Patent EP-0081425-B1 (EP)
IPC: A61K31/18
Filed: 1982-11-30
Granted: 1985-09-18
Abstract: 1. Claims (for the Contracting States : BE, CH, DE, GB, IT, LI, LU, NL, SE) Medicament possessing lipid-regulating properties, characterized by the fact that it contains, as active substance, if necessary in the state of a physiologically acceptable salt, and if necessary, in association with a pharmaceutical vehicle, a compound of the formula :  see diagramm : EP0081425,P37,F1  in which : R1 , R2 represent each independently of one another : - a hydrogen atom ; - a linear or branched lower alkyl radical having from 1 to 4 carbon atoms ; - a cycloalkyl radical comprising from 3 to 6 carbon atoms ; - an aryl radical, unsubstituted or substituted by a nitro, amino, trifluoromethyl group or halogen atom or by a linear or branched lower alkyl residue having from 1 to 4 carbon atoms, by an alkoxy residue having from 1 to 4 carbon atoms, particularly methoxy, by an alkylsulfonyl group -SO2 R in which R is an alkyl residue having from 1 to 4 carbon atoms, by a sulfamyl group -SO2 NR'R" in which R' and R" represent, independently of one another, a hydrogen atom or an alkyl residue having from 1 to 4 carbon atoms ; R3 , R4 , R5 and R6 represent, independently of one another : - a hydrogen atom ; - a nitro group, an amino group, trifluoromethyl group or a halogen ; - a linear or branched lower alkyl residue having from 1 to 4 carbon atoms, an alkoxy residue having from 1 to 4 carbon atoms, an alkylsulfonyl group -SO2 R in which is an alkyl residue having from 1 to 4 carbon atoms, a sulfamyl group -SO2 NR'R" in which R' and R" represent, independently of one another, a hydrogen atom or an alkyl residue having from 1 to 4 carbon atoms ; provided that when one at least of the substituents R3 to R6 represents a NH2 group at the para position or a CH3 group at the para position, one at least of the other substituents of the aromatic nucleus is different from hydrogen ; R7 , R8 and R9 represent, independently of one another : - a hydrogen atom ; - an alkyl radical having 1 to 6 carbon atoms ; - a cycloalkyl radical comprising from 3 to 6 carbon atoms ; - an aralkyl radical, particularly phenylalkyl or naphthylalkyl, in which the alkyl radical has from 1 to 4 carbon atoms, unsubstituted or substituted by a nitro group, an amino group, a trifluoromethyl group, or halogen atom or by a linear or branched lower alkyl residue, by an alkoxy residue having from 1 to 4 carbon atoms, particularly methoxy, by an alkylsulfonyl group, -SO2 R2 in which R is an alkyl residue having from 1 to 4 carbon atoms, by a sulfamyl group -SO NR'R" in which R' and R" represent, independently of one another, a hydrogen atom or an alkyl residue having from 1 to 4 carbon atoms ; R10 represents : - a hydrogen atom ; - an acyl group comprising from 1 to 12 carbon atoms ; - n and m vary, independently of one another, from 0 to 10, preferably form 0 to 5, provided that the sum n + m does not exceed 12, preferably does not exceed 5. 1. Claims (for the Contracting State AT) Process for preparing a compound of formula :  see diagramm : EP0081425,P39,F2  in which : R1 , R2 each represent independently of one another : - a hydrogen atom ; - a linear or branched lower alkyl radical having from 1 to 4 carbon atoms ; - a cycloalkyl radical comprising from 3 to 6 carbon atoms ; - an aryl radical, unsubstituted or substituted by a nitro group, an amino group, a trifluoromethyl group, a halogen atom or by a linear or branched lower alkyl residue having from 1 to 4 carbon atoms, by an alkoxy residue having from 1 to 4 carbon atoms, particularly methoxy, by an alkylsulfonyl group -SO2 R in which R is an alkyl residue having from 1 to 4 carbon atoms, by a sulfamoyl group -SO2 NR'R" in which R' and R" represent, independently of one another, a hydrogen atom or an alkyl residue having from 1 to 4 carbon atoms ; R3 , R4 , R5 and R6 represent, independently of one another : - a hydrogen atom ; - a nitro, amino, trifluoromethyl group or a halogen ; - a linear or branched lower alkyl residue having from 1 to 4 carbon atoms, an alkoxy residue having from 1 to 4 carbon atoms, an alkylsulfonyl -SO2 R group in which R is an alkyl residue having from 1 to 4 carbon atoms, a sulfamoyl -SO2 NR'R" group in which R' and R" represent, independently of one another, a hydrogen atom or an alkyl residue having from 1 to 4 carbon atoms ; provided that one at least of the substituents R3 to R6 is different from hydrogen ; and provided that when one at least of the substituents R3 to R6 represents a NH2 group at the para position or a CH3 group at the para position, one at least of the other substituents of the aromatic nucleus is different from hydrogen ; R7 , R8 and R9 represent, independently of one another : - a hydrogen atom ; - an alkyl radical having from 1 to 6 carbon atoms ; - a cycloalkyl radical comprising from 3 to 6 carbon atoms ; - an aralkyl radical, particularly phenylalkyl or naphthylalkyl, in which the alkyl radical has from 1 to 4 carbon atoms, unsubstituted or substituted by a nitro, amino, trifluoromethyl, or a halogen or by a linear or branched lower alkyl residue having from 1 to 4 carbon atoms, by an alkoxy residue having from 1 to 4 carbon atoms, particularly methoxy, by an alkylsulfonyl -SO2 R2 group in which R is an alkyl residue having from 1 to 4 carbon atoms, by a sulfamoyl -SO2 NR'R" group in which R' and R" represent, independently of one another, a hydrogen atom or an alkyl residue having from 1 to 4 carbon atoms ; R10 represents : - a hydrogen atom ; - an acyl group comprising from 1 to 12 carbon atoms ; n and m vary, independently of one another, from 0 to 10, preferably from 0 to 5, provided that the sum n + m does not exceed 12, preferably does not exceed 5 ; characterized by the fact a sulfohalogenide of formula :  see diagramm : EP0081425,P40,F1  in which : X is a halogen group, particularly bromine of preferably chlorine ; A1 , A2 , A3 , A4 have any one of the meanings given for R3 , R4 , R5 and R6 , except NH2 ; is reacted on an amine of formula :  see diagramm : EP0081425,P40,F2  in which : n and m have the above indicated meanings ; R1 , R2 , R7 , R8 , R9 and R10 have the above indicated meanings.