申请人:ELI LILLY AND COMPANY
公开号:EP0136177A2
公开(公告)日:1985-04-03
7β-Acylamino-3-azido-3-cephem-4-carboxylic acid esters are obtained from the corresponding 3-halo or 3-sulfonyloxy-3-cephem esters and an alkali metal azide. The 3-azido compounds as the free acids or salts are antibacterial agents while in esterified form react with alcohols and phenols to provide 2-alkoxy (or 2-phenoxy)-3-amino-3-cephem esters and isomeric ring expanded 4,7-bicyclo β-lactam compounds, namely [2R-(2a,7a,8a)-4-alkoxy (or 4-phenoxy)-9-oxo-8-acylamino-6-thia-1,3-diazabicyclo[5.2.0]non-3-ene-2-carboxylic acids and esters and the corresponding 3-aikoxy (or 3-phenoxy) 1,4-diazabicyclo[5.2.0]non-3-ene-2-carboxylic acids and esters. The products obtained from the azide possess antibacterial properties.
7β-Acylamino-3-azido-3-cephem-4-carboxylic acid esters 可从相应的 3-halo 或 3-sulfonyloxy-3-cephem esters 和碱金属叠氮化物中获得。游离酸或盐形式的 3-叠氮化合物是抗菌剂,而酯化形式的 3-叠氮化合物会与醇和酚反应,生成 2-烷氧基(或 2-苯氧基)-3-氨基-3-头孢环酯和异构扩环 4,7- 双环 β-内酰胺化合物,即[2R-(2a,7a,8a)-4-烷氧基(或 4-苯氧基)-9-氧代-8-乙酰氨基-6-硫杂-1,3-二氮杂双环[5.2.0]壬-3-烯-2-羧酸及酯和相应的 3-烷氧基(或 3-苯氧基)-1,4-二氮杂双环[5.2.0]壬-3-烯-2-羧酸及酯。从叠氮化物中获得的产品具有抗菌特性。