Derivatives of n-(arylsulfonyl)beta-aminoacids comprising a substituted aminomethyl group, the preparation method thereof and the pharmaceutical compositions containing same

1. A compound of formula:

in which:

R 1 represents a phenylvinyl group; a phenyl group which is unsubstituted or substituted one or more times with R 6 , which may be identical or different; a naphthyl group which is unsubstituted or substituted one or more times with R 6 , which may be identical or different; a tetrahydronaphthyl group; a naphtho[2,3-d][1,3]dioxol-6-yl group; a heterocyclic radical chosen from quinolyl, isoquinolyl, 1-benzofur-2-yl, 2,1,3-benzoxadiazol-4-yl, 2,1,3-benzothiadiazol-4-yl, 1,3-benzothiazol-2-yl, 1-benzothiophen-2-yl, 1H-pyrazol-4-yl, thien-2-yl, 5-isoxazothien-2-yl, benzothien-2-yl, thieno[3,2-c]pyrid-2-yl; the said heterocyclic radicals being unsubstituted or substituted one or more times with R 6 , which may be identical or different;

R 2 represents hydrogen or a (C 1 –C 4 )alkyl group and R 3 represents a phenyl group which is unsubstituted or substituted one or more times with R 7 , which may be identical or different; a heterocyclic radical chosen from benzo[1,3]dioxol-5-yl, 2,1,3-benzothiadiazol-5-yl, 2,1,3-benzoxadiazol-5-yl, benzothiophen-5-yl, 2,3-dihydrobenzo[1,4]dioxin-6-yl, benzofuryl, dihydrobenzofuryl, 1,3-thiazol-2-yl, furyl and thienyl, the said heterocyclic radical being an substituted or substituted one or more times with a halogen atom or with a (C 1 –C 4 )alkyl group;

or alternatively R 2 represents a phenyl group which is unsubstituted or substituted one or more times with R 6 , which may be identical or different; a heterocyclic radical chosen from benzo[1,3]diaxol-5-yl, pyridyl and indanyl, and R 3 represents hydrogen;

R 4 represents a group —CONR 8 R 9 ; a group —CSNR 8 R 9 ; a group —COR 13 ; a phenyl group which is unsubstituted or substituted one or more times with R 10 ; a heterocyclic radical chosen from pyridyl, imidazolyl, furyl, benzimidazolyl, benzothiazol-2-yl and benzo[1,3]dioxol-5-yl, the said radicals being unsubstituted or substituted with one or more methyl groups or halogen atoms;

R 5 represents a group —CH 2 NR 11 R 12 or —CH 2 N(O)R 11 R 12 ;

R 6 represents a halogen atom; a (C 1 –C 4 )alkyl group; a trifluoromethyl group; a (C 1 –C 4 )alkoxy group; a 2-fluoroethoxy group; a trifluoromethoxy, methylenedioxy or difluoromethylenedioxy group;

R 7 represents a halogen atom; a (C 1 –C 4 )alkyl group; a phenyl group; a trifluoromethyl group; a (C 1 –C 4 )alkoxy group; a benzyloxy group; a trifluoromethoxy group;

R 8 and R 9 each independently represent hydrogen; a (C 1 –C 4 alkyl group; a (C 3 –C 7 )cycloalkyl group; a (C 3 –C 7 )cycloalkyl(C 1 –C 4 )alkyl group; an ω-(C 1 –C 4 )dialkylamino(C 2 –C 4 )alkyl group;

or alternatively R 8 and R 9 , together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from pyrrolidinyl, morpholin-4-yl, thiomorpholin-4-yl, azepin-1-yl, piperidyl which is unsubstituted or substituted with one or more halogen atoms or one or more (C 1 –C 4 )alkyl or (C 1 –C 4 )alkoxy or trifluoromethyl groups, 3,4-dihydropiperid-1-yl, cyclohexyl-spiro-4-piperid-1-yl, and piperazinyl which is unsubstituted or substituted with one or more (C 1 –C 4 )alkyl groups;

R 10 represents a halogen atom; a (C 1 –C 4 )alkyl group; a hydroxy group; a (C 1 –C 6 )alkoxy group; R 10 can also represent a group —CH 2 NR 11 R 12 when R 5 represents a group —CH 2 NR 11 R 12 , the said groups then being identical;

R 11 and R 12 each independently represent hydrogen; a (C 1 –C 6 )alkyl group; a (C 2 –C 4 )alkenyl group; a (C 3 –C 7 )cycloalkyl group; a (C 3 –C 7 )cycloalkyl(C 1 –C 4 )alkyl group; an ω-hydroxy(C 2 –C 4 )alkylene group; an ω-methoxy(C 2 –C 4 )alkylene group; an ω-trifluoromethyl(C 2 –C 4 )alkylene group; an ω-halo(C 2 –C 4 )alkylene group,

or alternatively R 11 and R 12 , together with the nitrogen atom to which they are attached, constitute a monocyclic, bicyclic or heterocyclic radical chosen from azetidinyl, pyrrolidinyl, morpholin-4-yl, thiomorpholin-4-yl, piperid-1-yl, piperazin-1-yl, 1,2,3,6-tetrahydropyrid-1-yl, 2,3,4,5-tetrahydropyridinium, decahydroquinolyl, decahydroisoquinolyl, tetrahydroisoquinolyl, octahydro-1H-isoindolyl, (C 4 –C 6 )cycloalkyl-spiro-piperidyl, 3-azabicyclo[3.1.0]hexyl and 7-azabicyclo[2.2.1]heptan-7-yl, which may be unsubstituted or substituted one or more times with a halogen atom or a (C 1 –C 4 )alkyl, hydroxyl, (C 1 –C 4 )alkoxy, trifluoromethyl, difluoromethylene or phenyl group;

R 13 represents a phenyl, thiazol-2-yl or pyridyl group;

or a salt thereof with a mineral or organic acid, or a solvate or hydrate of said compound or said salt.

2. The compound according to claim 1 of formula:

in which:

R 1 represents a phenylvinyl group; a phenyl group which is unsubstituted or substituted one or more times with R 6 , which may be identical or different; a naphthyl group which is unsubstituted or substituted one or more times with R 6 , which may be identical or different; a tetrahydronaphthyl group; a heterocyclic radical chosen from quinolyl, 1-benzofur-2-yl, 2,1,3-benzoxadiazol-4-yl, 2,1,3-benzothiadiazol-4-yl, 1,3-benzothiazol-2-yl, 1-benzothiophen-2-yl, 1H-pyrazol-4-yl, thien-2-yl, 5-isoxazolethien-2-yl, benzothien-2-yl, thieno[3,2-c]pyrid-2-yl; naphtho[2,3-d][1,3]dioxol-6-yl; the said heterocyclic radicals being unsubstituted or substituted one or more times with R 6 , which may be identical or different;

R 2 represents hydrogen or a (C 1 –C 4 )alkyl group and R 3 represents a phenyl group which is unsubstituted or substituted one or more times with R 7 , which may be identical or different; a heterocyclic radical chosen from benzo[1,3]dioxol-5-yl which is unsubstituted or substituted in the −2 position with two fluorine atoms; 2,1,3-benzothiadiazol-5-yl; 2,3-dihydrobenzo[1,4]dioxin-6-yl; 1,3-thiazol-2-yl; 1-benzofur-2-yl; 1-benzofur-5-yl; furyl; thien-2-yl; thien-3-yl;

or R 2 represents a phenyl group which is unsubstituted or substituted one or more times with R 6 , which may be identical or different; a heterocyclic radical chosen from benzo[1,3]dioxol-5-yl; pyridyl; indanyl; and R 3 represents hydrogen;

R 4 represents a group —CONR 8 R 9 ; a phenyl group which is unsubstituted or substituted one or more times with R 10 ; a heterocyclic radical chosen from pyridyl, imidazolyl, furyl, benzimidazolyl, benzothiazol-2-yl and benzo[1,3]dioxol-5-yl, the said radicals being unsubstituted or substituted with a methyl;

R 5 represents a group —CH 2 NR 11 R 12 ;

R 6 represents a halogen atom; a (C 1 –C 4 )alkyl group; a trifluoromethyl group; a (C 1 –C 4 )alkoxy group; a 2-fluoroethoxy group; a trifluoromethoxy, methylenedioxy or difluoromethylenedioxy group;

R 7 represents a halogen atom; a (C 1 –C 4 )alkyl group; a trifluoromethyl group; a (C 1 –C 4 )alkoxy group; a benzyloxy group; a trifluoromethoxy group;

R 8 and R 9 each independently represent hydrogen; a (C 1 –C 4 )alkyl group; a (C 3 –C 7 )cycloalkyl group; a (C 3 –C 7 )cycloalkyl(C 1 –C 4 )alkyl group; an ω-(C 1 –C 4 )dialkylamino(C 2 –C 4 )alkyl group;

or R 8 and R 9 , together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from pyrrolidinyl, piperidyl, morpholin-4-yl, thiomorpholin-4-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, 4-methylpiperid-1-yl, 2-methylpiperid-1-yl, 4,4-dimethylpiperid-1-yl, 4,4-difluoropiperid-1-yl, 4-trifluoromethylpiperid-1-yl, 3,4-dihydropiperid-1-yl, azepin-1-yl and cyclohexyl-spiro-4-piperid-1-yl;

R 10 represents a halogen atom; a (C 1 –C 4 )alkyl group; a hydroxyl group; a (C 1 –C 6 alkoxy group; R 10 can also represent a group —CH 2 NR 11 R 12 when R 5 represents a group —CH 2 NR 11 R 12 , the said groups then being identical;

R 11 and R 12 each independently represent hydrogen; a (C 1 –C 6 )alkyl group; a (C 2 –C 4 alkenyl group; a (C 3 –C 7 )cycloalkyl group; a (C 3 –C 7 )cycloalkyl(C 1 –C 4 )alkyl group; an ω-hydroxy(C 2 –C 4 )alkylene group; an ω-methoxy(C 2 –C 4 )alkylene group; an ω-trifluoromethyl(C 2 –C 4 )alkylene group; an ω-halo(C 2 –C 4 )alkylene group;

or R 11 and R 12 , together with the nitrogen atom to which they are attached, constitute a monocyclic, bicyclic or heterocyclic radical chosen from azetidinyl, pyrrolidinyl, morpholin-4-yl, thiomorpholin-4-yl, piperid-1-yl, piperazin-1-yl, 1,2,3,6-tetrahydropyrid-1-yl, decahydroquinolyl, decahydroisoquinolyl, octahydro-1H-isoindolyl, (C 4 –C 6 )cycloalkyl-spiro-piperidyl and 3-azabicyclo[3.1.0]hexyl, which may be unsubstituted or substituted one or more times with a halogen atom or a (C 1 –C 4 )alkyl, hydroxyl, (C 1 –C 4 )alkoxy, trifluoromethyl, difluoromethylene or phenyl group;

or a salt thereof with a mineral or organic acid, or a solvate or hydrate of said compound or said salt.

3. The compound of formula (I) according to claim 1 in which R 1 represents a 2,4-dichloro-3-methylphenyl, naphthyl, 6-methoxynaphth-2-yl, 3-methylbenzothiophen-2-yl, 3-methyl-5-chlorobenzothiophen-2-yl, 3-methyl-5-methoxybenzothiophen-2-yl, 3-methyl-6-methoxybenzothiophen-2-yl or 3-methyl-1-benzofur-2-yl group.

4. The compound of formula (I) according to claim 1 in which R 2 represents hydrogen and R 3 represents a benzo[1,3]dioxol-5-yl or phenyl group which is unsubstituted or substituted with a halogen.

5. The compound of formula (I) according to claim 1 in which R 4 represents a group —CONR 8 R 9 and —NR 8 R 9 represents a di(C 1 –C 4 )alkylamino radical, a pyrrolidinyl or piperidyl group which is unsubstituted or substituted one or two times with a methyl or a halogen.

6. The compound of formula (I) according to claim 1 in which R 5 represents a group —CH 2 NR 11 R 12 in which —NR 11 R 12 represents an ethylisobutylamino, ethylisopropylamino, ethyl-tert-butylamino, diisopropylamino, cyclopentylmethylamino or cyclopentylethylamino radical or a piperidyl radical which is unsubstituted or substituted one or more times with a methyl or a halogen.

7. The compound according to claim 1 of formula:

in which:

R 1 represents a 2,4-dichloro-3-methylphenyl, naphthyl, 6-methoxynaphth-2-yl, 3-methylbenzothiophen-2-yl, 3-methyl-5-chlorobenzothiophen-2-yl, 3-methyl-5-methoxybenzothiophen-2-yl, 3-methyl-6-methoxybenzothiophen-2-yl or 3-methyl-1-benzofur-2-yl group;

R 3 represents a benzo[1,3]dioxol-5-yl or phenyl group which is unsubstituted or substituted with a halogen;

R 8 and R 9 , together with the nitrogen atom to which they are attached, constitute a di(C 1 –C 4 )alkylamino, pyrrolidinyl or piperidyl radical which is unsubstituted or substituted one or two times with a methyl or a halogen;

R 11 and R 12 , together with the nitrogen atom to which they are attached, constitute an ethylisobutylamino, ethylisopropylamino, ethyl-tert-butylamino, diisopropylamino, cyclopentylmethylamino or cyclopentylethylamino radical or a piperidyl radical which is unsubstituted or substituted one or more times with a methyl or a halogen;

or a salt thereof with a mineral or organic acid, or a solvate or hydrate of said compound or said salt.

8. The compound according to claim 1 , chosen from:

(R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-(((6-methoxy-2-naphthyl)sulphonyl)amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-((2-naphthylsulphonyl)amino)propanoyl)amino)-3-(4-((cyclopentyl(ethyl)amino)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-2-((3-(((6-methoxy-2-naphthyl)sulphonyl)amino)-3-phenylpropanoyl)amino)-N-isopropyl-N-methyl propanamide;

(R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-(((6-methoxy-2-naphthyl)sulphonyl)amino)propanoyl)amino)-3-(4-((tert-butyl(ethyl)amino)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-(((3-methyl-1-benzothiophen-2-yl)sulphonyl)amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-2-((3-(((5-methoxy-3-methyl-1-benzothiophen-2-yl)sulphonyl)amino)-3-phenylpropanoyl)amino)-N-isopropyl-N-methylpropanamide;

(R,R) N-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)benzyl)-3-(((6-methoxy-2-naphthyl)sulphonyl)amino)-3-phenyl-N-(1-piperidylcarbonyl)propanamide;

(R,R) 2-((3-(4-chlorophenyl)-3-(((6-methoxy-2-naphthyl)sulphonyl)amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-2-((3-(((6-methoxy-2-naphthyl)sulphonyl)amino)-3-phenylpropanoyl)amino)-N,N-diethylpropanamide;

(R,R) 2-((3-(3-fluorophenyl)-3-(((6-methoxy-2-naphthyl)sulphonyl)amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-(((3-methyl-1-benzofur-2-yl)sulphonyl)amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-((2-naphthylsulphonyl)amino)propanoyl)amino)-3-(3-((tert-butyl(ethyl)amino)methyl)phenyl)-N-isopropyl-N-methylpropanamide;

(R,R) 3-(4-(7-azabicyclo[2.2.1]hept-7-ylmethyl)phenyl)-2-((3-(1,3-benzodioxol-5-yl)-3-(((6-methoxynaphthyl)sulphonyl)amino)propanoyl)amino)-N-isopropyl-N-methyl propanamide;

or a salt thereof, or a solvate or hydrate of said compound or said salt.

9. A process for preparing a compound of formula (I) according to claim 1 , or a salt thereof, or a solvate or hydrate of said compound or said salt, wherein:

an acid or a functional derivative of this acid of formula:

 in which R 2 and R 3 are as defined for a compound of formula (I) in claim 1 , X represents either hydrogen or a group R 1 SO 2 — in which R 1 is as defined for a compound of formula (I) in claim 1 , or an N-protecting group, is reacted with a compound of formula:

 in which Y represents either R 4 as defined for a compound of formula (I) in claim 1 , or a (C 1 –C 4 )alkoxycarbonyl, and Z represents either R 5 as defined for a compound of formula (I) in claim 1 , or a —CN group, on the condition that, when Y represents R 4 which represents a phenyl substituted with a group —CH 2 NR 11 R 12 , Z represents R 5 which represents a group —CH 2 NR 11 R 12 , R 11 and R 12 being as defined for a compound of formula (I) in claim 1 ; and

when X=R 1 SO 2 —, Y=R 4 and Z=R 5 , the expected compound of formula (I) is obtained;

or when X≠R 1 SO 2 and/or Y≠R 4 and/or Z≠R 5 , that is to say when at least one of the X, Y and Z groups represents, respectively, X=H or an N-protecting group, Y=(C 1 –C 4 )alkoxycarbonyl, Z=—CN, the compound thus obtained of formula:

 is subjected to one or more of the following steps:

when X represents an N-protecting group, this group is removed and the compound thus obtained of formula:

 is reacted with a sulphonyl halide of formula:

R 1 SO 2 -Hal  (VI)

 in which Hal represents a halogen;

when Y represents a (C 1 –C 4 )alkoxycarbonyl, it is hydrolyzed and the acid thus obtained or a functional derivative of this acid of formula:

 is reacted with a compound of formula:

HNR 8 R 9   (VIII);

 in which R 8 and R 9 are as defined for a compound of formula (I) from claim 1 ;

when Z represents a —CN group, this group is converted into R 5 .

10. A compound of formula:

in which:

X represents hydrogen or an N-protecting group;

R 3 represents a heterocyclic radical chosen from: (2,2-difluoro)benzo[1,3]dioxol-5-yl, 3-isopropylphenyl, 3-trifluoromethoxyphenyl, 2,1,3-benzoxadiazol-5-yl, benzothiophen-5-yl, 1-benzofur-6-yl, 1-benzofur-4-yl, 1-benzofur-3-methyl-5-yl, 2,3-dihydrobenzofur-4-yl;

or a salt thereof with a mineral or organic acid, in racemic form or in the form of a pure enantiomer.

11. A compound of formula:

in which:

R 1 represents a phenylvinyl; a heterocycle chosen from 1-benzofur-2-yl, 2,1,3-benzoxadiazol-4-yl, 2,1,3-benzothiadiazol-4-yl, 1,3-benzothiazol-2-yl, 1-benzothiophen-2-yl, 1H-pyrazol-4-yl, thien-2-yl, 5-isoxazolthien-2-yl, benzothien-2-yl, thieno[3,2-c]pyrid-2-yl and naphtho[2,3-d][1,3]dioxol-6-yl; the said heterocycles being unsubstituted or substituted one or more times with R 6 , which may be identical or different;

R 2 represents hydrogen or a (C 1 –C 4 )alkyl and R 3 represents a phenyl which is unsubstituted or substituted one or more times with R 7 , which may be identical or different; a heterocyclic radical chosen from benzo[1,3]dioxol-5-yl which is unsubstituted or substituted in position −2 with two fluorine atoms; 2,1,3-benzothiodiazol-5-yl; 2,1,3-benzoxadiazol-5-yl; benzothiophen-5-yl; 2,3-dihydrobenzo[1,4]dioxin-6-yl; 1-benzofur-2-yl; 1-benzofur-5-yl; 1-benzofur-6-yl; 1-benzofur-4-yl; 1-benzofur-3-methyl-5-yl; 2,3-dihydrobenzofur-4-yl; 1,3-thiazol-2-yl; furyl; thien-2-yl; thien-3-yl;

or R 2 represents a phenyl which is unsubstituted or substituted one or more times with R 6 , which may be identical or different; a benzo[1,3]dioxol-5-yl; a pyridyl; an indanyl; and R 3 represents hydrogen;

R 6 represents a halogen atom; a (C 1 –C 4 )alkyl group; a trifluoromethyl group; a (C 1 –C 4 )alkoxy group; a 2-fluoroethoxy group; a trifluoromethoxy, methylenedioxy or difluoromethylenedioxy group;

R 7 represents a halogen atom; a (C 1 –C 4 )alkyl group; a phenyl group; a trifluoromethyl group; a (C 1 –C 4 )alkoxy group; a benzyloxy group; a trifluoromethoxy group;

or a salt thereof with a mineral or organic acid, in racemic form or in the form of a pure enantiomer.

12. A compound of formula:

in which;

R 4 represents a group —CONR 8 R 9 ; a group —CSNR 8 R 9 ; a group —COR 13 ; a phenyl group which is unsubstituted or substituted one or more times with R 10 ; a heterocyclic radical chosen from pyridyl, imidazolyl, furyl, benzimidazolyl, benzothiazol-2-yl and benzo[1,3]dioxol-5-yl, the said radicals being unsubstituted or substituted with a methyl;

R 5 represents a group —CH 2 NR 11 R 12 or —CH 2 N(O)R 11 R 12 ;

R 8 and R 9 each independently represent hydrogen; a (C 1 –C 4 )alkyl group; a (C 3 –C 7 )cycloalkyl group; a (C 3 –C 7 )cycloalkyl(C 1 –C 4 )alkyl group; an ω-(C 1 –C 4 )dialkylamino(C 2 –C 4 )alkyl group;

or alternatively R 8 and R 9 , together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from pyrrolidinyl, piperidyl, morpholin-4-yl, thiomorpholin-4-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, 4-methylpiperid-1-yl, 2-methylpiperid-1-yl, 4,4-dimethylpiperid-1-yl, 4,4-difluoropiperid-1-yl, 4-trifluoromethylpiperid-1-yl, 4-methoxypiperid-1-yl, 3,4-dihydropiperid-1-yl, azepin-1-yl and cyclohexyl-spiro-4-piperid-1-yl;

R 10 represents a halogen atom; a (C 1 –C 4 )alkyl group; a hydroxy group; a (C 1 –C 6 )alkoxy group; R 10 can also represent a group —CH 2 NR 11 R 12 when R 5 represents a group —CH 2 NR 11 R 12 , the said groups then being identical;

R 11 and R 12 each independently represent hydrogen; a (C 1 –C 6 )alkyl group; a (C 2 –C 4 )alkenyl group; a (C 3 –C 7 )cycloalkyl group; a (C 3 –C 7 )cycloalkyl(C 1 –C 4 )alkyl group; an ω-hydroxy(C 2 –C 4 )alkylene group; an ω-methoxy(C 2 –C 4 )alkylene group; an ω-trifluoromethyl(C 2 –C 4 )alkylene group; an ω-halo(C 2 –C 4 )alkylene group;

or alternatively R 11 and R 12 , together with the nitrogen atom to which they are attached, constitute a monocyclic, bicyclic or heterocyclic radical chosen from azetidinyl, pyrrolidinyl, morpholin-4-yl, thiomorpholin-4-yl, piperid-1-yl, piperazin-1-yl, 1,2,3,6-tetrahydropyrid-1-yl, 2,3,4,5-tetrahydropyridinium, decahydroquinolyl, decahydroisoquinolyl, tetrahydroisoquinolyl, octahydro-1H-isoindolyl, (C 4 –C 6 )cycloalkyl-spiro-piperidyl, 3-azabicyclo[3.1.0]hexyl and 7-azabicyclo[2.2.1]heptan-7-yl, which may be unsubstituted or substituted one or more times with a halogen atom or a (C 1 –C 4 )alkyl, hydroxyl, (C 1 –C 4 )alkoxy, trifluoromethyl or difluoromethylene group;

R 13 represents a phenyl, thiazol-2-yl or pyridyl group;

or a salt thereof with a mineral or organic acid, in the form of a racemic mixture or of a pure enantiomer.

13. A pharmaceutical composition containing, as active principle, a compound according to claim 1 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

14. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 1 .

15. The compound of formula (I) according to claim 2 in which R 1 represents a 2,4-dichloro-3-methylphenyl, naphthyl, 6-methoxynaphth-2-yl, 3-methylbenzothiophen-2-yl, 3-methyl-5-chlorobenzothiophen-2-yl, 3-methyl-5-methoxybenzothiophen-2-yl, 3-methyl-6-methoxybenzothiophen-2-yl or 3-methyl-1-benzofur-2-yl group.

16. The compound of formula (I) according to claim 2 in which R 2 represents hydrogen and R 3 represents a benzo[1,3]dioxol-5-yl or phenyl group which is unsubstituted or substituted with a halogen.

17. The compound of formula (I) according to claim 2 in which R 4 represents a group —CONR 8 R 9 and —NR 8 R 9 represents a di(C 1 –C 4 )alkylamino radical, a pyrrolidinyl or piperidyl group which is unsubstituted or substituted one or two times with a methyl or a halogen.

18. The compound of formula (I) according to claim 2 in which R 5 represents a group —CH 2 NR 11 R 12 in which —NR 11 R 12 represents an ethylisobutylamino, ethylisopropylamino, ethyl-tert-butylamino, diisopropylamino, cyclopentylmethylamino or cyclopentylethylamino radical or a piperidyl radical which is unsubstituted or substituted one or more times with a methyl or a halogen.

19. The compound according to claim 2 of formula:

in which:

R 1 represents a 2,4-dichloro-3-methylphenyl, naphthyl, 6-methoxynaphth-2-yl, 3-methylbenzothiophen-2-yl, 3-methyl-5-chlorobenzothiophen-2-yl, 3-methyl-5-methoxybenzothiophen-2-yl, 3-methyl-6-methoxybenzothiophen-2-yl, or 3-methyl-1-benzofur-2-yl group;

R 3 represents a benzo[1,3]dioxol-5-yl or phenyl group which is unsubstituted or substituted with a halogen;

R 8 and R 9 , together with the nitrogen atom to which they are attached, constitute a di(C 1 –C 4 )alkylamino, pyrrolidinyl or piperidyl radical which is unsubstituted or substituted one or two times with a methyl or a halogen;

R 11 and R 12 , together with the nitrogen atom to which they are attached, constitute an ethylisobutylamino, ethylisopropylamino, ethyl-tert-butylamino, diisopropylamino, cyclopentylmethylamino or cyclopentylethylamino radical or a piperidyl radical which is unsubstituted or substituted one or more times with a methyl or a halogen;

or a salt thereof with a mineral or organic acid, or a solvate or hydrate or said compound or said salt.

20. (R,R) 2-((3-(1,3-benzodioxoI-5-yl)-3-(((6-methoxy-2-naphthyl)sulphonyl)amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide or a salt, solvate or hydrate thereof, or a solvate or hydrate of said salt according to claim 8 .

21. (R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-(((6-methoxy-2-naphthyl)sulphonyl)-amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide hydrochloride according to claim 20 .

22. A pharmaceutical composition containing, as active principle, a compound according to claim 2 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

23. A pharmaceutical composition containing, as active principle, a compound according to claim 3 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

24. A pharmaceutical composition containing, as active principle, a compound according to claim 4 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

25. A pharmaceutical composition containing, as active principle, a compound according to claim 5 or a pharmaceutically acceptable salt and/or thereof, or a solvate or hydrate of said compound or said salt.

26. A pharmaceutical composition containing, as active principle, a compound according to claim 6 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

27. A pharmaceutical composition containing, as active principle, a compound according to claim 7 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

28. A pharmaceutical composition containing, as active principle, a compound according to claim 8 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

29. A pharmaceutical composition containing, as active principle, a compound according to claim 15 or a pharmaceutically acceptable salt thereof, or a solvte or hydrate of said compound or said salt.

30. A pharmaceutical composition containing, as active principle, a compound according to claim 16 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

31. A pharmaceutical composition containing, as active principle, a compound according to claim 17 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

32. A pharmaceutical composition containing, as active principle, a compound according to claim 18 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

33. A pharmaceutical composition containing, as active principle, a compound according to claim 19 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

34. A pharmaceutical composition containing, as active principle, a compound according to claim 20 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

35. A pharmaceutical composition containing, as active principle, a compound according to claim 21 or a pharmaceutically acceptable salt thereof, or a solvate or hydrate of said compound or said salt.

36. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 2 .

37. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 3 .

38. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 4 .

39. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 5 .

40. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 6 .

41. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 7 .

42. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 8 .

43. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment am effective amount of a compound according to claim 15 .

44. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 16 .

45. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 17 .

46. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 18 .

47. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 19 .

48. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 20 .

49. A method for treating pain or inflammation which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 21 .

50. (R,R) 2-((3-(1,3-benzodioxol-5-yl)-3-(((6-methoxy-2-naphthyl)sulphonyl)amino)propanoyl)amino)-3-(4-((2,6-cis-dimethyl-1-piperidyl)methyl)phenyl)-N-isopropyl-N-methylpropanamide fumarate according to claim 20 .