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US 2011/0257198 A1Published application
Piperidine derivatives useful as orexin antagonists
OwnerGiuseppe Alvaro, David Amantiniinventors
Life of this patent
Estimating the term…
Abstract
Disclosed are imidazopyridylmethylene substituted piperidine derivatives of Formula (I): useful as orexin antagonists.
Claims21
A compound of formula (I)
- where:
- Ar is pyridinyl substituted with one, two or three groups independently selected from the group consisting of C1-4alkyl, halo, C1-4alkoxy, haloC1-4alkyl, haloC1-4alkoxy, cyano, phenyl or a 5 or 6 membered heterocyclyl group containing 1, 2 or 3 atoms selected from N, O or S, which phenyl or heterocyclyl group is optionally substituted with C1-4alkyl, halo, C1-4alkoxy, haloC1-4alkyl, haloC1-4alkoxy or cyano;
- R1 is (C1-4)alkyl, halo, halo(C1-4)alkyl, (C1-4)alkoxy, halo(C1-4)alkoxy, (C1-4)alkyl-O—(C1-4)alkyl, CN, NR5R6 wherein R5 is H or (C1-4)alkyl and R6 is H or (C1-4)alkyl;
- R2 is (C1-4)alkyl, (C1-4)alkenyl, HO(C1-4)alkyl, halo, halo(C1-4)alkyl, (C1-4)alkoxy, halo(C1-4)alkoxy, (C1-4)alkyl-O—(C1-4)alkyl, CN, NR7R8 wherein R7 is H or (C1-4)-alkyl and R8 is H or (C1-4)-alkyl;
- R3 is (C1-4)alkyl, halo, halo(C1-4)alkyl, (C1-4)alkoxy, halo(C1-4)alkoxy, (C1-4)alkyl-O—(C1-4)alkyl, CN, NR9R10 wherein R9 is H or (C1-4)-alkyl and R10 is H or (C1-4)-alkyl;
- R4 is (C1-4)alkyl, halo, halo(C1-4)alkyl, (C1-4)alkoxy, halo(C1-4)alkoxy, (C1-4)alkyl-O—(C1-4)alkyl, CN, NR11R12 wherein R11 is H or (C1-4)-alkyl and R12 is H or (C1-4)-alkyl;
- n is 0 or 1;
- p is 0 or 1;
- q is 0 or 1;
- r is 0 or 1;
- or a pharmaceutically acceptable salt thereof.
8 more elements
A compound selected from:
- 2-[((2S)-1-{[3-(ethyloxy)-6-methyl-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]-6-fluoro-8-methylimidazo[1,2-a]pyridine;
- 6-fluoro-8-methyl-2-{[(2S)-1-({6-methyl-3-[(2-methylpropyl)oxy]-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}imidazo[1,2-c]pyridine;
- 6,8-dimethyl-2-{[(2S)-1-({6-methyl-3-[(2-methylpropyl)oxy]-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}imidazo[1,2-c]pyridine;
- 8-methyl-2-[((2S)-1-{[6-methyl-3-(propyloxy)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-a]pyridine;
- 2-{[(2S)-1-({3-[(cyclopropylmethyl)oxy]-6-methyl-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}-8-methylimidazo[1,2-a]pyridine;
- 8-methyl-2-{[(2S)-1-({6-methyl-3-[(1-methylethyl)oxy]-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}imidazo[1,2-a]pyridine;
- 2-[((2S)-1-{[4-chloro-3-(ethyloxy)-6-methyl-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]-8-methylimidazo[1,2-a]pyridine;
- 7,8-dimethyl-2-{[(2S)-1-({6-methyl-3-[(2-methylpropyl)oxy]-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}imidazo[1,2-c]pyridine;
- 2-{[(2S)-1-({3-[(cyclopropylmethyl)oxy]-6-methyl-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}-7,8-dimethylimidazo[1,2-c]pyridine;
- 2-[((2S)-1-{[3-(ethyloxy)-6-methyl-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]-7,8-dimethylimidazo[1,2-c]pyridine;
- 7,8-dimethyl-2-[((2S)-1-{[6-methyl-3-(propyloxy)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-a]pyridine;
- 8-fluoro-2-[((2S)-1-{[6-methyl-3-(propyloxy)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-c]pyridine;
- 8-fluoro-2-{[(2S)-1-({6-methyl-3-[(2-methylpropyl)oxy]-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}imidazo[1,2-c]pyridine;
- 2-{[(2S)-1-({3-[(cyclopropylmethyl)oxy]-6-methyl-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}-8-fluoroimidazo[1,2-c]pyridine;
- 6,7-dimethyl-2-{[(2S)-1-({6-methyl-3-[(2-methylpropyl)oxy]-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}imidazo[1,2-a]pyridine;
- 3-chloro-2-{[(2S)-1-({3-[(cyclopropylmethyl)oxy]-6-methyl-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}-8-methylimidazo[1,2-a]pyridine;
- 3-chloro-2-[((2S)-1-{[3-(ethyloxy)-6-methyl-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]-8-methylimidazo[1,2-a]pyridine;
- 2-{[(2S)-1-({3-[(cyclopropylmethyl)oxy]-6-methyl-2-pyridinyl}carbonyl)-2-piperidinyl]methyl}-3,8-dimethylimidazo[1,2-a]pyridine;
- 2-[((2S)-1-{[6-ethyl-3-(ethyloxy)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]-7,8-dimethylimidazo[1,2-a]pyridine;
- 6-fluoro-8-methyl-2-({(2S)-1-[(6-methyl-3-phenyl-2-pyridinyl)carbonyl]-2-piperidinyl}methyl)imidazo[1,2-c]pyridine;
- 7,8-dimethyl-2-[((2S)-1-{[6-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-a]pyridine;
- 7,8-dimethyl-2-[((2S)-1-{[6-methyl-3-(5-methyl-1,3-oxazol-2-yl)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-a]pyridine;
- 2-[((2S)-1-{[3-(5-ethyl-1,3-oxazol-2-yl)-6-methyl-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]-7,8-dimethylimidazo[1,2-a]pyridine;
- 7,8-dimethyl-2-[((2S)-1-{[6-methyl-3-(2-pyrimidinyl)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-a]pyridine;
- 7,8-dimethyl-2-[((2S)-1-{[6-methyl-3-(3-methyl-5-isoxazolyl)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-a]pyridine;
- 7,8-dimethyl-2-[((2S)-1-{[6-methyl-3-(4-methyl-1,3-thiazol-2-yl)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-a]pyridine;
- and
- 6-fluoro-8-methyl-2-[((2S)-1-{[6-methyl-3-(2-pyrimidinyl)-2-pyridinyl]carbonyl}-2-piperidinyl)methyl]imidazo[1,2-c]pyridine;
- or a pharmaceutically acceptable salt thereof.
26 more elements
16-24. (canceled)
(canceled)
Dependencies are inferred from the claim text.