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US 7,745,467 B2Granted
N-(heteroaryl)-1-heteroarylalkyl-1H-indole-2-carboxamide derivatives, preparation and therapeutic use thereof
AssigneeSanofi-Aventis
InventorsLaurent Dubois, Yannick Evanno, Andre Malanda
Life of this patent
Estimating the term…
Abstract
The invention concerns compounds of general formula (I), wherein n, X1, X2, X3, X4, Y and W are as defined herein. The invention also concerns a method for preparing said compounds and their therapeutic use.
Claims15
A compound of formula (I)
- wherein:
- X1, X2, X3 and X4 represent, independently of each other, a hydrogen or halogen atom, a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C1-C6-fluoroalkoxy, cyano, C(O)NR1R2, nitro, NR1R2, C1-C6-thioalkyl, —S(O)—C1-C6-alkyl, —S(O)2—C1-C6-alkyl, SO2NR1R2, NR3COR4, NR3SO2R5 or aryl group, the aryl being optionally substituted with one or more substituents chosen from a halogen and a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C1-C6-fluoroalkoxy, nitro or cyano group;
- W represents a fused bicyclic group of formula:
- bonded to the nitrogen atom via positions 1, 2, 3 or 4;
- wherein
- A represents a 5- to 7-membered heterocycle comprising from one to three heteroatoms chosen from O, S and N;
- the carbon atom(s) of A being optionally substituted with one or more groups chosen from a hydrogen atom, a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, aryl, aryl-C1-C6-alkylene, oxo or thio group;
- the nitrogen atom(s) of A being optionally substituted with R6 when the nitrogen is adjacent to a carbon atom substituted with an oxo group, or with R7 in the other cases;
- n is equal to 1, 2 or 3;
- Y represents a heteroaryl optionally substituted with one or more groups chosen from a halogen atom and a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, hydroxyl, C1-C6-alkoxy, C1-C6-fluoroalkoxy, cyano, C(O)NR1R2, nitro, NR1R2, C1-C6-thioalkyl, SH, —S(O)—C1-C6-alkyl, —S(O)2—C1-C6-alkyl, SO2NR1R2, NR3COR4, NR3SO2R5, aryl-C1-C6-alkylene or aryl group, the aryl and the aryl-C1-C6-alkylene being optionally substituted with one or more substituents chosen from a halogen and a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C1-C6-fluoroalkoxy, nitro or cyano group;
- R1 and R2 represent, independently of each other, a hydrogen atom or a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, aryl-C1-C6-alkylene or aryl group;
- or R1 and R2 together form, with the nitrogen atom that bears them, an azetidinyl, pyrrolidinyl, piperidyl, azepinyl, morpholinyl, thiomorpholinyl, piperazinyl or homopiperazinyl group, this group being optionally substituted with a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, aryl-C1-C6-alkylene or aryl group;
- R3 and R4 represent, independently of each other, a hydrogen atom or a C1-C6-alkyl, aryl-C1-C6-alkylene or aryl group;
- R5 represents a C1-C6-alkyl, aryl-C1-C6-alkylene or aryl group;
- R6 represents a hydrogen atom or a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, aryl-C1-C6-alkylene or aryl group;
- R7 represents a hydrogen atom or a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, aryl-C1-C6-alkylene, C1-C6-alkyl-C(O)—, C3-C7-cycloalkyl-C1-C3-alkylene-(CO)—, C1-C6-fluoroalkyl-C(O)—, C3-C7-cycloalkyl-C(O)—, aryl-C(O)—, aryl-C1-C6-alkylene-C(O)—, C1-C6-alkyl-S(O)2—, C1-C6-fluoroalkyl-S(O)2—, C3-C7-cycloalkyl-S(O)2—, C3-C7-cycloalkyl-C1-C3-alkylene-S(O)2—, aryl-S(O)2—, aryl-C1-C6-alkylene-S(O)2— or aryl group;
- the sulfur atom(s) of the heterocycle A or of the heteroaryl Y optionally being in oxidized form;
- the nitrogen atom(s) of the heterocycle A or of the heteroaryl Y optionally being in oxidized form;
- or an acid-addition salt thereof.
16 more elements
Dependencies are inferred from the claim text.