Patents Assigned to Beecham Group Limited
  • Patent number: 4426389
    Abstract: 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.
    Type: Grant
    Filed: September 22, 1980
    Date of Patent: January 17, 1984
    Assignee: Beecham Group Limited
    Inventors: Irene Stirling, Brian P. Clarke
  • Patent number: 4426377
    Abstract: This invention provides the compounds of the formula (II): ##STR1## and salts and esters thereof, wherein R.sub.1 is H and R.sub.3 is H or an aryl, aralkyl, lower alkyl or substituted lower alkyl group or R.sub.1 and R.sub.3 are joined so that the CHR.sub.1.NH.CO.R.sub.3 moiety forms 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.The compounds have .beta.-lactamase inhibitory and anti-bacterial properties.The invention also provides a process for their preparation, and pharmaceutical compositions containing them.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: January 17, 1984
    Assignee: Beecham Group Limited
    Inventor: Thomas T. Howarth
  • Patent number: 4425332
    Abstract: Antacid dosage units comprising a finely divided solid antacid such as aluminium hydroxide dispersed in a fondant confectionary base are provided. Each dosage unit is sealed against moisture evaporation and may include antibacterial or antifungal preservatives as well as humectants and other adjuvants.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: January 10, 1984
    Assignee: Beecham Group Limited
    Inventor: Michael H. James
  • Patent number: 4424361
    Abstract: Process for the preparation of compounds of the formula (I): ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different, represent hydrogen, halogen, nitro, lower alkyl or lower alkoxy, where lower means of up to six carbon atoms, or any adjacent two of R.sub.1 to R.sub.4 taken together represent an alkylene group containing from 3 to 5 carbon atoms or a 1,4-buta-1,3-dienylene group, by removal of CH.sub.2 R.sub.5 wherein R.sub.5 is phenyl optionally substituted with one or two groups selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or nitro from a compound of formula (II): ##STR2## with an alkali metal C.sub.1-4 primary alkoxide. The compounds are used to inhibit allergic responses.
    Type: Grant
    Filed: January 14, 1981
    Date of Patent: January 3, 1984
    Assignee: Beecham Group Limited
    Inventor: John M. Tedder
  • Patent number: 4423033
    Abstract: An injectable formulation containing a soluble salt of amoxycillin has its stability on reconstitution improved by the incorporation therein of PVP.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: December 27, 1983
    Assignee: Beecham Group Limited
    Inventor: Charles B. Taskis
  • Patent number: 4421760
    Abstract: The compound of the formula (VI): ##STR1## pharmaceutically acceptable salts and pharmaceutically acceptable esters thereof, are useful for their antibacterial activity and for their .beta.-lactamase inhibitory activity. They may be combined in a synergistically effective amount with a penicillin or cephalosporin for the treatment of bacterial infections in humans and animals.
    Type: Grant
    Filed: June 17, 1981
    Date of Patent: December 20, 1983
    Assignee: Beecham Group Limited
    Inventor: Stephen J. Box
  • Patent number: 4420639
    Abstract: 4-(6'-Methoxy-2'-naphthyl) butan-2-one is described as having anti-inflammatory activity and an improved therapeutic ratio.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: December 13, 1983
    Assignee: Beecham Group Limited
    Inventors: Anthony W. Lake, Carl J. Rose
  • Patent number: 4416883
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof: ##STR1## wherein R is phenyl, 4-hydroxy phenyl, or a 5- or 6-membered heterocyclic ring containing up to three heteroatoms selected from oxygen, sulphur or nitrogen, optionally substituted with hydroxy, amino, halogen or C.sub.1-6 alkoxy;R.sup.1 represents hydrogen or C.sub.1-6 alkyl;R.sup.2 and R.sup.3 are the same or different and represent hydrogen, C.sub.1-6 alkyl, halogen, amino, hydroxy, or C.sub.1-6 alkoxy.Their preparation and use is described.
    Type: Grant
    Filed: June 24, 1981
    Date of Patent: November 22, 1983
    Assignee: Beecham Group Limited
    Inventor: Peter H. Bentley
  • Patent number: 4415584
    Abstract: Compounds of the formula (II): ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms, CO.sub.2 R.sub.2 is a carboxyl group, a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable esterified carboxyl group, are useful for their .beta.-lactamase inhibitory activity and to synergize the antibacterial activity of penicillins and cephalosporin.
    Type: Grant
    Filed: January 25, 1979
    Date of Patent: November 15, 1983
    Assignee: Beecham Group Limited
    Inventor: Eric Hunt
  • Patent number: 4413000
    Abstract: The present invention provides the compounds of the formula (II): ##STR1## and salts and esters thereof wherein R.sup.3 is a hydrogen atom or is an organic bonded via a carbon atom to the carbapenem ring, n is zero or one, X is a saturated or unsaturated hydrocarbon radical optionally substituted by bromo or chloro, and R.sup.4 is a C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.1-10 aralkyl or aryl group, any of such groups R.sup.4 being optionally substituted. These compounds are useful as antibacterial agents.
    Type: Grant
    Filed: July 8, 1981
    Date of Patent: November 1, 1983
    Assignee: Beecham Group Limited
    Inventor: Alfred J. Eglington
  • Patent number: 4413056
    Abstract: A process for the preparation of a compound of formula (I): ##STR1## wherein R.sup.1 is hydrogen, hydroxy, mercapto radical, a substituted or unsubstituted methoxy, ethoxy, methyl, ethyl, methyl thio, or ethylthio radical, a carbamoyloxy, carbamoylthio, C.sub.1-6 alkanoyloxy, C.sub.1-6 alkanoylthio, cyano, carboxy or carbamoyl radical; andR.sup.2 represents an acyl group which comprises hydrolysis of a compound of formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are as defined with respect to formula (I) hereinbefore and R.sup.3 represents benzyl or substituted benzyl; wherein the hydrolysis is catalyzed by a microbial serine proteinase.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: November 1, 1983
    Assignee: Beecham Group Limited
    Inventors: Ian R. Chester, Lawson W. Powell, David G. Roberts
  • Patent number: 4413002
    Abstract: Compounds of formula (I), or salts thereof: ##STR1## wherein: X is oxygen or sulphur, or >C.dbd.X represents ##STR2## Y is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--; n is 1 to 5;R.sub.1 is hydrogen or C.sub.1-6 alkyl;R.sub.2 is hydrogen or C.sub.1-4 alkyl; andR.sub.3 is C.sub.4-9 alkyl, C.sub.5-8 cycloalkyl, or C.sub.5-8 cycloalkyl --C.sub.1-6 alkyl; orR.sub.2 and R.sub.3 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group, having useful pharmacological activity, pharmaceutical compositions containing them and a process for their preparation.
    Type: Grant
    Filed: January 16, 1980
    Date of Patent: November 1, 1983
    Assignee: Beecham Group Limited
    Inventor: Gordon Wootton
  • Patent number: 4410535
    Abstract: Compounds of the formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: R.sub.1 is C.sub.1-6 alkyl;R.sub.2 is hydrogen or C.sub.1-7 acyl;R.sub.3 is C.sub.1-6 alkyl;R.sub.4 is a group CH.sub.2 R.sub.5 wherein R.sub.5 is hydrogen, C.sub.3-8 cycloalkyl or phenyl optionally substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.1-4 alkoxy, trifluoromethyl and halogen, having useful anti-emetic activity.
    Type: Grant
    Filed: November 30, 1981
    Date of Patent: October 18, 1983
    Assignee: Beecham Group Limited
    Inventor: Eric A. Watts
  • Patent number: 4409225
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: R.sub.1 is a C.sub.1-6 alkoxy group;R.sub.2 and R.sub.3 are the same or different and are hydrogen, halogen, CF.sub.3, C.sub.1-7 acyl, C.sub.1-7 acylamino, C.sub.1-6 alkyl-S(O).sub.n wherein n is 0, 1 or 2, nitro, or amino, aminocarbonyl or aminosulphonyl optionally substituted by one or two C.sub.1-6 alkyl groups;or R.sub.1 and R.sub.2 taken together are methylendioxy or ethylenedioxy in which case R.sub.3 is any one of the groups given for R.sub.1 and R.sub.2 above;R.sub.4 is hydrogen or C.sub.1-6 alkyl;R.sub.5 is hydrogen, C.sub.1-6 alkyl, phenyl or phenyl-C.sub.1-6 alkyl, either of which phenyl moieties may be substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, CF.sub.3 or halogen, and R.sub.6 is hydrogen; or R.sub.5 and R.sub.6 are attached to two adjacent carbon atoms and form together with these two carbon atoms a fused benzene ring, which benzene ring may be substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, CF.sub.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: October 11, 1983
    Assignee: Beecham Group Limited
    Inventor: Michael S. Hadley
  • Patent number: 4409207
    Abstract: The compound of the formula (I): ##STR1## and salts and esters thereof may be used as a .beta.-lactamase inhibitor to enhance the effectiveness of penicillins or cephalosporins.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: October 11, 1983
    Assignee: Beecham Group Limited
    Inventor: Brian C. Gasson
  • Patent number: 4409216
    Abstract: A compound, with hypoglycaemic activity, having formula (II) or a pharmaceutically acceptable acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur;R.sup.1 R.sup.2 are the same or different and represent hydrogen, halogen, C.sub.1-6 alkyl, phenyl, benzyl,C.sub.3-6 cycloalkyl, carbo-C.sub.1-6 alkoxy or C.sub.1-6 carboxy or R.sup.1 and R.sup.2 represent the remaining members of a benzene ring;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6- membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl; andR.sup.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: October 11, 1983
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4407815
    Abstract: The present invention provides the compounds of the formula (II): ##STR1## and pharmaceutically acceptable salts and cleavable esters thereof wherein RCONH is an organic acylamino group and E is a carboxy group or pharmaceutically acceptable salt or ester thereof or is a cyano group. Their preparation is described as is their use in compositions containing them. Compounds wherein RCONH is replaced by an azido group are described as useful intermediates.
    Type: Grant
    Filed: February 10, 1981
    Date of Patent: October 4, 1983
    Assignee: Beecham Group Limited
    Inventors: Michael J. Pearson, Clive L. Branch
  • Patent number: 4405637
    Abstract: Compounds are described of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is an ester group; A.sub.1 is a hydrogen atom; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is a hydrogen atom or a hydroxyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; and R.sub.4 is a hydrogen atom or a lower alkyl group, a benzyl group, a phenyl group or is joined to R.sub.3 to form part of a C.sub.5-7 carboxylic ring or is a group of the formula CH(OH)R.sub.5 or CHX wherein R.sub.5 is a hydrogen atom or lower alkyl group and X is an oxygen atom or a CR.sub.6 R.sub.7 group where R.sub.6 is a hydrogen atom or a lower alkyl, phenyl, CN, CO.sub.2 R.sub.8 where R.sub.8 is a lower alkyl, phenyl or benzyl group and R.sub.7 is a hydrogen atom or a lower alkyl group or is joined to R.sub.6 to form part of a C.sub.5-7 carbocyclic ring. These compounds have been found to possess antibacterial properties. The preparation of these compounds is described.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: September 20, 1983
    Assignee: Beecham Group Limited
    Inventors: Kay H. Dickinson nee Berryman, Terence C. Smale, Robert Southgate
  • Patent number: 4405620
    Abstract: Compounds of the formula (I), or pharmaceutically acceptable salts thereof ##STR1## wherein X is phenyl, optionally substituted by one halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; or pyridyl; R.sub.1 is hydrogen or C.sub.1-6 alkyl; and n is 1 to 6, pharmaceutical compositions containing them and a process for their preparation. These compounds are useful in the prophylaxis or treatment of diseases due to a histamine-mediated allergic response.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: September 20, 1983
    Assignee: Beecham Group Limited
    Inventors: Derek R. Buckle, Harry Smith
  • Patent number: 4401674
    Abstract: The stability of an oil intramammary formulation containing a suspension of a moisture sensitive penicillin is improved by incorporation therein of molecular sieve powder.
    Type: Grant
    Filed: December 24, 1981
    Date of Patent: August 30, 1983
    Assignee: Beecham Group Limited
    Inventor: John S. Dowrick