Novel 4-substituted azetidinones as precursors to 2-substituted-3-carboxy carbapenem antibiotics and a method of producing them
申请人:AMERICAN CYANAMID COMPANY
公开号:EP0504612A2
公开(公告)日:1992-09-23
4-substituted azetidinones having the formulae I and II:
with R¹, R², R³, R⁴, R⁵ and X defined hereafter, which are intermediates for the preparation of carbapenem and carbacephem antibacterials and processes for producing such antibacterials through the utilization of an acid mediated ring closure reaction. R¹is hydrogen, hydroxy (lower) alkyl or protected hydroxy (lower) alkyl; R²is selected from the group consisting of hydrogen and (C₁-C₆) alkyl; R³is hydrogen, or an organic group; R⁴is hydrogen or a suitable removable protecting group for an amide nitrogen; R⁵is hydrogen or a suitable removable protecting group for a carboxylic acid; Xis oxygen, sulfur, a moiety of the formula NR⁶.
具有式 I 和 II 的 4-取代氮杂环丁酮:
其中 R¹、R²、R³、R⁴、R⁵ 和 X 在下文中定义,它们是制备碳青霉烯类和碳青霉烯类抗菌药的中间体,以及通过利用酸介导的闭环反应生产此类抗菌药的工艺。R¹ 是氢、羟基(低级)烷基或受保护的羟基(低级)烷基;R² 选自氢和(C₁-C₆)烷基组成的组;R³ 是氢或有机基团;R⁴ 是氢或酰胺氮的合适的可去除保护基团;R⁵ 是氢或羧酸的合适的可去除保护基团;X 是氧、硫、式 NR⁶ 的分子。