Patents Assigned to Beecham Group Limited
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Patent number: 4378360Abstract: Compounds of formula (I): ##STR1## wherein R is hydrogen, halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; R.sub.1 is hydrogen or C.sub.1-6 alkyl; and n is 1 to 6 and pharmaceutically acceptable salts thereof; pharmaceutical compositions containing them; a process for their preparation; and their use in treating allergy.Type: GrantFiled: April 15, 1981Date of Patent: March 29, 1983Assignee: Beecham Group LimitedInventors: Derek R. Buckle, Harry Smith, John M. Tedder
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Patent number: 4374147Abstract: Compounds of formula (II): ##STR1## in which R represents a pharmaceutically acceptable ester-forming radical have antibacterial and antimycoplasmal activity. These compounds are produced by photo-oxidation of the corresponding 13-hydroxy compounds, optionally after having protected the glycol moiety.Type: GrantFiled: June 5, 1981Date of Patent: February 15, 1983Assignee: Beecham Group LimitedInventors: Kong Luk, Norman H. Rogers
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Patent number: 4374144Abstract: The present invention relates to the preparation of compounds of the formula: ##STR1## wherein CO.sub.2 R.sub.1 is a free, salted or esterified carboxyl group, n is 0 or 1, and R.sub.2 is hydrogen or an acyl group or a group of the sub-formula (a):R.sub.3 O.sub.3 S (a)wherein R.sub.3 is a salting ion or a methyl or ethyl group, with the proviso that when R.sub.2 is a group of the formula (a), the compound has cis stereochemistry about the .alpha.-lactam ring; which have been found to possess antibacterial and .alpha.-lactamase inhibitory activity.Type: GrantFiled: November 3, 1980Date of Patent: February 15, 1983Assignee: Beecham Group LimitedInventor: David F. Corbett
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Patent number: 4372962Abstract: The compounds of the formula (I): ##STR1## and pharmaceutically acceptable salts and in-vivo hydrolysable esters thereof wherein X is a sulphur atom or SO or SO.sub.2 group and R is a hydrogen atom or an alkyl group of 1 to 6 carbon atoms have been found to be .beta.-lactamase inhibitors and antibacterial agents. Their preparation and use is described.Type: GrantFiled: May 13, 1980Date of Patent: February 8, 1983Assignee: Beecham Group LimitedInventors: John S. Davies, Gerald Brooks
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Patent number: 4372946Abstract: 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) 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: GrantFiled: July 9, 1980Date of Patent: February 8, 1983Assignee: Beecham Group LimitedInventors: Thomas T. Howarth, Eric Hunt
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Patent number: 4368334Abstract: A process for the isolation of a solid salt of p-hydroxymandelic acid, which process comprises reacting phenol with glyoxylic acid in the presence of sodium or potassium hydroxide, acidifying to a pH less than 3, extracting the resulting solution with a water-immiscible solvent to provide a solution of p-hydroxymandelic acid and precipitating the salt therefrom.Type: GrantFiled: April 9, 1981Date of Patent: January 11, 1983Assignee: Beecham Group LimitedInventor: John R. M. Dales
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Patent number: 4367338Abstract: Compounds of formula (I) ##STR1## wherein: n is 1 to 5Y is --CH.sub.2 --CH.sub.2 or --CH.dbd.CH--;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 1-12 carbon atoms;R.sub.2 is hydrogen, C.sub.1-4 alkyl, or phenyl;R.sub.3 is hydroxy or protected hydroxy;R.sub.4 is hydrogen, C.sub.1-9 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-6 alkyl, phenyl, phenyl --C.sub.1-6 alkyl, naphthyl, naphthyl C.sub.1-6 alkyl, any of which phenyl moieties or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy, phenyl C.sub.1-6 alkoxy or nitro groups;R.sub.5 is hydrogen, C.sub.1-6 alkyl, C.sub.5-8 cycloalkyl, phenyl, phenyl-C.sub.1-6 alkyl or phenyl C.sub.3-6 cycloalkyl, 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;orR.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.Type: GrantFiled: December 8, 1977Date of Patent: January 4, 1983Assignee: Beecham Group LimitedInventors: David R. Adams, Alexander C. Goudie
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Patent number: 4366167Abstract: This invention provides the anti-bacterial compounds (III) and (IV): ##STR1## and salts and esters thereof wherein X is a --CH.sub.2 --CH.sub.2 -- or trans --CH.dbd.CH-- group and R is a group R.sup.1 or NH.R.sup.1 wherein R.sup.1 is an alkyl group of up to 6 carbon atoms, an alkenyl group of up to 6 carbon atoms, an aryl group, or an alkyl group of up to 6 carbon atoms substituted by an aryl or aryloxy group.The invention also provides processes for their preparation comprising a the acylation or carbamoylation of the corresponding 6-(1-hydroxyethyl) compounds.The invention further provides pharmaceutical compositions containing them.Type: GrantFiled: March 30, 1979Date of Patent: December 28, 1982Assignee: Beecham Group LimitedInventor: David F. Corbett
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Patent number: 4366163Abstract: Compounds of the formula (I) ##STR1## and salts and pro-drugs thereof, wherein: R.sub.1 is a hydrogen atom or a lower alkyl group;R.sub.2 is a hydrogen atom or a lower alkyl group;R.sub.3 is a hydrogen atom or a lower alkyl group;R.sub.4 is a hydrogen atom or an alkyl group;R.sub.5 is a lower alkyl or a substituted alkyl group;or R.sub.4 and R.sub.5 are joined so that together with the nitrogen atom to which they are attached they form a 5-, 6- or 7-membered ring optionally containing an oxygen or sulphur atom;R.sub.6 is an electron donating group;R.sub.7 is an electron withdrawing group; andthe NR.sub.4 R.sub.5 and OR.sub.3 moieties are trans having compositions containing them and processes for their preparation.Type: GrantFiled: September 12, 1980Date of Patent: December 28, 1982Assignee: Beecham Group LimitedInventors: John M. Evans, Graham A. Showell, Charles S. Fake
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Patent number: 4363811Abstract: Compounds of the formula (I): ##STR1## and salts and pro-drugs thereof, wherein: R.sub.1 is a hydrogen atom or a lower alkyl group;R.sub.2 is a hydrogen atom or a lower alkyl group;R.sub.3 is a hydrogen atom or a lower alkyl group;R.sub.4 is a hydrogen atom or an alkyl group;R.sub.5 is a lower alkyl or a substituted alkyl group;or R.sub.4 and R.sub.5 are joined so that together with the nitrogen atom to which they are attached they form a 5-, 6- or 7-membered ring optionally containing an oxygen or sulphur atom;R.sub.6 is an electron donating group;R.sub.7 is an electron withdrawing group; andthe NR.sub.4 R.sub.5 and OR.sub.3 moieties are trans having antihypertensive activity, pharmaceutical compositions containing them and processes for their preparation.Type: GrantFiled: September 12, 1980Date of Patent: December 14, 1982Assignee: Beecham Group LimitedInventors: John M. Evans, Graham A. Showell, Charles S. Fake
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Patent number: 4362880Abstract: An improved process for the preparation of 3-substituted thiophenes. The thiophenes are useful for the preparation of penicillins and cephalosporins.The process is for the preparation of a thiophene of formula (I): ##STR1## where R.sup.1 represents a carboxylic acid group, or an ester or amide thereof or a nitrile group; R.sup.2 represents a group suitable for use as an .alpha.-substituent in the side-chain of a penicillin or cephalosporin; which comprises treating under basic conditions a compound of formula (II): ##STR2## wherein X represents halogen or optionally functionalized hydroxyl, Y represents halogen, hydroxyl, or alkoxy; with a source of nucleophilic sulphur ionically bound to a polymeric support.Type: GrantFiled: March 30, 1981Date of Patent: December 7, 1982Assignee: Beecham Group LimitedInventors: Kenneth T. Veal, Trevor J. Grinter
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Patent number: 4362892Abstract: Certain substituted aralkylanilines in which the aromatic aniline ring carries, at the para position to the amino function, a substituent which comprises a carboxylic acid, salt or ester, an alkyl, hydroxyalkyl, cyano or acyl group, have hypolipidaemic activity.Type: GrantFiled: December 12, 1977Date of Patent: December 7, 1982Assignee: Beecham Group LimitedInventors: Richard M. Hindley, Keith H. Baggaley
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Patent number: 4362743Abstract: Compounds of formula (II): ##STR1## in which Y represents ##STR2## and R.sub.0 represents a C.sub.2-20 alkyl, C.sub.3-8 cycloalkyl, C.sub.4-20 alkenyl, arakyl, cycloalkylalkyl, heterocyclyl or heterocyclylalkyl group, which is substituted by a hydroxyiminohydrazono- or semicarbazono group, have activity against human and veterinary bacteria and mycoplasma. They may be produced by conventional methods and are used in conventional formulations.Type: GrantFiled: July 31, 1981Date of Patent: December 7, 1982Assignee: Beecham Group LimitedInventors: Norman H. Rogers, Peter J. O'Hanlon, Graham Walker
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Patent number: 4359473Abstract: 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.Type: GrantFiled: September 4, 1979Date of Patent: November 16, 1982Assignee: Beecham Group LimitedInventors: Irene Stirling, Brian P. Clarke
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Patent number: 4359423Abstract: A compound of formula (II): ##STR1## wherein R is a C.sub.1-4 alkyl group;R.sub.1 is a hydrogen atom or a C.sub.1-4 alkyl group;R.sub.2 is a hydrogen or halogen atom, or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.1-4 alkylthio group;and pro-drugs thereof; and the pharmaceutically acceptable salts of the compounds of formula (II) and of their pro-drugs; has useful anti-inflammatory and analgesic activity.Type: GrantFiled: July 25, 1980Date of Patent: November 16, 1982Assignee: Beecham Group LimitedInventors: Alexander C. Goudie, Robert W. Ward
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Patent number: 4358437Abstract: A toothpaste contains 2% by weight of calcium metasilicate, 0.80% of sodium monofluorophosphate and 44.77% calcium carbonate. The presence of calcium metasilicate in combination with the monofluorophosphate and carbonate increases the fluoride uptake over and above that which is expected from the level of free fluoride present.Type: GrantFiled: April 13, 1981Date of Patent: November 9, 1982Assignee: Beecham Group LimitedInventor: Susan A. Duke
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Patent number: 4355004Abstract: A compound with hypoglycaemic activity having formula (II) or a pharmaceutically acceptable ammonium or acid addition salt thereof: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy or halogen;R.sup.3 and R.sup.4 are the same or different and represent hydrogen or C.sub.1-6 alkyl;R.sup.5 represents hydrogen or C.sub.1-6 alkyl;R.sup.6 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.5 and R.sup.6 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, carboxy or C.sub.1-6 alkoxycarbonyl; andR.sup.7 represents phenyl, optionally substituted with up to 3 groups selected from halogen, C.sub.Type: GrantFiled: October 23, 1980Date of Patent: October 19, 1982Assignee: Beecham Group LimitedInventors: Barrie C. C. Cantello, Susan M. White
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Patent number: 4354974Abstract: Esters of the compound of the formula: ##STR1## are useful for their antibacterial and .beta.-lactamase inhibitory activity.Type: GrantFiled: December 6, 1976Date of Patent: October 19, 1982Assignee: Beecham Group LimitedInventor: Irene Stirling
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Patent number: 4353906Abstract: Compounds of the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2 are independently selected from a hydrogen atom and a C.sub.1-3 alkyl group;R.sub.3 is a hydrogen atom, a C.sub.1-3 alkyl or C.sub.2-4 acyl group;R.sub.4 is a hydrogen atom or C.sub.1-5 alkyl group;R.sub.5 is a C.sub.1-5 alkyl group, a straight chain C.sub.1-3 alkyl group terminally substituted by a chlorine atom; orR.sub.4 and R.sub.5 are joined so that together with the nitrogen atom to which they are attached they form a 5-, 6- or 7-membered ring optionally containing an oxygen or sulphur atom;R.sub.6 is a C.sub.1-5 alkyl group;the NR.sub.4 R.sub.5 and OR.sub.3 moieties are trans; and pharmaceutically acceptable salts thereof having antihypertensive activity, processes for their preparation and their use in compositions.Type: GrantFiled: February 2, 1981Date of Patent: October 12, 1982Assignee: Beecham Group LimitedInventor: Graham A. Showell
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Patent number: 4352802Abstract: Compounds of the formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: X is oxygen or sulphur;R.sub.1 is a C.sub.1-6 alkoxy or C.sub.1-6 alkylthio 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 or amino, aminocarbonyl or aminosulphonyl optionally substituted by one or two C.sub.1-6 alkyl groups, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, hydroxy or nitro or R.sub.1 and R.sub.2 taken together are methylenedioxy or ethylenedioxy in which case R.sub.3 is any one of the groups given for R.sub.2 and R.sub.3 above;R.sub.4 is C.sub.1-7 alkyl or a group --(CH.sub.2).sub.s R.sub.5 where s is 0 to 2 and R.sub.5 is a C.sub.3-8 cycloalkyl group, or a group --(CH.sub.2).sub.t R.sub.6 where t is 1 or 2 and R.sub.6 is a phenyl group optionally substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.Type: GrantFiled: June 1, 1981Date of Patent: October 5, 1982Assignee: Beecham Group LimitedInventor: Frank E. Blaney