Derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, processes for the preparation thereof and their use

Abstract

3-Bromo- and 3,3-dibromo-4-oxo-1-azetidines of the formula I ##STR1## wherein R.sub.1 is hydrogen or bromo, R.sub.2 is hydrogen or bromo, R.sub.3 is hydrogen, ##STR2## wherein R.sub.4 is hydrogen, methyl, benzyl or some other protective group, R.sub.5 is hydrogen, alkyl, alkylaryl, a heterocyclic ring, Y is a halo atom, X is a halo atom, alkoxy group, nitroxy group are provided along with processes for the preparation thereof and the use thereof. The 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines can be prepared by reacting 2-sulfinic acid derivatives, with various halogenating agents, and after treating the reaction mixture, 2-halo derivatives of 3-bromo- and 2,2-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 treating 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 antirumour therapy.

Dependencies are inferred from the claim text.