Patents by Inventor Bernard J. McLoughlin
Bernard J. McLoughlin has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5574037Abstract: This invention concerns novel compounds of the formula I: ##STR1## in which P is a group of formula II or a group of formula III; R.sup.1 is alkyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl; R.sup.2 is hydrogen, alkyl, amino or alkylamino; R.sup.3 and R.sup.4 are independently hydrogen, alkyl, phenyl or benzyl; R.sup.6 is alkyl, amino or alkylamino; C and D are independently ethylene or trimethylene; Z is a direct bond between C and D, or an oxy, thio, carbonyl, methylene, ethylenedioxymethylene, ethylidene, or isopropylidene link, or Z is a group of the formula .dbd.N.R.sup.5 in which R.sup.5 is alkyl, phenyl or benzyl; R8 is hydrogen, cycloalkylalkyl, alkyl, alkenyl, alkynyl or phenylalkyl; or R8 is a alkylene or alkenylene linked to the nitrogen atom of the group Q.A.Type: GrantFiled: June 7, 1995Date of Patent: November 12, 1996Assignee: Imperial Chemical Industries PLCInventors: Stuart D. Mills, Rodney B. Hargreaves, Bernard J. McLoughlin
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Patent number: 5332737Abstract: This invention concerns novel compounds of the formula I: ##STR1## in which P is a group of formula II or a group of formula III; R.sup.1 is alkyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl; R.sup.2 is hydrogen, alkyl, amino or alkylamino; R.sup.3 and R.sup.4 are independently hydrogen, alkyl, phenyl or benzyl; R.sup.6 is alkyl amino or alkylamino; C and D are independently ethylene or trimethylene; Z is a direct bond between C and D, or an oxy, thio, carbonyl, methylene, ethylenedioxymethylene, ethylidene, or isopropylidene link, or Z is a group of the formula .dbd.N.R.sup.5 in which R.sup.5 is alkyl, phenyl or benzyl; R8 is hydrogen, cycloalkylalkyl, alkyl, alkenyl, alkynyl or phenylalkyl; or R8 is a alkylene or alkenylene linked to the nitrogen atom of the group Q.A.Type: GrantFiled: December 3, 1990Date of Patent: July 26, 1994Assignee: Imperial Chemical Industries PLCInventors: Stuart D. Mills, Rodney B. Hargreaves, Bernard J. McLoughlin
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Patent number: 5252567Abstract: This invention concerns compounds of the formula I: ##STR1## wherein R.sup.1 is (1-10C)alkyl, (3-8C)cycloalkyl, (3-8C)cycloalkyl-(1-4C)-alkyl, phenyl or phenyl(1-4C)alkyl, the phenyl moiety of the latter two optionally bearing one or more substituents; R.sup.2 is hydrogen, (1-4C)alkyl, amino or (1-4C)alkylamino; R.sup.6 is (1-4C)alkyl, amino or (1-4C)alkylamino; Q is a group of formula II, in which case R.sup.3 and R.sup.4 are independently hydrogen, (1-4C)alkyl, phenyl or benzyl the phenyl moiety of the latter two optionally bearing one or two substituents; R.sup.5 is hydrogen, (1-4C)alkyl or (2-4C)alkenyl; A and B are independently ethylene or trimethylene; Z is a direct bond between A and B, or an oxy, thio, carbonyl, methylene, ethylenedioxymethylene, ethylidene, or isopropylidene link, or Z is a group of the formula .dbd.N.Type: GrantFiled: December 18, 1990Date of Patent: October 12, 1993Assignee: Imperial Chemical Industries PLCInventors: Stuart D. Mills, Rodney B. Hargreaves, Bernard J. McLoughlin
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Patent number: 5223505Abstract: This invention concerns novel aminopyrimidinium salts of the formula I: ##STR1## in which R.sup.1 is alkyl, alkenyl, cycloalkyl, phenyl, phenylalkyl or cycloalkyl-alkyl; one of R.sup.2 and R.sup.6 is a basic group selected from amino, alkylamino, dialkylamino of up to eight carbon atoms, pyrrolidino, piperidino and morpholino; and the other of R.sup.2 and R.sup.6 is hydrogen, alkyl, alkenyl, alkoxyalkyl, phenyl, phenylalkyl, cycloalkyl or cycloalkyl-alkyl; or both of R.sup.2 and R.sup.6 are basic groups as mentioned above; and R.sup.5 is hydrogen, (1-4C)alkyl or (3-6C)alkenyl; or R.sup.2 is a basic group as mentioned above, and R.sup.5 and R.sup.6 together form alkylene or, together with the appendant carbon atoms of the pyrimidine ring, complete a benzene ring; R.sup.4 is hydrogen, alkyl, cycloalkyl-alkyl, alkenyl, alkynyl or phenylalkyl; or R.sup.4 is an optionally substitutued alkylene or alkenylene linked to the nitrogen atom of the group Q.A.Type: GrantFiled: April 20, 1990Date of Patent: June 29, 1993Assignee: Imperial Chemical Industries PlcInventors: Rodney B. Hargreaves, Paul W. Marshall, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4873254Abstract: A dihydropyridine of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each is alkyl, alkenyl or alkoxyalkyl, wherein R.sup.3 and R.sup.4 each is alkyl, wherein benzene ring A is unsubstituted or bears one or more additional substituents selected from halogeno, cyano, nitro, trifluoromethyl and alkyl, or bears the substituent .dbd.N--O--N.dbd. attached to the 5- and 6-positions, wherein Ar is as defined in the specification, wherein p is 0 or 1, wherein X is --O-- or --S--, and wherein Y is straight-or branched-chain alkylene or alkenylene each of 2 to 12 carbon atoms which may optionally be interrupted by one or two groups selected from oxygen, sulphur, imino, substituted imino, phenylene, substituted phenylene, pyridylene, cycloalkylene, 1,4-piperazinediyl, 1,4-piperidinediyl and amido groups; or an acid-addition salt thereof, processes for their manufacture and pharmaceutical compositions containing them.Type: GrantFiled: February 11, 1986Date of Patent: October 10, 1989Assignee: Imperial Chemical Industries plcInventors: Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4788194Abstract: Heterocyclic compounds of the formula ##STR1## wherein A is a direct link, or is alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms; wherein either X is --CR.sup.1 R.sup.2 -- and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms; or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -wherein R.sup.1 and R.sup.2 have the meanings stated above; and wherein Het is a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from nitrogen, oxygen or sulphur atoms, which ring may be unsubstituted or may bear one or two substituents as set out in claim 1, provided that when X is --CR.sup.1 R.sup.2 and A is a direct link, Het is not unsubstituted 2-furyl; and salts thereof where appropriate; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.Type: GrantFiled: September 14, 1987Date of Patent: November 29, 1988Assignee: Imperial Chemical Industries PLCInventors: Rodney B Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4716164Abstract: Heterocyclic compounds of the formula: ##STR1## wherein A is a direct link, or is alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms; wherein either X is --CR.sup.1 R.sup.2 -- and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms; or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above; and wherein Het is a 5- or 5- membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from nitrogen, oxygen or sulphur atoms, which ring may be unsubstituted or may bear one or two substituents as set out in claim 1, provided that when X is --CR.sup.1 R.sup.2 -- and A is a direct link, Het is not unsubstituted 2-furyl; and salts thereof where appropriate; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.Type: GrantFiled: October 31, 1985Date of Patent: December 29, 1987Assignee: Imperial Chemical Industries PLCInventors: Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4694005Abstract: Heterocyclic compounds of the formula ##STR1## wherein either X is --CR.sup.1 R.sup.2 and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above;wherein either R.sup.4 is hydrogen, fluoro or chloro, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atom, and R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, each is hydrogen, fluoro, chloro, bromo or iodo, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atoms, provided that R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 is bromo and R.sup.5, R.sup.6 and R.sup.7 have the meanings stated above, provided that R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 and R.sup.Type: GrantFiled: April 22, 1986Date of Patent: September 15, 1987Assignee: Imperial Chemical Industries PLCInventors: David Brown, Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4584298Abstract: Heterocyclic compounds of the formula ##STR1## wherein either X is --CR.sup.1 R.sup.2 and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above;wherein either R.sup.4 is hydrogen, fluoro or chloro, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atoms, and R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, each is hydrogen, fluoro, chloro, bromo or iodo, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atoms, provided that R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 is bromo and R.sup.5, R.sup.6 and R.sup.7 have the meanings stated above, provided that R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 and R.sup.Type: GrantFiled: October 12, 1984Date of Patent: April 22, 1986Assignee: Imperial Chemical Industries PLCInventors: David Brown, Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4558045Abstract: Heterocyclic compounds of the formula: ##STR1## wherein A is a direct link, or is alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms; wherein either X is --CR.sup.1 R.sup.2 -- and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above;and wherein Het is a 5- or 6- membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from nitrogen, oxygen or sulphur atoms, which ring may be unsubstituted or may bear one or two substituents as set out in claim 1, provided that when X is --CR.sup.1 R.sup.2 -- and A is a direct link, Het is not unsubstituted 2-furyl; and salts thereof where appropriate; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.Type: GrantFiled: October 12, 1984Date of Patent: December 10, 1985Assignee: Imperial Chemical Industries, PLCInventors: Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4495185Abstract: Heterocyclic compounds of the formula ##STR1## wherein either X is --CR.sup.1 R.sup.2 and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above;wherein either R.sup.4 is hydrogen, fluoro or chloro, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atoms, and R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, each is hydrogen, fluoro, chloro, bromo or iodo, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atoms, provided that R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 is bromo and R.sup.5, R.sup.6 and R.sup.7 have the meanings stated above, provided that R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 and R.sup.Type: GrantFiled: October 26, 1982Date of Patent: January 22, 1985Assignee: Imperial Chemical Industries, PLCInventors: David Brown, Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4493835Abstract: Heterocyclic compounds of the formula: ##STR1## wherein either X is --CR.sup.1 R.sup.2 -- and Y is --O--, --S-- or--NHR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above; wherein R.sup.4 and R.sup.5, which may be the same or different, each is hydrogen (but provided that R.sup.4 and R.sup.5 are not both hydrogen), or each is a group defined in claim 1 which is readily convertible into a carboxy group; processes for their manufacture; and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.Type: GrantFiled: October 26, 1982Date of Patent: January 15, 1985Assignee: Imperial Chemical Industries PLCInventors: Rodney B. Hargreaves, Bernard J. McLoughlin
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Patent number: 4489074Abstract: Heterocyclic compounds of the formula ##STR1## wherein either X is --CR.sup.1 R.sup.2 and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above;wherein either R.sup.4 is hydrogen, fluoro or chloro, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atom, and R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, each is hydrogen, fluoro, chloro, bromo or iodo, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atoms, provided that R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 is bromo and R.sup.5, R.sup.6 and R.sup.7 have the meanings stated above, provided that R.sup.5, R.sup.6 and R.sup.7 are not all hydrogen;or R.sup.4 and R.sup.Type: GrantFiled: November 12, 1982Date of Patent: December 18, 1984Assignee: Imperial Chemical Industries, PLCInventors: David Brown, Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4489073Abstract: Heterocyclic compounds of the formula: ##STR1## wherein A is a direct link, or is alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms; wherein either X is --CR.sup.1 R.sup.2 -- and Y is --O--, --S-- or --NR.sup.3 --, wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms;or X is --O--, --S-- or --NH-- and Y is --CR.sup.1 R.sup.2 -- wherein R.sup.1 and R.sup.2 have the meanings stated above;and wherein Het is a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from nitrogen, oxygen or sulphur atoms, which ring may be unsubstituted or may bear one or two substituents as set out in claim 1, provided that when X is --CR.sup.1 R.sup.2 -- and A is a direct link, Het is not unsubstituted 2-furyl; and salts thereof where appropriate; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.Type: GrantFiled: November 3, 1982Date of Patent: December 18, 1984Assignee: Imperial Chemical Industries, PLCInventors: Rodney B. Hargreaves, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 4124709Abstract: A method of producing anorexia in warm-blooded animals which comprises administering racemic 2-(.beta.-phenyl-trans-vinyl)morpholine or the (2R) isomer thereof.Type: GrantFiled: July 14, 1977Date of Patent: November 7, 1978Assignee: Imperial Chemical Industries LimitedInventors: Bernard J. McLoughlin, Allen J. Guildford
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Patent number: 4088814Abstract: Morpholine derivatives, typically those of the formula: ##STR1## wherein A is an ethylene or vinylene radical and X is a phenyl radical optionally substituted by one or two substituents selected from halogen atoms, alkyl and alkoxy radicals of 1 to 6 carbon atoms and aryloxy radicals of 1 to 6 carbon atoms, the aryloxy radicals themselves being optionally substituted by one or two substituents selected from halogen atoms and alkyl radicals of 1 to 4 carbon atoms, and the pharmaceutically-acceptable acid-addition salts thereof. Processes for making these compounds, pharmaceutical compositions containing them and a method of restoring to normal abnormal mental states in warm-blooded animals are also disclosed.Type: GrantFiled: October 22, 1976Date of Patent: May 9, 1978Assignee: Imperial Chemical Industries LimitedInventors: Bernard J. McLoughlin, Allen J. Guildford