Beecham Group Plc

Burroughs Wellcome Co.

Beecham Group P.1.c.

Irene Stirling

Brian P Clarke

John B Harbridge

Thomas T Howarth

Hamish Christopher Wood

David F Corbett

Stephen H Calvert

Gordon Bruton

The compounds of the formula (II): ##STR1## or pharmaceutically acceptable salts or esters thereof wherein A is a hydrogen atom or an esterifying radical; X is an alkyl group of 1-12 carbon atoms optionally substituted by a hydroxy, amino, acylamino of C.sub.1-6 alkoxy group, which substituents are not on the carbon atom adjacent to the nitrogen atom; or a C.sub.5-7 cycloalkyl group; or a phenylalkyl group wherein the carbon atom content of the alkyl part is 1-6 and the phenyl part is optionally substituted with a fluorine, bromine, chlorine, C.sub.1-6 alkyl, or C.sub.1-6 alkoxy; with the proviso that when X represents an optionally substituted phenylalkyl group and A represents C.sub.1-3 alkyl, then the --CO.sub.2 A group is attached to the alkyl part of the phenylalkyl group; have been found to be .beta.-lactamase inhibitors and antibacterial agents. Their preparation and use is described.

A-deoxy-a-aza derivatives of clavulanic acid, a process for their

A compound of formula (I) or a salt or ester thereof: ##STR1## Pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt or pharmaceutically acceptable ester thereof are also disclosed.

Compounds containing beta-lactams

Derivatives of clavulanic acid, a process for their preparation and

A compound of formula (I) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof: ##STR1## wherein R represents an alkyl or aralkyl group, substituted on an alkyl carbon atom other than that adjacent to --NH-- group, with one or more functional groups selected from halogen, non-aromatic heterocyclyl linked through carbon, aromatic heterocyclyl, nitro, oxo, --OR.sup.1, SR.sup.1 --P(O)R.sup.2 R.sup.3, --NR.sup.4 R.sup.5, .dbd.NR.sup.6, or a sulphur linked organic radical, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are various organic radicals. Processes for the preparation of these compounds and pharmaceutical compositions containing them are also disclosed.

.beta.-Lactam compounds

The compounds of the formula (I): ##STR1## and esters thereof wherein R.sub.1 is a lower alkyl group or a phenyl group and R.sub.2 is a hydrogen atom or R.sub.2 together with R.sub.1 represents the residue of a fused benzene ring are .beta.-lactamase inhibitors and anti-bacterial agents. Their preparation and use is described.

Secondary amines of clavulanic acid are useful as beta-lactamase inhibitors that enhance the effectiveness of penicillins or cephalosphorins and also have antibacterial properties in their own right.

9-Deoxy-9-amino-clavulanate antibacterial agents

The compounds of the formula (II): ##STR1## pharmaceutically acceptable salts thereof, esters thereof and acid addition salts thereof wherein X is a C.sub.1-6 alkylene group, a C.sub.3-8 cycloalkylene group or a C.sub.3-8 cycloalkyl C.sub.1-4 alkylene group, have been found to be .beta.-lactamase inhibitors and antibacterial agents. Their preparation and use is described.

The compounds of the formula (XVII) ##STR1## and their esters wherein R.sub.2 is a hydrogen, fluorine, chlorine or bromine atom or an alkyl group of 1-3 carbon atoms, an alkoxyl group of 1-3 carbon atoms, an acyloxyl group of 1-3 atoms, a hydroxyl group, an alkoxycarbonyl group containing 1-3 carbon atoms in the alkoxy part, or a group --N(R.sub.5)CO.R.sub.6, --N(R.sub.5)SO.sub.2 R.sub.6 or --CO-NR.sub.5 R.sub.6 where R.sub.5 is a hydrogen atom or an alkyl group of 1-3 carbon atoms or a phenyl or benzyl group and R.sub.6 is an alkyl group of 1-3 carbon atoms or a phenyl or benzyl group; R.sub.3 is a hydrogen, fluorine or chlorine atom or an alkyl group of 1-3 carbon atoms, an alkoxyl group of 1-3 carbon atoms; or an acyloxyl group of 1-3 carbon atoms R.sub.4 is a hydrogen fluorine or chlorine atom or an alkyl group of 1-3 atoms or an alkoxyl group of 1-3 carbon atoms; and X is a bond or alkylene group of 1-4 carbon atoms; have been found to be .beta.-lactamase inhibitors and antibacterial agents. Their preparation and use is described.

.alpha.-Amino deoxy clavulanic acid antibacterial agents

Esters of the compound of the formula: ##STR1## are useful for their antibacterial and .beta.-lactamase inhibitory activity.

Clavudienes

The compounds of the formula (II): ##STR1## and pharmaceutically acceptable salts and esters thereof wherein X is a C.sub.1-6 alkylene group; m is 1, 2 or 3; n is 1, 2 or 3; A is oxygen, sulphur, --CH.sub.2 -- or --NR.sup.3 -- wherein R.sup.3 is hydrogen, C.sub.1-6 alkyl, phenyl or phenyl (C.sub.1-6)alkyl; R.sup.1 is hydrogen, oxo, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy or phenyl; and R.sup.2 is hydrogen, oxo, C.sub.1-6 alkyl or phenyl: with the proviso that if m and n are both 1 then A is --CH.sub.2 -- and R.sup.2 is not oxo: have been found to be .beta.-lactamase inhibitors and antibacterial agents. Their preparation and use are described.

Tetrahydropyridyl derivatives of clavulanic acid, a process for their

The present invention provides the compound of the formula (II): ##STR1## and salts and esters thereof.

9-Nitromethyldeoxyclavulanic acid derivatives preparation and

Compounds of the formula ##STR1## wherein CO.sub.2 R is an ester group, are useful for their .beta.-lactamase inhibitory activity.

Antibacterial agents

The compound of the formula (II): ##STR1## and its pharmaceutically acceptable salts and esters may be produced by ozonolysis of clavulanic acid and its derivatives. The compound has antibacterial and .beta.-lactamase inhibiting activity.

Oxoclavams

Novel pteridines of formula (I), ##STR1## wherein R is a lower alkyl group, optionally substituted with a hydroxy group and R.sup.1 and R.sup.2 are the same or different and each is a lower alkyl group having together at least 3 carbon atoms or R.sup.1 and R.sup.2, together with the carbon atom in the pteridine ring structure, form a spirocycloalkyl ring system having 4 to 6 carbon atoms outside the pteridine ring structure, and their method of preparation. The above compounds have bacteriostatic activity.

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Reigate, United Kingdom

Irene Stirling