Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1976-03-19
1978-07-25
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
542430, 542442, 424246, 544 27, 544 28, 544 25, C07D50116, A61K 31545
Patent
active
041030842
ABSTRACT:
Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## (where R is thienyl or furyl; R.sup.a and R.sup.b are each selected from hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, phenyl, naphthyl, thienyl, furyl, carboxy, C.sub.2-5 alkoxycarbonyl and cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; and m and n are each 0 or 1 such that the sum of m and n is 0 or 1) exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including 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 R.sup.a and R.sup.b is other than hydrogen have also shown unusually high activity against Pseudomonas organisms. Important compounds of the above type include those in which the 7.beta.-acylamido group is a syn-2-carboxymethoxy-2-(fur-2-yl)acetamido, syn-2-(2-carboxyprop-2-yloxyimino)-2-(fur-2-yl)acetamido or syn-2-(1-carboxycyclopent-1-yloxyimino)-2-(fur-2-yl)acetamido group.
REFERENCES:
patent: 3769277 (1973-10-01), Long et al.
patent: 3830700 (1974-08-01), O'Callaghan et al.
Bradshaw Janice
Cook Martin Christopher
Gregory Gordon Ian
Daus Donald G.
Glaxo Laboratories Limited
Rivers Diana G.
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