portion standing at a first regulating position inward of the first end wall by a predetermined distance in the first direction, the first regulating position being a position to regulate a movement of the sheet bundle in the first direction; and
a first observation port formed on at least one of the side walls and configured to allow an inner part of the sheet accommodating unit to be visible from outside of the sheet accommodating unit, the first observation port being arranged at a position in the first direction spaced inward from end portions of the respective side wall to expose the first regulating position to the outside of the sheet accommodating unit, a lowermost edge of the first observation port being disposed lower than the loading plate and between the loading plate and the bottom part of the sheet accommodating unit when the loading plate is in the lowermost position in the predetermined moving range.

US Pat. No. 10,968,058

U RECLAIMER UTILITY DEVICE APPARATUS

1. A reclaimer device to reclaim cement from a cement storage facility by scraping layers of said cement from a cement pile to a dispatch area, said reclaimer device comprising:a plurality of scrapers mounted on a reclaiming chain, said chain configured to loop from a front end to a rear end;
mechanical means to circulate said reclaiming chain;
a gantry comprising a front end and a rear end to support said reclaiming chain;
a cable configured to be mounted on top of said gantry;
said cable configured to be connected to the front end of said reclaiming chain;
mechanical means to lift or lower said cable;
at least one hydraulic cylinder configured to be connected to the top of said gantry;
said hydraulic cylinder configured to be connected to said rear end of said reclaiming chain;
mechanical means to extend or contract said hydraulic cylinder;
a plurality of wheels supporting said gantry;
mechanical means to turn said wheels;
automated means to control said mechanical means to turn said wheels;
automated means to control lifting or lowering of said cable;
automated means to control extending or contracting of said hydraulic cylinder;
electronic means to determine a position of said gantry on said cement pile; and
electronic means to determine a position of said reclaiming chain on said cement pile.

US Pat. No. 10,968,057

COLLECTING CHUTE FOR COMBINATION WEIGHING DEVICE WITH VARIABLE SLOPE TO REDUCE THE VARIATION IN ARRIVAL TIME AT THE DISCHARGE END OF THE CHUTE OF ARTICLES DISCHARGED FROM DIFFERENT HOPPERS ARRANGED AT VARRYING DISTANCES APART

Ishida Co., Ltd., Kyoto ...

1. A collecting chute comprising:a plurality of chute units having a supply port to which articles are supplied, each of the chute units including a discharge port from which the articles are discharged, and an inner circumferential surface communicating with the supply port and the discharge port so that an area of the discharge port in planar view seen from a direction in which the articles are supplied is smaller than the area of the supply port, wherein
the chute units are arrayed along a circular virtual line in the planar view and are also arrayed securing a space among the chute units at a central portion of the circular virtual line,
each of the chute units has an outer slope that is the inner circumferential surface along the circular virtual line, and an inner slope that is the inner circumferential surface located on a back side of an outer circumferential surface facing other chute units,
a tilt angle of the inner slope is greater than a tilt angle of the outer slope, and
a first discharge port and a second discharge port form a single, contiguous opening.

US Pat. No. 10,968,056

HANDLING DEVICE FOR PRODUCT STACKS

MBO POSTPRESS SOLUTIONS G...

1. A handling device for transferring a stack of folded, stapled or bound products, from a receiving region to a depositing region,wherein the handling device comprises a gripping unit which is movable in three dimensions and which is specified for receiving the stack of products disposed in the receiving region, for moving the stack, and for depositing the stack in the depositing region;
wherein the gripping unit comprises at least one upper holding element for holding down an upper side of the received stack, and at least one lower holding element for supporting a lower side, opposite the upper side, of the received stack;
wherein the gripping unit further comprises a first lateral delimitation element and a second lateral delimitation element, which are in each case assignable to two mutually opposite lateral faces of the stack at inner surfaces of the first lateral delimitation element and the second lateral delimitation element;
wherein the first lateral delimitation element comprises a guide extending along the first lateral delimitation element, the at least one upper holding element being linearly displaceable along said guide, wherein the at least one upper holding element is preloaded to a predetermined position or is freely movable within said guide, and wherein the at least one upper holding element protrudes from said guide towards the second lateral delimitation element.

US Pat. No. 10,968,055

MONORAIL TRAY CONVEYOR WITH PASSIVE GUIDE RAILS

Laitram, L.L.C., Harahan...

1. A tray conveyor comprising:a tray extending in length from a first end to a second end and in width from a first side to a second side and having a bottom with flat surface areas at the first and second sides and having a permanent-magnet array extending along its length;
a conveyor frame extending in length in a conveying direction;
a linear-motor stator mounted in the conveyor frame and producing an electromagnetic wave traveling along the length of the conveyor frame;
a pair of guide rails flanking the linear-motor stator across gaps separating the linear-motor stator from the pair of guide rails and supporting the tray from below in contact with the flat surface areas at the first and second sides of the tray on opposite sides of the permanent-magnet array;
wherein the electromagnetic wave interacts with the permanent-magnet array to propel the tray along the guide rails in the conveying direction.

US Pat. No. 10,968,054

AIR ASSISTED PARTICULATE DELIVERY SYSTEM

KIMBERLY-CLARK WORLDWIDE,...

1. A particulate material conveying apparatus comprising:a slide duct extending between a proximal end and a distal end and having a slide duct axis extending in both a vertical direction and a horizontal direction, the slide duct comprising:
an interior region bounded at least in part by a slide duct wall, the interior region having a top third interior region extending along the slide duct axis, a middle third interior region extending along the slide duct axis, and a bottom third interior region extending along the slide duct axis, each interior region extending between the proximal end and the distal end of the slide duct, wherein the top third interior region is disposed above the middle third interior region in the vertical direction and wherein the middle third interior region is disposed above the bottom third interior region in the vertical direction,
an opening defined by the slide duct wall, and
a particulate material outlet through which particulate material enters the interior region of the slide duct, wherein the particulate material outlet is disposed closer to the distal end of the slide duct than the opening; and
an air movement mechanism configured to move air through the opening and into the interior region of the slide duct in a direction of the slide duct axis such that of the air exiting the slide duct distal end a greater amount of air exits through the bottom third interior region than either of the top third interior region or the middle third interior region.