3-Acylindole derivatives, preparation and therapeutic use thereof

1. A compound of the formula (I):

wherein:

X represents an oxygen atom;

R 1 represents a —N(R 7 )SO 2 R 8 ;

R 2 represents a hydrogen atom or a (C 1 -C 4 )alkyl;

R 3 represents:

a (C 1 -C 6 )alkyl which is unsubstituted or substituted by:

a naphthyl which is unsubstituted or substituted one or more times by substituents chosen independently from a halogen atom, a (C 1 -C 4 )alkyl, a (C 1 -C 4 )alkoxy or a trifluoromethyl radical;

R 4 and R 5 each independently represent a hydrogen atom, a halogen atom, a (C 1 -C 4 )alkyl, a (C 1 -C 4 )alkoxy, a trifluoromethyl radical or a nitro;

R 7 represents a hydrogen atom or a (C 1 -C 4 )alkyl; and

R 8 represents a (C 1 -C 4 )alkyl or a trifluoromethyl radical; or

a salt thereof.

2. The compound of formula (I) according to claim 1 , wherein:

X represents an oxygen atom;

R 1 represents a group chosen from —NHSO 2 CH 3 ,or —NHSO 2 CF 3 ;

R 2 represents a hydrogen atom, a methyl or an ethyl;

R 3 represents:

a tert-butyl, an isobutyl, a 2,2-dimethylpropyl, or a naphthylmethyl,

R 4 represents a hydrogen atom or is in the 6-position of the indole and represents a chlorine atom or a methyl; and

R 5 represents a hydrogen atom or is in the 7-position of the indole and represents a bromine, chlorine or fluorine atom, a methoxy or a nitro.

3. The compound of formula (I) according to claim 1 , wherein:

X represents an oxygen atom;

R 1 represents a group chosen from —NHSO 2 CH 3 , or —NHSO 2 CF 3 ;

R 2 represents a methyl or an ethyl;

R 4 represents a hydrogen atom or is in the 6-position of the indole and represents a chlorine atom or a methyl; and

R 5 represents a hydrogen or is in the 7-position of the indole and represents a bromine, chlorine or fluorine atom, a methoxy or a nitro.

4. The compound of formula (I) according to claim 1 , wherein:

X represents an oxygen atom;

R 1 represents a group chosen from —NHSO 2 CH 3 , or —NHSO 2 CF 3 ;

R 2 represents a methyl;

R 4 represents a hydrogen atom or is in the 6-position of the indole and represents a chlorine atom or a methyl; and

R 5 represents a hydrogen or is in the 7-position of the indole and represents a bromine, chlorine or fluorine atom, a methoxy or a nitro.

5. The compound of formula (I) according to claim 1 chosen from:

—N-[3-[7-bromo-3-(3,3-dimethylbutanoyl)-2-methyl-1H-indol-1-yl]propyl]methanesulfonamide;

—N-[3-[7-chloro-3-(3,3-dimethylbutanoyl)-2-methyl-1H-indol-1-yl]propyl]methanesulfonamide; and

—N-[3-[7-bromo-3-(3,3-dimethylbutanoyl)-2,6-dimethyl-1H-indol-1-yl]propyl]methanesulfonamide;

or a salt thereof.

6. A process for the preparation of a compound of formula (I) according to claim 1 in which X represents an oxygen atom, comprising:

reacting a compound of formula (II):

in which R 1 , R 2 , R 4 and R 5 are as defined in claim 1 , in the presence of a Lewis acid, with an acid halide of formula (III):

in which R 3 is as defined in claim 1 and Hal represents a halogen atom.

7. A pharmaceutical composition comprising a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof in combination with at least one pharmaceutically acceptable excipient.

8. A pharmaceutical composition comprising a compound of formula (I) according to claim 2 or a pharmaceutically acceptable salt thereof in combination with at least one pharmaceutically acceptable excipient.

9. A pharmaceutical composition comprising a compound of formula (I) according to claim 3 or a pharmaceutically acceptable salt thereof in combination with at least one pharmaceutically acceptable excipient.

10. A pharmaceutical composition comprising a compound of formula (I) according to claim 4 or a pharmaceutically acceptable salt thereof in combination with at least one pharmaceutically acceptable excipient.

11. A pharmaceutical composition comprising a compound of formula (I) according to claim 5 or a pharmaceutically acceptable salt thereof in combination with at least one pharmaceutically acceptable excipient.