US Pat. No. 10,113,233

MULTI-ZONE TEMPERATURE CONTROL FOR SEMICONDUCTOR WAFER

Taiwan Semiconductor Manu...

1. An apparatus, comprising: a controller programmed to receive a plurality of measurements of a critical dimension (CD) at respective locations in a circuit pattern etched from a film comprising a film material on a first semiconductor substrate; and a single wafer chamber for forming a second film of the film material on a second semiconductor substrate, wherein a first film material is deposited on the first semiconductor substrate by the single wafer chamber, the single wafer chamber being responsive to a control signal from the controller to adjust a thickness of the second film at one or more of the respective locations based on the plurality of measurements of the CD, wherein the single wafer chamber has a platen that supports the second semiconductor substrate, and wherein the single wafer chamber includes a plurality of heating elements, wherein each of the plurality of heating elements is moveable with respect to the platen; and a plurality of driver units, wherein a single driver unit is coupled to one respective heating element to independently actuate said one respective heating element in a plane parallel to a wafer-engaging surface of the platen, wherein each single driver unit is configured to move one respective heating element in two orthogonal directions in the plane parallel to the wafer-engaging surface of the platen, and wherein each single driver unit is configured to provide independent adjustments to positions of one respective heating element.

US Pat. No. 10,113,231

PROCESS KIT INCLUDING FLOW ISOLATOR RING

APPLIED MATERIALS, INC., ...

1. A process chamber comprising:a sidewall;
a substrate support having an outer ledge;
a gas inlet beneath the substrate support;
a first liner having an annular inner surface separated from the outer ledge of the substrate support by a first gap, the first liner further having an outer angled surface; and
a flow isolator ring having an inner bottom surface configured to be disposed on the outer ledge of the substrate support when the substrate support is in a raised position and an outer bottom surface extending outwardly relative to the inner bottom surface, the outer bottom surface overlying the first gap, wherein the flow isolator ring further comprises:
a top surface located inwardly relative to an outer edge of the outer bottom surface; and
an outer angled surface between the top surface and the outer bottom surface, the outer angled surface oriented inwardly towards the top surface, wherein
the outer bottom surface of the flow isolator ring is configured to be disposed on the first liner when the substrate support is in a lowered position, and
the outer angled surface of the flow isolator ring and the outer angled surface of the first liner are configured to be collinear when the substrate support is in the lowered position.

US Pat. No. 10,113,230

FORMATION METHOD OF HEXAGONAL BORON NITRIDE THICK FILM ON A SUBSTRATE AND HEXAGONAL BORON NITRIDE THICK FILM LAMINATES THEREBY

KOREA INSTITUTE OF SCIENC...

1. A method of forming a multilayer hexagonal boron nitride (h-BN) thick film on a substrate, the method comprising:(a) a substrate heating step of heating a first substrate comprising iron (Fe);
(b) a h-BN precursor supply step of supplying h-BN precursors comprising borazine (H3B3N3H3) to the heated first substrate;
(c) a precursor dissolving step of dissolving the supplied h-BN precursors in the first substrate;
(d) a substrate cooling step of cooling the first substrate containing the dissolved h-BN precursors therein; and
(e) a formation step of multilayer h-BN thick film on a surface of the first substrate from the dissolved h-BN precursors therein.

US Pat. No. 10,113,229

TECHNIQUES FOR CONTROLLING ION/NEUTRAL RATIO OF A PLASMA SOURCE

Varian Semiconductor Equi...

20. A method for increasing a ratio of reactive ions to a neutral species, the method comprising:providing a processing apparatus comprising:
a plasma source chamber including a first gas inlet delivering a first gas; and
a deposition chamber coupled to the plasma source chamber, the deposition chamber including a second gas inlet and a third gas inlet delivering a point of use (POU) gas to an area proximate a substrate disposed within the deposition chamber, wherein the POU gas is different than the first gas, wherein the POU gas is delivered from the second gas inlet and from the third inlet on opposite sides of the first gas, and wherein the POU gas is delivered from the second gas inlet and from the third gas inlet in a same direction orthogonal to the substrate;
increasing a pressure within the deposition chamber in an area proximate the substrate to increase an amount of reactive ions present for impacting the substrate when an ion beam is delivered to the substrate, wherein the pressure is increased by optimizing each of the following: a gas flow rate of a first inlet of the plasma source chamber, a gas flow rate of at least one gas inlet of the first and second inlets of the deposition chamber, a distance between the substrate and the plasma source chamber, a pump speed of a deposition chamber pump fluidly connected with the deposition chamber, and a pump speed of a plasma source chamber pump fluidly connected with the plasma source chamber; and
generating the ion beam for delivery to the substrate, wherein the increase in pressure in the area proximate the substrate increases a ratio of reactive ions to neutral species impacting the substrate when the ion beam is delivered to the substrate, and wherein the ion beam is delivered to the substrate at a non-perpendicular angle relative to the substrate.

US Pat. No. 10,113,228

METHOD FOR CONTROLLING SEMICONDUCTOR DEPOSITION OPERATION

TAIWAN SEMICONDUCTOR MANU...

1. A method for controlling a semiconductor deposition operation, comprising:identify a normalized full service target lifetime according to off-line measurements;
identifying a first target lifetime by a controller in a physical vapor deposition (PVD) system, the first target lifetime being identified at about 0.43 of the normalized full service target lifetime;
inputting the first target lifetime into a processor;
outputting, by the processor, a reactive gas flow rate according to a segment corresponding to the first target lifetime of a compensation curve, the compensation curve being predetermined and stored in a memory device of the controller; and
tuning the reactive gas flow rate in the PVD system so as to achieve an atomic ratio of target material and reactive gas of a deposited layer close to unity at the first target lifetime.

US Pat. No. 10,113,227

CRUCIBLE

BOE TECHNOLOGY GROUP CO.,...

1. A crucible, comprising a main cavity, wherein the crucible further comprises a plurality of sub-cavities which are arranged in the main cavity and are used for containing solid evaporation material, each of the sub-cavities being provided with an opening,wherein between any two adjacent sub-cavities, a conduit for mutual communication between said two adjacent sub-cavities is arranged and a through hole is formed on a side wall of each of the two adjacent sub-cavities at a position that connects the through hole with the conduit,
wherein the through hole penetrates a side of each of the two adjacent sub-cavities at a position below the respective opening,
wherein the conduit is detachably fixed to the side wall of each of the two adjacent sub-cavities by a connecting device,
wherein the conduit is made of a same material as the main cavity and the sub-cavities, and
wherein a switch shutter is provided on the side wall of each of the two adjacent sub-cavities and aligned with the through hole formed on each of the two adjacent sub-cavities.

US Pat. No. 10,113,226

SPALLATION-RESISTANT THERMAL BARRIER COATING

United Technologies Corpo...

1. A coated article comprising:a metallic substrate (22);
a bondcoat (30) comprising:
a first layer (32); and
a second layer (34), the first layer being between the second layer and the metallic substrate and having a lower Cr content than the second layer; and
a thermal barrier coating (TBC) (28),wherein by weight percent:the bondcoat second layer comprises 20-40 Cr, up to 30 Co, 5-13 Al, up to 2 Y, up to 2 Si, and up to 2 Hf, balance Ni with less than 2.0 individually and less than 5.0 aggregate other elements, if any; and
the bondcoat first layer comprises 1.0-30 Cr, up to 30 Co, 3-35 Al, 0.1-2 Y, 0.1-2 Hf, 0.1-7 Si, up to 8 Ta, up to 8 W, up to 2 Mo, and up to 2 Zr, balance Ni with less than 2.0 individually and less than 5.0 aggregate other elements, if any.

US Pat. No. 10,113,225

MASKANT FOR USE IN ALUMINIZING A TURBINE COMPONENT

Howmet Corporation, Whit...

1. A mask for preventing aluminizing of a region of a component made of a superalloy, comprising a mixture of chromium-containing powder, nickel-containing powder and refractory powder wherein the chromium-containing powder comprises metallic chromium powder or chromium-containing metal alloy powder, the chromium-containing powder being present in the mixture in an amount greater than about 10 weight % effective (a) to supply chromium to form a chromium-enriched surface on the superalloy component beneath the mask during aluminizing of an unmasked region or (b) to supply chromium to a pre-existing chromium-enriched chromized surface on the superalloy component beneath the mask to retain the chromium-enriched chromized surface during aluminizing of an unmasked region.

US Pat. No. 10,113,224

FRICTION ADJUSTMENT INTERFACE BETWEEN TWO PARTS MADE OF NICKEL OR NICKEL OR COBALT-CHROMIUM ALLOY THAT ARE IN RELATIVE MOTION AGAINST ONE ANOTHER AT HIGH TEMPERATURE

Airbus Operations (S.A.S....

1. An adjustment interface inserted between a first part made of nickel, a nickel alloy or a cobalt-chromium alloy that is in relative motion with a second part made of nickel, a nickel alloy or a cobalt-chromium alloy, wherein the adjustment interface comprises two adjustment layers comprising:a first adjustment layer deposited on the first part of the two parts and having a composition that makes it possible, with the friction with the second part, to create a glaze-type layer;
a second adjustment layer deposited on the second part for cooperation with the first adjustment layer by acting as a catalyst for an oxide formed by friction with the first adjustment layer.

US Pat. No. 10,113,223

HOT-DIP GALVANIZED STEEL SHEET

1. A hot-dip galvanized steel sheet comprising:a steel sheet; and
a hot-dip galvanized layer formed on at least one surface of the steel sheet,
the steel sheet includes:
a chemical composition comprising, % by mass:
C: 0.040% to 0.280%,
Si: 0.05% to 2.00%,
Mn: 0.50% to 3.50%,
P: 0.0001% to 0.1000%,
S: 0.0001% to 0.0100%,
Al: 0.001% to 1.500%,
N: 0.0001% to 0.0100%,
O: 0.0001% to 0.0100%, and
a remainder of Fe and impurities;
wherein in a range of ? thickness to ? thickness centered at a position of ¼ thickness from the surface of the steel sheet, by volume fraction, said steel sheet includes:
0 to 50% of a ferrite phase,
a total of 50% or more of a hard structure comprising one or more of a bainite structure, a bainitic ferrite phase, a fresh martensite phase and a tempered martensite phase,
a residual austenite phase is 0 to 8%, and
a total of a pearlite phase and a coarse cementite phase is 0 to 8%,
wherein in a surface layer range of 20 ?m depth in a steel sheet direction from an interface between the hot-dip galvanized layer and a base steel, said steel sheet includes:
a residual austenite is 0 to 3%,
wherein the base steel sheet includes:
a microstructure in which V1/V2 which is a ratio of a volume fraction V1 of the hard structure in the surface layer range and a volume fraction V2 of the hard structure in the range of ? thickness to ? thickness centered at the position of ¼ thickness from the surface of the base steel sheet is limited within a range of 0.10 or more and 0.90 or less,
a Fe content is 5.0% or less and an Al content is 1.0% or less in the hot-dip galvanized layer, and columnar grains formed of a ? phase are included, and further
a ratio ((A*/A)×100) of an interface (A*) between the ? phase and the base steel sheet in an entire interface (A) between the hot-dip galvanized plated layer and the base steel sheet is 20% or more, and
a refined layer is formed at the side of the interface in the base steel sheet, wherein an average thickness of the refined layer is 0.1 to 5.0 ?m, an average grain size of ferrite in the refined layer is 0.1 to 3.0 ?m, one or two or more of oxides of Si and Mn are contained, and a maximum size of the oxide is 0.01 to 0.4 ?m.

US Pat. No. 10,113,221

BEARING STEEL

AKTIEBOLAGET SKF, Gothen...

1. A method of heat treating a bearing component composed of a steel alloy composition that comprises:0.6 to 0.7 wt. % carbon,
1.3 to 1.7 wt. % silicon,
1.2 to 1.6 wt. % manganese,
0.8 to 1.2 wt. % chromium,
0.15 to 0.4 wt. % molybdenum,
0.05 to 0.25 wt. % nickel,
0.003 to 0.01 wt. % vanadium,
0.005 to 0.05 wt. % aluminium,
0.05 to 0.3 wt. % copper,
0 to 0.5 wt. % cobalt,
0 to 0.1 wt. % niobium,
0 to 0.1 wt. % tantalum,
0 to 150 ppm nitrogen, and
0 to 50 ppm calcium,
the balance being iron and 0.3 wt. % or less of unavoidable impurities,
the method comprising:
(i) heating the steel alloy composition at a temperature of 865-900° C. for 50-100 minutes to at least partially austenitise the composition;
(ii) quenching the steel alloy composition to a temperature of 190-210° C. and holding the steel alloy composition at the temperature of 190-210° C. for 12-36 hours;
(iii) isothermally heating the steel alloy composition at a temperature of 200-280° C. until the steel alloy composition has a microstructure that comprises 5 to 10 vol.% retained austenite and at least 80 vol. % bainitic-ferrite and has a Vickers hardness of at least 650 HV; and
(iv) subjecting the bearing component having 5 to 10 vol.% retained austenite and at least 80 vol. % bainitic-ferrite to a surface finishing technique.

US Pat. No. 10,113,216

QUASICRYSTAL AND ALUMINA MIXED PARTICULATE REINFORCED MAGNESIUM-BASED COMPOSITE MATERIAL AND METHOD FOR MANUFACTURING THE SAME

NORTH UNIVERSITY OF CHINA...

1. A quasicrystal and alumina mixture particles reinforced magnesium matrix composite comprising:a quasicrystal and alumina mixture particles reinforcement phase; and
a magnesium alloy matrix;
the weight ratio of the quasicrystal and alumina mixture particles reinforcement phase to the magnesium alloy matrix being (4-8) to 100,
the magnesium alloy matrix comprising by weight 1000 parts of magnesium, 90 parts of aluminum, 10 parts of zinc, 1.5-5 parts of manganese, 0.5-1 part of silicon and 0.1-0.5 part of calcium, and
the quasicrystal and alumina mixture particles reinforcement phase comprising by weight 40 parts of magnesium, 50-60 parts of zinc, 5-10 parts of yttrium and 8-20 parts of nanometer alumina particles of which the diameter is 20-30 nm.

US Pat. No. 10,113,215

MAKING MINERAL SALTS FROM VARIOUS SOURCES

LIXIVIA, INC., Santa Bar...

1. A mixture utilized in lixiviant extraction of a metal hydroxide forming species from a raw material comprising:a raw material comprising an insoluble metal salt, wherein the insoluble metal salt comprises the metal hydroxide forming species; and
a lixiviant solution comprising an organic amine cation and a counterion,
wherein the lixiviant solution is formulated to transfer the counterion to the insoluble metal salt to form an uncharged organic amine, and wherein the uncharged organic amine is formulated to react with an acid to regenerate the organic amine cation, and
wherein the organic amine cation is present in a substoichiometric amount relative to the insoluble metal salt.

US Pat. No. 10,113,214

ALKALI METAL AND/OR ALKALI EARTH METAL EXTRACTION METHOD

AISIN SEIKI KABUSHIKI KAI...

1. A method for extracting at least one of an alkali metal and an alkali earth metal from a solid containing at least one of the alkali metal and the alkali earth metal, the method comprisingadding the solid to a neutral amino acid-containing aqueous solution so as to elute at least one of the alkali metal and the alkali earth metal in the neutral amino acid-containing aqueous solution,
contacting an acidic gas with the eluted at least one of the alkali metal and the alkali earth metal in the neutral amino acid-containing aqueous solution to precipitate the at least one of the alkali metal and the alkali earth metal as a salt,
recovering the salt,
adding another solid containing at least one of an alkali metal and an alkali earth metal to the neutral amino acid-containing aqueous solution from which the salt was recovered to elute at least one of the alkali metal and the alkali earth metal in the neutral amino acid-containing aqueous solution, and
determining a mixing ratio of water, the neutral amino acid and the solid so that peak values of a rate of elution and an amount of the salt precipitated are matched, the rate of elution being obtained by dividing an amount of the at least one of the alkali metal and the alkali earth metal eluted in the neutral amino acid-containing aqueous solution by an amount of the at least one of the alkali metal and the alkali earth metal contained in the solid, or an integrated value of the rate of elution and the amount of the salt precipitated is maximized,
wherein the neutral amino acid-containing aqueous solution has an isoelectric point within a range of ±1.5 with respect to a first acid dissociation constant of the acidic gas, and the neutral amino acid is DL-alanine and is a chelating agent that reacts with at least one of the alkali metal and the alkali earth metal to form a chelated complex.

US Pat. No. 10,113,211

METHOD OF MAKING A DUAL HARDNESS STEEL ARTICLE

ATI PROPERTIES LLC, Alba...

1. A method of manufacturing a dual hardness steel article, comprising:providing a first air hardenable steel alloy part comprising a first mating surface and having a first part hardness;
providing a second air hardenable steel alloy part comprising a second mating surface and having a second part hardness, wherein the first part hardness is greater than the second part hardness;
disposing the first air hardenable steel alloy part and the second air hardenable steel alloy part so that at least a portion of the first mating surface contacts at least a portion of the second mating surface;
metallurgically securing the first air hardenable steel alloy part to the second air hardenable steel alloy to form a metallurgically secured assembly;
hot rolling the metallurgically secured assembly to form a metallurgical bond between the first mating surface and the second mating surface; and
cooling the hot rolled assembly.

US Pat. No. 10,113,210

HEAT TREATMENT APPARATUS FOR CYLINDER BLOCK AND HEAT TREATMENT METHOD FOR CYLINDER BLOCK

TOYOTA JIDOSHA KABUSHIKI ...

1. A heat treatment apparatus for a cylinder block, the heat treatment apparatus performing heat treatment by feeding gas, the heat treatment apparatus comprising:a first feed part configured to feed the gas toward bores of the cylinder block, from a first side or a second side of the bores in an axis direction of the bores; and
a second feed part configured to feed the gas toward a lateral surface of the cylinder block from the first side or the second side, the lateral surface of the cylinder block extending in an array direction of the bores,
wherein the first feed part includes a first feed hole that is a jet orifice for the gas,
wherein the second feed part includes a second feed hole that is a jet orifice for the gas, and
wherein at least one of the first feed hole and the second feed hole is a slit along the array direction of the bores of the cylinder block.

US Pat. No. 10,113,209

METHODS AND SYSTEMS FOR PRODUCING HIGH CARBON CONTENT METALLIC IRON USING COKE OVEN GAS

MIDREX TECHNOLOGIES, INC....

1. A method for producing high carbon content metallic iron using coke oven gas, comprising:dividing a top gas stream from a direct reduction shaft furnace into a first top gas stream and a second top gas stream;
treating a coke oven gas stream from a coke oven gas source in one or more guard vessels to remove liquid droplets, aerosols, and heavy hydrocarbons from the coke oven gas stream;
mixing the first top gas stream with the treated coke oven gas stream and processing at least a portion of a resulting combined gas stream in a selective separation unit to form a synthesis gas-rich gas stream and a carbon-dioxide rich gas stream;
delivering the synthesis gas-rich gas stream to the direct reduction shaft furnace as bustle gas;
using the carbon-dioxide rich gas stream as fuel gas in one or more heating units;
delivering the second top gas stream to the direct reduction shaft furnace as bustle gas; and
delivering at least a portion of the coke oven gas stream to the direct reduction shaft furnace as a transition zone gas stream at a temperature that is lower than a temperature of the bustle gas.

US Pat. No. 10,113,195

NUCLEIC ACID AMPLIFICATION

LIFE TECHNOLOGIES CORPORA...

1. A method for amplifying a plurality of nucleic acid templates, comprising:a) providing a plurality of forward primers immobilized on a support, wherein the plurality of forward primers includes a first forward primer and a second forward primer, and wherein the plurality of forward primers have substantially identical sequences;
b) providing a nucleic acid reverse strand from the plurality of nucleic acid templates, having a forward primer-binding sequence that can hybridize to any one of the plurality of forward primers;
c) hybridizing the first forward primer to the forward primer-binding sequence on the nucleic acid reverse strand;
d) generating an extended forward strand that is substantially complementary to the nucleic acid reverse strand and is hybridized thereto, by primer extension of the first forward primer using the reverse strand as a template, wherein the first forward primer becomes incorporated into the extended forward strand;
e) denaturing at least a portion of the extended forward strand comprising the incorporated first forward primer and the forward primer-binding sequence on the nucleic acid reverse strand and hybridizing the second forward primer to the forward primer-binding sequence on the nucleic acid reverse strand;
f) generating another extended forward strand that is substantially complementary to the reverse strand and is hybridized thereto, by primer extension of the second forward primer using the reverse strand as a template, wherein the second forward primer becomes incorporated into the extended forward strand; and
g) amplifying the plurality of nucleic acid templates simultaneously in a single continuous liquid phase without first compartmentalizing, by performing one or more amplification cycles comprising steps (e)-(f) under isothermal conditions to form clonal or substantially clonal nucleic acid populations, wherein the incorporated second forward primer of step (e) of an amplification cycle acts as the incorporated first forward primer of step (e) of a subsequent amplification cycle and the second forward primer of step (e) in the subsequent amplification cycle is a new second forward primer that has not undergone primer extension; and wherein the amplifying is carried out using a recombinase and a polymerase.

US Pat. No. 10,113,194

GAS TESTING UNIT AND METHOD

LANZATECH NEW ZEALAND LIM...

1. A method comprising:(a) evaluating suitability of a test C1-containing substrate obtained from an industrial process for use in a biological conversion process comprising:
(b) providing a gas testing unit, comprising:
(i) a first bioreactor stage for evaluating the performance of a reference C1-containing substrate;
(ii) a second bioreactor stage for evaluating the performance of the test C1-containing substrate;
(iii) an analytical section configured for analysis of both gaseous and liquid products of the first and second bioreactors;
wherein the gas testing unit is capable of being housed within a container having a volume of less than about 6 m3 and transportable to multiple locations;
(c) feeding the reference C1-containing substrate to the first bioreactor of the gas testing unit containing a first culture of a C1-fixing microorganism the first bioreactor operated at a set of target operating conditions;
(d) feeding the test C1-containing substrate obtained from the industrial process to the second bioreactor of the gas testing unit containing a second culture of the C1-fixing microorganism, the second bioreactor operated at the same set of target conditions as the first bioreactor;
(e) analyzing both gaseous and liquid products of the first and second bioreactors employing the analytical section of the gas testing unit to determine the performance of the first and second bioreactors; and
(f) comparing the performance of the first bioreactor, relative to the performance of the second bioreactor to determine the suitability of the test C1-containing substrate obtained from the industrial source for use in a biological conversion process;
the process characterized in that it is carried out at a site of the industrial process.

US Pat. No. 10,113,189

ISOLATION AND CHARACTERIZATION OF A NOVEL PYTHIUM OMEGA 3 DESATURASE WITH SPECIFICITY TO ALL OMEGA 6 FATTY ACIDS LONGER THAN 18 CARBON CHAINS

BASF Plant Science GmbH, ...

1. A method for the manufacture of a composition comprising a compound having a structure of the general formula I:
wherein
R1=hydroxyl, coenzyme A (thioester), lysophosphatidylcholine, lysophosphatidylethanolamine, lysopho sphatidylglycerol, lysodipho sphatidylglycerol, lysopho sphatidylserine, lysophosphatidylinositol, sphingo base or a radical of the formula II:

R2=hydrogen, lysophosphatidylcholine, lysophosphatidylethanolamine, lysopho sphatidylglycerol, lysodipho sphatidylglycerol, lysopho sphatidylserine, lysophosphatidylinositol or saturated or unsaturated C2-C24-alkylcarbonyl, R3=hydrogen, saturated or unsaturated C2-C24-alkylcarbonyl, or R2 and R3 independently of each other are a radical of the formula Ia:

n=2, 3, 4, 5, 6, 7 or 9, m=2, 3, 4, 5 or 6 and p=0 or 3;
and
wherein said method comprises cultivating a host cell or a transgenic non-human organism comprising a polynucleotide comprising a heterologous nucleic acid sequence selected from the group consisting of:
(i) the nucleic acid sequence of SEQ ID NO: 1 or 23;
(ii) a nucleic acid sequence encoding a polypeptide comprising the amino acid sequence of SEQ ID NO: 2 or 24; and
(iii) a nucleic acid sequence encoding a polypeptide having omega-3 desaturase activity capable of converting omega-6 DPA into DHA, wherein said polypeptide has at least 95% sequence identity to the amino acid sequence of SEQ ID NO: 2 or 24,
under conditions which allow biosynthesis of said compound.

US Pat. No. 10,113,185

UTILIZATION OF PHOSPHOKETOLASE IN THE PRODUCTION OF MEVALONATE, ISOPRENOID PRECURSORS, AND ISOPRENE

Danisco US Inc., Palo Al...

1. Recombinant microbial cells capable of producing isoprene, wherein the cells comprise (a) one or more heterologous nucleic acids encoding a polypeptide having phosphoketolase activity; (b) attenuated activity of an acetate kinase enzyme by (i) deletion of an endogenous acetate kinase gene; or (ii) replacement of an endogenous promoter of the endogenous acetate kinase gene with a synthetic constitutively low-expressing promoter; (c) one or more nucleic acids encoding one or more polypeptides of the complete MVA pathway; and (d) a heterologous nucleic acid encoding an isoprene synthase polypeptide, wherein culturing of said recombinant cells in a suitable media provides for the production of isoprene, and wherein the production of isoprene is increased relative to cells that do not comprise the one or more heterologous nucleic acids encoding a polypeptide having phosphoketolase activity.

US Pat. No. 10,113,164

PICHIA PASTORIS SURFACE DISPLAY SYSTEM

Research Corporation Tech...

1. A surface display system comprising:(a) an engineered strain of Pichia pastoris comprising a mutant ?-1,6-mannosyltransferase (OCH1) allele which is transcribed into a mRNA coding for a mutant OCH1 protein, wherein the mutant OCH1 protein comprises a catalytic domain at least 95% identical with amino acids 45-404 of SEQ ID NO: 2, wherein the mutant OCH1 protein lacks an N-terminal sequence for targeting the mutant OCH1 protein to the Golgi apparatus and lacks a membrane anchor domain at the N-terminal region, and wherein said strain produce substantially homogeneous N-glycans; and
(b) a vector encoding a recombinant protein adapted to be displayed on a surface of the Pichia pastoris.

US Pat. No. 10,113,160

CARBON DIOXIDE FIXATION VIA BYPASSING FEEDBACK REGULATION

Easel Biotechnologies, LL...

1. A method for improving the efficiency of carbon dioxide fixation in an organism having a Calvin-Benson-Bassham (CBB) cycle, comprising:genetically modifying the organism having the CBB cycle to produce or overexpress a first enzyme, and to produce or overexpress a second enzyme;
wherein the first enzyme is phosphoketolase enzyme, belonging to EC 4.1.2.9 and the second enzyme is phosphoribulokinase enzyme belonging to EC 2.7.1.19;
wherein the first enzyme utilizes an intermediate of the CBB pathway as a substrate and generates a first acetyl phosphate product;
wherein the phosphoribulokinase enzyme is produced or overexpressed in an amount to achieve a phosphoribulokinase activity level that is higher than the native phosphoribulokinase activity level of the organism;
wherein the second enzyme is overexpressed in the genetically modified organism in an amount to achieve a phosphoribulokinase activity level that is higher than the native phosphoribulokinase activity level of the organism, and the second enzyme utilizes ribulose-5-phosphate to produce ribulose-1,5-bisphosphate;
wherein the first acetyl phosphate product is converted in the organism to acetyl-CoA;
wherein the genetically modified organism fixes two CO2 molecules onto two of the ribulose-1,5-bisphosphate molecules, and the reaction products are then turned over in the CBB cycle to produce one acetyl-CoA molecule from the first acetyl phosphate, when the organism is grown in culture at ammonium levels of less than 3 mM; and
wherein the production of phosphoenolpyruvate (PEP) in the genetically modified organism, when grown under nitrogen depletion, is below a feedback inhibitory concentration for the CBB cycle.

US Pat. No. 10,113,153

P450-BM3 VARIANTS WITH IMPROVED ACTIVITY

Codexis, Inc., Redwood C...

1. A recombinant polynucleotide sequence encoding a recombinant cytochrome P450-BM3 variant, wherein said sequence comprises SEQ ID NO: 3, and further wherein said recombinant cytochromie P450-BM3 variant oxidizes at least three organic substrates.

US Pat. No. 10,113,152

VARIANT POLYPEPTIDES CAPABLE OF AMINATING ALIPHATIC ALPHA KETO ACIDS

AbbVie Inc., North Chica...

1. A polypeptide, comprising:(a) the amino acid sequence of any one of SEQ ID NOS:2 and 13-18, wherein X is not leucine;
(b) an amino acid sequence that is at least 95% identical to: (i) amino acids 6 to 238 of SEQ ID NO:2; (ii) amino acids 7 to 237 of SEQ ID NO:13; (iii) amino acids 4 to 236 of SEQ ID NO:14; (iv) amino acids 4 to 236 of SEQ ID NO:15; (v) amino acids 4 to 236 of SEQ ID NO:16; (vi) amino acids 4 to 236 of SEQ ID NO:17; or (vii) amino acids 4 to 236 of SEQ ID NO:18, wherein X is not leucine;
(c) an amino acid sequence that is at least 95% identical to: (i) amino acids 6 to 298 of SEQ ID NO:2; (ii) amino acids 7 to 297 of SEQ ID NO:13; (iii) amino acids 4 to 296 of SEQ ID NO:14; (iv) amino acids 4 to 296 of SEQ ID NO:15; (v) amino acids 4 to 296 of SEQ ID NO:16; (vi) amino acids 4 to 296 of SEQ ID NO:17; or (vii) amino acids 4 to 296 of SEQ ID NO:18, wherein X is not leucine; or
(d) the amino acid sequence of SEQ ID NO: 4, 5, 6, or 20;
wherein the polypeptide is isolated and wherein the polypeptide has the ability to convert 2-oxonon-8-enoic acid, in the presence of an ammonia source, to 2-aminonon-8-enoic acid; and
X is isoleucine, valine, glycine, alanine, serine, or threonine.

US Pat. No. 10,113,151

COMPOSITION OF VIRAL VECTORS IN LECITHIN LIPOSOMES, PREPARATION METHOD AND TREATMENT METHODS

The Regents of the Univer...

1. A method of preparing a formulation comprising a viral particle encapsulated in an anionic liposome, wherein the viral particle is a recombinant adenovirus, the method comprising:a) preparing a mixture by dissolving lecithin, cholesterol and PEG in an organic solvent;
b) drying the mixture under vacuum to form a dry lipid film;
c) mixing the dried lipid film with recombinant adenovirus particles and hydrating the dried lipid film by exposing it to a physiological solution, and thereby forming multilamellar vesicles;
d) sonicating said vesicles and thereby forming a formulation with recombinant adenovirus particles encapsulated in the anionic liposomes;
e) binding non-encapsulated recombinant adenovirus particles with an antibody; and
f) separating the encapsulated recombinant adenovirus particles from the non-encapsulated recombinant adenovirus particles bound to the antibody by magnetic immunoprecipitation with magnetic beads linked to protein G; and thereby extracting the non-encapsulated recombinant adenovirus particles from the formulation.

US Pat. No. 10,113,145

PAENIBACILLUS SP. STRAIN, CULTIVATION METHOD AND USE OF THE SAME

1. An extracellular polysaccharide of Paenibacillus, wherein the structural formula of the extracellular polysaccharide shown in Formula (1),
wherein, n=15-30;
wherein the extracellular polysaccharide is purified and free of non-carbohydrate structure including protein, sulfide and amidogen;
wherein the extracellular polysaccharide has an average molecular weight distribution of 2500 to 5000 Da; and/or has following appearance: pure white filament or powder; wherein the extracellular polysaccharide is produced by Paenibacillus bovis sp. nov. BD3526 whose deposit number is CGMCC No. 8333.

US Pat. No. 10,113,144

METHOD FOR PRODUCING CELL CONCENTRATE, AND CELL SUSPENSION TREATMENT SYSTEM

KANEKA CORPORATION, Osak...

1. A method for producing a cell concentrate using a cell suspension treatment system including:a storage container of a cell suspension, which has a solution inlet port, a circulation outlet port, and a circulation inlet port;
a cell suspension treatment device for concentrating the cell suspension by separating liquid from the cell suspension by filtration, the device including a container having a cell suspension introduction port, a cell suspension lead-out port, and a filtrate outlet, which is filled with a hollow fiber separation membrane,
a circulation circuit for concentrating the cell suspension while circulating the cell suspension between the storage container and the cell suspension treatment device, the circuit being constituted by an introduction communication tube communicating the circulation inlet port of the storage container and the cell suspension introduction port of the cell suspension treatment device and a lead-out communication tube communicating the cell suspension lead-out port of the cell suspension treatment device and the circulation outlet port of the storage container;
a collection container of a cell concentrate obtained by concentration;
a collection path for feeding the cell concentrate in the storage container, the cell suspension treatment device, and the circulation circuit to the collection container;
an injection path for injecting a solution into the solution inlet port of the storage container;
a detecting unit for detecting a volume of the cell concentrate in the storage container or the introduction communication tube of the circulation circuit, and
an air bubble sensor on a path from the storage container to an air filter, wherein the air filter is provided above the storage container so as to make a pressure of an inner portion of the storage container to an atmospheric pressure,
the method comprising:
a) a step of storing the cell suspension in the storage container by supplying the cell suspension to the storage container through the solution inlet port;
b) a step of concentrating the cell suspension by feeding the cell suspension in the storage container to the cell suspension treatment device through the introduction communication tube of the circulation circuit, and then, circulating the cell suspension into the storage container through the lead-out communication tube of the circulation circuit;
c) a step of terminating the step b) by detecting the volume of the cell concentrate in the storage container or the introduction communication tube of the circulation circuit; and
d) a step of feeding and collecting the cell concentrate in the storage container, the cell suspension treatment device, and the circulation circuit to the collection container through the collection path.

US Pat. No. 10,113,143

CELL CULTURE BAG AND METHOD FOR MANUFACTURING CELL CULTURE BAG

Yokogawa Electric Corpora...

1. A cell culture bag comprising:an external film;
at least one sensor chip arranged on an inner surface of the external film, the at least one sensor chip including a layer reacting to an object to be detected, the inner surface being on a culture fluid side of the external film; and
a permeable film that covers a culture fluid side of the sensor chip, the permeable film permeating the object to be detected,
wherein the permeable film covers the entire inner surface of the external film,
wherein the at least one sensor chip comprises a plurality of sensor chips arranged into a plurality of groups,
wherein a group of sensor chips having the largest size is arranged at the center of the plurality of groups, the remaining groups of sensor chips having a smaller size being arranged around the group of sensor chips having the largest size, and
wherein the group of sensor chips having the largest size is configured to generate a stronger signal than the remaining groups of sensor chips having a smaller size.

US Pat. No. 10,113,142

METHOD AND APPARATUS FOR MAKING SOAP

DESIGNED BY M.E., LLC, B...

1. A method for making soap comprising:piercing, upon closure of a lid of an apparatus, a lye capsule in a lye container;
combining, in a first mixing vessel, a portion of water from a water vessel with a portion of lye from the lye capsule to form a first mixture;
cooling, in the first mixing vessel, the first mixture to a first predetermined temperature;
combining, in an oil vessel, two or more oils to dissolve into a second mixture;
heating, in the oil vessel, the second mixture to a second predetermined temperature to produce a heated second mixture;
adding, in the oil vessel, a third oil to the heated second mixture;
cooling, in the oil vessel, the heated second mixture to a third predetermined temperature to produce a cooled second mixture;
combining, in a second mixing vessel, the first mixture and the cooled second mixture to form a third mixture; and
discharging the third mixture from the second mixing vessel into one or more soap molds to form one or more bars of soap.

US Pat. No. 10,113,141

CLEANING LIQUID FOR SEMICONDUCTOR DEVICE AND METHOD FOR CLEANING SUBSTRATE FOR SEMICONDUCTOR DEVICE

MITSUBISHI CHEMICAL CORPO...

1. A cleaning liquid for a semiconductor device, comprising the following components (1)? to (4)?:(1)? an inorganic alkali;
(2)? a carboxyl group-containing chelating agent, which is at least one amino acid selected from the group consisting of cysteine and histidine;
(3)? an anionic surfactant which is at least one of a benzenesulfonic acid substituted with an alkyl group having from 8 to 20 carbon atoms and a salt thereof; and
(4)? water,
wherein the cleaning liquid has a pH of 9 or more.

US Pat. No. 10,113,136

FRACTIONATION OF FRANKINCENSE RESIN USING SUPERCRITICAL CARBON DIOXIDE

PHYTOVATION LTD, Gwynedd...

1. A method for sequentially extracting essential oil, incensole derivatives and boswellic acid from frankincense resin, said method comprising:a) grinding the frankincense resin;
b) separating a first fraction of essential oil with liquid carbon dioxide at a first temperature ranging between 0° C. and 30° C. and a first pressure ranging between 40 bars and 73.8 bars or with mild supercritical carbon dioxide, and with a first flow rate ranging between 10 g and 400 g/kg ground material/min until no further essential oil can be recovered or the extract yield falls below 0.1% of starting mass per hour;
c) retrieving essential oil from the separator;
d) separating a second fraction of incensole derivatives with supercritical carbon dioxide at a second temperature ranging between 31° C. and 100° C. and a second pressure of at least 72.8 bars and a second flow rate ranging between 10 g and 400 g/kg ground material/min until no further incensole or its derivatives can be recovered or the extract yield falls below 0.1% of starting mass per hour;
e) retrieving incensole derivatives from the separator;
f) optionally, continuing the separation process with supercritical carbon dioxide at other sets of increasing temperature and/or pressure until further desired fractions are separated;
g) separating a further fraction of boswellic acid with supercritical carbon dioxide at a temperature of at least 31° C. and a pressure of at least 72.8 bars and a flow rate ranging between 10 g and 400 g/kg ground material/min using a co-solvent at a level ranging between 0.05 vol % and 50.0 vol % of the CO2 flowrate until complete separation of boswellic acids is achieved or it is determined that no further materials can be extracted or the extract yield falls below 0.1% of starting mass per hour;
h) retrieving boswellic acid from the separator and removing the co-solvent by evaporation or distillation;
i) optionally, continuing the separation process with supercritical carbon dioxide at another set of temperature and pressure and co-solvent until all desired fractions are separated; and
j) retrieving the remaining unseparated residues.

US Pat. No. 10,113,133

RANDOM COPOLYMERS OF ACRYLATES AS POLYMERIC FRICTION MODIFIERS, AND LUBRICANTS CONTAINING SAME

AFTON CHEMICAL CORPORATIO...

1. A random copolymer obtained from polymerizing an acrylate monomer composition, wherein the monomer composition comprises:a) from about 5 to about 55 mole % of at least one short chain acrylate of Formula (I),
in which Ra is hydrogen or methyl, and R1 is a linear or branched C1 to C10 alkyl radical;b) from about 0 to less than about 75 mole % of at least one long chain acrylate of Formula (II),
in which Rb is hydrogen or methyl, and R2 is a linear or branched C11 to C15 alkyl radical;c) from about 0 to less than about 75 mole % of at least one long chain acrylate of Formula (III),
in which Rc is hydrogen or methyl, and R3 is a linear or branched C16 to C30 alkyl radical; andd) from about 5 to about 50 mole % of at least one polar acrylate of Formula (IV),
in which Rd is hydrogen or methyl, A is a linear or branched C2 to C6 alkyl radical, aromatic radical, or a polyether of the formula (—CHR4CH2—O—)n where R4 is hydrogen or methyl and n is from 1 to 10; and X is COOH or OH;wherein,at least one of Ra , Rb , Rc , and Rd is methyl;
the long chain acrylate of component b) and component c) together total from about 35 mole % to about 75 mole % of the acrylate monomers;
the ratio of short chain acrylate to long chain acrylate is from about 0.05 to about 2; and
the copolymer has an Mn of 1000 to 8000 g/mol.

US Pat. No. 10,113,131

PHOSPHONO PARAFFINS

THE BOEING COMPANY, Chic...

1. A phosphono paraffin represented by formula (I):
wherein:
each instance of R1 is independently —H or

each instance of R2 and R3 is independently C1-20 alkyl, cycloalkyl of C20 or less, or aryl;
n is an integer between 4 and 22;
and the number of instances where R1 is
of formula (I) is between about 2 and about 8.

US Pat. No. 10,113,130

HIGH DENSITY/HIGH CETANE RENEWABLE FUEL BLENDS

The United States of Amer...

1. A method for making a diesel fuel blend or a jet fuel blend, comprising:(i) cycloaddition of renewable alkenes, ketones, or aldehydes to prepare multicyclic alkanes or multicyclic alkenes, (ii) converting norbornadiene to multicyclic alkanes or multicyclic alkenes, (iii) converting cyclopentadiene or a functionalized cyclopentadiene to multicyclic alkanes or multicyclic alkenes, or (iv) converting cyclooctatetraene to multicyclic alkanes or multicyclic alkenes;
preparing a synthetic paraffinic kerosene and mixing said synthetic paraffinic kerosene with the multicyclic alkanes or multicyclic alkenes prepared by one of steps (i)-(iv) to produce said deisel fuel blend with a cetane number>40 or said jet fuel blend with a viscosity below 8.5 cSt at ?20° C.

US Pat. No. 10,113,129

APPARATUS FOR CONDUCTING A HYDROTHERMAL CARBONIZATION REACTION

AVA Green Chemistry Devel...

1. An apparatus for conducting a hydrothermal carbonization reaction comprising:(a) a steam generator;
(b) a mixing tank;
(c) a buffer tank; and
(d) a reaction tank connected with the steam generator to receive hot steam and connected with the mixing tank by way of a feed pipe to receive biomass and connected with the buffer tank to drain off a slurry formed in the reaction tank from the hot steam and the biomass;
wherein the mixing tank is structured as a pulper and forms a closed heat circuit comprising a first heat exchanger for giving off heat to the biomass contained in the pulper and a second heat exchanger connected with the first heat exchanger and associated with the buffer tank for absorbing the heat from the slurry drained out of the reaction tank into the buffer tank;
wherein thermal oil is conducted in the heat circuit as a heat carrier;
wherein the at least one of the pulper and the buffer tank is surrounded by at least one heat exchanger coil or wherein at least one heat exchanger coil passes through the pulper or the buffer tank; and
wherein at least one third heat exchanger is associated with the heat circuit for withdrawing heat from the heat circuit or for feeding heat into the heat circuit in a targeted manner.

US Pat. No. 10,113,127

PROCESS FOR SEPARATING NITROGEN FROM A NATURAL GAS STREAM WITH NITROGEN STRIPPING IN THE PRODUCTION OF LIQUEFIED NATURAL GAS

1. A process for producing liquefied natural gas from a nitrogen-containing natural gas stream, the process comprising:a) cooling a stream of mixed refrigerant in a first heat exchanger of a single closed-loop mixed refrigerant system to provide a cooled mixed refrigerant stream;
b) expanding at least a portion of the cooled mixed refrigerant stream to produce an expanded mixed refrigerant stream;
c) cooling and at least partially condensing the natural gas stream in a first heat exchange passageway via indirect heat exchange with the expanded mixed refrigerant stream in the first heat exchanger to produce a cooled natural gas stream;
d) dividing the cooled natural gas stream withdrawn from the first heat exchange passageway into a first portion and a second portion;
e) introducing the first portion into a lower inlet of a first vapor-liquid separator;
f) subsequent to said dividing, subcooling the second portion in the first heat exchanger to provide a subcooled liquid portion, wherein said subcooling is carried out in a second heat exchange passageway via indirect heat exchange with said expanded mixed refrigerant;
g) subsequent to said subcooling, introducing the subcooled liquid portion into an upper inlet of the first vapor-liquid separator, wherein the upper inlet of the first vapor-liquid separator is located at a higher vertical elevation than the lower inlet;
h) withdrawing a methane rich liquid bottoms stream and a first nitrogen rich vapor overhead stream from the first vapor-liquid separator;
i) further cooling the methane rich liquid bottoms stream in the first heat exchanger in a third heat exchange passageway to provide a first liquid natural gas stream;
j) introducing at least a portion of the first liquid natural gas stream into an inlet of a nitrogen stripping column;
k) introducing at least a portion of the first nitrogen rich vapor overhead stream into another inlet of the nitrogen stripping column;
l) withdrawing a stream of nitrogen-depleted liquefied natural gas (LNG) from a lower portion of the nitrogen stripping column, wherein the LNG comprises less than 3 volume percent nitrogen;
m) recovering an overhead nitrogen rich vapor stream from a location near the top of the nitrogen stripping column, wherein the overhead nitrogen rich vapor stream comprises less than 3 volume percent methane;
n) introducing the overhead nitrogen rich vapor stream into the first heat exchanger; and
o) using at least a portion of the overhead nitrogen rich vapor stream as a refrigerant in the first heat exchanger to carry out at least a portion of the cooling of step (a) and/or at least a portion of the cooling of step (c), wherein the single closed-loop mixed refrigerant system is the only closed-loop refrigeration system used to cool the natural gas stream.

US Pat. No. 10,113,126

REUSABLE POLYMERIC MATERIAL FOR REMOVING SILOXANE COMPOUNDS IN BIOGAS, METHOD THEREBY AND APPARATUS THEREFOR

KOREA INSTITUTE OF SCIENC...

1. A polyacrylate-based polymer absorbent for removing siloxane compounds from biogas, comprising:particles of poly(meth)acrylate salt, cations of the salt being other than sodium;
hygroscopic inorganic particles, anions of the inorganic particles selected from the group consisting of chloride, bromide and iodide, cations of the inorganic particles including sodium; and
a porous support.

US Pat. No. 10,113,124

CONTROL UNIT FOR GASIFICATION POWER GENERATION PLANT, GASIFICATION POWER GENERATION PLANT, AND CONTROL METHOD FOR GASIFICATION POWER GENERATION PLANT

MITSUBISHI HITACHI POWER ...

1. A control unit for a gasification power generation plant including a gasifier that gasifies carbon-containing fuel by using an oxidizer, a gas turbine that is driven by combustion gas generated by combustion of fuel gas obtained by purifying synthesis gas from the gasifier in gas clean-up equipment, and an oxidizer supply path for supplying air extracted from an air compressor of the gas turbine or oxygen separated from the air as an oxidizer for the gasifier,the control unit for the gasification power generation plant comprising a switching unit for choosing a fixed-air-ratio mode, in which an air ratio representing the ratio of the amount of the oxidizer that is supplied to the gasifier relative to a theoretical amount of the oxidizer for combustion of the carbon-containing fuel is fixed, in a case where the gasification power generation plant is in a stable state, whereas choosing a variable-air-ratio mode, in which the air ratio is variable by varying an oxidizer amount in accordance with a load of the gasification power generation plant so that the air ratio is decreased, in a case where an operating-state quantity of the gasifier has varied or in a case where the load of the gasification power generation plant has varied.

US Pat. No. 10,113,123

PROCESS AND SYSTEM FOR EXTRACTION OF A FEEDSTOCK

1. A system for recovering aromatics from a naphtha feedstock, comprising:(a) a naphtha splitter for separating a C6+ fraction from the naphtha feedstock;
(b) a hydrotreater unit to desulphurize and separate a C6 to C11 hydrocarbon fraction from the C6+ fraction;
(c) an aromatics extraction distillation unit for recovering from the C6 to C11 hydrocarbon fraction an aromatics fraction, an aromatics precursors fraction and a raffinate fraction;
(d) a dehydrogenation unit or a reformer for converting the aromatics precursors in the aromatics precursors fraction to aromatics; and
wherein the naphtha splitter, the hydrotreater unit, and the aromatic extraction distillation unit, are operatively connected such that the C6+ fraction and the C0 to C11 hydrocarbon fraction are not subjected to a reformer or a dehydrogenation unit prior to the recovery of the aromatics fraction, the aromatics precursors fraction and the raffinate fraction.

US Pat. No. 10,113,122

PROCESS FOR UPGRADING HEAVY HYDROCARBON LIQUIDS

UNIVERSITY OF NEW BRUNSWI...

1. A hydrogen-free process for upgrading heavy hydrocarbon liquids, comprising:a) mixing a pre-heated heavy hydrocarbon liquid feedstock with glycerol and a catalyst to form a mixture, wherein the mixture has a heavy hydrocarbon liquid feedstock to glycerol weight ratio from about 5000:1 to about 100:10 and a heavy hydrocarbon liquid feedstock to catalyst weight ratio from about 5000:1 to about 100:10;
b) feeding the mixture into a first reactor comprising propellers, heated up to a temperature in a range from about 200° C. to about 450° C. to partially treat the mixture, maintaining a pressure in the first reactor in a range from about 0.6 MPa to about 0 MPa absolute, and driving said propellers to apply shear forces to the mixture in a range from about 300 N/m2 to about 10000 N/m2;
c) after a preselected period of time, flowing the partially treated mixture to a second reactor having a holding volume larger than the first reactor, heated up to a temperature in a range from about 250° C. to about 380° C. and maintaining a pressure in the second reactor in a range from about 0.6 MPa to about 0 MPa absolute to further treat the partially treated mixture, said second reactor having a bottom with a bottom exit port and top exit port such that first hydrocarbon fractions are separated from second hydrocarbon fractions, wherein the first hydrocarbon fractions have a boiling point higher the second hydrocarbon fractions, and the second hydrocarbon fractions are vaporized and flow up through the top exit and collected into a distillation column, and said first hydrocarbon fractions sink to the bottom of the second reactor and are flowed out through the bottom exit port and recirculated back to the first reactor; and
d) collecting an upper portion of the second hydrocarbon fractions separated from a lower portion of the second hydrocarbon fractions in the distillation column out through an upper exit port and storing the collected upper portion of the second hydrocarbon fractions, and collecting the lower portion of the second hydrocarbon fractions out through a lower exit port and storing the collected lower portion of the second hydrocarbon fractions, wherein the upper portion of the second hydrocarbon fractions has a boiling point lower than the lower portion of the second hydrocarbon fractions, wherein the process is carried out with no external hydrogen gas.

US Pat. No. 10,113,121

GASOLINE PRODUCTION PROCESS COMPRISING AN ISOMERIZATION STEP FOLLOWED BY AT LEAST TWO SEPARATION STEPS

AXENS, Rueil Malmaison (...

1. A process for the isomerization of a light naphtha, said process comprising an isomerization reaction step (1), said step being carried out under the following conditions:a temperature in the range 100° C. to 300° C.,
a pressure of 2 to 35 bar (1 bar=0.1 MPa), and
a molar ratio of hydrogen/hydrocarbons in the range 0.1/1 to 1/1,
a space velocity of 0.5 to 10 h?1,
the catalysts used being constituted by a support of high purity alumina comprising 2% to 10% by weight of chlorine, 0.1% to 0.40% by weight of platinum, and optional other metals, said isomerization step being followed by a step (2) for stabilization of the reaction effluents, and by two steps for separation by distillation of the bottom stream obtained from the stabilization step (2) which are placed downstream of the stabilization step (2), the two separation steps being as follows:
1—a first step for separation by distillation (block (3+4) in order to separate the hydrocarbons containing 5 carbon atoms from heavier compounds sent towards the second section for distillation by separation (5), said first separation step producing the following 3 cuts: a) a cut which is enriched in isopentane (15) which is a product of the process, b) a cut which is enriched in n-pentane (16) which is recycled to the reaction section (1), and c) a cut which is enriched in hydrocarbons which are heavier than pentanes (17), which is directed towards a second separation step (5), (5), consisting of a separation column wherein the overhead stream (19) which is rich in C6 branched compounds and bottom stream (18), are the products from the unit and an intermediate cut (20) which is enriched in n-hexane, removed as a side stream which is recycled to the reaction section (1), in which in an isomerization process an exchange of heat is carried out between a condenser of one of the columns (3), (4) or (5) and the reboiler of one of columns (3), (4) or (5).

US Pat. No. 10,113,119

THERMALLY STABLE MONOLITH CATALYST FOR REFORMING REACTION

KOREA RESEARCH INSTITUTE ...

1. A thermally stable monolith catalyst for reforming reaction, comprising:an active ingredient and Group 1A to 5A metal of barrier components represented by Formula 1 below on a monolith catalyst support, wherein the active ingredient of Formula 1 has 0.5 to 10 parts by weight based on 100 parts by weight of a monolith catalyst,
a(X)-b(Y)  Formula 1
wherein X is a catalytic active ingredient selected from Co, Ni, Ru, Rh and a mixture thereof, Y is a mixture of Zr as a promoter and Group 1A to 5A metals as a barrier component in a mixing ratio by weight of 1:0.1 to 1:10, and ‘a’ and ‘b’ denote the ratios by weight of X and Yin order, wherein ‘a’ is 1 and ‘b’ ranges from 0.2 to 1.5.

US Pat. No. 10,113,118

PROCESS AND APPARATUS FOR PRODUCING HYDROCARBON

1. Method for producing liquid hydrocarbon by converting carbonaceous material contained in one or more feedstocks, the method comprisingProviding a feed material;
Pressurizing the feed material to a predetermined process pressure of 150 to 400 bar;
Heating the pressurized feed material to a predetermined process temperature of 370 to 500° C.;
Reacting the pressurized and heated feed material for a predetermined period of time;
Cooling the reacted feed material to a temperature below 200° C.;
Mechanically separating the converted feed material at operational pressure into a higher viscosity fraction and a lower viscosity fraction, and extracting the higher viscosity fraction from the process through alternating mechanical filters between at least one online filter and at least one offline filter, the temperature of the filters being controlled to be in the range 40 to 200° C.; and
Conveying the remaining converted feed mass including the lower viscosity fraction through a pressure reduction system and further through a separation system.

US Pat. No. 10,113,117

VERTICAL ALIGNMENT LIQUID CRYSTAL DISPLAY AND MANUFACTURE METHOD THEREOF

Shenzhen China Star Optoe...

1. A manufacture method of a vertical alignment liquid crystal display, comprising steps of:step 1, loading a first substrate and a second substrate;
wherein a first passivation layer and a second passivation layer are respectively located on inner sides of the first substrate and the second substrate, and a common electrode layer and a pixel electrode layer are respectively located on the first passivation layer and the second passivation layer;
step 2, coating a glue frame on the first substrate or the second substrate;
step 3, filling a liquid crystal layer in a district surrounded by the glue frame;
wherein the liquid crystal layer comprises liquid crystal molecules, auxiliary alignment agent and polymeric monomers; and
a weight percentage of the polymeric monomers in the liquid crystal layer is 0.5%-0.8%;
step 4, assembling the first substrate and the second substrate; and
step 5, applying a voltage to the common electrode layer and the pixel electrode layer to make the liquid crystal molecules of the liquid crystal layer twisted with a predetermined degree, and employing ultraviolet (UV) light to irradiate the liquid crystal layer;
wherein the polymeric monomers are polymerized to form a polymer network penetrating the entire liquid crystal layer; and
wherein each of the polymeric monomers has at least two polymerizable groups;
wherein the polymeric monomers comprise at least one double polymerizable group monomer having two polymerizable groups and at least one polymeric group compound having at least three polymerizable groups; and a weight percentage of the polymeric group compound in the polymerizable monomers is 10%-50%.

US Pat. No. 10,113,116

LIQUID CRYSTAL COMPOUND AND LIQUID CRYSTAL COMPOSITION EMPLOYING THE SAME

DAXIN MATERIALS CORPORATI...

1. A liquid crystal composition, comprising: a first component and a third component; whereinthe first component comprises at least two liquid crystal compounds represented by Formula (I)

wherein
R1 represents hydrogen, a C1-C10 alkyl group, or a C2-C10 alkenyl group, where the C1-C10 alkyl group or the C2-C10 alkenyl group is unsubstituted or at least one —CH2— of the C1-C10 alkyl group or the C2-C10 alkenyl group is replaced by —O—, —S—, —O—CO—, —OC—O—, or —O—CO—O—, provided that the —O—, —S—, —O—CO—, —OC—O—, and —O—CO—O— do not directly bond to one another, and/or at least one hydrogen of the C1-C10 alkyl group or the C2-C10 alkenyl group is substituted by halogen, CN, or CF3;
each of A1, A2, A3, and A4 independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a divalent dioxabicyclo[2.2.2]octylene group, a divalent trioxabicyclo[2.2.2]octylene group, or a divalent 2,5-indanylene group, where the 1,4-phenylene group, the 1,4-cyclohexylene group, or the divalent 2,5-indanylene group is unsubstituted or at least one hydrogen of the 1,4-phenylene group, the 1,4-cyclohexylene group, or the divalent 2,5-indanylene group is substituted by halogen, CN, or CF3, and/or at least one —CH2— of the 1,4-cyclohexylene group is replaced by —O—, —S—, —O—CO—, —OC—O—, or —O—CO—O—, provided that the —O—, —S—, —O—CO—, —OC—O—, and —O—CO—O— do not directly bond to one another, and/or at least one —CH2— of the divalent 2,5-indanylene group is replaced by —O— or —S—, provided that the —O— and —S— do not directly bond to one another;
each of Z1, Z2, Z3 and Z4 independently represents a single bond, a C1-C4 alkylene group, a C2-C4 alkenylene group, a C2-C4 alkynylene group, —O—CO—, or —CO—O—, where the C1-C4 alkylene group, the C2-C4 alkenylene group, or the C2-C4 alkynylene group is unsubstituted or at least one hydrogen of the C1-C4 alkylene group, the C2-C4 alkenylene group, or the C2-C4 alkynylene group is substituted by halogen, and/or at least one —CH2— of the C1-C4 alkylene group, the C2-C4 alkenylene group, or the C2-C4 alkynylene group is replaced by —O— or —S—, provided that the —O— and —S— do not directly bond to each other, wherein at least one of Z1, Z2, Z3, and Z4 of one of the at least two liquid crystal compounds does not represent —OCF2— or —CF2O—;
X represents hydrogen, halogen, CN, CF3, or CCl3; and
each of m, n, o, and p independently represents 0 or 1, and m+n+o+p>0;
the third component comprises at least one liquid crystal compound represented by Formula (III)

wherein
R6 represents halogen, —CF3, —OCH?CF2, or —OCF3;
R5 represents hydrogen, a C1-C10 alkyl group, or a C2-C10 alkenyl group, where the C1-C10 alkyl group or the C2-C10 alkenyl group is unsubstituted or at least one —CH2— of the C1-C10 alkyl group or the C2-C10 alkenyl group is replaced by —O—, —S—, —CO—, —O—CO—, —CO—O—, or —O—CO—O—, and wherein the —O—, —S—, —CO—, —O—CO—, —CO—O—, and —O—CO—O— do not directly bond to one another, and/or at least one hydrogen of the C1-C10 alkyl group or the C2-C10 alkenyl group is substituted by halogen, CN, or CF3;
each of A7, A8, A9, and A10 independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a divalent dioxabicyclo[2.2.2]octylene group, a divalent trioxabicyclo[2.2.2]octylene group, or a divalent 2,5-indanylene group, where the 1,4-phenylene group, the 1,4-cyclohexylene group, or the divalent 2,5-indanylene group is unsubstituted or at least one hydrogen of the 1,4-phenylene group, the 1,4-cyclohexylene group, or the divalent 2,5-indanylene group is substituted by halogen or CN, and/or at least one —CH2— of the 1,4-cyclohexylene group is replaced by —O—, —NH—, or —S—, provided that the —O—, —NH—, and —S— do not directly bond to one another, or at least one —CH2— of the divalent 2,5-indanylene group is replaced by —O—, —NH—, or —S—, provided that the —O—, —NH—, and —S— do not directly bond to one another;
each of Z7, Z8 and Z9 independently represents a single bond, a C1-C4 alkylene group, a C2-C4 alkenylene group, a C2-C4 alkynylene group, —CO—O—, or —O—CO—, where the C1-C4 alkylene group, the C2-C4 alkenylene group, or the C2-C4 alkynylene group is unsubstituted or at least one hydrogen of the C1-C4 alkylene group, the C2-C4 alkenylene group, or the C2-C4 alkynylene group is substituted by halogen, and/or at least one —CH2— of the C1-C4 alkylene group, the C2-C4 alkenylene group, or the C2-C4 alkynylene group is replaced by —O— or —S—, and —O— does not directly bond to —O— or —S—, and —S— does not directly bond to —S—, and wherein at least one of Z7, Z8 and Z9 represents —OCF2— or —CF2O—; and
each of s, t, u, and v independently represents 0, 1, 2, or 3, and s+t+u+v?3.

US Pat. No. 10,113,115

NEMATIC LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY DEVICE USING THE SAME

DIC CORPORATION (TOKYO), ...

1. A liquid crystal composition having a negative dielectric anisotropy, the composition comprising a first component that is at least one compound represented by General Formula (i)(where Ri1 represents an alkyl group having 1 to 8 carbon atoms, and Ri2 represents an alkyl group having 3 to 8 carbon atoms) anda second component that is at least e compound selected from compounds represented by General Formula (L)(where RL1 and RL2 each independently represent an alkyl group having 1 to 8 carbon atoms; in the alkyl group, one —CH2— or at least two —CH2-'s not adjoining each other are each independently optionally substituted with —CH?CH—, —C?C—, —O—, —CO—, —COO—, or —OCO—;nL1 represents 0, 1, 2, or 3;
AL1, AL2, and AL3 each independently represent a group selected from the group consisting of(a) a 1,4-cyclohexylene group (in which one —CH2— or at least two —CH2—'s not adjoining each other are each optionally substituted with —O—),(b) a 1,4-phenylene group (in which one —CH? or at least two —CH?'s not adjoining each other are each optionally substituted with —N?), and(c) a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, one —CH? or at least two —CH?'s not adjoining each other are each optionally substituted with —N?);the groups (a) to (c) are each independently optionally substituted with a cyano group, a fluorine atom, or a chlorine atom;ZL1 and ZL2 each independently represent a single bond, —CH2CH2—, —(CH2)4—, —OCH2—, —CH2O—, —COO—, —OCO—, —OCF2—, —CF2O—, —CH?N—N?CH—, —CH?CH—, —CF?CF—, or —C?C—;
in the case where nL1 is 2 or 3 and where AL2 is multiple, the multiple AL2's may be the same as or different from each other; in the case where nL1 is 2 or 3 and where ZL3 is multiple, the multiple ZL3's may be the same as or different from each other; and the compound represented by General Formula (L) excludes the compound represented by General Formula (i)).

US Pat. No. 10,113,114

APPARATUS AND METHOD FOR COATING PARTICULATE MATERIAL

BASF Corporation, Florha...

1. A method of applying a functional additive to a particulate landscaping material, the method comprising:feeding a particulate landscaping material into a mixing chamber from a hopper, the hopper comprising two opposing sides, a baffle, a conveyor, and a sensor, the two opposing sides, the baffle, and the conveyor defining a gate;
delivering a flow of additive mixture to a plurality of spray nozzles within the mixing chamber, the additive mixture comprising a functional additive and a carrier;
operating at least one of the plurality of spray nozzles to direct an atomized spray of additive mixture into the mixing chamber for contact with particulate landscaping material in the mixing chamber;
agitating the particulate landscaping material within the mixing chamber at least one of during and after directing the atomized spray of additive mixture into the mixing chamber;
conveying the particulate landscaping material with the additive mixture applied thereto to a mixing chamber outlet;
during the feeding, delivering, operating, agitating and conveying steps, intermittently determining a volumetric flow rate of the particulate landscape material through the mixing chamber by measuring the volumetric flow rate of the particulate landscape material through the gate with the sensor;
intermittently comparing the determined volumetric flow rate of the particulate landscape material to a predetermined target flow rate of the particulate landscape material;
adjusting, based on said comparing, the volumetric flow rate of the particulate landscape material through the mixing chamber by adjusting the volumetric flow rate of the particulate landscape material through the gate.

US Pat. No. 10,113,113

REMOVING POLYSILICON

Micron Technology, Inc., ...

1. A method, comprising:forming a first instance of oxide;
forming an instance of polysilicon over the instance of oxide;
forming a second instance of oxide over the instance of polysilicon;
forming an opening through the second instance of oxide, the instance of polysilicon and the first instance of oxide;
exposing the second instance of oxide, the instance of polysilicon and the first instance of oxide to an aqueous composition; and
using the aqueous composition, recessing the instance of polysilicon relative to the first instance of oxide and the second instance of oxide within the opening;
wherein the aqueous composition comprises nitric acid, poly-carboxylic acid and ammonium fluoride.

US Pat. No. 10,113,110

BORON-LOADED LIQUID SCINTILLATOR COMPOSITIONS AND METHODS OF PREPARATION THEREOF

ATOMIC ENERGY OF CANADA L...

1. A boron-loaded liquid scintillator composition comprising: linear alkylbenzene (LAB), a carborane, 2,5-diphenyloxazole (PPO) and 1,4-bis[2-methylstyryl]benzene (bis-MSB) as a wavelength shifter, the LAB, carborane, PPO and bis-MSB being at concentrations at which the boron-loaded liquid scintillator composition enables detection of neutron signals while discriminating the neutron signals from gamma and beta radiation, the PPO at a concentration of 2-6 g/L and the bis-MSB at a concentration of 20-40 mg/L.

US Pat. No. 10,113,106

STRENGTH-ENHANCING RESIN FOR PROPPANT

Halliburton Energy Servic...

1. A method of fracturing a subterranean formation comprising:introducing a fracturing fluid into the subterranean formation, wherein the fracturing fluid comprises:
(A) a base fluid;
(B) proppant; and
(C) a curable resin having three or more epoxy functional group, wherein the curable resin is selected from the group consisting of trimethylolpropane trialycidyl ether, glycerol trialycidyl ether, pentaerythritol tetraalycidyl ether, glycerol polyethylene oxide trialycidyl ether, glycerol polypropylene oxide trialycidyl ether, polyalycerol-3-polyalycidyl ether, polyalycerol-3-olyethylene oxide polyalycidyl ether, polyalycerol-3-polypropylene oxide polyalycidyl ether, and combinations thereof;
wherein the curable resin is pre-coated onto the proppant prior to introduction into the subterranean formation;
creating or enhancing one or more fractures within the subterranean formation using the fracturing fluid;
then introducing a curing agent into the subterranean formation; and
allowing or causing to allow the curing agent to contact the curable resin in the subterranean formation; wherein the curable resin does not substantially cure prior to contacting the curing agent; wherein the curable resin cures when in contact with the curing agent; wherein the curable resin forms polymer molecules with the curing agent, and wherein the polymer molecules are non-linear or multi-directional polymers; wherein at least some of the three or more epoxy functional groups cross-link the polymer molecules together; wherein the curable resin and the curing agent form a multi-directional, cross-linked polymer network; and
wherein the cured resin increases the compressive strength of the proppant, wherein the compressive strength of the proppant is increased to a strength of at least 5,000 pounds force per square inch.

US Pat. No. 10,113,105

HYDROPHOBIZING AGENTS COMPRISING AN OLIGOMERIC POLYAMINE AND METHODS FOR COATING PARTICULATES THEREWITH

Halliburton Energy Servic...

1. A method comprising:providing a composition comprising:
a hydrophobizing agent comprising an oligomeric polyamine having a carbon atom:nitrogen atom ratio of about 4:1 or more, and a plurality of hydrophobic groups bonded to at least a portion of the nitrogen atoms in the oligomeric polyamine; and
forming coated particulates comprising a coating of the hydrophobizing agent on one or more particulates,
wherein the hydrophobizing agent is cationic and comprises at least one of: one quaternized nitrogen atom, or one protonated nitrogen atom.

US Pat. No. 10,113,104

SUPERHYDROPHIC FLOW CONTROL DEVICE

Halliburton Energy Servic...

1. A wellbore subassembly, comprising:a flow control device having a helical enclosed production flow path toward a production tubing, the helical enclosed production flow path being positioned circumferentially about the production tubing, wherein the helical enclosed production flow path includes a superhydrophobic coating on an inner surface of the helical enclosed production flow path for restricting production of an unwanted fluid toward the production tubing, the superhydrophobic coating having a contact angle with a water droplet in the unwanted fluid that exceeds 150°, and wherein the superhydrophobic coating is operable for increasing a velocity of fluid having a greater concentration of oil flowing along the production flow path, wherein the inner surface of the helical enclosed production flow path has a plurality of protrusions.

US Pat. No. 10,113,102

ACTIVITY ENHANCED SCALE DISPERSANT FOR TREATING INORGANIC SULFIDE SCALES

Multi-Chem Group, LLC, S...

14. A composition comprising:a base fluid;
a scale inhibitor, wherein the scale inhibitor comprises a phosphonate;
a water clarifying agent, wherein the water clarifying agent comprises at least one compound selected from the group consisting of: a polyDADMAC, a DADMAC acrylamide copolymer, and any combination thereof; and
a sulfide precipitate.

US Pat. No. 10,113,101

COMPOSITION AND METHOD FOR DISPERSING PARAFFINS IN CRUDE OILS

Ecolab USA Inc., St. Pau...

1. A method for reducing paraffin or wax deposition in a crude oil storage or transportation vessel, the method comprising adding a composition to a crude oil in an amount effective to reduce paraffin or wax deposition in the storage or transportation vessel containing the crude oil, wherein the crude oil has an API gravity of at least 33 and the composition comprisesa copolymer which is a product of a polymerization reaction comprising (i) an alpha olefin monomer and a maleic anhydride monomer, (ii) the alpha olefin monomer and an alkyl maleic anhydride monomer, (iii) the maleic anhydride monomer and styrene; or (iv) the alkyl maleic anhydride monomer and styrene, the alpha olefin monomer having the formula (I):
wherein R1 is hydrogen or C12-C30 alkyl and R2 is C12-C30 alkyl, and the alkyl maleic anhydride monomer having the formula (II):wherein R3 is C12-C30 alkyl and R4 is hydrogen or C12-C30 alkyl;an anionic surfactant; and
a solvent; and
wherein if the copolymer is the product of the polymerization reaction comprising (i) the alpha olefin monomer and the maleic anhydride monomer, R1 is hydrogen and R2 is C24-C30 alkyl.

US Pat. No. 10,113,100

COMPOSITIONS WITH POLYAZIRIDINE CROSSLINKERS FOR TREATING SUBTERRANEAN FORMATIONS

Saudi Arabia Oil Company,...

1. A method of treating a subterranean formation comprising:i) providing to a subterranean formation a composition comprising:a maleic anhydride copolymer, or a salt thereof; andat least one hydrolyzed repeat unit selected from repeat units III and IV:

or a salt thereof, wherein each R5 is independently selected from —OH and NH2, provided that at least one of R5 is NH2, anda polyaziridine crosslinker having the formula:or a salt thereof, wherein:L1 and L2 at each occurrence are each independently selected from the group consisting of —C1-6 alkylene-, —C1-6 alkenylene-, —C1-6 alkynylene-, —(O—C1-4 alkylene)p-, —(C1-4 alkylene-O—)p—, —O—, —S—, NH—, and —C(?O)—, wherein said —C1-6 alkylene-, —C1-6 alkenylene-, —C1-6 alkynylene-, and —C1-4 alkylene- are each optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of -halo, —CN, —OH, —C1-3 alkyl, —C1-3 alkoxy, —C1-3 haloalkyl, —C1-3 haloalkoxy, -amino, —C1-3 alkylamino, and -di(C1-3 alkyl)amino;
each R3 is selected from the group consisting of —H, —C1-6 alkyl, —C1-6 alkenyl, —C1-6 alkynyl, -halo, —CN, —OH, —C1-3 alkoxy, —C1-3 haloalkyl, —C1-3 haloalkoxy, -amino, —C1-3 alkylamino, -di(C1-3 alkyl)amino, —(O—C1-4 alkylene)p-H, and (C1-4 alkylene-O—)p—C1-6 alkyl;
each R4 is selected from the group consisting of:

 wherein each of (a) and (b) is optionally substituted with 1, 2, 3, or 4 substituents independently selected from the group consisting of halo, CN, OH, amino, C1-3 alkylamino, di(C1-3 alkyl)amino, —C1-3 alkyl, C1-3 alkoxy, C1-3 haloalkyl, and C1-3 haloalkoxy;
p at each occurrence is independently an integer from 0 to 40;
x and y at each occurrence are each independently an integer from 0 to 10;
m is an integer from 2 to 4; and
n is an integer from 0 to 4;
provided that the sum of m and n is 4; and
ii) crosslinking the maleic anhydride copolymer, or a salt thereof, and the polyaziridine crosslinker, or a salt thereof, to form a sealant.

US Pat. No. 10,113,098

COMPOSITION INCLUDING VISCOSIFIER POLYMER AND POLYAMINE VISCOSITY MODIFIER FOR TREATMENT OF SUBTERRANEAN FORMATIONS

Halliburton Energy Serviv...

1. A composition for treatment of a subterranean formation, the composition comprising:a viscosifier polymer comprising
an ethylene repeating unit comprising an —NRa—C(O)—Rb group, wherein at each occurrence Ra and Rb are each independently selected from —H and substituted or unsubstituted (C1-C20)hydrocarbyl or Ra and Rb together form a substituted or unsubstituted (C2-C20)hydrocarbylene,
an ethylene repeating unit comprising an —S(O)2OR1 group wherein at each occurrence R1 is independently selected from —H, substituted or unsubstituted (C1-C20)hydrocarbyl, and a counterion,
at least one crosslinker repeating unit comprising an ethylene repeating unit at each occurrence independently linked to an ethylene repeating unit in the same viscosifier polymer molecule or in another molecule of the viscosifier polymer via a substituted or unsubstituted (C1-C40)hydrocarbylene interrupted by 0, 1, 2, or 3 groups independently chosen from —O—, —S—, and substituted or unsubstituted —NH—,
wherein the repeating units are in block, alternate, or random configuration; and
a polyamine viscosity modifier, wherein the polyamine viscosity modifier is present in the composition in an amount of about 0.01 wt % to about 5 wt %, wherein the polyamine viscosity modifier reduces the viscosity of the composition such that the composition comprising the polyamine viscosity modifier has a lower viscosity than an equivalent composition without the polyamine viscosity modifier.

US Pat. No. 10,113,097

PROCESS FOR THE PRODUCTION OF A THERMALLY CONDUCTIVE ARTICLE

1. A process for the production of a thermally conductive article, said process comprising:pleating at least one thermally anisotropic sheet having a first thermal conductivity in a first plane which is higher than a second thermal conductivity in a second plane that is perpendicular to the first plane to form a pleated structure, said pleated structure comprises a plurality of pleats, each said pleat having a first surface and a second surface; and
compacting the pleated structure so that said first and second surfaces which face each other due to the formation of said pleats are at least partially brought into direct contact with each other, said pleated structure having an upper surface and a lower surface,
wherein the thermally anisotropic sheet includes at least one thermally anisotropic polymer layer.

US Pat. No. 10,113,095

REINFORCED GRAPHITIC MATERIAL

MICROSOFT TECHNOLOGY LICE...

1. A method for making a reinforced graphitic material, the method comprising:sorbing a solution of an organic compound into void space between graphitic platelets of a graphitic host material;
mechanically pressing the graphitic host material while heating the graphitic host material to evaporate a solvent of the solution and deposit sorbed organic compound into the void space;
heating the graphitic host material with the sorbed organic compound to pyrolyze the sorbed organic compound and thereby deposit elemental carbon in the void space, the elemental carbon crosslinking the graphitic platelets of the graphitic host material; and
after heating the graphitic host material with the sorbed organic compound to pyrolyze the sorbed organic compound, mechanically re-pressing while heating the graphitic host material.

US Pat. No. 10,113,089

ARTICLES AND METHODS COMPRISING POLYACRYLATE PRIMER WITH NITROGEN-CONTAINING POLYMER

3M Innovative Properties ...

1. An optical film stack comprising:a first optical film bonded to a microstructured surface layer comprising microstructured prisms, of a second optical film with a cured adhesive layer comprising an interpenetrating network of the reaction product of a polyacrylate and polymerizable monomer; wherein the second optical film further comprises a primer layer disposed between the cured adhesive layer and the microstructured surface layer of the second optical film and the primer layer consists essentially of a polyacrylate and a nitrogen-containing polymer, and wherein at least a portion of the prisms comprise a post extending from an apex of the prisms that functions as a optically non-active bonding portion.

US Pat. No. 10,113,086

EXPANDABLE TAPE

1. A hanging system in a room of a building comprising:at least one of a wall and a ceiling;
a sheet; and
wherein a first side of the sheet is connected to the at least one of the wall and the ceiling by a first widthwise expandable tape and a second widthwise expandable tape, wherein the first widthwise expandable tape is spaced apart from the second widthwise expandable tape, each of the first widthwise expandable tape and second widthwise expandable tape comprising:
a first adhesive strip defining one lengthwise edge of the widthwise expandable tape;
a second adhesive strip defining the other lengthwise edge of the widthwise expandable tape;
a flexible region connecting the first adhesive strip to the second adhesive strip, the flexible region adapted to lengthen and contract to allow a movement of the second adhesive strip away from and towards the first adhesive strip in a widthwise direction of the widthwise expandable tape upon an application of a force to at least one of the first adhesive strip and the second adhesive strip;
wherein the first widthwise expandable tape comprises a first quantity of adhesive on a bottom face of the first adhesive strip, and comprises a second quantity of adhesive disposed on a bottom face of the second adhesive strip, the bottom face of the second adhesive strip facing a same direction as the bottom face of the first adhesive strip.

US Pat. No. 10,113,084

MOLD RELEASE AGENT

Illinois Tool Works, Inc....

1. A mold release coating on a mold surface, the mold release coating being derived from a polysiloxane having the formula of formula 1:
where y?3 and x is ?0, where a reactive moiety for the purposes of the present invention include those moieties that react on the mold surface to form bonds to other polymers of Formula (I), the mold surface, or both, where reactive moieties comprise one or more of R4, R5, R6, or R7, where R4, R5, R6, or R7 are the same or different and each is independently one or more of reactive moieties of glycydoxy, C1-C8 alkoxy, C1-C8 alkoxy having a substituent, or independently one or more of unreactive moieties C1-C8 or longer alkyl, either branched or unbranched; and where R1 R2, R3, R8, R9, and R10 can be the same or different and each independently is a saturated C1-C8 or greater alkyl, either linear or branched with the proviso any hydrogen present in the R groups is non-labile; and
the mold surface being an inflatable elastomeric bladder surface, the polysiloxane bonded to the rubber bladder surface by reaction of the one or more reactive moieties.

US Pat. No. 10,113,083

RESIST UNDERLAYER FILM-FORMING COMPOSITION CONTAINING POLYMER WHICH CONTAINS NITROGEN-CONTAINING RING COMPOUND

NISSAN CHEMICAL INDUSTRIE...

1. A resist underlayer film-forming composition for lithography comprising a linear polymer that is obtained by a reaction of a diepoxy group-containing compound (A) with a dicarboxyl group-containing compound (B), wherein the linear polymer has structures of the following formulae (1), (2), and (3) derived from the diepoxy group-containing compound (A) or the dicarboxyl group-containing compound (B):
in Formula (1), X1 is a group of Formula (4), (5), or (6):

wherein each of R1, R2, R3, and R4 is a hydrogen atom, a C1-6 alkyl group, a C3-6 alkenyl group, benzyl group, or phenyl group, the phenyl group may be substituted by a group selected from the group consisting of a C1-6 alkyl group, a halogen atom, a C1-6 alkoxy group, a nitro group, a cyano group, a hydroxyl group, and a C1-6 alkylthio group, and R1 and R2 or R3 and R4 may be bonded to each other to form a C3-6 ring; and R5 is a C1-6 alkyl group, a C3-6 alkenyl group, benzyl group, or phenyl group, and the phenyl group may be substituted by a group selected from the group consisting of a C1-6 alkyl group, a halogen atom, a C1-6 alkoxy group, a nitro group; a cyano group, a hydroxyl group, and a C1-6 alkylthio group; and
Ar in Formula (2) is an aromatic C6-20 fused ring, and the ring may be substituted by a group selected from the group consisting of a C1-6 alkyl group, a halogen atom, a C1-6 alkoxy group, a nitro group, a cyano group, a hydroxyl group, and a C1-6 alkylthio group, wherein
the linear polymer is a polymer obtained by a reaction of two diepoxy group-containing compounds (A), one having the structure of Formula (1) and the other having the structure of Formula (2), with a dicarboxyl group-containing compound (B) having a structure of Formula (3); or
the linear polymer is a polymer obtained by a reaction of a diepoxy group-containing compound (A) having a structure of Formula (1) with two dicarboxyl group-containing compounds (B), one having the structure of Formula (2), and the other having the structure of Formula (3).

US Pat. No. 10,113,078

INK DISCHARGE DEVICE AND INK DISCHARGE METHOD

Ricoh Company, Ltd., Tok...

1. An ink discharge device comprising:an ink comprising:
water;
a colorant;
an organic solvent X having a solubility parameter of from 8.9 to 12.0, the organic solvent X comprising no glycol ether compound; and
a copolymer comprising a structural unit represented by the following formula (1):

where R1 represents a hydrogen atom or methyl group and Y represents an alkylene group having 2 to 18 carbon atoms;
an ink discharge head including:
a nozzle configured to discharge the ink;
a plurality of individual liquid chambers in communication with the nozzle;
a flow-in channel configured to let the ink flow into the individual liquid chambers; and
a flow-out channel configured to let the ink flow out from the individual liquid chambers; and
a negative pressure generator configured to generate a negative pressure that lets the ink flow out from the individual liquid chambers,
wherein the ink discharge head is configured to let the ink having flowed out from the flow-out channel flow into the flow-in channel to circulate the ink.

US Pat. No. 10,113,075

POLYCYCLIC PHOTOINITIATORS

IGM Malta Limited, (MT)

1. A photopolymerizable composition comprising:(A) at least one ethylenically unsaturated photopolymerizable compound and
(B) at least one photoinitiator compound of formula (I):

wherein
X is O, S, a direct bond or CR16R17;
Y is O or S;
R1, R2, R3, R4, R5, R6, R7 and R8 independently of each other are hydrogen, halogen, C1-C4alkyl, C5-C7cycloalkyl, phenyl, C1-C4alkoxy, C5-C7cycloalkoxy, phenoxy, C1-C4alkylthio, C5-C7cycloalkylthio, phenylthio, di(C1-C4alkyl)amino, di(C5-C7cycloalkyl)amino, N-morpholinyl, N-piperidinyl or a group of formula (II) or (III):

provided that
one of R1, R2, R3 or R4 is a group of formula (II) or (III) and one of R5, R6, R7 or R8 is a group of formula (II) or (III);
R9 and R10 independently of each other are C1-C4alkyl or together with the C atom to which they are attached form a 5-membered, 6-membered or 7-membered carbocyclic ring;
R11 is hydrogen, C1-C4alkyl, C5-C7cycloalkyl, 2-tetrahydropyranyl or Si(C1-C4alkyl)3;
R12 and R13 independently of each other are C1-C4alkyl, C2-C12alkenyl, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl which is substituted by C1-C4alkyl, or R12 and R13 together with the C atom to which they are attached form a 5-membered, 6-membered or 7-membered carbocyclic ring;
R14 and R15 independently of each other are C1-C4alkyl, C5-C7cycloalkyl, or together with the N atom to which they are attached form a 5-membered, 6-membered or 7-membered ring, which may contain additional heteroatoms O, S or N;
R16 and R17 independently of each other are hydrogen, C1-C8alkyl, C5-C7cycloalkyl, phenyl-C1-C4alkyl, phenyl or together with the C atom to which they are attached form a 5-membered, 6-membered or 7-membered ring;
provided that;
(1) compounds wherein R2 is a group of formula (III) and R14 and R15 together with the N atom to which they are attached form a 6-membered ring, which contains an additional heteroatom O, X is a direct bond and Y is O; and
(2) compounds wherein R2 is a group of formula (III) and R14 and R15 together with the N atom to which they are attached form a 6-membered ring, which contains an additional heteroatom O and X and Y are S; and
(3) compounds wherein R7 is a group of formula (III) and R14 and R15 together with the N atom to which they are attached form a 6-membered ring, which contains an additional heteroatom O and X and Y are S; are excluded.

US Pat. No. 10,113,074

THERMALLY INKJETTABLE ACRYLIC DIELECTRIC INK FORMULATION AND PROCESS

FUNAI ELECTRIC CO., LTD.,...

1. An electronic device that comprises a dielectric layer, the dielectric layer being formed by one or more layers of an aqueous composition comprising:from about 5 to about 20 percent by weight of an acrylic polymeric binder emulsion;
from about 5 to about 30 percent by weight of a humectant;
from about 0 to about 3 percent by weight of a surfactant; and
an aqueous carrier fluid,
wherein the aqueous composition has a viscosity ranging from about 2 to about 6 centipoise,
wherein the dielectric layer has a thickness ranging from about 10 microns to about 40 microns, and
wherein the one or more layers have a glass transition temperature ranging from about 40° C. to about 110° C.

US Pat. No. 10,113,073

DIELECTRIC THICK FILM INK

GM GLOBAL TECHNOLOGY OPER...

1. A thermally conductive thick film dielectric ink for an electronic device, the thermally conductive thick film dielectric ink comprising a mixture of:an organic medium present in an amount from about 14.0 to about 32.0% by weight of the thick film dielectric ink, wherein the organic medium comprises 2,2,4-trimethyl-1,3-pentanediol present in an amount from about 81.0% to about 82.0% by weight of the organic medium, Diethylene Glycol Dibutyl Ether present in an amount from about 7.0% to about 11.0% by weight of the organic medium, Dodecyl Alcohol present in an amount about 2.0% by weight of the organic medium, Tridecyl Alcohol present in an amount from about 1.0% to about 4.0% by weight of the organic medium, and Ethyl Cellulose present in an amount from about 3.0 to about 6.5% by weight of the organic medium;
a glass binder; and
a technical ceramic powder having ceramic particles dispersed throughout the thermally conductive thick film dielectric ink mixture.

US Pat. No. 10,113,072

ELECTROPHORETIC PARTICLE, METHOD OF MANUFACTURING ELECTROPHORETIC PARTICLE, ELECTROPHORESIS DISPERSION LIQUID, ELECTROPHORESIS SHEET, ELECTROPHORESIS DEVICE, AND ELECTRONIC APPARATUS

E Ink Corporation, Bille...

1. An electrophoretic particle, comprising:a particle including a first functional group on a surface; and
a first compound, a second compound, and a third compound bonded to the particle,
wherein the first compound is a block copolymer that includes a dispersion portion derived from a first monomer including a site that contributes to dispersibility in a dispersion medium, and a bonding portion derived from a second monomer including a second functional group having reactivity with the first functional group, and is connected to the particle by reacting the functional group and the second functional group in the bonding portion,
the second compound has a lower molecular weight than the first compound, includes a non-polar group and the second functional group, and is connected to the particle by the second functional group reacting with the first functional group, and
the third compound has a lower molecular weight than the first compound, includes a charging group and the second functional group, and is connected to the particle by the second functional group reacting with the first functional group.

US Pat. No. 10,113,070

PRETREATMENT COMPOSITIONS AND METHODS OF TREATING A SUBSTRATE

PPG industries Ohio, Inc....

1. A pretreatment composition for treating a metal substrate, comprising:(a) a Group IIIB metal and/or a Group IVB metal present in a total amount of 20 ppm to 1000 ppm (calculated as elemental metal) based on the total weight of the pretreatment composition;
(b) a compound containing at least six phosphorus-containing acid groups or salts thereof present in an amount of 1.82×10?4 moles per liter to 2.73×10?2 moles per liter of pretreatment composition; and
(c) an electropositive metal;
wherein the molar ratio of (a) to (b) is at least 3:1;
wherein the pretreatment composition is capable of reacting with and chemically altering the substrate surface and binding to it to form a film that affords corrosion protection.

US Pat. No. 10,113,065

TWO-PHOTON ABSORBING COMPOUNDS AND METHODS OF MAKING SAME

1. A two-photon active compound having a structural formula:wherein A is an aromatic-heterocyclic ?-electron acceptor moiety that is connected to m number of diarylaminofluorene arms (m=1-3); in each diarylaminofluorene arms, R is selected from linear or branched alkyl chains having a general formula CnH2n+1, where n is in a range from 2 to 25; wherein R1, R2, and R3 are independently selected from the group consisting of H and C1-C5 alkyls; wherein R4 is selected from the group consisting of C1-C5 alkyls; and wherein R5 through R10 are independently selected from the group consisting of H, alkoxyls, alkyls, and aryls.

US Pat. No. 10,113,057

METHOD FOR FORMING A POLYETHYLENE NANOCOMPOSITE

King Fahd University of P...

1. A method for forming a high-density polyethylene nanocomposite by polymerizing a mixture of ethylene and a calcium zirconate nanofiller, comprising:adding a zirconocene catalyst, the calcium zirconate nanofiller and a solvent to a reactor;
mixing the zirconocene catalyst and the calcium zirconate nanofiller in the solvent;
injecting ethylene into the reactor until absorption of ethylene is no longer observed; followed by
adding a methylaluminoxane cocatalyst into the reactor to from a catalyst mixture; then
polymerizing the ethylene by pressurizing the reactor with ethylene and maintaining a pressure of 1-1.5 bar to form a polymerization mixture; and then
quenching the polymerization mixture with methanol to form the high-density polyethylene nanocomposite;
wherein the calcium zirconate nanofiller is dispersed in a polyethylene matrix of the high-density polyethylene nanocomposite, and
the calcium zirconate nanofiller is not a support material for the zirconocene catalyst.

US Pat. No. 10,113,053

ISOSORBIDE EPOXIDE DIESTERS, AND THE USE THEREOF AS A PLASTICIZER IN PVC COMPOSITIONS

ROQUETTE FRERES, Lestrem...

1. A compound of the following formula (I):

US Pat. No. 10,113,052

5H-FURAN-2-ONE DERIVATIVES STABILIZATION OF ORGANIC MATERIAL

BASF SE, Ludwigshafen (D...

1. A composition comprisinga) a polyolefin, a polyester polyol, or a polyurethane;
b) compound having a structure,

 and
c) an additive selected from the group consisting of a phosphite, a phosphonite, an acid scavenger, a phenolic antioxidant, and an aminic antioxidant.

US Pat. No. 10,113,051

EPOXY ESTOLIDE FATTY ACID ALKYL ESTERS USEFUL AS BIORENEWABLE PLASTICIZERS

Regents of the University...

1. A composition comprising epoxy estolide fatty acid alkyl esters derived from triacylglycerol oil having an unsaturation of greater than 80 IV, wherein the estolide is derived from an epoxy group.

US Pat. No. 10,113,049

THERMOPLASTIC RESIN COMPOSITION

NIPPON NYUKAZAI CO., LTD....

1. A method for improving a gloss retention property of a thermoplastic resin composition comprising the step of combining(a) a thermoplastic resin, where said thermoplastic resin is not an aromatic polycarbonate resin or a polyvinyl chloride resin, and
(b) as ionically bonded salt represented by the following Chemical Formula (1) or (2):

in the Chemical Formula (I) above, R1 represents a substituted or unsubstituted linear, branched, or cyclic alkyl group having from 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms where the aryl group is not substituted with an alkyl group, or a substituted or unsubstituted arylalkyl group having from 7 to 31 carbon atoms,
A is a linear or branched alkylene group having from 2 to 4 carbon atoms,
n represents an integer of 1 to 50,
Q1 represents at least one kind selected from the group consisting of a dimethylammonium ion, a trimethylammonium ion, a diethylammonium ion, a triethylammonium ion, a monopropylammonium ion, a dipropylammonium ion, a tripropylammonium ion, a monobutylammonium ion, a dibutylammonium ion, a tributylammonium ion, a monopentylammonium ion, a dipentylaminoammonium ion, a tripentylammonium ion, a monohexylammonium ion, a dihexylammonium ion, a monoheptylammonium ion, a diheptylammonium ion, a monooctylammonium ion, a dioctylammonium ion, a monononylammonium ion, a monodecylammonium ion, a monoundecylammonium ion, a monododecylammonium ion, a monotridecylammonium ion, a monotetradecylammonium ion, a monopentadecylammonium ion, a monohexadecylammonium ion, a monoheptadecylammonium ion, a monooctadecylammonium ion, a monononadecylammonium ion, a monoicosylammonium ion, a monohenicosylammonium ion, a monodocosylammonium ion, a monotricocylammonium ion, a methyl(ethyl)ammonium ion, a methyl(propyl)ammonium ion, a methyl(butyl)ammonium ion, a methyl(pentyl)ammonium ion, a methyl(hexyl)ammonium ion, a methyl(heptyl)ammonium ion, a methyl(octyl)ammonium ion, a methyl(nonyl)ammonium ion, a methyl(decyl)ammonium ion, a methyl(undecyl)ammonium ion, a methyl(dodecyl)ammonium ion, a methyl(tridecyl)ammonium ion, a methyl(tetradecyl)ammonium ion, a methyl(pentadecyl)ammonium ion, a methyl(hexadecyl)ammonium ion, a methyl(heptadecyl)ammonium ion, a methyl(octadecyl)ammonium ion, a methyl(nonadecyl)ammonium ion, a methyl(icosyl)ammonium ion, a methyl(henicosyl)ammonium ion, a methyl(tricosyl)ammonium ion, an ethyl(propyl)ammonium ion, an ethyl(butyl)ammonium ion, an ethyl(pentyl)ammonium ion, an ethyl(hexyl)ammonium ion, an ethyl(heptyl)ammonium ion, an ethyl(octyl)ammonium ion, an ethyl(nonyl)ammonium ion, an ethyl(decyl)ammonium ion, an ethyl(undecyl)ammonium ion, an ethyl(dodecyl)ammonium ion, an ethyl(tridecyl)ammonium ion, an ethyl(tetradecyl)ammonium ion, an ethyl(pentadecyl)ammonium ion, an ethyl(hexadecyl)ammonium ion, an ethyl(heptadecyl)ammonium ion, an ethyl(octadecyl)ammonium ion, an ethyl(nonadecyl)ammonium ion, an ethyl(icosyl)ammonium ion, an ethyl(henicosyl)ammonium ion, an ethyl(tricosyl)ammonium ion, a dimethyl(ethyl)ammonium ion, a dimethyl(propyl)ammonium ion, a dimethyl(butyl)ammonium ion, a dimethyl(pentyl)ammonium ion, a dimethyl(hexyl)ammonium ion, a dimethyl(heptyl)ammonium ion, a dimethyl(octyl)ammonium ion, a dimethyl(nonyl)ammonium ion, a dimethyl(decyl)ammonium ion, a dimethyl(undecyl)ammonium ion, a dimethyl(dodecyl)ammonium ion, a dimethyl(tridecyl)ammonium ion, a dimethyl(tetradecyl)ammonium ion, a dimethyl(pentadecyl)ammonium ion, a dimethyl(hexadecyl)ammonium ion, a dimethyl(heptadecyl)ammonium ion, a dimethyl(octadecyl)ammonium ion, a dimethyl(nonadecyl)ammonium ion, a dimethyl(icosyl)ammonium ion, a dimethyl(henicosyl)ammonium ion, a dimethyl(tricosyl)ammonium ion, a monobenzylammonium ion, a (1-phenethyl)ammonium ion, a (2-phenethyl)ammonium ion, a dibenzylammonium ion, a bis(1-phenethyl)ammonium ion, a bis(2-phenethyl)ammonium ion, a monocyclopentylammonium ion, a dicyclopentylammonium ion, a tricyclopentylammonium ion, a monocyclohexylammonium ion, a dicyclohexyl ammonium ion, a monocycloheptylammonium ion, a dicycloheptylammonium ion, a dimethyl(cyclopentyl)ammonium ion, a dimethyl(cyclohexyl)ammonium ion, a dimethyl(cycloheptyl)ammonium ion, a (methylcyclopentyl)ammonium ion, a bis(methylcyclopentyl)ammonium ion, a (dimethylcyclopentyl)ammonium ion, a bis(dimethylcyclopentyl)ammonium ion, a (ethylcyclopenty)ammonium ion, a bis(ethylcyclopentyl)ammonium ion, a (methylethylcyclopentyl)ammonium ion, a bis(methylethylcyclopentyl)ammonium ion, a (diethylcyclopentyl)ammonium ion, a (methylcyclohexyl)ammonium ion, a bis(methylcyclohexyl)ammonium ion, a (dimethylcyclohexyl)ammonium ion, a bis(dimethylcyclohexyl)ammonium ion, an (ethylcyclohexyl)ammonium ion, a bis(ethylcyclohexyl)ammonium ion, a (methylethylcyclohexyl)ammonium ion, a (diethylcyclohexyl)ammonium ion, a (methylcycloheptyl)ammonium ion, a bis(methylcycloheptyl)ammonium ion, a (dimethylcycloheptyl)ammonium ion, an (ethylcycloheptyl)ammonium ion, a (methylethylcycloheptyl)ammonium ion, a (diethylcycloheptyl)ammonium ion, a monomethanolammonium ion, a dimethanolammonium ion, a monoethanolammonium ion, a diethanolammonium ion, a mono(n-propanol)ammonium ion, a di(n-propanol)ammonium ion, a monoisopropanolammonium ion, a diisopropanolammonium ion, a monobutanolammonium ion, a dibutanolammonium ion, a tributanolammonium ion, a monopentanolammonium ion, a dipentanolammonium ion, a tripentanolammonium ion, a monohexanolammonium ion, a dihexanolammonium ion, a monoheptanolammonium ion, a diheptanolammonium ion, a monooctanolammonium ion, a monononanolanamonium ion, a monodecanolammonium ion, a monoundecanolammonium ion, a monododecanolammonium ion, a monotridecanolammonium ion, a monotetradecanolammonium ion, a monopentadecanolammonium ion, a monohexadecanolammonium ion, a monomethylmonoethanolammonium ion, a monoethylmonoethanolammonium ion, a monoethylmonopropanolammonium ion, a monoethylmonobutanolammonium ion, a monoetylpentanolammonium ion, a monopropylmonoethanolammonium ion, a monopropylmonopropanolammonium ion, a monopropylmonobutanolammonium ion, a monopropylmonopentanolammonium ion, a monobutylmonoethanolammonium ion, a monobutylmonopropanolammonium ion, a monobutylmonobutanolammonium ion, a monobutylmonopentanolammonium ion, a dimethylmonoethanolammonium ion, a diethylmonoethanolammonium ion, a diethylmonopropanolammonium ion, a diethylmonobutanolammonium ion, a diethylmonopentanolammonium ion, a dipropylmonoethanolammonium ion, a dipropylmonopropanolammonium ion, a dipropylmonobutanolammonium ion, a dipropylmonopentanolammonium ion, a dibutylmonoethanolammonium ion, a dibutylmonopropanolammonium ion, a dibutylmonobutanolammonium ion, a dibutylmonopentanolammonium ion, a monomethyldiethanolammonium ion, a monomethyldipropanolammonium ion, a monomethyldibutanolammonium ion, a monomethyldipentanolammonium ion, a monoethyldiethanolammonium ion, a monoethyldipropanolammonium ion, a monoethyldibutanolammonium ion, a monoethyldipentanolammonium ion, a monopropyldiethanolammonium ion, a monopropyldipropanolammonium ion, a monopropyldibutanolammonium ion, a monopropyldipentanolammonium ion, a monobutyldiethanolammonium ion, a monobutyidipropanolammonium ion, a monobutyldibutanolammonium ion, a monobutyldipentanolammonium ion, a monocyclohexylmonoethanolammonium ion, a monocyclohexyldiethanolammonium ion, a monocyclohexylmonopropanolammonium ion, a monocyclohexyldipropanolammonium ion, a mono(?-aminoethyl)monoethanolammonium ion, a monotert-butylmonoethanolammonium ion, and a mono(?-aminoethyl)isopropanolammonium ion,

in the Chemical Formula (2) above, R2represents 1,2-Bis(2-ethylhexyloxycarbonyl)ethyl group, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms where the aryl group is not substituted with an alkyl group, or a substituted or unsubstituted arylalkyl group having from 7 to 31 carbon atoms with the proviso that the aryl group is not a naphthyl group or not substituted with a substituted or unsubstituted phenyl group,
A is a linear or branched alkylene group having from 2 to 4 carbon atoms,
n represents an integer of 1 to 50,
Q2 represents at least one kind selected from the group consisting of a monomethanolammonium ion, a dimethanolammonium ion, a monoethanolammonium ion, a diethanolammonium ion, a mono(n-propanol)ammonium ion, a di(n-propanol)ammonium ion, a monoisopropanolammonium ion, a diisopropanolammonium ion, a monobutanolammnonium ion, a dibutanolammonium ion, a tributanolammonium ion, a monopentanolammonium ion, a dipentanolammonium ion, a tripentanolammonium ion, a monohexanolammonium ion, a dihexanolammonium ion, a monononanolammonium ion, a diheptanolammonium ion, a monooctanolammonium ion, a monononanolammonium ion, a monodecanolammonium ion, a monoundecanolammonium ion, a monoclodecanolammonium ion, a monotridecanolammonium ion, a monotetradecanolammonium ion, a monopentadecanolammonium ion, a monohexadecanolammonium ion, a monomethylmonothanolammonium ion, a monoethylmonoethanolammonium ion, a monoethylmonopropanolamnonium ion, a monoethylmonobutanolammonium ion, a monoethylpentanolammonium ion, a monopropylmonoethanolammonium ion, a monopropylmonopropanolammonium ion, a monopropylmonobutanolammonium ion, a monopropylmonopentanolammonium ion, a monobutymonoethanolammonium ion, a monobutylmonopentanolammonium ion, a monobutylmonobutanolammonium ion, a monobutylmonopentanolammonium ion, a dimethylmonoethanolammonium ion, a diethylmonoethanolammonium ion, a diethylmonopropanolammonium ion, a diethylmonobutanolammonium ion, a diethylmonopentanolammonium ion, a dipropylmonoethanolammonium ion, a dipropylmonopropanolammonium ion, a dipropylmonobutanolammonium ion, a dipropylmonopentanolammonium ion, a dibutylmonoethanolammonium ion, a dibutylmonopentanolammonium ion, a dibutylmonobutanolammonium ion, a dibutylmonopentanolammonium ion, a monomethyldiethanolammonium ion, a monomethyldipropanolammonium ion, a monomethyldibutanolammonium ion, a monomethyldipetanolammonium ion, a monoethyldiethanolammonium ion, a monoethyldipropanolammonium ion, a monoethyldibutanolammonium ion, a monoethyldipentanolammonium ion, a monopropyldiethanolammonium ion, a monopropyldipropanolammonium ion, a monopropyldibutanolammonium ion, a monopropyldipentanolammonium ion, a monobutyldiethanolammonium ion, a monobutyldipropanolammonium ion, a monobutyldibutanolaumonium ion, a monobutyldipentanolammonium ion, a monocyclohexylmonoethanolammonium ion, a monocyclohexyldiethanolammonium ion, a monocyclohexylmonopropanolammonium ion, a monocyclohexyldipropanolammonium ion, a mono(?-aminoethyl)monoethanolammenium ion, a monotert-butylmonoethanolammonium ion, a monotert-butyldiethanolammonium ion, a mono(?-aminoethyl)isopronanolammonium ion, and a diethylmonoisopropanolammonium ion, wherein the thermoplastic resin composition is in the form of an emulsion when the (b) ionically bonded salt is represented by the Chemical Formula (1) above.

US Pat. No. 10,113,047

EXFOLIATED GRAPHITE-RESIN COMPOSITE MATERIAL AND METHOD FOR PRODUCING THE SAME

SEKISUI CHEMICAL CO., LTD...

1. An exfoliated graphite-resin composite material comprisingan exfoliated graphite and
a resin
said exfoliated graphite and said resin forming the exfoliated graphite-resin composite, and
when an amount of methylene blue adsorbed per g of the exfoliated graphite-resin composite material (?mol/g) is y, the amount of methylene blue adsorbed as measured based on a difference between an absorbance of a methanol solution of methylene blue at a concentration of 10 mg/L and an absorbance of a supernatant liquid obtained by introducing the exfoliated graphite-resin composite material into the methanol solution of methylene blue and performing centrifugation, and a BET specific surface area (m2/g) of the exfoliated graphite-resin composite material is x,
a ratio y/x being 0.15 or more, and the BET specific surface area being 25 m2/g or more, and
said exfoliated graphite-resin composite has a graphite structure in the central portion and has an exfoliated structure in the edge portion.

US Pat. No. 10,113,045

MOLDED FOAM ARTICLE, FOAMED SOLE, AND SHOE

ASICS CORPORATION, (JP)

1. A molded foam article comprising:a foam obtained by foaming a formation material, wherein the formation material of the foam comprises (i) at least one resin component selected from a thermoplastic elastomer, a thermoplastic resin, and a rubber, and (ii) at least one softener selected from a vegetable oil and a mineral oil,
wherein an Asker C hardness of the foam is 10 degrees or more,
wherein the at least one resin component and the at least one softener are selected such that a ratio E40/E0 of the foam is (i) equal to or more than 0.5 and (ii) equal to or less than 3.5, the ratio E40/E0 being a ratio of an elastic coefficient E40 at a compressive strain of 40% in relation to an elastic coefficient E0 at a compressive strain of 0% of the foam, and
wherein a difference between (i) H1 as an Asker C hardness when a load of 0.1 MPa is applied and (ii) H0 as an Asker C hardness in a no load state, is within a range of ±20 degrees.

US Pat. No. 10,113,044

METHODS OF PROCESSING LATEX, METHODS OF MAKING CARPET, AND CARPETS

SST Foam, LLC, Alpharett...

1. A method of processing a latex stream, the method comprising:forwarding the latex stream to a reservoir of a foam head;
disposing an isocyanate into the reservoir of the foam head to form a foamed latex stream comprising the isocyanate; and
forwarding the foamed latex stream comprising the isocyanate from the reservoir of the foam head to a coating line;
wherein the concentration of the isocyanate in the foamed latex stream is about 0.5 to about 2.25%, by weight of the latex stream.

US Pat. No. 10,113,040

POLYMER FILM, POLARIZING PLATE AND LIQUID CRYSTAL DISPLAY DEVICE

FUJIFILM CORPORATION, To...

1. A polymer film, which comprises:a carbonyl bond-containing polymer; and
a compound having ?h of equal to or higher than 11.0 and ?? of equal to or lower than 1.50, wherein the ?h is a value of hydrogen-bonding capacity calculated by Hoy method and the ?? is a value calculated by equation 1:
??=|x?13.3|   Equation 1
wherein, in equation 1, ? represents an interatomic distance in the polymer film between atoms most distant from each other among molecules in the compound, excluding a hydrogen atom, calculated by molecular dynamics calculation,
wherein said compound is represented by a compound selected from the group:
i) formula (I-1):
(Q3-(L32-L31)n3-A-(L41-L42)n4)m-Z1
wherein each of L31 and L41 independently represents an alkylene group, and the alkylene group may be substituented, each of L32 and L42 independently represents a single bond, or any one of or any combination of —O—, —NR1—, —S— and —C(?O)—, R1 represents a hydrogen atom or a substituent, each of n3 and n4 independently represents an integer of 0 to 20, either n3 or n4 is an integer equal to or higher than 1, and when L31, L32, L41 and L42 exist in plural number, they may be the same as or different from each other, Q3 represents a substituent, Z1 represents an m-valent linking group, and A represents *—O—C(?O)—NH— or *—NH—C(?O)—O—, where * represents a bonding position with L41, m represents an integer of 2 to 6, and Q3 and A existing in plural number may be the same as or different from each other, respectively, and at least one of Q3 and Z1 contains a ring structure,
wherein Z1 is

*—CH2-CH(-*)—CH2-* is formula

*—CH2-C(CH3)(CH2-*)—CH2-* is formula
or*—CH2-CH(C2H5)(CH2-*)—CH2-* is formula

ii) formula (I-3):

wherein each of L71 and L81 independently represents an alkylene group, and the alkylene group may be substituented, each of L72 and L82 independently represents a single bond or any one of or any combination of —O—, —NR1—, —S— and —C(?O), R1 represents a hydrogen atom or a substituent, each of n7 and n8 independently represents an integer of 0 to 12, either n7 or n8 is an integer equal to or higher than 1, and when L71, L72, L81 and L82 exist in plural number, they may be the same as or different from each other, Q5 represent a substituted or an unsubstituted phenyl group, a substituted or unsubstituted cyclohexyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group or a t-butyl group, A represents *—O—C(?O)—NH— or *—NH—C(?O)—O—, where * represents a bonding position with L81, and R2a represents an alkyl group having 1 to 3 carbon atoms, m2 represents an integer of 2 or 3, and Q5 and A existing in plural number may be the same as or different from each other, respectively, a represents an integer of 0 to 10, and, when a is an integer equal to or higher than 1, R2a existing in plural number may be the same as or different from each other;
iii) formula (I-5):

wherein each of L71 and L81 independently represents an alkylene group, and the alkylene group may be substituented, each of L72 and L82 independently represents a single bond or any one of or any combination of —O—, —NR1—, —S— and —C(?O), each of n7 and n8 independently represents an integer of 0 to 12, either n7 or n8 is an integer equal to or higher than 1, and when L71, L72, L81 and L82 exist in plural number, they may be the same as or different from each other, Q5 represent a substituted or an unsubstituted phenyl group, a substituted or unsubstituted cyclohexyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group or a t-butyl group, A represents *—O—C(?O)—NH— or *—NH—C(?O)—O—, where * represents a bonding position with L81, Q5 and A existing in plural number may be the same as or different from each other, respectively, m3 represents 1 or 2, and each of R3 and R4 independently represents a hydrogen atom or a methyl group;
iv) formula (II):

wherein in formula (II) each of L1a and L1b independently represents a single bond, an alkylene group, or a group represented by any of the above-described formulas (2A) to (2E), or a group consisting of a combination of a group represented by any of formulas (2A) to (2E) and two or three alkylene groups, and each of Q1a and Q1b independently represents a substituent, at least one of Q1a and Q1b represents a phenyl group which may have been substituted by an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms;
v) formula (III):

wherein in formula (III) each of L1a and L1b independently represents a single bond, an alkylene group, or a group represented by any of the above-described formulas (2A) to (2E), or a group consisting of a combination of a group represented by any of formulas (2A) to (2E) and two or three alkylene groups, and each of Q1a and Q1b independently represents a substituent, at least one of Q1a and Q1b represents a phenyl group which may have been substituted by an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms;
vi) formula (A):
QA-La1-X—C(?O)—NH-La2-QB
wherein X represents —NR—, and R represents a hydrogen atom or a substituent, each of La1 and La2 independently represents a single bond, or any one of or any combination of an alkylene group, an arylene group, —O—, —NR1—, —S— and —C(?O)—, R1 represents a hydrogen atom or a substituent, each of QA and QB independently represents a substituent, and at least one of QA and QB represents a polar group being a residue of a compound having a C log P value equal to or lower than 0.85, or a terminal group contained in the substituent.

US Pat. No. 10,113,034

POLYMERS FROM STABILIZED IMINES

International Business Ma...

1. A method for producing a polymer, comprising:forming a reaction mixture comprising a non-polar solvent and an imine compound comprising electron withdrawing or accepting groups;
adding a multifunctional nucleophile to the mixture; and
heating the mixture at a temperature from about 50° C. to about 150° C. to produce a polymer.

US Pat. No. 10,113,033

POLYMER CONJUGATE FOR DELIVERY OF A BIOACTIVE AGENT

POLYACTIVA PTY LTD, Melb...

1. A polymer-bioactive agent conjugate comprising:a polymer backbone comprising a plurality of triazole moieties; and
a plurality of releasable prostaglandin analogues covalently bonded to and pendant from the polymer backbone from the 1-position of the prostaglandin analogue via an ester linking group.

US Pat. No. 10,113,032

AMINE FUNCTIONAL POLYAMIDES

Genzyme Corporation, Cam...

1. A compound comprising the structure of Formula (II):
wherein:
i) m is 1, 2, or 3;
ii) n is 0, 1, 2, or 3;
iii) o is 1, 2, or 3;
iv) q is an integer from 1 to 400;
v) Qx is NH, (C1-C10)alkyl, (C2-C9)heteroalkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl;
vi) Qv is NH—Rw, NH—CH2—Rw, (C1-C10)alkyl, or (C6-C14)aryl, wherein Rw is absent or a (C1-C10)alkyl, (C2-C9)heteroalkyl, (C6-C14)aryl, or (C2-C9)heteroaryl;
vii) Rx and Ry are each independently a pharmaceutically acceptable end group;
viii) X? is each independently a halo or any pharmaceutically acceptable anion;
ix) Y1 and Y2 are each independently H or (C1-C10)alkyl optionally substituted by one or more substituents selected from the group consisting of (C1-C10)alkyl, (C2-C9)heteroalkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, —S—O—(C1-C10)alkyl, —O(O)C—(C1-C10)alkyl, —(C1-C10)alkyl-COOH, (C3-C10)cycloalkyl-COOH, —(O)CH3, —OH, amide, a dihydroxy group, represented by Formula (D),

wherein d is an integer from 0 to 25, or
a polyethylene glycol group, represented by Formula (E)

wherein e is an integer from 1 to 25, and provided that Y1 and Y2 are not both H.

US Pat. No. 10,113,031

AROMATIC DISPERSANT COMPOSITION

1. A polymer represented by Formula (1):
wherein dispersant of Formula (1) has a terminal and/or pendant imide group, wherein the side chain imide group is derived from an imide compound represented by Formula (1a):

wherein
R1 is a substituent on Q ring in any position available for bonding to a substituent group and R1 is independently represented by one or more of —H, or an electron withdrawing group selected from the group of: —NO2, —SO2NR?2, —C(O)R?, —SO3M, halo, —NH2, and —OR? or an electron releasing alkyl group, a is the total number of sites on the Q ring available for bonding a H, electron withdrawing groups, and electron releasing groups, when R1 is said electron withdrawing group or said alkyl group, then the total number of electron withdrawing and alkyl groups is 1 or 2; M is H, a metal cation, NR?4+, or mixtures thereof; R? is —H, an optionally-substituted alkyl containing 1 to 20 carbon atoms, and the substituent is hydroxyl or halo or mixtures thereof;
Q is a fused or non-fused aromatic ring containing 4n+2 ?-electrons, wherein n=1 or more, and Q is bonded to the imide group in such a way to form a 5 or 6 membered imide ring;
R2 is a C1 to C20 hydrocarbylene group or mixtures thereof; R2 optionally includes oxygen and/or nitrogen atoms wherein there is at least 2 carbon atoms per every oxygen or nitrogen of R2 these would include ether, ester, and amide type linkages in R2;
Pol is a residue of a diepoxide or polyepoxide further comprising at least one pendant side chain of one or more of:
a polyether,
a polyester,
a mixed polyether/polyester pendant side chains thereof,
a mixed polyester/polyether pendant side chains thereof,
or mixtures thereof,
the bond(s) between Pol and each W? allows for one or more terminal and/or pendant side chain imide groups (as defined by w) to be attached to Pol at one or more locations on Pol and for each imide group to be attached to Pol by one or more bond (as defined by b);
W is any group capable of reaction with an epoxide group;
W? represents amino, carboxylic acid and hydroxyl with the H missing and is a residue of the reaction of an amino, hydroxyl or carboxyl group, with a diepoxide or polyepoxide in a reaction forming a chemical bond between an amino, hydroxy, or carboxyl group with an epoxide; when b is 2 then one of the W? is derived from a secondary amine reacted with said epoxide and optionally is in the R2 linking group between the imide and the other W? group, when b is 2 each W? group is the same or different;
b is 1 or 2 and when b is 1, the imide group can either be terminal and attached to the Pol by one chemical bond when W is hydroxyl or carboxylic acid, or a pendant side chain when W is NH2 and when b is 2 the imide group is a side chain attached to Pol by two chemical bonds;
d is 1, 2, or 3; this means that there is the possibility of 1 to 3 imide groups attached to R2 at different carbon atoms of R2; and
w is 1 or more.

US Pat. No. 10,113,030

RESIST MATERIAL AND PATTERN FORMING METHOD USING SAME

Toshiba Memory Corporatio...

1. A pattern forming method comprising:providing, on a substrate, a resist material which comprises a diluent monomer having a hydroxyl group and at least one functional group selected from a vinyl ether group, an epoxy group and an oxetanyl group, a dendrimer with a globular structure having at least two reactive groups for photo-cationic polymerization, and a photo-acid generator as a polymerization initiator;
imprinting a template having concave-convex shape patterns against the resist material;
curing the resist material; and
releasing the template from the cured resist material.

US Pat. No. 10,113,028

EPOXY RESIN, CURABLE RESIN COMPOSITION, CURED PRODUCT, SEMICONDUCTOR ENCAPSULATING MATERIAL, SEMICONDUCTOR DEVICE, PREPREG, CIRCUIT BOARD, BUILDUP FILM, BUILDUP SUBSTRATE, FIBER-REINFORCED COMPOSITE MATERIAL AND FIBER-REINFORCED MOLDED ARTICLE

DIC Corporation, Tokyo (...

1. An epoxy resin, comprising as essential components, a cresol-naphthol co-condensed novolac epoxy resin (A), a naphthol glycidyl ether compound (B), and one or more xanthene compounds (C) selected from the group of compounds represented by the following structural formulae (1) to (3), wherein the content of the xanthene compound(s) (C) is from 0.1% to 5.5% in terms of area ratio in a GPC measurement:wherein in the structural formulae (1) to (3), R? each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, m each independently represents an integer of 1 to 6,wherein the content of the glycidyl ether compound (B) is from 0.1% to 4.0% in terms of area ratio in a GPC measurement.

US Pat. No. 10,113,023

ANTISTATIC POLYMERS AND METHODS OF MAKING THE SAME

3M Innovative Properties ...

1. An antistatic polymer consisting of:divalent segments p) represented by the formula

wherein
R1 independently represents an alkyl group having from 1 to 18 carbon atoms,
R2 and R3 independently represent alkyl groups having from 1 to 4 carbon atoms,
R4 independently represents an alkylene group having from 2 to 8 carbon atoms, and
R5 independently represents H or methyl; and
divalent segments q) represented by the formula)

US Pat. No. 10,113,022

PHOTORESIST POLYMERS AND METHODS OF FORMING PATTERNS

Samsung Electronics Co., ...

6. A photoresist polymer synthesized from a repeating unit, the repeating unit comprising:a first leaving group including an ester group; and
a second leaving group capable of being removed with the first leaving group,
wherein the first leaving group and the second leaving group are positioned in one of a staggered conformation and an anti-periplanar configuration,
wherein the second leaving group includes a tosylate group.

US Pat. No. 10,113,021

PROPYLENE RANDOM COPOLYMER

Borealis AG, Vienna (AT)...

1. A process for preparing a propylene random copolymers, comprising:copolymerising propylene with a comonomer selected from ethylene, C4-C20-alpha olefin, and any combination thereof using a catalyst system comprising a co-catalyst and optionally an external electron donor and an olefin polymerisation catalyst component in the form of solid particles being produced by
a) preparing a solution of at least one alkoxy compound (Ax) being the reaction product of at least one compound of a Group 2 metal with at least a monohydric alcohol (A) in an organic liquid reaction medium,
b) adding said solution to at least one compound of a transition metal and
c) preparing the solid catalyst component particles,
wherein an internal electron donor selected from benzoates, alkylene glycol dibenzoates, maleates, 1-cyclohexene-1,2-dicarboxylic dialkylester, and 1,3-ethers, or a mixture of any selected donors, or a corresponding precursor is added at any step prior to step c),
wherein the propylene random copolymer has
i) the comonomer selected from ethylene, C4-C20-alpha olefin, and any combination thereof
ii) a comonomer content in the range of 1.5 to at most 5.0 wt %
iii) a randomness in the range of 60% to at most 80%
iv) a xylene soluble (XS) content of 2 to <12 wt %, and
the propylene random copolymers is free from catalyst originating phthalates,
wherein in addition to the at least one alkoxy compound (Ax) at least one alkoxy compound (Bx) is present, being the reaction product of at least one compound of Group 2 metal and an alcohol (B) comprising in addition to the hydroxyl moiety at least one further oxygen bearing group being different to a hydroxyl moiety.

US Pat. No. 10,113,019

METHODS OF CHANGING POLYOLEFIN PRODUCTION CONDITIONS TO MITIGATE SMALL GELS IN A POLYOLEFIN ARTICLE

Univation Technologies, L...

1. A method comprising:contacting in a fluidized bed gas phase reactor an olefin monomer with a catalyst system in the presence of an induced condensing agent (ICA) and optionally hydrogen to produce a first polyolefin having a first melt index;
increasing by 10% or less (1) a concentration of the ICA in the reactor, (2) a residence time of the first polyolefin in the reactor, or (3) both to produce a second polyolefin having a second melt index, wherein the second melt index is within 10% of the first melt index; and
wherein a first thin film formed of the first polyolefin has a larger count of a small gel than a second thin film formed of the second polyolefin, wherein the first and second thin film are produced by a same procedure, and wherein the small gel is a gel particle having a diameter of 201 microns to 600 microns and counting the small gel is determined by surface inspection of a 50 micron ±5 micron thin film using optoelectronic analysis.

US Pat. No. 10,113,008

STARCH SETTLING RECOVERY SYSTEM

1. A process consisting essentially of:a. obtaining a waste water stream having starch content between 0.1 and 5% by weight starch and feeding the waste water stream to a classifier to concentrate the slurry by a factor of at least 5 and produce a concentrated slurry, wherein the classifier has at least one overflow exit and at least one underflow exit;
b. drawing off the overflow and underflow from the classifier;
c. feeding the concentrated slurry from the underflow exit of the classifier into a settling tank having at least one settling tank underflow exit and at least one settling tank overflow exit, to produce a settling tank underflow layer of starch with a concentration of between 40 and 60% starch, the settling tank underflow layer being proximate to the settling tank's underflow exit and an aqueous settling tank overflow layer having a starch concentration of less than 5% by weight starch proximate to the settling tank overflow exit,
d. allowing the settling tank underflow layer to exit through the settling tank underflow exit as a starch cake having moisture content between 40 and 60%; and
e. collecting the starch cake for shipping.

US Pat. No. 10,112,999

ANTI-PRLR ANTIBODY-DRUG CONJUGATES (ADC) AND USES THEREOF

AbbVie Inc., North Chica...

1. An antibody-drug conjugate (ADC) comprising the structure of Formula (X), or a salt thereof,
wherein Formula (X) comprises a monoclonal anti-PRLR antibody (Ab) conjugated to “n” cytotoxic warheads,
wherein said monoclonal anti-PRLR antibody comprises:
i. a heavy chain variable region comprising a CDRH1 sequence comprising SEQ ID NO: 3, a CDRH2 sequence comprising SEQ ID NO: 4, and a CDRH3 sequence comprising SEQ ID NO: 5;
ii. a light chain variable region comprising a CDRL1 sequence comprising SEQ ID NO: 8, a CDRL2 sequence comprising SEQ ID NO: 9, and a CDRL3 sequence comprising SEQ ID NO: 10; and
iii. a mutation comprising S239C in a heavy chain constant region, wherein the numbering is in accordance with Kabat,
wherein said monoclonal anti-PRLR antibody is conjugated to said cytotoxic warheads through said S239C mutation in said heavy chain constant region, and
wherein “n” is 2.

US Pat. No. 10,112,976

PROCESS FOR THE PRODUCTION OF D-ARGINYL-2,6-DIMETHYL-L-TYROSYL-L-LYSYL-L-PHENYLALANINAMIDE

1. A liquid-phase process for the production of H-D-Arg-(2,6-Dimethyl)Tyr-Lys-Phe-NH2 of formula (I), in the form of the trifluoroacetic acid salt,
which comprises the following steps:
coupling compound (II) H-Phe-NH2:

with compound (III) Z-Lys(Boc)-OH:

to obtain a compound of formula (IV), Z-Lys-Lys(Boc)-Phe-NH2:

reacting compound (IV) with hydrogen and methanesulfonic acid (V)
MeSO3H  (V)
in the presence of a catalyst to obtain the free amine salt (VI) MeSO3H.H-Lys(Boc)-Phe-NH2:

reacting salt (VI) with the protected amino acid Z-Dmt(Boc)-OH (VII)

to obtain the protected tripeptide Z-Dmt(Boc)-Lys(Boc)-Phe-NH2 (VIII):

treating compound (VIII) with hydrogen and methanesulfonic acid (V) to obtain the corresponding salt MeSO3.H-Dmt(Boc)-Lys(Boc)-Phe-NH2 (IX):

coupling the acid salt (IX) with Z-D-Arg-ONa (X)

to form the protected tetrapeptide Boc-D-Arg-Dmt(Boc)-Lys(Boc)-Phe-NH2 (XI):

deprotecting compound (XI) to obtain the tetrapeptide H-D-Arg-Dmt-Lys-Phe-NH2 (I) and further salifying it with trifluoroacetic acid in solvents.

US Pat. No. 10,112,975

BENZODIAZEPINE DIMERS, CONJUGATES THEREOF, AND METHODS OF MAKING AND USING

Briston-Myers Squibb Comp...

1. A compound having a structure represented by formula (IIb-03):

US Pat. No. 10,112,973

PROCESS FOR THE PREPARATION OF RAMIPRIL

SANOFI-AVENTIS DEUTSCHLAN...

1. A process for preparing a compound of formula (VI)
wherein:
R1 is CO2R4 or CN;
R2 is (C1-C4)alkyl;
R3 is
(C1-C4)alkyl, wherein one, two or three hydrogen atoms are optionally replaced by fluorine, (C1-C4)alkoxy, or
phenyl;
R4 is (C1-C4)alkyl; and
Ar is
phenyl, optionally substituted with one, two or three substituents independently selected from the group consisting of halogen, (C1-C4)alkoxy and (C1-C4)alkyl, or
1-naphthyl;
comprising
reacting a chiral amine of formula (IV)

wherein:
R1 is CO2R4 or CN;
R4 is (C1-C4)alkyl; and
Ar is
phenyl, optionally substituted with one, two or three substituents independently selected from the group consisting of halogen, (C1-C4)alkoxy and (C1-C4)alkyl, or
1-naphthyl;
with a 2-acylamino-acrylic acid ester of formula (V)

wherein:
R2 is (C1-C4)alkyl; and
R3 is
(C1-C4)alkyl, wherein one, two or three hydrogen atoms are optionally replaced by fluorine, (C1-C4)alkoxy, or
phenyl,
to produce the compound of formula (VI).

US Pat. No. 10,112,970

PROCESS FOR THE PREPARATION OF 17-DESOXY-CORTICOSTEROIDS

Taro Pharmaceutical Indus...

1. A process for preparing a compound of Formula I
in which R1 is OH and R2 is H, or R1 and R2 form together a double bond with O, R3 is H and R4 is CH3, or R3 is CH3 and R4 is H, and wherein at least one of X1-5 is independently Cl, Br or F, and all other of X1-5 are H, comprising the steps of:
(a) reacting a compound of formula II

in which R1-R4 and X1-5 are as defined in Formula I with Trimethylsilyl Iodide in a solution of an aprotic solvent, wherein the molar ratio between Trimethylsilyl Iodide and the compound of Formula II is about 2:1 to about 10:1;
(b) quenching the reaction of step (a);
(c) extracting the compound of Formula I from the solution of step (b) using an organic solvent to yield an organic layer comprising the compound of Formula I; and
(d) isolating the compound of Formula I from the organic layer of step (c).

US Pat. No. 10,112,969

COMPOSITIONS AND METHODS FOR SEQUENCING NUCLEIC ACIDS

INDUSTRIAL TECHNOLOGY RES...

1. A compound having Formula I:
or a pharmaceutically acceptable salt or hydrate thereof, wherein
n is 1, 2, 3, 4, 5, 6, 7, 8, or 9;
i) R1 and each R2 are O?; or
ii) R1 is

 and each R2 is O?; or
iii) R1 is O?, one R2 is

 and any remaining R2 is independently O?, S?, BH3?, or CH3;
R3 is a nucleotide moiety comprising a fluorescent dye F and at least one non-complementary nucleotide residue;
R4 is H, OH, halogen, alkyl (both substituted and unsubstituted), or alkoxy (both substituted and unsubstituted);
Y1, and Y3 are each independently chosen from O?, S?, BH3?, and CH3;
L1 is chosen from alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, ester, amino, and sulfonyl;
Q is a fluorescence quenching moiety; and
B1 is chosen from adenine, cytosine, guanine, thymine, uracil, hypoxanthine, and 5-methylcytosine.

US Pat. No. 10,112,968

INHIBITORS OF PROTEIN METHYLTRANSFERASE DOT1L AND METHODS OF USE THEREOF

Epizyme, Inc., Cambridge...

1. A compound of Formula (IIa) or a pharmaceutically acceptable salt or ester thereof:wherein,A is O or CH2;
each of G and J, independently, is H, halo, C(O)OH, C(O)O—C1-C6 alkyl or ORa, Ra being H, C1-C6 alkyl, C(O)—C1-C6 alkyl, or silyl, wherein C(O)O—C2-C6 alkyl, C1-C6 alkyl or C(O)—C1-C6 alkyl is optionally substituted with one or more substituents selected from the group consisting of halo, cyano hydroxyl, carboxyl, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, and C3-C8 cycloalkyl;
each X independently is N or CRx, in which Rx is H, halo, hydroxyl, carboxyl, cyano, or RS1, RS1 being amino, C1-C6 alkoxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, or 5 to 6-membered heteroaryl, and RS1 being optionally substituted with one or more substituents selected from the group consisting of halo, hydroxyl, carboxyl, cyano, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, and 5 to 6-membered heteroaryl;
L1 is N(Y), S, SO, or SO2;
L2 is CO or absent when L1 is N(Y) or L2 is absent when L1 is S, SO, or SO2, in which Y is H, Rd, SO2Rd, or CORd when L2 is absent, or Y is H or Rd when L2 is CO, Rd being C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, or 5 to 6-membered heteroaryl, and Rd being optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo, hydroxyl, carboxyl, cyano, C1-C6 alkoxyl, C1-C6 alkylsulfonyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, and 5 to 6-membered heteroaryl and with C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, or 5 to 6-membered heteroaryl further optionally substituted with C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo, hydroxyl, carboxyl, C(O)OH, C(O)O—C1-C6 alkyl, OC(O)—C1-C6 alkyl, cyano, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, or 5 to 6-membered heteroaryl;
each of R1, R2, R3, R4, R5, R6, and R7, independently, is H, halo, hydroxyl, carboxyl, cyano, RS2, RS2 being amino, C1-C6 alkoxyl, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl, and each RS2 being optionally substituted with one or more substituents selected from the group consisting of halo, hydroxyl, carboxyl, cyano, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, and 5 to 6-membered heteroaryl;
R8 is H, halo or RS3, RS3 being C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl, and RS3 being optionally substituted with one or more substituents selected from the group consisting of halo, hydroxyl, carboxyl, cyano amino, C1-C6 alkoxyl, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, and C3-C8 cycloalkyl; and
Q is H, NH2, NHRb, NRbRc, Rb, ?O, OH, or ORb, in which each of Rb and Rc independently is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 7-membered heterocycloalkyl, 5 to 10-membered heteroaryl, or -M1-T1 in which M1 is a bond or C1-C6 alkyl linker optionally substituted with halo, cyano, hydroxyl or C1-C6 alkoxyl and T1 is C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, or 5 to 10-membered heteroaryl, or Rb and Rc, together with the N atom to which they attach, form 4 to 7-membered heterocycloalkyl having 0 or 1 additional heteroatoms to the N atom optionally substituted with C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo, hydroxyl, carboxyl, C(O)OH, C(O)O—C1-C6 alkyl, OC(O)—C1-C6 alkyl, cyano, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, or 5 to 6-membered heteroaryl, and each of Rb, Rc, and T1 is optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo, hydroxyl, carboxyl, cyano, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, and 5 to 6-membered heteroaryl;
R9 is
in which:each of Re, Rf, Rg, and Rh, independently is -M2-T2, in which M2 is a bond, SO2, SO, S, CO, CO2, O, O—C1-C4 alkyl linker, C1-C4 alkyl linker, NH, or N(Rt), Rt being C1-C6 alkyl, and T2 is H, halo, or RS4, RS4 being C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 8-membered heterocycloalkyl, or 5 to 10-membered heteroaryl, and each of O—C1-C4 alkyl linker, C1-C4 alkyl linker, Rt, and RS4 being optionally substituted with one or more substituents selected from the group consisting of halo, hydroxyl, carboxyl, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, and 5 to 6-membered heteroaryl, Ri is H or C1-C6 alkyl optionally substituted with one or more substituents selected from the group consisting of halo, hydroxyl, carboxyl, cyano, C1-C6 alkoxyl, amino, mono-C1-C6 alkylamino, di-C1-C6 alkylamino, C3-C8 cycloalkyl, C6-C10 aryl, 4 to 6-membered heterocycloalkyl, and 5 to 6-membered heteroaryl;
q is 0, 1, 2, 3, or 4;
m is 0, 1, or 2; and
n is 0, 1, or 2.

US Pat. No. 10,112,967

PROCESS FOR THE PREPARATION OF SOFOSBUVIR

HC-PHARMA AG, Zug (CH)

1. A process for the synthesis of Sofosbuvir of formula (I)
comprising
selectively mono-deacetylating a compound of formula (V)

enzymatically using a resin supported lipase B derived from Candida Antarctica in a polar protic solvent at a temperature from 40° C. to 70° C. to obtain a compound of formula (IV)

converting the compound of formula (IV) to a compound of formula (II)

by reacting the compound of formula (IV) with a compound of formula (III)

wherein F5 indicates that the aromatic ring is pentafluoro substituted, and
converting the compound of formula (II) to Sofosbuvir of formula (I) by deacetylation reaction.

US Pat. No. 10,112,966

SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF

Alios BioPharma, Inc., S...

1. A compound selected from the group consisting of:or a pharmaceutically acceptable salt of the foregoing.

US Pat. No. 10,112,965

BICYCLIC BRIDGED METALLOCENE COMPOUNDS AND POLYMERS PRODUCED THEREFROM

Chevron Phillips Chemical...

1. A metallocene compound having the formula:wherein:M is Ti, Zr, or Hf;
each X independently is a monoanionic ligand;
E is a norbornane group, a norbornene group, a norbornadiene group, an indane group, an indene group, or a dicyclopentadiene group; and
Cp1 and Cp2 independently are a substituted or unsubstituted cyclopentadienyl, indenyl, or fluorenyl group.

US Pat. No. 10,112,964

DITHIOLENE METAL COMPLEX COLORLESS IR ABSORBERS

BASF SE, Ludwigshafen (D...

1. A method of using colorless IR absorbers comprisinga) treating a material with a compound from the group consisting of

wherein the material is a security print, an invisible and IR readable bar code,
a laser-welded plastic, a dried print, a fixed toner on paper, a laser marked plastic, or a heated preform,
optionally a further IR absorber; and
b) using the treated material of a) for security printing, invisible and IR readable bar codes, laser-welding of plastics, drying of print, fixing of toners on paper, laser marking, and heating of plastics preforms.

US Pat. No. 10,112,962

BORON-BASED PRODRUG STRATEGY FOR INCREASED BIOAVAILABILITY AND LOWER-DOSAGE REQUIREMENTS FOR DRUG MOLECULES CONTAINING AT LEAST ONE PHENOL (OR AROMATIC HYDROXYL) GROUP

XAVIER UNIVERSITY, New O...

1. A compound of Formula 29:
wherein R is selected from the group consisting of:

 KF3B; (HO)2B; and NaF3B; and
wherein the boron atom is the point of attachment in each R variable substituent, and any salts thereof.

US Pat. No. 10,112,961

HYDROBORATION AND BORYLATION WITH COBALT CATALYSTS

The Trustees of Princeton...

1. A method of providing a borylated product comprising:providing a reaction mixture comprising an aliphatic compound or an aromatic compound, a borylation reagent and a cobalt complex having Formula (IV):
wherein X1 and X2 are independently selected from Group VIIA of the Periodic Table and R1-R11 are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-aryl and alkyl-heteroaryl, wherein the alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-aryl and alkyl-heteroaryl are optionally substituted with one or more substituents selected from the group consisting of (C1-C10)-alkyl, (C1-C10)-alkenyl, alkoxy, halo, hydroxy, C(O)OR12, NR13R14, wherein R12-R14 are independently selected from the group consisting of hydrogen, (C1-C10)-alkyl and (C1-C10)-alkenyl;adding an activator to the reaction mixture to activate the cobalt complex; and
reacting the aliphatic compound or aromatic compound with the borylation reagent in the presence of the activated cobalt complex or a derivative of the activated cobalt complex.

US Pat. No. 10,112,960

METHODS FOR PRODUCING BORYLATED ARENES

Dow AgroSciences LLC, In...

1. A method of forming a borylated arene comprising:providing a substrate comprising a substituted arene ring comprising from 1 to 4 substituents, wherein the arene ring is unsubstituted at a first position that is electronically favored for CH-activation and unsubstituted at a second position that is sterically favored for CH-activation; and
contacting the substrate with an iridium precursor complex, an electron deficient bidentate ligand comprising at least one nitrogen heteroatom, and a borylation reagent under conditions effective to form a first borylated arene and optionally a second borylated arene;
wherein the electron deficient bidentate ligand comprises a compound defined by Formula IVa

wherein n is 0, 1, 2, or 3 and R10 is, independently for each occurrence, hydrogen, a halogen, a nitrile group, a nitro group, a C1-C6 alkyl group, or a C1-C6 perfluoroalkyl group, with the proviso that at least one of R10 is chosen from a halogen, a nitrile group, a nitro group, and a C1-C6 perfluoroalkyl group;
wherein the first borylated arene comprises a substituted arene ring comprising from 1 to 4 substituents and a boronic acid or a boronic acid derivative in the first position,
wherein the second borylated arene, when formed, comprises a substituted arene ring comprising from 1 to 4 substituents and a boronic acid or a boronic acid derivative in the second position, and
wherein the molar ratio of the first borylated arene to the second borylated arene is at least 1:1, as determined by GC-FID.

US Pat. No. 10,112,959

METAL COMPLEX AND COLOR CONVERSION FILM COMPRISING SAME

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

1. A compound of the following Chemical Formula 1:
wherein, in Chemical Formula 1,
at least one of R1 to R5 is selected from among the following structural formulae;

R6 is hydrogen; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted alkylaryl group; or a substituted or unsubstituted aromatic or aliphatic heterocyclic group;
X1 and X2 are the same as or different from each other, and each independently F; a nitrile group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted arylalkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted aromatic or aliphatic heterocyclic group, or bond to each other to form an aromatic or aliphatic ring;
X3 is a halogen group; a nitrile group; a carbonyl group; an ester group; an amide group; a sulfonate group; a substituted or unsubstituted alkyl group; a fluoroalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; or a substituted or unsubstituted alkylaryl group;
Y1 is CR101 or N, Y2 is CR102 or N, Y3 is CR103 or N and Y4 is CR104 or N; and
groups of R1 to R5 that are not the above-mentioned structural formulae, R8 to R13 and R101 to R104 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a carbonyl group; an ester group; an imide group; an amide group; a sulfonate group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted aromatic or aliphatic heterocyclic group, and R9 and R10 bond to each other to form an aliphatic or aromatic ring, and R12 and R13 bond to each other to form an aliphatic or aromatic ring.

US Pat. No. 10,112,958

N-[2-(2-AMINO-6,6-DISUBSTITUTED-4,4A,5,6-TETRAHYDROPYRANO[3,4-D][1,3]THIAZIN-8A(8H)-YL)-1,3-THIAZOL-4-YL] AMIDES

Pfizer Inc., New York, N...

1. A compound of Formula IwhereinR1 is selected from the group consisting of:
C1-6alkyl optionally substituted with one to three fluoro or C1-3alkoxy;
C5-9bicycloalkyl optionally substituted with one to three R4; and
a 5- to 6-membered heteroaryl, having one to four heteroatoms independently selected from N, O or S, wherein at least one of the heteroatoms is N and wherein said N is optionally substituted with R5; and wherein said 5- to 6-membered heteroaryl is optionally substituted on carbon with one to three R4;
R2 and R3 are each independently selected from C1-6alkyl or C3-7cycloalkyl; wherein the C1-6alkyl is optionally substituted with one to three fluoro or C1-3alkoxy; or R2 and R3 taken together with the carbon to which they are attached form a C3-6cycloalkyl ring or a 4- to 6-membered heterocycloalkyl ring, each of which is optionally and independently substituted with one to three fluoro, C1-3alkyl or C1-3alkoxy;
R4 at each occurrence is independently selected from the group consisting of halogen, hydroxy, cyano, C1-6alkyl, C1-6alkoxy, C3-6alkenyl, C3-6alkenyloxy, C3-6alkynyl, C3-6alkynyloxy, C1-6alkoxy-C1-6alkyl, C3-6cycloalkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C3-6cycloalkyl-C1-6alkoxy, 4- to 6-membered heterocycloalkyl and 4- to 6-membered heterocycloalkyl-C1-6alkyl; wherein said C1-6alkyl, C1-6alkoxy, C3-6alkenyl, C3-6alkenyloxy, C3-6alkynyl, C3-6alkynyloxy, C1-6alkoxy-C1-6alkyl, C3-6 cycloalkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C3-6cycloalkyl-C1-6alkoxy, 4- to 6-membered heterocycloalkyl and 4- to 6-membered heterocycloalkyl-C1-6alkyl are each optionally substituted with one to three substituents independently selected from fluoro, chloro, hydroxy, cyano, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, methoxy, fluoromethoxy, difluoromethoxy and trifluoromethoxy; and
R5 is hydrogen, C1-6alkyl, C3-6alkenyl, C3-6alkynyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, 4- to 6-membered heterocycloalkyl and 4- to 6 membered heterocycloalkyl-C1-6alkyl; wherein said C1-6alkyl, C3-6alkenyl, C3-6alkynyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, 4- to 6-membered heterocycloalkyl and 4-to 6-membered heterocycloalkyl-C1-6alkyl are each optionally substituted with one to three substituents independently selected from fluoro, chloro, hydroxy, cyano, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, methoxy, fluoromethoxy, difluoromethoxy and trifluoromethoxy; or R4 and R5 taken together can be a C3-5alkylene;
or a tautomer thereof or a pharmaceutically acceptable salt of said compound or tautomer.

US Pat. No. 10,112,957

THIAZOLYL-CONTAINING COMPOUNDS FOR TREATING PROLIFERATIVE DISEASES

Dana-Farber Cancer Instit...

1. A compound of Formula (I):or a pharmaceutically acceptable salt thereof, wherein:each instance of RA1 is independently halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORa, —N(Ra)2, —SRa, —CN, —SCN, —C(?NRa)Ra, —C(?NRa)ORa, —C(?NRa)N(Ra)2, —C(?O)Ra, —C(?O)ORa, —C(?O)N(Ra)2, —NO2, —NRaC(?O)Ra, —NRaC(?O)ORa, —NRaC(?O)N(Ra)2, —OC(?O)Ra, —OC(?O)ORa, or —OC(?O)N(Ra)2;
each instance of Ra is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of Ra are joined to form a substituted or unsubstituted, heterocyclic ring, or substituted or unsubstituted, heteroaryl ring;
k is 0, 1, 2, 3, 4, or 5;
LA is —C(?O)—NRA2— or —NRA2—C(?O)—, wherein RA2 is hydrogen, substituted or unsubstituted C1-6 alkyl, or a nitrogen protecting group;
RA3 is hydrogen, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORa, —N(Ra)2, —SRa, —CN, —SCN, —C(?NRa)Ra, —C(?NRa)ORa, —C(?NRa)N(Ra)2, —C(?O)Ra, —C(?O)ORa, —C(?O)N(Ra)2, —NO2, —NRaC(?O)Ra, —NRaC(?O)ORa, —NRaC(?O)N(Ra)2, —OC(?O)Ra, —OC(?O)ORa, or —OC(?O)N(Ra)2;
RA4 is hydrogen, substituted or unsubstituted C1-6 alkyl, or a nitrogen protecting group;
each instance of RA5 is independently halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORa, —N(Ra)2, —SRa, —CN, —SCN, —C(?NRa)Ra, —C(?NRa)ORa, —C(?NRa)N(Ra)2, —C(?O)Ra, —C(?O)ORa, —C(?O)N(Ra)2, —NO2, —NRaC(?O)Ra, —NRaC(?O)ORa, —NRaC(?O)N(Ra)2, —OC(?O)Ra, —OC(?O)ORa, or —OC(?O)N(Ra)2;
m is 0, 1, or 2;
RA6 is hydrogen, substituted or unsubstituted C1-6 alkyl, or a nitrogen protecting group; and
RA7 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heteroaryl, —C(?O)Ra, —C(?O)ORa, —C(?O)N(Ra)2, or a nitrogen protecting group;
wherein:
each substituent at a carbon atom is independently halogen, —CN, —NO2, —N3, —SO2H, —SO3H, —OH, —ORaa, —ON(Rbb)2, —N(Rbb)2, —N(Rbb)3+X?, —N(ORcc)Rbb, —SH, —SRaa, —SSRcc, —C(?O)Raa, —CO2H, —CHO, —C(ORcc)2, —CO2Raa, —OC(?O)Raa, —OCO2Raa, —C(?O)N(Rbb)2, —OC(?O)N(Rbb)2, —NRbbC(?O)Raa, —NRbbCO2Raa, —NRbbC(?O)N(Rbb)2, —C(?NRbb)Raa, —C(?NRbb)ORaa, —OC(?NRbb)Raa, —OC(?NRbb)ORaa, —C(?NRbb)N(Rbb)2, —OC(?NRbb)N(Rbb)2, —NRbbC(?NRbb)N(Rbb)2, —C(?O)NRbbSO2Raa, —NRbbSO2Raa, —SO2N(Rbb)2, —SO2Raa, —SO2ORaa, —OSO2Raa, —S(?O)Raa, —OS(?O)Raa, —Si(Raa)3, —OSi(Raa)3, —C(?S)N(Rbb)2, —C(?O)SRaa, —C(?S)SRaa, —SC(?S)SRaa, —SC(?O)SRaa, —OC(?O)SRaa, —SC(?O)ORaa, —SC(?O)Raa, —P(?O)(Raa)2, —P(?O)(ORcc)2, —OP(?O)(Raa)2, —OP(?O)(ORcc)2, —P(?O)(N(Rbb)2)2, —OP(?O)(N(Rbb)2)2, —NRbbP(?O)(Raa)2, —NRbbP(?O)(ORcc)2, —NRbbP(?O)(N(Rbb)2)2, —P(Rcc)2, —P(ORcc)2, —P(Rcc)3+X?, —P(ORcc)3+X?, —P(Rcc)4, —P(ORcc)4, —OP(Rcc)2, —OP(Rcc)3+X?, —OP(ORcc)2, —OP(ORcc)3+X?, —OP(Rcc)4, —OP(ORcc)4, —B(Raa)2, —BRaa(ORcc), C1-10 alkyl, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, heterocyclyl, C6-14 aryl, or heteroaryl, wherein each one of the alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups;
or two geminal hydrogens on a carbon atom are replaced with the group ?O, ?S, ?NN(Rbb)2, ?NNRbbC(?O)Raa, ?NNRbbC(?O)ORaa, ?NNRbbS(?O)2Raa, ?NRbb, or ?NORcc;
each substituent on a nitrogen atom is independently hydrogen, —OH, —ORaa, —N(Rcc)2, —CN, —C(?O)Raa, —C(?O)N(Rcc)2, —CO2Raa, —SO2Raa, —C(?NRbb)Raa, —C(?NRcc)ORaa, —C(?NRcc)N(Rcc)2, —SO2N(Rcc)2, —SO2Rcc, —SO2Rcc, —SO2ORcc, —SORaa, —C(?S)N(Rcc)2, —C(?O)SRcc, —C(?S)SRcc, —P(?O)(ORcc)2, —P(?O)(Raa)2, —P(?O)(N(Rcc)2)2), C1-10 alkyl, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, heterocyclyl, C6-14 aryl, or heteroaryl, wherein each one of the alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups;
each instance of the acyl is independently —C(?O)Raa, —CHO, —CO2Raa, —C(?O)N(Rbb)2, —C(?NRbb)Raa, —C(?NRbb)ORaa, —C(?NRbb)N(Rbb)2, —C(?O)NRbbSO2Raa, —C(?S)N(Rbb)2, —C(?O)SRaa, or —C(?S)SRaa;
each instance of Raa is independently C1-10 alkyl, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, heterocyclyl, C6-14 aryl, or heteroaryl, or two Raa groups are joined to form heterocyclyl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups;
each instance of Rbb is independently hydrogen, —OH, —ORaa, —N(Rcc)2, —CN, —C(?O)Raa, —C(?O)N(Rcc)2, —CO2Raa, —SO2Raa, —C(?NRcc)ORaa, —C(?NRcc)N(Rcc)2, —SO2N(Rcc)2, —SO2Rcc, —SO2Rcc, —SORaa, —C(?S)N(Rcc)2, —C(?O)SRcc, —C(?S)SRcc, —P(?O)(Raa)2, —P(?O)(ORcc)2, —P(?O)(N(Rcc)2)2), C1-10 alkyl, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, heterocyclyl, C6-14 aryl, or heteroaryl, or two Rbb groups are joined to form heterocyclyl or heteroaryl, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups;
each instance of Rcc is independently hydrogen, C1-10 alkyl, C1-10 perhaloalkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 carbocyclyl, heterocyclyl, C6-14 aryl, or heteroaryl, or two Rcc groups are joined to form heterocyclyl or heteroaryl, wherein each one of the alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rdd groups;
each instance of Rdd is independently halogen, —CN, —NO2, —N3, —SO2H, —SO3H, —OH, —ORee, —ON(Rff)2, —N(Rff)2, —N(Rff)3+X?, —N(ORee)Rff, —SH, —SRee, —SSRee, —C(?O)Ree, —CO2H, —CO2Ree, —OC(?O)Ree, —OCO2Ree, —C(?O)N(Rff)2, —OC(?O)N(Rff)2, —NRffC(?O)Ree, —NRffCO2Ree, —NRffC(?O)N(Rff)2, —C(?NRff)ORee, —C(?NRff)Ree, —OC(?NRff)ORee, —C(?NRff)N(Rff)2, —OC(?NRff)N(Rff)2, —NRffC(?NRff)N(Rff)2, —NRffSO2Ree, —SO2N(Rff)2, —SO2Ree, —SO2ORee, —OSO2Ree, —S(?O)Ree, —Si(Ree)3, —OSi(Ree)3, —C(?S)N(Rff)2, —C(?O)SRee, —C(?S)SRee, —SC(?S)SRee, —P(?O)(ORee)2, —P(?O)(Ree)2, —OP(?O)(Ree)2, —OP(?O)(ORee)2, C1-6 alkyl, C1-6 perhaloalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, heterocyclyl, C6-10 aryl, or heteroaryl, wherein each one of the alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rgg groups, or two geminal Rdd substituents are joined to form ?O or ?S;
each instance of Ree is independently C1-6 alkyl, C1-6 perhaloalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, heterocyclyl, or heteroaryl, wherein each one of the alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rgg groups;
each instance of Rff is independently hydrogen, C1-6 alkyl, C1-6 perhaloalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, heterocyclyl, C6-10 aryl, or heteroaryl, or two Rff groups are joined to form heterocyclyl or heteroaryl, wherein each one of the alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 Rgg groups;
each instance of Rgg is independently halogen, —CN, —NO2, —N3, —SO2H, —SO3H, —OH, —OC1-6 alkyl, —ON(C1-6 alkyl)2, —N(C1-6 alkyl)2, —N(C1-6 alkyl)3+X?, —NH(C1-6 alkyl)2+X?, —NH2(C1-6 alkyl)+X?, —NH3+X?, —N(OC1-6 alkyl)(C1-6 alkyl), —N(OH)(C1-6 alkyl), —NH(OH), —SH, —SC1-6 alkyl, —SS(C1-6 alkyl), —C(?O)(C1-6 alkyl), —CO2H, —CO2(C1-6 alkyl), —OC(?O)(C1-6 alkyl), —OCO2(C1-6 alkyl), —C(?O)NH2, —C(?O)N(C1-6 alkyl)2, —OC(?O)NH(C1-6 alkyl), —NHC(?O)(C1-6 alkyl), —N(C1-6 alkyl)C(?O)(C1-6 alkyl), —NHCO2(C1-6 alkyl), —NHC(?O)N(C1-6 alkyl)2, —NHC(?O)NH(C1-6 alkyl), —NHC(?O)NH2, —C(?NH)O(C1-6 alkyl), —OC(?NH)(C1-6 alkyl), —OC(?NH)OC1-6 alkyl, —C(?NH)N(C1-6 alkyl)2, —C(?NH)NH(C1-6 alkyl), —C(?NH)NH2, —OC(?NH)N(C1-6 alkyl)2, —OC(NH)NH(C1-6 alkyl), —OC(NH)NH2, -NHC(NH)N(C1-6 alkyl)2, —NHC(?NH)NH2, —NHSO2(C1-6 alkyl), —SO2N(C1-6 alkyl)2, —SO2NH(C1-6 alkyl), —SO2NH2, —SO2C1-6 alkyl, —SO2OC1-6 alkyl, —OSO2C1-6 alkyl, —SOC1-6 alkyl, —Si(C1-6 alkyl)3, —OSi(C1-6 alkyl)3—C(?S)N(C1-6 alkyl)2, C(?S)NH(C1-6 alkyl), C(?S)NH2, —C(?O)S(C1-6 alkyl), —C(?S)SC1-6 alkyl, —SC(?S)SC1-6 alkyl, —P(?O)(OC1-6 alkyl)2, —P(?O)(C1-6 alkyl)2, —OP(?O)(C1-6 alkyl)2, —OP(?O)(OC1-6 alkyl)2, C1-6 alkyl, C1-6 perhaloalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, heterocyclyl, or heteroaryl; or two geminal Rgg substituents are joined to form ?O or ?S;
X? is a counterion;
each instance of the heteroaryl and heteroaryl ring independently is 5- to 10-membered, and monocyclic or bicyclic, and has ring carbon atoms and 1 to 4 ring heteroatoms;
each instance of the heterocyclyl and heterocyclic ring independently is 3- to 10-membered; saturated or partially unsaturated; non-aromatic; and monocyclic, fused bicyclic, bridged bicyclic, or spiro bicyclic; and has ring carbon atoms and 1 to 4 ring heteroatoms;
each instance of the ring heteroatoms is independently nitrogen, oxygen, or sulfur; and
each instance of the nitrogen protecting group is independently formamide, acetamide, chloroacetamide, trichloroacetamide, trifluoroacetamide, phenylacetamide, 3-phenylpropanamide, picolinamide, 3-pyridylcarboxamide, N-benzoylphenylalanyl, benzamide, p-phenylbenzamide, o-nitophenylacetamide, o-nitrophenoxyacetamide, acetoacetamide, (N?-dithiobenzyloxyacylamino)acetamide, 3-(p -hydroxyphenyl)propanamide, 3-(o-nitrophenyl)propanamide, 2-methyl-2-(o -nitrophenoxy)propanamide, 2-methyl-2-(o-phenylazophenoxy)propanamide, 4-chlorobutanamide, 3-methyl-3-nitrobutanamide, o-nitrocinnamide, N-acetylmethionine, o -nitrobenzamide, o-(benzoyloxymethyl)benzamide, methyl carbamate, ethylcarbamate, 9-fluorenylmethyl carbamate (Fmoc), 9-(2-sulfo)fluorenylmethyl carbamate, 9-(2,7-dibromo)fluoroenylmethyl carbamate, 2,7-di-t-butyl[9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)]methyl carbamate (DBD-Tmoc), 4-methoxyphenacyl carbamate (Phenoc), 2,2,2-trichloroethyl carbamate (Troc), 2-trimethylsilylethyl carbamate (Teoc), 2-phenylethyl carbamate (hZ), 1-(1-adamantyl)-1-methylethyl carbamate (Adpoc), 1,1-dimethyl-2-haloethyl carbamate, 1,1-dimethyl-2,2-dibromoethyl carbamate (DB-t-BOC), 1,1-dimethyl-2,2,2-trichloroethyl carbamate (TCBOC), 1-methyl-1-(4-biphenylyl)ethyl carbamate (Bpoc), 1-(3,5-di-t-butylphenyl)-1-methylethyl carbamate (t-Bumeoc), 2-(2?- or 4?-pyridyl)ethyl carbamate (Pyoc), 2-(N,N-dicyclohexylcarboxamido)ethyl carbamate, t -butyl carbamate (BOC or Boc), 1-adamantyl carbamate (Adoc), vinyl carbamate (Voc), allyl carbamate (Alloc), 1-isopropylallyl carbamate (Ipaoc), cinnamyl carbamate (Coc), 4-nitrocinnamyl carbamate (Noc), 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate, alkyldithio carbamate, benzyl carbamate (Cbz), p-methoxybenzyl carbamate (Moz), p-nitobenzyl carbamate, p-bromobenzyl carbamate, p-chlorobenzyl carbamate, 2,4-dichlorobenzyl carbamate, 4-methylsulfinylbenzyl carbamate (Msz), 9-anthrylmethyl carbamate, diphenylmethyl carbamate, 2-methylthioethyl carbamate, 2-methylsulfonylethyl carbamate, 2-(p-toluenesulfonyl)ethyl carbamate, [2-(1,3-dithianyl)]methyl carbamate (Dmoc), 4-methylthiophenyl carbamate (Mtpc), 2,4-dimethylthiophenyl carbamate (Bmpc), 2-phosphonioethyl carbamate (Peoc), 2-triphenylphosphonioisopropyl carbamate (Ppoc), 1,1-dimethyl-2-cyanoethyl carbamate, m-chloro-p-acyloxybenzyl carbamate, p -(dihydroxyboryl)benzyl carbamate, 5-benzisoxazolylmethyl carbamate, 2-(trifluoromethyl)-6-chromonylmethyl carbamate (Tcroc), m-nitrophenyl carbamate, 3,5-dimethoxybenzyl carbamate, o-nitrobenzyl carbamate, 3,4-dimethoxy-6-nitrobenzyl carbamate, phenyl(o-nitrophenyl)methyl carbamate, t-amyl carbamate, S-benzyl thiocarbamate, p-cyanobenzyl carbamate, cyclobutyl carbamate, cyclohexyl carbamate, cyclopentyl carbamate, cyclopropylmethyl carbamate, p-decyloxybenzyl carbamate, 2,2-dimethoxyacylvinyl carbamate, o-(N,N-dimethylcarboxamido)benzyl carbamate, 1,1-dimethyl-3-(N,N-dimethylcarboxamido)propyl carbamate, 1,1-dimethylpropynyl carbamate, di(2-pyridyl)methyl carbamate, 2-furanylmethyl carbamate, 2-iodoethyl carbamate, isoborynl carbamate, isobutyl carbamate, isonicotinyl carbamate, p-(p?-methoxyphenylazo)benzyl carbamate, 1-methylcyclobutyl carbamate, 1-methylcyclohexyl carbamate, 1-methyl-1-cyclopropylmethyl carbamate, 1-methyl-1-(3,5-dimethoxyphenyl)ethyl carbamate, 1-methyl-1-(p-phenylazophenyl)ethyl carbamate, 1-methyl-1-phenylethyl carbamate, 1-methyl-1-(4-pyridyl)ethyl carbamate, phenyl carbamate, p-(phenylazo)benzyl carbamate, 2,4,6-tri-t-butylphenyl carbamate, 4-(trimethylammonium)benzyl carbamate, 2,4,6-trimethylbenzyl carbamate, p -toluenesulfonamide (Ts), benzenesulfonamide, 2,3,6,-trimethyl-4-methoxybenzenesulfonamide (Mtr), 2,4,6-trimethoxybenzenesulfonamide (Mtb), 2,6-dimethyl-4-methoxybenzenesulfonamide (Pme), 2,3,5,6-tetramethyl-4-methoxybenzenesulfonamide (Mte), 4-methoxybenzenesulfonamide (Mbs), 2,4,6-trimethylbenzenesulfonamide (Mts), 2,6-dimethoxy-4-methylbenzenesulfonamide (iMds), 2,2,5,7,8-pentamethylchroman-6-sulfonamide (Pmc), methanesulfonamide (Ms), ?-trimethylsilylethanesulfonamide (SES), 9-anthracenesulfonamide, 4-(4?,8?-dimethoxynaphthylmethyl)benzenesulfonamide (DNMBS), benzylsulfonamide, trifluoromethylsulfonamide, phenacylsulfonamide, phenothiazinyl-(10)-acyl, N?-p -toluenesulfonylaminoacyl, N?-phenylaminothioacyl, N-benzoylphenylalanyl, N -acetylmethionine, 4,5-diphenyl-3-oxazolin-2-one, N-phthalimide, N-dithiasuccinimide (Dts), N-2,3-diphenylmaleimide, N-2,5-dimethylpyrrole, N-1,1,4,4-tetramethyldisilylazacyclopentane adduct (STABASE), 5-substituted 1,3-dimethyl-1,3,5-triazacyclohexan-2-one, 5-substituted 1,3-dibenzyl-1,3,5-triazacyclohexan-2-one, 1-substituted 3,5-dinitro-4-pyridone, N-methylamine, N-allylamine, N-[2-(trimethylsilyl)ethoxy]methylamine (SEM), N-3-acetoxypropylamine, N-(1-isopropyl-4-nitro-2-oxo-3-pyroolin-3-yl)amine, quaternary ammonium salt, N-benzylamine, N-di(4-methoxyphenyl)methylamine, N-5-dibenzosuberylamine, N-triphenylmethylamine (Tr), N -[(4-methoxyphenyl)diphenylmethyl]amine (MMTr), N-9-phenylfluorenylamine (PhF), N -2,7-dichloro-9-fluorenylmethyleneamine, N-ferrocenylmethylamino (Fcm), N-2-picolylamino N?-oxide, N-1,1-dimethylthiomethyleneamine, N-benzylideneamine, N-p -methoxybenzylideneamine, N-diphenylmethyleneamine, N-[(2-pyridyl)mesityl]methyleneamine, N-(N?,N?-dimethylaminomethylene)amine, N,N?-isopropylidenediamine, N-p-nitrobenzylideneamine, N-salicylideneamine, N-5-chlorosalicylideneamine, N-(5-chloro-2-hydroxyphenyl)phenylmethyleneamine, N -cyclohexylideneamine, N-(5,5-dimethyl-3-oxo-1-cyclohexenyl)amine, N-borane, N -diphenylborinic acid, N-[phenyl(pentaacylchromium- or tungsten)acyl]amine, N-copper chelate, N-zinc chelate, N-nitroamine, N-nitrosoamine, amine N-oxide, diphenylphosphinamide (Dpp), dimethylthiophosphinamide (Mpt), diphenylthiophosphinamide (Ppt), dialkyl phosphoramidate, dibenzyl phosphoramidate, diphenyl phosphoramidate, benzenesulfenamide, o-nitrobenzenesulfenamide (Nps), 2,4-dinitrobenzenesulfenamide, pentachlorobenzenesulfenamide, 2-nitro-4-methoxybenzenesulfenamide, triphenylmethylsulfenamide, or 3-nitropyridinesulfenamide (Npys).

US Pat. No. 10,112,956

HETEROCYCLIC COMPOUNDS HAVING CHOLESTEROL 24-HYDROXYLASE ACTIVITY

TAKEDA PHARMACEUTICAL COM...

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

US Pat. No. 10,112,955

ISOINDOLINE, AZAISOINDOLINE, DIHYDROINDENONE AND DIHYDROAZAINDENONE INHIBITORS OF MNK1 AND MNK2

eFFECTOR Therapeutics, In...

16. A pharmaceutical composition comprising (i) a therapeutically effective amount of at least one compound according to claim 1 or a stereoisomer, a tautomer or a pharmaceutically acceptable salt thereof; (ii) in combination with a pharmaceutically acceptable carrier, diluent or excipient.

US Pat. No. 10,112,954

BICYCLIC HETEROARYL DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE

HANMI PHARM. CO., LTD., ...

7. A pharmaceutical composition comprising the compound of claim 1 as an active ingredient and a pharmaceutically acceptable carrier.

US Pat. No. 10,112,953

11,13-MODIFIED SAXITOXINS FOR THE TREATMENT OF PAIN

SITEONE THERAPEUTICS, INC...

1. A Compound of Formula (I):
where
R1 is H, OH, —OS(O)3?, —OS(O)2R5, —OC(O)R6, —NR7C(O)R7a, —OC(O)NR10R10a, —NR11R11a, —NH3+, —NR13S(O)2R13a, or —NR14C(O)NR14aR14b;
X1 is R3 and X2 is R9; or
X1 and X2 together with the —NC(O)— to which they are attached form a 5 or 6-membered ring where X1, X2, and the one or two additional ring atoms are independently selected from —C(O)—, —O—, —S—, —NR8—, and —C(R4)(R4a)— provided that only one is selected from —O—, —S—, and —NR8—; and where the 5 or 6-membered ring is optionally fused at two adjacent carbon atoms, or is optionally fused at one carbon atom and one nitrogen atom which are adjacent to each other, to a form a saturated or unsaturated 6-12 membered bicyclic ring; where the 1, 2, 3, 4, 5, or 6 additional bicyclic ring atoms are independently —CR12? or —C(R12)2—; or
X1 and X2 together with the —NC(O)— to which they are attached form 1,3-dioxo-hexahydro-1H-4,7-methanoisoindolyl;
each R4 and R4a is independently H; C1-6alkyl; or when the 6-12 membered ring is fused at a —C(R4)(R4a—, one or both of the R4 and R4a on the —C(R4)(R4a)— form a single or double bond with an adjacent ring atom;
R8 is hydrogen; C1-6alkyl; phenyl optionally substituted with 1, 2, or 3 groups independently selected from halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, nitro, and cyano; or when the 6-12 membered ring is fused at an —NR8—, the R8 forms a single bond with an adjacent ring atom;
each R12 is independently hydrogen, halo, C1-6alkyl, halo-C1-6alkyl, or aryl;
R3 is —C(O)C1-6alkyl, —C(O)OC1-6alkyl, or —C(O)phenyl where the phenyl is optionally substituted with one or two groups independently selected from halo, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, and aryl;
R5 is H, C1-6alkyl, or aryl optionally substituted with 1, 2, 3, or 4 R5a;
each R5a, when present, is independently halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, C1-6alkylthio, halo-C1-6alkylthio, C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, nitro, amino, C1-6alkylamino, di- C1-6alkylamino, phenyl, or cyano;
R9 is C1-6alkyl, C1-6alkoxy, or phenyl where the phenyl is optionally substituted with one or two groups independently selected from halo, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, and aryl;
R6 is C1-6alkyl; aryl optionally substituted with 1, 2, 3, or 4 R6a; aralkyl where the aryl is optionally substituted with 1, 2, 3, or 4 R6a; heteroaryl optionally substituted with 1, 2, 3, or 4 R6a; heterocyclic optionally substituted with 1, 2, 3, or 4 R6a; biphenyl optionally substituted on either ring with 1, 2, or 3 R6a; or cycloalkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-6alkyl and halo-C1-6alkyl;
each R6a, when present, is independently halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, nitro, C1-6alkylthio, halo-C1-6alkylthio, C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, amino, C1-6alkylamino, di-C1-6alkylamino, phenyl, or cyano;
R7 is hydrogen or C1-6alkyl;
R7a is C1-6alkyl; aryl optionally substituted with 1, 2, 3, or 4 R7b; aralkyl where the aryl is optionally substituted with 1, 2, 3, or 4 R7b; heteroaryl optionally substituted with 1, 2, 3, or 4 R7b; heterocyclic optionally substituted with 1, 2, 3, or 4 R7b; biphenyl optionally substituted on either ring with 1, 2, or 3 R7b; or cycloalkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-6alkyl and halo-C1-6alkyl;
each R7b, when present, is independently halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, nitro, C1-6alkylthio, halo-C1-6alkylthio, C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, amino, C1-6alkylamino, di-C1-6alkylamino, phenyl, or cyano;
R10 is hydrogen or C1-6alkyl;
R10a is C1-6alkyl; aryl optionally substituted with 1, 2, 3, or 4 R10b; aralkyl where the aryl is optionally substituted with 1, 2, 3, or 4 R10b; phenylcarbonyl where the phenyl is optionally substituted with 1, 2, or 3 R10b; heteroaryl optionally substituted with 1, 2, 3, or 4 R10b; heterocyclic optionally substituted with 1, 2, 3, or 4 R10b; biphenyl optionally substituted on either ring with 1, 2, 3, or 4 R10b, or cycloalkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-6alkyl and halo-C1-6alkyl;
each R10b, when present, is independently halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, nitro, C1-6alkylthio, halo-C1-6alkylthio, C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, amino, C1-6alkylamino, di-C1-6alkylamino, phenyl, or cyano;
R11 is hydrogen or C1-6alkyl;
R11a is C1-6alkyl; aryl optionally substituted with 1, 2, 3, or 4 R11b; aralkyl where the aryl is optionally substituted with 1, 2, 3, or 4 R11b; heteroaryl optionally substituted with 1, 2, 3, or 4 R11b; heterocyclic optionally substituted with 1, 2, 3, or 4 R11b; biphenyl optionally substituted on either ring with 1, 2, 3, or 4 R11b; or cycloalkyl optionally substituted with 1, 2, or 3 groups independently selected from C1-6alkyl and halo-C1-6alkyl; and
each R11b, when present, is independently halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, nitro, C1-6alkylthio, halo-C1-6alkylthio, C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, amino, C1-6alkylamino, di-C1-6alkylamino, phenyl, or cyano;
R13 is hydrogen or C1-6alkyl;
R13a is C1-6alkyl; aryl optionally substituted with 1, 2, 3, or 4 R13b; aralkyl where the aryl is optionally substituted with 1, 2, 3, or 4 R13b, heteroaryl optionally substituted with 1, 2, 3, or 4 R13b; heterocyclic optionally substituted with 1, 2, 3, or 4 R13b, biphenyl optionally substituted on either ring with 1, 2, 3, or 4 R13b; or cycloalkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-6alkyl and halo-C1-6alkyl;
each R13b, when present, is independently halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, C1-6alkylthio, halo-C1-6alkylthio, C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, nitro, amino, C1-6alkylamino, di-C1-6alkylamino, phenyl, or cyano;
R14 is hydrogen or C1-6alkyl;
R14a is hydrogen or C1-6alkyl;
R14b) is C1-6alkyl; aryl optionally substituted with 1, 2, 3, or 4 R14c; aralkyl where the aryl is optionally substituted with 1, 2, 3, or 4 R14c; heteroaryl optionally substituted with 1, 2, 3, or 4 R14c; heterocyclic optionally substituted with 1, 2, 3, or 4 R14c; biphenyl optionally substituted on either ring with 1, 2, 3, or 4 R14c; or cycloalkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-6alkyl and halo-C1-6alkyl; and
each R14c, when present, is independently halo, C1-6alkyl, halo-C1-6alkyl, hydroxy, C1-6alkoxy, halo-C1-6alkoxy, C1-6alkylthio, halo-C1-6alkylthio, C1-6alkylsulfinyl, halo-C1-6alkylsulfinyl, C1-6alkylsulfonyl, halo-C1-6alkylsulfonyl, nitro, amino, C1-6alkylamino, di-C1-6alkylamino, phenyl, or cyano; or
a pharmaceutically acceptable salt, stereoisomer, tautomer, or mixture thereof.

US Pat. No. 10,112,952

FUSED TETRA OR PENTA-CYCLIC DIHYDRODIAZEPINOCARBAZOLONES AS PARP INHIBITORS

BEIGENE, LTD., Grand Cay...

1. A method of treating a disease responsive to inhibition of PARP comprising administering to a subject in need thereof a compound of Formula (I) or a stereoisomer or a pharmaceutically acceptable salt thereof, in an amount effective to inhibit said PARP:wherein:RN is selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl, wherein each of the alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl is independently optionally substituted with at least one substituent R12;
X is selected from the group consisting of C, N, O, and S;
m and n, which may be the same or different, are each an integer of 0, 1, 2, or 3;
t is an integer of 0, 1, 2, or 3;
R1, at each occurrence, is independently selected from halogen, CN, NO2, OR9, NR9R10, NR9COR10, NR9SO2R10, CONR9R10, COOR9, SO2R9, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl, wherein each of the alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl is independently optionally substituted with at least one substituent R12;
R2 is selected from hydrogen, COR9, CONR9R10, CO2R9, SO2R9, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl, wherein each of the alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl is independently optionally substituted with at least one substituent R12;
R3, R4, R5, R6, R7 and R8, which may be the same or different, are each independently selected from hydrogen, halogen, —NR9R10, —OR9, oxo, —COR9, —CO2R9, —CONR9R10, —NR9CONR10R11, —NR9CO2R10, —NR9SO2R10, —SO2R9, alkyl, alkenyl, cycloalkyl, aryl, heterocyclyl, alkynyl, and heteroaryl, wherein each of the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, and heteroaryl is independently optionally substituted with at least one substituent R12,
or (R3 and R4), and/or (R4 and R5), and/or (R5 and R6), and/or (R6 and R7), and/or (R7 and R8), together with the atom(s) they are attached, form a 3- to 8-membered saturated, partially or fully unsaturated ring having 0, 1 or 2 heteroatoms independently selected from —NR13—, —O—, —S—, —SO— or —SO2—, and said ring is optionally substituted with at least one substituent R12,
provided that
when X is O, R5 and R6 are absent,
when X is N, R6 is absent,
when X is S, R5 and R6 are absent, or at least one of R5 and R6 is oxo,
when one of R3 and R4 is oxo, the other is absent,
when one of R7 and R8 is oxo, the other is absent, and
when X is C and one of R5 and R6 is oxo, the other is absent;
R9, R10, and R11, which may be the same or different, are each selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl, wherein each of the alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl is independently optionally substituted with at least one substituent R12;
R12 is selected from CN, halogen, haloalkyl, NO2, —NR?R?, —OR?, oxo, —COR?, —CO2R?, —CONR?R?, —NR?CONR?R??, —NR?CO2R?, —NR?SO2R?, —SO2R?, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl, wherein R?, R?, and R?? are independently selected from hydrogen, haloalkyl, alkyl, arylalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, and heteroaryl, or (R? and R?), and/or (R? and R??) together with the atoms to which they are attached, form a 3- to 8-membered saturated, partially or fully unsaturated ring having 0, 1 or 2 additional heteroatoms independently selected from —NR13—, —O—, —S—, —SO— and —SO2—; and
R13 is selected from hydrogen, alkyl, cycloalkyl, aryl, heteroaryl, and heterocyclyl,
wherein the cycloalkyl is a hydrocarbon group selected from saturated and partially unsaturated cyclic hydrocarbon groups, comprising monocyclic, bicyclic and tricyclic groups, and comprising from 3 to 12 carbon atoms;
wherein the heteroaryl is a group selected from:
5- to 7-membered aromatic, monocyclic rings comprising at least one heteroatom selected from N, O, and S, with the remaining ring atoms being carbon;
8- to 12-membered bicyclic rings comprising at least one heteroatom selected from N, O, and S, with the remaining ring atoms being carbon and wherein at least one ring is aromatic and at least one heteroatom is present in the aromatic ring; and
11- to 14-membered tricyclic rings comprising at least one heteroatom selected from N, O, and S, with the remaining ring atoms being carbon and wherein at least one ring is aromatic and at least one heteroatom is present in an aromatic ring; and
wherein the heterocyclyl is a ring selected from 4- to 12-membered monocyclic, bicyclic and tricyclic, saturated and partially unsaturated rings, comprising at least one carbon atoms in addition to at least one heteroatom selected from oxygen, sulfur, and nitrogen,
wherein the disease is selected from ovarian cancer or breast cancer.

US Pat. No. 10,112,951

PDE1 INHIBITOR

Eli Lilly and Company, I...

1. A method of treating chronic kidney disease in a patient, comprising administering to a patient in need thereof an effective amount of a compound of the formula:

US Pat. No. 10,112,950

SUBSTITUTED IMIDAZO[1,2-A]PYRAZINES AS LSD1 INHIBITORS

Incyte Corporation, Wilm...

1. A method for inhibiting lysine specific demethylase-1 activity in a patient, comprising administering to the patient a therapeutically effective amount of a compound of Formula I:or a pharmaceutically acceptable salt thereof, wherein:Ring A is C6-10 aryl or 5-10 membered heteroaryl comprising carbon and 1, 2, 3, or 4 heteroatoms selected from N, O, and S, wherein said C6-10 aryl and 5-10 membered heteroaryl are each optionally substituted by 1, 2, 3, or 4 substituents independently selected from RA;
Ring B is C6-10 aryl; 5-10 membered heteroaryl comprising carbon and 1, 2, 3 or 4 heteroatoms selected from N, O, and S; C3-10 cycloalkyl; or 4-10 membered heterocycloalkyl comprising carbon and 1, 2, 3 or 4 heteroatoms selected from N, O, and S; wherein said C6-10 aryl, 5-10 membered heteroaryl, C3-10 cycloalkyl, and 4-10 membered heterocycloalkyl are each optionally substituted by 1, 2, 3, or 4 substituents independently selected from RB;
R1 is halo, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, Cy1, CN, 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, C(?NRe1)Rb1, C(?NRe1)NRc1Rd1, NRc1C(?NRe1)NRc1Rd1, NRc1S(O)Rb1, NRc1S(O)2Rb1, NRc1S(O)2NRc1Rd1, S(O)Rb1, S(O)NRc1Rd1, S(O)2Rb1, or S(O)2NRc1Rd1; wherein said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy1, halo, CN, OH, 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, C(?NRe1)Rb1, C(?NRe1)NRc1Rd1, NRc1C(?NRe1)NRc1Rd1, NRc1S(O)Rb1, NRc1S(O)2Rb1, NRc1S(O)2NRc1Rd1, S(O)Rb1, S(O)NRc1Rd1, S(O)2Rb1, and S(O)2NRc1Rd1;
R2 and R3 are each independently selected from H, halo, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, Cy2, CN, 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, C(?NRe2)Rb2, C(?NRe2)NRc2Rd2, NRc2C(?NRe2)NRc2Rd2, NRc2S(O)Rb2, NRc2S(O)2Rb2, NRc2S(O)2NRc2Rd2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2, and S(O)2NRc2Rd2; wherein said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy2, halo, CN, 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, C(?NRe2)Rb2, C(?NRe2)NRc2Rd2, NRc2C(?NRe2)NRc2Rd2, NRc2S(O)Rb2, NRc2S(O)2Rb2, NRc2S(O)2NRc2Rd2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2, and S(O)2NRc2Rd2;
each RA is independently selected from halo, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, CN, NO2, ORa4, SRa4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4C(O)Rb4, NRc4C(O)ORa4, NRc4C(O)NRc4Rd4, C(?NRe4)Rb4, C(?NRe4)NRc4Rd4, NRc4C(?NRe4)NRc4Rd4, NRc4S(O)Rb4, NRc4S(O)2Rb4, NRc4S(O)2NRc4Rd4, S(O)Rb4, S(O)NRc4Rd4, S(O)2Rb4, and S(O)2NRc4Rd4, wherein said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl are each optionally substituted by 1, 2, or 3, substituents independently selected from halo, C1-6 haloalkyl, CN, NO2, ORa4, SRa4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4C(O)Rb4, NRc4C(O)ORa4, NRc4C(O)NRc4Rd4, C(?NRe4)Rb4, C(?NRe4)NRc4Rd4, NRc4C(?NRe4)NRc4Rd4, NRc4S(O)Rb4, NRc4S(O)2Rb4, NRc4S(O)2NRc4Rd4, S(O)Rb4, S(O)NRc4Rd4, S(O)2Rb4, and S(O)2NRc4Rd4;
each RB is independently selected from Cy3, halo, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 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, C(?NRe5)Rb5, C(?NRe5)NRc5Rd5, NRc5C(?NRe5)NRc5Rd5, NRc5S(O)Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, and S(O)2NRc5Rd5, wherein said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl are each optionally substituted by 1, 2, or 3 substituents independently selected from Cy3, halo, C1-6 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, C(?NRe5)Rb5, C(?NRe5)NRc5Rd5, NRc5C(?NRe5)NRc5Rd5, NRc5S(O)Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, and S(O)2NRc5Rd5;
each Cy1, Cy2, Cy3, and Cy4 is independently selected from C6-10 aryl, C3-10 cycloalkyl, 5-10 membered heteroaryl, and 4-10 membered heterocycloalkyl, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from RCy;
each RCy is independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, phenyl, C3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C1-4 alkyl-, C3-7 cycloalkyl-C1-4 alkyl-, (5-6 membered heteroaryl)-C1-4 alkyl-, and (4-7 membered heterocycloalkyl)-C1-4 alkyl-, CN, NO2, ORa6, SRa6, C(O)Rb6, C(O)NRc6Rd6, C(O)ORa6, OC(O)Rb6, OC(O)NRc6Rd6, C(?NRe6)NRc6Rd6, NRc6C(?NRe6)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, and S(O)2NRc6Rd6, wherein said C1-4 alkyl, C2-6 alkenyl, C2-6 alkynyl, phenyl, C3-7 cycloalkyl, 5-6 membered heteroaryl, 4-7 membered heterocycloalkyl, phenyl-C1-4 alkyl-, C3-7 cycloalkyl-C1-4 alkyl-, (5-6 membered heteroaryl)-C1-4 alkyl-, and (4-7 membered heterocycloalkyl)-C1-4 alkyl- are each optionally substituted by 1, 2, or 3 substituents independently selected from C1-6 alkyl, C1-4 haloalkyl, C1-6 cyanoalkyl, halo, CN, NO2, ORa6, SRa6, C(O)Rb6, C(O)NRc6Rd6, C(O)ORa6, OC(O)Rb6, OC(O)NRc6Rd6, C(?NRe6)NRc6Rd6, NRc6C(?NRe6)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, and S(O)2NRc6Rd6;
each Ra1 is independently selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, and Cy4; wherein said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl are each optionally substituted with 1, 2, or 3 substituents independently selected from Cy4, halo, CN, ORa3, SRa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)ORa3, NRc3C(O)NRc3Rd3, C(?NRe3)Rb3, C(?NRe3)NRc3Rd3, NRc3C(?NRe3)NRc3Rd3, NRc3S(O)Rb3, NRc3S(O)2Rb3, NRc3S(O)2NRc3Rd3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3, and S(O)2NRc3Rd3;
each Rb1, Rc1, and Rd1 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-, 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, 4, or 5 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
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, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
each Ra2, Rb2, Rc2, and Rd2 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-, 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, 4, or 5 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
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, phenyl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NR7S(O)2NRc7Rd7, and S(O)2NRc7Rd7, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, phenyl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
each Ra3, Rb3, Rc3, and Rd3 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-, 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, 4, or 5 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
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, phenyl, 5-6 membered heteroaryl, C1-6 haloalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, phenyl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
each Ra4, Rb4, Rc4, and Rd4 is independently selected from H, C1-6 alkyl, C1-4 haloalkyl, C2-6 alkenyl, and C2-6 alkynyl, wherein said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
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, C1-6 haloalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
each Ra5, Rb5, Rc5, and Rd5 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-, 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, 4, or 5 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
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, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7, wherein said C1-6 alkyl, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, C6-10 aryl, and 5-6 membered heteroaryl are each optionally substituted by 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
each Ra6, Rb6, Rc6, and Rd6 is independently selected from H, C1-6 alkyl, C1-4 haloalkyl, C2-6 alkenyl, and C2-6 alkynyl, wherein said C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
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, C1-6 haloalkyl, halo, CN, ORa7, SRa7, C(O)Rb7, C(O)NRc7Rd7, C(O)ORa7, OC(O)Rb7, OC(O)NRc7Rd7, NRc7Rd7, NRc7C(O)Rb7, NRc7C(O)NRc7Rd7, NRc7C(O)ORa7, C(?NRe7)NRc7Rd7, NRc7C(?NRe7)NRc7Rd7, S(O)Rb7, S(O)NRc7Rd7, S(O)2Rb7, NRc7S(O)2Rb7, NRc7S(O)2NRc7Rd7, and S(O)2NRc7Rd7;
each Ra7, Rb7, Rc7, and Rd7 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 are each 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, and C1-4 haloalkoxy; and
each Re1, Re2, Re3, Re4, Re5, Re6, and Re7 is independently selected from H, C1-4 alkyl, and CN.

US Pat. No. 10,112,949

6,7-DIHYDROPYRAZOLO[1,5-A]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS

Janssen Pharmaceutica NV,...

1. A compound of Formula (I)
or a stereoisomeric form thereof, wherein
R1 is phenyl or 2-pyridinyl, each of which is optionally substituted with one or more substituents each independently selected from the group consisting of halo, C1-4alkyl, monohalo-C1-4alkyl, polyhalo-C1-4alkyl, —C1-4alkyl-OH, —CN, —C1-4alkyl-O—C1-4alkyl, C3-7cycloalkyl, —O—C1-4alkyl, monohalo-C1-4alkyloxy, polyhalo-C1-4alkyloxy, SF5, C1-4alkylthio, monohalo-C1-4alkylthio and polyhalo-C1-4alkylthio;
R2 is phenyl or pyridinyl, each of which is optionally substituted with one or more substituents each independently selected from the group consisting of halo, C1-4alkyl, monohalo-C1-4alkyl, polyhalo-C1-4alkyl, —OH, —O—C1-4alkyl, —C1-4alkyl-O—C1-4alkyl, monohalo-C1-4alkyloxy, polyhalo-C1-4alkyloxy, —C1-4alkyl-OH and NR5aR5b;
wherein R5a and R5b are each independently selected from the group consisting of hydrogen or C1-4alkyl;
R3 is selected from the group consisting of hydrogen or C1-4alkyl;
R4 is selected from the group consisting of hydrogen, C1-4alkyl, monohalo-C1-4alkyl, polyhalo-C1-4alkyl, —C1-4alkyl-O—C1-4alkyl and —C1-4alkyl-OH;
or a N-oxide, or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,112,948

BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS

The Board of Regents of t...

1. A compound according to Formula I-g
wherein
R1 is selected from the group consisting of

n=0, 1, or 2;
m=0 or 1;
R2 and R3 can be attached at any available position on the aromatic ring and are independently selected from the group consisting of H, D, F, Cl, CF3, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 hydroxyalkyl, cycloalkyl, OR, N(R)2, NO2, N3, NH—C(O)—R, CN, C(O)R, C(O)OR, C(O)N(R)2, SR, alkylacyl, and arylacyl;
Each R is independently selected from the group consisting of H, C1-3 alkyl, propargyl, and phenyl;
R4 and R5 are independently selected from the group consisting of H, C1-6 alkyl optionally substituted with N(R)2, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 hydroxyalkyl, phenyl optionally substituted with R3, and CH2OC(O)-phenyl optionally substituted with R3;
R6 and R7 are independently selected from the group consisting of H, C1-3 alkyl, and C(O)OMe3;
such that all possible stereoisomers, including optically active isomers, are included whenever stereogenic centers are present;
or a pharmaceutically acceptable salt, prodrug, active metabolite, or solvate thereof.

US Pat. No. 10,112,947

SUBSTITUTED 6-AMINOPURINES FOR TARGETING HSP90

Duke University, Durham,...

1. A compound of formula (I):wherein:A is a heat shock protein 90 binding component of formula (III):

wherein:
R is alkylenyl or heteroalkylenyl;
each Y1 is independently —CH or —N;
each Z1 is taken together with the carbon atoms to which they are attached to form a heterocyclic ring;
Z2 is —H or halo;
Z3 is —CH2—, —S—, —O—or —NH—;
Z4 is —H or halo; and
is the point of attachment in formula (I);X1 is —NH—, —O—, —S—, —C(O)—or —S(O)2—;
L is a divalent linker of the following formula:
—(CH2)m—(OCH2CH2)n—O—(CH2)p—,
wherein:
m is 2 or 3;
n is 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20; and
p is 2 or 3;
X2 is —NR—, —O—, —S—, —C(O)—or —S(O)2—;
R is —H or a detection moiety; and
B is a detection moiety, an anti-cancer agent, or a heat shock protein 90 binding component of formula (II):

wherein:
R1 is —H or —C1-8-alkyl;
R2 is —H or —C1-8-alkyl;
Y is —CR3 or —N;
R3 is —H, —F or —OCH3;
R4 is —H, —F or —OCH3;
R5 is —H, —F or —OCH3;
R6 is —C1-8-alkyl, —C2-8-alkenyl, —C2-8-alkynyl, —C3-8-cycloalkenyl, —C3-8-cycloalkenyl-C1-8-alkyl, —C3-8-cycloalkyl, —C3-8-cycloalkyl-C1-8-alkyl, aryl, aryl-C1-8-alkyl, halo-C1-8-alkyl, heteroaryl, heteroaryl-C1-8-alkyl, heterocyclyl, heterocyclyl-C1-8-alkyl, or hydroxy-C1-8-alkyl;
R7 is —H or —C1-8-alkyl;
R8 is —H or —C1-8-alkyl; or
R7 and R8, taken together with the carbon atom to which they are attached, form a —C3-8-cycloalkyl;
X is —CR9 or —N;
R9 is —H or —C1-8-alkyl; and
is the point of attachment in formula (I); orB is a detection moiety, an anti-cancer agent, or a heat shock protein 90 binding component of formula (III):

wherein:
R is alkylenyl or heteroalkylenyl;
each Y1 is independently —CH or —N;
each Z1 is taken together with the carbon atoms to which they are attached to form a heterocyclic ring;
Z2 is —H or halo;
Z3 is —CH2—, —S—, —0—or —NH—;
Z4 is —H or halo; and
is the point of attachment in formula (I);wherein each detection moiety independently comprises a fluorophore or a radioactive compound;
wherein the fluorophore is a fluorescein, a rhodamine, a coumarin, a cyanine or a boron-dipyrromethene;
wherein the radioactive compound is a radioisotope; and
wherein the anti-cancer agent is an alkylating agent, an anti-epidermal growth factor receptor antibody, an anti-Her-2 antibody, an antimetabolite, a vinca alkaloid, an anthracycline, a platinum-based agent, a topoisomerase inhibitor, a taxane, an anti-cancer antibiotic, an immune cell antibody, an interferon, an interleukin, a heat shock protein 90 inhibitor, an anti-androgen, an anti-estrogen, an antihypercalcemia agent, an apoptosis inducer, an aurora kinase inhibitor, a Bruton's tyrosine kinase inhibitor, a calcineurin inhibitor, a Ca2+-calmodulin-dependent protein kinase II inhibitor, a CD45 tyrosine phosphatase inhibitor, a cell division cycle 25 phosphatase inhibitor, a checkpoint kinase inhibitor, a cyclooxygenase inhibitor, a cRAF kinase inhibitor, a cyclin dependent kinase inhibitor, a cysteine protease inhibitor, a deoxyribonucleic acid intercalator, a deoxyribonucleic acid strand breaker, an E3 ligase inhibitor, an epidermal growth factor pathway inhibitor, a farnesyltransferase inhibitor, a fetal liver kinase-1 inhibitor, a glycogen synthase kinase-3 inhibitor, a histone deacetylase inhibitor, an I-kappa B-alpha kinase inhibitor, an imidazotetrazinone, an insulin tyrosine kinase inhibitor, a c-Jun N-terminal kinase inhibitor, a mitogen-activated protein kinase inhibitor, a mouse double minute 2 inhibitor, an MEK inhibitor, a matrix metalloproteinase inhibitor, a mammalian target of rapamycin inhibitor, a nerve growth factor receptor tyrosine kinase inhibitor, a p38 mitogen-activated protein kinase inhibitor, a p56 tyrosine kinase inhibitor, a platelet-derived growth factor pathway inhibitor, a phosphatidylinositol 3-kinase inhibitor, a phosphatase inhibitor, a protein phosphatase inhibitor, a protein kinase C inhibitor, a protein kinase C delta kinase inhibitor, a polyamine synthesis inhibitor, a protein tyrosine phosphatase 1B inhibitor, a protein tyrosine kinase inhibitor, an SRC family tyrosine kinase inhibitor, a spleen tyrosine kinase inhibitor, a Janus tyrosine kinase inhibitor, a retinoid, a ribonucleic acid polymerase II elongation inhibitor, a serine/threonine kinase inhibitor, a sterol biosynthesis inhibitor, a vascular endothelial growth factor pathway inhibitor, alitretinon, altretamine, aminopterin, aminolevulinic acid, amsacrine, asparaginase, atrasentan, bexarotene, carboquone, demecolcine, efaproxiral, elsamitrucin, etoglucid, a Gliadel implant, hydroxycarbamide, leucovorin, lonidamine, lucanthone, masoprocol, methyl aminolevulinate, mitoguazone, mitotane, oblimersen, omacetaxine, pegaspargase, porfimer sodium, prednimustine, sitimagene ceradenovec, talaporfin, temoporfin, trabectedin or verteporfin.

US Pat. No. 10,112,946

COMPOSITION

GlaxoSmithKline LLC, Wil...

1. A pharmaceutical dosage form comprising Compound (I):or a pharmaceutically acceptable salt thereof, and means for providing a metered-dose of Compound (I), or a pharmaceutically acceptable salt thereof, which provides about 10 nanogrammes of Compound (I) per actuation of the metering means.

US Pat. No. 10,112,945

FUSED QUINOLINE COMPUNDS AS PI3K, MTOR INHIBITORS

1. A compound of formula I
wherein
Q1 and Q2 are independently selected from an aryl, a 5-6 membered heterocyclyl or a 9-11 membered bicycloheterocyclyl;
Z is N or C—R;
R and R1, when present, are independently selected from H, halogen, halogenC1-C6alkyl, —C1-C6alkyl, —OR7, —NR7R8, or are not present;
wherein when R and R1 are not present Q1 is a halogen;
R2 and R3 are independently selected from H, halogen, —OH, —C1-C6alkyl, —C1-C6alkoxyl, —C1-C6alkenyl or —C1-C6alkynyl;
R7 and R8 are independently selected from H, halogen, —C1-C6alkyl, —C1-C6alkylOH, —C1-C6alkoxyl, —C1-C6alkylNR4R5, —C(?O)C1-C6alkyl, —C(?O)C1-C6alkyl-R4R5, —C(?O)C1-C6alkylOH, —C(?O)C1-C6alkoxyl, —C(?O)C1-C6alkylNR4R5, —C(?O)OC1-C6alkyl, —C(?O)OC1-C6alkylOH, —C(?O)OC1-C6alkoxyl, —C(?O)OC1-C6alkylNR4R5, —C(?O)NR4C1-C6alkyl, —C(?O)NR4C1-C6al-kylOH, —C(?O)NR4C1-C6alkoxyl, —C(?O)NR4C1-C6alkylNR4R5;
R4 and R5 are independently selected from H, halogen, halogenC1-C6alkyl, —C1-C6alkyl, —OH, —C1-C6alkoxyl, cycloalkyl; or both R4 and R5 can be combined together to form a 3-8 membered saturated or unsaturated ring that can be aliphatic cyclyl or heterocyclyl;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,112,944

HETEROCYCLIC COMPOUNDS USEFUL AS INHIBITORS OF TNF

Bristol-Myers Squibb Comp...

1. A compound of Formula (I)
or a salt thereof, wherein:
X is CR6 or N;
W is:
(i) —(CR3R3)1-4—; or
(ii) —(CR3R3)x—Y—(CR3R3)y—;
each Y is independently O, NR4, or S(O)p;
x is zero, 1, or 2;
y is 1, 2, or 3, provided that (x+y) is 1, 2, or 3;
R1 is C2-6 alkenyl substituted with zero to 6 R1a, C2-6 alkynyl substituted with zero to 4 R1a, —(CRgRg)r(3-14 membered carbocyclyl substituted with zero to 3 R1a), —(CRgRg)r(aryl substituted with zero to 3 R1a), —(CRgRg)r(5-7 membered heterocyclyl substituted with zero to 3 R1a), or —(CRgRg)r(mono- or bicyclic heteroaryl substituted with zero to 3 R1a);
R2 is H, halo, —CN, —CF3, —OCF3, —NO2, C1-6 alkyl substituted with zero to 6 R1a, —(CRgRg)rORe, —(CRgRg)rNRcRc, —(CRgRg)rS(O)pRb, —(CRgRg)r(3-14 membered carbocyclyl substituted with zero to 3 R1a), —(CRgRg)r(aryl substituted with zero to 3 R1a), —(CRgRg)r(5-7 membered heterocyclyl substituted with zero to 3 R1a), or —(CRgRg)r(monocyclic heteroaryl substituted with zero to 3 R1a);
each R3 is independently H, halo, —CN, —OH, —OCF3, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, —(CRgRg)rC(O)Rb, —(CRgRg)rC(O)ORb, —(CRgRg)rC(O)NRcRc, —(CRgRg)rORe, —(CRgRg)rOC(O)Rb, —(CRgRg)rOC(O)NRcRc, —(CRgRg)rOC(O)ORd, —(CRgRg)rNRcRc, —(CRgRg)rNRbC(O)Rd, —(CRgRg)rNRbC(O)ORd, —(CRgRg)rNRbC(O)NRcRc, —(CRgRg)rNRbS(O)pRd, —(CRgRg)rS(O)pRb, —(CRgRg)rS(O)pNRcRc, —(CRgRg)r(3-14 membered carbocyclyl substituted with zero to 3 R1a), —(CRgRg)r(aryl substituted with zero to 3 R1a), —(CRgRg)r(5-7 membered heterocyclyl substituted with zero to 3 R1a), or —(CRgRg)r(mono- or bicyclic heteroaryl substituted with zero to 3 R1a); or two R3 along with the carbon atom to which they are attached form C?O, C?NORb, a spirocarbocyclyl group, or a spiroheterocyclyl group;
each R4 is independently H, C1-6 alkyl substituted with zero to 6 R1a, C3-7 cycloalkyl substituted with zero to 6 R1a, —C(O)Rb, —C(O)NRcRc, —C(O)ORb, —S(O)2Rb, —S(O)2NRcRc, —S(O)2ORb, —(CRgRg)r(3-14 membered carbocyclyl substituted with zero to 3 R1a), —(CRgRg)r(aryl substituted with zero to 3 R1a), —(CRgRg)r(5-7 membered heterocyclyl substituted with zero to 3 R1a), or —(CRgRg)r(monocyclic heteroaryl substituted with zero to 3 R1a);
R5 is —(CRgRg)r(3-14 membered carbocyclyl substituted with zero to 3 R1a), —(CRgRg)r(aryl substituted with zero to 3 R1a), —(CRgRg)r(5-10 membered heterocyclyl substituted with zero to 3 R1a), or —(CRgRg)r(mono- or bicyclic heteroaryl substituted with zero to 3 R1a);
R6 is H, halo, or —CN;
R7 is H, halo, —CN, C1-6 alkyl, or C1-3 alkoxy;
each R1a is independently F, Cl, —CN, C1-6 alkyl substituted with zero to 6 Ra, C3-6 cycloalkyl substituted with zero to 6 Ra, C1-3 alkoxy substituted with zero to 6 Ra, C1-3 haloalkoxy, heterocycloalkyl substituted with zero to 6 Ra, aryl substituted with zero to 6 Ra, mono- or bicyclic heteroaryl substituted with zero to 6 Ra, —C(O)Rb, —C(O)ORb, —C(O)NRcRc, —OC(O)Rb, —OC(O)NRcRc, —OC(O)ORd, —NRcRc, —NRbC(O)Rd, —NRbC(O)ORd, —NRbS(O)pRd, —NRbC(O)NRcRc, —NRbS(O)pNRcRc, —S(O)pRb, —S(O)pNRcRc, or —C(O)NRb(CH2)1-3NRcRc;
each Ra is independently halo, —CN, —OH, —NH2, C1-3 alkyl, C1-3 fluoroalkyl, C2-4 alkenyl, C2-4 alkynyl, C1-3 alkoxy, C1-3 fluoroalkoxy, —C(O)OH, —C(O)(C1-3 alkyl), —C(O)O(C1-4 alkyl), —OC(O)(C1-3 alkyl), —NH(C1-3 alkyl), —N(C1-3 alkyl)2, —C(O)NH(C1-3 alkyl), —OC(O)NH(C1-3 alkyl), —NHC(O)NH(C1-3 alkyl), —C(?NH)(NH2), C3-7 carbocyclyl, aryl, 5-7 membered heterocyclyl, mono- or bicyclic heteroaryl, —O(aryl), —O(benzyl), —O(heterocyclyl), —S(C1-3 alkyl), —S(aryl), —S(heterocyclyl), —S(O)(aryl), —S(O)(heterocyclyl), —S(O)2(aryl), —S(O)2(heterocyclyl), —NHS(O)2(aryl), —NHS(O)2(heterocyclyl), —NHS(O)2NH(aryl), —NHS(O)2NH(heterocyclyl), —NH(aryl) —NH(heterocyclyl), —NHC(O)(aryl), —NHC(O)(C1-3 alkyl), —NHC(O)(heterocyclyl), —OC(O)(aryl), —OC(O)(heterocyclyl), —NHC(O)NH(aryl), —NHC(O)NH(heterocyclyl), —OC(O)O(C1-3 alkyl), —OC(O)O(aryl), —OC(O)O(heterocyclyl), —OC(O)NH(aryl), —OC(O)NH(heterocyclyl), —NHC(O)O(aryl), —NHC(O)O(heterocyclyl), —NHC(O)O(C1-3 alkyl), —C(O)NH(aryl), —C(O)NH(heterocyclyl), —C(O)O(aryl), —C(O)O(heterocyclyl), —N(C1-3 alkyl)S(O)2(aryl), —N(C1-3 alkyl)S(O)2(heterocyclyl), —N(C1-3 alkyl)S(O)2NH(aryl), —N(C1-3 alkyl)S(O)2NH(heterocyclyl), —N(C1-3 alkyl)(aryl), —N(C1-3 alkyl)(heterocyclyl), —N(C1-3 alkyl)C(O)(aryl), —N(C1-3 alkyl)C(O)(heterocyclyl), —N(C1-3 alkyl)C(O)NH(aryl), —(CH2)0-3C(O)NH(heterocyclyl), —OC(O)N(C1-3 alkyl)(aryl), —OC(O)N(C1-3 alkyl)(heterocyclyl), —N(C1-3 alkyl)C(O)O(aryl), —N(C1-3 alkyl)C(O)O(heterocyclyl), —C(O)N(C1-3 alkyl)(aryl), —C(O)N(C1-3 alkyl)(heterocyclyl), —NHS(O)2N(C1-3 alkyl)(aryl), —NHS(O)2N(C1-3 alkyl)(heterocyclyl), —NHP(O)2N(C1-3 alkyl)(aryl), —NHC(O)N(C1-3 alkyl)(aryl), —NHC(O)N(C1-3 alkyl)(heterocyclyl), —N(C1-3 alkyl)S(O)2N(C1-3 alkyl)(aryl), —N(C1-3 alkyl)S(O)2N(C1-3 alkyl)(heterocyclyl), —N(C1-3 alkyl)C(O)N(C1-3 alkyl)(aryl), —N(C1-3 alkyl)C(O)N(C1-3 alkyl)(heterocyclyl), or —Si(C1-3 alkyl)3;
each Rb is independently H, C1-6 alkyl substituted with zero to 6 Rf, C3-7 cycloalkyl substituted with zero to 6 Rf, heterocycloalkyl substituted with zero to 6 Rf, aryl substituted with zero to 3 Rf, or mono- or bicyclic heteroaryl substituted with zero to 3 Rf;
each Rc is independently H, C1-6 alkyl substituted with zero to 6 Rf, C3-7 cycloalkyl substituted with zero to 6 Rf, heterocycloalkyl substituted with zero to 6 Rf, aryl substituted with zero to 3 Rf, or mono- or bicyclic heteroaryl substituted with zero to 3 Rf; or when attached to the same nitrogen, two Rc along with the nitrogen atom to which they are attached form 4-8 membered heterocyclic ring optionally substituted with Rg;
each Rd is independently H, C1-6 alkyl substituted with zero to 6 Rf, C3-7 cycloalkyl substituted with zero to 6 Rf, heterocycloalkyl substituted with zero to 6 Rf, aryl substituted with zero to 3 Rf, or mono- or bicyclic heteroaryl substituted with zero to 3 Rf;
each Re is independently H, C1-6 alkyl substituted with zero to 6 Rf, C1-3 haloalkyl, C3-7 cycloalkyl substituted with zero to 6 Rf, heterocycloalkyl substituted with zero to 6 Rf, aryl substituted with zero to 3 Rf, or mono- or bicyclic heteroaryl substituted with zero to 3 Rf;
each Rf is independently H, halo, —OH, —CN, C1-6 alkyl substituted with zero to 6 Ra, C1-3 alkoxy, C3-7 cycloalkyl substituted with zero to 6 Ra, heterocycloalkyl substituted with zero to 6 Ra, aryl substituted with zero to 3 Ra, or mono- or bicyclic heteroaryl substituted with zero to 3 Ra;
each Rg is independently H, F, —OH, —CN, C1-3 alkyl, —CF3, or phenyl;
each p is independently zero, 1, or 2; and
each r is independently zero, 1, 2, 3, or 4.

US Pat. No. 10,112,943

SUBSTITUTED IMIDAZOLES AS GAMMA SECRETASE MODULATORS

Janssen Pharmaceutica NV,...

8. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and, as active ingredient, a therapeutically effective amount of a compound according to claim 1.

US Pat. No. 10,112,941

TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS

Bristol-Myers Squibb Comp...

1. A method for treating cancer in a subject in need thereof, comprising administering an effective amount of a compound, of the formula
or a pharmaceutically acceptable salt thereof,
in combination with the administration of a therapeutically effective amount of one or more immuno-oncology agents.

US Pat. No. 10,112,940

HISTONE DEMETHYLASE INHIBITORS

Celgene Quanticel Researc...

1. A method of treating a histone demethylase-associated esophageal and breast cancer in a subject comprising administering a therapeutically effective dose of a compound of Formula (IIIa)
wherein the compound of Formula (IIIa) includes pharmaceutically acceptable salts thereof, wherein:
X is halogen and n is 0 or 1;
Y is hydrogen or C1-C3alkyl;
Z is halogen, —OH, —NH2, —CN, —SO2, CF3, alkyl, alkoxy, alkylamino, optionally substituted 3 membered carbocyclyl, optionally substituted 5-7 membered heterocyclyl comprising 1-2 heteroatoms selected from N or O, or 6 membered heteroaryl comprising 1 oxygen; and m is 0, 1, or 2.

US Pat. No. 10,112,939

TIED-BACK BENZAMIDE DERIVATIVES AS POTENT ROCK INHIBITORS

Bristol-Myers Squibb Comp...

1. A compound of formula (IV):
or an enantiomer, a diastereomer, a stereoisomer, or a pharmaceutically acceptable salt thereof,
wherein:
R3 is independently selected from CN, C1-4 alkyl substituted with 0-3 Re, and —ORb;
R8 is independently selected from F, C1-4 alkyl substituted with 0-3 Re, —(CH2)rORb, —(CH2)rC(?O)Rb, —NRaRa, —C(?O)NRaRa, and —C(?O)ORb;
R9 is independently selected from F, Cl, Br, C1-4 alkyl,
nitro, —S(O)pRc, —S(O)pNRaRa, —ORb, —NRaRa, —C(?O)ORb, —(CH2)rC(?O)Rb, —C(?O)NRaRa, —(CH2)r-c ycloalkyl, —(CH2)r-heterocyclyl, —(CH2)r-aryl, and —(CH2)r-heteroaryl, wherein said alkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is substituted with 0-4 Re;
Ra, at each occurrence, is independently selected from H, CN, C1-6 alkyl substituted with 0-5 Re, —(CH2)r—C3-6cycloalkyl substituted with 0-5 Re, —(CH2)r-aryl 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;
Re, at each occurrence, is independently selected from C1-6 alkyl substituted with 0-5 Rf, C2-6 alkenyl, C2-6 alkynyl, —(CH2)r—C3-6 cycloalkyl, F, Cl, Br, CN, NO2, ?O, CO2H, —(CH2)rORf, S(O)pRf, S(O)pNRfRf, and —(CH2)rNRfRf;
Rf, at each occurrence, is independently selected from H, F, Cl, Br, CN, OH, C1-5 alkyl, C3-6 cycloalkyl, and phenyl, or Rf and Rf together with the nitrogen atom to which they are both attached form a heterocyclic ring optionally substituted with C1-4alkyl;
p, at each occurrence, is independently selected from zero, 1, and 2; and
r, at each occurrence, is independently selected from zero, 1, 2, 3, and 4;
provided that R3 is not OPh.

US Pat. No. 10,112,937

P2X7 MODULATORS AND METHODS OF USE

Janssen Pharmaceutica NV,...

36. A pharmaceutical composition, comprising:(a) a therapeutically effective amount of at least one compound selected from compounds of Formula (IIa and IIb):

R3, R4 and R6 are independently H or C1-C3 alkyl;
R8 is phenyl or pyridyl, optionally substituted with zero to three Rm substituents wherein Rm is independently selected from the group consisting of: halo, C1-C3alkyl and perhaloalkyl;
R7 is (a) phenyl, optionally substituted with zero to two groups independently selected from the group consisting of halo and C1-C3alkyl, or
(b) heteroaryl, independently selected from the group consisting of:

wherein Rk is halo or C1-C3alkyl;
Rj is H or C1-C3alkyl; wherein C1-C3alkyl is optionally substituted with one halo substituent or one alkoxy substituent; and
n is an integer from 0-3; and
pharmaceutically acceptable salts of compounds of Formula (IIa and IIb); and
(b) at least one pharmaceutically acceptable excipient.

US Pat. No. 10,112,936

FIVE-MEMBERED HETEROCYCLES USEFUL AS SERINE PROTEASE INHIBITORS

Bristol-Myers Squibb Comp...

1. A compound of Formula (V)
or its stereoisomers, tautomers, a pharmaceutically acceptable salts, or solvates thereof, wherein:
A is C3-7 cycloalkyl substituted with 0-1 R1 and 0-2 R2;

Z is —CH(R11)—;
L is —C(O)NH—;
R1 is, independently at each occurrence, —NH2, —NH(C1-3 alkyl), —N(C1-3 alkyl)2, —C(?NH)NH2, —C(O)NR8R9, —S(O)pNR8R9, —(CH2)rNR7R8, —(CH2)rNR7C(O)ORa, —CH2N H2, —CH2NH(C1-3 alkyl), —CH2N(C1-3 alkyl)2, —CH2CH2NH2, —CH2CH2NH(C1-3 alkyl), —CH2CH2N(C1-3 alkyl)2, —CH(C1-4 alkyl)NH2, —C(C1-4 alkyl)2NH2, —C(?NR8a)NR7R8, —NHC(?NR8a)NR7R8, ?NR8, —NR8CR8(?NR8a), F, Cl, Br, I, OCF3, CF3, —(CH2)rORa, —(CH2)rSRa, CN, 1-NH2-1-cyclopropyl, or C1-6 alkyl substituted with 0-1 R1a;
R1a is H, —C(?NR8a)NR7R8, —NHC(?NR8a)NR7R8, —NR8CH(?NR8a), —NR7R8, —C(O)NR8R9, F, OCF3, CF3, ORa, SRa, CN, —NR9SO2NR8R9, —NR8SO2Rc, —S(O)p—C1-4 alkyl, —S(O)p-phenyl, or —(CF2)rCF3;
R2 is, independently at each occurrence, H, ?O, F, Cl, Br, I, OCF3, CF3, CHF2, CN, NO2, ORa, SRa, —C(O)Ra, —C(O)ORa, —OC(O)Ra, —NR7R8, —C(O)NR7R8, —NR7C(O)Rb, —S(O)2NR8R9, —NR8S(O)2Rc, —S(O)2Rc, —S(O)2Rc, C1-6 alkyl substituted with 0-2 R2a, C2-6 alkenyl substituted with 0-2 R2a, C2-6 alkynyl substituted with 0-2 R2a, —(CH2)r-C3-10 carbocycle substituted with 0-3 R2b, or —(CH2)r-5- to 10-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-3 R2b;
R2a is, independently at each occurrence, H, F, Cl, Br, I, ?O, ?NR8, CN, OCF3, CF3, ORa, SRa, —NR7R8, —C(O)NR8R9, —NR7C(O)Rb, —S(O)pNR8R9, —NR8SO2Rc, —S(O)Rc, or —S(O)2Rc;
R2b is, independently at each occurrence, H, F, C1, Br, I, ?O, ?NR8, CN, NO2, ORa, SRa, —C(O)Ra, —C(O)ORa, —OC(O)Ra, —NR7R8, —C(O)NR7R8, —NR7C(O)Rb, —S(O)2NR8R9, —S(O)2R C, —NR8SO2NR8R9, NR8SO2Rc, —(CF2)rCF3, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C1-4 haloalkyl, or C1-4 haloalkoxy;
alternately, when R1 and R2 groups are substituted on adjacent ring atoms, they can be taken together with the ring atoms to which they are attached to form a 5- to 7-membered carbocycle or heterocycle comprising: carbon atoms and 0-4 heteroatoms selected from N, O, and S(O)p, wherein said carbocycle or heterocycle is substituted with 0-2 R2b;
R3 is, independently at each occurrence, —(CH2)r-phenyl substituted with 0-3 R3a and 0-1 R3d, —(CH2)r-naphthyl substituted with 0-3 R3a and 0-1 R3d, —(CH2)r-indanyl substituted with 0-3 R3a and 0-1 R3d or —(CH2)r-5-10 membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, and substituted with 0-3 R3a and 0-1 R3d;
R3a is, independently at each occurrence, ?O, F, Cl, Br, I, OCF3, CF3, NO2, CN, —(CH2)rOR3b, —(CH2)rSR3b, —(CH2)rNR7R8, C(?NR8a)NR8R9, —NHC(?NR8a)NR7R8, —NR8CR8(?NR8a), —(CH2)rNR8C(O)R3b, ?NR8, —(CH2)rNR8C(O)R3b, —(CH2)rNR8C(O)2R3b, —(CH2)rS(O)pNR8R9, —(CH2)rNR8S(O)pR3c, —S(O)pR3c, —S(O)pR3c, —C(O)—C1-4 alkyl, —(CH2)rCO2R3 b, —(CH2)rC(O)NR8R9, —(CH2)rOC(O)NR8R9, —NHCOCF3, —NHSO2CF3, —SO2 NHR3b, —SO2NHCOR3c, —SO2NHCO2R3c, —CONHSO2R3c, —NHSO2R3c, —CONHOR3b, C1-4 haloalkyl, C1-4 haloalkoxy-, C1-6 alkyl substituted by R3d, C2-6 alkenyl substituted by R3d, C2-6 alkynyl substituted by R3d, C3-6 cycloalkyl substituted by 0-1 R3d, —(CH2)r—C3-10 carbocycle substituted with 0-3 R3d, or —(CH2)r-5- to 10-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-3 R3d;
alternately, when two R3a groups are located on adjacent atoms, they can be taken together with the atoms to which they are attached to form a C3-10 carbocycle substituted with 0-2 R3d or a 5- to 10-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-2 R3d;
R3b is, independently at each occurrence, H, C1-6 alkyl substituted with 0-2 R3d, C2-6alkenyl substituted with 0-2 R3d, C2-6 alkynyl substituted with 0-2 R3d, —(CH2)r—C3-10 carbocycle substituted with 0-3 R3d, or —(CH2)r-5- to 10-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-3 R3d;
R3c is, independently at each occurrence, C1-6 alkyl substituted with 0-2 R3d, C2-6 alkenyl substituted with 0-2 R3d, C2-6 alkynyl substituted with 0-2 R3d, —(CH2)r—C3-10 carbocycle substituted with 0-3 R3d, or —(CH2)r-5- to 10-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-3 R3d;
R3d is, independently at each occurrence, H, ?O, —(CH2)rORa, F, Cl, Br, CN, NO2, —(CH2)rNR7R8, —C(O)Ra, —C(O)ORa, —OC(O)Ra, —NR7C(O)Rb, —C(O)NR8R9, —SO2NR8R9, —NR8SO2NR8R9, —NR8SO2Rc, —S(O)pRc, —(CF2)rCF3, C1-6 alkyl substituted with 0-2 Re, C2-6 alkenyl substituted with 0-2 Re, C2-6 alkynyl substituted with 0-2 Re, —(CH2)r—C3-10 carbocycle substituted with 0-3 Rd, or —(CH2)r-5- to 10-membered heterocycle comprising carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-3 Rd;
R4 is H;
R7 is, independently at each occurrence, H, C1-6 alkyl, —(CH2)n-C3-10 carbocycle, —(CH2)n-(5-10 membered heteroaryl), —C(O)Rc, —CHO, —C(O)2Rc, —S(O)2Rc, —CONR8Rc, —OCONHRc, —C(O)O—(C1-4 alkyl)OC(O)—(C1-4 alkyl), or —C(O)O—(C1-4 alkyl)OC(O)—(C6-10 aryl); wherein said alkyl, carbocycle, heteroaryl, and aryl are optionally substituted with 0-2 Rf;
R8 is, independently at each occurrence, H, C1-6 alkyl, or —(CH2)r-phenyl, or —(CH2)n-5-10 membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p; wherein said alkyl, phenyl and heterocycle are optionally substituted with 0-2 Rf;
alternatively, R7 and R8, when attached to the same nitrogen, combine to form a 5- to 10-membered heterocyclic ring comprising carbon atoms and 0-2 additional heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-2 Rd;
R8a is, independently at each occurrence, H, OH, C1-6 alkyl, C1-4 alkoxy, (C6-10 aryl)-C1-4 alkoxy, —(CH2)n-phenyl, —(CH2)n-(5-10 membered heteroaryl), —C(O)Rc, —C(O)2Rc, —C(O)O—(C1-4 alkyl)OC(O)—(C1-4 alkyl), or —C(O)O—(C1-4 alkyl)OC(O)—(C6-10 aryl); wherein said phenyl, aryl, and heteroaryl is optionally substituted with 0-2 Rf;
R9 is, independently at each occurrence, H, C1-6 alkyl, or —(CH2)n-phenyl; wherein said alkyl and phenyl are optionally substituted with 0-2 Rf;
R9a is, independently at each occurrence, H, C1-6 alkyl, or —(CH2)n-phenyl;
alternatively, R8 and R9, when attached to the same nitrogen, combine to form a 5- to 10-membered heterocyclic ring comprising carbon atoms and 0-2 additional heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-2 Rd;
R11 is —CH2-phenyl;
Ra is, independently at each occurrence, H, CF3, C1-6 alkyl, —(CH2)r—C3-7 cycloalkyl, —(CH2)r—C6-10 aryl, or —(CH2)r-5- to 10-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p; wherein said cycloalkyl, aryl and heteroaryl groups are optionally substituted with 0-2 Rf;
Rb is, independently at each occurrence, CF3, OH, C1-4 alkoxy, C1-6 alkyl, —(CH2)r—C3-10 carbocycle substituted with 0-3 Rd, or —(CH2)r-5-10 membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, O, and S(O)p, wherein said heterocycle is substituted with 0-3 Rd;
Rc is, independently at each occurrence, CF3, C1-6 alkyl substituted with 0-2 Rf, C3-6 cycloalkyl substituted with 0-2 Rf, C6-10 aryl, 5- to 10-membered heteroaryl, (C6-10 aryl)-C1-4 alkyl, or (5- to 10-membered heteroaryl)-C1-4 alkyl, wherein said aryl and heteroaryl groups are optionally substituted with 0-3 Rf;
Rd is, independently at each occurrence, H, ?O, ?NR8, ORa, F, Cl, Br, I, CN, NO2, —NR7R8, —C(O)Ra, —C(O)ORa, —OC(O)Ra, —NR8C(O)Ra, —C(O)NR7R8, —SO2NR8SR9, —NR8SO2 NR8R9, —NR8SO2—C1-4 alkyl, —NR8SO2CF3, —NR8SO2-phenyl, —S(O)2CF3, —S(O)p—C1-4 alkyl, —S(O)p-phenyl, —(CF2)rCF3, C1-6 alkyl substituted with 0-2 Re, C2-6 alkenyl substituted with 0-2 Re, or C2-6 alkynyl substituted with 0-2 Re;
Re is, independently at each occurrence, ?O, ORa, F, Cl, Br, I, CN, NO2, —NR8R9, —C(O)Ra, —C(O)ORa, —OC(O)Ra, —NR8C(O)Ra, —C(O)NR7R8, —SO2NR8R9, NR8SO2NR8R9, —NR8SO2—C1-4 alkyl, —NR8SO2CF3, —NR8SO2-phenyl, —S(O)2CF3, —S(O)p—C1-4 alkyl, —S(O)p-phenyl, or —(CF2)rCF3;
Rf is, independently at each occurrence, H, ?O, —(CH2)r—OR, F, Cl, Br, I, CN, NO2, —NR9aR9a, —C(O)R9, —C(O)ORg, —NR9aC(O)R9, —C(O)NR9aR9a, —SO2NR9aR9a, —NR9aSO2NR9aR9a, —NR9aSO2—C1-4 alkyl, —NR9aSO2CF3, —NR9aSO2-phenyl, —S(O)2CF3, —S(O)p—C1-4 alkyl, —S(O)p-phenyl, —(CF2)rCF3, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, or —(CH2)n-phenyl;
Rg is, independently at each occurrence, H, C1-6 alkyl, or —(CH2)n-phenyl;
n, at each occurrence, is selected from 0, 1, 2, 3, and 4;
p, at each occurrence, is selected from 0, 1, and 2; and
r, at each occurrence, is selected from 0, 1, 2, 3, and 4.

US Pat. No. 10,112,935

INDAZOLYL THIADIAZOLAMINES AND RELATED COMPOUNDS FOR INHIBITION OF RHO-ASSOCIATED PROTEIN KINASE AND THE TREATMENT OF DISEASE

Lycera Corporation, Ann ...

1. A compound represented by Formula I:
or a pharmaceutically acceptable salt thereof, or a solvate of the foregoing; wherein:
R1 and R4 each represent independently for each occurrence hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C2-C4 alkenyl, or cyano;
R2 and R3 each represent independently for each occurrence hydrogen, C1-C3 alkyl, cyclopropyl, or cyano;
R5 is hydrogen, C1-C6 alkyl, C1-C6 hydroxyalkyl, or —CO2R12;
R6 and R7 each represent independently for each occurrence hydrogen, C1-C6 alkyl, C1-C6 hydroxyalkyl, or C3-C6 cycloalkyl; or R6 and R7 when attached to the same nitrogen atom may be taken together with the nitrogen atom to form a 3-7 membered ring optionally substituted with 1 or 2 R12;
R8 and R9 each represent independently for each occurrence hydrogen, C1-C6 alkyl, C1-C6 hydroxyalkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, —(C1-C6 alkylene)-O—(C1-C6 alkyl), or —(C1-C6 alkylene)-N(R6)(R7); or R8 and R9 when attached to the same nitrogen atom may be taken together with the nitrogen atom to form a 3-7 membered ring optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C3-C6 cycloalkyl, C1-C6 alkoxyl, cyano, hydroxyl, —CO2R6, —C(O)N(R6)(R7), —N(R6)C(O)R6, —N(R6)2, and —(C1-C6 alkylene)-CO2R6;
R10 represents independently for each occurrence C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 hydroxyalkyl, —(C1-C6 alkylene)-O—(C1-C6 alkyl), —(C1-C6 alkylene)-N(R8)(R9), —(C1-C6 alkylene)-CO2R6, —(C1-C6 alkylene)-(3-7 membered heterocycloalkyl), or 3-7 membered heterocycloalkyl; wherein said cycloalkyl is optionally substituted by 1 or 2 C1-C6 alkyl;
R11 represents independently for each occurrence a 5-6 membered heteroaryl or 3-7 membered heterocycloalkyl, each of which is optionally substituted with 1 or 2 occurrences of Y1;
R12 represents independently for each occurrence C1-C6 alkyl or C3-C6 cycloalkyl;
A1 is a cyclic group selected from:
or dihydropyridinyl, each being optionally substituted by X1 and 0, 1, 2, or 3 occurrences of Y1;(iii) a heteroaryl selected from the group consisting a 8-10 membered bicyclic heteroaryl, a 5-membered heteroaryl, and a 6-membered heteroaryl containing at least two ring nitrogen atoms; wherein said heteroaryl is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of X1, Y1, —(C1-C6 alkylene)-CO2R8, —N(R6)(R7), —O-(3-7 membered heterocyclyl), a 3-7 membered heterocycloalkyl, and C6 aryl;
(iv) a 3-7 membered heterocycloalkyl, C3-C7 cycloalkyl, or 8-10 membered bicyclic partially unsaturated heterocyclyl, each optionally substituted by oxo, C6 aryl, X1, and 0, 1, 2, or 3 occurrences of Y1; or
(v) aralkyl or heteroaralkyl, each being optionally substituted by a C6 aryl, X1, and 0, 1, 2, or 3 occurrences of Y1;
X1 represents independently for each occurrence:
—N(R6)C(O)-(3-7 membered heterocyclyl), —N(R6)C(O)-phenyl, —N(R6)C(O)-aralkyl, or —N(R6)C(O)-heteroaralkyl; each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of Y1 and —N(R8)(R9);
—CO2R8, —C(O)N(R8)(R9), —C(O)R11, —C(O)R12, —C(O)-(3-7 membered heterocyclyl), —C(O)N(R8)(R10), —N(R6)C(O)R10, —N(R10)C(O)R10, —N(R6)CO2R10, —N(R8)SO2R10, —N(R6)—(C1-C6 alkylene)-C(O)N(R8)(R9), —N(R6)—C(O)—(C1-C6 hydroxyalkylene)-N(R8)(R9), —N(R6)—C(O)-(2-6 membered heteroalkyl), —N(R6)C(O)N(R6)(R7), or —NO2;
—O—(C1-C6 alkylene)-CO2R8, —OC(O)R12, —O—(C1-C6 alkylene)-C(O)N(R8)(R9), —O—(C1-C6 alkylene)-N(R8)(R9), —O—(C1-C6 alkyl), —O-(3-7 membered heterocyclyl), —O—(C1-C6 alkylene)-aryl, or —O—(C1-C6 alkylene)-heteroaryl;
—SO2R10, —SO2N(R8)-heteroaryl, cyano, or —P(O)(OR8)2;
5-6 membered heteroaryl, 3-7 membered heterocycloalkyl, 3-7 membered oxo-heterocycloalkyl, or 8-10 membered bicyclic heterocyclyl, each of which is optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of phenyl, and —N(R6)(R7); or
—(C2-C6 alkylene)-aryl, —(C2-C6 alkylene)-heterocyclyl, or —(C1-C6 alkylene)-COR12;
Y1 represents independently for each occurrence halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C3-C6 cycloalkyl, C1-C6 alkoxyl, C2-C6 alkenyl, cyano, hydroxyl, —CO2R8, —C(O)N(R8)(R9), —N(R6)C(O)R10, —N(R6)C(O)N(R6)(R7), —(C1-C6 alkylene)-CO2R8, —(C1-C6 alkylene)-O—(C1-C6 alkyl), —(C1-C6 alkylene)-N(R6)(R7), —(C1-C6 alkylene)-N(R6)S(O)2R12, —(C1-C6 alkylene)-S—C(O)R12, —S—R12, or 3-7 membered heterocycloalkyl; and
m is 0, 1, 2, or 3.

US Pat. No. 10,112,932

BENZOXAZEPIN OXAZOLIDINONE COMPOUNDS AND METHODS OF USE

Genentech, Inc., South S...

1. A process for the preparation of compound 8, having the structure:
or a stereoisomer, geometric isomer, tautomer, or pharmaceutically acceptable salt thereof, wherein:
R1 is selected from the group consisting of —CH3, —CH2CH3, cyclopropyl, and cyclobutyl;
R2 is selected from the group consisting of —CH3, —CHF2, —CH2F, and —CF3;
comprising reacting compound 7, having the structure:

with an amino acid of formula H2NCH(R1)CO2H and a copper catalyst, followed by ammonium chloride, and HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate) to form 8.

US Pat. No. 10,112,931

3-PYRIMIDIN-4-YL-OXAZOLIDIN-2-ONES AS INHIBITORS OF MUTANT IDH

NOVARTIS AG, Basel (CH)

1. A compound according to formula (V)
wherein:
R2a is methyl or C1-3 haloalkyl;
R5 and R6 are each independently hydrogen, deuterium, halo, —C(O)OCH3, C1-3 alkyl or C1-3 haloalkyl;
R7 is

wherein:
ring A is a 6 membered heteroaryl ring having one to three nitrogen atoms;
ring B is a 5 membered heteroaryl ring having one to four heteroatoms each independently selected from the group consisting of N, O and S;
each R8 is independently hydrogen, halo, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy or C1-3 haloalkoxy;
n is 1 or 2;
R9 is hydrogen, halo, C1-3 haloalkyl, optionally substituted C1-6 alkyl, optionally substituted C3-6 cycloalkyl, optionally substituted aryl, optionally substituted 5 or 6 membered heterocyclic, optionally substituted heteroaryl, —OR9a, —SO2R9a, C(O)NHR9a, CH2R9b or CHCH3R9b, wherein:
said C1-6 alkyl is optionally substituted with one to three substituents each independently selected from the group consisting of: OH, phenyl and phenoxy, and
said C3-6 cycloalkyl, 5 or 6 membered heterocyclic, aryl and heteroaryl are each optionally substituted with one to three substituents each independently selected from the group consisting of: halo, hydroxyl, cyano, NRR, C1-6 alkyl, C1-6 haloalkyl, C1-3 alkoxy, and C1-3 haloalkoxy;
R9a is optionally substituted C1-6 alkyl, C1-6 haloalkyl, optionally substituted C3-6 cycloalkyl, optionally substituted phenyl, or optionally substituted heterocyclic,
wherein:
said C1-6 alkyl is optionally substituted with one C3-6 cycloalkyl,
said C3-6 cycloalkyl and heterocyclic are each optionally substituted with one to three substituents each independently selected from the group consisting of: hydroxyl, CH2OH, —NRR, cyano, C1-3 alkyl, C1-3 haloalkyl, and C1-3 alkoxy, and
said phenyl is optionally substituted with one to three substituents each independently selected from the group consisting of: halo, hydroxyl, cyano, NRR, C1-6 alkyl, C1-6 haloalkyl, C1-3 alkoxy, and C1-3 haloalkoxy;
R9b is optionally substituted C3-6 cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclic,
said C3-6 cycloalkyl and heterocyclic are each optionally substituted with one to four substituents each independently selected from the group consisting of: hydroxyl, CH2OH, —NRR, —NRC(O)CH3, 4 to 6 membered heterocyclic, cyano, halo, C1-3 alkyl, C1-3 haloalkyl, and C1-3 alkoxy, and said phenyl is optionally substituted with one to three substituents each independently selected from the group consisting of: halo, hydroxyl, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-3 alkoxy, and C1-3 haloalkoxy; and
each R is independently selected from the group consisting of H, C1-3 alkyl and C3-6 cycloalkyl; or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,112,930

COMPOSITIONS AND METHODS FOR CONTROLLING NEMATODES

Monsanto Technology LLC, ...

1. A method for control of plant parasitic nematodes, the method comprising administering to a plant, a seed or soil a composition comprising an effective amount of a compound of Formula III or a salt thereof,
wherein,
A is phenyl or pyrazyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halogen, CF3, CH3, OCF3, OCH3, CN and C(H)O; and
C is thienyl, furanyl, oxazolyl, or isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of fluorine, chlorine, CH3 and OCF3.

US Pat. No. 10,112,929

LACTAMS AS INHIBITORS OF ROCK

Bristol-Myers Squibb Comp...

1. A compound according to Formula (I):
or an enantiomer, a diastereomer, a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof, wherein
Ring A is independently selected from

J1, J2, J3, and J4 are independently selected from N, CR3 and CR4; provided no more than two of J1, J2, J3, and J4 are N;
K is independently selected from the group consisting of N, CR1 and CR2;
L is NR6(CR7R7)m;
R1 is independently selected from the group consisting of H, F, Cl, Br, OH, CN, NRaRa, —OC1-4 alkyl substituted with 0-3 Re, and C1-4 alkyl substituted with 0-3 Re;
R2 is independently selected from the group consisting of H, F, Cl, Br, —(CH2)rORb, (CH2)rS(O)pRc, —(CH2)rC(?O)Rb, —(CH2)rNRaRa, —(CH2)rCN, —(CH2)rC(?O)NRaRa, —(CH2)rNRaC(?O)Rb, —(CH2)rNRaC(?O)NRaRa, —(CH2)NRaC(?O)ORb, —(CH2)rOC(?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;
R3 is independently selected from the group consisting of H, F, Cl, Br, CN, C1-4 alkyl substituted with 0-3 Re, —(CH2)rORb, (CH2)rS(O)pRc, —(CH2)rC(?O)Rb, —(CH2)rNRaRa, —(CH2)rC(?O)NRaRa, —(CH2)rC(?O)(CH2)rNRaRa, —(CH2)rCN, —(CH2)rNRaC(?O)Rb, —(CH2)rNRaC(?O)ORb, —(CH2)rOC(?O)NRaRa, —(CH2)rNRaC(?O)NRaRa, —(CH2)k(?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;
R4 is independently selected from the group consisting of H, F, Cl, Br, OH, CN, OC1-4 alkyl substituted with 0-3 Re, NRaRa, and C1-4 alkyl substituted with 0-3 Re;
R5 is independently selected from the group consisting of H, ?O, C1-4alkyl substituted with 0-4 Re, —(CH2)rORb, (CH2)rS(O)pRc, —(CH2)rC(?O)Rb, —(CH2)rNRaRa, —(CH2)rCN, —(CH2)rC(?O)NRaRa, —(CH2)rNRaC(?O)Rb, —(CH2)rNRaC(?O)NRaRa, —(CH2)rNRaC(?O)ORb, —(CH2)rOC(?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;
R6 is independently selected from the group consisting of H and C1-4alkyl substituted with 0-4 Re;
R7 is 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)NRaRa, —(CH2)rC(?O)(CH2)rNRaRa, —(CH2)rNRaC(?O)Rb, —(CH2)rNRaC(?O)ORb, —(CH2)rOC(?O)NRaRa, —(CH2)rNRaC(?O)NRaRa, —(CH2)k(?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; alternatively, R7 and R7 form ?O;
R8 is independently selected from the group consisting of C3-6 cycloalkyl, heterocyclyl, aryl and heteroaryl, each substituted with 0-5 R9;
alternatively, when m is zero, R8 and R6 together with the nitrogen atom to which they are both attached form a heterocyclic ring substituted with 0-5 R9;
R9 is independently selected from the group consisting of H, ?O, F, Cl, Br, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, nitro, —(CRdRd)rS(O)pRc, —(CRdRd)rS(O)pNRaRa, —(CRdRd)rNRaS(O)pRc, —(CRdRd)rORb, —(CRdRd)rCN, —(CRdRd)rNRaRa, —(CRdRd)rNRaC(?O)Rb, —(CRdRd)rNRaC(?O)NRaRa, —(CRdRd)rNRaC(?O)ORb, —(CRdRd)rC(?O)ORb, —(CRdRd)rC(?O)NRaRa, —(CRdRd)rC(?O)Rb, —(CRdRd)rOC(?O)Rb, —(CRdRd)rOC(?O)NRaRa, —(CRdRd)r-cycloalkyl, —(CRdRd)r-heterocyclyl, —(CRdRd)r-aryl, and —(CRdRd)r-heteroaryl, wherein said alkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is substituted with 0-4 Re;
Ra, at each occurrence, is independently selected from the group consisting of 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; 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 the group consisting of 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 the group consisting of 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 the group consisting of H and C1-4alkyl substituted with 0-5 Re;
Re, at each occurrence, is independently selected from the group consisting of C1-6 alkyl substituted with 0-5 Rf, C2-6 alkenyl, C2-6 alkynyl, —(CH2)r—C3-6 cycloalkyl, —(CH2)r—C4-6 heterocyclyl, —(CH2)r-aryl, —(CH2)r-heteroaryl, F, Cl, Br, CN, NO2, ?O, CO2H, —(CH2)rORf, S(O)pRf, C(?O)NRfRf, NRfC(?O)Rd, S(O)pNRfRf, NRfS(O)pRd, NRfC(?O)ORd, OC(?O)NRfRf and —(CH2)rNRfRf;
Rf, at each occurrence, is independently selected from the group consisting of H, F, Cl, Br, CN, OH, C1-5alkyl, C3-6 cycloalkyl, and phenyl; or Rf and Rf together with the nitrogen atom to which they are both attached form a heterocyclic ring optionally substituted with C1-4alkyl;
m is independently selected from zero, 1, and 2;
p, at each occurrence, is independently selected from zero, 1, and 2; and
r, at each occurrence, is independently selected from zero, 1, 2, 3, and 4.

US Pat. No. 10,112,928

INHIBITORS OF SYK

HOFFMANN-LA ROCHE INC., ...

1. A compound of Formula I
wherein:
R1 is —OR1? or (CH2)nR1?;
R1? is phenyl, pyridyl, cycloalkyl, amino cycloalkyl C1-6 alkyl or C1-6 alkyl, optionally substituted with one or more R1?;
each R1? is independently cyano, amino, amino C1-6 alkyl, halo, C1-6 alkyl, cycloalkyl, or amino cycloalkyl C1-6 alkyl;
R2 is C1-6 alkyl, cycloalkyl, cyano C1-6 alkyl, hydroxy C1-6 alkyl, halo C1-6 alkyl, dialkyl amino, or C1-6 alkoxy;
R3 is absent;
R4 is H or C1-6 alkyl;
X1 is CH or N;
X2 is CH, CR2 or N;
X3 is CH or N;
Y1 is N; and
Y2 is N;
Y3 is CH; and
n is 0 or 1;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,112,927

INHIBITORS OF CYCLIN-DEPENDENT KINASE 7 (CDK7)

Dana-Farber Cancer Instit...

1. A compound of Formula (I):or a pharmaceutically acceptable salt thereof;wherein:Ring A is

each instance of RA1 is independently selected from the group consisting of hydrogen and alkyl;
each instance of RA2 is independently selected from the group consisting of hydrogen, halogen, alkyl, aryl, and heteroaryl;
Ring B is of the formula:

RB1 is selected from the group consisting of hydrogen and alkyl,
WB is CRB2, wherein RB2 is selected from the group consisting of hydrogen, cyano, halogen, optionally substituted alkyl, carbocyclyl, and ORB2a,
wherein RB2a is selected from the group consisting of hydrogen and alkyl;
or RB1 and RB2 are joined to form a carbocyclyl or aryl ring;
X is NRX—, wherein RX is hydrogen or C1-6 alkyl;
L2 is —NRL2aC(?O)— or —NRL2aS(?O)2—, wherein RL2a is hydrogen or C1-6 alkyl;
each instance of RC is independently selected from the group consisting of hydrogen, halogen, and alkyl;
n is 0, 1, 2, 3, or 4;
each instance of RD is independently selected from the group consisting of hydrogen, halogen, alkyl, and —N(RD1)2,
wherein each occurrence of RD1 is independently selected from the group consisting of hydrogen and alkyl;
p is 0, 1, 2, 3, or 4;
RE is

RE and L2 are para or meta to each other;
L3 is —NRL3a— or an optionally substituted C1-4 hydrocarbon chain, wherein RL3a is hydrogen;
RE1 is selected from the group consisting of hydrogen and alkyl;
RE2 is hydrogen or alkyl;
RE3 is selected from the group consisting of hydrogen, alkyl, —CH2ORE3a, and —CH2N(RE3a)2,
wherein each occurrence of RE3a is independently selected from the group consisting of hydrogen, alkyl,

 and alkynyl; and
Y is O;
wherein “substituted” within each of RB2 and L3, refers independently to halogen, cyano, —NO2, —OH, —ORaa, —N(Rbb)2, —SH, —SRaa,—C(?O)Raa, —CO2H, —CHO, —CO2Raa, —OC(?O)Raa, —OCO2Raa, —C(?O)N(Rbb)2, —OC(?O)N(Rbb)2, —NRbbC(?O)Raa, —NRbbCO2Raa, —NRbbC(?O)N(Rbb)2, —C(?NRbb)Raa,—C(?NRbb)N(Rbb)2,—NRbbC(?NRbb)N(Rbb)2;
each of Raa is independently alkyl; and
each of Rbb is independently hydrogen or alkyl.

US Pat. No. 10,112,926

AMINO PYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL 3-KINASE INHIBITORS

Novartis AG, Basel (CH)

1. A compound of formula (I)
or a pharmaceutically acceptable salt thereof, wherein
E is selected from N and CRE;
R1, R2 and RE are independently selected from H, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, C1-4 hydroxyalkyl and C3-7 cycloalkyl;
R3 is selected from
(i) C1-4 alkyl which is unsubstituted or substituted with 1 or more substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 haloalkyl, C1-4 alkoxy, C1-4 alkyl, oxo, CN, —(C0-3 alkyl)-NR3aR3b, C3-7 cycloalkyl and C3-7 heterocyclyl, and wherein the C3-7 cycloalkyl or C3-7 heterocyclyl is unsubstituted or substituted with 1 to 3 substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, oxo and —(C0-3 alkyl)-NR3aR3b;
(ii) C1-4 alkoxy which is unsubstituted or substituted with 1 or more substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 haloalkyl, C1-4 alkoxy, C1-4 alkyl, oxo, CN, —(C0-3 alkyl)-NR3aR3b, C3-7 cycloalkyl and C3-7 heterocyclyl, and wherein the C3-7 cycloalkyl or C3-7 heterocyclyl is unsubstituted or substituted with 1 to 3 substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, oxo and —(C0-3 alkyl)-NR3aR3b;
(iii) —C3-7 cycloalkyl or —O—C3-7 cycloalkyl wherein the C3-7 cycloalkyl is unsubstituted or substituted with 1 to 3 substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, oxo and —(C0-3 alkyl)-NR3aR3b;
(iv) —(C0-3 alkyl)-C3-7 cycloalkyl or —O—(C0-3 alkyl)-C3-7 cycloalkyl wherein the C3-7 cycloalkyl is spiro fused to a second C3-7 cycloalkyl or C3-7 heterocyclyl by one single carbon atom, and wherein the C3-7 cycloalkyl or C3-7 heterocyclyl is unsubstituted or substituted with 1 to 3 substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, oxo and —(C0-3 alkyl)-NR3aR3b;
(v) —(C0-3 alkyl)-C3-7 heterocyclyl or —O—(C0-3 alkyl)-C3-7 heterocyclyl, and wherein said C3-7 heterocyclyl is unsubstituted or substituted with 1 to 3 substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, oxo and —(C0-3 alkyl)-NR3aR3b;
(vi) —(C0-3 alkyl)-C3-7 heterocyclyl or —O—(C0-3 alkyl)-C3-7 heterocyclyl, and wherein said C3-7 heterocyclyl is spiro fused to a second C3-7 heterocyclyl or a C3-7 cycloalkyl by one single carbon atom, and wherein the C3-7 heterocyclyl or C3-7 cycloalkyl is unsubstituted or substituted with 1 to 3 substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, oxo and —(C0-3 alkyl)-NR3aR3b;
(vii) pyridyl wherein the pyridyl is unsubstituted or substituted with 1 to 3 substituents independently selected from C1-4 alkyl, C1-4 alkoxy, hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 haloalkyl and —(C0-3 alkyl)-NR3aR3b; and
(viii) H;
R4 is selected from H and C1-4 alkyl; or
R3 and R4 together with the nitrogen atom to which they are attached form a C3-7 heterocyclyl, which C3-7 heterocyclyl is optionally spiro fused to a second C3-7 heterocyclyl or a C3-7 cycloalkyl by one single carbon atom, and which C3-7 heterocyclyl and C3-7 cycloalkyl are unsubstituted or substituted with 1 to 3 substituents independently selected from hydroxy, C1-4 hydroxyalkyl, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, oxo and —(C0-3 alkyl)-NR3aR3b;
R3a and R3b are independently selected from H, C1-4 alkyl and C1-4 haloalkyl;
Y is selected from the group consisting of
oxazol-5-yl,
thiazol-5-yl,
thiazol-4-yl,
isothiazol-5-yl,
pyrazol-4-yl,
pyrazol-1-yl,
pyrid-4-yl,
1,2,4-triazol-1-yl,
1,2,3-triazol-4-yl,
1,2,4-oxadiazol-5-yl,
1,3,4-oxadiazol-2-yl,
isoxazol-5-yl,
isoxazol-4-yl, and
pyrrol-3-yl,
each of which is unsubstituted or substituted with 1 to 3 substituents independently selected from C1-4 alkyl, C1-4 haloalkyl, —(C?O)—C3-7 heterocyclyl, —(C0-3 alkyl)-NR?R? and —(C?O)—NR?R?; and
R? and R? are independently selected from H and C1-4 alkyl;
or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,112,924

PIPERDINYL NOCICEPTIN RECEPTOR COMPOUNDS

Astraea Therapeutics, Inc...

1. A compound of structural formula (I):
or salts, hydrates or solvates thereof wherein:

B is hydrogen;
R1 and R2 together with the carbon atoms to which they are attached form aryl, substituted aryl, heteroaryl or substituted heteroaryl;
X is hydrogen, —CH?NOR4, —C(O)NR5R6, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl or substituted heteroarylalkyl;
Y is hydrogen, —CH?NOR7, —C(O)NR8R9, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl or substituted heteroarylalkyl;
R4 is hydrogen, alkyl or substituted alkyl;
R5 is hydrogen, alkyl or substituted alkyl;
R6 is hydrogen, alkyl, substituted alkyl or —OR15;
R7 is hydrogen, alkyl or substituted alkyl;
R8 and R9 are independently hydrogen, alkyl or substituted alkyl;
L is C4 cycloalkyl, C6 cycloalkyl, C7 cycloalkyl, C8 cycloalkyl, (C3-C8) substituted cycloalkyl, cyclohexyl substituted with

 (C3-C8 cycloheteroalkyl, C3 substituted cycloheteroalkyl, C5 substituted cycloheteroalkyl, C6 substituted cycloheteroalkyl, C7 substituted cycloheteroalkyl, C8 substituted cycloheteroalkyl,

US Pat. No. 10,112,922

INHIBITOR OF BRUTON'S TYROSINE KINASE

Centaurus BioPharma Co., ...

1. A compound represented by Formula (III), or a pharmaceutically acceptable salt, solvate, metabolite, polymorph, ester, tautomer or prodrug thereof,wherein:Y and R15 join to form a 5-membered heterocyclic ring;
G is selected from the group consisting of H,
wherein R7, R8 and R9 are each independently selected from the group consisting of H, halogen, —COOH, substituted or unsubstituted lower alkyl, and substituted or unsubstituted lower heteroalkyl;R6 is H; and
n is 0, 1, 2, 3 or 4.

US Pat. No. 10,112,921

METHOD FOR PREPARATION OF THIOPHENE-2-CARBONYL CHLORIDES WITH OXALYL CHLORIDE

LONZA LTD, Visp (CH)

1. A method for the preparation of compound of formula (III);
wherein the method comprises a step ST1;
ST1 comprises a reaction REAC1 of compound of formula (II) with oxalyl chloride;
REAC1 is done at a temperature TEMP1 of 160 to 250° C. for a time TIME1 of from 10 seconds to 24 hours; and
wherein the molar amount of oxalyl chloride is from 1.5 to 25 times based on the molar amount of compound of formula (II);

wherein R1 is H or Cl.

US Pat. No. 10,112,920

BETA- AND GAMMA-AMINO-ISOQUINOLINE AMIDE COMPOUNDS AND SUBSTITUTED BENZAMIDE COMPOUNDS

Aerie Pharmaceuticals, In...


or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,112,919

METHODS OF PREPARING OXA-BICYCLOALKENE

1. A method of preparing an oxa-bicycloalkene comprising reacting (i) a cycloalkanone and (ii) an allyl alcohol compound in the presence of an organic acid, a manganese catalyst, and oxygen at a temperature of 60 to 200° C. for 1 to 24 hours, wherein the oxa-bicycloalkene is 3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-cyclododeca[b]pyran having the following Formula (IV):
the cycloalkanone is cyclododecanone of Formula (V):
andthe allyl alcohol compound is allyl acetate or allyl alcohol.

US Pat. No. 10,112,918

15-OXOSPIRAMILACTONE DERIVATIVES, PREPARATION METHOD AND USES THEREOF

Kunming Institute of Bota...

1. A compound of Formula II, or a solvate or a pharmaceutically acceptable salt thereof,wherein,X1 is —CH2 or —CO;
R1 and R5 independently are —OH, or carbonyl oxygen;
R2 is selected from —H, carbonyl oxygen, ?CH2, —CH2OH, —CH2OCOCH3, —CH2OSO2CH3, halogen, —CH2NR7R8 and —CH2R1;
R7 and R8 may be the same or different, or may form a N-containing 5-membered or 6-membered ring together with the N which they are linked to;
R6 is ?CH2 linked to the C atom on the ring via the double bond represented by ;
R3 and R4 are independently selected from —OH, —COCH3, —COCH2CH3, —COCH2Cl, -Ms, —CH2CN, 2-thenoyl, and benzoyl; or
R3 and R4 are independently selected from hydroxyl, carbonyloxy, C1-6alkylacyl, benzoyl, C1-6 alkylsulfonyl, phenylsulfonyl, phenylmethylsulfonyl, and cinnamoyl; wherein
R3 and R4 may be optionally substituted with one or more substituents selected from halogen, C1-6 alkyl, C1-6 alkenyl, nitro, C1-6alkoxy, triazo, trifluoromethyl, furyl, and thienyl; or
R3 and R4 are independently selected from —CO(CH2)nCH3 and —CO(CH2)nCH2X; wherein n=1-8, and X is a halogen.

US Pat. No. 10,112,915

3-ARYL BICYCLIC [4,5,0] HYDROXAMIC ACIDS AS HDAC INHIBITORS

Forma Therapeutics, Inc.,...

1. A compound of Formula I:
or a pharmaceutically acceptable salt, hydrate, tautomer or isomer thereof,wherein:X1 is O;
X2 and X4 are each CR1R2;
X3 is CR1?R2?;
Y1 and Y4 are not bonded to —C(O)NHOH and are each CR1;
Y2 and Y3 are each CR1 when not bonded to —C(O)NHOH and Y2 and Y3 are C when bonded to —C(O)NHOH;
L is selected from the group consisting of a bond, —(CR1R2)n—, —C(O)O—, —C(O)NR3—, —S(O)2—, —S(O)2NR3—, —S(O)—, and —S(O)NR3—, wherein L is bound to the ring nitrogen through the carbonyl or sulfonyl group;
R is independently selected from the group consisting of —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C4-C8 cycloalkenyl, —C2-C6 alkynyl, —C3-C8 cycloalkyl, —C5-C12 spirocycle, heterocyclyl, spiroheterocyclyl, aryl, and heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O, wherein each alkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkyl, spirocycle, heterocyclyl, spiroheterocyclyl, aryl, or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of —OH, halogen, oxo, —NO2, —CN, —R1, —R2, —OR3, —NHR3, —NR3R4, —S(O)2NR3R4, —S(O)2R1, —C(O)R1, —CO2R1, —NR3S(O)2R1, —S(O)R1, —S(O)NR3R4, —NR3S(O)R1, heterocycle, aryl, and heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O;
each R1 and R2 are independently, and at each occurrence, selected from the group consisting of —H, —R3, —R4, —C1-C6 alkyl, —C2-C6 alkenyl, —C4-C8 cycloalkenyl, —C2-C6 alkynyl, —C3-C8 cycloalkyl, heterocyclyl, aryl, heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O, —OH, halogen, —NO2, —CN, —NHC1-C6 alkyl, —N(C1-C6 alkyl)2, —S(O)2N(C1-C6 alkyl)2, —N(C1-C6 alkyl)S(O)2R5, —S(O)2(C1-C6 alkyl), —(C1-C6 alkyl)S(O)2R5, —C(O)C1-C6 alkyl, —CO2C1-C6 alkyl, —N(C1-C6 alkyl)S(O)2C1-C6 alkyl, and —(CHR5)nNR3R4, wherein each alkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of —OH, halogen, —NO2, oxo, —CN, —R5, —OR3, —NHR3, NR3R4, —S(O)2N(R3)2, —S(O)2R5, —C(O)R5, —CO2R5, —NR3S(O)2R5, —S(O)R5, —S(O)NR3R4, —NR3S(O)R5, heterocycle, aryl, and heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O;
R1? and R2? are independently, and at each occurrence, selected from the group consisting of H, aryl, and heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O, wherein each aryl or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of —OH, halogen, —NO2, oxo, —CN, —R3, —R5, —OR3, —NHR3, —NR3R4, —S(O)2N(R3)2, —S(O)2R5, —C(O)R5, —CO2R5, —NR3S(O)2R5, —S(O)R5, —S(O)NR3R4, —NR3S(O)R5, heterocycle, aryl, and heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O, wherein at least one of R1? or R2? is not H;
R3 and R4 are independently, and at each occurrence, selected from the group consisting of —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C4-C8 cycloalkenyl, —C2-C6 alkynyl, —C3-C8 cycloalkyl, heterocyclyl, aryl, heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O, —S(O)2N(C1-C6 alkyl)2, —S(O)2(C1-C6 alkyl), —(C1-C6 alkyl)S(O)2R5, —C(O)C1-C6 alkyl, —CO2C1-C6 alkyl, and —(CHR5)nN(C1-C6 alkyl)2, wherein each alkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of —OH, halogen, —NO2, oxo, —CN, —R5, —O(C1-C6) alkyl, —NH(C1-C6) alkyl, —N(C1-C6 alkyl)2, —S(O)2N(C1-C6 alkyl)2, —S(O)2NHC1-C6 alkyl, —C(O)C1-C6 alkyl, —CO2C1-C6 alkyl, —N(C1-C6 alkyl)S(O)2C1-C6 alkyl, —S(O)R5, —S(O)N(C1-C6 alkyl)2, —N(C1-C6 alkyl)S(O)R5, heterocycle, aryl, and heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O;
or R3 and R can combine with the nitrogen atom to which they are attached to form a heterocycle or heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O, wherein each heterocycle or heteroaryl is optionally substituted with —R4, —OR4, or —NR4R5;
R5 is independently, and at each occurrence, selected from the group consisting of —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C4-C8 cycloalkenyl, —C2-C6 alkynyl, —C3-C8 cycloalkyl, heterocyclyl, aryl, heteroaryl containing 1 to 5 heteroatoms selected from the group consisting of N, S, P, and O, —OH, halogen, —NO2, —CN, —NHC1-C6 alkyl, —N(C1-C6 alkyl)2, —S(O)2NH(C1-C6 alkyl), —S(O)2N(C1-C6 alkyl)2, —S(O)2C1-C6 alkyl, —C(O)C1-C6 alkyl, —CO2C1-C6 alkyl, —N(C1-C6 alkyl)SO2C1-C6 alkyl, —S(O)(C1-C6 alkyl), —S(O)N(C1-C6 alkyl)2, —N(C1-C6 alkyl)S(O)(C1-C6 alkyl), and —(CH2)nN(C1-C6 alkyl)2; and
each n is independently and at each occurrence an integer from 0 to 6.

US Pat. No. 10,112,913

SUBSTITUTED [1,2,4]TRIAZOLE AND IMIDAZOLE COMPOUNDS AS FUNGICIDES

BASF SE, Ludwigshafen (D...

1. A compound of the formula I
wherein
A is CH or N;
R1 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl;
wherein the aliphatic moieties of R1 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy;
wherein the cycloalkyl moieties of R1 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R1b which independently of one another are selected from:
R1b halogen, OH, CN, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy;
R2 is hydrogen, C1-C4-alkyl, C2-C4-alkenyl or C2-C4-alkynyl;
wherein the aliphatic moieties of R2 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy;
R3 is selected from halogen, CN, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl and S(O)p(C1-C4-alkyl), wherein each of R3 is unsubstituted or further substituted by one, two, three or four R1a; wherein
R3a is independently selected from halogen, CN, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy;
p is 0, 1 or 2;
Z is CN, Si(C1-C4-alkyl)3, C1-C6-alkoxy or C(?O)—O—(C1-C6-alkyl);
wherein the aliphatic moieties of Z are not further substituted or carry one, two, three or four identical or different groups RZ, which independently of one another are selected from
RZ halogen, CN, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, O—C6H5, C1-C4-alkoxy and C1-C4-halogenalkoxy;
and the N-oxides and the agriculturally acceptable salts thereof.

US Pat. No. 10,112,912

HOMOPIPERAZINE-BASED CATALYSTS FOR NEUTRALIZATION OF ORGANOPHOSPHORUS-BASED COMPOUNDS

Lawrence Livermore Nation...

1. A composition of matter, comprising: a homopiperazine-based ligand; wherein the composition of matter has a structure selected from the group consisting of:
wherein each R is a chemical moiety independently selected from the group consisting of: hydrogen, an electron donating group, an electron withdrawing group, and a solubilizing ligand.

US Pat. No. 10,112,911

SUBSTITUTED CYANOGUANIDINES AS ORAL ANTI-VIRALS

ABBVIE INC., North Chica...

3. A pharmaceutical composition comprising the compound of claim 1, or a pharmaceutically acceptable salt thereof, and one or more excipients, and optionally one or more additional therapeutic agents.

US Pat. No. 10,112,908

METHODS FOR PRODUCING OPTICALLY ACTIVE VALERIC ACID DERIVATIVES

DAICHI SANKYO COMPANY, LI...

1. A method of producing a compound of formula (4):
comprising allowing a compound of formula (1):
to react with hydrogen gas, in an inert solvent, in the presence of a chiral ligand of formula (2) or (3):orand a ruthenium catalyst, or in the presence of an asymmetric transition metal complex catalyst previously generated from the chiral ligand and the ruthenium catalyst,wherein R is a protective group for the carboxy group or a hydrogen atom,
R1 and R2 are each independently a hydrogen atom or a protective group for the amino group,
Ar is a phenyl group, a 3,5-dimethylphenyl group or a 4-methylphenyl group, and
Ar? is a phenyl group, a 3,5-dimethylphenyl group or a 3,5-di-tert-butyl-4-methoxyphenyl group.

US Pat. No. 10,112,907

SUBSTITUTED INDAZOLES FOR TREATING TENDON AND/OR LIGAMENT INJURIES

NOVARTIS AG, Basel (CH)

10. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers.

US Pat. No. 10,112,905

MULTIFUNCTIONAL AMINOQUINOLINE THERAPEUTIC AGENTS

LOHOCLA RESEARCH CORPORAT...

1. A method of treating or preventing alcohol addiction relapse in a subject in need thereof, the method comprising administering to the subject a therapeutically effective amount of a compound or a pharmaceutically acceptable salt thereof; wherein the subject is abstinent from alcohol; and wherein the compound has the structure:
to treat or prevent the alcohol addiction relapse.

US Pat. No. 10,112,904

PROCESS FOR PREPARING SYNTHETIC INTERMEDIATES FOR PREPARING TETRAHYDROQUINOLINE DERIVATIVES

DEZIMA PHARMA B.V., Naar...

1. A process for preparing the racemic compound of formula I or a salt thereof:
comprising the steps of:(a) simultaneously reacting 4-aminobenzotrifluoride according to formula IIwith an aldehyde according to formula IIIand with a compound according to formula IV
in the presence of a solvent and optionally one or more catalysts to form the compound of formula V

whereinR1 is H or C1-C3 alkyl;R2 is H, C1-C3 alkyl or(b) hydrolyzing the compound of formula V to form the compound of formula (I); wherein prior to step (b) the compound of formula V is separated from the reaction mixture of step (a).

US Pat. No. 10,112,902

FUNGICIDAL PYRIDYLAMIDINES

Syngenta Participations A...

1. A compound of formula (I)
wherein
R1 and R2 independently represent hydrogen, C1-C4alkyl, C1-C4fluoroalkyl or C3-C6cycloalkyl; or
R1 and R2 together with the nitrogen atom to which they are attached form a three to six-membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom;
R3 represents fluorine, chlorine, bromine, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy or C3-C6 cycloalkyl;
R4 represents hydrogen, halogen, cyano, hydroxy, formyl, carboxy, amino, C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynl, C1-C6 haloalkyl, C1-C6 alkoxy or C3-C6 cycloalkyl;
R5 represents hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkynyl, C1-C4 alkoxy or C3-C6 cycloalkyl;
R6, R7, R8, R9 and R10 independently represent hydrogen or C1-C2 fluoroalkoxy;
wherein at least one of R6, R7, R8, R9 and R10 represent C1-C2 fluoroalkoxy;
or a tautomer, stereoisomer, enantiomer, salt or N-oxide thereof.

US Pat. No. 10,112,900

MODIFIED AMINO ACIDS

SUTRO BIOPHARMA, INC., S...

1. A compound according to formula I:
or a salt thereof, wherein:
D is Ar—W3— or —W1—Y1—C(O)—Y2—W2—;
Ar is

each of W1, W2, and W3 is independently a single bond or lower alkylene;
X1 is —O— or —S—;
Y1 is a single bond, —NH—, or —O—;
Y2 is an N-linked or C-linked divalent pyrrolidine radical; and
one of Z1, Z2, and Z3 is —N— and the others of Z1, Z2, and Z3 are independently —CH—.

US Pat. No. 10,112,899

ISOINDOLINE DERIVATIVES FOR USE IN THE TREATMENT OF A VIRAL INFECTION

ViiV HEALTHCARE UK LIMITE...

1. A compound of Formula I:or a pharmaceutically acceptable salt thereof, wherein:R1 is C1-6alkyl;
R2 is C5-14aryl, C3-7cycloalkyl, C3-7cycloalkenyl, C2-9heterocycle, or C2-9heteroaryl, wherein each R2 group is optionally substituted by one to four substituents selected from halo, C1-6alkyl, C1-6hetereoalkyl, or C1-6alkylene or C1-6hetereoalklylene wherein said C1-6alkylene or C1-6hetereoalklylene are bonded to adjacent carbon atoms on said C5-14aryl, C3-7cycloalkyl, C3-7cycloalkenyl, C3-9heterocycle, or C5-9heteroaryl to form a fused ring;
L is a bond, —CH2(CO)—, —C1-3alkylene-, —SO2?, —C(O)—, —C(S)—, —C(NH)—, —C(O)NH—, —C(O)NHCH2—, —C(O)OCH2—, —C(O)O—, —C(O)C(O)—, —SO2—NH—, or —CH2C(O)—;
R3 is H, CN, C1-6alkyl, C5-14aryl, CH2C5-14aryl, CH2C3-7cycloalkyl, C3-7cycloalkyl, C3-7spirocycloalkyl, C3-7cycloalkenyl, C2-9heterocycle, or C2-9heteroaryl, wherein each R3 group is optionally substituted by one to four substituents selected from halo, C1-6alkyl, C2-8bridgedheterocycle, C3-7cycloalkyl, C1-3fluoroalkyl, —OC1-6alkyl, —C(O)R4, —C(O)NR4, —C(O)NHR4, C5-14aryl, C1-6hetereoalkyl, —B(OH)2, C2-9heterocycle, C1-6heteroaryl, —C(O)OC1-6alkyl, or two substituents bonded to adjacent atoms may bond together to form a fused ring and that fused ring may optionally be substituted with R4;
R4 is CN, halo, —OC1-6alkyl, C1-6alkyl, C3-7cycloalkyl, C2-9heterocycle, or C5-14aryl;
and wherein each heterocycle, heteroaryl, heteroalkyl, and heteroalkylene comprises
one to three heteroatoms selected from S, N, B, or O.

US Pat. No. 10,112,898

PROCESS FOR THE PREPARATION OF SAROGLITAZAR PHARMACEUTICAL SALTS

Cadila Healthcare Limited...

1. A process for the preparation of a saroglitazar pharmaceutically acceptable salt of Formula (IB),
wherein M is a pharmaceutically acceptable cation,
the process comprising:
(a) reacting a hydroxy compound (A) with a mesylate compound (A1), in a mixture of cyclohexane and tetrahydrofuran in the presence of a base, to obtain alkoxy ester compound of Formula (II);

(b) hydrolyzing the alkoxy ester compound of Formula (II) using a base to obtain a compound of Formula (IB-1);

wherein M is a pharmaceutically acceptable cation selected from sodium, potassium, lithium, calcium, barium, strontium, and zinc;
(c) neutralizing the compound of Formula (IB-1) with an acid to obtain a compound of Formula (IB-2):

wherein M? is hydrogen; and
(d) converting the compound of Formula (IB-2) to a compound of Formula (IB).

US Pat. No. 10,112,897

SUBSTITUTED N-ACETYL-L-CYSTEINE DERIVATIVES AND RELATED COMPOUNDS

Promentis Pharmaceuticals...

2. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

US Pat. No. 10,112,895

ANTIVIRALS AGAINST MOLLUSCUM CONTAGIOSUM VIRUS

The Trustees of the Unive...

1. A compound of formula (X) or (XII):wherein:Y is heteroaryl; which is substituted with at least one group selected from the group consisting of phenyl and heteroaryl;
R1, R2, R3, R4, R5, R6, R7, R8, and R9 are independently selected from the group consisting of H, C1-C6 alkyl, halo, cyano, nitro, SO2NH2, C1-C6 haloalkyl, ORa, SRa, NRmRn, NRaCORb, SORb, SO2Rb, CORb, COORa, aryl, heteroaryl, C3-C7 cycloalkyl, 3-7 membered heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or two adjacent ORa or NRmRn groups, together with the atoms to which they are attached, form a 5-7 membered heterocycloalkyl group;
R14 is H, C1-C3 alkyl, C(O)ORa, C(O)Rb, C(O)NRmRn, SORb, or SO2Rb;
Ra and Rb are each independently selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl;
Rm and Rn are independently selected from the group consisting of H, C1-C6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or Rm and Rn, together with the nitrogen atom to which they are attached, form a 3-7 membered heterocycloalkyl group;
each occurrence of aryl is independently selected from the group consisting of phenyl and naphthyl; and
each occurrence of heteroaryl is independently selected from the group consisting of pyridine, pyrimidine, pyrazine, indole, indolizine, benzimidazole, 1,3-dihydrobenzimidazol-2-one, and indazole.

US Pat. No. 10,112,891

STEREOSELECTIVE PROCESS TO OBTAIN (Z)-5-CYCLYLOXY-2-[(E)-METHOXYIMINO]-3-METHYL-PENT-3-ENIC ACID METHYL AMIDES USING E,Z-ISOMER MIXTURE OF AND INTERMEDIATES THEREOF

BASF SE, Ludwigshafen (D...

1. A process for preparing compounds of formula I
wherein
R is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl;
Y is hydrogen, C1-C4-alkoxy, C2-C4-alkenyl or benzyl; and
wherein the —CH2—OH group and the —C(?NOCH3)C(?O)NYCH3 group are on the same side of the C?C double bond between the carbon atoms depicted with the numbers 3 and 4 (Z-configuration), and
wherein the —OCH3 group and the —C(?O)NYCH3 group are on the opposite side of the C?N double bond between the carbon atom depicted with number 2 and the neighbouring nitrogen atom (E-configuration);
the process comprising:
reacting a compound of formula II

wherein R is as defined above;
with a compound of formula III

wherein Y is as defined above.

US Pat. No. 10,112,890

COMPOUND, SALT OF COMPOUND, EXTERNAL AGENT FOR SKIN, COSMETIC, AND FOOD ADDITIVE

SHOWA DENKO K.K., Minato...

1. A compound of Formula (1) or a salt thereof,
(in the formula, R1 and R2 each independently is a hydrogen atom or a linear or branched acyl group having 11 to 18 carbon atoms, a hydrocarbon group bonded to a carbonyl carbon of the acyl group is a saturated or unsaturated hydrocarbon group, and at least one of R1 and R2 is the acyl group).

US Pat. No. 10,112,887

CATALYSTS BASED ON AMINO-SULFIDE LIGANDS FOR HYDROGENATION AND DEHYDROGENATION PROCESSES

1. A metal complex of Formula II and IIIM(SN)pZa  II
M(SNS)Za  IIIwherein:each Z is simultaneously or independently a hydrogen or halogen atom, a C1-C6 alkyl, a carbene group, a hydroxyl group, or a C1-C7 alkoxy radical, a nitrosyl (NO) group, CO, CNR (R=Alkyl, Aryl), nitrile, phosphite, phosphinite, or phosphine;
M is a group 7, group 8, or group 9 transition metal;
p is equal to 1 or 2, whereas a is equal to 1, 2, or 3;
SN is a bidentate coordinated ligand of Formula IA, wherein the coordinating groups of the SN ligand consist of one thio group and one nitrogen group;
SNS is a tridentate coordinated ligand of Formula IB, wherein the coordinating groups of the SNS ligand consist of two thio groups and one nitrogen group:
wherethe dotted lines simultaneously or independently indicate single or double bonds;
R1, R2, R5, and R6 are each independently H, a substituted or unsubstituted linear or branched C1-C20 alkyl, a substituted or unsubstituted cyclic C3-C8 alkyl, or a substituted or unsubstituted C2-C20 alkenyl, a substituted or unsubstituted C5-C20 aryl, OR or NR2; or when taken together, R1 and R2 groups or R5 and R6 groups can form a saturated or partially saturated C5-C20 cycle;
R3 and R4 are each independently H, a substituted or unsubstituted linear, branched or cyclic C1-C8 alkyl or alkenyl, a substituted or unsubstituted C5-C8 aromatic group, ester group; or, when taken together, R3 and R4 can form an optionally substituted saturated or partially saturated C5-C20 hetero-aromatic ring;
R5 when taken together with R4 can form an optionally substituted saturated or partially saturated C5-C20 aromatic ring;
R7 is H, a substituted or unsubstituted linear or branched C1-C8 alkyl, a substituted or unsubstituted cyclic C3-C8 alkyl, a substituted or unsubstituted C2-C20 alkenyl, or a substituted or unsubstituted C5-C20 aryl; and
n, m, and q are simultaneously or independently 0, 1, or 2.

US Pat. No. 10,112,886

METHOD FOR PURIFICATION OF BENZOIC ACID

Sulzer Chemtech AG, Wint...

1. A method for purifying a crude benzoic acid stream containing 5 to 20% by weight of byproducts and 80 to 95% by weight of benzoic acid, by means of distillation, the method comprising delivering the crude benzoic acid stream to a plant comprising a first distillation system, wherein the first distillation system comprises a divided wall column, thereby providing a purified benzoic acid stream.

US Pat. No. 10,112,884

ASYMMETRICAL HYDROGENATION REACTION OF KETONIC ACID COMPOUND

1. A preparation method of the structure of formula B,
Wherein R1 is a phenyl, a substituted phenyl, a naphthyl, a substituted naphthyl, a C1-C6 alkyl or aralkyl, the substitute is a C1-C6alkyl, a C1-C6 alkoxy, a halogen, the number of the substituents is 1-3
Wherein M is the following structure chiral spiro-pyridylamidophosphine ligand iridium complex:

Wherein R is hydrogen, 3-methyl, 4-tBu or 6-methyl,
The said base is selected from sodium hydroxide, potassium hydroxide, sodium tert-butyl oxide or potassium test-butyl oxide,
The molar dosage ratio of the said base to the substrate A compound is (1.0˜3):1.

US Pat. No. 10,112,882

USE OF NOVEL CYCLIC CARBALDEYDES AS AN AROMATIC SUBSTANCE

BASF SE, Ludwigshafen am...

1. A carbaldehyde of the formula X
wherein A is a cycloaliphatic, monocyclic unsubstituted hydrocarbon radical, the carbaldehyde selected from isomeric formulae I, II or III,
and the stereoisomeric forms thereof.

US Pat. No. 10,112,881

SKIN LIGHTENING COMPOUNDS

WISYS TECHNOLOGY FOUNDATI...

1. A method of inhibiting melanin synthesis and/or removing existing pigmentation from skin, said method comprising the step of administering an effective amount of a compound having the following formula:

US Pat. No. 10,112,880

PROCESSES FOR PRODUCING CHLORINATED HYDROCARBONS AND METHODS FOR RECOVERING POLYVALENT ANTIMONY CATALYSTS THEREFROM

EAGLE US 2 LLC, Houston,...

1. A method of preparing a chlorinated alkene product by chloroalkane dehydrochlorination process, the method comprising:(a) reacting at least one chlorinated alkane in the presence of at least one polyvalent antimony catalyst in a reaction vessel, thereby forming a crude product comprising at least one chlorinated alkene product, a portion of the at least one chlorinated alkane and the at least one polyvalent antimony catalyst, the at least one chlorinated alkene product having one less chloro group (or chlorine atom) covalently bonded thereto and one less hydrogen atom covalently bonded thereto than the at least one chlorinated alkane, the at least one chlorinated alkane and the at least one chlorinated alkene product having a carbon backbone structure that is in each case the same, the at least one chlorinated alkene product having a boiling point at least about 5° C. less than the at least one chlorinated alkane; and
(b) optionally converting the polyvalent antimony catalyst to trivalent antimony catalyst to form a product comprising at least one chlorinated alkene product, at least one chlorinated alkane, and at least one trivalent antimony catalyst;
(c) separating at least a portion of the at least one chlorinated alkene product from:
(i) the product of step (a) comprising at least one chlorinated alkene product, at least one chlorinated alkane, and at least one polyvalent antimony catalyst; or
(ii) the product of step (b) comprising the at least one chlorinated alkene product, at least one chlorinated alkane, and at least one trivalent antimony catalyst by distillation; and
(d) optionally, the trivalent antimony contained in the chlorinated alkane can be converted to pentavalent antimony by the addition of chlorinating agent such chlorine gas prior to its use as a catalyst in the chlorination of hydrocarbons and/or the cracking of halohydrocarbons.

US Pat. No. 10,112,877

PROCESS FOR OLEFIN PRODUCTION BY METATHESIS AND REACTOR SYSTEM THEREFOR

Borealis AG, Vienna (AT)...

1. A process for obtaining propene from at least two olefins as starting materials by metathesis, wherein one olefin is ethene and the other olefin is n-butene, comprising at least two reaction pathways, whereinin at least one first reaction pathway at least one stream comprising ethene and n-butene as starting material is fed to at least one first pre-bed reactor with at least one pre-bed comprising magnesium oxide effecting isomerisation of n-butene, and
the stream leaving the at least one first pre-bed reactor is subsequently fed to at least one main catalyst bed reactor downstream of the at least one first pre-bed reactor comprising at least one main catalyst bed comprising at least one first catalyst component comprising tungsten oxide supported on silica, and at least one second catalyst component comprising magnesium oxide, whereby the first and second catalyst are physically mixed with each other,
wherein
in at least one second reaction pathway the at least one stream comprising ethene and n-butene as starting material is re-directed from the at least one first pre-bed reactor to at least one second pre-bed reactor with at least one pre-bed comprising magnesium oxide effecting the isomerisation of the olefin, and
the stream leaving the at least one second pre-bed reactor is subsequently fed to the at least one main catalyst bed reactor downstream of the at least one second pre-bed reactor,
wherein an operational temperature of the first pre-bed reactor and an operational temperature of the second pre-bed reactor are in a range between 150° C. and 350° C. and are lower than an operational temperature of the main catalyst bed reactor, and
wherein the mass ratio of the pre-bed in the first pre-bed reactor and the second pre-bed reactor to the main catalyst bed in the main catalyst bed reactor is between 1:5 and 1:2.

US Pat. No. 10,112,876

PROCESS FOR OLIGOMERIZATION OF ETHYLENE

SAUDI BASIC INDUSTRIES CO...

1. A process for oligomerizing ethylene, comprising:a) oligomerizing ethylene in a reactor in the presence of a solvent and a catalyst;
b) transferring a reactor overhead effluent from the reactor to an externally located cooling device to condense a portion of the reactor overhead effluent and recycling the condensed portion of the reactor overhead effluent into the reactor;
c) recovering a reactor bottom effluent from the reactor, wherein the reactor bottom effluent comprises C4 hydrocarbons, C6 hydrocarbons, C8 hydrocarbons, C10 hydrocarbons, residual C12+ hydrocarbons, residual spent catalyst, and residual polymer material;
d) transferring the reactor bottom effluent to a quenching unit, wherein quench media is added to the reactor bottom effluent, to produce a quenched reactor bottom effluent;
e) transferring the quenched reactor bottom effluent to a series of fractionation columns and, in the following order,
i) optionally separating a fraction comprising the C4 hydrocarbons from the quenched reactor bottom effluent;
ii) separating a fraction comprising the C6 hydrocarbons from the quenched reactor bottom effluent;
iii) separating a fraction comprising both the C8 hydrocarbons and C10 hydrocarbons from the quenched reactor bottom effluent and recycling said fraction comprising both the C8 hydrocarbons and C10 hydrocarbons into the reactor, and
iv) separating the residual C12+ hydrocarbons, the residual spent catalyst, the residual polymer material, and residual quench media from the quenched reactor bottom effluent,
wherein the solvent is separated from the quenched reactor bottom effluent in any of steps i)-iv) and/or in an additional step.

US Pat. No. 10,112,875

METHOD FOR PROTECTING A HYBRID CERAMIC STRUCTURE FROM MOISTURE ATTACK IN A HIGH TEMPERATURE ENVIRONMENT

SIEMENS ENERGY, INC., Or...

1. A method for protecting a hybrid ceramic structure from moisture attack in a high temperature combustion environment containing moisture, the hybrid ceramic structure comprising a ceramic matrix composite substrate and a thermal insulation material disposed on the substrate, the method comprising:processing the hybrid ceramic structure to be in a bisque condition that provides a degree of porosity to the hybrid ceramic structure;
applying a vapor resistant material through surfaces of the thermal insulation material and the ceramic matrix composite substrate while the hybrid ceramic structure is in the bisque condition;
as a result of the degree of porosity provided by the bisque condition, infiltrating the vapor resistant material through interstices available within a thickness of the hybrid ceramic structure; and
sintering the hybrid ceramic structure to a fully sintered condition.

US Pat. No. 10,112,874

METHOD FOR COATING METAL NANOPARTICLES ON OXIDE CERAMIC POWDER SURFACE

Hohai University, Nanjin...

1. A method for coating metal nanoparticles on an oxide ceramic surface, comprising the following steps of:(1) blending oxide ceramic powder and a metal organic material according to a weight ratio of (1:1)-(10:1), obtaining blended powders through grinding and mixing the materials for 1-3 h, putting the grinded and blended powder into a rotational reactor, and starting up the rotational reactor to make the rotational reactor rotate, wherein the metal organic material is a stable organometallic compound formed by bonding an alkyl group or an alkyl of an aryl with a metal atom;
(2) bubbling mixed gas of oxygen and argon into the rotational reactor, keeping the temperature for 0.5-2 h after warming up to 400-500° C. at a rate of 5-10° C./min to oxidize the metal organic material into a metal oxide, and then closing a gas inlet valve for oxygen and argon; and
(3) bubbling reducing gas into the rotational reactor to reduce the metal oxide in step (2) into nanoparticles in a metallic state, cooling at a rate of 5-10° C./min, closing a gas inlet valve for reducing gas after cooling the temperature to room temperature, stopping the rotation of the rotational reactor, opening the reactor, taking the powder out, sieving and collecting the powder.

US Pat. No. 10,112,872

COMPOSITION FOR FORMING MN AND NB CO-DOPED PZT-BASED PIEZOELECTRIC FILM

MITSUBISHI MATERIALS CORP...

1. A composition for forming a Mn and Nb co-doped PZT-based piezoelectric film used for forming a PZT-based piezoelectric film formed of Mn and Nb co-doped composite metal oxides, the composition comprising:PZT-based precursors containing metal atoms configuring the composite metal oxides;
acetylacetone as a stabilizer; and
a diol as a solvent,
wherein the PZT-based precursors are contained in the composition so that a metal atom ratio (Pb:Mn:Nb:Zr:Ti) in the composition satisfies (1.00 to 1.25):(0.002 to 0.056):(0.002 to 0.056):(0.40 to 0.60):(0.40 to 0.60),
a rate of Mn is from 0.20 to 0.80 when the total of metal atom rates of Mn and Nb is 1,
a rate of Zr is from 0.40 to 0.60 when the total of metal atom rates of Zr and Ti is 1, and
the total rate of Zr and Ti is from 0.9300 to 0.9902 when the total of metal atom rates of Mn, Nb, Zr, and Ti is 1,
the diol is propylene glycol or ethylene glycol,
an amount of acetylacetone contained in the composition is from 0.5 moles to 4 moles when the total amount of Mn, Nb, Zr, and Ti contained in the composition is 1 mole, and
a rate of the diol in 100 mass % of the composition is from 16 mass % to 56 mass %.

US Pat. No. 10,112,869

HIGH-ALUMINA REFRACTORY ALUMINOSILICATE POZZOLAN IN WELL CEMENTING

Halliburton Enegry Servic...

1. A method of cementing comprising:introducing a cement composition into a subterranean formation, wherein the cement composition comprises: a component selected from the group consisting of cement kiln dust, and any combination thereof; a high-alumina refractory aluminosilicate pozzolan; and water, wherein the high-alumina refractory aluminosilicate pozzolan comprises Mullite in an amount of about 30 weight % or greater, wherein the high-alumina refractory aluminosilicate pozzolan comprises Corundum in an amount of about 10 weight % or greater, and wherein high-alumina refractory aluminosilicate pozzolan is substantially devoid of amorphous material; and allowing the cement composition to set.

US Pat. No. 10,112,863

FLOAT GLASS AND METHOD OF MANUFACTURING THE SAME

SAMSUNG DISPLAY CO., LTD....

1. A float glass comprising:a core layer;
an upper ion exchange layer disposed on the core layer; and
a lower ion exchange layer disposed below the core layer,
wherein a density of the upper ion exchange layer is about 0.001 kilogram per cubic meter to about 0.01 kilogram per cubic meter greater than a density of the lower ion exchange layer, and
wherein a difference between a depth of layer of the upper ion exchange layer and a depth of layer of the lower ion exchange layer ranges from about 0.01 micrometer to about 1.0 micrometer.

US Pat. No. 10,112,862

APPARATUS AND METHOD OF MANUFACTURING COMPOSITE GLASS ARTICLES

CORNING INCORPORATED, Co...

1. A method comprising:supplying a conjoined molten glass stream to an overflow distributor, a cross-section of the conjoined molten glass stream comprising a first cross-sectional portion and a second cross-sectional portion, the first cross-sectional portion comprising a first glass composition, the second cross-sectional portion comprising a second glass composition different than the first glass composition;
flowing the first glass composition over a first transverse segment of a weir of the overflow distributor; and
flowing the second glass composition over a second transverse segment of the weir of the overflow distributor,
wherein at least one of the first transverse segment of the weir or the second transverse segment of the weir comprises less than an entire effective width of the weir.

US Pat. No. 10,112,861

METHOD OF MANUFACTURING A PLURALITY OF GLASS MEMBERS, A METHOD OF MANUFACTURING AN OPTICAL MEMBER, AND ARRAY OF GLASS MEMBERS IN A GLASS SUBSTRATE

Infineon Technologies AG,...

1. A method of manufacturing a plurality of glass members, the method comprising:bringing a first main surface of a glass substrate in contact with a first working surface of a first mold substrate, the first working surface being provided with a plurality of first protruding portions;
bringing a second main surface of the glass substrate in contact with a second working surface of a second mold substrate, the second working surface being provided with a plurality of second protruding portions;
controlling a temperature of the glass substrate to a temperature above a glass-transition temperature to form the plurality of glass members;
removing the first and the second mold substrates from the glass substrate; and
separating adjacent ones of the plurality of glass members,
wherein controlling the temperature of the glass substrate causes the glass substrate to conform to the first and second working surfaces of the first and second mold substrates, respectively, such that:
a plurality of depressions is formed in the first main surface of the glass substrate, each of the depressions extending towards the second main surface and disposed between thicker sections of the glass substrate; and
a plurality of kerfs is formed in the second main surface of the glass substrate, each of the kerfs extending towards the first main surface and disposed within the thicker sections of the glass substrate,
wherein a thickness of the thicker sections is locally minimized by each of the kerfs.

US Pat. No. 10,112,860

THERMOCHEMICAL REGENERATION WITH FUEL ADDITIONS

PRAXAIR TECHNOLOGY, INC.,...

1. A method of carrying out combustion in a furnace, comprising(A) combusting fuel in a furnace to produce gaseous combustion products which contain oxygen; and
(B) alternately
(1) (i) passing a portion of the gaseous combustion products out of the furnace into a first chamber, feeding hydrocarbon fuel into the first chamber, and reacting the hydrocarbon fuel in the first chamber with oxygen present in the gaseous combustion products to reduce the concentration of oxygen in the first chamber and to produce a gaseous reaction mixture containing oxygen and from zero up to 20,000 ppm of carbon monoxide;
(ii) passing the gaseous reaction mixture out of the first chamber into and through a cooled first regenerator to heat the first regenerator and cool said gaseous reaction mixture;
(iii) passing at least part of said cooled gaseous reaction mixture from said first regenerator, and fuel, into a heated second regenerator and, in the second regenerator, reacting the gaseous reaction mixture and the fuel in an endothermic reaction in the second regenerator to form syngas comprising hydrogen and CO; and
(iv) passing said syngas formed in the second regenerator into said furnace and combusting the syngas with one or more oxidant streams injected into said furnace; and
(2) (i) passing a portion of the gaseous combustion products out of the furnace into a second chamber, feeding hydrocarbon fuel into the second chamber, and reacting the hydrocarbon fuel in the second chamber with oxygen present in the gaseous combustion products to reduce the concentration of oxygen in the second chamber and to produce a gaseous reaction mixture containing oxygen and from zero up to 20,000 ppm of carbon monoxide;
(ii) passing the gaseous reaction mixture out of the second chamber into and through a cooled second regenerator to heat the second regenerator and cool said gaseous reaction mixture;
(iii) passing at least part of said cooled gaseous reaction mixture from said second regenerator, and fuel, into a heated first regenerator and, in the first regenerator, reacting the gaseous reaction mixture and the fuel in an endothermic reaction in the first regenerator to form syngas comprising hydrogen and CO; and
(iv) passing said syngas formed in the first regenerator into said furnace and combusting the syngas with one or more oxidant streams injected into said furnace.

US Pat. No. 10,112,858

MEDIA BED FOR WASTE STREAMS AND METHODS AND SYSTEMS EMPLOYING THE SAME

INTEGRATED AGRICULTURE SY...

1. A method of treating waste comprising:(a) providing an apparatus comprising a media bed comprising a substantially water tight container comprising a biomass, wherein (i) the biomass comprises water and viable worms that are submerged in the water, and (ii) the worms are at a density of about 1000 worms/m3 to about 100,000 worms/m3;
(b) introducing oxygen into the water of the biomass by an aeration means configured to introduce air or oxygen into the water, wherein a dissolved oxygen content of the water is maintained at a level of at least 4 ppm;
(c) maintaining the viable worms in an aquatic environment, wherein the worms are completely and constantly submerged in the water;
(d) contacting the biomass of the apparatus with oxidizable waste, thereby forming a mixture; and
(e) removing a portion of the mixture from the apparatus wherein the portion of the mixture that is removed comprises treated waste.

US Pat. No. 10,112,857

METHOD AND EQUIPMENT FOR THE BIOLOGICAL DENITRIFICATION OF WASTE WATER

DEGREMONT, Paris la Defe...

1. A method for the biological denitrification of wastewater that comprises a nitrification step followed by a denitrification step, for a first fraction of the water, by a post-denitrification step during which an electron donor is injected into this first fraction, whereas a second fraction of the water passes through a bypass, and then is mixed with the first fraction downstream of the post-denitrification step, wherein:the first fraction of the wastewater is submitted, during post-denitrification, to almost complete denitrification in order to exit the step with a concentration of nitrates [N—NO3] below 4 mg/L, to minimize the production of nitrous oxide N2O,
and the bypass rate is determined from:
measurement of the concentration of nitrates [N—NO3] in the water upstream of post-denitrification,
the desired concentration of nitrates [N—NO3] for the mixture of the two fractions downstream of the post-denitrification treatment,
and the concentration of nitrates [N—NO3] in the first fraction at outlet from post-denitrification, before mixing the two fractions.

US Pat. No. 10,112,856

METHOD AND APPARATUS FOR WASTEWATER TREATMENT USING GRAVIMETRIC SELECTION

Hampton Roads Sanitation ...

1. A method for wastewater treatment, comprising:feeding wastewater to an input of a processor that carries out a treatment process on the wastewater;
treating the wastewater in the processor;
outputting processed wastewater at an output of the processor;
feeding the processed wastewater to an input of a gravimetric selector;
selecting, at the gravimetric selector, first solids exhibiting a sludge volume index (SVI) of less than about 120 mL/gm;
outputting a recycle stream at a first output of the gravimetric selector;
outputting a waste stream that comprises solids other than said first solids at a second output of the gravimetric selector to solids handling, where solids handling includes at least one of thickening, stabilizing, conditioning, and dewatering; and
supplying the recycle stream to the processor,
wherein the feeding of the processed wastewater to the input of the gravimetric selector comprises:
feeding the processed wastewater to an input of a separator that separates the wastewater into an underflow and effluent,
receiving the underflow from the separator, and
gravimetrically selecting the first solids from the underflow and supplying the recycle stream to the first output.