Patents Assigned to Beecham Group p.l.c.
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Patent number: 4539319Abstract: Compounds of formula (I) ##STR1## and acid addition salts thereof, whereinR.sup.1 is hydrogen, hydroxy, alkoxy, aryloxy, aralkoxy, heteroaryloxy or heteroaralkoxy;andone of R.sup.2, R.sup.3 and R.sup.4 is hydrogen and the others are the same or different and each is hydrogen, alkyl, aryl, aralkyl, heteroaryl or heteroaralkyl;orR.sup.2 is hydrogen and ##STR2## is mono- or bi-cyclic amino, inhibit enterotoxin-induced secretion into the small intestine and are, therefore, useful in treating enterotoxin induced diarrhoea in humans and scours in animals.Type: GrantFiled: June 14, 1983Date of Patent: September 3, 1985Assignee: Beecham Group p.l.c.Inventors: Peter M. Newsome, Noel A. Mullan, John P. Marshall
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Patent number: 4539202Abstract: 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.Type: GrantFiled: March 24, 1983Date of Patent: September 3, 1985Assignee: Beecham Group p.l.c.Inventors: Brian P. Clarke, John B. Harbridge, Irene Stirling
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Patent number: 4539149Abstract: .beta.-Lactam antibiotics having an .alpha.-formamido substituent on the carbon atom adjacent to the carbonyl group of the .beta.-lactam ring and in particular bicyclic compounds having the partial structure: ##STR1## Intermediates and processes for the preparation of the compounds are further disclosed.Type: GrantFiled: July 23, 1982Date of Patent: September 3, 1985Assignee: Beecham Group p.l.c.Inventor: Peter H. Milner
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Patent number: 4537886Abstract: A compound of formula (1) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof: ##STR1## wherein R.sup.1 is phenyl, substituted 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;X represents; ##STR2## wherein R.sup.Y is methyl or acetyl; R.sup.2 and R.sup.3 may be the same or different and each is hydrogen, an aryl group, a heterocyclyl group or a C.sub.1-6 alkyl group optionally substituted by an aryl group or a heterocyclyl group; and R.sup.4 is hydrogen, a C.sub.1-6 alkylcarbonyl group, an aryl group, a heterocyclyl group, a C.sub.1-6 alkyl group optionally substituted by an aryl group or a heterocyclyl group;R.sup.5 represents, hydrogen, methoxy or --NHCHO; and Y is: ##STR3## wherein Y.sup.1 is oxygen, sulphur or --CH.sub.2 -- and Z represents hydrogen, halogen or an organic group such as C.sub.1-4 alkoxy, --CH.sub.2 Q or --CH.dbd.Type: GrantFiled: March 29, 1983Date of Patent: August 27, 1985Assignee: Beecham Group p.l.c.Inventors: Andrew W. Taylor, Richard T. Cook
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Patent number: 4533498Abstract: Compounds of formula (I), pharmaceutically acceptable salts, quaternary derivatives and N-oxides thereof, and pharmaceutically acceptable solvates of any of the foregoing: ##STR1## wherein p is 1 to 3;B is C.sub.1-7 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-2 alkyl, or a group (CH.sub.2).sub.t R.sub.11 where t is 1 or 2 and R.sub.11 is thienyl or furyl optionally substituted or is phenyl optionally substituted; and(i) A is a group of formula (II): ##STR2## in which either (a) one of X and Y is CO and the other is NH; or X is CO and Y is NR.sub.6 ; and or(b) one of X and Y is CO and the other is NH; or(ii) A is a group of formula (III): ##STR3## in which one of X and Y is CO and the other is NH, having useful pharmacological properties, pharmaceutical compositions containing them, a process and intermediates for their preparation, and the use of the compounds.Type: GrantFiled: January 26, 1984Date of Patent: August 6, 1985Assignee: Beecham Group p.l.c.Inventors: Francis E. Blaney, Michael S. Hadley, Francis D. King, Eric A. Watts
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Patent number: 4529720Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulonic acid has the formula (I): ##STR1## In addition to being a broad spectrum antibiotic of medium potancy, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of .beta. lactam antibiotics against many .beta.-lactamase producing bacteria.Type: GrantFiled: September 24, 1981Date of Patent: July 16, 1985Assignee: Beecham Group, p.l.c.Inventors: Martin Cole, Thomas T. Howarth, Christopher Reading
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Patent number: 4526783Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulanic acid has the formula (I): ##STR1## In addition to being a broad spectrum antibiotic of medium potency, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria.Type: GrantFiled: June 9, 1981Date of Patent: July 2, 1985Assignee: Beecham Group p.l.c.Inventors: Martin Cole, Thomas T. Howarth, Christopher Reading
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Patent number: 4525353Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulanic acid has the formula (I): ##STR1## In addition to being a broad spectrum antibiotic of medium potency, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria.Type: GrantFiled: February 26, 1982Date of Patent: June 25, 1985Assignee: Beecham Group p.l.c.Inventors: Martin Cole, Thomas T. Howarth, Christopher Reading
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Patent number: 4525352Abstract: A new antibacterially active agent has been isolated from Streptomyces clavuligerus. This new compound which is designated clavulanic acid has the formula (I): ##STR1## In addition to being a broad spectrum antibiotic of medium potency, clavulanic acid and its salts and esters have the ability to enhance the effectiveness of .beta. lactam antibotics against many .beta.-lactamase producing bacteria.Type: GrantFiled: December 3, 1981Date of Patent: June 25, 1985Assignee: Beecham Group p.l.c.Inventors: Martin Cole, Thomas T. Howarth, Christopher Reading
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Patent number: 4524075Abstract: Topical formulations comprise pseudomonic acid or a salt or ester thereof and a polyethylene glycol or polyethylene glycol analogue or derivative.Type: GrantFiled: May 26, 1983Date of Patent: June 18, 1985Assignee: Beecham Group p.l.c.Inventor: Joshua Oduro-Yeboah
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Patent number: 4521337Abstract: A process for the preparation of a compound of the formulae (Ia) and/or (Ib): ##STR1## wherein R.sup.1 and R.sup.2 are independently substituted or unsubstituted hydrocarbon groups or are joined together so as to form a carbocyclic or heterocyclic ring, and R.sup.3 is a substituted or unsubstituted hydrocarbon group; which process comprises the ring-closing cyclization of a compound of the formula (II): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in relation to formulae (Ia) and (Ib).Type: GrantFiled: March 14, 1983Date of Patent: June 4, 1985Assignee: Beecham Group p.l.c.Inventors: Robert Southgate, Pamela Brown
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Patent number: 4520014Abstract: Vasoconstrictor .alpha.-adrenergic agonists of formula (I)A-B-C (I)wherein, A is a 2-imidazoline group or a guanidine group; B is a chemical bond or a linking group one or two atoms in length; and C is a C.sub.6-10 mono- or bi-cyclic group which is either an aromatic group, a heteroaromatic group containing only one hetero-atom, or a group containing an aromatic moiety; and which group C may be substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or hydroxyl; or salts thereof, are useful in the treatment and prevention of diarrhoea in livestock. Compositions of these compounds are described.Type: GrantFiled: February 19, 1982Date of Patent: May 28, 1985Assignee: Beecham Group p.l.c.Inventors: Peter M. Newsome, Noel A. Mullan
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Patent number: 4510152Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.Type: GrantFiled: April 21, 1983Date of Patent: April 9, 1985Assignee: Beecham Group p.l.c.Inventor: Erol A. Faruk
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Patent number: 4507283Abstract: A derivative of streptokinase-human plasminogen activator complex, in which the active catalytic site essential for fibrinolytic activity is blocked by a 2- or 4-aminobenzoyl group, is useful in treating venous thrombosis.The blocking group is removable by hydrolysis such that the first order rate is in the range 0.7.times.10.sup.-5 sec.sup.-1 to 2.5.times.10.sup.-5 sec.sup.-1 in isotonic aqueous media at pH 7.4 at 37.degree. C.Type: GrantFiled: April 5, 1983Date of Patent: March 26, 1985Assignee: Beecham Group p.l.c.Inventor: Richard A. G. Smith
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Patent number: 4505926Abstract: Compounds of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is selected from halogen, alkyl, haloalkyl, alkoxy and alkoxyalkyl,R.sup.3, R.sup.4 and R.sup.5 are the same or different and each is alkyl;n is 0,1,2 or 3; andZ is a pharmaceutically or veterinarily acceptable anion, protect animals from death due to enteropathogenic E. coli infection of the gastro-intestinal tract.Type: GrantFiled: September 15, 1983Date of Patent: March 19, 1985Assignee: Beecham Group p.l.c.Inventors: Peter M. Newsome, Stephen F. Moss, Lee J. Beeley, Malcolm N. Burgess
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Patent number: 4504480Abstract: Compounds of formula (I), ##STR1## or an N-oxide or pharmaceutically acceptable salt thereof, wherein R.sub.1 is hydrogen, C.sub.1-7 alkyl, C.sub.3-7 cycloalkyl, C.sub.4-7 cycloalkenyl or C.sub.1-4 alkyl substituted by C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, C.sub.3-7 cycloalkyl, hydroxy, thiol, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, carboxy, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkanoyl, amino optionally substituted by one or two C.sub.1-4 alkyl or by C.sub.4-6 polymethylene optionally containing an oxygen or nitrogen atom, aminocarbonyl optionally N-substituted by one or two C.sub.1-4 alkyl, or benzoyl or phenyl either being optionally ring-substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or trifluoromethyl, R.sub.2 and R.sub.3 are the same or different and are hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alklthio, halogen or trifluoromethyl, m is 1 to 3 and n is 1 or 2, the hydrogen atom bonded to the C.sub.a carbon atom being trans to the hydrogen atom bonded to the C.sub.Type: GrantFiled: March 4, 1983Date of Patent: March 12, 1985Assignee: Beecham Group p.l.c.Inventors: Laramie M. Gaster, Barry S. Orlek
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Patent number: 4501696Abstract: A process for the preparation of a penam derivative of formula (I): ##STR1## wherein R.sup.A is hydrogen or a group of formula (Ia): ##STR2## wherein X is --CO.sub.2 R.sup.1, or SO.sub.3 R.sup.1 ; R is C.sub.1-6 alkyl, aryl, or heterocyclyl; R.sup.1 is hydrogen, or a pharmaceutically acceptable salt-forming ion or ester-forming radical, and R.sup.2 represents hydrogen or a pharmaceutically acceptable salt-forming ion or in vivo hydrolyzable ester-forming radical; which process comprises reacting a compound of formula (II): ##STR3## wherein R.sup.B is hydrogen, a removable amino blocking group, or a group of formula (IIa): ##STR4## wherein Y is --CO.sub.2 R.sup.x or --SO.sub.3 R.sup.x ; R is as defined with respect to formula (I) above; R.sup.x represents an ester-forming radical, R.sup.Y represents hydrogen, a salt-forming radical or a carboxyl-blocking group, and R.sup.Type: GrantFiled: July 9, 1982Date of Patent: February 26, 1985Assignee: Beecham Group p.l.c.Inventors: John R. M. Dales, Marguerita A. Vallance
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Patent number: 4499099Abstract: Pharmaceutical compositions comprising compounds of formula (I) or pharmaceutically acceptable salts and/or N-oxides and/or solvates thereof: ##STR1## wherein: R.sub.1 is a C.sub.1-6 alkoxy or C.sub.1-6 alkylthio group; andone of R.sub.2, R.sub.3 and R.sub.4 is hydrogen, the second is C.sub.1-6 alkylthio and the third is selected from the class of substituents consisting of hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-7 acyl, C.sub.1-7 acylamino, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkylsulphinyl, hydroxy, nitro or amino, aminocarbonyl or aminosulphonyl optionally N-substituted by one or two C.sub.1-6 alkyl groups; orR.sub.1 is joined to R.sub.2 to form C.sub.1-2 alkylenedioxy; andone of R.sub.3 and R.sub.4 is C.sub.1-6 alkylthio and the other is selected from the class of substituents defined above;R.sub.5 is hydrogen or C.sub.1-6 alkyl;R.sub.6 is C.sub.1-7 alkyl or a group --(CH.sub.2).sub.s R.sub.7 where s is 0 to 2 and R.sub.7 is a C.sub.Type: GrantFiled: June 9, 1982Date of Patent: February 12, 1985Assignee: Beecham Group p.l.c.Inventor: Eric A. Watts
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Patent number: 4496565Abstract: Compounds of formula (I): ##STR1## a pharmaceutically acceptable salt or solvate thereof having anti-hypertensive activity, a process for their preparation and their use as pharmaceuticals.Type: GrantFiled: October 17, 1983Date of Patent: January 29, 1985Assignee: Beecham Group p.l.c.Inventors: John M. Evans, Valerie A. Ashwood
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Patent number: 4490294Abstract: 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: GrantFiled: March 20, 1978Date of Patent: December 25, 1984Assignee: Beecham Group p.l.c.Inventors: Ian D. Fleming, David Noble, Hazel M. Noble, Wilfred F. Wall