N-(Aminoheteroaryl)-1H-indole-2-carboxamide derivatives, and preparation and therapeutic application thereof

A compound of formula (I):

• in which
• X1 is hydrogen, halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, cyano, C(O)NR1R2, nitro, C1-C6-thioalkyl, —S(O)—C1-C6-alkyl, —S(O)2—C1-C6-alkyl, SO2NR1R2, aryl-C1-C6-alkylene, aryl or heteroaryl group, the aryl and heteroaryl being optionally substituted with one or more substituents selected from halogen, 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;
• X2 is hydrogen, halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, C1-C6-fluoroalkoxyl, cyano, C(O)NR1R2, C1-C6-thioalkyl, —S(O)—C1-C6-alkyl, —S(O)2—C1-C6-alkyl, SO2NR1R2, aryl-C1-C6-alkylene, aryl or heteroaryl group, the aryl and the heteroaryl being optionally substituted with one or more substituents selected from halogen, 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;
• X3 and X4, independently of one another, are hydrogen, halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, 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, aryl-C1-C6-alkylene, aryl or heteroaryl group, the aryl and the heteroaryl being optionally substituted with one or more substituents selected from halogen, 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;
• Z1, Z2, Z3 and Z4, independently of one another, are nitrogen or C(R6) group, wherein at least one of which is nitrogen and at least one of which is C(R6) group;
• the nitrogen atom or one of the nitrogen atoms present in the ring, defined as nitrogen in the 1-position, being optionally substituted with R7 when the carbon atom in the 2- or 4-position with respect to this reference nitrogen is substituted with an oxo or thio group;
• n is equal to 0, 1, 2 or 3;
• Y is aryl or heteroaryl optionally substituted with one or more groups selected from halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, hydroxy, C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, C1-C6-fluoroalkoxyl, cyano, C(O)NR1R2, nitro, NR1R2, C1-C6-thioalkyl, thiol, —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 selected from halogen, 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;
• Z is a cyclic amine attached via the nitrogen atom, of formula:
• in which A is C1-C7-alkylene optionally substituted with one or two groups R8;
• B is C1-C7-alkylene group optionally substituted with one or two groups R9;
• L is a bond, sulfur, oxygen, NR10 or NR11,
• the carbon atoms of the cyclic amine Z being optionally substituted with one or more groups R12 which may be identical to or different from one another;
• R1 and R2, independently of one another, are hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, aryl-C1-C6-alkylene, aryl or heteroaryl group;
• or
• R1 and R2 taken together with the nitrogen atom to which they are attached form azetidinyl, pyrrolidinyl, piperidinyl, azepinyl, morpholinyl, thiomorpholinyl, piperazinyl or homopiperazinyl group, this group being optionally substituted with C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, aryl-C1-C6-alkylene, aryl or heteroaryl group;
• R3 and R4, independently of one another, are hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, aryl-C1-C6-alkylene, aryl or heteroaryl group;
• R5 is a C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, aryl-C1-C6-alkylene, aryl or heteroaryl group;
• R6 is hydrogen, halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, C1-C6-fluoroalkoxy, C1-C6-thioalkyl, —S(O)—C1-C6-alkyl, —S(O)2—C1-C6-alkyl, aryl, aryl-C1-C6-alkylene, heteroaryl, hydroxy, thiol, oxo or thio group;
• R7 is hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, C1-C6-fluoroalkoxy, aryl, aryl-C1-C6-alkylene or heteroaryl group;
• R8, R9 and R10 are defined such that:
• two groups R8 can together form a bond or a C1-C6-alkylene group;
• two groups R9 can together form a bond or a C1-C6-alkylene group;
• R8 and R9 can together form a bond or a C1-C6-alkylene group;
• R8 and R10 can together form a bond or a C1-C6-alkylene group;
• R9 and R10 can together form a bond or a C1-C6-alkylene group;
• R11 is hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, C1-C6-fluoroalkoxy, hydroxy, COOR5, C(O)NR1R2, aryl-C1-C6-alkylene, aryl or heteroaryl group, the aryl and the heteroaryl being optionally substituted with one or more substituents selected from halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C3-C7-cycloalkoxy, C1-C6-fluoroalkoxy, nitro or cyano group;
• R12 is fluorine, C1-C6-alkyl optionally substituted with R13, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl or C1-C6-cycloalkyl-1,1-idinyl group, a C3-C7-heterocycloalkyl-1,1-idinyl group optionally substituted on a nitrogen atom with a group R11, or a C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, C1-C6-fluoroalkoxy, C(O)NR1R2, NR1R2, NR3COR4, OC(O)NR1R2, NR3COOR5, NR3CONR1R2, hydroxy, thiol, oxo, thio, aryl-C1-C6-alkylene or aryl group, the aryl being optionally substituted with one or more substituents selected from halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkylene, C1-C6-fluoroalkyl, C1-C6-alkoxy, C3-C7-cycloalkoxy, C1-C6-fluoroalkoxy, nitro or cyano group;
• R13 is a C1-C6-alkoxy, C3-C7-cycloalkoxy, C3-C7-cycloalkyl-C1-C6-alkylene-O—, C(O)NR1R2, NR1R2, NR3COR4, OC(O)NR1R2, NR3COOR5 or hydroxy;
• and
• it being possible for the nitrogen atom(s) of the compound of formula (I) to be in oxidized form;
• it being possible for the sulfur atom(s) of the compound of formula (I) to be in oxidized form;
• or an addition salt thereof, or a hydrate or a solvate thereof.