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US 8,133,908 B2Granted
Heteroaryl derivatives of N-{[(1S,4S,6S)-3-(2-pyridinylcarbonyl)-3-azabicyclo[4.1.0]hept-4-yl]methyl}-2-amine
AssigneeGlaxo Group Limited
InventorsGiuseppe Alvaro, David Amantini, Emiliano Castiglioni, Romano Di Fabio, Francesca Pavone
Life of this patent
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Abstract
Disclosed are N-{[(1S,4S,6S)-3-(2-pyridinylcarbonyl)-3-azabicyclo[4.1.0]hept-4-yl]methyl}-2-heteroarylamine derivatives having the following formula: wherein m, n, Het, R1, R2 and R3 are as defined herein, and their use as orexin antagonists.
Claims16
A compound of formula (I)
- where:
- Het is a heteroaryl group selected from the group consisting of pyridinyl, pyrimidinyl, pyridazinyl or pyrazinyl, said heteroaryl group being optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of:
- C1-4alkyl, halo, C1-4alkoxy, haloC1-4alkyl, haloC1-4alkoxy and cyano;
- R1 is C 1-4alkyl, halo, C1-4alkoxy, haloC1-4alkyl, haloC1-4alkoxy, cyano, C1-4alkylSO2, C3-8 cycloalkylSO2, C3-8cycloalkylCH2SO2, 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;
- R2 is 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;
- R3 is C1-4alkyl, halo, C1-4alkoxy, haloC1-4alkyl, haloC1-4alkoxy or cyano;
- m is 0 or 1;
- and
- n is 0 or 1;
- or a pharmaceutically acceptable salt thereof.
7 more elements
A compound selected from the group consisting of:
- N-[((1S,4S,6S)-3-{[6-methyl-3-(propyloxy)-2-pyridinyl]carbonyl}-3 -azabicyclo[4.1.0]hept-4-yl)methyl]-5-(trifluoromethyl)-2-pyridinamine;
- N-[((1S,4S,6S)-3-{[3-(ethyloxy)-6-methyl-2-pyridinyl]carbonyl}-3 -azabicyclo [4.1.0]hept-4-yl)methyl]-5 -(trifluoromethyl)-2-pyridinamine;
- N-[((1S,4S,6S)-3-{[6-methyl-3-(2-pyrimidinyl)-2-pyridinyl]carbonyl}-3 -azabicyclo[4.1.0]hept-4-yl)methyl]-5-(trifluoromethyl)-2-pyridinamine;
- N-[((1S,4S,6S)-3-{[6-methyl-3-(2-pyrimidinyl)-2-pyridinyl]carbonyl}-3-azabicyclo[4.1.0]hept-4-yl)methyl]-5-(trifluoromethyl)-2-pyrazinamine;
- N-[((1 S,4S,6S)-3-{[6-methyl-3-(1H-pyrazol-1-yl)-2-pyridinyl]carbonyl}-3-azabicyclo[4.1.0]hept-4-yl)methyl]-5-(trifluoromethyl)-2-pyrazinamine;
- and
- N-[((1S,4S,6S)-3-{[6-methyl-3-(2H-1,2,3-triazol-2-yl)-2-pyridinyl]carbonyl}-3-azabicyclo[4.1.0]hept-4-yl)methyl]-5-(trifluoromethyl)-2-pyrazinamine;
- or a pharmaceutically acceptable salt thereof.
5 more elements
Dependencies are inferred from the claim text.