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US 2016/0244445 A1Published application
4-Azaindole Derivatives
AssigneeEisai R&D Management Co., Ltd.
InventorsAndrew Payne, Jose Luis Castro Pineiro, Louise Michelle Birch, Afzal Khan, Alan James Braunton, James Edward Kitulagoda, Motohiro Soejima
Life of this patent
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Abstract
4-Azaindole derivatives which are modulators of muscarinic acetylcholine receptor (mAChR) M1 and which may be effective for the prevention or disease modifying or symptomatic treatment of cognitive deficits associated with neurological disorders such as Alzheimer-type dementia (AD) or dementia with Lewy bodies (DLB), and a pharmaceutical composition comprising a 4-azaindole derivative as an active ingredient.
Claims16
A compound or a pharmaceutically acceptable salt thereof, which is
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(3,5-difluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(2,5-difluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(3-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluoro-3-methylbenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(2,3-difluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-(trifluoromethoxy)benzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(2,3-difluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-methoxybenzyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(3-fluoro-4-methoxybenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-1-(4-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-1-(2,3-difluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((6-methylpyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-1-((5-fluoropyridin-2-yl)methyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(2-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-chlorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(2,4-difluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluorobenzyl)-N-(trans-2-hydroxycycloheptyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluorobenzyl)-N-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-cyano-1-(4-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-cyano-N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-(trifluoromethyl)benzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-(trans-4,4-difluoro-2-hydroxycyclohexyl)-1-(4-fluorobenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-(1H-pyrazol-1-yl)benzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-(1H-pyrazol-1-yl)benzyl)-5-cyano-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-(1-methyl-1H-imidazol-2-yl)benzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-(1-methyl-1H-imidazol-4-yl)benzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(2-fluoro-4-(6-methylpyridin-2-yl)benzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(2-fluoro-4-(2-methylpyridin-4-yl)benzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-((4′-fluoro-[1,1′-biphenyl]-4-yl)methyl)-N-(trans-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-(1H-pyrazol-1-yl)benzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-(1H-pyrazol-1-yl)benzyl)-N-((1R,2R)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-(1H-pyrazol-1-yl)benzyl)-N-cyclohexyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-(1H-pyrazol-1-yl)benzyl)-N-(4,4-difluorocyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- (S)-1-(4-(1H-pyrazol-1-yl)benzyl)-N-(piperidin-3-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- (S)-1-(4-(1H-pyrazol-1-yl)benzyl)-N-(1-methylpiperidin-3-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- (R)-1-(4-(1H-pyrazol-1-yl)benzyl)-N-(1-methylpiperidin-3-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-bromobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-(1-methyl-1H-pyrazol-4-yl)benzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-((6-chloropyridin-3-yl)methyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-chlorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((5-methylpyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((6-methylpyridin-3-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1-((5-methylpyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(3-fluorobenzyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-methoxy-3-methylbenzyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-((6-methoxypyridin-3-yl)methyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((6-methoxypyridin-3-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((2-methoxypyridin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-1-((6-cyanopyridin-3-yl)methyl)-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-((2-methoxypyridin-4-yl)methyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((4-methylthiazol-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((5-methylthiazol-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-((2-methylpyridin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-((1S,2S)-2-hydroxycyclohexyl)-1-(pyridin-4-ylmethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1 ((2-methylpyridin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-(pyridin-4-ylmethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1-((4-methylpyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-((5-chloropyridin-2-yl)methyl)-N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-fluorobenzyl)-N-(trans-3-hydroxytetrahydro-2H-pyran-4-yl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(4-methoxybenzyl)-N-(trans-3-hydroxytetrahydro-2H-pyran-4-yl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 1-(3-fluoro-4-methoxybenzyl)-N-(trans-3-hydroxytetrahydro-2H-pyran-4-yl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- N-(trans-3-hydroxytetrahydro-2H-pyran-4-yl)-1-((2-methoxypyridin-4-yl)methyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-1-(3-fluorobenzyl)-N-(trans-3-hydroxytetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-1-(4-methoxybenzyl)-N-(trans-3-hydroxytetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- 7-chloro-1-(4-fluorobenzyl)-N-((3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;
- or
- 7-chloro-1-(4-fluorobenzyl)-N-((3S,4R)-3-hydroxytetrahydro-2H-pyran-4-yl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide.
72 more elements
A compound of formula (IA), or a pharmaceutically acceptable salt thereof,
- wherein
- R1 is hydrogen, halogen, cyano, C1-4alkyl or C1-4alkoxy;
- R2 is hydrogen;
- p is 1 or 2 and each R4 is independently selected from halogen, C1-4alkyl, C1-4alkoxy, C1-4haloalkyl and C1-4 haloalkoxy.
1 more element
A compound of formula (IB), or a pharmaceutically acceptable salt thereof,
- wherein
- R1 is hydrogen, halogen, C1-4alkyl or C1-4alkoxy;
- R2 is hydrogen;
- R4a is hydrogen or halogen;
- R4b is hydrogen, halogen, C1-4alkyl, C1-4alkoxy, C1-4haloalkyl or C1-4haloalkoxy;
- R4c is hydrogen, halogen, C1-4alkyl, C1-4alkoxy or C1-4haloalkyl;
- and
- R4d is hydrogen or halogen,
- wherein at least one of R4a, R4b, R4c and R4d is other than hydrogen and no more than two of R4a, R4b, R4c and R4d are hydrogen.
6 more elements
Dependencies are inferred from the claim text.