申请人:ELI LILLY AND COMPANY
公开号:EP0014566A1
公开(公告)日:1980-08-20
Novel thiazolineazetidinone vinyl halides useful in the preparation of certain cephem antibiotics are described. They are of the formula
wherein X is chloro or bromo; R10 is hydrogen or a carboxylic acid protecting group; and
Rs is
(a) hydrogen, C1-C4 alkyl or halo (C1-C4 alkyl);
(b) a group R. wherein R6 is phenyl or phenyl substituted by 1 or 2 groups selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy, protected hydroxy, carbamyl, trifluoromethyl and methanesulfonamido;
(c) a group of the formula R6(O)mCH2-
wherein m is I or O and R6 is defined above;
(d) a group of the formula R6aCH2-
wherein R6a is cyclohexadienyl, 2-furyl, 2-thienyl, or 3-thienyl; or
(e) a group of the formula -COOR wherein R is hydrogen or a carboxylic acid protecting group;
and when R10 is hydrogen the alkali metal salts of the acids represented thereby.
The compounds are prepared from the corresponding enols by action of halogenating compounds derived from triaryl phosphites and chlorine or bromine.
本文介绍了可用于制备某些头孢抗生素的新型噻唑啉酮乙烯基卤化物。它们的化学式为
其中 X 是氯或溴,R10 是氢或羧酸保护基团,以及
Rs 是
(a) 氢、C1-C4 烷基或卤代(C1-C4 烷基);
(其中 R6 是苯基或被 1 或 2 个选自氟、氯、溴、碘、硝基、氰基、C1-C4 烷基、C1-C4 烷氧基、受保护羟基、氨甲酰基、三氟甲基和甲磺酰胺基的基团取代的苯基;
(c) 式 R6(O)mCH2- 的基团
其中 m 为 I 或 O,R6 如上定义;
(d) 式 R6aCH2- 的基团
其中 R6a 是环己二烯基、2-呋喃基、2-噻吩基或 3-噻吩基;或
(e) 式-COOR 的基团,其中 R 是氢或羧酸保护基;
以及当 R10 为氢时,其代表的酸的碱金属盐。
这些化合物是由相应的烯醇在三芳基亚磷酸和氯或溴衍生的卤化化合物的作用下制备的。