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US 10,239,838 B2Granted
Heteroaryl orexin receptor antagonists
AssigneeMerck Sharp & Dohme Corp.
InventorsScott D. Kuduk, Nigel Liverton, Yunfu Luo
Life of this patent
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Abstract
The present invention is directed to heteroaryl compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
Claims4
A compound of the formula Ia′:
- wherein:
- R1a and R1b are independently selected from the group consisting of:
- (1) hydrogen,
- (2) fluoro,
- (3) chloro,
- (4) methyl,
- (5) methoxy,
- (6) tetrazolyl, and
- (7) triazolyl;
- R3 is methyl or ethyl;
- R5 is —C(CH3)2OH and R6 is hydrogen or methyl;
- or a pharmaceutically acceptable salt thereof.
9 more elements
A compound which is selected from the group consisting of:
- N-ethyl-N-{2-[4-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-ethyl-N-{2[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(1-methylethoxy)pyridine-3-carboxamide;
- 2-ethoxy-N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}pyridine-3-carboxamide;
- 2-(difluoromethoxy)-N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}benzamide;
- N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(trifluoromethoxy)benzamide;
- 2-(2,2-difluoroethoxy)-N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}pyridine-3-carboxamide;
- N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide;
- 2-ethoxy-N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}benzamide;
- N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(1H-pyrazol-1-yl)benzamide;
- N-ethyl-4-fluoro-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-phenylpyridine-3-carboxamide;
- 2-cyclopropyl-N-ethyl-N-{2-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}benzamide;
- N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-2-propylbenzamide;
- N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-2-(2,2,2-trifluoroethoxy)benzamide;
- N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-2-(2,2,2-trifluoroethyl)benzamide;
- 2-cyclopropyl-N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-6-methoxynicotinamide;
- 2-(2,2-difluoroethoxy)-N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)benzamide;
- 2-(2,2-difluoroethyl)-N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)benzamide;
- N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-2-(1H-pyrazol-1-yl)nicotinamide;
- 2-cyclobutyl-N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)benzamide;
- N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-3-phenylpicolinamide;
- N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide;
- N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)-2-(2H-tetrazol-2-yl)benzamide;
- 2-(2,2-difluorocyclopropyl)-N-ethyl-N-(2-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)ethyl)benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-ethyl-N-{2-[2-(1-hydroxy-1-methylethyl)pyridin-4-yl]ethyl}-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-3-yl]ethyl}-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-ethyl-N-(2-(5-(2-hydroxypropan-2-yl)-4-methylpyridin-2-yl)ethyl)-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-Ethyl-N-(2-(6-(2-hydroxypropan-2-yl)-5-methylpyridin-2-yl)ethyl)-2-(2H-1,2,3-triazol-2-yl)benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(1H-pyrazol-1-yl)pyridine-3-carboxamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(trifluoromethoxy)benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-pyrrolidin-1-ylbenzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-propylbenzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(1H-pyrazol-1-yl)benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2,2,2-trifluoroethyl)benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2H-tetrazol-2-yl)benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide;
- 2-ethoxy-N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}benzamide;
- N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-phenylpyridine-3-carboxamide;
- 2-cyclopropyl-N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-6-methoxypyridine-3-carboxamide;
- 2-cyclopropyl-N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}benzamide;
- N-ethyl-4-fluoro-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}-2-(2H-1,2,3-triazol-2-yl)benzamide;
- 2-cyclobutyl-N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}benzamide
- 2-(2,2-difluorocyclopropyl)-N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}benzamide;
- and
- 2-(2,2-difluoroethoxy)-N-ethyl-N-{2-[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]ethyl}pyridine-3-carboxamide;
- or a pharmaceutically acceptable salt thereof.
45 more elements
Dependencies are inferred from the claim text.