Abstract: Antibiotic compounds of the general formula ##STR1## [wherein R is a phenyl, thienyl or furyl group; R.sup.a and R.sup.b, which may be the same or different, 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 from a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; R.sup.c is hydrogen or lower alkyl; R.sup.d is hydroxy, lower alkoxy, aralkoxy or aryloxy; m and n are each 0 or 1 such that the sum of m and n is 0 or 1; and P is selected from a hydrogen atom, a halogen atom and various organic groups] and non-toxic derivatives thereof.

Abstract: 2-Vinylclavem compounds are disclosed which have been found of value in the synthesis of thio-derivatives of clavulanic acid which possess antibiotic and .beta.-lactamase inhibitory activity. Methods for preparing the vinylclavem compounds are disclosed and processes for preparing the thio-derivatives are given.

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.

Abstract: The invention provides novel antibiotic compounds which are 7.beta.-acylamidoceph-3-em-4-carboxylic acids, and non-toxic derivatives thereof, and 6.beta.-acylamidopenam-3-carboxylic acids, and non-toxic derivatives thereof, characterized in that the acylamido group has the structure ##STR1## where R is a hydrogen atom or an organic group and R.sup.a is a hydrogen atom or an acyl group. The compounds are syn isomers or exist as mixtures containing at least 75% of the syn isomer. These antibiotic compounds possess high antibacterial activity against a range of gram positive and gram negative organisms coupled with particularly high stability to .beta.-lactamases produced by various gram negative organisms. The invention is also concerned with the administration of the compounds.

Abstract: Antibiotic compounds of the general formula ##STR1## [wherein R is a phenyl, thienyl or furyl group; R.sup.a and R.sup.b, which may be the same or different, 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 wth the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; R.sup.c and R.sup.d, which may be the same or different, each represents a hydrogen atom or a substituting group e.g. an alkyl group or substituted alkyl group; or R.sup.c and R.sup.d together with the nitrogen atom to which they are attached form a saturated or unsaturated heterocyclic ring which contains 5-7 ring members and which may contain additional hetero atoms, and may be substituted by lower alkyl; R.sup.e represents hydrogen or C.sub.

Abstract: Cephalosporin antibiotics in which the 7.beta.-acylamido group has the formula ##STR1## (where R.sup.1 is furyl or thienyl and R.sup.2 is C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl, furylmethyl or thienylmethyl) and in which the 3-position substituent is a pyridiniummethyl group wherein the pyridine ring is optionally substituted by carbamoyl, carboxy, carboxymethyl, sulpho or methyl exhibit high antibacterial activity against a broad range of gram-positive and gram-negative organisms, coupled with particularly high stability to .beta.-lactamases produced by various gram-negative organisms and good stability in vivo, particularly to esterases.

Abstract: Cephalosporin antibiotics having the formula: ##STR1## (where R is thienyl, furyl or phenyl; R.sup.a is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl or phenyl, and R.sup.b is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, phenyl, carboxy or C.sub.2-5 alkoxycarbonyl, 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 Y is the residue of a nitrogen nucleophile and their physiologically acceptable derivatives exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases.

Abstract: 3-Carbamoyloxymethyl and 3-N-methylcarbamoyloxymethyl cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## where R is thienyl, furyl or phenyl; R.sup.a is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl or phenyl, and R.sup.b is hydrogen, carboxy, C.sub.2 -C.sub.5 carbalkoxy or any of the groups designated for R.sup.a, 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; 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; and also shown unusually high activity against Pseudomonas organisms.

Abstract: 3-Acetoxymethyl cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## where R is thienyl, furyl or phenyl; R.sup.a is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl or phenyl, and R.sup.b is hydrogen, carboxy, C.sub.2 -C.sub.5 carbalkoxy or any of the groups designated for R.sup.a, 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; 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; and also shown unusually high activity against Pseudomonas organisms.

Abstract: Cephalosporin antibiotics having the formula: ##STR1## (where R is thienyl, furyl or phenyl; R.sup.a is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl or phenyl, and R.sup.b is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, phenyl, carboxy or C.sub.2-5 alkoxycarbonyl, 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; R.sup.13 is C.sub.1 -C.sub.6 alkyl, C.sub.3-7 cycloalkyl, phenylalkyl, phenyl or naphthyl, thiadiazolyl, diazolyl, triazolyl, tetrazolyl, thiazolyl, thiatriazolyl, oxazolyl, oxadiazolyl, pyridyl, pyrimidyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, triazolopyridyl or purinyl, and n is 0, 1 or 2 and their physiologically acceptable derivatives exhibit broad spectrum antibiotic activity characterized by particularly high activity against gram negative microorganisms, including those which produce .beta.-lactamases.

Abstract: Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## where R.sup.1 is a furyl, thienyl or phenyl group and R.sup.2 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl or phenyl group and in which the 3-position substituent is a carbamoyloxymethyl group possess a particularly valuable combination of properties, exhibiting high antibacterial activity against a broad range of gram positive and gram negative organisms, paticularly high stablity to .beta.-lactamases produced by various organisms, and stability in vivo. The compounds are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer. Particularly important compounds of this type are (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph- 3-em-4-carboxylic acid (syn isomer) and its non-toxic derivatives, e.g. the sodium salt.

Abstract: Cephalosporin antibiotics in which the 7.beta.-acylamido group has the structure ##STR1## (WHERE R is phenyl, 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, aminocarbonyl, N-substituted aminocarbonyl 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; R.sup.c is hydrogen or C.sub.1-4 alkyl; 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.

Abstract: .alpha.-(Etherified oximino)carboxylic acids, represented by the formula:- ##STR1## where R is hydrogen or an organic group having 1-20 carbon atoms and R.sup.a is an etherifying monovalent organic group having 1-16 carbon atoms linked to the oxygen atom through a carbon atom, and the corresponding acid chlorides, are useful intermediates in the preparation of highly active, highly .beta.-lactamase-stable 7.beta.-[.alpha.-(etherified oximino)acylamido]-ceph-3-em-4-carboxylic acid antibiotics. The compounds are syn isomers or exist as mixtures of syn and anti isomers containing at least 75% of the syn isomer.

Abstract: Cephalosporin antibiotics in which the 7.beta.-acylamido group is syn 2-furyl-2-methoxyiminoacetamido and in which the 3-position substituent is a chloroalkylcarbamoyloxymethyl group exhibit high antibacterial activity against a broad range of gram positive and gram negative organisms, particularly high stability to .beta.-lactamases produced by various organisms, and stability in vivo. The compounds are syn isomers or exist as mixtures of syn and anti isomers containing at least 90% of the syn isomer.