Verfahren zur Herstellung neuer antidiabetisch wirksamer Benzolsulfonyl-semicarbazide

摘要

Novel anti-diabetically effective compounds of the general formula (and the alkali metal, alkaline earth metal and ammonium salts thereof) wherein A is a straight chain or branched, saturated or unsaturated aliphatic or cycloaliphatic hydrocarbon radical or an aryl, aralkyl, aryloxyalkyl, arylmercaptoalkyl or heterocyclic radical, which may be substituted by at least one member selected from halogen atoms and alkyl and alkoxy radicals, X is a straight-chain or branched saturated or unsaturated divalent aliphatic hydrocarbon radical and R1 and R2, which may be the same or different, are straight-chain or branched, saturated or unsaturated aliphatic, cycloaliphatic or araliphatic hydrocarbon radicals or together with the adjacent N-atom form an alkylene-imino radical which can be substituted by alkyl, alkoxy or endoalkylene radicals or the alkylene fragment of such an alkylene imine ring can be interrupted by hetero atoms, are prepared: (a) by the interaction of a benzenesulphonyl compound, A.CO.X.Ph.SO2Y and a compound of general formula Z.N.R1R2 wherein one of the substituents Y and Z is an amino or amide group and the other is an isocyanate group or a group convertible under the reaction conditions into an isocyanate group, (b) by the interaction of a benzene-sulphonyl halide, A.COX.Ph.SO2.Halogen and a compound of formula H2N.CONH.NR1R2 or the corresponding parabanic acid, and (c) by hydrolysis of compounds of the formulae A.COX.Ph.SO2NH.C(: V).NHNR1R2 (wherein V represents S or NH) and A.COX.Ph.SO2.NHC(: N.NR1R2).U Alkyl (wherein U is O or S).