Cephalosporins having a 7-(carboxy substituted...

Details Cephalosporins having a 7-(carboxy substituted... Cephalosporins having a 7-(carboxy substituted...

C - Chemistry, Metallurgy

07

D

260/101, 260/104

C07D 501/06 (2006.01) C07D 307/54 (2006.01) C07D 333/24 (2006.01)

Patent

CA 1059991

ABSTRACT OF THE DISCLOSURE Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure Image (where R is thienyl or furyl; Ra and Rb are each selected from hydrogen, C1-4 alkyl; C2-4 alkenyl, C3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C2-5 alkoxycar- bonyl and cyano, or Ra and Rb together with the carbon atom to which they are attached form a C3-7 cycloalkylidene or cycloalkenylidene group; and P is selected from specified vinyl and substituted methyl groups) exhibit broad spec- trums antibiotic activity characterised by particularly high activity against gram negative microorganisms, inclu- ding those which produce .beta.-lactamases. The compounds, which are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer, have particularly high in vitro activity against strains of Escherichia coli, Haemophilus influenzae and Proteus organisms; compounds wherein at least one of Ra and Rb is other than hydrogen have also shown unusually high activity against Pseudomonas organisms. Important compounds of the - 1 - above type include those in which the 7.beta.-acylamido group is a syn-2-carboxymethoxy-2-(fur-2-yl)acetamido, syn-2-(2-car- boxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido or syn-2- (1-carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)-acetamido group. - 1a -

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