GB1128382A - New benzene-sulphonyl semicarbazides and preparations containing them - Google Patents

Abstract

1,128,382. Benzene-sulphonyl semicarbazides. FARBWERKE HOECHST A.G. 6 May, 1966 [6 May, 1965], No. 20090/66. Heading C2C. Novel compounds of Formula I, wherein R represents (a) a phenyl radical which optionally contains up to three substituents selected from C 1-4 alkyl, C 2-4 alkenyl, C 1-4 alkoxy, C 2-4 alkenoxy, C 1-4 (alkoxyalkoxy), trifluoromethyl and methylenedioxy radicals and halogen atoms, (b) a thienyl radical which is optionally substituted by one or two substituents selected from halogen atoms and C 1-4 alkyl, C 1-4 alkoxy, C 2-4 alkenyloxy, C 1-4 (alkoxyalkoxy), phenyl- C 1-4 alkoxy and aryl radicals, or by a C 3-4 polymethylene chain linked at its two ends to the thienyl radical, (c) a furyl radical which is optionally substituted by one or more substituents selected from halogen atoms and methyl groups, (d) a phenyl radical bound via a saturated or unsaturated, branched or unbranched aliphatic hydrocarbon group containing from 1 to 4 carbon atoms and which may contain an oxygen atom instead of one CH 2 - group, the phenyl radical optionally containing one or more substituents selected from halogen atoms and C 1-4 alkyl or C 1-4 alkoxy radicals, (e) a cyclohexyl or cyclohexenyl radical or (f) a C 1-11 alkyl radical or an unsaturated aliphatic C 2-11 hydrocarbon radical, Y represents a -CH 2 -CH 2 - or -CH 2 -CH(CH 3 )- group, R<SP>1</SP> represents (a) an alkylene-imino radical containing 3 to 7 carbon atoms wherein the alkylene chain, may be substituted by 2 to 4 methyl groups or by an alkyl or alkoxy radical containing up to 3 carbon atoms, (b) an aliphatic hydrocarbon imino radical containing 5 carbon atoms which is unsaturated or contains an endoalkylene group having 1 to 3 carbon atoms which may be substituted by C 1-4 alkyl or C 1-4 alkoxy or (c) the radical -NR 1 R 2 , wherein R 1 represents a C 1-4 alkyl radical and R 2 represents a C 1-4 alkyl or benzyl radical, are prepared by (a) reacting an R-CO-NH-Y-substituted benzene sulphonamide with an R<SP>1</SP>-substituted carbamic acid ester, -thiocarbamic acid ester or -urea, (b) reacting a hydrazine of formula R<SP>1</SP>-NH 2 , or a salt thereof, with an R-CO-NH-Y- substituted benzenesulphonyl isocyanate, benzenesulphonyl carbamic acid ester, or benzenesulphonyl thiocarbamic ester, carbamic acid halide or urea, (c) reacting an R-CO-NH-Y- substituted benzenesulphochloride with an R<SP>1</SP>- substituted urea, (d) hydrolysing a benzenesulphonyl-isosemicarbazide ether or -isothiosemicarbazide ether or 1-benzenesulphonyl-3- R<SP>1</SP>-parabanic acid, (e) exchange of the sulphur atom for an oxygen atom in known manner in a benzenesulphonyl thiosemicarbazide of Formula II, or (f) introduction of the radical RCO in one or more steps, into a benzenesulphonyl semicarbazide of Formula III. 1 - [4 - (# - benzamido - ethyl) - benzenesulphonyl] - 3 - pentamethylene - imino - parabanic acid is prepared by reacting 1-pentamethyleneimino-parabanic acid with 4-(#-benzamidoethyl)-benzenesulphochloride. 4 - [4 - (# - amino - ethyl) - benzenesulphonyl]- 1,1 - pentamethylene - semicarbazide and 4-[4-(#- amino - ethyl) - benzenesulphonyl] - 1,1 - (ymethyl - pentamethylene) - semicarbazide are prepared by hydrolysis of the corresponding acetylamino compounds. Pharmaceutical compositions which have blood sugar lowering action, for oral administration, comprise a compound of Formula I together with a carrier.