Novel N-(arylsulphonyl) amino acid derivatives, process for their preparation and pharmaceutical compositions containing them

A compound of formula:

• 151
• in which:
• R1 is a phenyl, a naphthyl, a tetrahydronaphthyl, a quinolyl or an isocuinolyl, the said rings being unsubstituted or substituted one or more times with R10;
• R2 is a phenyl which is unsubstituted or substituted one or more times with R11, a phenyl(C1-C4)alkyl which is unsubstituted or substituted one or more times on the phenyl with R11, a naphthyl which is unsubstituted or substituted one or more times with R11, a cyclohexyl which is unsubstituted or substituted one or more times with R11;
• or R2 and R9 are linked together and constitute a (C3-C5)alkylene which is unsubstituted or substituted with R12 or a (C2-C4)alkylene which is interrupted with an oxygen atom or a sulphur atom and is unsubstituted or substituted with R12;
• or R2 and R9, together with the carbon atom and the nitrogen atom to which they are attached, constitute tetrahydroisoquinoline which is unsubstituted or substituted one or more times with a halogen, a hydroxyl, a (C1-C4)alkyl, a (C1-C4)alkoxy or a benzyloxy;
• R3 is hydrogen or a hydroxyl;
• R4 and R5 are each independently hydrogen or a (C1-C4)alkyl;
• or R4 and R5, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from 1-pyrrolidinyl, 1-piperidyl, perhydro-1-azepinyl, 4-morpholinyl, 4-oxo-1-piperidyl, dihydro-1-pyrrolyl or dihydro-2-imidazolyl, the said heterocyclic radicals being unsubstituted or substituted one or more times with R13;
• R6 is hydrogen and R6 can also be R8 when R7 is hydrogen;
• R7 is hydrogen or a (C1-C4)alkyl;
• R8 is hydrogen;
• a benzyl which is unsubstituted or substituted on the phenyl one or more times with R13;
• or a group ZR14;
• or R7 and R8, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from 1-pyrrolidinyl, 1-piperidyl, 1-perhydro-1-azepinyl, 4-morpholinyl, tetrahydro-2-pyrimidinyl, 1-piperazinyl or 1-piperazinyl substituted in position 4 with a (C1-C4)alkyl or a benzyl;
• or, when R7 is hydrogen, R6, and R8 are linked together to form a (C2-C4)alkylene which is unsubstituted or substituted one or more times with a (C1-C4)alkyl;
• R9 is hydrogen, a (C1-C4)alkyl or a phenyl(C1-C4)alkyl which is unsubstituted or substituted on the phenyl one or more times with R11;
• R10 is a halogen, a (C1-C4)alkyl, a (C1-C4)alkoxy, a hydroxyl, an amino, a (C1-C4)alkylamino or a di(C1-C4) alkylamino;
• R11 is a halogen, a (C1-C4)alkyl, a trifluoromethyl, a phenyl, a hydroxyl, a (C1-C4)alkoxy or a benzyloxy;
• or R11 is in the ortho position to the phenyl representing R2 and forms with R3 a methylene group or an ethylene group;
• or R11 is in the ortho position to the phenyl representing R2 and forms with R9 a methylene group or an ethylene group;
• R12 is a halogen, a (C1-C4)alkyl, a hydroxyl, a (C1-C4)alkoxy, a benzyloxy, an oxo, a phenyl, an acetyloxy or a trifluoroacetyloxy;
• R13 is a (C1-C4)alkyl, a halogen or a hydroxyl;
• R14 is a methyl, an amino, a (C1-C4)alkylamino, a di(C1-C4)alkylamino, a tri(C1-C4)alkylammonium, an amidino, a (C1-C4) alkylamidino, a guanidino, a (C1-C4)alkylguanidino, a hydroxyl, a (C1-C4)alkoxy, a (C1-C4)alkoxycarbonyl, a group -AlkN(R15)Alk′N(R′15)2, or a heterocyclic radical chosen from 1-pyrrolidinyl, 1-piperidyl, perhydro-1-azepinyl, pyridyl, imidazolyl, dihydroimidazolyl, imidazolidinyl, pyrimidinyl and indolyl;
• R15 and R′15 are, independently of each other, hydrogen or a (C1-C4)alkyl;
• R16 is hydrogen or a methyl, or R16 forms with R9 a methylene group;
• R17 is hydrogen or a methyl;
• Alk and Alk′ are, independently of each other, a (C1-C4) alkylene;
• Z is a (C2-C12)alkylene or a (C1-C6)alkylene which is interrupted or substituted with a (C5-C7)cycloalkyl or with a phenyl;
• C* is an asymmetric carbon atom;
• as well as the salts thereof with inorganic or organic acids.