NOVEL DERIVATIVES OF 3-BROMO- AND 3,3 DIBROMO-4-OXO-1-AZETIDINES, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME

摘要

The invention relates to derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines of general formula I to processes for the preparation thereof and the use thereof. wherein wherein R4 is hydrogen, methyl, benzyl or some other protective group, R5 is hydrogen, alkyl, alkylaryl, a heterocyclic ring, Y is halo atom, X is halo atom, alkoxy group, nitroxy group. According to the invention derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines are prepared by the reaction of 2-sulfinic acid derivatives, preferably 2-substituted sulfinamides of 4-oxo-azetidines with various halogenating agents, and after the treatment of the reaction mixture, 2-halo derivatives of 3-bromo- and 3,3-dibromo-4-oxo-azetidines are isolated and are subjected to a reaction with silver tetrafluoroborate and alcohols to give the corresponding 2-alkoxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo azetidines, or 2-halo derivatives of 3-bromo- and 3,3-dibromo-4-oxo azetidines are subjected to a reaction with silver nitrate in 2-propanol to give, after the treatment of the reaction mixture, 2-nitroxy derivatives of 3-bromo and 3,3-dibromo-4-oxo-1-azetidines. Some newly prepared compounds are deprotected and derivatives having a free carboxy group are obtained. The prepared compounds are components in pharmaceutical compositions effective in antibacterial or antitumour therapy.