BTK Inhibitors
US-9718828-B2 · Aug 1, 2017 · US
Benzamide imidazopyrazine Btk inhibitors
US10087188B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10087188-B2 |
| Application number | US-201515538902-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 17, 2015 |
| Priority date | Dec 31, 2014 |
| Publication date | Oct 2, 2018 |
| Grant date | Oct 2, 2018 |
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- Title
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Abstract
Official abstract text for this publication.
The present invention provides Bruton's Tyrosine Kinase (Btk) inhibitor compounds according to Formula (I), or pharmaceutically acceptable salts thereof, or to pharmaceutical compositions comprising these compounds and to their use in therapy. In particular, the present invention relates to the use of Btk inhibitor compounds of Formula (I) in the treatment of Btk mediated disorders.
First claim
Opening claim text (preview).
What is claimed is: 1. A compound selected from the group consisting of: (1R,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclohexanecarboxylic acid; (1S,3R)-3-(8-amino-1-{4-[(4-cyclopropylpyridin-2-yl)carbamoyl]phenyl}imidazo[1,5-a]pyrazin-3-yl)cyclohexanecarboxylic acid; (1R,3S)-3-(8-amino-1-{4-[(4-cyclopropylpyridin-2-yl)carbamoyl]phenyl}imidazo[1,5-a]pyrazin-3-yl)cyclohexanecarboxylic acid; (1R,3S)-3-[8-amino-1-(2-methoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclohexanecarboxylic acid; (1S,3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclohexanecarboxylic acid (1S,3R)-3-(8-amino-1-{4-[(4-ethylpyridin-2-yl)carbamoyl]phenyl}imidazo[1,5-a]pyrazin-3-yl)cyclohexanecarboxylic acid; (1S,3R)-3-(8-amino-1-{4-[(4-cyclopropylpyridin-2-yl)carbamoyl]phenyl}imidazo[1,5-a]pyrazin-3-yl)cyclohexanecarboxylic acid; (1S,3R)-3-(8-amino-1-{4-[(4-cyclopropylpyridin-2-yl)carbamoyl]-2-fluorophenyl}imidazo[1,5-a]pyrazin-3-yl)cyclohexanecarboxylic acid; (1S,3R)-3-[8-amino-1-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl) imidazo[1,5-a]pyrazin-3-yl]cyclohexanecarboxylic acid; (1S,3R)-3-[8-amino-1-(2-methoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl) imidazo[1,5-a]pyrazin-3-yl]cyclohexanecarboxylic acid; (1S,3R)-3-[8-amino-1-(4-{[4-(cyclopropyloxy)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclohexanecarboxylic acid; (1S,3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentanecarboxylic acid; (1R,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentanecarboxylic acid; 1-[({S,3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}carbonyl)amino]cyclopropanecarboxylic acid; 1-({(1R,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}carbonyl)-L-proline; 1-({(1R,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}carbonyl)-D-proline; (3R)-1-({(1R,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}carbonyl)pyrrolidine-3-carboxylic acid; 4-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-2,2-dimethylcyclohexanecarboxylic acid; (1S,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1,3-dimethylcyclopentanecarboxylic acid; (1S,3S)-3-[8-amino-1-(2-ethoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl) imidazo[1,5-a]pyrazin-3-yl]-1,3-dimethylcyclopentanecarboxylic acid; 3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]benzoic acid; 5-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-2-fluorobenzoic acid; 4-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-2-fluorobenzoic acid; 4-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]benzoic acid; 5-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1H-pyrrole-2-carboxylic acid; 5-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]furan-2-carboxylic acid; 5-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]pyridine-2-carboxylic acid; 4-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1,4-dimethylcyclohexanecarboxylic acid; (2R,4S)-4-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]piperidine-2-carboxylic acid; (2S,4R)-4-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]piperidine-2-carboxylic acid; (2R,4R)-4-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]piperidine-2-carboxylic acid; (3R)-1-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidine-3-carboxylic acid; (1S,3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclopentanecarboxylic acid; (3S)-1-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidine-3-carboxylic acid; (3R)-1-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-3-methylpiperidine-3-carboxylic acid; (3S)-1-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-3-methylpiperidine-3-carboxylic acid; (3R)-1-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-3-methylpyrrolidine-3-carboxylic acid; (3S)-1-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-3-methylpyrrolidine-3-carboxylic acid; (1R, 3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1R,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1S,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; {(1R,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}acetic acid; {(1S,3S)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}acetic acid; (1S,3R)-3-[8-amino-1-(2-ethoxy-4-{[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1S,3S)-3-[8-amino-1-(2-ethoxy-4-{[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl] carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; {(1S,3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}acetic acid; {(1R, 3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]cyclopentyl}acetic acid; (1R,3S)-3-[8-amino-1-(2-ethoxy-4-{[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1R,3R)-3-[8-amino-1-(2-ethoxy-4-{[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl] carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1S,3R)-3-[8-amino-1-(2-ethoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl) imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1R, 3R)-3-[8-amino-1-(2-ethoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl) imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1R,3S)-3-[8-amino-1-(2-ethoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1S,3S)-3-[8-amino-1-(2-ethoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl) imidazo[1,5-a]pyrazin-3-yl]-1-(1-methylethyl)cyclopentanecarboxylic acid; (1S,3R)-3-[8-amino-1-(4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}phenyl)imidazo[1,5-a]pyrazin-3-yl]-1,2,2-trimethylcyclopentanecarboxylic acid; 4-(8-amino-1-(2-fluoro-4-((4-(trifluoromethyl)pyridin-2-yl)carbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)cubane-1-carboxylic acid; 4-(8-amino-1-(2-ethoxy-4-((4-(trifluoromethyl)pyridin-2-yl)carbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)cubane-1-carboxylic acid; (1R,3S)-3-[8-amino-1-(2-ethoxy-4-{[4-(trifluoromethyl)pyridin-2-yl]carbamoyl}pheny
Assignees
Inventors
Classifications
- C07D487/04Primary
Ortho-condensed systems · CPC title
Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title
not condensed and containing further heterocyclic rings, e.g. timolol · CPC title
Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems · CPC title
Immunomodulators · CPC title
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Frequently asked questions
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- What does patent US10087188B2 cover?
- The present invention provides Bruton's Tyrosine Kinase (Btk) inhibitor compounds according to Formula (I), or pharmaceutically acceptable salts thereof, or to pharmaceutical compositions comprising these compounds and to their use in therapy. In particular, the present invention relates to the use of Btk inhibitor compounds of Formula (I) in the treatment of Btk mediated disorders.
- Who is the assignee on this patent?
- Merck Sharp & Dohme
- What technology area does this patent fall under?
- Primary CPC classification C07D487/04. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Oct 02 2018 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 2 related publications on this page (citations in our corpus or others sharing the same primary CPC).