C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 205/08 (2006.01) A61K 31/40 (2006.01) C07D 498/04 (2006.01) C07D 499/88 (2006.01)
Patent
CA 2127677
The invention relates to novel 2-bromo- and 2-nitroxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo-azetidines, to processes for the preparation thereof and to the use thereof wherein the novel compounds have the formula: (see foemula I) ¦ wherein R1 and R2 are hydrogen or bromine, R3 is Me2-C=C-COOR4 wherein R4 is hydrogen, methyl, benzyl or some other carboxy-protective group, and X is bromine or nitroxy group (-ONO2). 2-bromo- and 2-nitroxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo-azetidines are prepared by reacting derivatives of protected penicillanic acid 1,1-dioxides with DBN reactant and treated with thionyl chloride, the obtained residue is passed through a silica gel column with methylene chloride as eluant or the obtained residue is dissolved in tetrahydrofuran and treated with tetrabutyl ammonium bromide and after the treatment a derivative of 2-bromo, 3-bromo or 2-bromo-3,3-dibromo-4-oxo-azetidine is isolated, which derivative may be subjected to a reaction with silver nitrate in 2-propanol and, after the treatment of the reaction mixture, derivatives of 2-nitroxy-, 3-bromo-or 2-nitroxy-3,3-dibromo- 4-oxo- azetidine are isolated. The obtained substances are useful intermediates in the synthesis of beta lactam analogons or as components in formulations having antibacterial, inhibitory, antitumour or antagonistic action.
Borden Ladner Gervais Llp
Dionicko Drustvo Pliva Farmaceutska Kemijska Prehrambena I. Kozmeticka Industrija
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