Pyrrole derivatives, preparation of same and therapeutic application thereof

1. A compound of Formula (I):

in which:

R 1 represents a hydrogen atom or a (C 1 -C 4 )alkyl group which is unsubstituted or substituted with one or more fluorine atoms;

R 2 represents:

either a homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical, said radicals being unsubstituted or substituted once or twice with a substituent, each chosen independently from a fluorine atom, a (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxyl, trifluoromethyl, —OCF 3 , CH 2 OH, —CONH 2 or a phenyl group, said phenyl group being unsubstituted or substituted once or twice with a substituent, each chosen independently from a halogen atom, a —CF 3 group, a methoxyl group or a trifluoromethoxyl group;

or an amino(C 1 -C 6 )alkyl group which is unsubstituted or substituted with one or more substituents, each chosen independently from a fluorine atom, a hydroxyl group, a —CONH 2 group or a phenyl group, said phenyl group being unsubstituted or substituted once or twice with a substituent, each chosen independently from a halogen atom, a —CF 3 group, a methoxyl group or a trifluoromethoxyl group;

or R 1 and R 2 , together with the nitrogen atom to which they are attached, constitute:

either a piperazin-1-yl or 1,4-diazepan-1-yl radical, said radicals being unsubstituted or substituted with a substituent chosen from a phenyl, benzodioxolyl, benzodioxolylmethyl, tetrahydrofuranylcarbonyl, —COR 11 , or —CH 2 COR 11 group, the phenyl group itself being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, or a (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxyl or cyano group;

or a homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical, said radicals being unsubstituted or substituted once or twice with a substituent, each independently chosen from:

a fluorine atom, or a cyano, —COR 11 , —NR 12 R 13 , —NHCOR 14 , —CH 2 COR 11 , —SO 2 R 14 , or —SO 2 NR 12 R 13 group;

or a phenyl group or a pyridinyl group; said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, or a (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxyl or cyano group;

or a benzyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, or a (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxyl or cyano group;

or a piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl group, said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a fluorine atom, or a (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxyl, hydroxyl, trifluoromethyl or OCF 3 group;

or an aminophenyl or aminobenzyl group, said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, or a (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxyl or cyano group;

or an amino(C 1 -C 6 )alkyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or an amino(C 3 -C 7 )cycloalkyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a hydroxyl group, a (C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxyl group or a cyano group, said (C 1 -C 4 )alkyl group being unsubstituted or substituted one or more times with a fluorine atom;

R 3 , R 4 , R 5 , R 6 , R 7 , R 8 each independently represent a hydrogen atom, a halogen atom, a —CN, —S(O) n R 14 or —OSO 2 R 14 group, or a (C 1 -C 6 )alkyl group which is unsubstituted or substituted one or more times with a fluorine atom or a (C 1 -C 6 )alkoxyl group which is unsubstituted or substituted with one or more fluorine atoms, on the condition that one of the two substituents R 3 and R 6 represents a Y-A-R 9 group;

Y represents an oxygen atom;

A represents a (C 1 -C 4 ) alkylene group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a (C 1 -C 3 )alkyl group or with a fluorine atom;

R 9 represents an —OR 12 , —CN, —CO 2 H, NR 12 R 13 , —CONR 12 R 13 , —NR 15 COR 12 , —CONHNH 2 , —CONHOH, —CONHSO 2 R 14 , —S(O) 9 R 14 , —SO 2 NR 12 R 13 , —NR 18 SO 2 R 14 or —NR 15 SO 2 NR 12 R 13 ;

R 10 represents a hydrogen or a (C 1 -C 4 )alkyl group;

R 11 represents:

a (C 1 -C 4 )alkyl, phenyl, benzyl, (C 1 -C 4 )alkoxyl or (C 1 -C 3 )alkylene-O—(C 1 -C 3 )alkyl group, said groups being unsubstituted or substituted with one or more substituents, each chosen independently from a (C 1 -C 4 )alkoxyl group, a hydroxyl group or a fluorine atom;

a trifluoromethyl;

or an —NR 16 R 17 group;

R 12 and R 13 each independently represent a hydrogen atom or a (C 1 -C 6 )alkyl group optionally substituted with one or more substituents, each chosen independently from a fluorine atom, —OH or —OR 14 ,

or R 12 and R 13 , together with the nitrogen atom to which they are attached, constitute a 4- to 7-membered heterocyclic radical which may comprise a second heteroatom chosen from a nitrogen, oxygen or sulphur atom;

n represents 0, 1 or 2;

R 14 represents a (C 1 -C 4 )alkyl group which is unsubstituted or substituted with one or more fluorine atoms;

R 15 represents a hydrogen atom or a (C 1 -C 4 )alkyl group;

R 16 and R 17 each independently represent:

a hydrogen atom;

or a benzyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, or a (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxyl or cyano group;

or a (C 1 -C 6 )alkyl group optionally substituted with one or more substituents, each chosen independently from a halogen atom, —OH or —OR 14 ;

R 18 represents a hydrogen atom or a (C 1 -C 4 )alkyl group which is unsubstituted or substituted with one or more fluorine atoms;

Alk represents a (C 1 -C 4 )alkyl group;

or the salt thereof.

2. The compound according claim 1 , characterized in that the substituent R 6 represents a Y-A-R 9 group and the substituent R 3 represents a hydrogen atom, a halogen atom, a —CN, —S(O) 6 R 14 or —OSO 2 R 14 group, a (C 1 -C 6 )alkyl group which is unsubstituted or substituted one or more times with a fluorine atom, or a (C 1 -C 6 )alkoxyl group which is unsubstituted or substituted with one or more fluorine atoms, or the salt thereof.

3. The compound according to claim 1 , characterized in that the substituent R 3 represents a Y-A-R 9 group and a substituent R 6 represents a hydrogen atom, a halogen atom, a —CN, —S(O) n R 14 or —OSO 2 R 14 group, a (C 1 -C 6 )alkyl group which is unsubstituted or substituted one or more times with a fluorine atom, or a (C 1 -C 6 )alkoxyl group which is unsubstituted or substituted with one or more fluorine atoms, or the salt thereof.

4. The compound according to claim 1 , characterized in that A represents an unsubstituted (C 1 -C 4 ) alkylene group, or the salt thereof.

5. The compound according to claim 1 , characterized in that:

R 1 represents a hydrogen atom or a (C 1 -C 4 )alkyl group which is unsubstituted or substituted with one or more fluorine atoms;

R 2 represents:

either a homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical, said radicals being substituted once or twice with a substituent, each chosen independently from a fluorine atom, a (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxyl, trifluoromethyl, —OCF 3 , —CH 2 OH or —CONH 2 group or a phenyl group, said phenyl group being unsubstituted or substituted once or twice with a substituent, each chosen independently from a halogen atom, a —CF 3 group, a methoxyl group or a trifluoromethoxyl group;

or an amino(C 1 -C 6 )alkyl group substituted with one or more substituents, each chosen independently from a fluorine atom, a hydroxyl group, a —CONH 2 group or a phenyl group, said phenyl group being unsubstituted or substituted once or twice with a substituent, each independently chosen from a halogen atom, a —CF 3 group, a methoxyl group or a trifluoromethoxyl group;

and the salt thereof.

6. The compound according to claim 5 , characterized in that R 2 radical represents in particular a homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical, said radicals being substituted once or twice with a substituent, each chosen independently from a fluorine atom, a (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxyl, trifluoromethyl, —OCF 3 , —CH 2 OH or —CONH 2 group or a phenyl group, said phenyl group being unsubstituted or substituted once or twice with a substituent, each chosen independently from a halogen atom, a —CF 3 group, a methoxyl group or a trifluoromethoxyl group;

or the salt thereof.

7. The compound according to claim 1 , characterized in that:

R 1 and R 2 , together with the nitrogen atom to which they are linked, constitute:

either a piperazin-1-yl or 1,4-diazepan-1-yl radical, said radicals being substituted with a substituent chosen from a phenyl, benzodioxolyl, benzodioxolylmethyl, tetrahydrofuranylcarbonyl, —COR 11 or —CH 2 COR 11 group, the phenyl group itself being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a (C 1 -C 4 )alkyl group, a trifluoromethyl group, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or a homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical, said radicals being substituted once or twice with a substituent, each chosen independently from:

a fluorine atom, or a cyano, —COR 11 , —NR 12 R 13 , —NHCOR 14 , —CH 2 COR 11 , —SO 2 NR 14 or —SO 2 NR 12 R 13 group;

or a phenyl or pyridinyl group; said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a (C 1 -C 4 )alkyl group, a trifluoromethyl group, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or a benzyl group substituted one or more times with a substituent, each chosen independently from a halogen atom, a (C 1 -C 4 )alkyl group, a trifluoromethyl group, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or a piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl group, said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a fluorine atom, a (C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxyl group, a hydroxyl group, a trifluoromethyl group or an OCF 3 group;

or an aminophenyl or aminobenzyl group, said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a (C 1 -C 4 )alkyl group, a trifluoromethyl group, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or an amino (C 1 -C 6 )alkyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or an amino (C 3 -C 7 )cycloalkyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a hydroxyl group, a (C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxyl group or a cyano group, said (C 1 -C 4 )alkyl group being unsubstituted or substituted one or more times with a fluorine atom;

or the salt thereof.

8. The compound according to claim 7 , characterized in that:

R 1 and R 2 , together with the nitrogen atom to which they are attached, constitute a homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical, said radicals being substituted once or twice with a substituent, each chosen independently from:

a fluorine atom, or a cyano, —COR 11 , —NR 12 R 13 , —NHCOR 14 , —CH 2 COR 11 , —SO 2 R 14 or —SO 2 NR 12 R 13 group;

or a phenyl or pyridinyl group; said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a (C 1 -C 4 )alkyl group, a trifluoromethyl group, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or a benzyl group substituted one or more times with a substituent, each chosen independently from a halogen atom, a (C 1 -C 4 )alkyl group, a trifluoromethyl group, a hydroxyl group, a (C 1 -C 4 )alkoxyl group and a cyano group;

or a piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl group, said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a fluorine atom, a (C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxyl group, a hydroxyl group, a trifluoromethyl group or an —OCF 3 group;

or an aminophenyl or aminobenzyl group, said groups being unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a (C 1 -C 4 )alkyl group, a trifluoromethyl group, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or an amino(C 1 -C 6 )alkyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a hydroxyl group, a (C 1 -C 4 )alkoxyl group or a cyano group;

or an amino (C 3 -C 7 )cycloalkyl group which is unsubstituted or substituted one or more times with a substituent, each chosen independently from a halogen atom, a hydroxyl group, a (C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxyl group or a cyano group, said (C 1 -C 4 )alkyl group being unsubstituted or substituted one or more times with a fluorine atom;

or the salt thereof.

9. The compound according to claim 1 , characterized in that the compound is chosen from the group consisting of:

1-[4-(2,4-dichlorophenyl)-5-[4-(4-hydroxypropoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonyl]-4-(3-fluorobenzylamino)piperidine-4-carboxamide,

1-[5-(4-carbamoylmethoxy)phenyl-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carbonyl]-4-phenylpiperidine-4-carboxamide, and

1-[4-(2-chlorophenyl)-5-[4-(4-hydroxypropoxy)phenyl]-1-methyl-1H-pyrrole-2-carbonyl]-4-(4-fluoro-benzylamino)piperidine-4-carboxamide,

or the salts thereof.

10. A pharmaceutical composition, characterized in that it comprises a compound of Formula (I) according to claim 1 , or the pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.