8-methyl-1-phenyl-imidazol[1,5-a]pyrazine compounds as Lck inhibitors and uses thereof
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Abstract
The present invention provides 8-methyl-1-phenyl-imidazo[1,5-a]pyrazine derivatives according to formula I or pharmaceutically acceptable salts thereof. The compounds of the current invention show inhibitory activity against Lck and can be used for the treatment of Lck-mediated diseases or Lck-mediated conditions such as inflammatory disorders.
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Citations
12 Claims
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1. A compound according to formula I
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)
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2. The compound according to claim 1 wherein R1 is one or two groups independently selected from hydrogen, hydroxy, (1-3C)alkoxy or halogen.
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3. The compound according to claim 2 wherein
R3 is (R31)(R32)CH— - O;
R31 is (1-5C)alkyl optionally substituted with hydroxy; and R32 is (1-5C)alkyl.
- O;
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4. The compound according to claim 2 wherein
R3 is heteroaryl, which is optionally substituted with one or more groups selected from R34, R35, R36, fluoro, chloro or hydroxy; -
R34 is (1-6C)alkyl; R35 is (1-6C)alkoxy; and R36 is hydrogen or (1-6C)alkyl.
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5. The compound according to claim 4 wherein the heteroaryl group in R3 is
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6. The compound according to claim 5 wherein
R4 is -
7. The compound according to claim 6 wherein
R4 is -
8. The compound according to claim 5 wherein
R4 is -
9. The compound according to claim 8 wherein
R4 is -
10. The compound according to claim 5 wherein R4 is (1-4C)alkyl, optionally substituted independently by one or more substituents from R8, or hydroxy, wherein R8 is heteroaryl.
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11. The Compound according to claim 1 selected from the group consisting of
N-[2-Methoxy-4-[8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazine]phenyl]-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((Trans)-4-(4-acetylpiperazin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-pentan-2-yl 4-(3-(azetidin-1-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (S)-pentan-2-yl 4-(3-((R)-1-(2-(dimethylamino)acetyl)pyrrolidin-3-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (Trans)-4-(1-(3-methoxy-4-(4-methoxy-1-methyl-1H-indole-2-carboxamido)phenyl)-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate, N-(4-(3-((trans)-4-hydroxycyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-((cis)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((trans)-4-(3,3-difluoroazetidin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((cis)-4-(3,3-difluoroazetidin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-Pentan-2-yl 2-methoxy-4-(3-((trans)-4-(2-methoxyethylamino)cyclohexyl)-8-methyl-imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, N-(2-methoxy-4-(8-methyl-3-((trans)-4-morpholinocyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(3-methyloxetan-3-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-(hydroxymethyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((1H-imidazol-1-yl)methyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(1-(tetrahydro-2H-pyran-4-yl)azetidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(piperidin-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-(1-(2-(dimethylamino)-2-oxoethyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-(1-(2-(dimethylamino)acetyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-(1-(2-Aminoacetyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-(1-carbamoylpiperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, Methyl 4-(1-(3-methoxy-4-(4-methoxy-1-methyl-1H-indole-2-carboxamido)phenyl)-8-methylimidazo[1,5-a]pyrazin-3-yl)piperidine-1-carboxylate, N-(2-methoxy-4-(8-methyl-3-(4-methylpiperazin-1-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(2-methoxy-4-(8-methyl-3-(morholin-4-yl) imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, Isopropyl 2-methoxy-4-(8-methyl-3-(4-morpholinopiperidin-1-yl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-Pentan-2-yl 2-methoxy-4-(3-((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, N-(4-(3-((Trans)-4-(dimethylamino)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(3-((cis)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-((cis)-4-morpholinocyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((Cis)-4-(dimethylamino)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-Pentan-2-yl 4-(3-((cis)-4-(4-acetylpiperazin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (S)-Pentan-2-yl 4-(3-((cis)-4-(3,3-difluoroazetidin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (S)-Pentan-2-yl 2-methoxy-4-(8-methyl-3-((1r,3r)-3-(4-methylpiperazin-1-yl)cyclobutyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-Pentan-2-yl 2-methoxy-4-(8-methyl-3-(3-(4-methylpiperazin-1-yl)cyclopentyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-Pentan-2-yl 2-methoxy-4-(3-((trans)-4-(N-(2-methoxyethyl)acetamido)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, (S)-Pentan-2-yl 4-(3-(4-acetylpiperazin-1-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, N-(4-(3-(4-(1-Acetylpiperidin-4-yl)piperazin-1-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-Pentan-2-yl 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, N-(2-Methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide 2,2,2-trifluoroacetate, N-(4-(3-((Trans)-4-(4-acetylpiperazin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide, (S)-Pentan-2-yl 4-(3-((trans)-4-(4-acetylpiperazin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (R)— - N-(4-(3-(1-(2-(Dimethylamino)acetyl)pyrrolidin-3-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide,
(S)-Pentan-2-yl 2-methoxy-4-(8-methyl-3-((cis)-4-(4-methylpiperazin-1-yl)cyclohexyl) imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, N-(4-(3-(4-Acetylpiperazin-1-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(4-(tetrahydro-2H-pyran-4-yl)piperazin-1-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, (R)-4-methoxy-N-(2-methoxy-4-(8-methyl-3-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, (S)-4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(1-methyl-2-oxopiperidin-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((trans)-4-aminocyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((trans)-4-(2,2-Difluoroethylamino)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, Isopropyl 4-(3-((trans)-4-(3,3-difluoroazetidin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl(methyl)carbamate, 5-Methoxy-N-(2-methoxy-4-(8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxamide, N-(2-Methoxy-4-(8-methyl-3-(1-methylpiperidin-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, (S)-4-Hydroxybutan-2-yl 2-methoxy-4-(8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, 4-Fluoro-N-(2-methoxy-4-(8-methyl-3-(1-methylpiperidin-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(5-Fluoro-2-methoxy-4-(8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, 5-Hydroxypentan-2-yl 5-fluoro-2-methoxy-4-(8-methyl-3-(tetrahydro-2h-pyran-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-sec-Butyl 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, N-(4-(3-(1′
-acetyl-1,4′
-bipiperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide,(S)-pentan-2-yl 2-methoxy-4-(3-((S)-1-(2-methoxyacetyl)pyrrolidin-3-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (trans)-4-(1-(3-Methoxy-4-(4-methoxy-1-methyl-1H-indole-2-carboxamido)phenyl)-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl cyclopentylcarbamate, (R)—
N-(4-(3-(1-(2-(dimethylamino)-2-oxoethyl)pyrrolidin-3-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide,(R)—
N-(4-(3-(1-(2-hydroxyacetyl)pyrrolidin-3-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide,4-Methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(piperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Chloro-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-pyrrole-2-carboxamide, N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-6-methyl-6H-thieno[2,3-b]pyrrole-5-carboxamide, N-(2-Methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-6H-thieno[2,3-b]pyrrole-5-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1H-indole-2-carboxamide, 4-Hydroxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, (S)-Pentan-2-yl 4-(3-((trans)-4-(aminomethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, 1-Methyl-N-(4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1H-indole-2-carboxamide, N-(2-hydroxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-((methylamino)methyl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((trans)-4-((dimethylamino)methyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-Pentan-2-yl 4-(3-((trans)-4-((dimethylamino)methyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, 6-Methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1H-indazole-3-carboxamide, 5-Chloro-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide, N-(4-(3-((trans)-4-(acetamidomethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-pentan-2-yl 4-(3-((trans)-4-(acetamidomethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (S)-pentan-2-yl 4-(3-((trans)-4-(methoxycarbonylmethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(4-oxocyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((trans)-4-hydroxy-4-((methylamino)methyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-(1-methyl-5-oxopyrrolidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-Methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methyl-3-oxopiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 5-Methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide, 4-methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-morpholinocyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, (S)-pentan-2-yl 2-methoxy-4-(8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-pentan-2-yl 2-methoxy-4-(8-methyl-3-((trans)-4-morpholinocyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-pentan-2-yl 4-(3-(1-(2-(dimethylamino)acetyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (S)-pentan-2-yl 4-(3-(1-(2-(dimethylamino)-2-oxoethyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (S)-pentan-2-yl 2-methoxy-4-(8-methyl-3-morpholinoimidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, isopropyl 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, 4-fluoro-N-(2-methoxy-4-(8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, tert-butyl 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, N-(4-(3-(1-(2-(dimethylamino)-2-oxoethyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, N-(4-(3-(azetidin-1-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide, 5-hydroxypentan-2-yl 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-pentan-2-yl 4-(3-(1-(2-aminoacetyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, N-(4-(3-(1-(2-aminoacetyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, N-(4-(3-((trans)-4-(aminomethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-pentan-2-yl 2-methoxy-4-(8-methyl-3-((cis)-4-morpholinocyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, (S)-pentan-2-yl 2-methoxy-4-(8-methyl-3-(4-morpholinopiperidin-1-yl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, 4-methoxy-N-(2-methoxy-4-(8-methyl-3-(4-morpholinopiperidin-1-yl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-3-(4-methylpiperazin-1-yl)cyclobutyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-methoxy-N-(2-methoxy-4-(3-((trans)-4-(2-methoxyethylamino)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-methoxy-N-(2-methoxy-4-(3-((trans)-4-(N-(2-methoxyethyl)acetamido)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-methoxy-N-(2-methoxy-4-(8-methyl-3-morpholinoimidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, 4-methoxy-N-(2-methoxy-4-(3-((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide, N-(4-(3-(1-(2-(dimethylamino)acetyl)piperidin-4-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide, (S)-pentan-2-yl 4-(3-((trans)-4-(3,3-difluoroazetidin-1-yl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate, (S)-pentan-2-yl 2-methoxy-4-(8-methyl-3-(4-(tetrahydro-2H-pyran-4-yl)piperazin-1-yl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate, and N-(4-(3-((trans)-4-(3,3-difluoroazetidin-1-ypcyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide.
- N-(4-(3-(1-(2-(Dimethylamino)acetyl)pyrrolidin-3-yl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide,
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12. A method of modulating lymphocite specific kinase activity in a subject comprising administering to the subject an amount of a compound of claim 1.
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2. The compound according to claim 1 wherein R1 is one or two groups independently selected from hydrogen, hydroxy, (1-3C)alkoxy or halogen.
Specification
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Current AssigneeMerck Sharp & Dohme LLC (Merck & Co., Inc.)
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Original AssigneeMerck Sharp & Dohme BV (Merck & Co., Inc.)
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Inventorsde Man, Adrianus Petrus Antonius, Rewinkel, Johannes Bernardus Maria, Wijkmans, Jacobus Cornelis Henricus Maria, Jans, Christiaan Gerardus Johannes Maria, Raaijmakers, Hans Cornelis Andreas
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Primary Examiner(s)Willis, Douglas M
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Application NumberUS13/577,417Publication NumberTime in Patent Office1,118 DaysField of Search544/117, 544/350, 544/359, 546/118, 546/199, 548/335.1, 548/469, 548/518, 548/950, 549/50, 549/356, 549/510US Class Current544/350CPC Class CodesA61P 11/00 Drugs for disorders of the ...A61P 11/06 AntiasthmaticsA61P 13/12 of the kidneysA61P 17/06 AntipsoriaticsA61P 19/02 for joint disorders, e.g. a...A61P 29/00 Non-central analgesic, anti...A61P 3/10 for hyperglycaemia, e.g. an...A61P 35/02 specific for leukemiaA61P 37/00 Drugs for immunological or ...A61P 37/06 Immunosuppressants, e.g. dr...A61P 37/08 Antiallergic agents antiast...A61P 43/00 Drugs for specific purposes...A61P 9/10 for treating ischaemic or a...C07D 487/04 Ortho-condensed systemsC07D 519/00 Heterocyclic compounds cont...