Halogen derivatives of clavulaic acid
AssigneeGlaxo Laboratories Limited
InventorsPeter C. Cherry, Gordon I. Gregory, Peter Ward
Life of this patent
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Abstract
Novel halogen derivatives of clavulanic acid are described which are of value in the preparation of a range of clavulins which either inhibit .beta.-lactamases or show activity against strains of both gram-positive and gram-negative bacteria. Processes for preparing the halogen derivatives are described and methods for converting them into the active clavulins are given.
Claims6
A compound of the formula (II) ##STR4## wherein Hal represents a chlorine, bromine or iodine atom and R.sup.1 is selected from the group consisting of alkyl and alkenyl of up to 8 carbon atoms;
- alkyl and alkenyl of up to 8 carbon atoms having a substituent selected from the group consisting of methoxy, fluoro, chloro, bromo, iodo, cyano, acetoxy, pivaloyloxy, p-bromobenzoyl and carboethoxy;
- phenyl;
- benzyl;
- phenyl or benzyl having a substituted selected from the group consisting of chloro, o-nitro, p-nitro, cyano, p-methyl and p-methoxy;
- diphenylmethyl;
- triphenylmethyl;
- fur-2-ylmethyl;
- thien-2-ylmethyl;
- pyrid-4-ylmethyl;
- fur-2-ylmethyl, thien-2-ylmethyl or pyrid-4-ylmethyl substituted by lower alkyl on the heterocyclic group;
- a cycloalkyl group containing up to 12 carbon atoms;
- tetrahydropyranyl;
- phthalidyl;
- and a stannyl group, the tin atom having three substituents selected from the group consisting of C.sub.1-4 alkyl, phenyl, benzyl, phenyloxy and benzyloxy;
- or the E-isomer thereof.
p-Nitrobenzyl-(3R,5R,Z)-2-(2-bromethylidene)clavam-3-carboxylate.
p-Nitrobenzyl-(3R,5R,Z)-2-(2-chloroethylidene)clavam-3-carboxylate.
Dependencies are inferred from the claim text.