AMIDE DERIVATIVES OF 2-OXO-1-AZETIDINESULPHONIC ACIDS

摘要

2-Oxo-1-azetidinesulphonic acids of the formula < IMG > I in which the group H2N< IMG > represents an amino-substituted, 5- or 6-membered, aromatic heterocycle containing 1 or 2 nitrogen atoms and optionally also an oxygen, selenium or sulphur atom, R1 signifies lower alkyl which is substituted (a) by lower alkynyl, halogen, azido, amino, mono- or di-lower alkylamino, lower alkanoyloxyamino, lower alkanesulphonamido, optionally amino-, halogen-, lower alkyl- or lower alkoxy-substituted benzenesulphonamido, tri -lower alkylammonio, thiocyanato, hydroxy, lower alkanoyloxy, carbamoyloxy, carbamoyl, di-lower alkylcarbamoyl, cyano, hydroxylaminocarbonyl, lower alkoxyaminocarbonyl, sulpho, sulphothio, phosphonato, monoor di-lower alkylphosphonato, sulphamoyl, lower alkylthio, lower alkylsulphenyl or lower alkylsulphonyl or (b) by a 5- to 7 -membered, aromatic, unsaturated or saturated heterocyclyl-or heterocyclyl-CO-group which contains nitrogen and optionally also oxygen, selenium or sulphur and which is optionally substituted by lower alkyl, carbamoyl, sulpho-lower alkyl or mono- or di-lower alkylamino and R2 signifies hydrogen or a lower organic group, the group -NOR1 being present at least partially in the syn-form, in racemic form or in the form of the 3S-enantiomer, as well as pharmaceutically compatible salts of these compounds. Further, their manufacture by acylation or sulphonylation as well as benzthiazole thioesters of the formula < IMG > IIa in which H2N< IMG >has the above significance and R10 signifies lower alkyl which is substituted (a) by lower alkynyl, di-lower alkylamino, lower alkanoyloxyamino, lower alkanesulphonamido, optionally amino-, halogen-, lower alkyl- or lower alkoxy-substituted benzenesulphonamido-, thiocyanato, hydroxy, lower alkanoyloxy, carbamoyloxy, carbamoyl, cyano, lower alkoxyaminocarbonyl, di -lower alkylphosphonato, sulphamoyl, lower alkylthio, lower alkylsulphenyl or lower alkylsulphonyl or (b) by a 5- to 7-membered, aromatic, unsaturated or saturated heterocyclyl or heterocyclyl -CO- group which contains nitrogen and optionally also oxygen,selenium or sulphur and which is optionally substituted by lower alkyl, carbamoyl or di-lower alkylamino, the group =NOR10 being present at least partially in the syn-form, which can be used in the acylation and their preparation by esterifying corresponding carboxylic acids. Finally, novel carboxylic acids which can be used in the above process and a process for the preparation of carboxylic acids in which R1 represents cyano-lower alkyl. The compounds of formula I have antimicrobial activity.