US 6,610,845 B1 · Thioester derivatives of thiazolyl acetic acid and their use in the preparation of cephalosporin compounds

Abstract

The present invention provides new thioester derivatives of thiazolyl acetic acid of the general formula (I), wherein, R1 represents H, trityl, CH3, CRaRbCOOR2 (Ra and Rb independently of one another represents hydrogen or methyl and R2 represents H or C1-C4 alkyl). also, the invention provides a method by which the said thioester derivatives can be prepared by reacting thiazolyl acetic acid of the general formula (IV) with 1,2,5,6 tetrahdro-2-methyl-5,6 dioxo-1,2,4-triazin-3-thiol of the formula (VI) in a solvent, in presence of an organic base and with the help of Vilsmeier reagent of the formula (V). The so obtained thioester derivatives are reacted with 7-amino-cephem carboxylic acids of the general formula (III) to produce cephalosporin antibiotic compounds having the general formula (II).

Claims11

Dependent claims

A process for preparing a compound of formula (II)

wherein, R1 represents H, trityl, CH3, CRaRbCOOR2 (Ra and Rb independently of one another represents hydrogen or methyl and R2 represents H or C1-4 alkyl);
R3 is CH3, —CH═CH2, CH2OCH3, CH2OCOCH3,
R4 is H or a salt or a carboxylic protecting group or a inner salt when R3 is
comprising acylating a compound of formula (III)
wherein, R5 is H or trimethylsilyl;
R3 and R4 are defined as above with a compound of formula I
wherein, R1 is as defined above, in the presence of an organic solvent and a base at a temperature in the range of −10° C. to +30° C.

4 more elements

Dependencies are inferred from the claim text.

Thioester derivatives of thiazolyl acetic acid and their use in the preparation of cephalosporin compounds

Life of this patent

Thioester derivatives of thiazolyl acetic acid and their use in the preparation of cephalosporin compounds

Life of this patent

Abstract

Claims11