Thiophensulfonylharnstoffe und Verfahren zu ihrer Herstellung

摘要

1322980 Thiophen - sulphonyl - ureas FARBWERKE HOECHST AG 7 Aug 1970 [7 Aug 1969] 38255/70 Heading C2C Novel thiophen-2-sulphonyl-ureas of the general Formula I or a salt thereof, wherein X is in the 4 or 5 position and is hydrogen, fluorine, chlorine, bromine or methyl; Y is CH 2 , CH 2 CH 2 , or CH 2 CH(CH 3 ); and R is a C 4-6 alkyl, C 5-8 cycloalkyl or 3-methylcyclopentyl, 4-methyl cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 4 - chlorocyclohexyl, 4,4 - dimethylcyclohexyl, 3 - methyl - cyclopentenyl, methylcyclohexenyl, endo - alkylene - cyclohexyl, endoalkylene - cyclohexenyl, endoalkylene cyclohexyl methyl or endoalkylene - cyclohexenylmethyl may be prepared by (a) reacting an amine RNH 2 with an appropriately substituted sulphonyl-isocyanate, sulphonyl-carbamate, sulphonyl thiocarbamate, sulphonyl urea, semicarbazide or semicarbazone; (b) reacting a sulphonamide II with an R-substituted isocyanate, carbamate, thiocarbamate, carbamoyl halide or urea; (c) hydrolysing the corresponding sulphonyl isourea ether, sulphonyl isothiourea ether, sulphonyl parabanic acid or sulphonyl halo formic acid amidine; (d) adding water to the corresponding carbodiimide; (e) replacement of sulphur by oxygen in the thiourea radical of a corresponding sulphonyl thiourea; (f) oxidizing the corresponding sulphinyl or sulphenyl to sulphonyl; (g) acylating the thiophen sulphonyl urea III (h) reacting an R substituted urea with a corresponding sulphonyl halide; (i) replacement of sulphur in a thioamide group by oxygen; (j) saponification of a compound IV or V or a parabanic acid derivative of IV, wherein U is C 1-4 alkoxy or thioalkyl or halogen; or (k) reaction of an N-R-N1 hydroxy urea with a corresponding sulphinic acid halide or, in the presence of an acid condensation agent, the free sulphinic acid or alkali metal salt thereof. The intermediate thiophen sulphonamide II may be formed by chlorosulphonation followed by treatment of ammonia of the corresponding thiophen or condensation of an amino substituted thiophen sulphonamide with a substituted benzoyl chloride to form the amide group. The intermediate thiophen sutphonyl carbamic acid esters may be formed by condensation of the corresponding thiophen sulphonamide with a chloroformic ester. Pharmaceutical compositions of the compound I with the usual excipients show hypoglycemic activity when administered orally.