Nitrogen, Other Than As Nitro Or Nitroso, Attached Indirectly To The Quinoline Ring System By Nonionic Bonding Patents (Class 546/176)
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Patent number: 5290788Abstract: Alkoxy substituted indole derivatives as inhibitors of lipoxygenase and useful as antiallergy and antiinflammatory agents.Type: GrantFiled: April 21, 1992Date of Patent: March 1, 1994Assignee: Pfizer Inc.Inventors: Rodney W. Stevens, Hiromasa Morita, Masami Nakane
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Patent number: 5288749Abstract: The present invention provides tertiary and secondary amine compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof which are antagonists for alpha-2 adrenoreceptors and which inhibit serotonin (5-hydroxytryptamine, 5-HT) uptake.Type: GrantFiled: December 20, 1991Date of Patent: February 22, 1994Assignee: Abbott LaboratoriesInventors: Michael D. Meyer, John F. DeBernardis, Rajnandan Prasad, Kevin B. Sippy, Karin R. Tietje
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Patent number: 5283245Abstract: The invention concerns a thiazole of the formula I, ##STR1## wherein Q.sup.1 is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents, or Ar is an optionally substituted 6-membered heterocyclene moiety contining up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl;R.sup.2 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl or substituted (1-4C)alkyl or R.sup.2 is optionally substituted benzoyl; andQ.sup.2 is optionally substituted thiazolyl;or a pharmaceutically-acceptable salt thereof.The invention also concerns processes for the manufacture of a thiazole of the formula I and pharmaceutical compositions containing said thiazole.Type: GrantFiled: November 18, 1991Date of Patent: February 1, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Martin P. Edwards
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Patent number: 5281613Abstract: The invention concerns pharmaceutically useful compounds of the formula I, in which Q, X, G.sup.1, Z and Ra have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.Type: GrantFiled: June 25, 1992Date of Patent: January 25, 1994Assignee: Imperial Chemical Industries PLCInventors: Robert H. Bradbury, Andrew P. Thomas
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Patent number: 5281593Abstract: A compound of the formula ##STR1## in which R.sup.1 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C.sub.1-4 alkyl, aldehydo, --CH.sub.2 Z, --CH.dbd.CH--Z or --CH.sub.2 CH.sub.2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R.sup.2 is halo, nitrile, an optionally protected acid group or --CONR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 are each hydrogen or C.sub.1-4 alkyl; R.sup.3 and R.sup.4 are each hydrogen, C.sub.1-4 alkyl, optionally substituted phenyl, or C.sub.1-4 alkyl substituted by --CONR.sup.7 R.sup.8 or an optionally protected acid group; R.sup.5 is ##STR2## where W is --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --O-- or --S--, R.sup.9 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or trihalomethyl, and R.sup.10 is hydrogen, C.sub.1-4 alkyl, C.sub.2-6 alkenyl, C.sub.3-6 cycloalkyl or C.sub.1-4 alkyl-C.sub.3-6 cycloalkyl; R.sup.6 is hydrogen or C.sub.Type: GrantFiled: April 29, 1993Date of Patent: January 25, 1994Assignee: Lilly Industries LimitedInventors: Jeremy Gilmore, Alec Todd
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Patent number: 5274096Abstract: An improved synthesis is described for producing a quinolinylmethoxyphenyl hydrazine which is an intermediate in the preparation of quinolinylmethoxyindoles useful as inhibitors of leukotriene biosynthesis. The improved process eliminates two isolation steps and yields a product of high purity.Type: GrantFiled: March 17, 1992Date of Patent: December 28, 1993Assignee: Merck & Co., Inc.Inventors: Joseph F. Payack, Dalian Zhao
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Patent number: 5272156Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O or NR'; where R' is hydrogen or lower alkyl; R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl; R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen, A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; n is 0-5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or aketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 were m is 0-4, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 28, 1992Date of Patent: December 21, 1993Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5268380Abstract: (1H-azol-1-ylmethyl)substituted quinoline derivatives, compositions containing the same, and methods of treating mammals suffering from disorders which are characterized by an increased proliferation and/or abnormal differentiation of epithelial tissues.Type: GrantFiled: November 10, 1992Date of Patent: December 7, 1993Assignee: Janssen Pharmaceutica N.V.Inventors: Gerard C. Sanz, Marc G. Venet, Eddy J. E. Freyne, Alfons H. M. Raeymakers
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Patent number: 5266572Abstract: There are provided cycloalkyl piperidine compounds which are useful in the treatment of physiological or drug-induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.Type: GrantFiled: June 18, 1992Date of Patent: November 30, 1993Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Gary A. Cain, Paul J. Gilligan, Sang W. Tam
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Patent number: 5256661Abstract: Certain novel compounds having the structural formula ##STR1## where R.sub.2, R.sub.3 and R.sub.4 are each selected from the group consisting of H and OA; A is H or is selected from the group consisting of hydrocarbyl radicals, e.g. lower alkyl radicals, i.e. methyl, ethyl, propyl, etc., or ##STR2## wherein R.sub.5 is selected from the group consisting of hydrocarbyl radicals, e.g. alkyl and aromatic residues; n is 2 or 3; and R.sub.1 is selected from the group consisting of organic radicals having fused aromatic rings, that is, radicals comprising at least two rings that share a pair of carbon atoms or share a carbon and nitrogen atom are useful for inducing a dopaminergic response and reducing the intraocular pressure in a mammal.Type: GrantFiled: September 28, 1992Date of Patent: October 26, 1993Assignee: Whitby Research, Inc.Inventor: Alan S. Horn
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Patent number: 5254595Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.Type: GrantFiled: January 9, 1992Date of Patent: October 19, 1993Assignee: Elf SanofiInventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
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Patent number: 5246958Abstract: Disclosed are antihypertensive pharmaceutical compositions and compounds which include the thiocarbamoylacetonitrile having the formula: ##STR1## wherein: R.sup.1 is selected from the group consisting of hydrogen, a C.sub.1 to C.sub.6 alkyl, a C.sub.3 to C.sub.6 cycloalkyl or --(CH.sub.2).sub.n --A (where A is selected from the group consisting of a C.sub.6 to C.sub.12 aryl, a 5- or 6-membered heterocyclic group or a fused heterocyclic group constituted by 9 or 10 atoms, each of which may be substituted by at least one substitute group selected from a C.sub.1 to C.sub.6 alkyl and a halogen and n is 0 or an integer of 1 to 6),R.sup.2 represents a C.sub.1 to C.sub.10 alkyl, and Ar represents an aryl, a 5- or 6-membered heterocyclic group or a fused heterocyclic group, each of which may be substituted by at least one substituent group selected from the group consisting of a C.sub.1 to C.sub.6 alkyl, a C.sub.1 to C.sub.6 alkoxy, a C.sub.2 to C.sub.7 alkylcarbonyl, a C.sub.7 to C.sub.Type: GrantFiled: March 4, 1991Date of Patent: September 21, 1993Assignee: Mitsubishi Kasei CorporationInventors: Hiromi Okushima, Akihiro Tobe, Makio Kobayashi, Tetsuro Shimpuku, Hideki Bessho, Junko Hayashi, Asami Seino
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Patent number: 5243048Abstract: There are provided cycloalkyl piperidine compounds which are useful in the treatment of physiological or drug-induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.Type: GrantFiled: February 6, 1992Date of Patent: September 7, 1993Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Gary A. Cain, Paul J. Gilligan, Sang W. Tam
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Patent number: 5240942Abstract: The invention relates to compounds of formula I: ##STR1## in which R.sub.1 represents a naphthyl radical, a dihydronaphthyl radical, a tetrahydronaphthyl radical, a quinolyl radical or a 1,4-benzodioxanyl radical, A represents a single bond, a double bond, a methylene radical, a radical of formula z.sub.1 :--CH.dbd. (z.sub.1)or a radical of formula z.sub.2 :.dbd.CH-- (z.sub.2)the ring B represents a piperidyl radical, a pyrrolidinyl radical, or a 1,2,3,6-tetrahydropyridyl radical, and R.sub.2 represents: a hydrogen atom, a benzyl radical, or an alkyl radical having 1 to 6 carbon atoms, on condition that in one of these cases R.sub.1 is other than a naphthyl (y.sub.1), dihydronaphthyl (y.sub.2) or tetrahydronaphthyl (y.sub.3) radical and B is other than a piperidinyl radical, or an aminoalkyl radical having 1 to 6 carbon atoms, a cyanoalkyl radical having 1 to 6 carbon atoms,or a radical of formula w.sub.1 : ##STR2## in which n is 1-6 and R.sub.Type: GrantFiled: November 5, 1992Date of Patent: August 31, 1993Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5236919Abstract: The invention concerns a heterocycle of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents orAr is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl;and R.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.Type: GrantFiled: May 11, 1992Date of Patent: August 17, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Philip N. Edwards, Jean-Marc M. M. Girodeau
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Patent number: 5234932Abstract: The present invention relates to hitherto unknown compounds of formula, in which m and n stand for an integer from 0-5, p stands for 0 or 1, and q stands for an integer from 0-4, R.sub.1 and R.sub.2 are the same or different and stand for hydrogen, halogen, nitro, amino, alkyl or alkoxy; R.sub.3 is hydroxy, hydrogen, straight or branched, saturated or unsaturated C.sub.1 -C.sub.6 alkyl; R.sub.5 stands for an acidic group, e.g. carboxy, 1-H tetrazolyl, a sulphonic acid group, a sulfamyl group, a sulphinic acid group, or a hydroxamic acid group; R.sub.4 and R.sub.6 are the same or different and stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.6 alkyl groups or unsubstituted or substituted aralkyl groups. R.sub.7 has the same meaning as R.sub.5 or represents a hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group.Type: GrantFiled: January 29, 1992Date of Patent: August 10, 1993Assignee: Leo Pharmaceutical Products ltd.Inventors: Schneur Rachlin, Erik T. Hansen
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Patent number: 5231103Abstract: The novel quinolin-2-yl-methoxybenzylhydroxyureas can be prepared by reaction of appropriate ketones with hydroxylamine and reduction of the ketoximes and subsequent reaction with isocyanates. The new substances can be employed as active substances in medicaments.Type: GrantFiled: July 21, 1992Date of Patent: July 27, 1993Assignee: Bayer AktiengesellschaftInventors: Michael Matzke, Klaus-Helmut Mohrs, Siegfried Raddatz, Romanis Fruchtmann, Armin Hatzelmann, Christian Kohlsdorfer, Reiner Muller-Peddinghaus, Pia Theisen-Popp
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Patent number: 5229516Abstract: There are disclosed compounds of the formulaA(CH.sub.2).sub.n O-BwhereinA is C.sub.4 -C.sub.8 alkyl, phenoxyethyl, phenoxyphenyl or a group having the formula ##STR1## wherein ##STR2## R.sup.1 is hydrogen, lower alkyl, phenyl or phenyl substituted with trifluoromethyl;R.sup.2 is hydrogen or lower alkyl; orR.sup.1 and R.sup.2 taken together form a benzene ring;R.sup.3 is hydrogen or lower alkyl;n is 1-2;B is ##STR3## wherein ##STR4## m is 0-3; R.sup.5 is ##STR5## or phenyl or phenyl substituted by halo, lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl;R.sup.6 is A(CH.sub.2).sub.n O-- or halo; with the proviso that when R.sup.6 is halo, R.sup.5 is ##STR6## R.sup.7 is lower alkyl; Y is --CH.sub.2 -- or --O--;R.sup.8 is lower alkyl or --(CH.sub.2).sub.m CO.sub.2 R.sup.3 ;R.sup.9 is ##STR7## or --CH.sub.2 R.sup.10 ; R.sup.10 is lower alkyl, phenyl, phenyl substituted with carboxy, halo, loweralkylthio or loweralkylsulfinyl, pyridyl, furanyl or quinolinyl;R.sup.Type: GrantFiled: July 10, 1992Date of Patent: July 20, 1993Assignee: American Home Products CorporationInventors: John H. Musser, Anthony F. Kreft, III, Amedeo A. Failli, Christopher A. Demerson, Uresh S. Shah, James A. Nelson
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Patent number: 5225421Abstract: Compounds having the formula: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti asthmatic, anti allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.Type: GrantFiled: September 16, 1991Date of Patent: July 6, 1993Assignee: Merck Frosst Canada, Inc.Inventors: John W. Gillard, Howard E. Morton, Rejean Fortin, Yvan Guindon
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Patent number: 5221678Abstract: Compounds having the Formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.Type: GrantFiled: July 12, 1991Date of Patent: June 22, 1993Assignee: Merck Frosst Canada, Inc.Inventors: Joseph G. Atkinson, John W. Gillard, Erich L. Grimm
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Patent number: 5215989Abstract: Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members, X and Y are bridging groups, Q is a nitrogen containing heterocycle, R.sup.2 and R.sup.3 are H, substituted or unsubtituted C.sub.1-3 alkyl, C.sub.1-3 alkoxy, N(R).sub.2, halogen, CF.sub.3 or R.sup.5 and R.sup.1 is H or an aryl group.Type: GrantFiled: July 15, 1991Date of Patent: June 1, 1993Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, David A. Claremon, Jason M. Elliott, Gerald S. Ponticello, David C. Remy, Harold G. Selnick
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Patent number: 5212182Abstract: This invention relates to novel quinolinyl- and naphthalenylbenzamides or benylamines and related disclosed compounds of the formula ##STR1## wherein X is nitrogen, NO or CR.sup.1 ; Y is C(R.sup.1)(R.sup.2)O, OC(R.sup.1)(R.sup.2), C(R.sup.1)(R.sup.2)N(R.sup.3), N(R.sup.3)C(R.sup.1)(R.sup.2) or C(R.sup.1).dbd.C(R.sup.2); wherein R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen or lower alkyl containing 1 to 10 carbon atoms; Z is oxygen or (R.sup.1)(R.sup.2); R.sup.4 is R.sup.1, benzyl, benzyl ring substituted with R.sup.5, benzyl alpha monosubstituted with R.sup.1, benzyl ring substituted with R.sup.5 and alpha monosubstituted with R.sup.1, phenyl, phenylalkyl containing 2 to 10 carbon atoms in the alkyl group or phenylalkyl ring substituted with R.sup.5 and containing 2 to 10 carbon atoms in the alkyl group; wherein R.sup.5 is R.sup.1, lower alkoxy containing 1 to 10 carbon atoms, halogen, trihalomethyl, NO.sub.2, N(R.sup.1)(R.sup.2) or C(O)N(R.sup.1)(R.sup.2); R.sup.6 is R.sup.1 or R.sup.6 is C(O)(R.Type: GrantFiled: October 3, 1990Date of Patent: May 18, 1993Assignee: American Home Products CorpoorationInventors: John H. Musser, Albert J. Molinari, Dominick Mobilio
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Patent number: 5212179Abstract: The invention concerns the preparation of compounds of formula ##STR1## and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula ##STR2## in which Q is O, S, --CR.sup.7 .dbd.CR.sup.8 --, --N.dbd.CR.sup.8 -- and --N.dbd.N--; R.sup.4, R.sup.5 and R.sup.6 ; and R.sup.7 and R.sup.8 when present, each represent hydrogen or a substituent selected from lower alkyl, lower alkenyl, lower alkoxy, NO.sub.2, NH.sub.2, haloloweralkyl, hydroxyloweralkyl, aminoloweralkyl, substituted amino, halogen, loweralkoxycarbonyl, cyano, CONH.sub.2 and hydroxy; and additionally either R.sup.4 and R.sup.5 when adjacent or R.sup.6 and R.sup.Type: GrantFiled: October 25, 1990Date of Patent: May 18, 1993Assignee: John Wyeth and Brother LimitedInventors: John L. Archibald, Terence J. Ward
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Patent number: 5204344Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.Type: GrantFiled: February 5, 1991Date of Patent: April 20, 1993Assignee: Merck Frosst Canada, Inc.Inventors: Petpiboon Prasit, Rejean Fortin, John H. Hutchinson, Michel L. Belley, Serge Leger, John Gillard, Richard Frenette
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Patent number: 5204348Abstract: Novel heterocyclic compounds, which are represented by the following general formula, useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.Type: GrantFiled: December 3, 1991Date of Patent: April 20, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Nobuyuki Fukazawa, Makoto Odate, Tsuneji Suzuki, Kengo Otsuka, Takashi Tsuruo, Wakao Sato
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Patent number: 5204358Abstract: Compounds having the formula: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.Type: GrantFiled: January 9, 1992Date of Patent: April 20, 1993Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Robert Zamboni, Jacques-Yves Gauthier, Michel L. Belley
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Patent number: 5202338Abstract: The present invention relates to novel dihydroquinoline derivatives, pharmaceutical compositions and methods of use of dihydroquinoline derivatives as modulators of the arachidonic acid cascade. The novel dihydroquinoline derivatives of this invention are useful for the treatment of diseases, such as asthma, where products of the arachidonic acid cascade contribute to the disease.Type: GrantFiled: October 31, 1990Date of Patent: April 13, 1993Inventors: Vilmos Bar, Zsuzsa Pollak, Istvan Penzes
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Patent number: 5202423Abstract: The invention pertains to terpyridine compounds having structure (I). These compounds form fluorescent lanthanide chelates with the appropriate metal ions. The fluorescent metal chelates are useful as probes in time-resolved fluorescence spectroscopy.Type: GrantFiled: April 19, 1991Date of Patent: April 13, 1993Assignee: Wallac OyInventors: Jouko Kankare, Harri Takalo, Elina Hanninen, Matti Helenius, Veli-Matti Mukkala
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Patent number: 5202326Abstract: The invention concerns a heterocyclic ether of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl or (2-4 C)alkanoyl, or optionally substituted benzoyl;R.sup.2 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl; andR.sup.3 is substituted (1-4C)alkyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: November 25, 1991Date of Patent: April 13, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Jean-Marc M. M. Girodeau
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Patent number: 5196454Abstract: The invention relates to novel 2,5-diaminotetralines of the formula: ##STR1## wherein R1, R2, R3 and R4 are defined herein, processes for preparing them and their use in pharmaceutical compositions. The novel 2,5-diaminotetralines are useful in treating diseases caused by disorders of the dopaminergic systems.Type: GrantFiled: June 15, 1990Date of Patent: March 23, 1993Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Herbert Merz, Joachim Mierau, Gunter Schingnitz, Claus Schneider
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Patent number: 5196419Abstract: The invention concerns a heterocyclic cyclic ether of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the oxygen atom to which A.sup.2 is attached and with the carbon atom to which A.sup.3 is attached, defines a ring having 5 to 7 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino, and which ring may bear one, two or three substituents; andR.sup.Type: GrantFiled: November 4, 1991Date of Patent: March 23, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Annie Hamon
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Patent number: 5189180Abstract: Seco-mevinic acid derivatives are provided which have the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis.New intermediates for preparing the above seco-mevinic acid derivatives are also provided.Type: GrantFiled: May 1, 1991Date of Patent: February 23, 1993Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5187180Abstract: (Quinolin-2-ylmethoxy)Heterotetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes useful in the treatment of asthma and eye inflamation.Type: GrantFiled: July 12, 1991Date of Patent: February 16, 1993Assignee: Merck Frosst Canada, Inc.Inventor: John W. Gillard
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Patent number: 5183827Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O or NR'; where R' is hydrogen or lower alkyl; R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl; R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen, A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; n is 0-5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: July 18, 1991Date of Patent: February 2, 1993Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5175297Abstract: The present invention relates to a process for the preparation of methyl-quinoline derivatives, useful as meflocin intermediates, of the formula (I) ##STR1## or salts thereof, wherein X.sup.1 stands for hydrogen or a non-binding electron pair,R.sup.1 stands for hydrogen or a group of the formula (II) ##STR2## R.sup.2 stands for acyloxy or hydroxyl and the dotted line indicates an optionally aromatic ring.Type: GrantFiled: March 19, 1991Date of Patent: December 29, 1992Assignee: Alkaloida Vegyeszeti GyarInventors: Zoltan Salamon, Jozsef Jeko, Ilona Imre, Magdolna Czeller
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Patent number: 5166347Abstract: Novel carboximidamide derivatives represented by the following formula (A) and acid adduct salts thereof are disclosed: ##STR1## wherein all the substituents have the same meanings as defined above. N-cyano-pyridinecarboximidate compounds represented by the following formula (II) which are the intermediates for preparing of N-cyano-N'-substituted-pyridinecarboximidamide derivatives wherein the substituent B in the above described formula (A) is pyridine is also disclosed: ##STR2## wherein all the substitutents have the same meanings as defined above. The process for preparing the compounds, the pharmaceutical agents comprising the compound having vasodilating effect, and the therapeutic method of dosing the compound on patients for therapy are also disclosed.Type: GrantFiled: December 22, 1989Date of Patent: November 24, 1992Assignee: Kirin Beer Kabushiki KaishaInventors: Toshio Izawa, Tomoko Kashiwabara, Shohachi Nakajima, Nobuyuki Ogawa
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Patent number: 5166359Abstract: An optical recording medium contains novel azulenemethine dyes of the formula ##STR1## where R is unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, X.sup..crclbar. is an anion, A.sup..sym. is heterocyclic radical, of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, Y, Z and W are as defined, with the proviso that, when A.sup..sym. is a radical of the formula II f, II g, II i or II k, m is 2, A is 1, 2 or 3 and M is 1 or 2.Type: GrantFiled: March 28, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Michael Acker, Peter Neumann, Wolfgang Schrott, Matthias Dust
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Patent number: 5166354Abstract: The invention relates to a processes for the preparation of quinoline derivatives of the general formula (I) ##STR1## wherein R.sup.1 stands for hydrogen or a group of the formula (II) ##STR2## which are intermediates for pharmaceutically active compounds.Type: GrantFiled: March 19, 1991Date of Patent: November 24, 1992Assignee: Alkaloida Vegyeszeti GyarInventors: Zoltan Salamon, Jozsef Jeko, Ilona Imre, Magdolna Czeller
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Patent number: 5157122Abstract: An indole having the formula I: ##STR1## is prepared by a Fischer-Indole reaction employing a mixture of phosphorous pentoxide and methane sulfonic acid as an acid catalyst. The reaction, which is optionally run in a co-solvent, provides 3-unsubstituted indoles in high yields with high regioselectivity. The indole thus prepared is an intermediate in the synthesis of leukotriene biosynthesis inhibitors.Type: GrantFiled: January 18, 1991Date of Patent: October 20, 1992Assignee: Merck & Co., Inc.Inventors: David L. Hughes, Dalian Zhao
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Patent number: 5157039Abstract: The present invention relates to compounds of formula ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1- C.sub.8 -alkyl, aryl or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.Type: GrantFiled: December 31, 1990Date of Patent: October 20, 1992Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent T. Nielsen, Ian Ahnfelt-Ronne
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Patent number: 5153358Abstract: A novel process for the preparation of .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids is disclosed. These .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids are useful as intermediates for the preparation of enzyme inhibitors (for example, renin inhibitors) and other peptides or amino acid derivatives or analogs.Type: GrantFiled: January 30, 1991Date of Patent: October 6, 1992Assignee: Abbott LaboratoriesInventor: Thomas M. Zydowsky
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Patent number: 5149703Abstract: Compounds having the formula I: ##STR1## are antagonists of the actions of leukotrienes. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.Type: GrantFiled: September 6, 1991Date of Patent: September 22, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Cheuk K. Lau, Claude Dufresne
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Patent number: 5142052Abstract: Aryl- and heterocyclic-methanamines are prepared by reacting a hydroxy-aryl carbinol or a heterocyclic carbinol with a primary or a secondary amine in the presence of a cationic effect reagent.Type: GrantFiled: October 21, 1988Date of Patent: August 25, 1992Assignee: Laboratoires SyntexInventors: Serge Beranger, Bruno Francois
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Patent number: 5142060Abstract: Herbicidal substituted sulphonylaminotriazolinones of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl,R.sup.2 represents hydrogen or the group --SO.sub.2 --R.sup.1 where R.sup.1 has the abovementioned meaning,R.sup.3 represents hydrogen, halogen, hydroxyl, mercapto, amino or an optionally substituted radical from the group consisting of alkyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenylthio, alkinylthio, aralkoxy, aralkylthio, alkylamino and dialkylamino,R.sup.4 represents hydrogen, halogen, hydroxyl, amino or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino,X represents nitrogen or a CH group,Y represents nitrogen or a CR.sup.5 group whereR.sup.Type: GrantFiled: October 17, 1991Date of Patent: August 25, 1992Assignee: Bayer AktiengesellschaftInventors: Klaus-Helmut Muller, Rolf Kirsten, Joachim Kluth, Klaus Konig, Hans-Jochem Riebel, Peter Babczinski, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5140047Abstract: Tricyclic hydroxyurea and hydroxamate compounds, pharmaceutical compositions, and their use as as inhibitors of the oxidation of polyunsaturated fatty acids, such as by inhibition on the 5-lipoxygenase enzyme, and treatment of diseases therein.Type: GrantFiled: May 3, 1991Date of Patent: August 18, 1992Assignee: SmithKline Beecham CorporationInventors: Jerry L. Adams, Ravi S. Garigipati
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Patent number: 5136038Abstract: A dihydropyridine.revreaction. pyridinium salt type of redox, or chemical, delivery system for the site-specific and/or site-enhanced delivery of a radionuclide to the brain is provided. A chelating agent capable of chelating with a radionuclide and having a primary, secondary or tertiary amino function can be converted to the corresponding analogue in which said function is replaced with a dihydropyridine.revreaction. pyridinium salt redox system and then complexed with a radionuclide to provide a new radiopharmaceutical that, in its lipoidal dihydropyridine form, penetrates the blood-brain barrier ("BBB") and allows increased levels of radionuclide concentration in the brain, particularly since oxidation of the dihydropyridine moiety in vivo to the ionic pyridinium salt retards elimination from the brain while elimination from the general circulation is accelerated. This radionuclide delivery system is well suited for use in scintigraphy and similar radiographic techniques.Type: GrantFiled: August 2, 1990Date of Patent: August 4, 1992Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 5134148Abstract: The invention concerns a heterocycle of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl;and R.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.Type: GrantFiled: September 5, 1991Date of Patent: July 28, 1992Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Philip N. Edwards, Jean-Marc M. M. Girodeau
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Patent number: 5122608Abstract: There is provided a process for the preparation of a substituted or unsubstituted 2,3-pyridine or quinolinedicarboxylic acid by hydrolysis of a substituted or unsubstituted 2,3-pyridine or quinolinedicarboxylic acid diester with an acid having an ionization constant pK.sub.a of less than 3.0 followed by isolation of the product as the free acid or an acid salt.Type: GrantFiled: December 19, 1990Date of Patent: June 16, 1992Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5120744Abstract: Substituted (quinolin-2-ylmethoxy)phenyl-thio-ureas of the formula ##STR1## in which A, B, D, E, G, K and Mrepresent hydrogen, hydroxyl, halogen, carboxyl, nitro, trifluoromethyl or trifluoromethoxy, orrepresent alkyl, alkoxy or alkoxycarbonyl, orrepresent aryl, which is optionally substituted by halogen, hydroxyl, nitro or cyano,R.sup.1represents hydrogen or alkyl, which is optionally substituted by aryl or cycloalkyl, orrepresents cycloalkyl,R.sup.2represents alkyl, which is optionally substituted by halogen or hydroxy, orrepresents cycloalkyl, which is optionally substituted by halogen or cyano, orrepresents aryl which is optionally substituted by halogen, nitro, cyano, alkyl, or by --SO.sub.2 --R.sup.3, in whichR.sup.3 denotes alkyl or --NR.sup.4 R.sup.5, in whichR.sup.4 and R.sup.5 denote hydrogen, alkyl or phenyl,orR.sup.2 represents --CO--R.sup.6, in whichR.sup.Type: GrantFiled: October 5, 1990Date of Patent: June 9, 1992Assignee: Bayer AktiengesellschaftInventors: Siegfried Raddatz, Klaus Mohrs, Burkhard Fugmann, Romanis Fruchtmann, Christian Kohlsdorfer, Reiner Muller-Peddinghaus, Pia Theisen-Popp
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Patent number: 5118691Abstract: Substituted tetrahydropyridines and derivatives thereof are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as dopaminergic, antipsychotic, and antihypertensive agents as well as for treating hyperprolactinaemia-related conditions and central nervous system disorders.Type: GrantFiled: June 17, 1991Date of Patent: June 2, 1992Assignee: Warner-Lambert Co.Inventors: Juan C. Jaen, David G. Nickell, Donna M. Reynolds, Sarah J. Smith, Lawrence D. Wise, David J. Wustrow