Verfahren zur Herstellung von Hydrindensulfonylharnstoffen und -sulfonylsemicarbaziden

摘要

Novel anti-diabetically effective sulphonylureas of the general formula wherein A is an alkyl, alkenyl, aryl, aralkyl, aryloxyalkyl, arylthioalkyl, cycloalkyl, cycloalkenyl, thienyl, furyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, cycloalkylalkoxy, cycloalkenyloxy, or cycloalkenylalkoxy radical which may be substituted by at least one member selected from halogen atoms and alkyl and alkoxy radicals, or A is the radical -N(V)(W), wherein V and W, which may be the same or different, are hydrogen atoms or alkyl, cycloalkyl, aryl or aralkyl radicals or, together with the adjacent N-atom, form a saturated heterocyclic radical, R1 is a hydrogen atom, a C1- 3 alkyl radical or an aralkyl radical and R2 is a straight chain or branched saturated or unsaturated aliphatic hydrocarbon radical, which can be interrupted by oxygen or sulphur atoms, or is a saturated or unsaturated cycloaliphatic hydrocarbon radical which can be substituted by alkyl or alkoxy radicals and can be interrupted by oxygen or sulphur atoms, or is an aryl or aralkyl radical or is an alkylene-imino radical containing 3 to 7 carbon atoms which can be substituted by alkyl radicols or can contain an endo-alkylene radical having up to 3 carbon atoms, are prepared: (a) by the interaction of a hydrindene-sulphonyl compound, A-CO.NR1-(-Ar-)-SO2X (Ar is a hydrindene residue), and the compound Y-R2, where one of the two substituents X and Y is an amino or amide group and the other is an isocyanate group or a group converted into an isocyanate group under the reaction conditions, (b) by the interaction of a hydrindene-sulphonyl halide, A-CONR1-(-Ar-)-SO2 Halogen, and a urea, H2N.CO.NH.R2, or the corresponding parabanic acid derivative and in the latter case hydrolysis of the intermediate obtained, (c) by acylating an amino-hydrindene R1NH-(-Ar-)-SO2NHCONHR2 with a reactive derivative of an acid of the general formula A.COOH, or (d) by hydrolysis of compounds of the formulae A.CONR1-(-Ar-)-SO2NHC(:X1)NHR2 (wherein X1 is S or NH) or A.CONR1-(-Ar-)-SO2NH.C(:NR2).Z alkyl (wherein Z is O or S). N - (2 - Amino - hydrindene - 5 - sulphonyl) - N1 - cyclohexylurea is obtained by saponification of the corresponding acetamido compound.