Derivatives of azaspiranyl-alkylcarbamates of 5-member heterocyclic compounds, preparation thereof and therapeutic use thereof

Inventors: Ahmed Abouabdellah (Paris, FR); Nathalie Chereze (Paris, FR); Aude Fayol (Paris, FR); Alistair Lochead (Paris, FR); Mourad Saady (Paris, FR); Julien Vache (Paris, FR); Philippe Yaiche (Paris, FR)

Assignee: Sanofi

C07D417/14 C07D413/14

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Quick Facts

Patent No.: US 8,889,702
App. No.: 13/145,926
Granted: Nov 18, 2014
Kind: B2

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Abstract

The invention relates to a compound of the general formula (I) in which R 2 is a hydrogen or fluorine atom or a hydroxyl, cyano, trifluoromethyl, C 1-6 -alkyl, C 1-6 -alkoxy, NR 8 R 9 group; m, n, o and p are independently an integer equal to 0, 1, 2 or 3; A is a covalent bond or a C 1-8 -alkylene group; R 1 is an optionally substituted aryl or heteroaryl group; R 3 is a hydrogen or fluorine atom or a C 1-6 -alkyl group or a trifluoromethyl group; R 4 is an optionally substituted 5-member heterocyclic compound; the compound being in the form of a base or acid addition salt. The invention also relates to the therapeutic use thereof.

Claims (89)

1. Compound corresponding to formula (I)

in which

R 2 represents a hydrogen or fluorine atom or a hydroxyl, cyano, trifluoromethyl, C 1-6 -alkyl, C 1-6 -alkoxy or NR 8 R 9 group;

m, n, o and p represent, independently of each other, an integer equal to 0, 1, 2 or 3;

A represents a covalent bond or a group C 1-8 -alkylene;

R 1 represents a group R 5 optionally substituted with one or more groups R 6 and/or R 7 ;

R 5 represents a group chosen from phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, naphthyl, quinolinyl, isoquinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, cinnolinyl and naphthyridinyl;

R 6 represents a halogen atom or a C 1-6 -alkyl, or C 1-6 -haloalkyl group;

R 7 represents phenyl ring optionally substituted with one or more groups R 6 that may be identical to or different from each other;

R 3 represents a hydrogen or fluorine atom, a group C 1-6 -alkyl or a trifluoromethyl group;

R 4 represents a group chosen from furyl, pyrrolyl, thienyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, imidazolyl, triazolyl and tetrazolyl;

this group being optionally substituted with one or more substituents chosen from a halogen atom, a group C 1-6 -alkyl, C 1-6 -haloalkyl, C 3-7 -cycloalkyl, C 3-7 -cycloalkyl-C 1-3 -alkylene, C 1-6 -haloalkoxy, cyano, NR 8 R 9 , NR 8 COR 9 , NR 8 CO 2 R 9 , NR 8 SO 2 R 9 , NR 8 SO 2 NR 8 R 9 , COR 8 , CO 2 R 8 , CONR 8 R 9 , CON(R 8 )(C 1-3 -alkylene-NR 10 R 11 ), SO 2 R 8 , SO 2 NR 8 R 9 , —O—(C 1-3 -alkylene)-O—, and phenyl; the phenyl groups possibly being substituted with one or more substituents chosen from a halogen atom and a cyano, nitro, C 1-6 -alkyl, C 1-6 -alkoxy, C 1-6 -thioalkyl, C 1-6 -haloalkoxy, C 1-6 -halothioalkyl, C 3-7 -cycloalkyl or C 3-7 -cycloalkyl-C 1-3 -alkylene group; R 8 and R 9 represent, independently of each other, a hydrogen atom or a group C 1-6 -alkyl, R 10 and R 11 represent, independently of each other, a hydrogen atom or a group C 1-6 -alkyl;