Patents Assigned to Beecham Group
  • Patent number: 4247709
    Abstract: The present invention relates to a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one and to certain compounds for use in that process.British Pat. Spec. No. 1,474,377 discloses inter alia that 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one possesses useful anti-inflammatory activity. A particularly favored process has now been discovered that can be used to produce 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one in particularly good yield.The present invention provides a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one which process comprises the hydrogenation of a compound of the formula (I): ##STR1## wherein Ar is a 6-methoxy-2-naphthyl group; X and Y are each hydrogen atoms or together represent a second bond between the carbon atoms to which they are attached; and R is a group such that --CO.sub.2 R represents an ester group convertible by hydrogenation to a CO.sub.2 H group.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: January 27, 1981
    Assignee: Beecham Group Limited
    Inventors: Carl J. Rose, David Miller
  • Patent number: 4246273
    Abstract: Compounds of the formula (I): ##STR1## wherein: Y is --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.dbd.C-- n is 1 to 5;R.sub.1 is hydrogen, or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1 to 12 carbon atoms;R.sub.2 is hydrogen, C.sub.1-4 alkyl, trifluoromethyl, or phenyl;R.sub.3 is hydroxy or protected hydroxy;R.sub.5 is hydrogen, C.sub.1-6 alkyl, phenyl or phenyl C.sub.1-6 alkyl, any of which phenyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or nitro groups; andX is CH.sub.2 andR.sub.4 is C.sub.1-9 alkyl, C.sub.3-8 cycloalkyl-C.sub.1-6 alkyl, phenyl-C.sub.1-6 alkyl or naphthyl-C.sub.1-6 alkyl, any of which groups may have one acyclic carbon-carbon bond interrupted by an oxygen atom; hydrogen, C.sub.3-8 cycloalky, phenyl or naphthyl, any of which phenyl of naphthyl moieties in R.sub.4 may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy or nitro groups; orR.
    Type: Grant
    Filed: March 27, 1979
    Date of Patent: January 20, 1981
    Assignee: Beecham Group Limited
    Inventor: Gordon Wootton
  • Patent number: 4246257
    Abstract: Skin treatment product for greasy or oily skin comprising an unpigmented oil-in-water or water-in-oil emulsion having dispersed therein 3 to 10% by weight of spherical polymer or copolymer particles having an average size of 5 to 15 microns. The polymer or copolymer particles are cross-linked polystyrene, polymethylmethacrylate or polyethylene microspheres. The oil of the emulsion is a volatile organic liquid in the amount of 1 to 30% of the weight of the emulsion and may be a silicone or silicon glycol.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: January 20, 1981
    Assignee: Beecham Group Limited
    Inventors: Thomas J. Elliott, David Ford
  • Patent number: 4244965
    Abstract: Compounds of the formula (I): ##STR1## and salts and esters thereof, wherein R.sub.1 is a hydrogen atom or a lower alkyl, aryl or aralkyl group, R.sub.2 and R.sub.3 are independently hydrogen, aryl, aralkyl, lower alkyl or substituted lower alkyl, or R.sub.3 is joined to R.sub.1 to form a 4-, 5-, or 6- membered ring or is joined to R.sub.2 to form a 5- or 6- membered ring with the proviso that when R.sub.2 is hydrogen, R.sub.1 is not hydrogen and R.sub.1 and R.sub.3 are not joined to form a group of the sub-formula (a) ##STR2## wherein R.sub.4 is a hydrogen atom or a NH.CO.R.sub.5 group wherein R.sub.5 is a lower alkyl, lower alkoxy lower alkyl, aryl, aralkyl, aryloxyalkyl, lower alkoxy or aryloxy group have .beta.-lactamase inhibitory and anti-bacterial properties.
    Type: Grant
    Filed: September 14, 1978
    Date of Patent: January 13, 1981
    Assignee: Beecham Group Limited
    Inventors: Thomas T. Howarth, Eric Hunt
  • Patent number: 4245089
    Abstract: Compounds of the formula (III): ##STR1## wherein R.sub.1 is alkyl of up to 3 carbon atoms and R.sub.2 is alkyl of up to 3 carbon atoms optionally joined to R.sub.1 so that R.sub.1 and R.sub.2 and the carbon atom to which they are attached form a spiro-cyclopentyl or spiro-cyclohexyl ring, and wherein the configuration about the .beta.-lactam ring is trans, are useful in the preparation of antibacterial .beta.-lactam compounds.A process for the preparation of the compounds of the formula (III), is also desired.
    Type: Grant
    Filed: January 25, 1979
    Date of Patent: January 13, 1981
    Assignee: Beecham Group Limited
    Inventors: Roger J. Ponsford, Robert Southgate
  • Patent number: 4243682
    Abstract: 4-(6-Substituted naphthyl)butan-2-ols,-butan-2-ones,-pentan-2-ols and -pentan-2-ones bearing a fluoro group in the naphthyl ring, and pro-drugs thereof, are anti-inflammatory agents. A typical embodiment is 4-(4-fluoro-6-methoxy-2-naphthyl)-butan-2-one.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: January 6, 1981
    Assignee: Beecham Group Limited
    Inventors: Alexander C. Goudie, Laramie M. Gaster
  • Patent number: 4243669
    Abstract: A class of 2-substituted benzisothiazolones carrying a nitrogen-containing heterocyclic ring are effective in inhibiting platelet aggregation and are therefore of value in the prophylactic and therapeutic treatment of thrombotic diseases.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: January 6, 1981
    Assignee: Beecham Group Limited
    Inventor: Keith H. Baggaley
  • Patent number: 4242262
    Abstract: The present invention provides the compound of the formula (II): ##STR1## and salts and esters thereof.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: December 30, 1980
    Assignee: Beecham Group Limited
    Inventor: Irene Stirling
  • Patent number: 4241074
    Abstract: A compound of the formula (I): ##STR1## wherein: X is O, S or H;Y is --CH.sub.2 --CH--, --CH.dbd.CH-- or --C.dbd.C--;n is 1 to 7;R.sub.1 is C.sub.1-4 alkyl;R.sub.3 is hydroxy or protected hydroxy;R.sub.4 is C.sub.1-9 alkyl, C.sub.3-8 cycloalkyl or C.sub.3-8 cycloalkyl--C.sub.1-6 alkyl; orR.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; andR.sub.5 is hydrogen or C.sub.1-6 alkyl; and salts thereof has useful pharmaceutical activity including bronchodilator activity.
    Type: Grant
    Filed: June 14, 1979
    Date of Patent: December 23, 1980
    Assignee: Beecham Group Limited
    Inventors: Frederick Cassidy, Alexander C. Goudie
  • Patent number: 4237131
    Abstract: A compound of the formula (I): ##STR1## wherein: X is O or S;Y is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--;n is 1 to 5;R.sub.1 is hydrogen or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1 to 12 carbon atoms;R.sub.2 is hydrogen or C.sub.1-4 alkyl;R.sub.3 is hydroxy or protected hydroxy;R.sub.4 is C.sub.1-9 alkyl, C.sub.3-8 cycloalkyl or C.sub.3-8 cycloalkyl-C.sub.1-6 alkyl; orR.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; andR.sub.5 is (CH.sub.2).sub.a NR.sub.6 R.sub.7, wherein a is 0 to 3 and R.sub.6 and R.sub.7 are hydrogen, C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl, or R.sub.6 and R.sub.7 taken with the nitrogen atom to which they are joined represent a 4 to 7 membered heterocyclic ring which may contain as sole further hetero atom one oxygen atom or one optionally C.sub.1-4 alkyl substituted nitrogen atom; allyl or propargyl; (CH.sub.2).sub.b --CO--(CH.sub.2).sub.c --CH.sub.
    Type: Grant
    Filed: June 14, 1979
    Date of Patent: December 2, 1980
    Assignee: Beecham Group Limited
    Inventors: Gordon Wootton, Richard W. Moore
  • Patent number: 4237161
    Abstract: Esters of an acid of formula: ##STR1## which is termed "monic acid" have activity against Gram-positive and Gram-negative organisms.
    Type: Grant
    Filed: August 7, 1978
    Date of Patent: December 2, 1980
    Assignee: Beecham Group Limited
    Inventors: Kong Luk, John P. Clayton, Norman H. Rogers
  • Patent number: 4235784
    Abstract: Esters of an acid of formula: ##STR1## which is termed "monic acid" have activity against Gram-positive and Gram-negative organisms.
    Type: Grant
    Filed: January 27, 1978
    Date of Patent: November 25, 1980
    Assignee: Beecham Group Limited
    Inventors: Kong Luk, John P. Clayton, Norman H. Rogers
  • Patent number: 4235882
    Abstract: It has been found that an antibiotic can be obtained by the fermentation of certain strains of Streptomyces olivaceus and related organisms and when pure this antibiotic is an extremely potent inhibitor of many .beta.-lactamases. This antibiotic which we designate MM 4550A may be obtained in substantially pure form by the chromatographic purification of the crude antibacterial complex obtained from the culture medium.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: November 25, 1980
    Assignee: Beecham Group Limited
    Inventors: Martin Cole, John D. Hood, Dennis Butterworth
  • Patent number: 4234726
    Abstract: Compounds of the formula (I): ##STR1## or a pharmaceutically acceptable salt thereof wherein the NR.sub.1 R.sub.2 moiety is a 5-, 6-, or 7-membered saturated heterocyclic ring; R.sub.3 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 1 to 4 carbon atoms; R.sub.4 is naphthyl or phenyl unsubstituted or substituted by one or two substituents selected from the group consisting of fluorine, chlorine, bromine, methoxyl, benzyloxyl, trifluoromethyl, methyl, cyano, nitro, acetoxyl, amino, methylamino, ethylamino, dimethylamino, diethylamino, acetamide, hydroxyl, methoxycarbonyl, ethoxycarbonyl, carboxamido, sulphonamido, carboxy, trifluoromethylthio, trifluoromethoxyl, methylsulphonyl, trifluomethylsulphonyl and methylthio; R.sub.5 is hydrogen or alkyl of 1 to 4 carbon atoms; R.sub.6 is hydrogen or alkyl of 1 to 4 carbon atoms; X is oxygen and the dotted line represents a single or double bond.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: November 18, 1980
    Assignee: Beecham Group Limited
    Inventor: Derek V. Gardner
  • Patent number: 4232022
    Abstract: This invention relates to pyrimidine derivatives for treating material and bacterical infestions in humans and animals.
    Type: Grant
    Filed: February 9, 1979
    Date of Patent: November 4, 1980
    Assignee: Beecham Group Limited
    Inventor: Roger J. Ponsford
  • Patent number: 4232005
    Abstract: The compounds of the formula: ##STR1## and salts and esters thereof are useful agents for the treatment of bacterial infections either alone or in combination with a penicillin or cephalosporin derivative.The preceding compounds may be prepared by the hydrogenation of a compound of the formula: ##STR2## wherein R is a hydrogen atom or an acyl group or a salt or ester thereof.
    Type: Grant
    Filed: December 5, 1977
    Date of Patent: November 4, 1980
    Assignee: Beecham Group Limited
    Inventor: Thomas T. Howarth
  • Patent number: 4230804
    Abstract: Novel re-usable water-insoluble penicillin acylase complexes are provided wherein a penicillin acylase is adsorbed on a water-insoluble polymer or co-polymer of methacrylic acid and cross-linked with a water-soluble aldehyde selected from the group consisting of glutaraldehyde, glyoxal and formaldehyde. The complexes are useful in the production of 6-APA from penicillins G and V.
    Type: Grant
    Filed: October 27, 1978
    Date of Patent: October 28, 1980
    Assignee: Beecham Group Limited
    Inventors: Thomas A. Savidge, Lawson W. Powell
  • Patent number: 4230232
    Abstract: In a screw capped bottle, a protuberance (7) cooperates with a notch (9) in a notch-bearing member (10) so that as the cap is screwed on, the protuberance bears on the notch-bearing member and one or both deforms to accommodate the threading movement until the protuberance snaps into the notch to terminate the movement. When screwing the cap off, there is an initial resistance to movement while the protuberance and/or notch-bearing member deforms. The protuberance then snaps out of the notch and the cap may be removed.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: October 28, 1980
    Assignee: Beecham Group Limited
    Inventor: Herbert A. Atkins
  • Patent number: 4228174
    Abstract: The compounds of the formula (II): ##STR1## and salts and esters thereof wherein R is an inert organic group of up to 18 carbon atoms and are able to inhibit the action of various bacterial .beta.-lactamases. Thus when a compound of the formula (II) or its salt or ester is used together with a penicillin or cephalosporin, the effectiveness of that penicillin or cephalosporin can be considerably enhanced. These novel synergysts can be prepared by etherification of an ester of clavulanic acid followed if desired by de-esterification. The novel synergysts also possess antibacterial activity.
    Type: Grant
    Filed: February 1, 1979
    Date of Patent: October 14, 1980
    Assignee: Beecham Group Limited
    Inventors: Roger J. Ponsford, Thomas T. Howarth
  • Patent number: 4228149
    Abstract: Sustained release composition comprising a water soluble veterinary medicament dispersed in a sheet of water insoluble polymer, which sheet is of a size and composition such that it is capable of being constrained in a position which allows oral administration and is, in the rumen, capable of moving relative to this position to retain the composition therein.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: October 14, 1980
    Assignee: Beecham Group Limited
    Inventors: Malcolm D. Brewer, Gerald J. L. Griffin