Patents Assigned to Glaxo Laboratories Limited
  • Patent number: 4529734
    Abstract: 2-Formyloxymethyl-clavam is described and its use as an antifungal compound against a range of fungi for both medical and horticultural and agricultural use is disclosed. Processes for isolating the compound from fermentations of strains of Streptomyces clavuligerus are described.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: July 16, 1985
    Assignee: Glaxo Laboratories Limited
    Inventors: Eunice J. Napier, James K. Evans, David Noble, Michael Bushell
  • Patent number: 4367175
    Abstract: The invention provides the compound (2R,5R,Z)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo-[3,2,0]-heptane -2-carboxylic acid and its salts in purified form and pharmaceutical compositions containing them and a process for the purification of such compounds by conversion in aqueous media to the lithium salt of the above acid and precipitation thereof.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: January 4, 1983
    Assignee: Glaxo Laboratories Limited
    Inventors: Ian D. Fleming, David Noble, Hazel M. Noble formerly Gillett, Wilfred F. Wall
  • Patent number: 4351842
    Abstract: Compounds of the general formula: ##STR1## in which A is a benzene ring or a carbocyclic aromatic group consisting of two or three fused benzene rings, the group A being linked to the nitrogen containing ring at two adjacent carbon atoms and the benzene ring or each benzene ring optionally carrying one or more substituents which may be the same or different, and may be alkyl, aryl, halo, hydroxy, acyloxy or alkoxy, or two adjacent positions in a ring may be substituted so as to form a methylene dioxy group (--O--CH.sub.2 --O--);R.sub.1 and R.sub.2 which may be the same or different, each represent hydrogen; an alkyl group which contains 1 to 6 carbon atoms and which may be substituted; a hydroxycarbonyl or an alkoxycarbonyl group; andone of R.sub.3 and R.sub.4 represents hydrogen, an alkyl group which contains 1 to 6 carbon atoms and which may be substituted, or a hydroxy, alkoxy, hydroxycarbonyl or alkoxycarbonyl group and the other of R.sub.3 and R.sub.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: September 28, 1982
    Assignee: Glaxo Laboratories Limited
    Inventor: Richard J. Coles
  • Patent number: 4267320
    Abstract: The invention provides novel antibiotic cefuroxime esters of the formula ##STR1## (wherein R.sup.1 is a primary or secondary alkyl group containing 1 to 4 carbon atoms and R.sup.2 is a primary or secondary alkyl group containing 1 to 6 carbon atoms provided that at least one of the groups R.sup.1 and R.sup.2 is methyl). These compounds are useful as orally administrable broad spectrum antibiotics.
    Type: Grant
    Filed: July 27, 1979
    Date of Patent: May 12, 1981
    Assignee: Glaxo Laboratories Limited
    Inventors: Michael Gregson, Richard B. Sykes
  • Patent number: 4230622
    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.
    Type: Grant
    Filed: December 10, 1976
    Date of Patent: October 28, 1980
    Assignee: Glaxo Laboratories Limited
    Inventors: Peter C. Cherry, Gordon I. Gregory, Peter Ward
  • Patent number: 4228074
    Abstract: .beta.-Lactam compounds of the formula (I) ##STR1## (wherein R represents an esterified carboxyl group, --NR.sup.1 R.sup.2 R.sup.3 represents the residue of a nitrogen base, and R.sup.4 represents a hydrogen atom, a hydroxyl group or acylated or etherified hydroxyl group or the residue of a sulphur nucleophile) are disclosed, together with processes for their preparation. The compounds are valuable intermediates for the preparation or purification of further .beta.-lactam compounds having .beta.-lactamase inhibitory activity.
    Type: Grant
    Filed: September 8, 1977
    Date of Patent: October 14, 1980
    Assignee: Glaxo Laboratories Limited
    Inventors: Peter C. Cherry, Christopher E. Newall, Nigel S. Watson
  • Patent number: 4209616
    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.
    Type: Grant
    Filed: October 16, 1978
    Date of Patent: June 24, 1980
    Assignee: Glaxo Laboratories Limited
    Inventors: Michael Gregson, Martin C. Cook, Gordon I. Gregory
  • Patent number: 4193917
    Abstract: Novel semisynthetic .beta.-lactam intermediates of use in the production of cephalosporins, penicillins and related .beta.-lactam antibiotic compounds are provided. The novel compounds are prepared from .beta.-lactams obtained by cleavage of the 1,2-sulphur-carbon bond of a penicillin 1-oxide (with subsequent internal or external trapping of the sulphur atom to leave a residual substituent as the .beta.-lactam nitrogen) by removal of the said residual substituent by an oxidative cleavage reaction.
    Type: Grant
    Filed: August 12, 1976
    Date of Patent: March 18, 1980
    Assignee: Glaxo Laboratories, Limited
    Inventors: Derek H. R. Barton, Alan G. Long, Brian E. Looker, Edward M. Wilson, William G. Elphinstone
  • Patent number: 4192871
    Abstract: Pregnanes and androstanes are described which essentially possess a 3.alpha.-hydroxy group, a 5.alpha.-hydrogen atom or a 4.5- or 5,6-double bond, a 17.alpha.-hydrogen atom and an 11.beta.-aminoester group. Other optional substituents or double bonds may be present. The compounds have anaesthetic activity.
    Type: Grant
    Filed: May 22, 1978
    Date of Patent: March 11, 1980
    Assignee: Glaxo Laboratories Limited
    Inventors: Gordon H. Phillipps, Peter J. May, Barry E. Ayres
  • Patent number: 4169547
    Abstract: A container has a body with a nozzle at one end. A plunger can be pushed through the body by the insertion of a finger of the user through the opening in the body so as to force the contents of the container out through the nozzle.
    Type: Grant
    Filed: October 26, 1977
    Date of Patent: October 2, 1979
    Assignee: Glaxo Laboratories Limited
    Inventor: Robert E. Newell
  • Patent number: 4168309
    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 form a C.sub.3-7 cycloalkylidene or cycloalkenylidene group; m or n are each 0 or 1 such that the sum of m and n is 0 or 1; and R.sup.
    Type: Grant
    Filed: September 30, 1977
    Date of Patent: September 18, 1979
    Assignee: Glaxo Laboratories Limited
    Inventor: Barry E. Ayres
  • Patent number: 4165430
    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.
    Type: Grant
    Filed: June 15, 1976
    Date of Patent: August 21, 1979
    Assignee: Glaxo Laboratories Limited
    Inventors: Janice Bradshaw, Martin C. Cook, Gordon I. Gregory
  • Patent number: 4164447
    Abstract: A novel O-transcarbamoylase enzyme and its use in preparing a variety of 3-carbamoyloxymethyl cephalosporins from 3-hydroxymethyl cephalosporins and carbamoyl compounds are described.
    Type: Grant
    Filed: November 22, 1977
    Date of Patent: August 14, 1979
    Assignee: Glaxo Laboratories Limited
    Inventors: Ian D. Fleming, Michael K. Turner, Stephen J. Brewer
  • Patent number: 4162360
    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.
    Type: Grant
    Filed: September 13, 1977
    Date of Patent: July 24, 1979
    Assignee: Glaxo Laboratories Limited
    Inventors: Janice Bradshaw, Martin C. Cook, Gordon I. Gregory
  • Patent number: 4157278
    Abstract: This invention relates to a process for the production of water-soluble fractions from Streptomyces griseus mycelium and containing peptidoglycan material having immunostimulatory properties and to formulations containing such fractions. Several examples of the process are given.
    Type: Grant
    Filed: March 21, 1978
    Date of Patent: June 5, 1979
    Assignee: Glaxo Laboratories Limited
    Inventors: Gordon W. Ross, Monica J. Gardner nee Marshall, Walter Wolff
  • Patent number: 4144242
    Abstract: The invention provides the compound (2R,5R,Z)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo-[3,2,0]-heptane -2-carboxylic acid and its salts in purified form and pharmaceutical compositions containing them and a process for the purification of such compounds by conversion in aqueous media to the lithium salt of the above acid and precipitation thereof.
    Type: Grant
    Filed: December 16, 1976
    Date of Patent: March 13, 1979
    Assignee: Glaxo Laboratories Limited
    Inventors: Ian D. Fleming, David Noble, Hazel M. Noble (formerly Gillett), Wilfred F. Wall
  • Patent number: 4144392
    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.
    Type: Grant
    Filed: June 15, 1976
    Date of Patent: March 13, 1979
    Assignee: Glaxo Laboratories Limited
    Inventors: Janice Bradshaw, Martin C. Cook, Gordon I. Gregory
  • Patent number: 4144393
    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.
    Type: Grant
    Filed: March 18, 1976
    Date of Patent: March 13, 1979
    Assignee: Glaxo Laboratories Limited
    Inventors: Janice Bradshaw, Martin C. Cook, Gordon I. Gregory
  • Patent number: 4138555
    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.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: February 6, 1979
    Assignee: Glaxo Laboratories, Limited
    Inventors: Martin C. Cook, Gordon I. Gregory, Janice Bradshaw
  • Patent number: 4132849
    Abstract: A process for the preparation of a 3-hydroxymethyl cephalosporin compound which comprises selectively hydrolyzing a 3-formyloxymethyl cephalosporin compound under acidic conditions in the presence of a protic solvent whereby a 3-hydroxymethyl cephalosporin is produced.
    Type: Grant
    Filed: October 7, 1977
    Date of Patent: January 2, 1979
    Assignee: Glaxo Laboratories Limited
    Inventor: Barry E. Ayres