Patent DE-3343815-A1 (DE)
Inventor: BINDAMADHAVAN VENUGOPALAN DR
IPC: C07D207/22
Filed: 1983-12-03
Abstract: For the Contracting State : BE CH LI DE FR GB IT LU NL SE 1. A compound of the general formula I  see diagramm : EP0144892,P11,F1 in which X and X' each denote C1 -C5 -alkyl, C1 -C5 -alkoxy, halogen or the SO2 CH3  radical, Y and Y' each denote hydrogen or halogen, R1 denotes hydrogen, C1 -C5 -alkyl or substituted alkyl of the formula (CH2 )n XR4 , in which n is an integer from 1-3, X represents O or S, and R4  denotes hydrogen, C1 -C3 -alkyl or C1 -C5 -alkanoyl, R2  and R3  are identical or different and each denote hydrogen, C1 -C5 -alkyl, C1 -C5 -alkanoyl or substituted alkyl of the formula (CH2 )n XR4 , in which n is an integer from 1-3, X represents O or S, and R4 denotes hydrogen, C1 -C3 -alkyl or C1 -C5 -alkanoyl, R2  and R3 , together with the N atom to which they are bonded, denote the pyrrolidino, piperidino, imidazolino or pyrimidino radical, or R1 and R2 , together with the carbon atom and the nitrogen atom to which they are bonded, denote the pyrrolidino, piperidino, imidazolino or pyrimidino radical, which can be monosubstituted or polysubstituted by C1 -C5 -alkanoyl, C1 -C5 -alkyl or by phenyl which is unsubstituted or substituted by halogen, NO2 , CN, CF3  or SO3 H, and R3  denotes hydrogen,C1 -C5 -alkyl, substituted alkyl of the formula (CH2 )n XR4 , in which n is an integer from 1-3, X represents O or S, and R4  denotes hydrogen, C1 -C3 -alkyl or C1 -C5 -alkanoyl, or denotes C1 -C5 -alkanoyl, C2 -C5 -carbalkoxy or phenyl which is unsubstituted or substituted by halogen, NO2 ,CN, CF3 or SO3 H, and stereoisomers and pharmaceutically acceptable salts thereof. For the Contracting State : AT 1. A process for the preparation of a compound of the general formula I  see diagramm : EP0144892,P13,F1  in which X and X' each denote C1 -C5 -alkyl, C1 -C5 -alkoxy, halogen or the SO2 CH3  radical, Y and Y' each denote hydrogen or halogen, R1  denotes hydrogen, C1 -C5 -alkyl or substituted alkyl of the formula (CH2 )n XR4 , in which n is an integer from 1-3, X represents O or S, and R4 denotes hydrogen, C1 -C3 -alkyl or C1 -C5 -alkanoyl, R2  and R3  are identical or different and each denote hydrogen, C1 -C5 -alkyl, C1 -C5 -alkanoyl or substituted alkyl of the formula (CH2 )n XR4 , in which n is an integer from 1-3, X represents O or S, and R4 denotes hydrogen, C1 -C3 -alkyl or C1 -C5 -alkanoyl, R2  and R3 , together with the N atom to which they are bonded, denote the pyrrolidino, piperidino, imidazolino or pyrimidino radical, or R1  and R2 , together with the carbon atom and the nitrogen atom to which they are bonded, denote the pyrrolidino, piperidino, imidazolino or pyrimidino radical, which can be monosubstituted or polysubstituted by C1 -C5 -alkanoyl, C1 -C5 -alkyl or by phenyl which is unsubstituted or substituted by halogen, NO2 , CN, CF3 or SO3 H, and R3  denotes hydrogen,C1 -C5 -alkyl, substituted alkyl of the formula (CH2 )n XR4 , in which n is an integer from 1-3, X represents O or S, and R4 denotes hydrogen, C1 -C3 -alkyl or C1 -C5 -alkanoyl, or denotes C1 -C5 -alkanoyl, C2 -C5 -carbalkoxy or phenyl which is unsubstituted or substituted by halogen, NO2 ,CN, CF3 or SO3 H, and stereoisomers and pharmaceutically acceptable salts thereof, which comprises reacting a compound of the general formula II  see diagramm : EP0144892,P14,F2 in which X, X', Y and Y' have the meaning give above, with phosphorus oxychloride and an amide of the general formula III  see diagramm : EP0144892,P14,F3  in which R1 , R2  and R3  have the meaning give above, to give a compound of the general formula I and, if appropriate, converting this into its pharmaceutically acceptable acid addition salt.