US Pat. No. 10,655,038

METHOD OF MAKING MAGNETIZABLE ABRASIVE PARTICLES

3M Innovative Properties ...

1. A method of making magnetizable abrasive particles, the method comprising sequentially:providing a slurry layer disposed on a releasable substrate, wherein the slurry layer has an exposed surface, and wherein the slurry layer comprises magnetic particles, a binder precursor, and a liquid vehicle;
electrostatically contacting abrasive particles with the slurry layer, wherein the abrasive particles are aligned substantially oriented perpendicular to the surface of the releasable substrate, and wherein the abrasive particles are partially embedded within the slurry layer;
at least partially removing the liquid vehicle from the slurry layer and converting the binder precursor into a binder to provide a magnetizable layer comprising the magnetic particles and the binder, wherein the abrasive particles are partially embedded in the magnetizable layer;
separating the magnetizable abrasive particles from the releasable substrate, wherein the magnetizable abrasive particles each respectively comprise a portion of the magnetizable layer is disposed on a portion of each of the abrasive particles.

US Pat. No. 10,655,036

ADHESIVE SHEET AND ADHESIVE SHEET PRODUCTION METHOD

LINTEC CORPORATION, Itab...

1. A pressure sensitive adhesive sheet, comprising:a substrate or a release material; and
a resin layer provided on the substrate or the release material and comprising a resin part (X) comprising a resin as a main component and a particle part (Y) consisting of fine particles having a mean particle size of 0.01 to 100 ?m,
wherein the fine particles comprise at least one selected from the group consisting of silica particles comprising 85 to 100% by mass of silica, metal oxide particles, and smectite particles,
at least a surface (?) of the resin layer on the side opposite to the side on which the substrate or the release material is provided has pressure sensitive adhesiveness,
a concave portion and a plurality of flat faces having an irregular shape exist in a region (Dc) surrounded by a circle having a diameter of 8 mm that is arbitrarily selected on the surface (?) of the resin layer,
the plurality of flat faces comprises a flat face (f1) having an area within which a region surrounded by a circle having a diameter of at least 100 ?m is selectable, and
with respect to at least one flat face (S) in the plurality of flat faces excluding flat faces having a cumulative relative frequency of 30% or less determined by adding relative frequency from the respective flat faces with a smaller area, when the region (Dc) containing one or more of the flat faces (S) is placed on an orthogonal coordinate system such that a direction orthogonal to the horizontal Feret's diameter direction is the vertical Feret's diameter direction, an rMAX value of the one or more of the flat faces (S) calculated from the following Operations (i) to (iii) is 0.60 or less:
Operation (i): with respect to all of the one or more of the flat faces (S) contained in the region (Dc), a ratio of an area of the flat face (S) to an area of a circumscribed rectangle of flat face (S) which circumscribes the flat face (S) by two pairs of straight lines parallel to the horizontal Feret's axis and the vertical Feret's axis [{area of flat face (S)}/{area of circumscribed rectangle of flat face (S)}] is calculated for every flat face (S), and r(0°) that is an average value of the obtained ratios is calculated;
Operation (ii): with respect to each of all of the one or more of the flat faces (S) in each region obtained by rotating the region (Dc) at ?, where ?=15°, 30°, 45°, 60°, 75°, or 90°, in the counterclockwise direction centering on, as a center of the rotation, the center of the circle of the region (Dc) used in the Operation (i) in the orthogonal coordinate system, a ratio of an area of the flat face (S) to an area of a circumscribed rectangle of flat face (S), which circumscribes the flat face (S) by two pairs of straight lines parallel to the horizontal Feret's axis and the vertical Feret's axis [{area of flat face (S)}/{area of circumscribed rectangle of flat face (S)}] is calculated for every flat face (S), and r(?) that is an average value of the obtained ratios is calculated with respect to every case at ?=15°, 30°, 45°, 60°, 75°, and 90°; and
Operation (iii): a maximum value of the seven values of r(?), where ?=0°, 15°, 30°, 45°, 60°, 75°, and 90°, as calculated in the Operations (i) and (ii) is defined as the rMAX value of the one or more of the flat faces (S).

US Pat. No. 10,655,035

OXIDIZING FLUID FOR THE CHEMICAL-MECHANICAL POLISHING OF CERAMIC MATERIALS

1. A fluid composition for chemical-mechanical polishing, comprising:a solvent;
0.5-5 wt % of a first oxidizing agent comprising an ion, salt, acid, or base of permanganate or Ce+4 and having an oxidation potential of 0.4 V or greater;
0.1-0.5 wt % of a second oxidizing agent comprising an ion, salt, acid, or base of persulfate and having a higher oxidation potential than the first oxidizing agent and 0.05-0.75 wt % of a multivalent cation component comprising Al+3, Fe+3, or Co+3.

US Pat. No. 10,655,032

INK JET RECORDING METHOD

FUJIFILM CORPORATION, To...

1. An ink jet recording method, comprising:jetting, on a substrate, an ink composition A that contains a microcapsule having a polymerizable compound within the microcapsule, a high boiling solvent, water, and a colorant, and an ink composition B that contains a microcapsule having a polymerizable compound within the microcapsule, a high boiling solvent, water, and carbon black; and
heating the ink composition A and the ink composition B, which have been jetted on the substrate,
wherein an absorbance ABSA of the ink composition A and an absorbance ABSB of the ink composition B satisfy Formula (1), and a concentration MA of the high boiling solvent contained in the ink composition A and a concentration MB of the high boiling solvent in the ink composition B satisfy Formula (2),
ABSA MA wherein, in Formula (1), ABSA and ABSB respectively represent an average value of the absorbance of the ink composition A and the ink composition B at wavelengths of from 800 nm to 1400 nm,
wherein, in Formula (2), MA and MB respectively represent the concentration of the high boiling solvent contained in the ink composition A and the concentration of the high boiling solvent contained in the ink composition B, with respect to a total mass of each ink composition, and
wherein ABSA, ABSB, MA, and MB satisfy Formula (3):
{1+0.01×(ABSB/ABSA)}*MA

US Pat. No. 10,655,031

INK JET INK COMPOSITION, INK ACCOMMODATION BODY AND INK JET RECORDING METHOD

Seiko Epson Corporation, ...

1. An ink jet recording method, comprising: discharging an ultraviolet curing ink jet ink composition from a head to a recording medium at 30° C. to 40° C. to record thereon, wherein the ultraviolet curing ink jet ink composition is a white ink comprising inorganic metal-based fine particles as a color material and has a viscosity of 8 to 20 mPa·s at 20° C., wherein a content of the inorganic metal-based fine particles is 8 to 25 mass % with respect to the total mass of the ultraviolet curing ink jet ink composition, wherein the inorganic metal-based fine particles comprise titanium oxide, and wherein the ink jet composition contains a light radical polymerization initiator, the ink jet ink composition polymerizing by light radical polymerization, the ultraviolet curing ink jet ink composition further comprises a monofunctional (meth)acrvlate other than a vinvlether group-containing (meth)acrvlate having a content of 30 mass % or more with respect to the total mass of the ultraviolet curing ink jet ink composition.

US Pat. No. 10,655,030

WATER-BASED INK

KAO CORPORATION, Tokyo (...

1. An ink set for ink-jet printing comprising two or more kinds of water-based inks which are each constituted of a water-based ink comprising a pigment (A), a water-insoluble polymer (B), an organic solvent (C), a surfactant (D) and water, wherein pigment (A) in each kind of water-based ink differs in color from pigment (A) in every other kind of water-based ink in said ink set, in which:the pigment (A) is present in the water-based ink in the form of pigment-containing water-insoluble polymer particles;
the organic solvent (C) comprises at least a glycol ether (c-1) which has a viscosity of not less than 2.0 mPa·s and not more than 7.0 mPa·s as measured at 20° C. and a vapor pressure of not less than 0.01 hPa and not more than 7.0 hPa as measured at 20° C., and a content of a glycol ether having a viscosity of not less than 6.0 mPa·s as measured at 20° C. as a component of the glycol ether (c-1) in the water-based ink is not less than 0% by mass and not more than 5% by mass, a content of the organic solvent (C) in the water-based ink is not less than 25% by mass and not more than 45% by mass, a content of water in said water-based inks is 40% to 85% by mass, and a content of a high-boiling organic solvent having a boiling point of not lower than 250° C. in the water-based ink is not more than 5% by mass; and
the surfactant (D) comprises a silicone-based surfactant (d-1), and a content of the silicone-based surfactant (d-1) in the water-based ink is not less than 0.005% by mass and not more than 0.3% by mass, wherein a kinematic viscosity of the silicone-based surfactant (d-1) as measured at 25° C. is not less than 40 mm2/s and not more than 1000 mm2/s, and wherein a HLB value of the silicone-based surfactant (d-1) is not less than 2.0,
wherein the glycol ether (c-1) is at least one compound selected from the group consisting of ethylene glycol isopropyl ether, ethylene glycol propyl ether, diethylene glycol isopropyl ether and diethylene glycol isobutyl ether,
wherein the set consists of three of the water based inks, one of which contains yellow pigment, one of which contains magenta pigment, and one of which contains cyan pigment,
wherein water has a largest content among components of a medium contained in said water-based inks;
wherein the organic solvent (C) further comprises an organic solvent (c-2) other than the glycol ether (c-1), and the organic solvent (c-2) further comprises an alkanediol having not less than 2 and not more than 6 carbon atoms, and
wherein a content of the glycol ether (c-1) in the organic solvent (C) is not less than 30% by mass and not more than 90% by mass;
wherein the silicone-based surfactant (d-1) is a polyether-modified silicone-based surfactant represented by the following general formula (1):

wherein R1 is an alkyl group having 1 to 3 carbon atoms or a hydroxy group; R2 is an alkanediyl group having 2 to 5 carbon atoms: R3 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a hydroxy group; PO is a propyleneoxy group; EO is an ethyleneoxy group; a, b, m and n represent average molar numbers of addition of the respective constitutional units, and a is a number of 0 to 10, b is a number of 1 to 50, m is a number of 1 to 500 and n is a number of 1 to 50; and a plurality of the R1 groups may be the same or different from each other; and in the general formula (1), a, b, m and n have the following ranges:
[a+b] is not less than 5 and not more than 35,
[m/n] is not less than 3 and not more than 20, and
[a+b]/[m+n] is not less than 0.5 and not more than 6.

US Pat. No. 10,655,029

INKJET INK AND COLORING COMPOSITION

Ricoh Company, Ltd., Tok...

1. An inkjet ink comprising:a stilbene-based compound represented by General Formula (1),

where in the General Formula (1), R1 and R2 each independently represent an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, a phenyl group, a naphthyl group, or a group represented by —(CH2)n—COO—R3, —(CH2)n—R4, —(CH2)n—CONH—R5, —CR6R7—COO—R8, or —(CH2)n—OCOCH3;
R3 represents a hydrogen atom, an alkali metal atom, or an alkyl group having 1 to 2 carbon atoms;
R4 represents a hydroxy group, an alkoxy group having 1 to 2 carbon atoms, an alkenyloxy group having 2 to 5 carbon atoms, a SO3Na group, an OSO3Na group, a phenylalkyl group where an alkyl portion of the phenylalkyl group has from 1 to 3 carbon atoms, or a naphthylalkyl group where an alkyl portion of the naphthylalkyl group has from 1 to 3 carbon atoms;
R5 represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, or a hydroxyalkyl group having 1 to 12 carbon atoms;
R6 represents a hydrogen atom or a methyl group;
R7 represents an alkyl group having 1 to 4 carbon atoms;
R8 represents an alkyl group having 1 to 5 carbon atoms; and
n is an integer of from 1 to 12.

US Pat. No. 10,655,028

INK JET RECORDING METHOD AND INK SET

Seiko Epson Corporation, ...

1. An ink jet recording method comprising:attaching by ink jet coating a reactin liquid to a low absorbent recording medium or non-absorbent recording medium to form a first recorded region, the reaction liquid containing a coagulant having solubility of 120 g or less in 100 g of water as a coagulant which coagulates components of an ink composition, and
attaching the ink composition containing water and a resin having a percentage of water absorption of 0.3% or less to at least one part of the first recorded region to form a second recorded region,
wherein the attaching of the ink composition includes:
attaching a first ink composition to at least one part of the first recorded region to form the second recorded region, the first ink composition being a color ink composition that contains water, a coloring material, and the resin having a percentage of water absorption of 0.3% or less, a content of the resin having a percentage of water absorption of 0.3% or less being less than 5% by mass, and
attaching a second ink composition such that the second ink composition overlaps the first ink composition,
wherein the second ink composition is a clear ink composition that contains water and the resin having a percentage of water absorption of 0.3% or less, a content of the resin having a percentage of water absorption of 0.3% or less in the second ink composition is 10% by mass or less, and
the resins having a percentage of water absorption of 0.3% or less contained in each of the first and second ink compositions are a polyolefin-based resin.

US Pat. No. 10,655,025

CURABLE UNSATURATED CRYSTALLINE POLYESTER POWDER AND METHODS OF MAKING THE SAME

XEROX CORPORATION, Norwa...

1. A process for making a composition comprising:providing an unsaturated polyester resin comprising:
an ethylenically unsaturated monomer having the formula I

wherein p and q are each independently 0 to 8, and z is 1 to 5,
a first diol monomer; and
a second diol monomer;
mixing and heating a mixture comprising the unsaturated polyester resin and an oil at a temperature above the melting point temperature (Tm) of the unsaturated polyester resin, and applying a pressure to the mixture to form a microparticle composite;
washing the microparticle composite with an organic solvent to reduce the amount of oil present in the microparticle composite;
adding a thermal initiator to the microparticle composite; and
removing the organic solvent to form the composition comprising microparticles with the thermal initiator on the surface of the microparticles.

US Pat. No. 10,655,024

FLEXIBLE, BIODEGRADABLE, AND BIOCOMPATIBLE SUPERCAPACITORS

Virginia Commonwealth Uni...

1. A supercapacitor, comprisinga flexible protein substrate,
at least two electrodes comprising a biocompatible conductive ink patterned on the flexible protein substrate, and
a biocompatible gel electrolyte connecting the at least two electrodes,
wherein each of the flexible protein substrate, the at least two electrodes, and the gel electrolyte are biodegradable.

US Pat. No. 10,655,021

METHOD OF FABRICATING A LOADED POWDER, AND A PRODUCT MADE OF ELECTRICALLY CONDUCTIVE COMPOSITE MATERIALS

AIRBUS HELICOPTERS, Mari...

1. A method of fabricating an electrically conductive powder of thermoplastic polymers, the electrically conductive powder of thermoplastic polymers being referred to as a loaded powder, wherein the method comprises the steps of:making an original powder containing cores of thermoplastic polymers, each of the cores comprising a grain or a flake; and
making the loaded powder using the original powder together with electrically conductive submicrometer filaments and wax so as to form a plurality of particulate compounds, a smallest dimension of each submicrometer filament being less than one micrometer and greater than or equal to one hundred nanometers, each particulate compound comprising at least one of the cores together with at least one of the filaments and a protective membrane of the wax, each articulate compound having at least one of the filaments and one of the protective membranes arranged around one of the cores.

US Pat. No. 10,655,020

CELLULAR GRAPHENE FILMS

The Regents of the Univer...

1. A reduced graphene oxide film comprising a continuous three-dimensional network of pores having a size of less than 1,000 nm, wherein the film has a density of at least about 0.1 g/cm3.

US Pat. No. 10,655,019

PRIMING MATERIAL FOR SUBSTRATE COATING

TAIWAN SEMICONDUCTOR MANU...

1. A method of film formation for an integrated circuit device, the method comprising:receiving a substrate;
selecting a first solvent and a second solvent to form a priming material, wherein the first solvent is methyl n-amyl ketone (MAK), and wherein selecting the second solvent includes selecting a solvent configured to form a dimer with the first solvent and to match a hydrogen affinity of a film-forming material;
dispensing the selected priming material over the substrate;
spreading the priming material fully across a top surface of the substrate;
dispensing the film-forming material to the substrate over the priming material;
spreading the film-forming material fully across a top surface of the priming material such that, a bottom surface of the film-forming material remains above a top surface of the priming material during the spreading, and the priming material remains underneath the film-forming material after the spreading;
evaporating the priming material, wherein the priming material is evaporated from underneath the film-forming material; and
treating the film-forming material to form a photoresist.

US Pat. No. 10,655,017

PYRIMIDOQUINAZOLINE PIGMENT, METHOD FOR MANUFACTURING PYRIMIDOQUINAZOLINE PIGMENT, AND PIGMENT COLORANT

1. A pyrimidoquinazoline pigment represented by following formula (1):wherein R1 and R2 in the formula (1) each independently represent a benzene ring or a naphthalene ring optionally having a substituent,wherein the optional substituent for each of the R1 and R2 in the formula (1) is at least one group each independently selected from the group consisting of methyl, t-butyl, phenyl, chloro, bromo, methoxy, phenoxy, and thiophenoxy.

US Pat. No. 10,655,016

ORGANIC DYE WITH IMPROVED EFFICIENCY AND USES THEREOF IN PHOTOVOLTAIC CELLS

1. Organic dye corresponding to one of the following structures (I) or (II):eD-pi-conjugated chromophore-L-A  (I)
A-L-pi-conjugated chromophore-eD  (II)
where:
eD represents an electron-donor segment,
L represents a covalent bond or a spacer segment and in particular a pi-conjugated spacer segment,
A represents an electron-attractor segment capable of forming a covalent bond with a semiconductor,
wherein the pi-conjugated chromophore comprises at least one unit of formula

where:
the radicals R1 and R2, the same or different, are an optionally substituted aryl group;
the radicals R3 to R8, the same or different, are a hydrogen, an optionally substituted alkyl group or optionally substituted aryl group; and
X1 and X2, the same or different are selected from among S, Se and O.

US Pat. No. 10,655,013

BLOW-MOLDABLE POLYAMIDE COMPOSITIONS

BASF SE, Ludwigshafen (D...

1. A thermoplastic molding composition comprisingA) from 10 to 94% by weight of a polyamide,
B) from 10 to 25% by weight of an impact modifier selected from the group consisting of
a copolymer I of
B1) from 35 to 89.9% by weight of ethylene
B2) from 10 to 60% by weight of 1-octene or 1-butene or propylene or a mixture of these and
B3) from 0.05 to 5% by weight of functional monomers, where the functional monomers are selected from the group consisting of the carboxylic acid groups, carboxylic anhydride groups, carboxylic ester groups, carboxamide groups, carboximide groups, amino groups, hydroxy groups, epoxy groups, urethane groups, oxazoline groups, and mixtures thereof,
a copolymer II of
B1) from 50 to 98% by weight of ethylene
B4) from 2 to 50% by weight of acrylic acid or methacrylic acid, and
B5) optionally from 0 to 20% by weight of functional monomers selected from the group consisting of carboxylic anhydride groups, epoxy groups, and mixtures thereof,
or a mixture of copolymer I and copolymer II,
C) from 0.1 to 10% by weight of a copolymer of
C1) from 50 to 95% by weight of styrene or substituted styrenes of the general formula I or a mixture of these

in which R is an alkyl radical having from 1 to 8 carbon atoms or a hydrogen atom and R1 is an alkyl radical having from 1 to 8 carbon atoms and n has the value 0, 1, 2, or 3, and
C2) from 5 to 50% by weight of structural units derived from one or more dicarboxylic anhydrides,
D) from 0.001 to 20% by weight of iron powder wherein the C content of component D) is from 0.01 to 1.2 g/100 g when measured by a method based on ASTM E1019,
E) from 0.05 to 3% by weight of a copper-containing stabilizer,
F) from 100 ppm to 5% by weight of alkali metal salts or alkaline earth metal salts of oxo acids of phosphorus or a mixture of these,
G) from 0 to 2% by weight of a polyethyleneimine homo- or copolymer,
H) from 0 to 60% by weight of further additives selected from the group consisting of a fibrous filler, a particulate filler, a lubricant, a nigrosin, oxidation retarders, UV stabilizers, dyes, pigments, nucleating agents, heat stabilizers, flame retardants, mold release agents, and plasticizers,
wherein:
the total of the percentages by weight of A) to H) is 100%,
the molding composition exhibits a surface roughness of class 3 or class 4,
the molding composition is free of free of copolymers comprising ethylene and (meth)acrylate co-monomers, and
the molding composition is free of a sterically hindered phenol.

US Pat. No. 10,655,012

PROCESS FOR THE PREPARATION OF POLYURETHANE SOLUTIONS BASED ON SILICON-POLYCARBONATE DIOLS

Aortech International plc...

1. A process for preparing a polyurethane solution comprising:(a) reacting a polycarbonate siloxane diol of formula I(a)
wherein R1, R2, R3, and R4 are methyl, R8 is ethyl, R9 is hexyl, R5 and R6 are propyl or butyl, R7 is O, n is 1, x is an integer of about 1-50, and z and y are integers of 0 or more, prepared by reaction of a carbonate source, with a bis(hydroxyC3-C4alkyl)(tetramethyldisiloxane), in the presence of an initiator catalyst; with a diisocyanate, to form a prepolymer;(b) stirring and heating the prepolymer to about 75-80° C.;
(c) chain extending the prepolymer by reaction with an alkylene diol, to yield a polyurethane;
(d) adding dimethylacetamide to the stirred, heated polyurethane to yield about a 15-50 wt-% solution, of said polyurethane; and
(e) cooling the solution to about 20-30° C., so as to yield a polyurethane solution having a viscosity in the range of about 1000-2000 mPas at about 17% solids.

US Pat. No. 10,655,010

AROMATIC POLYCARBONATE OLIGOMER SOLID

Honshu Chemical Industry ...

1. An aromatic polycarbonate oligomer solid comprising a repeating unit represented by the following general formula (1) and having a weight average molecular weight of 500 to 10000, a low molecular weight component of 5.0 area % or less as measured by high performance liquid chromatography, and a loose bulk density of 0.30 g/cm3 or more

US Pat. No. 10,655,009

BIODEGRADABLE COMPOSITE INSULATION MATERIAL

United Arab Emirates Univ...

1. A compression molded, blended, annealed biodegradable composite insulation material, consisting essentially of a composite of:date palm tree wood, wherein the composite comprises up to 50 wt % date palm tree wood; and
polylactic acid, wherein the composite comprises particles of date palm tree wood powder embedded in a matrix of polylactic acid to form a blended mixture, the date palm tree wood particles have a diameter less than 212 ?m,
wherein the blended mixture is compression molded and annealed to form the composite insulation material, further wherein the compression molding includes a plurality of cycles at temperatures between 100° C. and 185° C. and pressures between 0.5 tons and 3 tons and the annealing is in an oven at 95° C. for three hours.

US Pat. No. 10,655,008

BIODEGRADABLE POLYMER COMPOSITION FOR THE MANUFACTURE OF ARTICLES HAVING A HIGH HEAT DEFLECTION TEMPERATURE

NOVAMONT S.P.A., Novara ...

1. An article comprising a biodegradable polymeric composition for preparing articles having high heat deflection temperature comprising:i) 50-95% by weight, based on the sum of components i. and ii., of a polyester of lactic acid;
ii) 5-50% by weight, based on the sum of components i. and ii., of at least one aliphatic-aromatic polyester (AAPE) comprising a dicarboxylic component and a dihydroxylic component which comprise the following structural units:
-[—O—(R11)—O—C(O)—(R13)—C(O)—]-
-[—O—(R12)—O—C(O)—(R14)—C(O)—]-
 wherein the dihydroxylic component comprises units —O—(R11)—O— and —O—(R12)—O— deriving from diols, wherein R11 and R12 are the same or different and are selected from the group consisting of C2-C14 alkylenes, C5-C10 cycloalkylenes, C2-C12 oxyalkylenes, heterocyclic groups and mixtures thereof, wherein the dicarboxylic component comprises units —C(O)—(R13)—C(O)— deriving from aliphatic diacids and units —C(O)—(R14)—C(O)— deriving from an aromatic diacids, wherein R13 is selected from the group consisting of C0-C20 alkylenes and their mixtures and the molar percentage of the units deriving from aromatic diacids is higher of 50% and lower than 70% of the dicarboxylic component;
iii) 1-25% by weight, with respect to the total weight of the biodegradable polymer composition, of cellulose fibres having a length/diameter ratio <40;
iv) 1-10% by weight, with respect to the total weight of the biodegradable polymer composition, of a nucleating agent, wherein the nucleating agent comprises a mixture of polyesters comprising repeating units of 1,4-butylene succinate and talc, said mixture comprising 10-95% by weight of said polyesters;
the article having a percentage dimensional change (PDC) <1% for both its length and its width after annealing at 90° C. for 5 minutes.

US Pat. No. 10,655,007

POLYALKYLENE TEREPHTHALATE RESIN COMPOSITION

POLYPLASTICS CO., LTD., ...

1. An insert molded article obtained by performing insert molding using a polyalkylene terephthalate resin composition and an insert member comprising a metal or an inorganic solid, whereinthe polyalkylene terephthalate resin composition comprises (A) a polyalkylene terephthalate resin, and (B) an acrylic-based core-shell polymer which has an average particle size of 2 ?m or greater and in which an amount of a core layer component is at least 85% by mass but not more than 95% by mass relative to a total mass of the core layer component and a shell layer component, an amount of (B) the acrylic-based core-shell polymer is at least 10 parts by mass but not more than 30 parts by mass per 100 parts by mass of (A) the polyalkylene terephthalate resin,
the polyalkylene terephthalate resin composition further comprises (C) a filler in an amount of at least 10 parts by mass but not more than 100 parts by mass per 100 parts by mass of (A) the polyalkylene terephthalate resin,
(A) the polyalkylene terephthalate resin comprises a polybutylene terephthalate resin, the core layer component of (B) the acrylic-based core-shell polymer comprises a polymer formed using a C1 to C12 alkyl acrylate, the shell layer component of (B) the acrylic-based core-shell polymer comprises a polymer formed using a C1 to C20 alkyl methacrylate, and
the polyalkylene terephthalate resin composition is a composition wherein, when the following insert molded article A is produced, the insert molded article A satisfies the following heat shock resistance condition A, wherein
insert molded article A: an insert molded article into which an L-shaped iron plate with 21 mm in a width×90 mm×90 mm and a thickness of 1.6 mm is inserted, and in which a resin portion is an L-shaped plate with 25 mm in a width×70 mm×70 mm and a thickness of 3.6 mm, in which a minimum wall thickness in part of the resin portion is 1 mm, and
heat shock resistance condition A: in a heat shock resistance test using a thermal shock tester in which a process of performing heating at 140° C. for 1 hour and 30 minutes, subsequently lowering a temperature to ?40° C. and performing cooling for 1 hour and 30 minutes, and then raising a temperature back to 140° C. is deemed one cycle, a number of cycles performed before cracking appears in the molded article is at least 100, and
the insert member is a plate-like electrical connection conductor, and the insert member has a ratio of 12.5 or greater for a maximum width relative to a maximum thickness in a cross-section perpendicular to a lengthwise direction of a planar surface of the plate-like conductor.

US Pat. No. 10,655,006

BINDER-TREATED FIBROUS MATERIALS

CYTEC TECHNOLOGY CORP., ...

1. A fibrous material comprising a binder composition distributed therein or coated thereon,wherein said fibrous material is selected from: a woven or nonwoven fabric; a nonwoven layer of randomly arranged fibers, fiber tows, yarns, braids, textile tape suitable for automated fibre placement (AFP) and/or automated tape laying (ATL),
wherein said binder composition comprises:
(a) one or more multifunctional epoxy resins;
(b) at least one thermoplastic polymer that is soluble in one or more epoxy resins upon curing of the epoxy resin(s); and
(c) a nonionic surfactant which is a block copolymer comprising hydrophilic and hydrophobic blocks,
wherein the binder composition is present in an amount within the range of 1% to 20% by weight based on the total weight of the fibrous material, and the fibrous material is permeable to liquid resin, and
wherein the fibrous material is a dry, flexible material that is tack-free at room temperature (20° C.-25° C.).

US Pat. No. 10,655,005

EPOXY RESIN COMPOSITION

ADEKA CORPORATION, Tokyo...

1. An epoxy resin composition comprising: an epoxy resin (A), a curing agent (B) and a phosphorous-containing compound (C) indicated by the following general formula (1);wherein m indicates an integer from 2 to 10, R1 to R4 each independently indicate a hydrogen atom, an alkyl group or an aryl group, R5 indicates a hydrocarbon group that may contain an oxygen atom, a sulfur atom or a nitrogen atom, X indicates an oxygen atom or a sulfur atom, Y indicates an oxygen atom, a sulfur atom or —NR6—, and R6 indicates a hydrogen atom, an alkyl group or an aryl group andeither R1 or R2 is a hydrogen atom and the other is an alkyl group or aryl group and at the same time, either of R3 or R4 is a hydrogen atom and the other is an alkyl group or aryl group.

US Pat. No. 10,655,004

ELECTROCHEMICAL SENSOR SYSTEM

Ascensia Diabetes Care Ho...

1. A method of determining an analyte concentration, the method comprising the acts of:placing a hydrogel composition on skin, the hydrogel composition comprising a first monomer, a second monomer, a cross-linking agent, and a solvent, the first monomer being selected from Formula I
wherein the combination of R and R1 is selected from 1 carbon to 5 carbon atoms such that a 3-7 member heterocyclic moiety is formed;the second monomer being selected from Formula IV, wherein Formula IV is
whereinR2 is selected from (C3-C7)cycloalkyl, wherein the cycloalkyl is optionally substituted with one or more substituents selected from alkyls, halos, haloalkyls, cycloalkyls, nitros, and cyanos;wherein the ratio of the first monomer to the second monomer is from about 20:80 to about 80:20;
providing a sensor, the hydrogel composition located generally between and coupling the skin and the sensor; and
sampling of the interstitial fluid to determine the analyte concentration using the sensor.

US Pat. No. 10,655,003

RESIN BLEND FOR MELTING PROCESS

LG CHEM, LTD., Seoul (KR...

1. A resin blend for a melting process comprising a first resin and a second resin,wherein the first resin comprises an acrylate-based resin,
wherein the second resin comprises a (meth)acrylate-based resin to which at least one organic functional group selected from the group consisting of tertiary butyl group, isobornyl group, cyclohexyl group, and phenyl group is introduced, and has a melt viscosity difference of 0.1 to 3,000 Pa*s at a shear rate of 100 to 1,000 s?1 at a processing temperature of the resin blend and a glass transition temperature (Tg) difference of 10° C. to 100° C. with respect to the first resin,
wherein the resin blend forms a layer-separated structure in which the second resin forms on a surface of the first resin in the layer-separated structure during melt processing under shear stress,
wherein the resin blend has an impact resistance of 6.7 to 8.8 kg*cm/cm in an IZOD ?? test and of 6.5 to 9.1 kg*cm/cm in an IZOD ¼? test measured according to ASTM D256, and
wherein the resin blend has a pencil hardness of 2H to 3H measured according to ASTM 3363-74.

US Pat. No. 10,655,002

RESIN BLEND FOR MELTING PROCESS

LG CHEM, LTD., Seoul (KR...

1. A resin article comprising:a first resin; and
a second resin that is a (meth)acrylate-based resin to which at least one organic functional group selected from the group consisting of tertiary butyl group, isobutyl group, isobornyl group, cyclohexyl group, and phenyl group is introduced, that has a difference in melt viscosity from the first resin of 0.1 to 3000 pa*s at a shear rate of 100 to 1000 s?1 at a processing temperature of the resin blend, and that has a difference in glass transition temperature from the first resin of 10° C. to 100° C.,
wherein the first resin includes an acrylate-based resin,
wherein the resin article has a layer-separated structure in which the first resin is disposed inside of the layer-separated structure and the second resin is disposed on a surface of the layer-separated structure during melt processing under shear stress, and has an impact resistance of 6.7 to 8.8 kg*cm/cm in an IZOD ?? test and of 6.5 to 9.1 kg*cm/cm in an IZOD ¼? test measured according to ASTM D256, and a pencil hardness of 2H to 3H measured according to ASTM 3363-74.

US Pat. No. 10,654,991

GRANULAR MATERIAL, GRANULAR MATERIAL MANUFACTURING METHOD, THREE-DIMENSIONAL LAMINATED AND SHAPED MOLD MANUFACTURING APPARATUS, AND THREE-DIMENSIONAL LAMINATED AND SHAPED MOLD MANUFACTURING METHOD

TECHNOLOGY RESEARCH ASSOC...

1. A granular material for use in three-dimensional laminated mold shaping, comprising:(a) a mixed or coated material comprising a refractory granular raw material mixed with or coated with a first acid that, when printed with an organic binder, serves as a catalyst to activate and harden the organic binder to bind the granular material; and
(b) a hardening accelerator,
wherein the hardening accelerator is a second material that, when the mixed or coated material is printed with the organic binder, (i) undergoes a metathesis reaction to generate a second acid that catalyzes a hardening reaction of the organic binder; (ii) causes a hydration reaction with water generated during the hardening reaction to increase a rate of the hardening reaction, and (iii) absorbs moisture;
wherein the first acid contains at least one of sulfuric acid, phosphoric acid, and a sulfonic acid, and wherein the sulfonic acid contains at least one of p-toluenesulfonic acid, xylene sulfonic acid, benzene sulfonic acid, and methane sulfonic acid.

US Pat. No. 10,654,990

THERMAL STABILIZER COMPOSITION AND SYNTHETIC RESIN COMPOSITION COMPRISING SAME

ADEKA CORPORATION, Tokyo...

1. A thermal stabilizer composition, consisting of comprising:100 parts by mass of a phosphorus-based antioxidant having a phosphite structure;
0.01 to 5 parts by mass of a phenolic antioxidant; and
optionally, one or more resin additives,
wherein said phenolic antioxidant has a substructure represented by the following Formula (2?):

wherein, n represents an integer of 1 to 4;
when n is 1, X represents an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms or a combination thereof;
when n is 2, X represents an alkylidene group having 1 to 40 carbon atoms, an arylene group having 6 to 40 carbon atoms or a group represented by the following Formula (3):

wherein, R6 and R7 each independently represent an alkylidene group having 1 to 40 carbon atoms or an arylene group having 6 to 40 carbon atoms;
when n is 3, X represents an alkanetriyl group having 1 to 40 carbon atoms or a trivalent cyclic group having 6 to 40 carbon atoms,
when n is 4, X represents an alkanetetrayl group having 1 to 40 carbon atoms; and
wherein a methylene group in said alkyl group, alkoxy group, arylalkyl group, alkylidene group, alkanetriyl group and alkanetetrayl group is optionally substituted with >C?O, —O—, —S—, —CO—O—, —O—CO—, —O—CO—O—, —NR5—, a phosphine, a phosphinite, a phosphonite, a phosphite, a phosphorane, a phosphonate or a combination thereof and optionally branched, and R5 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
wherein, in formula 2?, X forms a carbon-carbon bond with the phenyl group, and
wherein said phenolic antioxidant has a molecular weight in a range of 300 to 2,000,
wherein said phosphorus-based antioxidant is represented by Formula (4):

wherein, R8 and R9 each independently represent an alkyl group having 1 to 40 carbon atoms, R10 represents a direct bond, b is 1, and T represents an alkyl group having 1 to 40 carbon atoms; and
wherein the one or more resin additives are selected from the group consisting of thioether-based antioxidant, an ultraviolet absorber, a hindered amine-based light stabilizer, a nucleating agent, a flame retardant, a flame retardant aid, a lubricant, a filler, a metallic soap, a hydrotalcite, an antistatic agent, a pigment, a dye, and a combination thereof.

US Pat. No. 10,654,989

METHOD TO ENHANCE RELEASE OF POLYMERS FROM HOT METAL SURFACES

Rohm and Haas Company, C...

1. A method comprisingcontacting a polymer composition with a metal processing surface wherein the metal processing surface is at a temperature of equal to or greater than 90° C.,
wherein the polymer composition comprises one or more base polymers selected from the group consisting of polyvinyl halides, poly(meth)acrylics, polycarbonates, olefin-based polymers, and polystryrenes and a lubricant package which comprises at least one release agent of the following formulas
where R is an alkyl group having 6 or more carbon atoms, M is a metal or cation, and X may be absent or selected from the group consisting of aromatic groups and ester groups.

US Pat. No. 10,654,988

POLYOLEFIN COMPOSITION

1. A polyolefin composition comprising:(a) a polyolefin polymer;
(b) 1,3:2,4-bis-O-[(3,4-dichlorophenyl)methylene]-D-glucitol; and
(c) an amide compound selected from the group consisting of compounds conforming to a structure of Formula (I) or Formula (X) below
wherein R1 and R11 are independently selected from the group consisting of C7-C27 alkyl groups and C7-C27 alkenyl groups, and R15 is selected from the group consisting of C1-C8 alkanediyl groups.

US Pat. No. 10,654,985

MICROPOROUS POLYMERIC COMPOSITION

COMMONWEALTH SCIENTIFIC A...

1. A microporous polymeric composition comprising 60% to 90% by weight of a matrix polymer selected from at least one of substituted polyacetylenes and polymers of intrinsic microporosity (PIMs) and having a fractional free volume of at least 0.1 and dispersed particles comprising 5% to 25% by weight of the microporous polymeric composition of hypercrosslinked polymer comprising optionally substituted aryl groups (Ar) covalently linked by methylene bridging groups (CH2) providing a link with repeating units —(Ar—CH2—Ar—CH2)n- wherein n is the number of repeating units.

US Pat. No. 10,654,983

POROUS FILM AND METHOD OF FORMING POROUS FILM

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

1. A porous film comprising:at least one porous polyimide film that includes a polyimide resin, an organic amine compound, and a resin other than a polyimide resin, and that does not include a polar aprotic solvent,
wherein a content of the organic amine compound is 0.001% by weight or higher with respect to a total weight of the porous polyimide film and
the shape of pores is substantially spherical.

US Pat. No. 10,654,979

AMPHIPHILIC GRAFT COPOLYMERS

Becton, Dickinson and Com...

1. A medical device formed from a blend comprising:a base polymeric formulation comprising at least a polymer or co-polymer of propylene; and
an additive comprising a polypropylene-poly(ethylene oxide)-poly(propylene oxide) amphiphilic graft copolymer (PPMA-g-PEO-PPO);
the PPMA-g-PEO-PPO being present in the blend in an amount in the range of about 0.01 to about 5.0% by weight of the blend;
wherein the PPMA-g-PEO-PPO is according to Formula (I):

wherein Me is CH3; the molar value of m is in the range from 5 to 25 mole percent; and
the molar value of n is in the range from 75 to 95 mole percent; the molar value of x is in the range from >0 to 40 propylene oxide units; and the molar value of y is in the range from >0 to 80 ethylene oxide units, and
wherein the medical device is in the form of tubing.

US Pat. No. 10,654,976

METHOD FOR PRODUCING A CROSS-LINKED SILOXANE NETWORK

1. A method for producing a cross-linked siloxane network, the method comprising the steps of:(a) providing a first part comprising (i) a first siloxane compound comprising at least one cyclic siloxane moiety and (ii) a second siloxane compound comprising a plurality of siloxane moieties, wherein 50 mol. % or more of the siloxane moieties in the second siloxane compound are selected from the group consisting of moieties of Formula (LXXX) and moieties of Formula (XC)
wherein R81, R82, and R91 are independently selected from the group consisting of haloalkyl groups, aralkyl groups, aryl groups, substituted aryl groups, heteroaryl groups, and substituted heteroaryl groups, wherein about 25 mol. % or more of the siloxane moieties in the second siloxane compound are moieties of Formula (XC), and wherein about 10 mol. % or more of silicon atoms in the second siloxane compound have one or more hydroxy groups covalently bound thereto; and wherein Formula (LXXX) constitutes a D unit and Formula (XC) constitutes a T unit;(b) providing a second part, the second part comprising a hydroxide salt;
(c) combining the first part and the second part to produce a reaction mixture;
(d) heating the reaction mixture to a temperature sufficient for the hydroxide salt to open the ring of the cyclic siloxane moiety; and
(e) maintaining the reaction mixture at an elevated temperature so that at least a portion of the opened cyclic siloxane moieties react to produce a cross-linked siloxane network.

US Pat. No. 10,654,972

METHOD FOR PRODUCING THERMOPLASTIC RESIN

MITSUBISHI GAS CHEMICAL C...

1. A method for producing a thermoplastic resin by reacting reactants comprising a dihydroxy compound, whereinthe dihydroxy compound comprises a dihydroxy compound represented by the following formula (1), wherein
the total weight of a compound represented by the following formula (A), a compound represented by the following formula (B), and a compound represented by the following formula (C) in the dihydroxy compound is 1,500 ppm or less, based on 100 parts by weight of the dihydroxy compound represented by the formula (1):

wherein X represents an alkylene group containing 1 to 4 carbon atoms,
wherein the dihydroxy compound further comprises 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorine, and
the molar ratio of the compound of formula (1) to the 9,9-bis(4-(2-hydroxyethoxy)-3-phenylphenyl)fluorine is 40/60 to 50/50, and
wherein (A), (B), and (C) are:

US Pat. No. 10,654,971

AROMATIC POLYCARBONATE OLIGOMER SOLID

Honshu Chemical Industry ...

1. An aromatic polycarbonate oligomer solid comprising a repeating unit represented by the following general formula (1) and having a weight average molecular weight of 500 to 10000, a low molecular weight component of 5.0 area % or less as measured by high performance liquid chromatography, and a loose bulk density of 0.21 g/cm3 or more

US Pat. No. 10,654,970

CAMERA MODULE-USE LIQUID CRYSTALLINE POLYESTER RESIN COMPOSITION AND CAMERA MODULE-USE MOLDED PRODUCT FORMED THEREOF

Toray Industries, Inc., ...

1. A liquid crystalline polyester resin composition for use in camera modules, the resin composition comprising 20 to 45 parts by weight of spherical silica particles (B) having an average particle diameter of 15 ?m or more and less than 30 ?m in 100 parts by weight of a liquid crystalline polyester resin (A), wherein the liquid crystalline polyester resin (A) is composed of structural units (I), (II), (III), (IV) and (V), and wherein the content of structural unit (I) is from 65 to 80% by mole relative to the total content of structural units (I), (II) and (III), and the content of structural unit (II) is from 55 to 85% by mole relative to the total content of structural units (II) and (III), and the content of structural unit (IV) is from 50 to 95% by mole relative to the total content of structural units (IV) and (V)

US Pat. No. 10,654,969

THIN FILM AND METHOD FOR MANUFACTURING THE SAME AND COPPER CLAD LAMINATE

INDUSTRIAL TECHNOLOGY RES...

1. A thin film, comprising:a polymer formed by reacting (a) p-hydroxybenzoic acid, (b) 6-hydroxy 2-naphthoic acid and (c) branched-monomer,
wherein (c) branched-monomer is
or a combination thereof, wherein R is aryl group, heteroaryl group, or cycloalkyl group, and each of R1 is independently —OH, —NH2, or —COOH;wherein a molar ratio of (a) p-hydroxybenzoic acid over (b) 6-hydroxy 2-naphthoic acid is between 50:50 and 90:10;
wherein a molar ratio of (c) branched-monomer over the sum of (a) p-hydroxybenzoic acid and (b) 6-hydroxy 2-naphthoic acid is between 0.25:100 and 0.5:100; and
wherein the polymer has an inherent viscosity of 4 dL/g to 6 dL/g.

US Pat. No. 10,654,967

POLYMER COMPOUND AND LIGHT-EMITTING ELEMENT USING SAME

Sumitomo Chemical Company...

1. A polymer compound comprising a constitutional unit represented by the formula (1A) and a constitutional unit represented by the formula (2A):whereinRAm and RBm each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups each optionally have a substituent, and when a plurality of RBm are present, they may be the same or different,
Ar1m and Ar2m each independently represent an arylene group or a divalent heterocyclic group, and these groups each optionally have a substituent, and A1m and RAm may be combined together to form a ring together with the nitrogen atom to which they are attached, and Ar2m and RBm may be combined together to form a ring together with the nitrogen atom to which they are attached,
ArM represents an aromatic hydrocarbon group or a heterocyclic group, and these groups each optionally have a substituent, and when a plurality of ArM are present, they may be the same or different,
m1, and m3 each independently represent an integer of 1 to 4,
m2 represents an integer of 0 to 5,
when a plurality of m2 and m3 are present, they may be the same or different at each occurrence,
LM represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N(R?)—, an oxygen atom or a sulfur atom, and these groups each optionally have a substituent, and R? represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups each optionally have a substituent, and when a plurality of LM are present, they may be the same or different, and
XM represents a monovalent group containing a crosslinkable group represented by the formula (XL-9), the formula (XL-10), the formula (XL-11), the formula (XL-12), the formula (XL-13) or the formula (XL-16), and these groups each optionally have a substituent, and when a plurality of XM are present, they may be the same or different:
wherein * represents a binding site;andRAn and RBn each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups each optionally have a substituent, and when a plurality of RBn are present, they may be the same or different,
Ar1n, Ar2n and ArLn each independently represent an arylene group or a divalent heterocyclic group, and these groups each optionally have a substituent, and Ar1n and RAn may be combined together to form a ring together with the nitrogen atom to which they are attached, Ar2n and RBn may be combined together to form a ring together with the nitrogen atom to which they are attached, and when a plurality ArLn is present, they may be the same or different at each occurrence,
ArN represents an aromatic hydrocarbon group or a heterocyclic group, and these groups each optionally have a substituent, and when a plurality of ArN are present, they may be the same or different,
n1 and n3 each independently represent an integer of 1 to 4,
n2 represents 1 or 2,
Ln represents an integer of 0 to 4,
LN represents an alkylene group, a cycloalkylene group, a divalent heterocyclic group, a group represented by —N(R?)—, an oxygen atom or a sulfur atom, and these groups each optionally have a substituent, and R? represents the same meaning as described above, and when a plurality of LN are present, they may be the same or different, and
XN represents a monovalent group containing a crosslinkable group represented by the formula (XL-1), the formula (XL-2), the formula (XL-3), the formula (XL-4), the formula (XL-5), the formula (XL-6), the formula (XL-7), the formula (XL-8), the formula (XL-14) or the formula (XL-15), and these groups each optionally have a substituent, and when a plurality of XN are present, they may be the same or different:
whereinnXL represents an integer of 0 to 5, and when a plurality of nXL are present, they may be the same or different,
RXL represents a methylene group, an oxygen atom or a sulfur atom, and when a plurality of RXL are present, they may be the same or different, and
* represents the same meaning as described above.

US Pat. No. 10,654,965

METHOD OF PRODUCING FIVE-CARBON RING-CONTAINING COMPOUND AND FIVE-CARBON RING DERIVATIVE-CONTAINING POLYURETHANE, AND FIVE-CARBON RING DERIVATIVE-CONTAINING POLYURETHANE

NATIONAL CHUNG SHAN INSTI...

1. A method of producing a five-carbon ring derivative-containing polyurethane, the method comprising the steps of:(a) allowing a diisocyanate compound to react with a polyethylene glycol compound and thus produce a prepolymer; and
(b) allowing the prepolymer to react continuously with a 5-carbon cyclic compound expressed by formula (I) or formula (II) below,


and thus produce a five-carbon ring derivative-containing polyurethane.

US Pat. No. 10,654,963

SOLID ELECTROLYTE COMPOSITION, BINDER FOR ALL-SOLID-STATE SECONDARY BATTERIES, AND ELECTRODE SHEET FOR BATTERIES AND ALL-SOLID-STATE SECONDARY BATTERY EACH USING SAID SOLID ELECTROLYTE COMPOSITION

FUJIFILM Corporation, To...

1. A solid electrolyte composition comprising:an inorganic solid electrolyte having conductivity of an ion of metal belong to Group 1 or 2 in the periodic table; and
a high polymer binder,
wherein the high polymer binder is formed of a polymer having a hard segment and a soft segment, and
wherein the hard segment forming the high polymer binder contains at least any one bond of an amide bond, an urea bond, an urethane bond, and an imide bond, and the polymer forming the high polymer binder has at least any one of repeating structures expressed by Formulae (II-1) to (II-5) of Group II below, as the soft segment,

in Formulae (II-1), and (II-3) to (II-5), R21 represents a hydrogen atom or an alkyl group, R22 represents a substituent group which contains a polyalkylene oxide chain, a polycarbonate chain, or a polyester chain and of which a weight average molecular weight is 200 to 200,000, R23 represents a linking group which contains a polyalkylene oxide chain, a polycarbonate chain, or a polyester chain and of which a weight average molecular weight is 200 to 200,000, and * represents a bonding position, and
in Formulae (II-2), R23 represents a linking group which contains a polycarbonate chain and of which a weight average molecular weight is 200 to 200,000, and * represents a bonding position.

US Pat. No. 10,654,960

DUAL-MECHANISM THICKENING AGENTS FOR HYDRAULIC FRACTURING FLUIDS

PILOT POLYMER TECHNOLOGIE...

1. A dual-mechanism thickening agent comprising a gel-forming star macromolecule, wherein the gel-forming star macromolecule is represented by Formula (I):
wherein:
Core represents a crosslinked polymeric segment;
P1 represents a hydrophobic polymeric segment comprised predominantly of repeat units of monomeric residues of polymerized hydrophobic monomers;
P2 represents a hydrophilic polymeric segment comprised predominantly of repeat units of monomeric residues of polymerized hydrophilic monomers;
P3 represents a hydrophilic polymeric segment comprised predominantly of repeat units of monomeric residues of polymerized hydrophilic monomers;
P4 represents a hydroxyl-containing segment (homopolymeric or copolymeric) comprised of repeat units of monomeric residues, where at least one of the monomeric residues or a plurality of the monomeric residues is a hydroxyl-containing monomeric residue, of polymerized monomers;
P5 represents a hydrophilic polymeric segment comprised predominantly of repeat units of monomeric residues of polymerized hydrophilic monomers;
q1 represents the number of repeat units in P1 and has a value between 1 and 50;
q2 represents the number of repeat units in P2 and has a value between 30 and 2000;
q3 represents the number of repeat units in P3 and has a value between 30 and 2000;
q4 represents the number of repeat units in P4 and has a value between 1 and 50;
q5 represents the number of repeat units in P5 and has a value between 30 and 2000;
r represents the number of polymeric arms covalently attached to the Core;
s represents the number of hydroxyl-containing arms covalently attached to the Core; and
t represents the number of hydrophobic-containing copolymeric arms covalently attached to the Core and has a value of 1 or more.

US Pat. No. 10,654,957

METHOD FOR MANUFACTURING COPOLYMER AND RUBBER COMPOSITION CONTAINING THE SAME

Korea Kumho Petrochemical...

1. A method of preparing a copolymer, the method comprising:(a) polymerizing an aromatic vinyl monomer and a conjugated diene-based monomer with a solvent, a first randomizing agent, and a catalyst to prepare a first copolymer including the aromatic vinyl monomer in an amount of 15 to 40 wt %; and
(b) reacting the first copolymer with one or more of a second randomizing agent different from the first randomizing agent and an additional aromatic vinyl monomer to prepare a second copolymer.

US Pat. No. 10,654,956

ETHYLENE ALPHA-OLEFIN COPOLYMERS AND METHODS

Equistar Chemicals, LP, ...

1. An ethylene alpha-olefin copolymer comprising:an ethylene monomer; and
an alpha-olefin monomer;
wherein the ethylene alpha-olefin copolymer comprises—
(i) a density of about 0.915 g/mL to about 0.918 g/mL,
(ii) a rheological polydispersity index greater than 0.8,
(iii) a melt index of about 0.4 dg/10 min to about 2.0 dg/10 min, and
(iv) a CEF T50 of 84° C. or less.

US Pat. No. 10,654,955

ETHYLENE-BASED POLYMERS COMPRISING UNITS DERIVED FROM CARBON MONOXIDE AND A RHEOLOGY MODIFYING AGENT

Dow Global Technologies L...

1. A composition comprising an ethylene-based polymer, comprising at least the following:A) a unit derived from Carbon Monoxide (CO); and
B) a unit derived from at least one Rheology Modifying Agent (RMA) selected from the following i) through vi):
i) RMA 1:

wherein, for RMA1, R1 is H or alkyl,
n is from 1 to 50,
R2 is selected from H or an alkyl,
R3 is selected from H or an alkyl;
ii) RMA2:

wherein, for RMA2, R4 and R5 are each independently H or an alkyl,
m is from 1 to 50;
iii) RMA3:

wherein, for RMA3, R6 and R9 are each independently H or an alkyl,
p is from 1 to 50;
R7 is selected from H or an alkyl,
R8 is selected from H or an alkyl;
iv) RMA4:

wherein R10 is hydrogen or an alkyl,
the notation “” is a hydrocarbon chain comprising from 2 to 50 carbon atoms, and wherein the hydrocarbon chain is linear, branched, or comprises a saturated hydrocarbon ring structure;
v) RMA5

wherein q is from 2 to 20; R11 is selected from H or alkyl; R12 is selected from H or alkyl; R13 is selected from H or alkyl; R14 is selected from H or alkyl; or
vi) any combination of i) through v).

US Pat. No. 10,654,952

NITROGEN TITANIUM COMPLEX, CATALYTIC SYSTEM COMPRISING SAID NITROGEN TITANIUM COMPLEX AND PROCESS FOR THE (CO)POLYMERIZATION OF CONJUGATED DIENES

Versalis S.P.A., San Don...

1. A nitrogen titanium complex having general formula (I):wherein:R1 represents a hydrogen atom; or is selected from linear or branched C1-C20 alkyl groups, optionally halogenated, cycloalkyl groups optionally substituted or aryl groups optionally substituted;
R2, R3, R4 and R5, identical or different, represent a hydrogen atom; or are selected from linear or branched C1-C20 alkyl groups, optionally halogenated, cycloalkyl groups optionally substituted, aryl groups optionally substituted, nitro groups, hydroxyl groups or amino groups;
Y represents a NH—R6 group wherein R6 represents a hydrogen atom, or is selected from linear or branched C1-C20 alkyl groups, optionally halogenated, cycloalkyl groups optionally substituted or aryl groups optionally substituted; or a N—R7 group wherein R7 is selected from linear or branched C1-C20 alkyl groups, optionally halogenated, cycloalkyl groups optionally substituted or aryl groups optionally substituted;
X1, X2, X3 and X4, identical or different, represent a halogen atom; or are selected from linear or branched C1-C20 alkyl groups, —OCOR8 groups or groups —OR8 wherein R8 is selected from linear or branched C1-C20 alkyl groups; or one of X1, X2 and X3 is selected from ethers; and
n is 1 in the case wherein Y represents a NH—R6 group wherein R6 has the same meanings reported above; or n is 0 in the case wherein Y represents a N—R7 group wherein R7 has the same meanings reported above, or n is 0 in the case wherein one of X1, X2 and X3 is selected from ethers.

US Pat. No. 10,654,950

VINYL CHLORIDE-BASED POLYMER, METHOD OF PREPARING THE SAME, AND PLASTISOL INCLUDING THE POLYMER

LG CHEM LTD., Seoul (KR)...

1. A vinyl chloride-based polymer, with a particle size distribution which represents a weight ratio of polymer particles belonging to a certain particle diameter range to total polymer particles,wherein 65 wt % to 80 wt % of the weight of the total polymer particles has a particle diameter of 0.1 ?m to 0.29 ?m,
wherein 20 wt % to 35 wt % of the weight of the total polymer particles has a particle diameter of 0.3 ?m to 3.0 ?m,
wherein the polymer particles having a particla diameter of 0.3 ?m to 3.0 ?m comprise polymer particles having a particle diameter of 1.0 ?m to 3.0 ?m, and
wherein the polymer has a peak particle diameter (Dp) of 0.17 ?m to 0.29 ?m.

US Pat. No. 10,654,946

CATALYST COMPONENTS FOR THE POLYMERIZATION OF OLEFINS

Basell Poliolefine Italia...

1. A solid catalyst component for the polymerization of olefins comprising:Mg, Ti and an electron donor of formula (I)
whereinR1 and R7 groups, equal to or different from each other, are selected from C1-C15 hydrocarbon groups,
R2 group is selected from C1-C10 hydrocarbon groups, and
R3 to R6 groups, independently, are selected from hydrogen or C1-C15 hydrocarbon groups which can be fused together to form one or more cycles.

US Pat. No. 10,654,945

PROCESS FOR EXTRACTING LATEX, RESIN AND RUBBER FROM GUAYULE PLANTS

Versalis S.P.A., San Don...

1. Process for extracting latex, resin and rubber from guayule plants, comprising:a. harvesting the guayule plants;
b. defoliating said plants;
c. preserving the defoliated plants in an environment under controlled temperature and relative humidity, for a time of between 7 and 21 days, such that the residual moisture present in the plant is maintained in the range of 30-45%;
d. immersing the defoliated plants in a basic aqueous solution which comprises a stabilising system;
e. grinding said defoliated plants immersed in said basic aqueous solution to obtain an aqueous suspension of plant material comprising plant fragments;
f. subjecting the aqueous suspension obtained in step “e” to filtration/pressing to separate a first miscella comprising said latex from a first bagasse;
g. recovering the concentrated latex from said first miscella;
h. dispersing said first bagasse in a polar solvent system, comprising at least one polar organic solvent and a stabilising system, to obtain a suspension;
i. subjecting the suspension obtained in step “h” to filtration/pressing to separate a second miscella comprising said resin from a second bagasse;
j. removing the at least one polar organic solvent from said second miscella to obtain the concentrated resin;
k. removing the at least one polar organic solvent from the second bagasse obtained in step “i”;
l. dispersing said desolventised second bagasse obtained in step “k” in a nonpolar solvent system, comprising at least one nonpolar organic solvent and a stabilising system, to obtain a suspension;
m. subjecting the suspension obtained in step “l” to filtration/pressing to separate a third miscella comprising said rubber from a third bagasse;
n. removing the at least one nonpolar organic solvent from the third miscella to obtain the rubber in the solid state;
o. removing the at least one nonpolar organic solvent from the third bagasse obtained in step “m”.

US Pat. No. 10,654,942

METHODS AND APPARATUS FOR FALSE POSITIVE MINIMIZATION IN FACIAL RECOGNITION APPLICATIONS

15 Seconds of Fame, Inc.,...

1. An apparatus, comprising:a memory; and
a processor operatively coupled to the memory, the processor configured to, at a first time, receive data from a user device, the processor configured to store the data in a user profile data structure, the user profile data structure including facial recognition data of a user associated with the user device and defined based on at least one of two-dimensional facial recognition analytics, three-dimensional facial recognition analytics, or convolutional neural nets (CNN), the processor configured to receive, at a second time different from the first time, at least one image from an image capture device,
the processor configured to identify (1) a venue based at least in part on data associated with the at least one image and (2) an image location within the venue based at least in part on a set of image characteristics within the received at least one image, the processor configured to retrieve, from a database, a plurality of user profile data structures including the user profile data structure, the processor configured to determine whether the user is at the venue based on at least a first portion of the data stored in the user profile data structure from the plurality of user profile data structures,
the processor configured to, when the user is at the venue, determine whether the user associated with the user profile data structure can be identified in the at least one image by analyzing the at least one image with respect to the facial recognition data of the user based on at least one of the two-dimensional facial recognition analytics, the three-dimensional facial recognition analytics, or the CNN to identify a facial recognition confidence score,
the processor configured to (1) determine a user location within the venue based on at least a second portion of the data stored in the user profile data structure, (2) compare the user location within the venue to the image location, and (3) increase the facial recognition confidence score when the user location within the venue and the image location are within a predetermined distance of each other, the processor configured to associate the at least one image with the user profile data structure based on the facial recognition confidence score meeting a predetermined criterion,
the processor configured to not perform facial recognition analysis on the at least one image with respect to the facial recognition data when the user is not at the venue.

US Pat. No. 10,654,916

COMPOSITIONS AND METHODS FOR THE TREATMENT OF NEUROMYELITIS OPTICA

THE REGENTS OF THE UNIVER...

1. A method of treating a subject with neuromyelitis optica (NMO) spectrum disease comprising administering to said subject a reagent comprising an anti-aquaporin-4 (AQP4) antibody or an antigen binding fragment thereof, wherein said AQP4 antibody or an antigen binding fragment thereof comprises a mutated Fc region of IgG1 antibody which lacks effector functions of an intact antibody, wherein the effector functions are activation of complement and recruitment of immune cells, andwherein said AQP4 antibody or an antigen binding fragment thereof comprises
i) a light chain variable region comprising SEQ ID NO: 6, and a heavy chain variable region comprising SEQ ID NO: 8;
ii) a light chain variable region comprising SEQ ID NO: 10, and a heavy chain variable region comprising SEQ ID NO: 12; or
iii) a light chain variable region comprising SEQ ID NO: 19, and a heavy chain variable region comprising SEQ ID NO: 17.

US Pat. No. 10,654,913

FIBRONECTIN TYPE III DOMAIN BASED SCAFFOLD COMPOSITIONS, METHODS AND USES

Janssen Biotech, Inc., H...

1. A library produced by a method of constructing a library of a protein scaffold based on a fibronectin type III (FN3) domain derived from a consensus sequence of an FN3 domain, comprising the steps of:providing a polypeptide derived from a consensus sequence of an FN3 domain having at least 90% identity to the amino acid sequence of SEQ ID NO:16; and
introducing diversity into copies of the polypeptide to form the protein scaffold library.

US Pat. No. 10,654,897

?-HAIRPIN PEPTIDOMIMETICS

POLYPHOR AG, Allschwil (...

1. A compound of the general formula (I),wherein the single elements T or P are connected in either direction from the carbonyl (C?O) point of attachment to the nitrogen (N) of the next element andwherein
T1 is DPro; DAzt; DAla; DTyr; DDab; DThr; NMeAla; DLys; DArg; or Sar;
T2 is Pro; Ala; Leu; NMeAla; Tyr; Phe; Dab; Dap; Orn; Lys; or Arg;
P1 is Leu; Ile; Val; Cpa; Cpg; Phe; Nva; Abu; or Trp;
P2 is Cys; Hcy; Pen; Tyr; Dab; Dap; Lys; Thr; Ser; Asp; Glu; Pra; or Abu(4N3);
P3 is Val; tBuGly; or Tyr;
P4 is Cys; Hcy; Pen; Ala; Val; Dap; Dab; Lys; Asp; Glu; Arg; Asn; Thr; Pra; or Abu(4N3);
P5 is Orn; Dap; Dab; or Thr;
P6 is Gly; Dab; or DDab;
P7 is Dab;
P8 is Trp; Phe; or Leu;
P9 is Cys; Hcy; Pen; Ala; Tyr; Dab; Dap; Lys; Asp; Glu; Ser; Thr; Pra; or Abu(4N3);
P10 is Val; tBuGly; Chg; Phg; or Tyr;
P11 is Cys; Hcy; Pen; Ala; Val; Ser; Thr; Asp; Glu; Dap; Dab; Lys; Pra; or Abu(4N3);
P12 is Val; Tyr; His; Dab; Ser; or Thr;
wherein P2 and P11 taken together and/or P4 and P9 taken together can form interstrand linking bis(amino acid)-structures based on the linkage of two L- or D-amino acid residues following
connection of the side chain of Cys; Hcy; or Pen; with the side chain of Cys; Hcy; or Pen; by a disulfide linkage; or
connection of the side chain of Dap; Dab; or Lys; with the side chain of Asp; or Glu; by a lactam linkage; or
connection of the side chain of Dap; with the side chain of Dap; by an urea linkage; or
connection of the side chain of Pra with the side chain of Abu(4N3) by a 1,4-disubstituted 1,2,3-triazole-containing linkage;
or a pharmaceutically acceptable salt thereof;
with the proviso that
if no interstrand linkage is formed; and P2 is Tyr; Dab; Dap; or Lys;
or
P2 and P11 taken together; or P2 and P11; and P4 and P9 taken together; form interstrand linking bis(amino acid)-structures based on the linkage of two L- or D-amino acid residues following
connection of the side chain of Cys; or Hcy; with the side chain of Cys; or Hcy; by a disulfide linkage; or
connection of the side chain of Dap; Dab; or Lys; with the side chain of Asp; or Glu; by a lactam linkage; or
connection of the side chain of Dap; with the side chain of Dap; by an urea linkage;
or
P2 is Tyr; Dab; Dap; or Lys;
and P4 and P9 taken together form interstrand linking bis(amino acid)-structures based on the linkage of two L- or D-amino acid residues following
connection of the side chain of Cys; or Hcy; with the side chain of Cys; or Hcy; by a disulfide linkage; or
connection of the side chain of Dap; Dab; or Lys; with the side chain of Asp; or Glu; by a lactam linkage; or
connection of the side chain of Dap; with the side chain of Dap; by an urea linkage;
and
T1 is DPro; or DAzt;
then T2 is Arg;
and with the further proviso that
if no interstrand linkage is formed;
and
T1 is DPro;
and
P2 is Thr; Ser; Asp; or Glu;
then
T2 is Ala; Leu; NMeAla; Tyr; Phe; Dab; Dap; Orn; Lys; or Arg.

US Pat. No. 10,654,896

FOXP3-BINDING PEPTIDES AND USES THEREOF

1. A peptide or a pharmaceutically salt thereof, the peptide being selected from the group consisting of:(a) a peptide of formula (I):

wherein:
R1 and R2, taken together, form a birradical linker; and
R2? is hydrogen;
the linker birradical formed by R1 and R2 being bound to the amino terminal group of the amino acid residue at position 1 and the alpha carbon of the amino acid residue at position 15, and being selected from the group consisting of: C(?O), (C1-C10)alkyl-NR5—C(?O), (C2-C10)alkenyl-NR6—C(?O), (C2-C10)alkynyl-NR7—C(?O), (C1-C10)alkyl-NR8—C(?O)—(C1-C10)alkyl-NR9C(?O), (C1-C10)alkyl-C(?O)—(C1-C10)alkyl-NR10—C(?O), (C1-C10)alkyl-O—(C1-C10)alkyl-NR11—C(?O), (C1-C10)alkyl-C(?O)—NR12—(C1-C10)alkyl-NR13C(?O), (C1-C10)alkyl-NR14R15—(C1-C10)alkyl-NR16—C(?O), (C1-C10)alkyl-C(?O)—O—(C1-C10)alkyl-NR17—C(?O), (C1-C10)alkyl-O—C(?O)—(C1-C10)alkyl-NR18—C(?O), (C1-C10)alkyl-C(?O), (C2-C10)alkenyl-C(?O), (C2-C10)alkynyl-C(?O), (C1-C10)alkyl-O—(C1-C10)alkyl-C(?O), (C1-C10)alkyl-C(?O)—(C1-C10)alkyl-C(?O), (C1-C10)alkyl-O—C(?O)—(C1-C10)alkyl-C(?O), (C1-C10)alkyl-C(?O)—O—(C1-C10)alkyl-C(?O), (C1-C10)alkyl-NR19R20—(C1-C10)alkyl-C(?O), (C1-C10)alkyl-NR21—C(?O)—(C1-C10)alkyl-C(?O), (C1-C10)alkyl-C(?O)—NR22—(C1-C10)alkyl-C(?O), and
or, alternatively,
R1 is a monoradical selected from the group consisting of hydrogen, —C(?O)—CH2—NH—C(?O)—(C1-C5)alkyl, and —C(?O)—(C1-C20)alkyl;
one of R2 and R2? is a hydrogen radical and the other is a monoradical selected from the group consisting of —C(?O)NR3R4, and —C(?O)OH;
R3 and R4 are monoradicals the same or different and are selected from the group consisting of: hydrogen and (C1-C10)alkyl; and
R5 to R22 are monoradicals selected from the group consisting of: hydrogen, (C1-C10)alkyl, (C2-C10)alkenyl, and (C2-C10)alkynyl;
the (C1-C10)alkyl, (C2-C10)alkenyl, and (C2-C10)alkynyl being non-substituted or substituted,
wherein
the substituted (C1-C10)alkyl is substituted by one or more radicals selected from the group consisting of: halogen, —OR23, —NO2, —NR24R25, —SR26, —SO2R27, —CO2R28, (C1-C10)alkyl, (C1-C10)alkyl-O—, and a (C1-C6)cycloakyl, being R23 to R28 monoradicals, the same or different, and selected from the group consisting of: —H, (C1-C10)alkyl, (C2-C10)alkenyl, and (C1-C10)alkynyl;
the substituted (C2-C10)alkenyl is substituted by one or more radicals selected from the group consisting of: halogen, —OR29, —NO2, —NR30R31, —SR32, —SO2R33, —CO2R34, (C1-C10)alkyl, (C1-C10)alkyl-O—, and a (C1-C6)cycloakyl, being R29 to R34 monoradicals, the same or different, and selected from the group consisting of: —H, (C1-C10)alkyl, (C2-C10)alkenyl, and (C1-C10)alkynyl;
the substituted (C2-C10)alkynyl is substituted by one or more radicals selected from the group consisting of: halogen, —OR35, —NO2, —NR36R37, —SR38, —SO2R39, —CO2R40, (C1-C10)alkyl, (C1-C10)alkyl-O—, and a (C1-C6)cycloakyl, being R35 to R40 monoradicals, the same or different, and selected from the group consisting of: —H, (C1-C10)alkyl, (C2-C10)alkenyl, and (C1-C10)alkynyl;
X1 and X3 are the same or different and represent D- or L-non polar amino acids; and
X2, X4, and X5 represent amino acid residues, the same or different;
(b) a peptide having at least 80% of sequence identity with peptide of formula (I) which maintains the ability to bind FoxP3 and inhibit FoxP3 activity in vitro and/or in vivo; and
(c) a fragment of the peptide defined in (a) or in (b), wherein said fragment comprises:
a portion of at least 11 consecutive amino acids of the peptide defined in (a) or in (b), wherein the fragment further comprises X1 and X2 as defined above in (a); and wherein the peptide maintains the ability to bind FoxP3 and inhibit FoxP3 activity in vitro and/or in vivo.

US Pat. No. 10,654,891

CROSS-LINKED PEPTIDES CONTAINING NON-PEPTIDE CROSS-LINKED STRUCTURE, METHOD FOR SYNTHESIZING CROSS-LINKED PEPTIDES, AND NOVEL ORGANIC COMPOUND USED IN METHOD

Jitsubo Co., Ltd., Tokyo...

1. A compound represented by the following formula M-4:
wherein,
X may be the same or different and represents an alkylene chain having 2 to 12 carbon atoms,
Z represents an optionally substituted alkyl group having 1 to 30 carbon atoms, an optionally substituted acyl group having 1 to 36 carbon atoms, polyethylene glycol, a tBoc group, a Fmoc group, a Cbz group or a Nosyl group,
[A] may be the same or different and represents a peptide having 1 to 20 residues composed of amino acids or unnatural amino acids or a single bond,
[B] may be the same or different and represents a peptide having 1 to 20 residues composed of amino acids or unnatural amino acids or a single bond,
the sum of the numbers of amino acids of [A] and [B] present in the
side chain attached to each [X] is at least 1, and each of them may have a side chain protective group,(a) may be the same or different and represents —NH— or a single bond,
(b) may be the same or different and represents —(C?O)— or a single bond,
R1 may be the same or different and represents a hydrogen atom or a methyl group,
R4 may be the same or different and represents a hydrogen atom or a methyl group,
P1 may be the same or different and represents an amino protective group or a hydrogen atom,
P2 may be the same or different and represents a —O-ester protective group, a —NH-benzyl protective group, an amino group or a hydroxyl group.

US Pat. No. 10,654,890

CYCLIC PEPTIDE DERIVATIVE, METHOD FOR PREPARING SAME AND COMPOSITION THEREOF

BIOCOCOON LABORATORIES, I...

1. A method of increasing expression of NGF and/or VGF by administering to a subject in need thereof a therapeutically effective amount of a cyclic peptide derivative represented by the following general formula (1)in the formula, m is 0 to 3, n?1, R1 to R6 are independently a hydrogen atom or a hydrocarbon group, R7 and R8 are independently a carboxyl group or a salt thereof, or an alkoxycarbonyl group, R9 is a hydrocarbon group, a hydroxyl group, an alkoxy group, or an alkylcarbonyloxy group, R10 and R11 are independently a hydrogen atom, a hydrocarbon group, or an alkylcarbonyloxy group, and R12 to R16 are independently a hydrogen atom or a hydrocarbon group.

US Pat. No. 10,654,885

PROCESS FOR THE PREPARATION OF 9 BETA,10 ALPHA-PROGESTERONE (RETROPROGESTERONE)

INDUSTRIALE CHIMCA S.R.L....

1. Process for the synthesis of retroprogesterone, comprising the following steps:a) reaction of compound (7), (3S,3aS,5aR,6R,9aR,9bS)-3-((S)-1-hydroxyethyl)-3a,6-dimethyldodecahydro-7H-cyclopenta[a]naphthalen-7-one, with acrylonitrile to yield compound (6), 3-((3S,3aS,5aR,6S,9aS,9bS)-3-((S)-1-hydroxyethyl)-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl)propanenitrile:

b) reaction of compound (6) with a strong base to yield compound (5), 3-((3S,3aS,5aR,6S,9aS,9bS)-3-((S)-1-hydroxyethyl)-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl)propanoic acid:

c) reaction of compound (5) with acetic anhydride, Ac2O, to yield compound (4), (S)-1-((4aS,4bR,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydroindeno[5,4-f]chromen-7-yl)ethyl acetate:

d) reaction of compound (4) with a C1 organometallic reagent to yield compound (3), (S)-1-((3S,3aS,5aR,6S,9aS,9bS)-3a,6-dimethyl-7-oxo-6-(3-oxobutyl)dodecahydro-1H-cyclopenta[a]naphthalen-3-yl)ethyl acetate:

wherein by “C1 organometallic reagent” is meant an organometallic compound in which the organic moiety comprises only one carbon atom;
e) reaction of compound (3) with a strong base to yield compound (2), (8S,9R,10S,13S,14S,17S)-17-((S)-1-hydroxyethyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one:

f) oxidation of intermediate (2) to obtain retroprogesterone:

US Pat. No. 10,654,884

PURINE DERIVATIVES AS CD73 INHIBITORS FOR THE TREATMENT OF CANCER

Boehringer Ingelheim Inte...

1. A compound of Formula Ia:or a pharmaceutically acceptable salt thereof, wherein:Hy is selected from:

A is O, S, NRf, or CH2;
W is O or S;
X is C1-4 haloalkyl, —C(O)OR3, —C(O)NR4R5, —CH2OR3, —S(O)2R6, —P(O)(OR7)(OR8), or a 5-6 membered heteroaryl group optionally substituted with 1, 2, or 3 substituents independently selected from halo, CN, OH, C1-4 alkyl, C1-4 alkoxy, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, C(O)(C1-4 alkyl), C(O)NH2, C(O)NH(C1-4 alkyl), C(O) N(C1-4 alkyl)2, C(O)OH, or C(O)O(C1-4 alkyl);
Y is H, Cy1, C1-4 alkyl, or —C(O)OR9, wherein said C1-4 alkyl is optionally substituted by 1, 2, or 3 substituents independently selected from Cy1, halo, C1-4 haloalkyl, 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)ORa1, NRc1C(O)NRc1Rd1, NRc1S(O)Rb1, NRc1S(O)2Rb1, NRc1S(O)2NRc1Rd1, S(O)Rb1, S(O)NRc1Rd1, S(O)2Rb1, or S(O)2NRc1Rd1;
Z is —C(O)OR10 or —P(O)(OR11)(OR12);
R1 and R2 are both H;
R3 is H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl, C3-10 cycloalkyl-C1-4 alkyl, (5-10 membered heteroaryl)-C1-4 alkyl, and (4-10 membered heterocycloalkyl)-C1-4 alkyl, wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl, C3-10 cycloalkyl-C1-4 alkyl, (5-10 membered heteroaryl)-C1-4 alkyl, and (4-10 membered heterocycloalkyl)-C1-4 alkyl are each optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C1-4 alkyl, C1-4 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)ORa2, NRc2C(O)NRc2Rd2, NRc2S(O)Rb2, NRc2S(O)2Rb2 NRc2S(O)2NRc2Rd2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2, or S(O)2NRc2Rd2;
R4 and R5 are each independently selected from H, —NRARB, —ORC, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl, C3-10 cycloalkyl-C1-4 alkyl, (5-10 membered heteroaryl)-C1-4 alkyl, or (4-10 membered heterocycloalkyl)-C1-4 alkyl, wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl, C3-10 cycloalkyl-C1-4 alkyl, (5-10 membered heteroaryl)-C1-4 alkyl, or (4-10 membered heterocycloalkyl)-C1-4 alkyl are each optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, CN, NO2, ORa3, SRa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)OR, NRc3C(O)NRc3Rd3, NRc3S(O)Rb3, NRc3S(O)2Rb3, NRc3S(O)2NRc3Rd3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3, or S(O)2NRc3Rd3;
R6 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl, C3-10 cycloalkyl-C1-4 alkyl, (5-10 membered heteroaryl)-C1-4 alkyl, or (4-10 membered heterocycloalkyl)-C1-4 alkyl;
R7 and R8 are each independently selected from H or C1-6 alkyl optionally substituted by 1, 2, or 3 substituents independently selected from halo, CN, OR4, SR4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4C(O)Rb4, NRc4C(O)ORa4, NRc4C(O)NRc4Rd4, NRc4S(O)Rb4, NRc4S(O)2Rb4, NRc4S(O)2NRc4Rd4, S(O)Rb4, S(O)NRc4Rd4, S(O)2Rb4, or S(O)2NRc4Rd4;
R9 is H or C1-4 alkyl;
R10 is H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl, C3-10 cycloalkyl-C1-4 alkyl, (5-10 membered heteroaryl)-C1-4 alkyl, or (4-10 membered heterocycloalkyl)-C1-4 alkyl, wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl, C3-10 cycloalkyl-C1-4 alkyl, (5-10 membered heteroaryl)-C1-4 alkyl, or (4-10 membered heterocycloalkyl)-C1-4 alkyl are each optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, 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)ORa5, NRc5C(O)NRc5Rd5, NRc5S(O)Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, or S(O)2NRc5Rd5;
R11 and R12 are each independently selected from H or C1-6 alkyl optionally substituted by 1, 2, or 3 substituents independently selected from halo, CN, ORa6, SRa6, C(O)Rb6, C(O)NRc6Rd6, C(O)ORa6, OC(O)Rb6, OC(O)NRc6Rd6, NRc6Rd6, NRc6C(O)Rb6, NRc6C(O)ORa6, NRc6C(O)NRc6Rd6, NRc6S(O)Rb6, NRc6S(O)2Rb6, NRc6S(O)2NRc6Rd6, S(O)Rb6, S(O)NRc6Rd6, S(O)2Rb6, or S(O)2NRc6Rd6;
RA is H or C1-6 alkyl;
RB is C1-6 alkyl or —C(O)(C1-6 alkyl);
RC is H or C1-6 alkyl;
Ra is Cy2, H, halo, C1-4 alkyl, NRc7Rd7, or NRc7C(O)Rb7, wherein said C1-4 alkyl is optionally substituted by Cy2;
Rb is H or halo;
Rc is Cy2, halo, C1-4 alkyl, C1-4 haloalkyl, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)ORa7, NRc7C(O)NRc7Rd7, NRc7S(O)Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, or S(O)2NRc7Rd7, wherein said C1-4 alkyl is optionally substituted by 1, 2, or 3 substituents independently selected from Cy2, H, halo, C1-4 haloalkyl, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)ORa7, NRc7C(O)NRc7Rd7 NRc7S(O)Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, or S(O)2NRc7Rd7;
Rd is halo or CN;
Re selected from H, halo, or C1-4 alkyl;
Rf is H, C1-4 alkyl, or —C(O)(C1-4 alkyl);
each Cy1 and Cy2 are independently selected from C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, or 4-10 membered heterocycloalkyl, each of which is substituted with 1, 2, 3, or 4 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, NO2, ORa8, SRa8, C(O)Rb8, C(O)NRc8Rd8, C(O)ORa8, OC(O)Rb8, OC(O)NRc8Rd8, NRc8Rd8, NRc8C(O)Rb8, NRc8C(O)ORa8, NRc8C(O)NRc8Rd8, NRc8S(O)Rb8, NRc8S(O)2Rb8, NRc8S(O)2NRc8Rd8, S(O)Rb8, S(O)NRc8Rd8, S(O)2Rb8, or S(O)2NRc8Rd8;
each Ra1, Rb1, Rc1, Rd1, Ra2, Rb2, Rc2, Rd2, Ra3, Rb3, Rc3, Rd3, Ra4, Rb4, Rc4, Rd4, Ra5, Rb5, Rc5, Rd5, Ra6, Rb6, Rc6, Rd6, Ra7, Rb7, Rc7, Rd7, Ra8, Rb8, Rc8, and Rd8 is independently selected from H, C1-6 alkyl, C1-4 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl-, C3-10 cycloalkyl-C1-4 alkyl-, (5-10 membered heteroaryl)-C1-4 alkyl-, or (4-10 membered heterocycloalkyl)-C1-4 alkyl-, wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, 4-10 membered heterocycloalkyl, C6-10 aryl-C1-4 alkyl-, C3-10 cycloalkyl-C1-4 alkyl-, (5-10 membered heteroaryl)-C1-4 alkyl-, and (4-10 membered heterocycloalkyl)-C1-4 alkyl- is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc1 and Rd1 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc2 and Rd2 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc3 and Rd3 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc4 and Rd4 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc5 and Rd5 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc6 and Rd6 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc7 and Rd7 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9;
or any Rc8 and Rd8 together with the N atom to which they are attached form a 4-, 5-, 6-, or 7-membered heterocycloalkyl group optionally substituted with 1, 2, or 3 substituents independently selected from C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa9, SRa9, C(O)Rb9, C(O)NRc9Rd9, C(O)ORa9, OC(O)Rb9, OC(O)NRc9Rd9, NRc9Rd9, NRc9C(O)Rb9, NRc9C(O)NRc9Rd9, NRc9C(O)ORa9, S(O)Rb9, S(O)NRc9Rd9, S(O)2Rb9, NRc9S(O)2Rb9, NRc9S(O)2NRc9Rd9, or S(O)2NRc9Rd9; and
each Ra9, Rb9, Rc9, and Rd9 is independently selected from H, C1-4 alkyl, C1-4 haloalkyl, C2-4 alkenyl, and C2-4 alkynyl, wherein said C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl, is optionally substituted with 1, 2, or 3 substituents independently selected from OH, CN, amino, halo, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, C1-4 alkylamino, di(C1-4 alkyl)amino, C1-4 haloalkyl, or C1-4 haloalkoxy.

US Pat. No. 10,654,883

INORGANIC SALTS OF NICOTINIC ACID MONONUCLEOTIDE AS ANTI-AGING AGENTS

Jumpstart Fertility Pty L...

1. A salt selected from the group consisting of:

US Pat. No. 10,654,882

NICOTINAMIDE MONONUCLEOTIDE DERIVATIVE AND SALT THEREOF, METHOD FOR PRODUCING SAME, TOPICAL SKIN PREPARATION, COSMETIC AND FOOD ADDITIVE

SHOWA DENKO K.K., Tokyo ...

1. A nicotinamide mononucleotide derivative, or salt thereof, which is a compound represented by general formula (1):
wherein, R1 and R2 respectively and independently represent a hydrogen atom or an acyl group having 3 to 30 carbon atoms, wherein the hydrocarbon group bound to the carbonyl carbon of the acyl group is a linear or branched, saturated or unsaturated hydrocarbon group, and at least one of R1 and R2 is an acyl group.

US Pat. No. 10,654,880

METHODS FOR PREPARATION OF GLYCOSPHINGOLIPIDS AND USES THEREOF

1. A method for preparing a chiral compound comprising an R-form or S-form of a compound of formula (5):
or a pharmaceutically acceptable salt thereof, via alpha-glycosylation, the method comprising reacting a compound of formula (6):

or pharmaceutically acceptable salt thereof,
wherein PG is a hydroxyl protecting group and LG is the following:

with a compound of formula (7):

or pharmaceutically acceptable salt thereof,
in the presence of Lewis acid, to obtain a compound of formula (5), or pharmaceutically acceptable salt thereof.

US Pat. No. 10,654,879

NICKEL-BASED CATALYSTS FOR C=O REDUCTION AND OXYGEN EVOLUTION

UNIVERSITY OF SOUTHERN CA...

1. A compound having formula I:
wherein:
M is a transition metal;
X1, X2 are each independently a counterion; and
R1, R2, R3 are each independently H, C1-6 alkyl, C6-15 aryl, or C6-15 heteroaryl.

US Pat. No. 10,654,878

COMPOUNDS OF PHOSPHINANES AND AZAPHOSPHINANES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

LES LABORATOIRES SERVIER,...

1. A method of treating or preventing Alzheimer's disease in a subject in need thereof, comprising administration of an effective amount of a compound of formula (I):
wherein:
Ak1 represents a C1-C6-alkyl chain;
X represents —(CH2)m—, —CH(R)—, —N(R)—, —CH2—N(R)—, —N(R)—CH2— or —CH2—N(R)—CH2—;
m represents 0 or an integer from 1 to 4;
R represents a hydrogen atom, C1-C6-alkyl, -Ak2-Ar1, -Ak2-Ar1-Ar2, -Ak2-Ar1—O—Ar2, -Ak2-cycloalkyl or -Ak2-OH;
Ak2 represents a linear or branched C1-C6-alkyl chain;
Ar1 and Ar2, which may be identical or different, each represent an aryl or heteroaryl group;
R1 and R2 each represent a hydrogen atom when X represents —(CH2)m—, —CH(R)—, —N(R)—, —CH2—N(R)— or —N(R)—CH2—,
or together form a bond when X represents —CH2—N(R)—CH2—;
R3 represents NH2, Cy-NH2, Cy-Ak3-NH2 or piperidin-4-yl;
Cy represents cycloalkyl, aryl or heteroaryl;
Ak3 represents a C1-C3-alkyl chain;
R4 and R5, which may be identical or different, each represent a hydrogen atom or a fluorine atom;
its optical isomers, or addition salts thereof with a pharmaceutically acceptable acid, wherein the compound of formula (I) is administered alone or in combination with one or more inert, non-toxic, pharmaceutically acceptable excipients or carriers.

US Pat. No. 10,654,877

DIOXOLANE ANALOGUES OF URIDINE FOR THE TREATMENT OF CANCER

MEDIVIR AB, Stockholm (S...

1. A method for the treatment of liver cancer, comprising the oral administration to a warm blooded animal of a therapeutically effective amount of a compound of the formula Ia:
wherein:
R1 is NH2;
R2 is H;
R13 is phenyl, optionally substituted with 1, 2 or 3 R22;
R15 is methyl;
R16 is 2-pentyl;
each R22 is independently selected from halo, C1-C6alkyl, C2-C6alkenyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, phenyl, hydroxyC1-C6alkyl, C3-C6cycloalkyl, C1-C6alkylcarbonyl, C3-C6cycloalkylcarbonyl, carboxyC1-C6alkyl, hydroxy, amino CN, and NO2, or any two R22 groups attached to adjacent ring carbon atoms can combine to form —O—(CR23R23?)1-6—O—;
R23 and R23? are independently H or C1-C3alkyl;
or a pharmaceutically acceptable salt and/or solvate thereof.

US Pat. No. 10,654,876

TH-302 SOLID FORMS AND METHODS RELATED THERETO

Molecular Templates, Inc....

1. A process for preparing a compound of Formula V:
comprising
reacting a compound of Formula II with a reducing agent in a base followed by adding an acid to provide a compound of Formula III:

and
reacting a compound of Formula III with a trisubstituted phosphine, an oxidizing agent and a phosphorus containing compound having the formula IV:

to provide a compound of Formula V.

US Pat. No. 10,654,875

CELL-PENETRATING, GUANIDINIUM-RICH OLIGOPHOSPHOTRIESTERS FOR DRUG AND PROBE DELIVERY

The Board of Trustees of ...

1. A transporter compound of the formula:wherein:Z1 is a cargo moiety, a reactive functional group or a protected functional group;
L1 is an optional linker;
X is O, S or NH;
L2 is a linker;
Z2 is an guanidine group or a protected guanidine group;
R3 is H, an alkyl, a substituted alkyl, an acyl, a substituted acyl, an aryl, a substituted aryl, a heteroaryl or a substituted heteroaryl;
R1 and R2 are independently H, an alkyl or a substituted alkyl;each p is independently 1, 2 or 3; andm is between 2 and 50.

US Pat. No. 10,654,873

CYTOTOXIC AGENTS AND CONJUGATES THEREOF

POLYTHERICS LIMITED, Cam...

1. A compound of the general formula I or a salt thereof:
in which R represents a group —Y—OH, —Y—O—Rx, —Y—SH, —Y—S—Rx, —Y—S(O)2NH—Rx, —Y—NHS(O)2—Rx, —Y—C(O)H, —Y—CO2H, —Y—C(O)—Rx, —Y—C(O)NH—Rx, —Y—NHC(O)—Rx, —Y—NHRy, —Y—NRxRy, —Y—NRy—NHRz, —Y—CRy?NOH, —Y—C(NH2)?NOH, —Y—C(O)NH2, —Y—C(O)NH—NH2, or —Y—S(O)2NH2, in which either Y is not present or Y represents a C1-6alkylene, C2-6alkenylene, C2-6alkynylene or C1-6alkyleneoxy group which may be interrupted by an oxygen atom and/or which may optionally be substituted by —OH or —OC1-4alkyl, or Y represents a phenylene or C5-10heteroarylene group;
Rx represents a C1-6alkyl, C2-6alkenyl, C2-6alkynyl, phenyl, C5-10heteroaryl or benzyl group which is substituted by —OH, —SH, —NHRy, or —CO2H;
each of Ry and Rz independently represents a hydrogen atom, a C1-4alkyl group, phenyl, C5-10heteroaryl or a benzyl group;
X represents OH, OC1-4alkyl, SH, S1-4alkyl, or CN;
Ra represents a hydrogen atom or a C1-4alkyl group;
Rb represents hydrogen, OH, C1-4alkoxy or C1-4alkylC(O)O—;
Rc represents hydrogen, OH, C1-4alkoxy or C1-4alkylC(O)O—;
Rd represents a C1-4alkyl group;
each Re independently represents a halogen atom, an optionally substituted C1-6alkyl, C2-6alkenyl, C2-6alkynyl or C1-6alkoxy group each of which may be optionally interrupted by an oxygen atom, an optionally substituted phenyl or C5-10heteroaryl group, —OH, —CO2Rv, —C(O)NRvRw, —NRyC(O)Rw, NRvRw, —S(O)—Rv, S(O)2—Rv, —S(O)2NRvRw, a —CN group, or a —NO2 group; Rv and Rw are each independently selected from the group consisting of hydrogen, phenyl, benzyl, and an optionally substituted C1-6alkyl, C2-6alkenyl or C2-6alkynyl group each of which may be optionally interrupted by an oxygen atom; and n is 0, 1, 2, 3 or 4;
Rf represents a hydrogen atom or a C1-4alkyl group; and
Rg represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, or heteroaryl group.

US Pat. No. 10,654,871

PROCESS FOR PREPARING (3S,11AR)-N-(2,4-DIFLUOROBENZYL)-6-HYDROXY-3-METHYL-5,7-DIOXO-2,3,5,7,11,11A-HEXAHYDROOXAZOLO[3,2-A]PYRIDO[1,2-D]PYRAZINE-8-CARBOXAMIDE

ViiV Healthcare Company, ...

1. A process for the preparation of a compound of formula VIII:comprising:contacting a compound of formula VII:

with a Lewis acid selected from the group consisting of lithium chloride, lithium bromide, lithium iodide, lithium sulfide, magnesium chloride, magnesium bromide, magnesium iodide and magnesium sulfide, to form the compound of formula VIII above.

US Pat. No. 10,654,870

PROCESS FOR PREPARING SUBSTITUTED PYRIDINONES AS INTERMEDIATES IN THE PREPARATION OF POLYCYCLIC CARBAMOYLPYRIDONE DERIVATIVES

ViiV Healthcare Company, ...

1. A process for the preparation of a compound of formula IV:wherein:R is alkyl, aryl or benzyl;comprising:hydrolyzing a compound of formula III:wherein:R is alkyl, aryl or benzyl;in the presence of lithium hydroxide, to form the compound of formula IV above.

US Pat. No. 10,654,869

BACTERIAL TOPOISOMERASE I INHIBITORS WITH ANTIBACTERIAL ACTIVITY

THE FLORIDA INTERNATIONAL...

1. A compound having the following structure:
R1 being selected from —NH2, —NO2, —NHMe, —Ac, —CN, —NHAc, —NHCH2CH2NH2, —CF3, alkyl, substituted alkyl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocycloalkyl, and substituted heterocycloalkyl;
R2 being selected from H, alkyl, and substituted alkyl;
R3 being F; and
R4 being selected from fluorine, chloride, bromine, and iodine.

US Pat. No. 10,654,868

DIHYDROPYRAZOLE AZEPINE COMPOUND SERVING AS AKT INHIBITOR

HARBIN ZHENBAO PHARMACEUT...

1. A compound of formula (I) or a pharmaceutically acceptable salt thereof,
wherein,
R1 is H, halogen, CN, CH3, CH2CH3, CF3, cyclopropyl, phenyl or pyridyl;
X is C or N;
Y is S, O, N or N(CH3);
Z is C(R21)(R22), C(?O), O or S;
W is C(R61)(R62) or C(?O);
is a five-membered heteroaryl;each of R21, R22, R61 and R62 is independently H, halogen, hydroxyl, amino or methoxy;
m is 0, 1 or 2;
R3 is phenyl or pyridyl, which is optionally substituted by 1, 2 or 3 R;
each of R4 and R5 is independently H or CH3;
R is F, Cl, CN or CF3.

US Pat. No. 10,654,867

HETEROARYL ESTROGEN RECEPTOR MODULATORS AND USES THEREOF

Genentech, Inc., South S...

1. A compound having the structure:
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,654,866

SELECTIVE ESTROGEN RECEPTOR DEGRADERS

Eli Lilly and Company, I...

1. A compound of the formula:
wherein either R1 or R2 is independently selected from Cl, F, —CF3, or —CH3, and the other is hydrogen,
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,654,865

ENANTIOSELECTIVE SYNTHESES OF HETEROYOHIMBINE NATURAL PRODUCT INTERMEDIATES

NORTHWESTERN UNIVERSITY, ...

1. A method of preparing a cis-bicyclic dihydropyran compound, said method comprising:providing a hydroxy ester compound of a formula

dehydration and reprotection of said hydroxy ester compound to provide an alkene compound of a formula
andhydroboration of said alkene compound to promote formation of a lactone compound of a formula
andacylation of said lactone compound and subsequent treatment with an acid catalyst to provide a cis-bicyclic dihydropyran compound of a formula

US Pat. No. 10,654,864

MODIFIED CYTOTOXINS AND THEIR THERAPEUTIC USE

The Regents of the Univer...

1. A pharmaceutical composition comprising:a first compound, which is a compound of formula (I)
A1-X1X—2-A2  (I)wherein:A2 is a cytotoxic drug moiety, which has a molecular weight of no more than 1600 Da, wherein the cytotoxic drug moiety comprises an oxygen atom or an NH group through which it connects to —X2—X1-A1; and
—X2—X1-A1 is selected from the group consisting of: —C(?O)—(CH2)n1—C(?O)—OH; —C(?O)—(CH2)n1—C(?O)—OCH3; —C(?O)—(C1-6 alkylene)-C(?O)—O—(CH2)n2—C(?O)—OH; —C(?O)—(C1-6alkylene)-NH—C(?O)—(CH2)n1—C(?O)—OH; and —C(?O)—(C1-6 alkylene)-C(?O)—O—[(CH2)2—O-]n3(CH2)n2—C(?O)—OH; wherein n1 is an integer 12 to 24, n2 is an integer from 13 to 25, and n3 is an integer from 1 to 25; and
a protein, wherein the protein is human serum albumin or a protein whose sequence is at least 80% equivalent to that of human serum albumin.

US Pat. No. 10,654,862

METHODS FOR THE CHEMICAL SYNTHESIS OF PYRROLE-LINKED BIVALENT COMPOUNDS, AND COMPOSITIONS THEREOF

AVEKSHAN, LLC., Alachua,...

1. A process for a chemical synthesis of norBNI or a related pyrrole-linked bivalent compound having the structure of Formula I(C):
or a salt thereof, wherein:
each of X1 and X2 is O, N, or S, and each of R1 to R11 is independently selected from hydrogen or a substituent
the process comprising reacting naltrexone or related compound for producing the bivalent compound of Formula I(C)
with a hydrazine reagent in a reaction solvent under reaction conditions sufficient to produce the compound of Formula I(C) or salt thereof without exchanging the reaction solvent, and wherein the reaction conditions comprise the presense of an alkylsulfonic acid as a catalyst.

US Pat. No. 10,654,861

FUSED PENTACYCLIC IMIDAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

UCB Biopharma SRL, Bruss...

1. A compound of formula (I) or an N-oxide thereof, or a pharmaceutically acceptable salt thereof:whereinA represents N or C—R6;
B represents N or C—R7;
D represents N or C—R8;
Z represents methylene;
E represents a fused heteroaromatic ring system selected from the groups of formula (Ea), (Eb) and (Ec):
wherein the asterisks (*) represent the site of attachment of E to the remainder of the molecule;R1 represents hydrogen, halogen, cyano, trifluoromethyl, trifluoromethoxy, —ORa, —SRa, —SORa, —SO2Ra, —NRbRc, —NRcCORd, —NRcCO2Rd, —NHCONRbRc, —NRbSO2Re, —CORd, —CO2Rd, —CONRbRc, —SO2NRbRc, or —S(O)(N—Rb)Re; or R1 represents C1-6 alkyl, C3-7 cycloalkyl, C4-7 cycloalkenyl, aryl, aryl(C1-6)alkyl, C3-7 heterocycloalkyl, C3-7 heterocycloalkenyl, heteroaryl, heteroaryl(C1-6)alkyl, (C3-7)heterocycloalkyl(C1-6)alkyl-aryl-, (C3-7)heterocycloalkenyl-aryl-, (C3-7)cycloalkyl-heteroaryl-, (C3-7)cycloalkyl-(C1-6)alkyl-heteroaryl-, (C4-7)cycloalkenyl-heteroaryl-, (C4-9)bicycloalkyl-heteroaryl-, (C3-7)heterocycloalkyl-heteroaryl-, (C3-7)heterocycloalkyl(C1-6)alkyl-heteroaryl-, (C3-7)heterocycloalkenyl-heteroaryl-, (C4-9)heterobicycloalkyl-heteroaryl- or (C4-9)spiroheterocycloalkyl-heteroaryl-, any of which groups may be optionally substituted by one, two or three substituents independently selected from halogen, halo(C1-6)alkyl, cyano, cyano(C1-6)alkyl, nitro(C1-6)alkyl, C1-6 alkyl, phosphate(C1-6)alkyl, (C1-6)alkylphosphate(C1-6)alkyl, phosphate(C1-6)alkoxy(C1-6)alkyl, sulphate(C1-6)alkyl, difluoromethyl, trifluoromethyl, trifluoroethyl, C2-6 alkenyl, hydroxy, hydroxy(C1-6)alkyl, C1-6 6 alkoxy, (C1-6)alkoxy(C1-6)-alkyl, trifluoroethoxy, carboxy(C3-7)cycloalkyloxy, C1-6 alkylthio, C1-6 alkylsulphonyl,(C1-6)alkylsulphonyl(C1-6)alkyl, oxo, amino, amino(C1-6)alkyl, C1-6 alkylamino, di(C1-6)-alkylamino, di(C1-6)alkylamino(C1-6)alkyl, (C1-6)alkoxy(C1-6)alkylamino, N—[(C1-6)alkyl]-N-[hydroxy(C1-6)alkyl]amino, (C2-6)alkylcarbonylamino(C1-6)alkyl, (C2-6)alkoxycarbonyl-amino(C1-6)alkyl, C1-6 alkylsulphinylamino, C1-6 alkylsulphonylamino, N—[(C1-6)alkyl]-N—[(C1-6)alkylsulphonyl]amino, bis[(C1-6)alkylsulphonyl]amino, (C1-6)alkylsulphonylamino-(C1-6)alkyl, N—[(C1-6)alkyl]-N-[carboxy(C1-6)alkyl]amino, carboxy(C3-7)cycloalkylamino, carboxy(C3-7)cycloalkyl(C1-6)alkylamino, imino, formyl, C2-6 alkylcarbonyl, (C2-6)alkyl-carbonyloxy(C1-6)alkyl, carboxy, carboxy(C1-6)alkyl, C2-6 alkoxycarbonyl, C2-6 alkoxy-carbonyl(C1-6)alkyl, morpholinyl(C1-6)alkoxycarbonyl, C2-6 alkoxycarbonylmethylidenyl, aminocarbonyl, aminosulphonyl, (C1-6)alkylsulphoximinyl and [(C1-6)alkyl][N—(C1-6)-alkyl]sulphoximinyl;R2 represents hydrogen, halogen, cyano, nitro, hydroxy, trifluoromethyl, trifluoromethoxy or —ORa; or R2 represents C1-6 alkyl or heteroaryl, either of which groups may be optionally substituted by one, two or three substituents independently selected from hydroxy(C1-6)alkyl and C2-6 alkoxycarbonyl;
R3 and R4 independently represent hydrogen, halogen or trifluoromethyl; or C1-6 alkyl;
R5 represents hydrogen, halogen, hydroxy, cyano, trifluoromethyl, difluoromethoxy, trifluoromethoxy, —ORa or C1-6 alkylsulphonyl; or R5 represents C1-6 alkyl;
R6, R7 and R8 independently represent hydrogen, halogen, trifluoromethyl, C1-6 alkyl or C1-6 alkoxy;
R12 represents hydrogen or C1-6 alkyl;
Ra represents C1-6 alkyl, C3-7 cycloalkyl, aryl, aryl(C1-6)alkyl, C3-7 heterocycloalkyl, heteroaryl or heteroaryl(C1-6)alkyl, any of which groups may be optionally substituted by one or more substituents selected from C1-6 alkoxy and oxo;
Rb represents hydrogen or trifluoromethyl; or C1-6 alkyl, C3-7 cycloalkyl, C3-7 cycloalkyl(C1-6)alkyl, aryl, aryl(C1-6)alkyl, C3-7 heterocycloalkyl, C3-7 heterocycloalkyl(C1-6)alkyl, heteroaryl or heteroaryl(C1-6)alkyl, any of which groups may be optionally substituted by one or more substituents selected from C1-6 alkoxy, C1-6 alkylthio, C1-6 alkylsulphinyl, C1-6 alkylsulphonyl, hydroxy, cyano, C2-6 alkoxycarbonyl, 6)alkylamino and C2-6 alkoxycarbonylamino;
Rc represents hydrogen or trifluoromethyl; or C1-6 alkyl, C3-7 cycloalkyl, C3-7 cycloalkyl(C1-6)alkyl, aryl, aryl(C1-6)alkyl, C3-7 heterocycloalkyl, C3-7 heterocycloalkyl(C1-6)alkyl, heteroaryl or heteroaryl(C1-6)alkyl, any of which groups may be optionally substituted by one or more substituents selected from C2-6 alkylcarbonyl and C2-6 alkoxycarbonyl; or
Rb and Rc, when taken together with the nitrogen atom to which they are both attached, represent a heterocyclic moiety selected from azetidin-1-yl, pyrrolidin-1-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, piperazin-1-yl, homopiperidin-1-yl, homomorpholin-4-yl, homopiperazin-1-yl, (imino)(oxo)thiazinan-4-yl, (oxo)thiazinan-4-yl and (dioxo)-thiazinan-4-yl, any of which groups may be optionally substituted by one or more substituents selected from C1-6 alkyl, C1-6 alkylsulphonyl, hydroxy, hydroxy(C1-6)alkyl, amino(C1-6)alkyl, cyano, oxo, C2-6 alkylcarbonyl, carboxy, C2-6 alkoxycarbonyl, amino, C2-6 alkylcarbonyl-amino, C2-6 alkylcarbonylamino(C1-6)alkyl, C2-6 alkoxycarbonylamino, C1-6 alkyl-sulphonylamino and aminocarbonyl;
Rd represents hydrogen; or Rd represents C1-6 alkyl, C3-7 cycloalkyl, aryl, C3-7 heterocycloalkyl or heteroaryl, any of which groups may be optionally substituted by one or more substituents selected from halogen, C1-6 alkyl, C1-6 alkoxy, oxo, C2-6 alkylcarbonyloxy and di(C1-6)alkylamino;
Re represents C1-6 alkyl, aryl or heteroaryl, any of which groups may be optionally substituted by C1-6 alkyl; and
Rf and Rg independently represent hydrogen or C1-6 alkyl.

US Pat. No. 10,654,860

TRICYCLIC RHO KINASE INHIBITORS

Bristol-Myers Squibb Comp...

1. A compound according to formula (I):
or a stereoisomer, tautomer, pharmaceutically acceptable salt thereof, wherein
X is independently selected from —CR3R4—, —O—, and NR5a;
Y is independently selected from —CR2 and N;
Z is independently selected from —NR5C(O)NR5(CR6R7)q—R8, —NR5C(O)(CR6R7)q—R8, —C(O)NR5(CR6R7)q—R8,

--- is an optional bond;
L is independently selected from —(CR6R7)q—, —NR5a(CR6R7)q—, and —O(CR6R7)q—;
R1 is independently selected from H, F, Cl, Br, CN, NRaRa, —OC1-4 alkyl substituted with 0-3 Re, C1-4 alkyl substituted with 0-3 Re, and —(CH2)rORb;
R2 is independently selected from H, F, Cl, Br, CN, NRaRa, —OC1-4 alkyl substituted with 0-3 Re, C1-4 alkyl substituted with 0-3 Re, —(CH2)rORb;
R3 and R4 are independently selected from H and C1-4 alkyl substituted with 0-3 Re;
R5 is independently selected from H and C1-4 alkyl;
R5a is independently selected from H and C1-4 alkyl;
R6 and R7 are independently selected from H, C1-4alkyl substituted with 0-4 Re, —(CH2)rORb, —(CH2)rS(O)pRc, —(CH2)rC(?O)Rb, —(CH2)rNRaRa, —(CH2)rC(?O)(CH2)rNRaRa, —(CH2)rNRaC(?O)Rb, —(CH2)rNRaC(?O)ORb, —(CH2)rOC(?O)NRaRa, —(CH2)rNRaC(?O)NRaRa, —(CH2)rC(?O)ORb, —(CH2)rS(O)pNRaRa, —(CH2)rNRaS(O)pNRaRa, —(CH2)rNRaS(O)pRc, (CH2)r—C3-6 carbocyclyl substituted with 0-3 Re, and —(CH2)r-heterocyclyl substituted with 0-3 Re;
is independently selected from carbocyclyl and heterocyclyl;R8 is selected from C3-10carbocyclyl and heterocyclyl, each substituted with 1-5 R9;
R9 is independently selected from H, F, Cl, Br, C1-4alkyl substituted with 0-5 Re, C2-4alkenyl substituted with 0-5 Re, C2-4alkynyl substituted with 0-5 Re, ?O, nitro, —(CHRd)rS(O)pRc, —(CHRd)rS(O)pNRaRa, —(CHRd)rNRaS(O)pRc, —(CHRd)rORb, —(CHRd)rCN, —(CHRd)rNRaRa, —(CHRd)rNRaC(?O)Rb, —(CHRd)rNRaC(?O)NRaRa, —(CHRd)rC(?O)ORb, —(CHRd)rC(?O)Rb, —(CHRd)r OC(?O)Rb, —(CHRd)rC(?O)NRaRa, —(CHRd)r-cycloalkyl, —(CHRd)r-heterocyclyl, —(CHRd)r-aryl, and —(CHRd)r-heteroaryl, wherein said alkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is substituted with 0-4 Re;
alternatively, two adjacent R9 groups are combined to form a carbocyclic or heterocyclic ring comprising carbon atoms and 1-3 hetero atoms selected from N, O, and S(O)p, wherein the carbocyclic and heterocyclic rings are substituted with 0-4 Re;
R10 is independently selected from H, ?O, C1-4alkyl substituted with 0-4 Re, —(CH2)rORb, C(?O)Rb, and —C(?O)ORb;
Ra, at each occurrence, is independently selected from H, C1-6 alkyl substituted with 0-5 Re, C2-6alkenyl substituted with 0-5 Re, C2-6alkynyl substituted with 0-5 Re, —(CH2)r—C3-10carbocyclyl substituted with 0-5 Re, and —(CH2)r-heterocyclyl substituted with 0-5 Re; or Ra and Ra together with the nitrogen atom to which they are both attached form a heterocyclic ring substituted with 0-5 Re;
Rb, at each occurrence, is independently selected from H, C1-6 alkyl substituted with 0-5 Re, C2-6 alkenyl substituted with 0-5 Re, C2-6 alkynyl substituted with 0-5 Re, —(CH2)r—C3-10carbocyclyl substituted with 0-5 Re, and —(CH2)r-heterocyclyl substituted with 0-5 Re;
Rc, at each occurrence, is independently selected from C1-6 alkyl substituted with 0-5 Re, C2-6alkenyl substituted with 0-5 Re, C2-6alkynyl substituted with 0-5 Re, C3-6carbocyclyl, and heterocyclyl;
Rd, at each occurrence, is independently selected from H and C1-4alkyl substituted with 0-5 Re;
Re, at each occurrence, is independently selected from C1-6 alkyl (optionally substituted with F, Cl, and Br, OH), C2-6 alkenyl, C2-6 alkynyl, —(CH2)r—C3-10 carbocyclyl, —(CH2)r-heterocyclyl, F, Cl, Br, CN, NO2, ?O, CO2H, CO2C1-6 alkyl, —(CH2)rOC1-5 alkyl, —(CH2)rOH, —(CH2)rNRfRf, —(CH2)rNRfRfC(?O) C1-4alkyl, —C(?O)NRfRf, —C(?O)Rf, S(O)pNRfRf, —NRfRfS(O)pC1-4alkyl, and S(O)pC1-4alkyl;
Rf, at each occurrence, is independently selected from H, F, Cl, Br, C1-5alkyl, C3-6 cycloalkyl; or Rf and Rf together with the nitrogen atom to which they are both attached form a heterocyclic ring;
p, at each occurrence, is independently selected from zero, 1, and 2;
q, at each occurrence, is independently selected from zero, 1, 2, and 3; and
r, at each occurrence, is independently selected from zero, 1, 2, 3, and 4.

US Pat. No. 10,654,859

METHANESULFONATE POLYMORPH OF 5-TYPE PHOSPHODIESTERASE INHIBITOR AND PREPARATION METHOD AND APPLICATIONS THEREOF

JINAN MEILUWEI BIOTECHNOL...

1. A methanesulfonate polymorph of a 5-type phosphodiesterase inhibitor, the structure of the 5-type phosphodiesterase inhibitor being as shown in formula A:wherein the methanesulfonate polymorph of the 5-type phosphodiesterase inhibitor includes the following diffraction peaks measured at 2? reflection angles in an X-ray powder diffraction pattern: 7.1750°±0.2°, 7.6299°±0.2°, 8.8588°±0.2°, 13.2310°±0.2°, 14.3754°±0.2°, 14.8440±0.2°, 15.2941°±0.2°, 17.1838°±0.2°, 20.0314°±0.2°, 20.8507°±0.2°, 21.2839°±0.2°, 21.7890°±0.2°, 22.2594°±0.2°, 23.0373±0.2°, 25.1243°±0.2°, 25.4244°±0.2°, 26.1530°±0.2°, 28.1210°±0.2°, 30.0135°±0.2°, 31.4809°±0.2°, 32.3619°±0.2°, 37.2410°±0.2°, 37.6388°±0.2° and 40.8286°±0.2°.

US Pat. No. 10,654,858

TRICYCLIC COMPOUNDS HAVING CYTOSTATIC AND/OR CYTOTOXIC ACTIVITY AND METHODS OF USE THEREOF

Duquesne University Of Th...

1. A method of inhibiting receptor tyrosine kinase(s), dihydrofolate reductase, thymidylate synthase and/or dihydroorotate dehydrogenase activity in an animal or human in need thereof, comprising administering to said animal or human a therapeutically effective amount in unit dosage form of a compound of formula II:
wherein both B and C rings may be completely or partially saturated or unsaturated with respect to bond 4b-8a, 5-6 and 7-8; the C ring is a carbon atom containing ring that may have one of the carbon atoms at either the Q5, Q6, Q7, or Q8 position replaced with a[n] N or substituted N depending on the saturation level of the C ring, and the substitution may be all of R1, R2 and R3;
X and/or Y=NH, O, S, CH2; P=(a) NR4, except that when P=NH and X is NH then R1 is not a phenyl moiety or a phenyl moiety having a halogen substitution, (b) O, except that when P=O and X is NH then R1 is not a phenyl moiety or a phenyl moiety having a halogen substitution, (c) S, except that when P=S and X is NH then R1 is not a phenyl moiety or a phenyl moiety having a halogen substitution, or (d) CR4R5 when the C ring has an N or a substituted N depending on the saturation level of the C ring and the substitution may be all of R1, R2, and R3; wherein R4 and R5=lower alkyl, alkene, alkyne, and all of R1 and R2;
R1 is H, alkyl, a cycloalkyl having 6 or less carbons, alkene, alkyne, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkylaryl, alkylheteroaryl, substituted alkylaryl or alkylheteroaryl and R2 is H, alkyl, a cycloalkyl having 6 or less carbons, alkene, alkyne, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkylaryl, alkylheteroaryl, substituted alkylaryl or alkylheteroaryl;
Z=S, O, NR6, S—CH2, CH2—S, O—CHR6, CHR6—O, NR6—CH2, CH2—NR6, CHR6—NR7 or CR6R7, wherein R6 and/or R7=H or a lower alkyl, alkene or alkyne having 6 or less C atoms;
wherein Z may be attached to the C ring at positions Q5, Q6, Q7 or Q8 and may be attached to more than one of said positions Q5, Q6, Q7, or Q8 on the ring wherein Z may be the same or different;
wherein Z may be zero and R3 may be directly attached to the C-ring at positions Q5, Q6, Q7, and/or Q8;
R3=H, alkyl, cycloalkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkylaryl, alkylheteroaryl and substituted saturated or unsaturated alkylheteroaryl and alkylheterocyclic, alkylaryl, p-, m-, o-benzoyl-L-glutamate or 2,5-, 2,4-thienoyl-L-glutamate when the benzene and thiophene ring may or may not have additional substitutions including F, mono-, bi- and tricyclic aryl, heteroaryl or combinations thereof, ring substitutions including biphenyl, bipyridyl or a phenyl-pyridyl or a fused moiety including a quinoline or naphthyl including substituted systems including a 2-chloro,4-biphenyl and tricyclic and substituted tricyclic systems.

US Pat. No. 10,654,857

BICYCLIC COMPOUNDS AS AUTOTAXIN (ATX) AND LYSOPHOSPHATIDIC ACID (LPA) PRODUCTION INHIBITORS

Hoffman-La Roche Inc., L...

1. A Compound of formula (I):
wherein:
R1 is substituted phenyl or substituted pyridinyl, wherein substituted phenyl and substituted pyridinyl are substituted with R3, R4 and R5;
A is —N—;
W is —C(O)—, —C(O)O—, —S(O)2—, —C(O)—NR10— or —CR6R7—;
R2 is selected from the ring systems B, C, D, E, F, G, H, I, J, K, L, M, N, O, P, Q, R, S, T, U, V, X, Z, AA, AB, AC, AD, AE, AF, AG, AH, AI, AJ, AK, AL, AM, AN, AO, AP, AQ, AR, AS, AT, AU and AV;

R3 is substituted heterocycloalkoxy, substituted heterocycloalkylalkoxy, substituted heterocycloalkylamino or substituted heterocycloalkylalkylamino, wherein substituted heterocycloalkoxy, substituted heterocycloalkylalkoxy, substituted heterocycloalkylamino and substituted heterocycloalkylalkylamino are substituted with R11, R12 and R13;
R4 and R5 are independently selected from H, amino, alkylamino, dialkylamino, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, halogen and cyano;
m, n, p and q are each 1;
R6 and R7 are independently H or alkyl;
R8 is H, alkyl, haloalkyl, or cycloalkyl;
R9 is H, alkyl, halogen, haloalkyl, or alkoxy;
R10 is H or alkyl; and
R11, R12; and R13 are independently selected from H, alkyl, alkoxy, cycloalkyl, cycloalkoxy, halogen, haloalkyl, and cyano;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,654,856

METHOD FOR PREPARING PYRROLO[3,2-D]PYRIMIDINE COMPOUND, AND INTERMEDIATES THEREOF

CHIA TAI TIANQING PHARMAC...

1. A process for preparing the compound of formula I, comprising dehydroxylating the compound of formula VI to obtain the compound of formula I
wherein
R1 and R2 are independently selected from the group consisting of C1-4 alkyl, or
R1 and R2 together with the N atom attached thereto form 4-8 membered heterocycloalkyl, wherein the heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of hydroxyl, halogen, C1-4 alkyl and C1-4 alkoxy; and
wherein the dehydroxylating is performed in the presence of triethylsilane and trifluoroacetic acid.

US Pat. No. 10,654,855

PROTEIN KINASE B INHIBITORS

AstraZeneca AB, Sodertal...

1. A method of treating breast cancer, comprising: administering to a person in need thereof a therapeutically effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof:
wherein:
Y represents N;
Z1-Z2 represents a group selected from C(R6)?CH; where
R6 represents hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, difluoromethyl, trifluoromethyl or cyclopropyl;
n is 0, 1 or 2;
R1 represents C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4alkoxy, C1-4alkoxyC1-4alkyl, fluoroC1-4alkyl, aminoC1-4alkyl, hydroxyC1-4alkyl, cyano, cyanoC1-4alkyl, C3-6cycloalkyl, —(CH2)pNHCOCH3, —(CH2)pNHSO2CH3, —(CH2)pNHCONH2, —(CH2)pNHCONR2R3, —(CH2)pNR2R3, —(CH2)pSO2NH2, —(CH2)pSO2NR2R3, —(CH2)pCONH2, —(CH2)pCONR2R3 or —(CH2)p—R7; where
p is 0, 1, 2 or 3;
R2 represents hydrogen or C1-3alkyl;
R3 represents C1-3alkyl; and
R7 represents phenyl;
R7 represents a 5 or 6 membered monocyclic heteroaryl ring which comprises 1, 2 or 3 heteroatoms selected from O, N or S; or
R7 represents a monocyclic 4, 5, or 6 membered heterocyclic ring which comprises 1, 2 or 3 heteroatoms selected from O, N or S;
wherein R7 is optionally substituted by 1 or 2 substituents selected from C1-4alkyl, trifluoromethyl, C1-4alkoxy, fluoro, chloro, bromo, and cyano;
R4 represents hydrogen, fluoro, chloro, bromo, cyano or trifluoromethyl; and
R5 represents hydrogen, fluoro, chloro or bromo.

US Pat. No. 10,654,853

SPIRO-CONDENSED PYRROLIDINE DERIVATIVES AS DEUBIQUITYLATING ENZYMES (DUB) INHIBITORS

MISSION THERAPEUTICS LIMI...

1. A compound of formula I:
a tautomer thereof, or a pharmaceutically acceptable salt of said compound or tautomer, wherein:
R1a, R1b, R1c and R1d each independently represent hydrogen or C1-C6 alkyl;
R1e and R1f each independently represent hydrogen or C1-C6 alkyl;
ring A is a 9, 10 or 11-membered fused bicyclic heterocyclyl ring, which in addition to the amide nitrogen optionally comprises 1, 2 or 3 heteroatoms each independently selected from N, O and S; wherein the ring fused to the amide-containing ring is aromatic; and which may be optionally substituted with one -Q1-(R2)n, wherein n is 1; and optionally one, two or three -Q1-(R2)n, wherein n is 0; wherein each -Q1-(R2)n, is the same or different;
when n is 0, Q1 represents halogen, cyano, oxo, hydroxyl, —NR3R4, —CONR3R4, —NR3COR4, —NR3CONR4R4a, —COR3, —C(O)OR3, C1-C6 alkyl, or C1-C6 alkoxy; wherein the alkyl and alkoxy groups are optionally substituted with one to four halogen substituents;
when n is 1, Q1 represents a covalent bond, an oxygen atom, a sulphur atom, —SO—, —SO2—, —CO—, —C(O)O—, —CONR3—, —NR3—, —NR3CO—, —NR3CONR4—, —SO2NR3—, —NR3SO2—, —NR3SO2NR4—, —NR3C(O)O—, —NR3C(O)OR5—, C1-C6 alkylene, or C2-C6 alkenylene;
R2 represents a phenyl ring or a 5 to 10-membered heterocyclyl or heteroaryl ring, wherein said heterocyclyl and heteroaryl rings comprise 1, 2 or 3 heteroatoms, each independently selected from N, O and S;
wherein said R2 ring is optionally substituted with one to two substituents independently selected from halogen, cyano, oxo, hydroxyl, —NR6R7, —CONR6R7, —NR6COR7, —NR6CONR7R7a, —COR6, —C(O)OR6, —C1-C6 alkyl, —C1-C6 alkoxy, -Q2a-R8, -Q2b-CONR6-Q2c-R8, and -Q2-NR6SO2-Q2c-R8; wherein the alkyl and alkoxy groups are optionally substituted with one to four substituents selected from halogen and hydroxyl;
Q2a represents a covalent bond, an oxygen atom, a sulphur atom, —SO—, —SO2—, —CO—, or C1-C6 alkylene;
Q2b and Q2c each represent a covalent bond;
R3, R4 and R4a each independently represent hydrogen or C1-C6 alkyl;
R6, R7 and R7a each independently represent hydrogen or C1-C6 alkyl; and
R8 is selected from phenyl, piperazinyl, cyclopropyl, morpholinyl and piperidinyl; wherein R8 is optionally substituted by fluorine, chlorine, oxo, cyano, C1-C3 alkyl, or C1-C3 alkoxy.

US Pat. No. 10,654,852

ANTIBIOTICS AND METHODS OF USING SAME

THE BROAD INSTITUTE, INC....

1. A compound for treating bacterial infections having the structure of formula (I):
wherein A is N or CR7;
R1 is hydrogen or C1-5 linear or branched alkyl;
R7 is independently hydrogen, C1-5 linear or branched alkyl, or F; and
R2-R6 are independently selected at each occurrence from hydrogen, —X, -L1-X, or -L1-R;
where
—X is independently selected at each occurrence from —CN, —N(R)2, or —F;
L1 is selected independently at each occurrence from —NH—, —N(R)—, —C(O)—, —(CH2)1-4—, —C(O)—N(R)—, —(C(R)2)1-3—N(R)—, or —(C(R)2)1-3—;
R is independently selected at each occurrence from hydrogen, or C1-5 linear or branched alkyl;
wherein at least one of R2-R4 is a group -L1-R;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,654,851

DEUTERATED 3-(4,5-SUBSTITUTED AMINOPYRIMIDINE)PHENYL DERIVATIVES AND USE THEREOF

NANJING CHUANGTE PHARMACE...

1. A compound of Formula (I) or a pharmaceutically acceptable salt thereof,wherein: R1, R2, R3 and R4 are selected from the group consisting of —CH3 and ?CD3, and at least one of R1, R2, R3 and R4 is —CD3.

US Pat. No. 10,654,850

PYRIDAZINONES AND METHODS OF USE THEREOF

Goldfinch Bio, Inc., Cam...

1. A compound represented by:or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,654,849

(HETERO)ARYL-SUBSTITUTED-PIPERIDINYL DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

LES LABORATOIRES SERVIER,...

1. A compound of formula (I):
wherein:
R1 represents an aryl group or a heteroaryl group,
R2 represents a hydrogen atom or a halogen atom,
n is an integer equal to 0, 1 or 2,
J represents a —C(O)— group, a —CH(R3)— group, or an —SO2— group,
R3 represents a hydrogen atom or a linear or branched (C1-C6)alkyl group,
K represents a bond or a -Cy1- group,
L represents a -Cy2 group or a —CH2-Cy2 group,
W represents the group

 wherein
A represents a heteroaryl ring,
X represents a carbon atom or a nitrogen atom,
R4 represents a hydrogen atom, a halogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C2-C6)alkynyl group, a —Y1—NR6R7 group, a —Y1—OR6 group, a linear or branched halo(C1-C6)alkyl group, an oxo group, a —Y1-Cy3 group, a -Cy3-R7 group, a -Cy3-OR7 group, or a —Y1—NR6—C(O)—R7 group,
R5 represents a hydrogen atom, a halogen atom, or a linear or branched (C1-C6)alkyl group,
R6 represents a hydrogen atom or a linear or branched (C1-C6)alkyl group,
R7 represents a hydrogen atom, a linear or branched (C1-C6)alkyl group, or a —Y2-Cy4 group,
Y1 and Y2 independently of one another represent a bond or a linear or branched (C1-C4)alkylene group,
Cy1 represents a cycloalkyl group, a heterocycloalkyl group, an aryl group, or a heteroaryl group, which is linked to the group J and to the group L,
Cy2, Cy3 and Cy4 independently of one another, represent a cycloalkyl group, a heterocycloalkyl group, an aryl group, or a heteroaryl group,
wherein
“aryl” means a phenyl, naphthyl, or indanyl group,
“heteroaryl” means any mono- or fused bi-cyclic group composed of from 5 to 10 ring members, having at least one aromatic moiety and having from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen,
“cycloalkyl” means any mono- or fused bi-cyclic non-aromatic carbocyclic group having from 3 to 7 ring members,
“heterocycloalkyl” means any non-aromatic mono- or fused bi-cyclic group having from 3 to 10 ring members, and having from 1 to 3 heteroatoms selected from oxygen, sulphur and nitrogen,
wherein the aryl, heteroaryl, cycloalkyl and heterocycloalkyl groups so defined may be substituted by from 1 to 4 groups selected from linear or branched (C1-C6)alkyl, linear or branched (C2-C6)alkenyl, linear or branched (C2-C6)alkynyl, linear or branched halo(C1-C6)alkyl, —Y1—OR?, —Y1—NR?R?, —Y1—S(O)m—R?, oxo (or N-oxide where appropriate), nitro, cyano, —C(O)—R?, —C(O)—OR?, —O—C(O)—R?, —C(O)—NR?R?, —Y1—NR?—C(O)—R?, —Y1—NR?—C(O)—OR?, halogen, cyclopropyl, and pyridinyl which may be substituted by a linear or branched (C1-C6)alkyl group,
wherein R? and R?, independently of one another, represent a hydrogen atom, a linear or branched (C1-C6)alkyl group, a linear or branched (C2-C6)alkenyl group, a linear or branched (C1-C6)alkoxy group, a linear or branched halo(C1-C6)alkyl, a linear or branched hydroxy(C1-C6)alkyl group, a linear or branched (C1-C6)alkoxy(C1-C6)alkyl group, a phenyl group, a cyclopropylmethyl group, or a tetrahydropyranyl group,
or the substituents of the pair (R?, R?), together with the nitrogen atom carrying them, form a non-aromatic ring composed of from 5 to 7 ring members, which may have, in addition to the nitrogen, a second heteroatom selected from oxygen and nitrogen, wherein the second nitrogen in question may be substituted by from 1 to 2 groups selected from a hydrogen atom and a linear or branched (C1-C6)alkyl group,
and wherein m is an integer equal to 0, 1 or 2,
its enantiomers, diastereoisomers and addition salts thereof with a pharmaceutically acceptable acid or base.

US Pat. No. 10,654,848

NEUTROPHIL INFLAMMATION INHIBITOR AND USES THEREOF

Chang Gung University of ...

1. A compound of formula (I), a salt, or a solvate thereof:
wherein,
X is N or O;
R1 is alkyl or nil, in which R1 is nil when X is O, and R1 is alkyl when X is N;
R2, R3, R4, and R5 are independently H, hydroxyl, sulfhydryl, halogen, alkyl, haloalkyl, —OR6, —SR6, —(C?O)R6, or —COOH; and
R6 is alkyl or haloalykl.

US Pat. No. 10,654,847

SUBSTITUTED 2-(4-HETEROCYCLYLBENZYL)ISOINDOLIN-1-ONE ANALOGS AS POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M1

Vanderbilt University, N...

1. A compound having a structure represented by a formula:
wherein L is selected from (C?O)—, (S?O)— and —(SO2)—;
wherein Q1 is selected from N and CR1a; wherein Q2 is selected from N and CR1b; wherein Q3 is selected from N and CR1c; wherein Q4 is selected from N and CR1d; and wherein 0, 1, or 2 of Q1, Q2, Q3, and Q4 are N;
wherein each of R1a, R1b, R1c, and R1d, when present, is independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 polyhaloalkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylamino, C1-C6 haloalkyl-oxy-C1-C6 alkyl, C1-C6 polyhaloalkyl-oxy-C1-C6 alkyl, and C1-C6 dialkylamino;
wherein Q5 is selected from N and CR2a; wherein Q6 is selected from N and CR2b; wherein Q7 is selected from N and CR2c, wherein Q8 is selected from N and CR2d; and wherein 0, 1, or 2 of Q5, Q6, Q7, and Q8 are N;
wherein each of R2a, R2b, R2c, and R2d, when present, is independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 polyhaloalkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylamino, C1-C6 haloalkyl-oxy-C1-C6 alkyl, C1-C6 polyhaloalkyl-oxy-C1-C6 alkyl, and C1-C6 dialkylamino;
wherein each of R3a and R3b is independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 polyhaloalkyl;
wherein R4 is Ar2;
wherein Ar2 is selected from benzoimidazolyl, imidazopyridinyl, isoquinolinyl, oxoindolinyl, pyrazolyl, and quinolinyl; and wherein Ar2 is substituted with 0-3 substituents selected from halogen, hydroxyl, cyano, —NH2, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 polyhaloalkyl, C1-C6 alkylamino, and C1-C6 dialkylamino; and
and wherein each of R7a and R7b is independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 polyhaloalkyl;
or a pharmaceutically acceptable salt, solvate, or polymorph thereof.

US Pat. No. 10,654,846

AUTOTAXIN INHIBITORY COMPOUNDS

Cancer Research Technolog...

1. A compound which is:N—[(S)-1-(4-chloro-phenyl)-ethyl]-3-[3-(4-trifluoromethoxy-benzyl)-3H-imidazo[4,5-b]pyridin-2-yl]-propionamide,

or a pharmaceutically acceptable salt or solvate thereof.

US Pat. No. 10,654,845

2-(HET)ARYL-SUBSTITUTED FUSED BICYCLIC HETEROCYCLE DERIVATIVES AS PESTICIDES

BAYER CROPSCIENCE AKTIENG...

1. A compound of formula (I)whereinA1 represents nitrogen,
A2 represents N—R5,
A4 represents C—H,
R1 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
R2a represents hydrogen,
R2b represents a group selected from
—C(?O)—R8 (Q1), where R8 represents methoxy or ethoxy,
—C(?O)—NR11R12 (Q3), where R11 represents hydrogen or methyl and R12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—C(?S)—NR11R12 (Q4), where R11 represents hydrogen or methyl and R12 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—S(O)m—R13 (Q5), where m represents 0, 1 or 2 and R13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl or benzyl,
—S?O(?NH)—R13 (Q6), where R13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
—S(?N—CN)—R13 (Q8), where R13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl,
—S(O)2—NR11R12 (Q9), where R11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl and R12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—NR11R12 (Q10), where R11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl and R12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl,
—NR11—NR11R12 (Q11), where R11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl or COmethyl (acetyl) and R12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl or COmethyl (acetyl),
—NR11—C(?O)—R8 (Q12), where R11 represents hydrogen or methyl and R8 represents methyl, ethyl, n-propyl, isopropyl (where R8 represents methyl, ethyl, n-propyl, or isopropyl only if R11 does not represent hydrogen), trifluoromethyl, CHF2, CF2CF3, CF2CHF2, CH2OCH3, CH2SCH3, CH2OC2H5, CH2SOCH3, CH2SO2CH3, CH(CH3)CH2SCH3, CH(CH3)CH2SOCH3, CH(CH3)CH2SO2CH3, C2H4OC2H5, C2H4S C2H5, C2H4OC2H5, C2H4SOC2H5, C2H4SO2C2H5, CH(CH3)CH2SC2H5, CH(CH3)CH2SOC2H5, CH(CH3)CH2SO2C2H5, cyclopropyl, cyclopropylmethyl (—CH2-cyclopropyl), phenyl, benzyl,

NR11—C(?S)—R8 (Q13), where R8 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclopropyl and R11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropyl,
—NR11—S(O)2—R13 (Q14), where R11 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, methylsulphonyl or cyclopropyl and R13 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl or trifluoromethyl, and
—O—R13 (Q17), where R13 represents trifluoromethyl-1H-pyrazol-5-yl

with the proviso that if R2b represents Q5, Q6, Q8 or Q9, then n represents 2,
R3 represents fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R5 represents methyl, ethyl or isopropyl, and
n is 0, 1 or 2.

US Pat. No. 10,654,844

DUAL MECHANISM INHIBITORS FOR THE TREATMENT OF DISEASE

Aerie Pharmaceuticals, In...

1. A pharmaceutically acceptable salt of

US Pat. No. 10,654,842

DOPAMINE D3 RECEPTOR ANTAGONIST COMPOUNDS

INDIVIOR UK LIMITED, Hul...

1. A pharmaceutical composition comprising from about 0.1 mg to about 500 mg of a compound of Formula (I) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier; wherein the compound of Formula (I) is:wherein:A is a saturated 3-6 membered carbocyclic ring, optionally substituted by one or more C1-4alkyl;
B is a saturated 4-6 membered heterocyclic ring, in which one or two carbon atoms are optionally replaced by a heteroatom selected from nitrogen and oxygen, and wherein the ring is optionally substituted by one or more C1-4alkyl;
G is aryl or a 5-6 membered heteroaromatic group or 8-11 membered heteroaromatic group, which is optionally benzofused or optionally substituted by 1, 2, 3, 4, or 5 substituents selected from the group consisting of: halogen, cyano, hydroxyl, amino, C1-4alkylamino, C1-4alkyl, C1-4alkoxy, haloC1-4alkyl, haloC1-4alkoxy, SF5, C(?O)NH2, and C(?O)(O)R3;
W is S, SO2, O, CHR2, or NR3;
n is 0 or 1;
m is 1 or 2;
p is 1 or 2;
z is each independently 0 or 1;
R is hydrogen, C1-4alkoxy, or C1-4alkyl;
each R1 is independently hydrogen, OH, C1-4alkoxy, F, or C1-4alkyl;
each R2 is independently hydrogen, OH, C1-4alkoxy, F, or C1-4alkyl;
each R3 is independently hydrogen or C1-4alkyl;
each R4 is independently hydrogen, C1-4alkyl, —C(?O)C1-4alkyl, —C(?O)C1-4alkoxyC1-4alkyl, or —C(?O)C3-6cycloalkyl;
each R5 is independently hydrogen or C1-4alkyl;
each R6 is independently hydrogen or C1-4alkyl;
each R7 is each independently halogen, C1-4alkyl, OH, or C1-4alkoxy;
G1 is a phenyl or a 5-6-membered heteroaromatic group or a 8-11 membered heteroaromatic group; any of which groups is optionally substituted by 1, 2, 3, or 4 substituents selected from the group consisting of halogen, cyano, hydroxyl, amino, C1-4alkylamino, haloC1-4alkoxy, C1-4alkoxy, SF5, C(?O)NH2, and C(?O)(O)R3;
Y is phenyl or a moiety selected from the group consisting of a 5-6 membered heteroaromatic group, an 8-11 membered heteroaromatic group, a saturated mono 3-7 membered carbocyclic group and a 8-11 membered bicyclic carbocyclic group; and for any of such groups one or more ring carbons is optionally replaced by N(R4)z, O, or S; and any of which groups is optionally substituted by 1, 2, or 3 substituents selected from the group consisting of halogen, cyano, hydroxyl, C1-4alkylamino, C1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, oxo, —NHC(?O)C1-4alkyl, —NR5R6, SF5, —(CH2)zC(?O)NR5R6, —C(?O)(O)zR3, —C1-4alkylCN, —SO2NR5R6, Y?, and OY?;
Y? is phenyl or a 5-6-membered heteroaromatic group optionally substituted by one or two R7 groups; provided that Y, Y? and G1 are not simultaneously phenyl.

US Pat. No. 10,654,841

PROCESSES WITH TERMINAL TRANSFERASE, AMINOXY NUCLEOSIDE TRIPHOSPHATES, AND NUCLEOBASE ANALOGS

1. A process for synthesizing an oligonucleotide that has a 3?-ONH2 moiety instead of a 3?-OH moiety, said process comprising contacting an oligodeoxyribonucleotide in an aqueous buffered solution with terminal deoxynucleotide transferase and a nucleoside triphosphate having the structure:
or one of its ionized forms, wherein B is a heterocycle selected from the group consisting of

wherein Su indicates the point of attachment of the heterocycle to the sugar, and
wherein said solution contains less than 1 micromolar hydroxylamine.

US Pat. No. 10,654,840

PYRIMIDINYLOXY BENZENE DERIVATIVES AS HERBICIDES

FMC Corporation, Philade...

1. A compound selected from Formula 1, N-oxides and salts thereof,
Q is a 5- or 6-membered aromatic heterocylic ring, bound to the remainder of Formula 1 through a carbon atom, and is selected from the group consisting of

wherein r is 0, 1, 2 or 3;
Z is O or S;
each R1 is independently selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy;
R2 is selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl and C3 -C6 cycloalkyl;
each R3 is independently selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy;
m is 0, 1, 2 or 3;
each n is independently 0, 1 or 2.

US Pat. No. 10,654,839

COMPOSITIONS AND METHODS FOR VIRAL SENSITIZATION

Ottawa Hospital Research ...

1. A method for enhancing or increasing viral production in cells comprising administering a compound of Formula (II):
or a pharmaceutically acceptable salt, or stereochemically isomeric form thereof, wherein:
X1 is substituted N;
X2 is halogen or NHX3, wherein X3 is a substituted or unsubstituted, linear or branched alkyl, alkenyl, or alkynyl; or substituted or unsubstituted aryl or heteroaryl;
i is 0;
- - - is absent when i is 0 such that X1 is directly bonded to the X4-bearing carbon through a single bond; and
X4 is OH;
to said cells prior to, after or concurrently with a virus, and culturing the virus and cells.

US Pat. No. 10,654,838

AMINOPYRIDINE COMPOUNDS USEFUL AS INHIBITORS OF PROTEIN PRENYLATION

INSTITUT NATIONAL DE LA S...

1. A method of treating diseases or disorders wherein an inhibition of protein prenylation is required comprising at least a step of administering to an individual in need thereof at least one compound or pharmaceutically acceptable salts thereof, enantiomers thereof, diastereoisomers thereof, or racemic mixtures thereof, wherein the compound is selected from the group consisting of
wherein
R1 is 2-pyridyl, 3-pyridyl or 4-pyridyl;
R2 represents a group which is selected from the group consisting of:
R3 representing a group which is selected from the group consisting of:an arylcarbonyl group,
a heteroarylcarbonyl group,
a (C1-C4)alkoxy-carbonylmethyl group, and
a
group, Ra, Rb, Rc, Rd and Re being, independently a hydrogen atom, a halogen atom, a (C1-C4)alkyl group, or a (C1-C4)alkoxy group, or Ra and Rb, or Rb and Rc, or Rc and Rd, or Rd and Re together optionally forming with the carbon atom to which they are attached a 5- or 6-membered ring fused to the phenyl ring comprising two oxygen atoms,and R4 being a phenyl group substituted by a halogen atom, or a benzyl group;
provided that
R3 is not a 4-methylbenzyl group when R1 is 2-pyridyl,
and

wherein
R5 represents a hydrogen atom or a (C1-4)alkyl group;
R6 represents a hydrogen atom or a (C1-4)alkyl group; and
R7 represents a group which is selected from the group consisting of:
an arylcarbonyl group,
a heteroarylcarbonyl group optionally substituted by one or two groups selected from a (C1-4)alkyl group and a phenyl group,
a heteroarylacetyl group optionally substituted on the heteroaryl ring by a phenyl group,
a (C1-C4)alkoxy-carbonylmethyl group, and
a
group, Ra, Rb, Rc, Rd and Re being, independently a hydrogen atom, a halogen atom, a (C1-C4)alkyl group, or a (C1-C4)alkoxy group, or Ra and Rb, or Rb and Rc, or Rc and Rd, or Rd and Re together optionally forming with the carbon atom to which they are attached a 5- or 6-membered ring fused to the phenyl ring comprising two oxygen atoms,provided that
R7 is not an indol-3-ylacetyl group when R5 and R6 are both a methyl group.

US Pat. No. 10,654,837

SULPHAMOYLARYL DERIVATIVES AND USE THEREOF AS MEDICAMENTS FOR THE TREATMENT OF LIVER FIBROSIS

Janssen Pharmaceutica NV,...

6. A method of preventing or treating liver fibrosis and/or cirrhosis in a mammal comprising administering a therapeutically effective amount of at least one compound according to Formula A
or a stereoisomer or tautomeric form, and/or a salt or solvate thereof, wherein
Ar represents a monocyclic or bicyclic aromatic ring, optionally containing one or more heteroatoms each independently selected from the group consisting of O, S and N, such aromatic ring optionally being substituted with one or more substituents each independently selected from the group consisting of hydrogen, halogen, —CN, —OH, C1-C3 alkyl, C3-C7cycloalkyl, —O(R6), CHF2, CH2F and CF3;
R1 represents hydrogen, a 3-7 membered saturated ring optionally containing one or more heteroatoms each independently selected from the group consisting of O, S and N, or C1-C6 alkyl, such 3-7 membered saturated ring or C1-C6alkyl optionally being substituted with one or more substituents each independently selected from the group consisting of C1-C3 alkyl, halogen, CHF2, CH2F and CF3, —CN, —C(?O)R5, oxo-C(?O) N(R6)2, —N(R6)2 and —OR6;
R2 represents hydrogen, or C1-C3 alkyl;
R3 represents Fluor or —OC1-C3 alkyl optionally substituted with one or more Fluor;
R4 represents hydrogen, Fluor or —OC1-C3 alkyl;
R6 represents hydrogen, C1-C3 alkyl optionally substituted with one or more Fluor, or —C1-C3 alkyl-O(R5);
R5 represents hydrogen or C1-C3 alkyl.

US Pat. No. 10,654,836

PYRIMIDINE DERIVATIVE, METHOD FOR PREPARING SAME AND USE THEREOF IN MEDICINE

Zhejiang Hisun Pharmaceut...

1. A compound represented by formula (I) or a stereoisomer, tautomer thereof or a pharmaceutically acceptable salt thereof:
wherein:
each of R1 is independently selected from alkyl, halogen, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, —NR7R8, —C(O)NR7R8, —C(O)R9, —C(O)OR9 or —NR7C(O)R8, wherein the alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of hydroxyl, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, —NR7R8, —C(O)NR7R8, —C(O)R9, —C(O)OR9 and —NR7C(O)R8;
R2 is selected from:
—NR4C(O)CR5?CHR6 or —NR4C(O)C?CR5;
R3 is a spiroheterocyclyl, wherein the spiroheterocyclyl is optionally further substituted by one or more substituents selected from the group consisting of hydroxyl, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, haloalkoxy, —NR7R8, —C(O)NR7R8, —C(O)R9, —C(O)OR9 and —NR7C(O)R8;
each of R4 is independently selected from hydrogen or alkyl, wherein the alkyl is optionally further substituted by one or more substituents selected from the group consisting of hydroxy, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, haloalkoxy, —NR7R8, —C(O)NR7R8, —C(O)R9, —C(O)OR9 and —NR7C(O)R8;
R5 and R6 are each independently selected from hydrogen, alkyl or halogen, wherein the alkyl is optionally further substituted by one or more substituents selected from the group consisting of hydroxy, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, haloalkoxy, —NR7R8, —C(O)NR7R8, —C(O)R9, —C(O)OR9 and —NR7C(O)R8;
R7, R8 and R9 are each independently selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl, wherein the alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of hydroxy, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, —NR10R11, —C(O)NR10R11, —C(O)R12, —C(O)OR12 and —NR10C(O)R11;
alternatively, R7 and R8 together with the N atom to which they are attached form a 4 to 8 membered heterocyclyl, wherein the 4 to 8 membered heterocyclic ring contains one or more N, O, S(O)n atoms, and the 4 to 8 membered heterocyclic ring is further substituted by one or more substituents selected from the group consisting of hydroxy, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, ?O, —NR10R11, —C(O)NR11R11, —C(O)R12, —C(O)OR12 and —NR10C(O)R11;
R10, R11 and R12 are each independently selected from hydrogen, alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl, wherein the alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl are optionally further substituted by one or more substituents selected from the group consisting of hydroxy, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, carboxylic acid or carboxylate;
m is 1, 2, 3 or 4; and
n is 0, 1, or 2.

US Pat. No. 10,654,834

NON-SYSTEMIC TGR5 AGONISTS

Venenum Biodesign, LLC, ...

1. A compound of formula (I)
or a pharmaceutically acceptable salt thereof, wherein:
each R1 is independently CN, C1-6alkyl, pyridyl, or C1-6alkoxy, wherein alkyl group is optionally further substituted with 1-4 halogen;
m is 0, 1, 2 or 3;
R2 is C1-6alkyl or H, wherein alkyl group is optionally further substituted with 1-4 halogen;
X is CH or N;
P is CH or N;
L1, L2 and L3 are each independently absent,

wherein N is optionally further substituted with C1-3alkyl;
n1, n2, n3 and n4 are each independently 0, 1, 2, 3, 4 or 5, and when L1 is absent, n2 is 0, when L2 is absent, n3 is 0, when L3 is absent, n4 is 0, with the proviso that when L1, L2 and L3 are all absent, n1 cannot be 0;
each R is independently H, OH, NH2, COOH, C1-6alkylCOOH, COOC1-6alkyl, C1-6 alkylOH or C1-6 alkylNHC(NH)NH2;
T is

CN, OH, NH2 or OCH3, wherein N is optionally further substituted with C1-3 alkyl;
R3 and R4 are each independently H, OH, halogen, N(CH3)2 or NH2; and
n is 0, 1 or 2.

US Pat. No. 10,654,833

ASK1 ISOINDOLIN-1-ONE INHIBITORS AND METHODS OF USE THEREOF

Hepatikos Therapeutics, L...

1. A compound, or a pharmaceutically acceptable salt thereof, of Formula I:
wherein:
Ring A is selected from the group consisting of aryl, heteroaryl, 5-6-membered heterocyclyl, and 4-6-membered carbocyclyl;
R1 is selected from the group consisting of —(C1-6 alkylene)pCO2R20, —O(C1-6 alkylene)pCO2R20, —(C1-6 alkylene)p(carbocyclylene)CO2R20, —O(C1-6 alkylene)p(carbocyclylene)CO2R20, unsubstituted —(C2-9 alkenyl), unsubstituted —(C2-9 alkynyl), unsubstituted —(C1-9 haloalkyl), —(C1-6 alkylene)carbocyclyl optionally substituted with 1-10 R4, —(C1-6 alkylene)pheterocyclyl optionally substituted with 1-10 R5, —(C1-6 alkylene)paryl optionally substituted with 1-5 R6, —(C1-6 alkylene)pheteroaryl optionally substituted with 1-5 R7, —(C1-6 alkylene)pOR8, —(C1-6 alkylene)pSR8, —(C1-6 alkylene)pS(?O)R9, —(C1-6 alkylene)pSO2R10 , —(C1-6 alkylene)pN(R11)SO2R12, —(C1-6 alkylene)pSO2N(R13)2, —(C1-6 alkylene)pN(R14)2, —(C1-6 alkylene)pN(R11)C(?O)N(R15)2, —(C1-6 alkylene)pNR11C(?O)OR16, —(C1-6 alkylene)pC(?O)N(R17)2, —(C1-6 alkylene)pN(R11)C(?O)R18, and —(C1-6 alkylene)pOC(?O)N(R19)2; wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more substituents as defined anywhere herein; wherein each (carbocyclylene) is, independently, optionally substituted with one or more substituents as defined anywhere herein; wherein each CO2R20 can be replaced with a carbocyclic acid bioisostere thereof;
R2 is selected from the group consisting of halide, Me, OMe, CN, —SO2R10, —N(R14)2, —(C1-4 alkylene)pOH; wherein —(C1-4 alkylene) of —(C1-4 alkylene)pOH is optionally substituted with one or more OH;
alternatively, an adjacent R1 and R2 are taken together with the atoms to which they are attached to form a ring which is selected from the group consisting of

R3 is selected from the group consisting of unsubstituted —(C1-9 alkyl), unsubstituted —(C2-9 alkenyl), unsubstituted —(C2-9 alkynyl), unsubstituted —(C1-9 haloalkyl), —(C1-4 alkylene)OR21, and —(C1-4 alkylene)pcarbocyclyl optionally substituted with one or more halides; wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
each R4 is selected from the group consisting of halide, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —OH, —N(R23)2, —CN, and —OMe;
each R5 is selected from the group consisting of halide, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —OH, —N(R23)2, —CN, and —OMe;
each R6 is selected from the group consisting of halide, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —OH, —N(R23)2, —CN, and —OMe;
each R7 is selected from the group consisting of halide, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —OH, —N(R23)2, —CN, and —OMe;
R8 is selected from the group consisting of H, unsubstituted —(C3-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
R9 is selected from the group consisting of unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
R10 is selected from the group consisting of unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
each R11 is selected from the group consisting of H, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), and unsubstituted —(C1-6 haloalkyl);
R12 is selected from the group consisting of unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
each R13 is selected from the group consisting of H, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
each R14 is selected from the group consisting of H, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
each R15 is selected from the group consisting of H, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
R16 is selected from the group consisting of unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
each R17 is selected from the group consisting of H, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
R18 is selected from the group consisting of unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
each R19 is selected from the group consisting of H, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
R20 is selected from the group consisting of H, unsubstituted —(C1-6 alkyl), unsubstituted —(C2-6 alkenyl), unsubstituted —(C2-6 alkynyl), unsubstituted —(C1-6 haloalkyl), —(C1-3 alkylene)pcarbocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)pheterocyclyl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), —(C1-3 alkylene)paryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl), and —(C1-3 alkylene)pheteroaryl optionally substituted with one of more halides and/or unsubstituted —(C1-6 alkyl); wherein each —(C1-4 alkylene) is, independently, optionally substituted with one or more halides;
R21 is selected from the group consisting of H, unsubstituted —(C1-5 alkyl), unsubstituted —(C2-5 alkenyl), unsubstituted —(C2-5 alkynyl), and unsubstituted —(C1-5 haloalkyl);
each n is independently 0 to 5; and
each p is independently 0 or 1.

US Pat. No. 10,654,832

3-(BENZOIMIDAZOL-2-YL)-INDAZOLE INHIBITORS OF THE WNT SIGNALING PATHWAY AND THERAPEUTIC USES THEREOF

Samumed, LLC, San Diego,...

1. A compound, or pharmaceutically acceptable salt thereof, of Formula I:wherein:R1 is -pyridinylR3R4;
R2 is -thiophenylR5;
R3 is 1 substituent attached to the heteroaryl ring and is selected from the group consisting of H, C1-3 alkyl, —CF3, —NR9R10, —NHC(?O)R8, and —(C1-3 alkyl)NR9R10;
R4 is 1 substituent attached to the pyridinyl ring and is selected from the group consisting of H, C1-3 alkyl, —CF3, halide, —CN, —OR8, —OH, —(C1-3 alkyl)OR8, —NR9R10, —(C1-3 alkyl)NR9R10 and —OCF3;
R5 is 1-3 substituents attached to the pyridinyl ring and each is independently selected from the group consisting of H, C1-3 alkyl, —CF3, halide, —CN, —OR8, —OH, —(C1-3 alkyl)OR8, —NR9R10, —(C1-3 alkyl)NR9R10 and —OCF3;
each R8 is independently selected from the group consisting of C1-9 alkyl, -arylR14, carbocyclylR11, —(C1-3 alkyl)arylR14 and —(C1-3 alkyl)carbocyclylR11;
each R9 is independently selected from the group consisting of H, C1-6 alkyl, -arylR14, carbocyclylR1, —(C1-3 alkyl)arylR14 and —(C1-3 alkyl)carbocyclylR11;
each R10 is independently selected from the group consisting of H and C1-6 alkyl;
R11 is 1-3 substituents attached to the carbocyclyl ring and each independently selected from the group consisting of H, C1-3 alkyl, —CF3, halide, —CN, —O(R10), —(C1-3 alkyl)OR10, —N(R10)2, —(C1-3 alkyl)N(R10)2 and —OCF3; and
R14 is 1-3 substituents attached to the aryl ring and each is independently selected from the group consisting of H, C1-3 alkyl, —CF3, halide, —CN, —O(R10), —(C1-3 alkyl)OR10, —N(R10)2, —(C1-3 alkyl)N(R10)2 and —OCF3.

US Pat. No. 10,654,831

ANTIPROLIFERATIVE PYRIMIDINE-BASED COMPOUNDS

G1 Therapeutics, Inc., R...

19. A pharmaceutical composition comprising an effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.

US Pat. No. 10,654,830

HISTONE DEMETHYLASE INHIBITORS

CELGENE QUANTICEL RESEARC...

1. A compound having the structure of Formula II
wherein a compound of Formula II is optionally a pharmaceutically acceptable salt thereof, and wherein
R2 is halogen or —CF3;
R3 is hydrogen, halogen, —OH, —OR6, —N(R6)2, or alkyl, carbocyclyl, aryl optionally substituted with halogen, carbocyclylalkyl, or aralkyl optionally substituted with halogen or alkyl;
R4 is hydrogen, halogen, —OH, —OR6, —N(R6)2, or alkyl, carbocyclyl, aryl, carbocyclylalkyl, or aralkyl; wherein
each R6 is independently hydrogen, alkyl, carbocyclyl, aryl, carbocyclylalkyl, or aralkyl; and
R5 is hydrogen, methyl, ethyl, isopropyl, t-butyl, —CHF2, —CH2F, —CF3, —CH2OH, —CHCH3OH, or —C(CH3)2OH.

US Pat. No. 10,654,829

CRYSTALLINE FORMS AND COMPOSITIONS OF CFTR MODULATORS

Vertex Pharmaceuticals In...

1. Crystalline Form B of a potassium salt of Compound I:characterized by an X-ray powder diffractogram having a signal at at least three two-theta values chosen from 5.8±0.2, 8.2±0.2, 9.6±0.2, 10.2±0.2, 13.8±0.2, 15.1±0.2, 16.3±0.2, 17.2±0.2, and 19.1±0.2.

US Pat. No. 10,654,828

INDOLE DERIVATIVES AND USES THEREOF

NOVARTIS AG, Basel (CH)

1. A compound of formula (I) or a pharmaceutically acceptable salt thereof:wherein:L is absent, O, S, NHCO or CONH;
X is CH or N;
R1 is H, C1-4alkyl, C1-4haloalkyl, or 3-6 membered cycloalkyl;
R2 is H, —OH, halo, —CN, nitro, C1-4alkoxy, C1-4alkyl, C1-4alkoxy-C1-4alkyl, C1-4haloalkyl, C1-4hydroxyalkyl, a 5-10 membered heterocyclyl optionally substituted with 1-3 C1-4alkyl groups, —(CH2)n-(6 or 10 membered aryl optionally substituted with 1-3 C1-4alkyl groups), or —(CH2)n-(5-10 membered heteroaryl optionally substituted with 1-3 C1-4alkyl groups);
R3 is H, halo, —OH, C1-4alkyl, C1-4alkoxy, C1-4haloalkyl or C1-4 haloalkoxy;
R4 is a substituted C2-4alkynyl, a substituted or unsubstituted 5-10 membered heterocyclyl, a substituted or unsubstituted 5-10 membered heteroaryl, a substituted or unsubstituted 5-10 membered fused heterocyclyl-aryl, a substituted or unsubstituted 5-10 membered fused heterocyclyl-heteroaryl, or a substituted or unsubstituted 6 or 10 membered aryl, wherein when R4 is substituted, R4 is substituted with 1-3 substituents independently selected from halo, —OH, oxo (?O), —CN, nitro, C1-4alkyl, —C1-4alkyl-(3-6 membered cycloalkyl), C1-4alkoxy, —SO2—C1-4alkyl, —SO2—C1-4hydroxyalkyl, —SO2—C1-4alkyl-NR5R6, —NHSO2—C1-4alkyl, C1-4hydroxyalkyl, —SO2NR5R6, —CO—C1-4hydroxyalkyl, —CONR5R6, —CO—C1-4alkyl-NR5R6, —CO—NH—C1-4alkyl-NR5R6,—NR5R6, —C1-4alkyl-NR5R6 and —CO—C1-4alkyl;
R5 and R6 are each, independently, selected from H, C1-4alkyl, C1-4hydroxyalkyl, —CO—C1-4alkyl and -(4-10 membered heterocyclyl)-C1-4alkyl; or R5 and R6, together with the nitrogen atom to which they are attached, form a 5-7 membered heterocyclyl optionally substituted with 1-3 C1-4alkyl groups; and
n is 0 or 1.

US Pat. No. 10,654,827

THERAPEUTIC COMPOUNDS

Gilead Sciences, Inc., F...

1. A method of treating a human immunodeficiency virus (HIV) infection comprising administering a therapeutically effective amount of a compound of Formula (Ia):
or a pharmaceutically acceptable salt thereof, to a subject in need thereof.

US Pat. No. 10,654,826

1,3,5-TRIAZINE DERIVATIVE AND METHOD OF USING SAME

Chia Tai Tianqing Pharmac...

7. A pharmaceutical composition, comprising the compound according to claim 1, or a pharmaceutically acceptable salt or hydrate thereof, and one or more pharmaceutically acceptable carriers or excipients.

US Pat. No. 10,654,825

PROCESSES FOR MAKING TRIAZOLO[4,5D] PYRAMIDINE DERIVATIVES AND INTERMEDIATES THEREOF

CORVUS PHARMACEUTICALS, I...

1. A method of isolating a precipitate of the formula (I):comprising the steps of:(a) reacting a compound of the formula:

with a compound of the formula:
in the presence of a base;wherein,
X1 and X2 are independently halo, and
wherein R is —(CRaRb)—O—R2;
Ra is H or alkyl;
Rb is H or alkyl; or Ra and Rb together with the atom to which they are attached form a 3 to 8 membered saturated or partially saturated hydrocarbon ring or form a 4 to 8 membered saturated or partially saturated heterocylic ring comprising a ring member selected from O, N(R3) and S;
R2 is H, alkyl, cycloalkyl or heterocycloalkyl, wherein said alkyl or cycloalkyl may optionally be substituted with halo, alkoxy or heterocycloalkyl;
R3 is H or alkyl;
wherein, heteroaryl is a 5 or 6 membered aromatic ring, comprising one or two ring members selected from N, N(R4), S and O;
alkyl (or the alkyl group of the alkoxy group) is a linear or branched saturated hydrocarbon containing up to 10 carbon atoms;
heterocycloalkyl is a C-linked or N-linked 3 to 10 membered non-aromatic, monocyclic ring, wherein said heterocycloalkyl ring comprises 1, 2 or 3 ring members independently selected from N, N(R4), S(O)q and O;
R4 is H or alkyl; and
q is 0, 1 or 2; and
(b) isolating the precipitate of formula (I).

US Pat. No. 10,654,824

2-AZABICYCLO[3.1.0]HEXAN-3-ONE DERIVATIVES AND METHODS OF USE

Genentech, Inc., South S...

18. A pharmaceutical composition comprising a compound of claim 1, or a stereoisomer, tautomer, solvate or prodrug thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.

US Pat. No. 10,654,819

PROCESSES FOR THE PREPARATION OF 2,5-FURANDICARBOXYLIC ACID AND INTERMEDIATES AND DERIVATIVES THEREOF

Stora Enso Oyj, Helsinki...

1. A process for producing a first 2,5-furandicarboxylic acid (FDCA) pathway product from a first furanic oxidation substrate, the process comprising:(a) contacting a first oxidation feedstock comprising a first furanic oxidation substrate and a first oxidation solvent with oxygen in the presence of a first heterogeneous oxidation catalyst under conditions sufficient to form a reaction mixture for oxidizing the first furanic oxidation substrate to a first FDCA pathway product, and producing the first FDCA pathway product;
wherein the first oxidation solvent is a multi-component solvent comprising water and a water-miscible aprotic organic solvent;
wherein no base is added to the reaction mixture during (first) contacting step (a);
wherein the first heterogeneous oxidation catalyst comprises a first solid support and a first noble metal, and
wherein the solid support comprises a specific surface area in the range of from or any number in between 20 m2/g to 100 m2/g.

US Pat. No. 10,654,818

FURANE DERIVATIVES AS INHIBITORS OF ATAD2

BAYER PHARMA AKTIENGESELL...

1. A compound of general formula I
in which
R1 represents a benzyl group wherein the ?-position is substituted by one methyl group of R configuration or two methyl groups, and the 4-position may be substituted by a methyl group, a halogen atom, a 4-trifluoromethyl group,
R2 represents a C1-6-alkyl group,
a C1-6-hydroxyalkyl group,
a —C1-3-alkylen-O—(C1-6-alkyl) group,
a —C1-6-aminoalkyl group,
a —C1-3-alkylen-N—(C1-6-alkyl)2 group,
a —C1-3-alkylen-NH—(C1-6-alkyl) group,
a —C1-3-alkylen-NH—(C1-4-alkyl)-OH group,
a —C1-3-alkylen-NH—(C3-7-cycloalkyl)-NH2 group,
a —C1-3-alkylen-NH—C1-4-alkylen-heterocycloalkyl group which is optionally substituted with C1-3-alkyl,
a —C1-3-alkylen-NH-heterocycloalkyl group which is optionally substituted independently from each occurrence one or more times with C1-4-alkyl, halogen, benzyl, C(O)R7,
a —C1-3-alkylen-NH—(C1-3-alkylen)-phenyl group,
a —C1-3-alkylen-NH—C(O)(C1-4-alkyl) group,
a —C1-3-alkylen-NH—C(O)—C1-4-alkylen-heterocycloalkyl group,
a —C1-3-alkylen-NH—C1-3-alkylen-C(O)-heterocycloalkyl group,
a —C1-3-alkylen-NH—C(O)-heterocycloalkyl group,
a —C1-3-alkylen-NH—S(O)2-(C1-4-alkyl) group,
a —C1-3-alkylen-(4-cyano-phenyl) group, a —C1-3-alkylen-C(O)—NH—(C1-6-alkyl) group,
a —C1-3-alkylen-C(O)—NH—(C1-4-alkyl)-OH group,
a —C1-3-alkylen-C(O)—NR8R9 group,
a —C1-3-alkylen-C(O)—R7 group,
a —C1-3-alkylen-C(O)-heterocycloalkyl group which is optionally substituted with C1-3-alkyl,
a —C1-3-alkylen-heterocycloalkyl group which is optionally one or more times substituted with C1-3-alkyl,
a C(O)R7 group,
a —C(O)—NR8R9 group,
a C(O)—NH—(C3-7-cycloalkyl)-NH2 group,
a —C(O)—NH-heterocycloalkyl group which is optionally substituted with C1-3-alkyl, a heteroaryl group,
R3 a —C1-3-alkylen-phenyl group which is independently from each occurrence optionally substituted 1 to 3 times with a substituent selected from the group cyano, halogen, C1-3-alkyl, C1-3-alkoxy, amino, C(O)R7, C(O)NR8R9,
a —C1-4-alkylen-heteroaryl group, or
R2 and R3 together with the carbon atom to which they are attached form the following 6-membered ring whereby the star * indicates the carbon atoms which are attached to said carbon atom of absolute configuration R

R4 represents a hydrogen atom, a methyl group, a chlorine atom,
R5 represents a hydrogen atom or a halogen atom,
R6 represents a hydrogen atom, a halogen atom, a hydroxy group, a C1-3 alkoxy group, or a cyano group,
R7 represents a —O—C1-4-alkyl group,
R8, R9, represents, independently for each occurrence, a hydrogen atom or a C1-4-alkyl group, or the salts thereof, the solvates thereof or the solvates of the salts thereof,
with the proviso that the following compounds
2-Chlor-N-[(2R)-1-(4-cyanphenyl)-4-(methylamino)-4-oxobutan-2-yl]-5-[5-({[(1R)-1-(4-methylphenyl)ethyl]amino}methyl)-2-furyl]benzamide
N-[(2R)-1-(4-cyanophenyl)-4-(methylamino)-4-oxobutan-2-yl]-2-fluoro-5-[5-({[(1R)-1-(4-methylphenyl)ethyl]amino}methyl)-2-furyl]benzamide
2-chloro-N-[(2R)-1-(4-fluorophenyl)-4-(methylamino)-4-oxobutan-2-yl]-5-[5-({[(1R)-1-(4-methylphenyl)ethyl]amino}methyl)-2-furyl]benzamide
N-[(2R)-1-(4-cyanophenyl)-4-(methylamino)-4-oxobutan-2-yl]-2-methyl-5-[5-({[(1R)-1-(4-methylphenyl)ethyl]amino}methyl)-2-furyl]benzamide
2-chloro-N-[(2R)-1-(4-cyanophenyl)-4-(methylamino)-4-oxobutan-2-yl]-5-[5-({[(1R)-1-(4-fluorophenyl)ethyl]amino}methyl)-2-furyl]benzamide
are excluded.

US Pat. No. 10,654,817

ORGANO-1-OXA-4-AZONIUM CYCLOHEXANE COMPOUNDS

1. A morpholinium compound comprising a 1-oxa-4-azonium cyclohexane salt having a structure of:
wherein R1-R8 are independently selected from H or an alkyl group having the formula CnH2n+1, R9 is C2H5, where n is in the range from 1 to 4, X is halide or hydroxide, the total number of C atoms in the molecule is in the range of 11 to 24, and R10 is an alkyl group having the formula CmH2m, where m is in the range from 3 to 8 and is connected to the 4 and 4? N atoms at positions x and y of the alkyl chain where x and y are independently selected from 1 to m; with the proviso that: when R1-R8 are H, R9 is C2H5, R10 is C6H12, x is 1, and y is 6, X is hydroxide.

US Pat. No. 10,654,815

UREA COMPOUND AND PREPARATION METHOD AND APPLICATION THEREOF

SHENZHEN CHIPSCREEN BIOSC...

1. A compound of Formula I,or a prodrug, a stereoisomer, and a pharmaceutically acceptable salt or a hydrate thereof; wherein,R1 is one or more substituents independently selected from the group consisting of H, C1-C4 alkyl, CN, halogen, NH2, COOH, C1-C4 alkylamino, C1-C4 alkyloxy, C1-C4 haloalkyl and Ar1, which substituents are the same or different;
wherein,
Ar1 is selected from the group consisting of
wherein,R4 is one or more substituents independently selected from the group consisting of H, C1-C4 alkyl, CN, halogen, NH2, COOH, C1-C4 alkylamino, C1-C4 alkyloxy and C1-C4 haloalkyl, which substituents are the same or different;
i is an integer from 1 to 5;
Z is selected from the group consisting of C, NH, O, C(O), S, S(O) and S(O)2;
R2 is selected from the group consisting of H, C1-C4 alkyl, —CH2—(CH2)k—CN and —(CH2)k—Ar2;
wherein,
k is an integer from 0 to 6;
Ar2 is selected from

wherein,
R5 is one or more substituents independently selected from the group consisting of H, C1-C4 alkyl, CN, halogen, NH2, COOH, C1-C4 alkylamino, C1-C4 alkyloxy and Ci-C4 haloalkyl, which substituents are the same or different;
v is an integer from 1 to 5;
R3 is one or more substituents independently selected from the group consisting of H, C1-C4 alkyl, CN, halogen, C1-C4 alkyloxy and C1-C4 haloalkyl, which substituents are the same or different;
X is selected from C and N;
Y is selected from NH, O, S, S(O) and S(O)2;
A is selected from the group consisting of
or A is a side chain of an amino acid selected from the group consisting of Gly, Ala, Ser, Lys, Arg, Thr, Asn, Gln, Phe or Gluor A is a side chain of an amino acid selected from the group consisting of Gly, Ala, Ser, Lys, Arg, Thr, Asn, Gln, Phe and Glu, which is substituted with R6
wherein,
R6 is one or more substituents independently selected from the group consisting of H, C1-C4 alkyl, C1-C4 alkylcarbonyl, alkenylcarbonyl and C1-C4 alkylamino C1-C4 alkyl C1-C4 alkenylcarbonyl, which substituents are the same or different;
het is selected from saturated or aromatic heterocycles, morpholine, N-methylpiperazine, tetrahydropyrrole, pyridine, thiophene, thiazole, triazole and tetrazole;
w is an integer from 0 to 2;
m is an integer from 1 to 5;
n is an integer from 1 to 3;
p is independently an integer from 0 to 2; and
q is an integer from 0 to 2.

US Pat. No. 10,654,814

BICYCLIC HYDROXAMIC ACIDS USEFUL AS INHIBITORS OF MAMMALIAN HISTONE DEACETYLASE ACTIVITY

KANCERA AB, (SE)

1. A compound of formula (Ia) or (Ib)
or a pharmaceutically acceptable salt thereof, wherein
R1 is

wherein
each R2 is independently selected from C1-C6 alkyl, C3-C6 cycloalkyl, halogen, cyano, R3Y1-Q2, R4R5N-Q3, R6S(O)2-Q4, and

and two R2 attached to adjacent atoms of ring A1, together with the atoms to which they are attached, may form a 5- to 10-membered monocyclic or bicyclic ring, said ring optionally being substituted by one or more moieties selected from C1-C6 alkyl, C1-C6 alkoxy, halogen, and hydroxy;
R3 is selected from H, C1-C6 alkyl, R8O-Q6, and R9R10N-Q7;
R4 and R5 are independently selected from H, C1-C6 alkyl, C3-C8 cycloalkyl and R11O-Q8;
or R4 and R5, together with the nitrogen atom to which they are both attached, form a 5- or 6-membered ring, which ring is optionally substituted by one or more moieties selected from C1-C6 alkyl and R12O-Q9;
R6 is selected from H and C1-C6 alkyl;
each R7 is independently selected from C1-C6 alkyl, halogen, R13O-Q10, R14R15N-Q11, and R16S(O)2-Q12, and two R7 attached to adjacent atoms of ring A2, together with the atoms to which they are attached, may form a 5- or 6-membered ring;
R8 is selected from H and C1-C6 alkyl;
R9 and R10 are independently selected from H and C1-C6 alkyl; or R9 and R10, together with the nitrogen atom to which they are both attached, form a 5- or 6-membered ring;
each one of R11, R12 and R13 is selected from H and C1-C6 alkyl;
R14 and R15 are independently selected from H and C1-C6 alkyl; or R14 and R15, together with the nitrogen atom to which they are both attached, form a 5- or 6-membered ring;
R16 is selected from H and C1-C6 alkyl;
ring A1 and ring A2 are independently selected from phenyl and 5- or 6-membered heteroaryl;
b and c are integers of from 0 to 3;
Q1 is selected from a direct bond, C1-C3 alkylene, C2-C4 alkenylene, and Q13-Y2-Q14;
Q2 is selected from a direct bond and C1-C3 alkylene;
Q3 is selected from a direct bond, C1-C3 alkylene, and C(O);
Q4 is selected from a direct bond, C1-C3 alkylene, and NR17;
Q5 is selected from a direct bond, C1-C3 alkylene, S(O)2NR18, Q15-Y3-Q16, and

each one of Q6, Q7 and Q8 is independently selected from C1-C3 alkylene;
each one of Q9 and Q10 is independently selected from a direct bond and C1-C3 alkylene;
Q11 is selected from a direct bond, C1-C3 alkylene, and C(O);
Q12 is selected from a direct bond, C1-C3 alkylene, and NR19;
Q13 is selected from a direct bond, C1-C3 alkylene, and C1-C3 alkylene substituted by R20 and R21;
each one of Q14, Q15, Q16, Q17 and Q18 is independently selected from a direct bond and C1-C3 alkylene;
each one of R17, R18, and R19 is independently selected from H and C1-C3 alkyl;
R20 and R21 are attached to the same carbon atom and form together with the carbon atom to which they are attached a C3-C6 cycloalkyl;
Y1 is selected from O and S;
Y2 is selected from O, and NR22;
Y3 is selected from O and NR23;
R22 is selected from H, phenyl, and C1-C3 alkyl, which alkyl is optionally substituted by a substituent selected from phenyl and NR24R25;
R23 is H or C1-C3 alkyl; and
R24 and R25 are independently selected from H and C1-C3 alkyl, or R24 and R25 form, together with the nitrogen atom to which they are both attached, a 5- or 6-membered ring;
(ii) R26R27N-Q19, wherein
R26 and R27 are independently selected from H, C1-C6 alkyl and C3-C8 cycloalkyl; or R26 and R27, together with the nitrogen atom to which they are both attached, form a 5- or 6-membered ring optionally substituted by one or more moieties R28;
each R28 is independently selected from R29OC(O)NR30, and

and two R28 attached to adjacent atoms of the ring, together with the atoms to which they are attached, may form a 5- or 6-membered ring;
R29 and R30 are independently selected from H and C1-C6 alkyl;
R31 is selected from C1-C6 alkyl and halogen;
d is an integer of from 0 to 3;
ring A3 is selected from 5- to 10-membered aryl or heteroaryl;
Q19 is a direct bond or C1-C3 alkylene;
Q20 is selected from a direct bond, C1-C3 alkylene and Q21-NR32-Q22;
Q21 and Q22 are independently selected from a direct bond and C1-C3 alkylene; and
R32 is selected from H and C1-C6 alkyl; or
(iv) hydroxy-C1-C6 alkyl;
B1 is O or S;
B2 is N or CR34;
W is N or CR35;
X is N or CR36;
Z is N or CR37;
R34 is H, C1-C3 alkyl or halogen;
R35, R36 and R37 are independently selected from H and F; and
any alkyl, or cycloalkyl is optionally substituted with one or more F;
provided that when Q1 is a direct bond or C1-C3 alkylene, and ring A1 is phenyl, b is not 0; and
provided that the compound is not 2-amino-N-hydroxybenzo[d]thiazole-5-carboxamide.

US Pat. No. 10,654,813

CHEMICAL MOLECULES THAT INHIBIT THE SLICING MECHANISM FOR TREATING DISEASES RESULTING FROM SPLICING ANOMALIES

CENTRE NATIONAL DE LA REC...

and pharmaceutically acceptable salts thereof.

US Pat. No. 10,654,812

PROPELLANE DERIVATES AND SYNTHESIS

Recurium IP Holdings LLC,...

1. A compound having the structure of Formula (I):
wherein:
R1 is —N3, —SCN, —NO, —C(?NOR2)(CN), —CH(?NOR2), CH(CO2H)(NHBoc), —CH(CO2H)(NH2), an optionally substituted cycloalkynyl, an optionally substituted heteroaryl(C1-6 alkyl), an optionally substituted heterocyclyl(C1-6 alkyl), an optionally substituted aminoalkyl or an optionally substituted haloalkoxy; and
R2 is (C1 to C10) alkoxy, an optionally substituted C1-30 alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted cycloalkynyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl, an optionally substituted aryl(alkyl), an optionally substituted heteroaryl(alkyl), an optionally substituted heterocyclyl(alkyl), an optionally substituted aminoalkyl or an optionally substituted alkylamino;
wherein an optionally substituted aminoalkyl is a NH2 group connected, as a substituent, via a lower alkylene group; and
wherein the optionally substituted aminoalkyl is a straight-chained —CH2— tethering group, forming bonds to connect molecular fragments via its terminal carbon atoms and wherein the lower alkylene group can be substituted by replacing one or more hydrogen of the lower alkylene group or by substituting both hydrogens on the same carbon with a cycloalkyl group.

US Pat. No. 10,654,811

HETEROCYCLIC COMPOUNDS FOR CANCER IMAGING AND TREATMENT AND METHODS FOR THEIR USE

The University of British...

1. A compound having the following structure (I):
or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein:
X is —O—, —S(O)0-2—, —C(?O)—, —C(OR5)2—, —C(OR5)(OC(?O)R13)—, —C(R8R9)—, C(?CR8R9)—, —N(R9)—, —N(COR9)—, —CHNR8R9—, —C(?NR9)—, —C(?NOR5)—, or —C(?N—NHR5)—;
R1 is H, hydroxyl, —O-heterocyclyl, or —OC(?O)R13;
R2 is hydroxyl, —O-heterocyclyl, or —OC(?O)R13;
R3 is —N3 or heteroaryl, each R3 is optionally substituted with one or more R6;
R5 is each independently H, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
R6 is each independently selected from the group consisting of H, F, Cl, Br, I, 123I, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, and C6-C12 aryl, wherein each R6 is optionally substituted with one or more of halogen, 123I, 18F, hydroxyl, —OS(O)2-aryl, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
R8 and R9 are each independently H, halogen, —S(O)0-2R5, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, aryl, aralkyl, C1-C10 acyl, or —NR5R5, or R8 and R9 can join to form a unsubstituted or substituted mono-, bi-, or tri-cyclic carbocycle or heterocycle containing from 3 to 20 carbon atoms;
R11a, R11b, R11c, and R11d are each independently H, F, Cl, Br, I, 123I, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, —OR5, —OC(?O)R13, C1-C10 acyl, —S(O)0-2R5, —NO2, —CN, —NH2, —NHR5, or —N(R5)2;
R13 is each independently C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
n1 and n2 are each independently 0, 1, or 2; and
n3 is 0, 1, 2, 3, 4, or 5.

US Pat. No. 10,654,810

INHIBITORS OF LYSINE SPECIFIC DEMETHYLASE-1

CELGENE QUANTICEL RESEARC...

1. A method for treating acute myeloid leukemia (AML), breast cancer, or prostate cancer, in a subject in need thereof comprising administering to the subject a therapeutically effective dose of a compound of Formula (I), or a pharmaceutically acceptable salt thereofwhereinW is N or C—H;
X is hydrogen, halogen, —CN, optionally substituted alkyl, optionally substituted alkynyl, optionally substituted carbocyclylalkynyl, optionally substituted aryl, or optionally substituted heteroaryl;
Y is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted cycloalkylalkyl; and
Z is an optionally substituted group chosen from alkyl, carbocyclyl, C-attached heterocyclyl, N-attached heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, —O-heterocyclyl, —N(R)-heterocyclyl, —O-heterocyclylalkyl, —N(R)-heterocyclylalkyl, —N(R)(C1-C4alkylene)-NR2, or —O(C1-C4alkylene)-NR2; wherein R is hydrogen or C1-C4alkyl.

US Pat. No. 10,654,809

SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF

UNIVERSITY OF TENNESSEE R...

1. A method of treating prostate cancer (PCa) or increasing the survival of a male subject suffering from prostate cancer comprising administering to the subject a therapeutically effective amount of a selective androgen receptor degrader (SARD) compound represented by the structure of formula I:whereinT is OH, OR, OCOR, CH3, —NHCOCH3, or NHCOR;
R1 is CH3, CH2F, CHF2, CF3, CH2CH3, or CF2CF3;
or T and R1 form a 3-8 carbocyclic or heterocyclic ring;
Y is H, CF3, F, I, Br, Cl, CN, or C(R)3;
Z is H, NO2, CN, halide, COOH, COR, NHCOR, CONHR,
or Y and Z form a 5 to 8 membered fused ring;
X is CH or N;
R is H, alkyl, alkenyl, haloalkyl, alcohol, CH2CH2OH, CF3, CH2Cl, CH2CH2Cl, aryl, F, Cl, Br, I, or OH;
A is R2 or R3;
R2 is a five-membered saturated or five or six-membered unsaturated ring having at least one nitrogen atom and 0, 1, or 2 double bonds, optionally substituted with at least one of Q1, Q2, Q3 or Q4, each independently selected from hydrogen, keto, substituted or unsubstituted linear or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, haloalkyl, CF3, substituted or unsubstituted aryl, substituted or unsubstituted phenyl, F, Cl, Br, I, CN, NO2, hydroxyl, alkoxy, OR, benzyl, NCS, maleimide, NHCOOR, N(R)2, NHCOR, CONHR, COOR or COR;
R3 is halide, N3, CF3, COR4, COCl, COOCOR4, COOR4, OCOR4, OCONHR4, NHCOOR4, NHCONHR4, OCOOR4, CN, CONH2, CONH(R4), CON(R4)2, SO3H, SO2NH2, SO2NH(R4), SO2N(R4)2, NH2, CO(N-heterocycle), NO2, cyanate, isocyanate, thiocyanate, isothiocyanate, mesylate, tosylate, triflate, PO(OH)2 or OPO(OH)2; and
R4 is H, alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl, wherein said alkyl, haloalkyl, cycloalkyl, aryl or heteroaryl groups are optionally substituted;
wherein if A is Br or I, R1 is CH3, and T is OH, then X is N or the aniline ring forms a fused heterocyclic ring,
or its isomer, pharmaceutically acceptable salt, pharmaceutical product, hydrate or any combination thereof.

US Pat. No. 10,654,807

TOLL-LIKE RECEPTOR 8 AGONISTS

The University of Kansas,...

1. A pharmaceutical vaccine composition comprising:a vaccine agent;
an adjuvant for the vaccine agent; and
a pharmaceutically acceptable carrier,
wherein the adjuvant comprises a compound comprising:
a structure of Formula 4 or 4A, or salt, stereoisomer, tautomer, polymorph, solvate, or combination thereof:

wherein:
X is S, O, or NH; and
R1 is selected from C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, and combinations thereof;
wherein R1 is optionally substituted by a substituent Q, which substituent Q is selected from C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C1-C24 alkoxy, C2-C24 alkenyloxy, C2-C24 alkynyloxy and combinations thereof; and
wherein the structure is a toll-like receptor 8 agonist.

US Pat. No. 10,654,805

PYRIDINETHIONES, PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR THERAPEUTIC USE FOR TREATING A PROLIFERATIVE, INFLAMMATORY, NEURODEGENERATIVE, OR IMMUNE-MEDIATED DISEASE

BioTheryX, Inc., San Die...

1. A pharmaceutical composition comprising a compound of Formula I:or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, a tautomer, a mixture of two or more tautomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof; and a pharmaceutically acceptable excipient;wherein:R1 is hydrogen or deuterium;
R3 and R5 are each independently (a) hydrogen, deuterium, cyano, halo, or nitro; (b) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl; or (c) —C(O)R1a, —C(O)OR1a, —C(O)NR1bR1c, —C(O)SR1a, —C(NR1a)NR1bR1c, —C(S)R1a, —C(S)OR1a, —C(S)NR1bR1c, —OR1a, —OC(O)R1a, —OC(O)OR1a, —OC(O)NR1bR1c, —OC(O)SR1a, —OC(?NR1a)NR1bR1c, —OC(S)R1a, —OC(S)OR1a, —OC(S)NR1bR1c, —OS(O)R1a, —OS(O)2R1a, —OS(O)NR1bR1c, —OS(O)2NR1bR1c, —NR1bR1c, NR1aC(O)R1d—NR1aC(O)OR1d, —NR1aC(O)NR1bR1c, —NR1aC(O)SR1d, —NR1aC(?NR1d)NR1bR1c, —NR1aC(S)R1d, —NR1aC(S)OR1d, —NR1aC(S)NR1bR1c, —NR1aS(O)R1d, —NR1aS(O)2R1d, —NR1aS(O)NR1bR1c, —NR1aS(O)2NR1bR1c, —SR1a, —S(O)R1a, —S(O)2R1a, —S(O)NR1bR1c, or —S(O)2NR1bR1c;
R4 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
R6 is C5-10 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl; and
each R1a, R1b, R1c, and R1d is independently hydrogen, deuterium, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl; or R1a and R1c together with the C and N atoms to which they are attached form heterocyclyl; or R1b and R1c together with the N atom to which they are attached form heterocyclyl;
wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heteroaryl, and heterocyclyl is optionally substituted with one or more substituents Q, where each Q is independently selected from (a) deuterium, cyano, halo, and nitro; (b) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, and heterocyclyl, each of which is further optionally substituted with one or more substituents Qa; and (c) —C(O)Ra, —C(O)ORa, —C(O)NRbRc, —C(O)SRa, —C(NRa)NRbRc, —C(S)Ra, —C(S)ORa, —C(S)NRbRc, —ORa, —OC(O)Ra, —OC(O)ORa, —OC(O)NRbRc, —OC(O)SRa, —OC(?NRa)NRbRc, —OC(S)Ra, —OC(S)ORa, —OC(S)NRbRc, —OS(O)Ra, —OS(O)2Ra, —OS(O)NRbRc, —OS(O)2NRbRc, —NRbRc, —NRaC(O)Rd, —NRaC(O)ORd, —NRaC(O)NRbRc, —NRaC(O)SRd, —NRaC(?NRd)NRbRc, —NRaC(S)Rd, —NRaC(S)ORd, —NRaC(S)NRbRc, —NRaS(O)Rd, —NRaS(O)2Rd, —NRaS(O)NRbRc, —NRaS(O)2NRbRc, —SRa, —S(O)Ra, —S(O)2Ra, —S(O)NRbRc, and —S(O)2NRbRc, wherein each Ra, Rb, Rc, and Rd is independently (i) hydrogen or deuterium; (ii) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl, each of which is optionally substituted with one or more substituents Qa; or (iii) Rb and Rc together with the N atom to which they are attached form heterocyclyl, optionally substituted with one or more substituents Qa;
wherein each Qa is independently selected from: (a) deuterium, cyano, halo, and nitro; (b) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, and heterocyclyl; and (c) —C(O)Re, —C(O)ORe, —C(O)NRfRg, —C(O)SRe, —C(NRe)NRfRg, —C(S)Re, —C(S)ORe, —C(S)NRfRg, —ORe, —OC(O)Re, —OC(O)ORe, —OC(O)NRfRg, —OC(O)SRe, —OC(?NRe)NRfRg, —OC(S)Re, —OC(S)ORe, —OC(S)NRfRg, —OS(O)Re, —OS(O)2Re, —OS(O)NRfRg, —OS(O)2NRfRg, —NRfRg, —NReC(O)Rh, —NReC(O)ORf, —NReC(O)NRfRg, —NReC(O)SR, —NReC(?NRh)NRfRg, —NReC(S)Rh, —NReC(S)ORf, —NReC(S)NRfRg, —NReS(O)Rh, —NReS(O)2Rh, —NReS(O)NRfRg, —NReS(O)2NRfRg, —SRe, —S(O)Re, —S(O)2Re, —S(O)NRfRg, and —S(O)2NRfRg; wherein each Re, Rf, Rg, and Rh is independently (i) hydrogen or deuterium; (ii) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl; or (iii) Rf and Rg together with the N atom to which they are attached form heterocyclyl.

US Pat. No. 10,654,804

SUBSTITUTED CYCLIC AMIDES AND THEIR USE AS HERBICIDES

FMC Corporation, Philade...

1. A compound of Formula 1, N-oxides and salts thereof:
wherein
Q1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7; or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(?O) and C(?S), and the sulfur atom ring members are independently selected from S(?O)u(?NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members; or
Q1 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl;
Q2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10; or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(?O) and C(?S), and the sulfur atom ring members are independently selected from S(?O)u(?NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10 on carbon atom ring members and selected from R11 on nitrogen atom ring members; or
Q2 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl;
J is —CR2R3—, —NR2a— or —O—;
Y1 and Y2 are each independently O, S or NR12;
R1 is cyano, formyl, C3-C8 alkylcarbonylalkyl, —C(C1-C4 alkyl)=N—O(C1-C4 alkyl), —C(O)NH2, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C4-C8 cycloalkenyl; or arylcarbonyl, arylalkenylalkyl, arylcarbonylalkyl or —CPh=N—O(C1-C4 alkyl), each optionally substituted on ring members with up to 5 substituents independently selected from R13; or G1; or W1G1;
each G1 is independently phenyl, or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R13;
W1 is C1-C3 alkylene, C2-C4 alkenylene, C2-C4 alkynylene, —(C1-C2 alkylene)C(?O)—, —C(?O)(C1-C2 alkylene)-, —CH2O—, —CH2NH—, —OCH2—, —NCH2—, —N—, —O—, —S—, —SO— or —SO2— wherein the free bond projecting to the left indicates the connecting point of W1 to N and the free bond projecting to the right indicates the connecting point of W1 to G1;
R2 and R3 are each independently H, halogen, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy; or
R2 and R3 are taken together with the carbon atom to which they are bonded to form a C3-C7 cycloalkyl ring;
R2a is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C1-C6 alkoxy; or
R1 and R2a are taken together as C3-C6 alkylene or —CH2OCH2—;
R4 and R5 are each independently H, halogen, hydroxy, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl;
R6 is H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl or C3-C10 trialkylsilyl or G1; or
R6 and Q2 are taken together with the nitrogen atom to which they are both bonded to form an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(?O) and C(?S), and the sulfur atom ring members are independently selected from S(?O)u(?NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members;
each R7 and R10 is independently halogen, hydroxy, cyano, nitro, amino, C1-C8 alkyl, C1-C8 cyanoalkyl, C1-C8 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C5-C12 cycloalkylalkenyl, C5-C12 cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C6-C12 cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyalkoxy, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C3-C10 dialkylaminoalkyl, —CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, —C(?O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, —C(?O)NH2, C2-C8 alkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C3-C10 alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C3-C8 cycloalkylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, —SF5, —SCN, SO2NH2, C3-C12 trialkylsilyl, C4-C12 trialkylsilylalkyl or C4-C12 trialkylsilylalkoxy; or G2; or
each R7 is independently R26S(?O)?N—, R26S(?O)2NR25—C(?O)—, R26(R25N=)qS(?O)p—, wherein the free bond projecting to the right indicates the connecting point to Q1; or
each R10 is independently R17ON?CR17a—, (R18)2C?NO—, (R19)2NN?CR17a, (R18)2C?NNR20a—, R20N?CR17a—, (R18)2C?N—, R17ON?CR17aC(R23b)2—, (R18)2C?NOC(R24a)2—, R26S(?O)?N—, R26S(?O)2NR25—C(?O)— or R26(R25N=)qS(?O)p—, wherein the free bond projecting to the right indicates the connecting point to Q2;
each R8 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
each R9 and R11 is independently cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl or C3-C4 dialkylaminoalkyl;
each R12 is independently H, cyano, hydroxy, CHO, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, —(C?O)CH3 or —(C?O)CF3;
each G1 is independently phenyl, or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R13;
each G2 is independently phenyl, phenylmethyl (i.e. benzyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl), phenoxy, phenylethynyl, phenylsulfonyl or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R14;
W1 is C1-C3 alkylene, C2-C4 alkenylene, C2-C4 alkynylene, —(C1-C2 alkylene)C(?O)—, —C(?O)(C1-C2 alkylene)-, —CH2O—, —CH2NH—, —OCH2—, —NCH2—, —N—, —O—, —S—, —SO— or —SO2— wherein the free bond projecting to the left indicates the connecting point of W1 to N and the free bond projecting to the right indicates the connecting point of W1 to G1;
each R13 and R14 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(?O)OH, —C(?O)NH2, —SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl or thienyl;
each R17 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
each R17a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C3-C10 trialkylsilyl or G1;
each R18 is independently H, hydroxy, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
each R19 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
each R20 is independently H, hydroxy, amino, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
each R20a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1;
each R23b is independently H, halogen, cyano, hydroxy, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
each R24a is independently H, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
each R25 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
each R26 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1; and
each u and v are independently 0, 1 or 2 in each instance of S(?O)u(?NR8)v, provided that the sum of u and v is 0, 1 or 2;
each p and q are independently 0, 1 or 2 in each instance of R26(R25N=)qS(?O)p—, provided that the sum of u and v is 0, 1 or 2 and when p is 0, q is other than 1 or 2.

US Pat. No. 10,654,803

TRANSITION METAL-CATALYZED PROTODECARBOXYLATION OF ALPHA-HALO-ACRYLIC ACID DERIVATIVES

Boehringer Ingelheim Inte...

1. A compound selected from the group consisting of
wherein
Rar is selected from the group consisting of C(O)NRN1RN2 and SO2NRN1RN2, wherein RN1 and RN2 are independently selected from the group consisting of H, substituted or unsubstituted C1-6-alkyl and substituted or unsubstituted C3-7-cycloalkyl; and
RY1 and RY2 are independently selected from the group consisting of H, substituted or unsubstituted acetyl, substituted or unsubstituted tert-butyloxycarbonyl (Boc), substituted or unsubstituted carboxybenzyl (Cbz), substituted or unsubstituted fluorenylmethyloxycarbonyl (Fmoc), substituted or unsubstituted allyloxycarbonyl (Alloc), substituted or unsubstituted tert-butyl, substituted or unsubstituted benzyl and substituted or unsubstituted phthaloyl, provided that at least one of RY1 and RY2 is not H, or
RY1 and RY2 are linked to form, together with N to which they are attached, substituted or unsubstituted phthalimide or substituted or unsubstituted pyrrole.

US Pat. No. 10,654,802

INDOLINE DERIVATIVES AND METHOD FOR USING AND PRODUCING THE SAME

Arizona Board of Regents ...

1. A compound of the formula:
wherein
n is an integer from 0 to 4;
each R1 is independently selected from the group consisting of alkyl, haloalkyl, halogen, nitro, heterocycloalkyl, cycloalkyl, optionally substituted heteroaryl, optionally substituted aryl, and —ORa, where each Ra is independently selected from the group consisting of hydrogen, alkyl, heteroaryl, aryl and cycloalkyl; or
two adjacent R1 together with carbon atoms to which they are attached to form heterocycloalkyl;
R2 is selected from the group consisting of:
(a) a moiety of the formula:

(b) a moiety of the formula:

(c) an optionally substituted aryl; and
(d) an optionally substituted heterocycloalkyl,
wherein
m is 1 or 2,
X1 is optionally substituted heterocycloalkyl, —NR4R5, —NRbSO2R6, —NRbC(O)R6, —NRbSO2NR4R5, or —NRbCONR4R5;
X2 is O, NRc or S;
R3 and R3? are each independently hydrogen or alkyl;
each of R4 and R5 is independently hydrogen or alkyl, or R4 and R5 together with the nitrogen atom to which they are attached to form an optionally substituted heterocycloalkyl;
each of Rb and Rc is independently hydrogen or alkyl; and
R6 is —N(Rb)2, optionally substituted aryl, or optionally substituted heterocyclyl;
provided that the compound is not:
N—(N,N-diethylaminosulfonyl)-2-(indolin-1-yl)propane-1-amine);
1,1-diethyl-3-(2-(indolin-1-yl)ethyl)urea;
(N—(N,N-dimethylaminosulfonyl)-2-(indolin-1-yl)ethane-1-amine);
4-(2-(indolin-1-yl)ethyl)morpholine;
1-(2-(piperidin-1-yl)ethyl)indoline;
N-(2-(indolin-1-yl)propyl)morpholine-4-sulfonamide;
N-(2-(indolin-1-yl)propyl)piperidine-1-sulfonamide;
4-fluoro-N-(2-(indolin-1-yl)propyl)benzenesulfonamide;
4-fluoro-N-(2-(indolin-1-yl)ethyl)benzenesulfonamide;
N-(2-(indolin-1-yl)ethyl)-4-methoxybenzenesulfonamide;
3,4-difluoro-N-(2-(indolin-1-yl)propyl)benzenesulfonamide;
N-(2-(indolin-1-yl)propyl)-2,3-dihydrobenzo[b][1,4]dioxine-6-sulfonamide;
N-(2-(indolin-1-yl)ethyl)benzo[d][1,3]dioxole-5-sulfonamide;
N-(2-(indolin-1-yl)ethyl)-2,3-dihydrobenzo[b][1,4]dioxine-6-sulfonamide;
N,N-diethyl-4-(2-(indolin-1-yl)-2-oxoethyl)piperazine-1-sulfonamide;
1-(indolin-1-yl)-2-(4-(morpholinosulfonyl)piperazin-1-yl)ethan-1-one;
1-(indolin-1-yl)-2-(4-(pyrimidin-2-yl)piperazin-1-yl)ethan-1-one;
4-(3-(indolin-1-yl)-3-oxopropyl)-N,N-dimethylpiperazine-1-sulfonamide;
N,N-diethyl-4-(3-(indolin-1-yl)-3-oxopropyl)piperazine-1-sulfonamide;
1-(indolin-1-yl)-3-(4-(morpholinosulfonyl)piperazin-1-yl)propan-1-one;
1-(indolin-1-yl)-3-(4-(pyrimidin-2-yl)piperazin-1-yl)propan-1-one;
2-(cycloheptylamino)-1-(indolin-1-yl)ethan-1-one; or
3-(cycloheptylamino)-1-(indolin-1-yl)propan-1-one.

US Pat. No. 10,654,801

PRODIGIOSIN ANALOGS

Institute For Cancer Rese...

1. A compound of the formula:
wherein R3 is hydrogen, benzyl, n-butyl, n-octyl, or 1-pentyne;
a compound of the formula:

wherein R7 is hydrogen, ethyl, n-butyl, or n-octyl; or
a compound of the formula:

or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,654,800

ANTIDIABETIC COMPOUNDS

KING ABDULAZIZ UNIVERISTY...

1. A method of treating hyperglycemia in a subject in need thereof, comprisingadministering to the subject a therapeutically effective amount of a compound generic structure
where X may be present or absent and is OH, H, CF3, CHF2, CH2F, CN, OR, NHR, NHCOR or NHSO2R, where R?CH3, CH2CH3 and (CH2)2CH3, or where R=cyclopropyl, cyclobutyl, oxetanyl, or oxolanyl;Ar is an aryl group;and n ranges from 0 to 5.

US Pat. No. 10,654,799

ISOTHIOCYANATE FUNCTIONAL SURFACTANTS, FORMULATIONS INCORPORATING ISOTHIOCYANATE FUNCTIONAL SURFACTANTS AND ASSOCIATED METHODS FOR TREATING BIOFILMS

The William M. Yarbrough ...

1. A method for treating a biofilm, comprising the step of:applying an isothiocyanate functional surfactant to a surface having a biofilm, wherein the protonated form of the isothiocyanate functional surfactant is represented by the following chemical structure:
wherein R1 is selected from the group consisting of an alkyl group containing 1 to 25 carbon atom(s); wherein R2 is selected from the group consisting of NCS; and wherein R3-R5 are each independently selected from the group consisting of H; OH; and an alkyl and/or alkanoyl group containing 1 to 25 carbon atom(s) with the proviso that at least one of R3-R5 is selected from the group consisting of an alkyl and/or alkanoyl group containing 8 to 25 carbon atoms.

US Pat. No. 10,654,797

SOLID FORMS OF AN ADAMANTYL COMPOUND, COMPOSITIONS AND USES THEREOF

1. A crystalline form of Compound (I)
selected from
crystalline Form I characterized by an X-ray powder diffraction pattern comprising at least three peaks selected from the peaks expressed as 2? at 7.7±0.2°, 8.9±0.2°, 10.7±0.2°, 13.1±0.2°, 14.2±0.2°, 15.4±0.2°, 18.0±0.2°, 18.7±0.2°, 21.4±0.2°, 21.6±0.2°, 22.4±0.2°, 22.8±0.2°, 23.9±0.2°, 25.5±0.2°, 26.5±0.2°, and 27.0±0.2°, or
crystalline Form II characterized by an X-ray powder diffraction pattern comprising at least three peaks selected from the peaks expressed as 2? at 9.6±0.2°, 13.8±0.2°, 14.7±0.2°, 15.0±0.2°, 16.1±0.2°, 16.8±0.2°, 17.8±0.2°, 18.5±0.2°, 19.0±0.2°, 19.4±0.2°, 20.4±0.2°, 21.7±0.2° and 22.6±0.2°.

US Pat. No. 10,654,796

METHOD FOR PREPARING ALIPHATIC ISOCYANATE

HANWHA CHEMICAL CORPORATI...

1. A method for preparing aliphatic isocyanate, comprising: reacting aliphatic amine or a salt thereof with phosgene in the presence of a compound of the following Chemical Formula 1:
in Chemical Formula 1, R1 to R4 are each independently a C1˜12 hydrocarbyl group,
X is hydrogen, a hydroxyl group, or an acetamido group, and
Y is an oxyl (O?) group or a C1˜20 hydrocarbyloxy group.

US Pat. No. 10,654,794

FUSED TRICYCLIC ?-AMINO ACID DERIVATIVE, PREPARATION METHOD THEREFOR, AND MEDICAL USE THEREOF

SICHUAN HAISO PHARMACEUTI...

1. A compound corresponding to general formula (I), or stereoisomers, solvates, prodrugs, or pharmaceutically acceptable salts thereof,
wherein
R1 and R4 bond each other to form —(CR9R9?)n- or —CR9?CR9?—;
R1?, R2, R3, R3?, R4?, R5, R5?, R6, R9 or R9? is each independently selected from H, F, Cl, Br, I, hydroxyl, amino, carboxy, carboxylate, amide group, cyano, a C1-6 alkyl, a C1-6 alkoxy, a C1-6 sulfanyl, a C2-6 alkenyl, a C2-6 alkynyl, a 3- to 6-membered carbocyclyl or a 3- to 6-membered heterocyclyl, wherein the alkyl, alkoxy, sulfanyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl is optionally further substituted with 0 to 6 substituents selected from F, Cl, Br, I, hydroxyl, amino, carboxy, a C1-6 alkyl, a 3- to 6-membered carbocyclyl or a 3- to 6-membered heterocyclyl, and the heterocyclyl contains 1 to 2 heteroatoms selected from N, O or S;
n is selected from 1, 2 or 3;
alternatively, any pair of R3 and R3?, R5 and R5?, and R9 and R9? forms
together with the carbon atom to which they are attached, and theis optionally further substituted with 0 to 2 substituents selected from F, Cl, Br, I, a C1-6 alkyl, a 3- to 6-membered carbocyclyl or a 3- to 6-membered heterocyclyl, wherein the alkyl, 3- to 6-membered carbocyclyl or 3- to 6-membered heterocyclyl is optionally further substituted with 0 to 6 substituents selected from F, Cl, Br, I, hydroxyl, amino, carboxy, a C1-6 alkyl, a 3- to 6-membered carbocyclyl or a 3- to 6-membered heterocyclyl;alternatively, any pair of R3 and R3?, R5 and R5?, and R9 and R9? forms a 3- to 6-membered carbocycle together with the carbon atom to which they are attached, and the carbocycle is optionally further substituted with 0 to 6 substituents selected from F, Cl, Br, I, hydroxyl, amino, a C1-6 alkyl, a C1-6 alkoxy, or a C1-6 sulfanyl;
R7 is selected from H, a C1-6 alkyl, or an amino-protecting group; and
R8 is selected from H, a C1-6 alkyl, or a carboxy-protecting group.

US Pat. No. 10,654,792

CARBOXYLIC ACID ESTER PRODRUG INHIBITORS OF MEK

DUQUESNE UNIVERSITY OF TH...

1. A method for preparing a compound of structure Ia or structure Ib:
the method comprising a reaction scheme selected from the group consisting of the following:

wherein: X1 is hydrogen, X2 is hydrogen, alkyl, aryl or hetaryl, Y1 is halogen, Z is hydrogen or alkyl, and
Y4 is fluorine, Y5 is iodine, and Y2 and Y3 are hydrogen, or
Y4 and Y5 are hydrogen, and Y2 and Y3 are halogen.

US Pat. No. 10,654,789

CATALYST AND METHOD FOR BIODIESEL PRODUCTION FROM UNREFINED LOW-GRADE OIL AND CRUDE AQUEOUS ALCOHOLS

THE HONG KONG POLYTECHNIC...

1. A method, comprising:using manganese (II) glycerolate, cobalt (II) glycerolate, iron (II) glycerolate, or any combination thereof as a catalyst for catalyzing transesterification of esters or esterification of fatty acids;
wherein the manganese (II) glycerolate has average dimensions of 3.16 ?m×2.38 ?m, the cobalt (II) glycerolate has average dimensions of 6.98 ?m×5.26 ?m, and the iron (II) glycerolate has average dimensions of 0.55 ?m×0.15 ?m.

US Pat. No. 10,654,788

METHOD FOR SYNTHESIZING NOVEL COMPOUNDS DERIVED FROM 3-HYDROXY-CYCLOPENTYL ACETIC ACID

1. A compound having formula (I):
said compound being selecting from the group consisting of:

the optical isomers thereof, diastereoisomers thereof and corresponding salts thereof.

US Pat. No. 10,654,787

PREPARATION AND SEPARATION OF A DI-CARBOXYLIC ACID-CONTAINING MIXTURE

Archer-Daniels-Midland Co...

5. A product comprising an aqueous extract and a separation media comprising a resin in contact with the aqueous extract, the aqueous extract comprising:from about 85 wt. % to about 99 wt. % glucaric acid and any lactones thereof,
gluconic acid and any lactones thereof, wherein the concentration of the gluconic acid and any lactones thereof is less than about 5 wt. %,
from about 0.1 wt. % to about 5 wt. % guluronic acid and any lactones thereof,
less than about 2.5 wt. % of one or more ketogluconic acids and any lactones thereof,
from about 1 wt. % to about 10 wt. % C2-C5 di-acids and any lactones thereof, and
less than about 1 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the product.

US Pat. No. 10,654,786

PROCESS FOR THE PREPARATION OF PURIFIED DICARBOXYLIC ACIDS

NOVAMONT S.P.A., Novara ...

1. A process for the preparation of purified dicarboxylic acids from a mixture containing triglycerides of carboxylic acids having more than one acid functional group comprising the steps of:a) hydrolysing said mixture containing triglycerides in the presence of water, obtaining a reaction product comprising dicarboxylic acids and glycerine;
b) separating out an aqueous phase comprising at least a part of the glycerine from the remaining reaction product from step a) organic phase;
c) evaporating and/or distilling the organic phase obtained from step b), separating out a residue; and
d) recovering at least a part of the dicarboxylic acids from the organic phase evaporated and/or distilled in step c) by means of at least one crystallisation operation, said step comprising the operations of:
d1) extracting the organic phase evaporated and/or distilled in step c) with water in the presence of an organic solvent, obtaining an aqueous phase containing said dicarboxylic acids
d2) crystallising out said dicarboxylic acids from said aqueous phase obtained in step d1), wherein said step d1) comprises at least one counter-current extraction operation.

US Pat. No. 10,654,785

CONVERSION OF CORN OIL TO UPGRADED BIODIESEL AND POLY(LACTIC ACID)

University of Southern Ca...

1. A method extracting embedded hydrogen from glycerol or a compound containing functionalized glycerol, the method comprising:a) combining a glycerol-containing compound with a transition metal catalyst system to form a first composition, the transition metal catalyst system including a first organometallic complex having a transition metal M; and
b) extracting hydrogen gas from the first composition or transferring hydrogen to an unsaturated hydrogen receptor that includes an unsaturated moiety to form a second composition.

US Pat. No. 10,654,780

HALOGENATED NANOHOOP COMPOUNDS AND METHODS OF MAKING AND USING THE SAME

University of Oregon, Eu...

1. A compound selected fromwherein each X independently is chloro, fluoro, bromo, or iodo; and each Y independently is O, S, or NH.

US Pat. No. 10,654,779

SUBSTITUTED BIS(TRIFLUOROVINYL)BENZENE COMPOUND

TOSOH FINECHEM CORPORATIO...

1. A substituted bis(trifluorovinyl)benzene compound represented by general formula (1):
wherein R1, R2, R3, and R4 are each independently a hydrogen, a methyl group, an ethyl group, a linear or branched alkyl group having 3 to 4 carbon atoms, a fluorine-containing alkyl group having 1 to 2 carbon atoms, a fluorine-containing linear or branched alkyl group having 3 to 4 carbon atoms, a fluorine-containing alkenyl group having 2 to 3 carbon atoms, a methoxy group, an ethoxy group, a linear or branched alkoxy group having 3 to 4 carbon atoms, a fluorine-containing alkoxy group having 1 to 2 carbon atoms, a fluorine-containing linear or branched alkoxy group having 3 to 4 carbon atoms, or a halogen atom, provided that R1, R2, R3, and R4 are not all hydrogen; and one or both of ortho positions of the benzene ring to a trifluorovinyl group on the benzene ring is substituted with a methyl group, an ethyl group, a linear or branched alkyl group having 3 to 4 carbon atoms, a fluorine-containing alkyl group having 1 to 2 carbon atoms, a fluorine-containing linear or branched alkyl group having 3 to 4 carbon atoms, a fluorine-containing alkenyl group having 2 to 3 carbon atoms, a methoxy group, an ethoxy group, a linear or branched alkoxy group having 3 to 4 carbon atoms, a fluorine-containing alkoxy group having 1 to 2 carbon atoms, a fluorine-containing linear or branched alkoxy group having 3 to 4 carbon atoms, or a halogen.

US Pat. No. 10,654,776

METHOD FOR AROMATIC FLUORINATION

Dow Global Technologies L...

1. A fluorination method comprising:providing an aryl fluorosulfonate having the following structure to a reaction mixture:
wherein Ar is aryl or heteroaryl;providing a fluorinating reagent to the reaction mixture; and
reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species having the following structure:

US Pat. No. 10,654,774

PROCESSES AND SYSTEMS FOR PURIFICATION OF 1,3-BUTADIENE

SABIC Global Technologies...

1. A system for purifying 1,3-butadiene, comprising:a first distillation column and a second distillation column, each column having a top portion, a bottom portion, and a middle portion;
a first interconnection between the top portion of the first distillation column and the top portion of the second distillation column, wherein the first interconnection is configured to feed a liquid stream from the second distillation column to the first distillation column;
a second interconnection between the bottom portion of the first distillation column and the bottom portion of the second distillation column, wherein the second interconnection is configured to feed a firstgas stream from the second distillation column to the first distillation column;
a top stream line configured to remove a second gas stream from the top portion of the second distillation column, wherein the top stream line is coupled to a heat exchanger;
a vapor outlet line operatively connected to the heat exchanger to recover high volatility componentsfrom the second gas stream;
a feed line forcrude 1,3-butadiene to the first distillation column;
a product outlet line for purified 1,3-butadiene from the second distillation column;
a third interconnection between the top of the first distillation column and the top of the second column to feed a gas stream from the first column to the second column; and
a fourth interconnection between the bottom of the first column to the bottom of the second column to feed liquid from the bottom of the first column to the bottom of the second column;
wherein the second distillation column comprises about 87 theoretical plates; and
wherein the first distillation column has 30 theoretical plates.

US Pat. No. 10,654,773

INTEGRATED FLUID CATALYTIC CRACKING AND OXIDATIVE PROPANE DEHYDROGENATION PROCESS

INDIAN OIL CORPORATION LI...

1. An integrated process for catalytic conversion of alkanes to alkenes, wherein an alkane feed stream from recovery section of fluidized catalytic cracking (FCC) process is converted to respective olefins by catalytic oxidative dehydrogenation (ODH),wherein dehydrogenation of different alkanes occurs simultaneously in separated ODH reactors connected in series or in same ODH reactor with continuous catalyst regeneration; and
wherein oxygen from flue gas exiting from a regenerator of the FCC process is removed in an oxygen separation unit to obtain an oxygen-free flue gas; and
wherein the oxygen-free flue gas is mixed with the alkane feed stream prior to feeding to ODH reactor.

US Pat. No. 10,654,772

SELECTIVE OXIDATIVE DEHYDROGENATION OF PROPANE TO PROPYLENE

UCHICAGO ARGONNE, LLC, C...

1. An efficient method for generating alkenes, the method comprising contacting alkane with catalyst clusters no greater than 30 atoms for a time sufficient to convert the alkane to alkene, wherein the atoms are metal, and wherein conversion occurs thermophoto-chemically with ultraviolet or visible wavelength radiations.

US Pat. No. 10,654,771

SELECTIVE POISONING OF AROMATIZATION CATALYSTS TO INCREASE CATALYST ACTIVITY AND SELECTIVITY

Chevron Phillips Chemical...

1. An aromatization reactor vessel comprising:(i) a reactor wall;
(ii) a catalyst bed positioned within the reactor vessel;
(iii) an outer annulus positioned between the reactor wall and an outer particle barrier, the outer particle barrier and the outer annulus surrounding the catalyst bed;
(iv) a reactor inlet for a feed stream; and
(v) a reactor outlet connected to a center pipe, the center pipe positioned in the reactor vessel and surrounded by the catalyst bed;
wherein the catalyst bed comprises an outer reforming zone and an inner reforming zone, the outer reforming zone comprising a deactivated first aromatization catalyst comprising a first transition metal and a first catalyst support, and the inner reforming zone comprising a second aromatization catalyst comprising a second transition metal and a second catalyst support;
wherein a flow path for the feed stream begins at the reactor inlet; continues to the outer annulus; through the outer particle barrier, the outer reforming zone, and the inner reforming zone; into the center pipe; and to the reactor outlet; and
wherein the deactivated first aromatization catalyst has an aromatics yield of less than 5 wt. %.

US Pat. No. 10,654,770

PRODUCTION OF NEOPENTANE

ExxonMobil Chemical Paten...

1. A process for producing neopentane, the process comprising:(a) providing a feed stream including isobutylene;
(b) dimerizing the isobutylene to produce a dimerization product including diisobutylene; and
(c) demethylating the diisobutylene in a continuous flow, fixed bed reactor at a temperature range of from 250 to 350° C., a hydrogen partial pressure of from about 7 psia to about 113 psia, and in the presence of a catalyst comprising a support material comprising Ni and compounds thereof to produce a demethylation product including at least 10 wt % neopentane based on the weight of the demethylation product; wherein the catalyst further comprises at least one member selected from the group consisting of Cu, Au, Ag, Sn, Zn, Re, combinations thereof, compounds thereof, and mixtures of compounds thereof.

US Pat. No. 10,654,769

CATALYSTS FOR PETROCHEMICAL CATALYSIS

Siluria Technologies, Inc...

1. A catalyst comprising a mixed oxide of a lanthanide and tungsten, wherein the catalyst further comprises a sodium dopant and at least one doping element from groups 2, 4-15, lanthanides or combinations thereof, wherein the catalyst comprises a C2 selectivity of greater than 50% and a methane conversion of greater than 20% when the catalyst is employed as a heterogeneous catalyst in the oxidative coupling of methane at a temperature of 750° C. or less.

US Pat. No. 10,654,768

METHOD FOR RECOVERING ETHYLBENZENE FROM ALKYLATION PRODUCT OF FLUIDIZED CATALYTIC CRACKING OFF-GAS AND BENZENE

SK Innovation Co., Ltd., ...

1. A method for recovering ethylbenzene comprising:reacting a mixture of benzene and fluidized catalytic cracking off-gas comprising ethylene and a light gas in an alkylation reactor to provide a product stream comprising light gas and ethylbenzene;
feeding the product stream to a quencher to separate a quencher overhead stream comprising light gas and a quencher bottom stream comprising benzene and heavier compounds;
feeding the quencher bottom stream to a benzene recovery column to separate a benzene recovery column overhead liquid stream comprising unreacted benzene and a C5-C6 hydrocarbon, a benzene recovery column overhead vapor stream comprising light gas, and a benzene recovery column bottom stream comprising ethylbenzene and heavier compounds; and
feeding the benzene recovery column bottom stream to an ethylbenzene recovery column and recovering ethylbenzene.

US Pat. No. 10,654,765

METHOD FOR PRODUCING A LATENT HEAT STORAGE MATERIAL AND DIALKYL ETHER AS A LATENT HEAT STORAGE MATERIAL

Sasol Germany GmbH, Hamb...

1. A method for the production of a latent heat storage material, comprising:purifying fatty alcohols by distillation in order to obtain by distillation linear fatty alcohols comprising
fatty alcohols that are more than 95% by mass linear,
fatty alcohols that have more than 95% by mass even numbered chain lengths, and
fatty alcohols that have a certain C-number at more than 95% by mass,
followed by dehydrating of the linear fatty alcohols to obtain olefins and subsequently hydrogenating the olefins to obtain paraffins,
wherein the paraffins are the latent heat storage material absorbing heat when liquefying and emitting stored heat when solidifying.

US Pat. No. 10,654,764

PROCESS FOR THE PRODUCTION OF AN ALKYLATED AROMATIC PRODUCT

Johnson Matthey Public Li...

1. A process for the production of an alkylated aromatic product comprising the steps of:a. pyrolysing a pyrolysable raw material comprising lignocellulosic biomass in a pyrolysis process to obtain a pyrolysis product stream containing a phenolic product comprising phenol or a substituted phenol and aromatics products;
b. separating from said pyrolysis product stream a first product stream containing said phenolic product and a second product stream containing said aromatics products;
c. subjecting said first product stream to a hydrogenation reaction to hydrogenate said phenolic product to obtain an aliphatic alcohol;
d. reacting said aliphatic alcohol with said second product stream in the presence of a alkylation catalyst comprising a solid acid catalyst to form an alkylated aromatic product.

US Pat. No. 10,654,763

PROCESS FOR PRODUCING BUTADIENE FROM ETHANOL INTEGRATED WITH EXTRACTIVE DISTILLATION

IFP Energies nouvelles, ...

1. A process for producing butadiene from an ethanol feedstock comprising at least 80% by weight of ethanol, said process comprising:A) converting ethanol in a fraction of the ethanol feedstock into butadiene in at least one reaction section at a pressure between 0.1 and 1.0 MPa and at a temperature between 200° C. and 500° C. in the presence of a catalyst, and producing at least one reaction effluent comprising ethanol, butadiene and impurities, wherein the at least one reaction section is also fed with at least a fraction of an ethanol effluent and/or an ethanol- acetaldehyde effluent that results from step E) of this process;
B) separating the reaction effluent into at least an ethanol-butadiene effluent, an impurities effluent, and a hydrated butadiene effluent;
C) separating said ethanol-butadiene effluent into at least a butadiene distillate and a contaminated reactants residue comprising ethanol and acetalehyde;
D) purifying butadiene in the hydrated butadiene effluent and in the butadiene distillate by the steps comprising:
i) feeding said hydrated butadiene effluent resulting from step B), as a mixture with said butadiene distillate resulting from step C) and with a stream comprising a solvent to a section for separating the butene with extractive distillation to obtain an overhead light gas effluent comprising butene, and a bottoms comprising a butadiene residue, and distilling said butadiene residue into an overhead butadiene distillate and a bottoms comprising a solvent residue;
ii) separating oxygenated compounds from the overhead butadiene distillate by extractive distillation with a stream comprising solvent to produce an overhead comprising prepurified butadiene effluent, and a bottoms comprising spent solvent residue, and distilling said spent solvent residue to separate an overhead oxygenated compounds effluent and a bottoms comprising solvent residue; and
iii) distilling said prepurified butadiene effluent resulting from the separating the oxygenated compounds in D) ii) in a final distillation section to produce an overhead comprising a purified butadiene effluent and a bottoms comprising a 2-butene residue; and
E) treating in an effluent treatment step at least the contaminated reactants residue resulting from step C) and the oxygenated compounds effluent resulting from step D) ii), to produce at least the ethanol effluent, the ethanol-acetaldehyde effluent, and one or more brown oil effluents.

US Pat. No. 10,654,762

ADDITIVE MANUFACTURED COMBUSTIBLE ELEMENT WITH FUEL AND OXIDIZER

Raytheon Company, Waltha...

1. A method of producing a combustible element, the method comprising:successively depositing multiple layers of the element in an additive manufacturing process;
wherein the depositing each of the layers includes depositing a matrix of discrete fuel regions that include a fuel material, and discrete oxidizer regions that include an oxidizer material, for that layer.

US Pat. No. 10,654,761

PYROTECHNICS CONTAINING OLEORESIN

Safariland, LLC, Jackson...

1. A pyrotechnic composition comprising:a fuel;
an oxidizer;
flow and rate control agents; and
oleoresin capsicum.

US Pat. No. 10,654,760

SOLVENT SYSTEMS FOR DICYANDIAMIDE AND/OR ALKYL THIOPHOSPHORIC TRIAMIDE AND USE IN AGRICULTURAL APPLICATIONS

RHODIA OPERATIONS, Paris...

18. A method of making an aqueous end use fertilizer composition comprising contacting one or more nitrogenous fertilizer compounds with an inhibitor composition, the inhibitor composition consisting of:N-(n-butyl)-thiophosphoric triamide dispersed in a liquid medium,
the liquid medium consisting of:
at least one organophosphate solvent of formula (VIII):

wherein R1, R2 and R3, are each independently chosen from a C1-C4 alkyl group, and
dimethylsulfoxide;
optionally, dicyandiamide,
optionally, water;
optionally, a dye; and
optionally a co-solvent selected from the group consisting of
at least one dibasic ester selected from the group consisting of di(C1-C12)alkyl esters of saturated linear or branched (C2-C8)aliphatic dicarboxylic acids and mixtures thereof;
at least one compound of formula (IIa):
R3OOC-A-CONR4R6  (IIa),
wherein R3 comprises a C1-C36 alkyl group; wherein R4 and R5 individually comprise a C1-C36 alkyl group, wherein R4 and R5 can optionally together form a ring; and wherein A is a linear or a branched divalent C2-C6 alkyl group;
at least one alkyldimethylamide;
ethyl levulinate; and
at least one alkylene carbonate;
wherein the N-butyl thiophosphoric triamide is 30 to 60 wt %, by total weight of the inhibitor composition,
wherein for 100 parts by weight total N-butyl thiophosphoric triamide, organophosphate solvent and dimethylsulfoxide there is greater than 40 up to 60 parts N-butyl thiophosphoric triamide.

US Pat. No. 10,654,759

SYSTEM AND METHODS FOR ADDITION OF BENEFICIAL AGRICULTURAL, BIOLOGICAL, AND/OR DEDUSTING ADDITIVES TO GRANULAR FERTILIZERS

The Mosaic Company, Plym...

16. A method for conditioning inorganic phosphate fertilizer granules for improved dust control, agricultural benefits, or both, the method comprising:providing a plurality of inorganic phosphate fertilizer granules in a conditioning vessel, the granules having a surface temperature of about 50° F. to about 250° F.;
introducing a quantity of an aqueous conditioning agent into the conditioning vessel in an amount of about 0.1 wt % to about 10 wt % of the total weight of the inorganic phosphate fertilizer granules;
subjecting the inorganic phosphate fertilizer granules with the aqueous conditioning agent thereon to a mechanical energy exposure by mixing or tumbling the inorganic phosphate fertilizer granules in the conditioning vessel to promote particle to particle interaction; and
removing moisture from the inorganic phosphate fertilizer granules until a final moisture content of the fertilizer granules is 0 wt % to about 6.5 wt % of the granules,
wherein the aqueous conditioning agent consists of water.

US Pat. No. 10,654,758

UREA AMMONIUM NITRATE PRODUCTION

Stamicarbon B.V., Sittar...

16. A method of modifying an existing plant, wherein the existing plant comprises an ammonium nitrate section, a urea production unit, an off-gas treatment section, and an urea ammonium nitrate section,wherein the ammonium nitrate section is configured for reacting ammonia and nitric acid under ammonium nitrate forming conditions and is in fluid communication with a source of nitric acid and a source of ammonia and has an outlet for aqueous ammonium nitrate solution and an outlet for first off-gas,
wherein the urea production unit comprises a finishing section adapted to solidify a urea liquid, wherein the finishing section has a gas outlet for second ammonia-containing off-gas,
wherein the off-gas treatment section has a gas inlet in fluid communication with said gas outlet for second off-gas of said finishing section, adapted to subject said second ammonia-containing off-gas of the finishing section to treatment with an acidic scrubbing liquid,
wherein the urea ammonium nitrate section comprises a unit having an inlet in fluid connection with said outlet for aqueous ammonium nitrate solution and an inlet for receiving urea liquid, for combining said ammonium nitrate solution and said urea liquid, and having an outlet for urea ammonium nitrate solution,
wherein the method comprises adding a connection for fluid communication between said outlet for first off-gas from said ammonium nitrate section and a gas inlet of said off-gas treatment section.

US Pat. No. 10,654,756

FORMULATIONS FOR ENGINEERED CERAMIC MATRIX COMPOSITES FOR HIGH TEMPERATURE APPLICATIONS

United States of America ...

1. A process for fabricating engineered ceramic matrix composites (E-CMCs) for high temperature applications, comprising:combining and attrition milling a mixture of silicon carbide (SiC), silicon nitride, and a component selected from the group consisting of CrMoSi, CrMoSiGe, and CrMoSiY;
wet attrition milling the mixture using ethanol and silicon carbide grinding media, grinding the mixture into particles and homogenously mixing the mixture;
slurry preparing the mixture to generate an engineered CMC slurry;
infiltrating a preform with the engineered CMC slurry either under gravity, vacuum, or high pressure to allow particulates to spread uniformly within cavities of the preform; and
melt infiltrating the preform with CrSi2, CrSi, Cr5Si3, or any combination thereof to fill in voids left behind after the slurry infiltration.

US Pat. No. 10,654,755

OUTER PERIPHERAL COATING MEMBER AND CERAMIC PRODUCT

DENSO CORPORATION, Kariy...

1. An outer peripheral coating member comprising:first particles containing titanium oxide;
second particles containing zirconium oxide;
third particles containing niobium oxide or aluminum oxide; and
a dispersion medium, wherein:
the first particles have not less than two different peak values R1 in a distribution of particle size thereof, and
one of the peak values R1 of the particle sizes of the first particles is within a range of 1 to 50 nm, and the other peak value R1 is within a range of 100 to 500 nm.

US Pat. No. 10,654,752

ASPHALT CRACK FILLING SYSTEM AND METHOD OF USE

1. A method of repairing a crack in an asphalt surface, comprising:adding a predetermined amount of crack filler material to a crack filler preparation receptacle, the crack filler material comprising at least one of asphalt cement, aggregate, polymers, petroleum extracts, polyester fiber, and solvents;
adding, based on the predetermined amount of crack filler added to the crack filler preparation receptacle, a predetermined amount of silane additive to the crack filler preparation receptacle, the silane additive comprising organosilane and benzyl alcohol;
mixing the crack filler material and silane additive together in the crack filler preparation receptacle under heat for a period of time forming an enhanced crack filler substance, wherein an amount of the benzyl alcohol in the silane additive forms the enhanced crack filler substance into a liquid;
dispensing the enhanced crack filler substance into the crack in the asphalt surface; and
curing the dispensed enhanced crack filler substance.

US Pat. No. 10,654,751

POLYMER MODIFIED CEMENT ADHESIVE FOR PROVIDING HIGH FRICTION SURFACING

1. A thin dry polymer modified cement adhesive overlay on a trafficked pavement substrate that enables a plurality of vehicles to traverse thereover on a consistent basis, wherein the trafficked pavement substrate can be either a concrete surface or an asphalt surface, the thin dry polymer modified cement adhesive overlay comprisinga dry polymer modified cement mixture including Portland cement, polymer powders and ultrafine aggregate, wherein the ultrafine aggregate has a finer granularity than aggregate typically used with cement such as the aggregate defined in ASTM C144 specification; and
water, wherein when the dry polymer modified cement mixture is mixed with the water it creates a dry polymer modified cement adhesive that is applied directly to the trafficked pavement substrate as a thin layer to create the thin dry polymer modified cement adhesive overlay on the trafficked pavement substrate.

US Pat. No. 10,654,749

SOLAR CONTROL COATINGS PROVIDING INCREASED ABSORPTION OR TINT

Vitro Flat Glass LLC, Ch...

1. A coated article having a tinted appearance in reflection and/or transmission, comprising:a substrate; and
a solar control coating, wherein the solar control coating consists of:
a first dielectric layer;
a subcritical metallic layer having discontinuous metallic regions and having a thickness in a range of 5 ? to 50 ?, wherein the subcritical metallic layer consists of silver; and
a second dielectric layer over the subcritical metallic layer.

US Pat. No. 10,654,748

SOLAR CONTROL COATINGS PROVIDING INCREASED ABSORPTION OR TINT

Vitro Flat Glass LLC, Ch...

1. A coated article having a tinted appearance inreflection and/or transmission, consisting of:
a substrate;
a first dielectric layer;
a subcritical metallic layer having discontinuous metallic regions and having a thickness in a range of 5 ? to 50 ?; and
a second dielectric layer over the subcritical metallic layer;
wherein the subcritical metallic layer consists of silver.

US Pat. No. 10,654,747

SOLAR CONTROL COATINGS WITH SUBCRITICAL COPPER

Vitro Flat Glass LLC, Ch...

1. A coated article having a tinted appearance in reflection and/or transmission, comprising:a substrate;
a first dielectric layer;
a subcritical metallic layer having discontinuous metallic regions and having a thickness less than 90 ?, wherein the subcritical metallic layer consists of copper; and
a second dielectric layer over the subcritical metallic layer.

US Pat. No. 10,654,746

GLASS PLATE WITH ANTIREFLECTION FILM

AGC Inc., Chiyoda-ku (JP...

1. An antireflective glass sheet comprising:a glass sheet;
a first transparent high refractive index layer positioned on the glass sheet, the first transparent high refractive index layer being composed of a titanium oxide doped with a zirconium oxide, and having a first refractive index;
a first transparent low refractive index layer positioned on the first transparent high refractive index layer, the first transparent low refractive index layer being composed of a silicon oxide or a silicon oxide doped with a zirconium oxide, and having a second refractive index;
a second transparent high refractive index layer positioned on the first transparent low refractive index layer, the second transparent high refractive index layer being composed of a titanium oxide or a titanium oxide doped with a zirconium oxide, and having a third refractive index; and
a second transparent low refractive index layer positioned on the second transparent high refractive index layer, the second transparent low refractive index layer being composed of a silicon oxide or a silicon oxide doped with a zirconium oxide, and having a fourth refractive index,
the second refractive index being lower than the first refractive index and the third refractive index,
the fourth refractive index being lower than the first refractive index and the third refractive index,
the antireflective glass sheet having a haze after heating at 600° C. to 700° C. for 15 minutes being 0.4% or less, and having a visible light reflectance measured from a side of the second transparent low refractive index layer based on JIS R 3106 being 1.0% or less, and
the second transparent low refractive index layer having an average hydrogen concentration Cav, of less than 10 atom %,
wherein the average hydrogen concentration Cav obtained by forming a carbon film having a thickness of 5 nm on the second transparent low refractive index layer, measuring hydrogen concentrations at a depth range of 15 nm to 20 nm from a surface of the second transparent low refractive index layer at a portion where the carbon film is formed by a high resolution ERDA method, and averaging the obtained hydrogen concentrations to obtain the average hydrogen concentration Cav.

US Pat. No. 10,654,745

HIGH-EXPANSION BONDING GLASS HAVING IMPROVED WATER RESISTANCE AND USES THEREOF

Schott AG, Mainz (DE)


wherein R oxide is an oxide selected from the group consisting of MnO2, SiO2, SnO2, Ta2O5, Nb2O5, Fe2O3, GeO2, CaO, and combinations thereof, the composition being free of PbO except for, at most, impurities.

US Pat. No. 10,654,743

BURNER HEAD ACTUATOR FOR LUBRICATING GLASSWARE MOLDS OF A GLASSWARE FORMING MACHINE

Owens-Brockway Glass Cont...

1. A burner head actuator for lubricating glassware molds of a glassware forming machine, comprising:a base mount;
a guide post carried by the base mount and having a longitudinally extending guide post axis;
a gearbox having a housing carried on the guide post and a gear train carried by the housing and including a drive gear and a driven gear;
a servomotor coupled to the gearbox; and
a burner head arm carried by the gearbox housing and coupled to the driven gear for rotation relative to the gearbox housing about an arm axis, the arm including a burner head leveling gear train including a drive sprocket direct-driven by the driven gear about the arm axis and a driven sprocket driven by the drive sprocket via a chain;
wherein the servomotor actuates the gearbox to rotate the gearbox drive gear, thereby rotating the gearbox driven gear and the burner head arm, and thereby rotating the leveling gear train so that the burner head remains level as the arm is rotated about the arm axis.

US Pat. No. 10,654,742

METHOD FOR TEMPERING GLASS PLATE, AND TEMPERED GLASS PLATE

AGC Inc., Chiyoda-ku (JP...

1. A tempered glass plate made of glass with a single matrix composition and having a first main surface and a second main surface opposed to each other,wherein the tempered glass plate has a compressive stress layer at its surface, and
wherein in the distribution of stress remaining in a cross section passing through the center of the first main surface and being perpendicular to the first main surface, a depth from the first main surface where the compressive stress component in a direction parallel to the first main surface becomes zero, is at least 22% of a plate thickness of the tempered glass plate.

US Pat. No. 10,654,741

METHOD FOR PRODUCING A GLASS TUBE WITH A CROSS SECTION OF A NONCIRCULAR FORM BY RESHAPING

SCHOTT AG, Mainz (DE)

1. Method for producing a glass tube with a cross section of a noncircular form by reshaping, comprising at least the steps of:providing a glass tube having a longitudinal axis and an outer surface,
heating the glass tube, providing at least one reshaping tool having an interior, which has a forming body with a forming area for reshaping the heated glass tube, the forming body comprising at least one open-porous material,
setting a gas pressure in the interior of the at least one reshaping tool that is lower than 90 kPa, so that a negative pressure is produced on the forming area of the forming body, and
reshaping the heated glass tube by applying a compressive force perpendicularly to the longitudinal axis of the glass tube, the compressive force being generated by the at least one reshaping tool and being applied to the outer surface of the glass tube,
characterized in that the glass tube has an aspect ratio of a cross section, and the aspect ratio after the reshaping is greater than the aspect ratio before the reshaping.

US Pat. No. 10,654,740

SUBMERGED COMBUSTION BURNERS, MELTERS, AND METHODS OF USE

Johns Manville, Denver, ...

1. A fluid-cooled submerged combustion burner comprising:a burner body (6) comprising an external conduit (10) and a first internal conduit (12) substantially concentric therewith, and positioned internal of the external conduit (10), the external conduit (10) comprising a first end, a second end, and a longitudinal bore having a longitudinal axis, the first internal conduit (12) comprising a first end, a second end, and a longitudinal bore having a longitudinal axis, the external conduit (10) and first internal conduit (12) forming a first annulus (11) for passing a cooling fluid there between, and a second internal conduit (14) substantially concentric with, and positioned internal of the first internal conduit (12), the second internal conduit (14) comprising a first end, a second end, and a longitudinal bore having a longitudinal axis, and configured to form a second annulus (13) between the first and second internal conduits (12, 14), and a central, concentric conduit (15) comprising a first end and a second end and configured to form a third annulus (19) between the second internal conduit (14) and the central, concentric conduit (15), the burner body comprising fuel and oxidant inlet ports near the second ends of the conduits; and
a burner tip (4) defined by a right cylindrical inner wall (28) and a right cylindrical outer wall (30) connected via a curvilinear crown (32), the right cylindrical outer wall (30) removably fixed to the first end of the external conduit (10) via an outer connection, and the right cylindrical inner wall (28) removably fixed to the first end of the second internal conduit (14) via an inner connection, the burner tip (4) comprising a generally central flow passage configured to pass a combustible mixture therethrough, the generally central flow passage defined by the right cylindrical inner wall (28);
wherein the burner tip crown (32) and right cylindrical inner and outer walls (28, 30) comprise the same or different corrosion resistant and fatigue resistant material, at least one of the corrosion and/or fatigue resistance being greater than material comprising the external conduit (10) under conditions experienced during submerged combustion melting of glass-forming materials, and the burner body (6) and burner tip (4) are configured with the first end of the central, concentric conduit (15) recessed from the curvilinear crown (32) such that flow of oxidant or fuel out of the third annulus (19) and flow of fuel or oxidant out of the central, concentric conduit (15) causes the fuel and oxidant to intersect and mix sufficiently in a mixing region (150) to combust at least some of the fuel in the mixing region (150) and to form the combustible mixture and a flame in the mixing region (150) in the generally central flow passage defined by the right cylindrical inner wall (28) and a diverging portion of the curvilinear crown (32) downstream of the right cylindrical inner wall (28).

US Pat. No. 10,654,739

METHODS AND SYSTEMS FOR PROCESSING DREDGE SPOILS

Dredge Spoils Reclamation...

1. A method for processing dredge spoils, comprising:filtering dredge spoils in filtration equipment;
receiving dredge spoils from the filtration equipment in a land based mobile feed tank;
pumping the dredge spoils from the land based mobile feed tank to an agitation tank;
agitating the dredge spoils in the agitation tank;
pumping the dredge spoils from the agitation tank to a dewatering system, wherein the dredge spoils are dewatered to generate dewatered dredge spoils;
grinding the dewatered dredge spoils in a grinder; and
mixing an additional material with the dewatered dredge spoils to produce a reclaimed soil selected from a group consisting of topsoil, compost, and bedding soil, wherein the additional material comprises sand and an organic additive.

US Pat. No. 10,654,738

APPARATUS FOR SALT SEPARATION UNDER SUPERCRITICAL WATER CONDITIONS

Ecole Polytechnique Foder...

1. An apparatus for salt separation from an aqueous liquefied stream under supercritical water conditions, comprising:a fluidized bed reactor including:
a fluidized bed chamber defined by a supercritical water pressure containing wall, and containing a fluidized bed therein;
an inlet system at one end of said fluidized bed reactor, said inlet system including an inlet in fluid communication with an inlet chamber and a fluidization plate positioned between the inlet chamber and the fluidized bed chamber;
an outlet system to separate solids from supercritical fluid at the other end of said fluidized bed reactor and spaced from the fluidized bed chamber;
wherein the fluidized bed chamber extends between the inlet system and outlet system and comprises an entry section adjacent the inlet system, an outlet section adjacent the outlet system, and a mid-section extending between the entry section and the outlet section; and
a heat exchanger extending through the fluidized bed chamber and comprising, in operation, a decreasing temperature gradient in the fluidized bed chamber from the outlet section to the inlet section, the temperature gradient in the outlet section and mid -section being supercritical for aqueous substances and being subcritical for aqueous substances in at least a first portion of the entry section adjacent the fluidization plate; and
wherein an aqueous liquefied stream is introduced into the inlet chamber, passes through said fluidization plate for treatment in the fluidized bed chamber, and solid particles in supercritical fluid exiting the fluidized bed chamber are removed by the outlet system.

US Pat. No. 10,654,737

SYSTEMS AND PROCESSES FOR TREATMENT OF HIGH TOTAL DISSOLVED SOLIDS WASTEWATER

SIEMENS ENERGY, INC., Or...

1. A treatment process for wastewater comprising a chemical oxygen demand (COD) concentration and a total dissolved solids (TDS) concentration of at least about 10 g/L therein, the process comprising:subjecting the wastewater to wet air oxidation to remove an amount of COD from the wastewater and generate a first treated stream comprising a first reduced COD concentration relative to the wastewater and the TDS concentration of at least about 10 g/L; and
subjecting the first treated stream to a biological process comprising contacting the first treated stream with an amount of biomass and powdered activated carbon, to generate a second treated stream comprising at least a second reduced COD concentration relative to the first treated stream.

US Pat. No. 10,654,736

COMPACT WATER PURIFICATION UNIT

Stonehouse Water Technolo...

1. A water purification unit apparatus, comprising:at least one unit inlet and at least one unit outlet;
a plurality of sump cylinders, each of the plurality of sump cylinders comprising:
a cylinder base, a cylinder top, and a cylinder cap, the cylinder cap removably extending into the cylinder top,
at least one of a removable filter or a treatment lamp extending within the interior of the sump cylinder,
wherein each of the plurality of sump cylinders comprises at least one cylinder inlet and at least one cylinder outlet, the at least one cylinder inlet being located at a height below the cylinder cap, the at least one cylinder outlet being located at a height above the at least one cylinder inlet,
wherein the at least one cylinder inlet of each of the plurality of sump cylinders is in fluid communication with either another of the plurality of sump cylinders or the at least one unit inlet,
wherein each of the at least one cylinder outlet of each of the plurality of sump cylinders is in fluid communication with either another of the plurality of sump cylinders or the at least one unit outlet;
at least one cylinder connector forming a fluid path between one of the plurality of sump cylinders and another of the plurality of sump cylinders; and
a controller in communication with at least one of the plurality of sump cylinders and at least one sensor, the controller comprising a unit power supply and a control processor.

US Pat. No. 10,654,735

METHOD OF COMBINING RECUPERATIVE DIGESTION WITH A CONTACT TANK AND DISSOLVED AIR FLOTATION

Evoqua Water Technologies...

1. A wastewater treatment system comprising:a contact tank having a first inlet configured to receive wastewater to be treated, a second inlet configured to receive activated sludge, and an outlet, the contact tank being configured to mix the wastewater to be treated with the activated sludge to form a first mixed liquor;
a dissolved aft flotation unit having an inlet in fluid communication with the outlet of the contact tank, the dissolved air flotation unit being configured to separate suspended matter from a portion of the first mixed liquor to form a solids-lean dissolved air flotation unit effluent and floated solids, to output the floated solids through a solids outlet of the dissolved aft flotation unit, and to output the solids-lean dissolved aft flotation unit effluent through an effluent outlet of the dissolved air flotation unit;
a biological treatment unit having a first inlet in fluid communication with the effluent outlet of the dissolved air flotation unit and an outlet, the biological treatment unit being configured to biologically break down organic components of the effluent from the dissolved aft flotation unit to form a second mixed liquor;
a dissolved aft flotation unit effluent conduit extending between the effluent outlet of the dissolved aft flotation unit and the first inlet of the biological treatment unit; an anaerobic digester having an inlet and an outlet;
a floated solids conduit providing fluid communication between the solids outlet of the dissolved aft flotation unit and the inlet of the anaerobic digester;
a thickener having an inlet in fluid communication with the outlet of the anaerobic digester, a first outlet in fluid communication with the inlet of the anaerobic digester, and a second outlet, the thickener being configured to receive a portion of a digested solids stream from the outlet of the anaerobic digester, remove liquid from the portion of the digested solids stream to produce a thickened digested solids stream having an increased solids content relative to that of the portion of the digested solids stream, output the removed liquid from the second outlet, and return the thickened digested solids stream to the inlet of the anaerobic digester; and
a second thickener having an inlet in fluid communication with the outlet of the anaerobic digester downstream of the thickener, the second thickener configured to receive a second portion of the digested solids stream from the outlet of the anaerobic digester and to remove liquid from the second portion of the digested solids stream to produce a dewatered digested solids stream having an increased solids content relative to that of the second portion of the digested solids stream.

US Pat. No. 10,654,734

PROCESS AND DEVICE FOR TREATING WASTEWATERS BY OXIDATION

SUEZ INTERNATIONAL, Pari...

1. A wastewater treatment process comprising at least one step of aerobic biological treatment of wastewater in a biological reactor (3), and a step during which ozone is directly injected and without an ozone contactor in one or more circuits (1, 6) arranged to convey a respective fluid into the biological reactor (3), the ozone chemical oxidation acting synergistically with the biological oxidation within the biological reactor, without an ozone contactor.