Aryl-Sulphonyl-Semicarbazides

摘要

1,176,310. Sulphonyl-ureas. FARBENFABRIKEN BAYER A.G. 14 Nov., 1968 [25 Nov., 1967; 2 Jan., 1968; 2 Sept., 1968], No. 54121/68. Heading C2C. Novel compounds (I) (including alkali metal and alkaline earth metal salts thereof) in which R is H or alkyl, R1 and R11 signify hydrogen or halogen or alkyl, aryl, aralkyl or cycloalkyl which may be substituted by halogen, alkyl, alkoxy or CF 3 , or R1 and R11 may be joined together to constitute an alkylene chain, NR111R1111 is a saturated or unsaturated, monocyclic or polycyclic radical which contains one or more hetero atoms, e.g. N, O, S, SO or SO 2 , and which may be substituted by alkyl, alkoxy, hydroxy or oxo, X signifies an oxygen or sulphur atom or a nitrogen atom having attached thereto a hydrogen atom or an alkyl, aryl or aralkyl radical which may be substituted by halogen, alkyl, alkoxy or CF 3 , Y is a direct bond, or a straight chain or branched C 1-8 alkylene radical, and n is 0, 1, 2, 3 or 4, are obtained: (a) by reacting a hydrazine H 2 N.NR111R1111 or a salt thereof with an aryl-sulphonamide derivative, Het.(CH 2 ) n -CO.NRY-C 6 H 4 .SO 2 NHC(: O)A (Het signifies the X-containing heterocyclic radical illustrated in Formula (I) above and A signifies, for example, halogen, azido, alkoxy, aryloxy, alkylmercapto, arylmercapto, unsubstituted or substituted amino, cyclic amino or acylamino; aryl-sulphonyl methyl urethanes, i.e. A is OMe, are obtained by interaction of the corresponding sulphonamide and methyl chloroformate), or with isocyanate, Het.(CH 2 ) n -CONR.Y.C 6 H 4 .SO 2 NCO; (b) by reacting a sulphonamide, (obtained by the interaction of Het.(CH 2 ) n . COCl and H.N.R.Y.C 6 H 4 .SO 2 NH 2 ), or an alkali metal salt thereof with an isocyanate, OCN NR111R1111, or a hydrazine derivative, B.CO.NH NR111R1111, wherein B is, for example, the same as A; (c) by reacting a sulphohalide, Het.(CH 2 ) n .CO.NR.Y.C 6 H 4 .SO 2 .Halogen, with a semicarbazide, H 2 N.CO.NH.NR111R1111; (d) by oxidatively hydrolysing a compound of the general formula wherein Z signifies SH; or acidic or alkaline hydrolysis is utilized when Z signifies NH 2 , O-alkyl, S-alkyl or Cl; (e) by acylating a compound of the general formula, with a carboxylic acid or derivative thereof of the general formula Het.(CH 2 ) n .CO.R11111 (R11111 signifies, e.g. hydroxy, alkoxy, aryloxy or halogen); (f) by oxidizing a compound of the general formula (m is 0 or 1); or (g) by hydrolysing a corresponding parabanic acid derivative of (I). Pharmaceutical preparations exhibiting a blood-sugar depressing effect contain as active ingredient the above novel compounds; administration may be orally or parenterally.