Patent CA-1079290-A (CA)
Inventor: RAMUZ HENRI
IPC: C07D409/04
Filed: 1979-03-26
Granted: 1980-06-10
Abstract: ABSTRACT OF THE DISCLOSURE     This invention relates to compounds of the general formula                   (I) or an acid addition salt thereof, or            (II) in which n stands for 2 or 3, X represents a sulphur atom, SO or SO2, R represents a group of the formula       or          (a)                 (b) in which R1, R2 and R3 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, aryl-(lower alkoxy), aryloxy, phenyl, nitro, trifluoro-methyl, hydroxy, cyano, di(lower alkyl)amino or lower alkanoyloxy group or two adjacent R1, R2 and R3 symbols together represent a methylenedioxy, ethylenedioxy or butadien-1,3-ylene-1,4-group, R4 represents a hydrogen atom or a lower alkyl group, R5, R6 and R7 each represent a hydrogen or halogen atom or a lower alkyl, lower alkoxy, hydroxy or benzyloxy group or two ad-jacent R5, R6 and R7 symbols together represent a methylenedioxy or ethylene-dioxy group, Y1, represents a straight-chain or branched chain, optionally hydroxy-substituted, aliphatic group containing 1 - 7 carbon atoms, of which 1 - 3 carbon atoms are present in the chain, Z represents a straight-chain or branched chain, optionally hydroxy-substituted, aliphatic group contain-ing 1 - 8 carbon atoms, or which 1 - 4 carbon atoms are present in the chain, m stands for zero or 1, Y represents a straight chain or branched-chain, optionally hydroxy-substituted, aliphatic group containing 2 - 8 carbon atoms, and T represents a group of the formula (i)   (ii)                   (iii) or in which A represents the group   in which R4 represents a hydrogen atom or an alkyl group containing 1 - 5 carbon atoms, R8 denotes a leaving atom or group, and Zm, R5, R6 and R7 have the above-mentioned meanings, or an acid addition salt of compound (II) in which T denotes the group                  (iii) The invention also relates to a process for preparing compounds of formula I and II which comprises either: (a) when a compound of formula I is required, reacting an acid of the general formula                         (XVII) in which R, X, Y1 and n have the same meanings as above with an amine of the general formula   (VIIa) wherein the various symbols are as defined above, and, if desired, the pro-duct is converted to its acid addition salt; or (b)  when a compound of formula (II) is required, when T represents a radical (i), reacting a compound of the general formula   (XIV) in which R and R8 have the same meanings as above, with a compound of the general formula                         (V) in which n has the same meaning as above, and oxidising the product if X in formula (II) is to denote SO or SO2, or when T represents a radical (ii), acylating a compound of the general formula   in which R, X, Y, Z, R5, R6, R7, m and n have the same meanings as above, or when T represents a radical (iii), reacting a compound of the general formula                           (VIa) in which R, Y, X and n have the same meanings as above, with an amine of the general formula   (XVI) in which R4 has the same meaning as above, and if desired, converting the product to its acid addition salt. The compounds of the present invention are precursors in the pro-duction of sulphur-containing compounds claimed in our copending Canadian Patent Application Serial No. 216,313 filed December 18, 1974 which possess coronary dilating properties.