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US 8,912,188 B2Granted
Substituted quinoxaline carboxylic acids for the inhibition of PASK
AssigneeBioEnergenix LLC
InventorsJohn M. McCall, Donna L. Romero, Robert C. Kelly
Life of this patent
Estimating the term…
Abstract
Disclosed herein are substituted quinoxaline carboxylic acids of Formula (I): and compositions thereof, which may be useful as inhibitors of PAS Kinase (PASK) activity in a human or animal for the treatment of diseases such as diabetes mellitus.
Claims8
A compound chosen from
- 2-(Benzofuran-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(1H-pyrazol-4-yl)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(6-methoxypyridin-3-yl)quinoxaline-6-carboxylic acid,
- 2-(1H-Indazol-6-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(1-methyl-1H-indazol-6-yl)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(5-methoxy-1H-indol-2-yl)quinoxaline-6-carboxylic acid,
- 2-(5-Bromopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(1H-Indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(3-(trifluoromethyl)-1H-pyrazol-4-yl)quinoxaline-6-carboxylic acid,
- 2-(6-(tent-Butoxycarbonylamino)pyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(2-Fluoropyridin-4-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)quinoxaline-6-carboxylic acid,
- 2-(6-Fluoropyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- (S)-2-(Benzofuran-2-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(Benzofuran-2-yl)-3-(cyclopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(6-Aminopyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(5-methoxybenzofuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-(5-Fluorobenzofuran-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(5-Chlorobenzofuran-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(Chroman-6-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(Benzo[d]oxazol-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(Benzo[b]thiophen-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(5-Fluorobenzo[b]thiophen-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(1-methyl-1H-indazol-5-yl)quinoxaline-6-carboxylic acid,
- 2-(1-Ethyl-1H-indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(1-Benzofuran-2-yl)-3-(diethylamino)quinoxaline-6-carboxylic acid,
- 2-(6-Fluoro-1-benzofuran-2-yl)-3-[(2S)-2-methylpiperidin-1-yl]quinoxaline-6-carboxylic acid,
- 3-(Cyclopropyl(methyl)amino)-2-(1H-indazol-5-yl)quinoxaline-6-carboxylic acid,
- 2-(1-Benzofuran-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 2-(6-Chloro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- (S)-2-(6-Fluorobenzofuran-2-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(5,6-Difluorobenzofuran-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- (S)-2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(1H-Indazol-5-yl)-3-(piperidin-1-yl)quinoxaline-6-carboxylic acid,
- 3-(Azepan-1-yl)-2-(1H-indazol-5-yl)quinoxaline-6-carboxylic acid,
- 3-(Azepan-1-yl)-2-(1H-indol-5-yl)quinoxaline-6-carboxylic acid,
- 3-(Diethylamino)-2-(1H-indol-5-yl)quinoxaline-6-carboxylic acid,
- 3-(Azepan-1-yl)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(1H-Indol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(5-Fluorobenzofuran-2-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(1H-pyrazol-5-yl)quinoxaline-6-carboxylic acid,
- 2-(3-Methyl-1H-indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(6-Fluoro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(quinolin-6-yl)quinoxaline-6-carboxylic acid,
- 2-(1H-Indazol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- 3-(Azepan-1-yl)-2-(6-fluoro-1-benzofuran-2-yl)quinoxaline-6-carboxylic acid,
- 3-(Cyclopropyl(methyl)amino)-2-(6-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-(1,2-Benzoxazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 3-(Azepan-1-yl)-2-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-(Benzo[b]thiophen-2-yl)-3-(piperidin-1-yl)quinoxaline-6-carboxylic acid,
- 3-(Azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(5-Fluorobenzo[b]thiophen-2-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(Benzo[d]thiazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(1,3-Benzothiazol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- 2-(1,3-Benzothiazol-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 2-(1,3-Benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2,7′-biquinoxaline-6-carboxylic acid,
- 3-[Cyclopropyl(methyl)amino]-2-(5-fluoro-1-benzofuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-(5-Fluoro-1-benzofuran-2-yl)-3-(pyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(1H-Benzo[d]imidazol-1-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-[Cyclopropyl(methyl)amino]-2-(1H-indol-5-yl)quinoxaline-6-carboxylic acid,
- 2-(1H-Indol-5-yl)-3-(piperidin-1-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(1H-Indol-5-yl)-3-(3-methylmorpholino)quinoxaline-6-carboxylic acid,
- 2-(1H-Indol-5-yl)-3-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- 2-(5-Fluoro-1-benzofuran-2-yl)-3-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- (S)-3-(sec-Butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-(1-Benzofuran-2-yl)-3-[(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-[5-(trifluoromethyl)-1-benzofuran-3-yl]quinoxaline-6-carboxylic acid,
- 2-(1-Benzofuran-3-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- (S)-2-(1H-Indol-5-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid,
- (R)-3-(sec-Butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-(2-Methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-(Furan-3-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylic acid,3-[(2S)-2-methylpyrrolidin-1-yl]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylic acid,
- 2-(1-Benzofuran-3-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(3-phenylfuran-2-yl)quinoxaline-6-carboxylic acid,
- 2-[5-(4-Fluorophenyl)furan-2-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(3-methyl-1-benzofuran-5-yl)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid,
- (R)-2-(Benzo[d][1,3]dioxol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(2-Methyl-1H-indol-5-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid,
- 3-[Cyclopropyl(methyl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(1-methyl-1H-pyrazol-4-yl)quinoxaline-6-carboxylic acid,
- 3-[Methyl(propan-2-yl)amino]-2-(1-phenyl-1H-pyrazol-4-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(1H-indazol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylic acid,
- (S)-7-Hydroxy-2-(1H-indazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(1H-Benzo[d][1,2,3]triazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(1H-Benzo[d][1,2,3]triazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 3-(Benzyl(methyl)amino)-2-(1H-indazol-5-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(1H-Indazol-5-yl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylic acid,
- (S)-2-(2-Methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(5-Fluorobenzofuran-2-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid,
- (R)-2-(4-Fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(methyl(tetrahydro-2H-pyran-4-yl)amino)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(methyl(piperidin-4-yl)amino)quinoxaline-6-carboxylic acid,
- (S)-3-(sec-Butyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- (S)-2-(4-Fluorophenyl)-3-(3-methylmorpholino)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-[(2R)-2-(trifluoromethyl)piperidin-1-yl]quinoxaline-6-carboxylic acid,
- 3-(tert-Butyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(Cyclohexyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(methyl(o-tolyl)amino)quinoxaline-6-carboxylic acid,
- 3-(tert-Butylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(Ethyl(isopropyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-[Cyclohexyl(ethyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(Diethylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-[(2S)-2-methylpiperazin-1-yl]quinoxaline-6-carboxylic acid,
- (S)-2-(2,4-Difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(2,4-Difluorophenyl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid,
- (S)-2-(4-Fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluoro-2-methylphenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(4-Carbamoylphenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-7-hydroxy-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid,
- (R)-2-(4-Fluorophenyl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-7-methoxy-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 7-Fluoro-2-(4-fluorophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-[methyl(2,2,2-trifluoroethyl)amino]quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(((1r,4r)-4-hydroxycyclohexyl)(methyl)amino)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(methyl((1r,4r)-4-(methylamino)cyclohexyl)amino)quinoxaline-6-carboxylic acid,
- 3-(((1r,4r)-4-Acetamidocyclohexyl)(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(4-Acetylpiperazin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(4-Benzoylpiperazin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(4-(methylsulfonyl)piperazin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-[4-(pyridin-2-yl)piperidin-1-yl]quinoxaline-6-carboxylic acid,
- (S)-2-(4-Fluorophenyl)-7-hydroxy-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 3-[Benzyl(methyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-[methyl(pyridin-2-ylmethyl)amino]quinoxaline-6-carboxylic acid,
- 3-(Cyclopentyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(Isopropyl(methyl)amino)-2-(4-(trifluoromethyl)phenyl)quinoxaline-6-carboxylic acid,
- 3-[(1-Ethylpiperidin-4-yl)(methyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- (S)-3-(4-Ethyl-2-methylpiperazin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-[Ethyl(propyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(Dipropylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(isobutyl(methyl)amino)quinoxaline-6-carboxylic acid,
- 3-(2-Ethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- (S)-2-(4-Fluorophenyl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylic acid,
- 2-(4-Fluorophenyl)-3-(pyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 3-(Azetidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 3-(Cyclobutyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid,
- 2-(2,4-Difluorophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid,
- (S)-2-(3,4-Difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid,
- 2-(4-Acetamidophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid, and
- (R)-2-(4-Fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid.
146 more elements
Dependencies are inferred from the claim text.