Acyclic Sulfur Bonded Directly To Oxygen And Directly Or Indirectly To The Quinoline Ring System By Nonionic Bonding Patents (Class 546/172)
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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: 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: 5138067Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sub.1 is alkyl or alkylcarbamoyl; R.sub.2 is lower alkyloxy, lower alkylcarbamoyloxy, lower alkylcarbonylamino, lower alkyloxycarbonylamino, lower alkylureido, lower alkyloxymethyl, lower alkylcarbonylmethyl, cyanomethyl, heterocyclic group, or heterocyclyloxy; R.sub.2 ' is hydrogen or R.sub.2 and R.sub.2 ' taken together with R.sub.2 form --O(CH.sub.2).sub.m -- wherein m is an integer of 1 to 5; R.sub.3, R.sub.4, and R.sub.5 each is hydrogen or lower alkyl or two or three of R.sub.3, R.sub.4, and R.sub.5 taken together with the adjacent nitrogen atom form cyclic ammonio; R.sub.6 is hydrogen or lower alkylcarbonyl; X.sup.- is a counter anion; Y is oxygen or sulfur; and n is an integer of 1 to 10, being useful as PAF antagonists, e.g., as antithrombotic, antivasoconstricting, antibronchoconstricting agent or antitumor agent.Type: GrantFiled: May 29, 1991Date of Patent: August 11, 1992Assignee: Shionogi & Co. Ltd.Inventors: Susumu Kamata, Tatsuo Tsuri, Nobuhiro Haga, Takeaki Matsui, Morio Kishi, Kimio Takahashi, Sanji Hagishita, Kaoru Seno
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Patent number: 5136034Abstract: Thioacids, thiols, an acid, and an aldehyde are used to produce chiral thioacetals of the general formula. ##STR1## The compounds are leukotriene antagonists.Type: GrantFiled: October 5, 1990Date of Patent: August 4, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Michel Therien, Jacques-Yves Gauthier, Robert Zamboni, Michel L. Belley
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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: 5134147Abstract: Compounds of formula I ##STR1## in which m represents an integer from 0 to 5, n represents an integer from 1 to 2, p is equal to 0, 1 or 2,X, Y and Z, which may be identical or different, each represent a hydrogen atom, a halogen atom, a linear or branched alkyl radical, a trifluoromethyl radical, an alkoxy radical, an alkylthio radical or a hydroxyl radical, andR represents a 2-benzofuranyl or 2,3-dihydro-2-benzofuranyl radical (it being possible for each to be substituted on the benzene ring), a 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-2-yl radical, a 4-oxo-4H-chromen-2-yl radical (optionally substituted on the benzene ring), a benzocyclobutenyl radical of formula A or an indanyl radical of formula B: ##STR2## (in which: R.sub.1 and R.sub.Type: GrantFiled: October 21, 1991Date of Patent: July 28, 1992Assignee: Adir et CompagnieInventors: Jean L. Peglion, Francis Colpaert
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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: 5128366Abstract: The compounds of the present invention inhibit HMG-CoA reductase, and subsequently suppress the synthesis of cholesterol. And they are useful in the treatment of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis. The compounds have the formula ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 each is independently hydrogen, optionally substituted lower alkyl, or optionally substituted aryl; R.sup.4 is lower alkyl, aralkyl, aryl, or heteroaryl, each of which is optionally substituted; X is vinylene or ethylene; Y is ##STR2## where R.sup.5 is hydrogen, lower alkyl, aryl, aralkyl, or a cation capable of forming a non-toxic pharmaceutically acceptable salt.Type: GrantFiled: May 30, 1991Date of Patent: July 7, 1992Assignee: Shinogi & Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Haruo Koike, Masamichi Watanabe
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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: 5118689Abstract: A new piperidine compound is pharmacologically effective for treatment of arrythmia and has the formula: ##STR1## in which R.sup.1 is lower alkyl or tolyl; R.sup.2 is hydrogen, lower alkyl, lower alkenyl, cycloalkyl or cycloalkylalkyl; X is --CO--, --CH.sub.2 -- or --CHOH--; the sum of g plus h equals the integer 3 or 4 with g and h being 1, 2 or 3; A is substituted or unsubstituted alkylene, alkenylene, --(CH.sub.2).sub.k --S--, wherein k is an integer of 2 to 5, or --(CH.sub.2).sub.p CO--, wherein p is an integer of 1 to 4; and B is a compound having at least one heterocyclic ring containing a nitrogen atom.Type: GrantFiled: October 9, 1990Date of Patent: June 2, 1992Assignee: Eisai Co., Ltd.Inventors: Hitoshi Oinuma, Motosuke Yamanaka, Kazutoshi Miyake, Tomonori Hoshiko, Norio Minami, Tadao Shoji, Yoshiharu Daiku, Kohei Sawada, Kenichi Nomoto
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Patent number: 5114952Abstract: A series of novel alkanesulphonamidophenyl-N-alkyl-N-(heterocyclic-alkyl)alkylamine derivatives have been prepared, including their pharmaceutically acceptable salts. These compounds are useful in therapy as anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. Said sulfonamide compounds are of the formula: ##STR1## wherein R and R.sup.1 are each C.sub.1 -C.sub.4 alkyl; X is --CH.sub.2 --, --CO-- or --CH(OH)--; n is two, three or four; and "Het" is a nitrogen-containing heterocyclic group wherein said heterocyclic group is preferably 2H-3,4-dihydroisoquinol-1-on-2-yl or 2H-isoquinol-1-on-2-yl, each optionally substituted with halogen or C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: November 21, 1990Date of Patent: May 19, 1992Assignee: Pfizer Inc.Inventors: John E. Arrowsmith, Peter E. Cross, Geoffrey N. Thomas
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Patent number: 5109009Abstract: 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: September 10, 1990Date of Patent: April 28, 1992Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent T. Nielsen, Ian Ahnfelt-Ronne
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Patent number: 5104882Abstract: 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: May 22, 1990Date of Patent: April 14, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Robert Zamboni, Jacques-Yves Gauthier, Michel L. Belley
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Patent number: 5102881Abstract: 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: December 20, 1989Date of Patent: April 7, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Robert Zamboni, Petpiboon Prasit, Robert N. Young
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Patent number: 5094683Abstract: Herbicidal sulphonylaminocarbonyltriazolinones of the formula ##STR1## in which R.sup.1 represents hydrogen, hydroxyl or amino, or represents an optionally substituted radical from the series comprising alkyl, alkenyl, akinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino and dialkylamino,R.sup.2 represents hydrogen hydroxyl, mercapto or amino, or represents an optionally substituted radical from the series comprising alkyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkylamino and dialkylamino, andR.sup.3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, and salts thereof. Intermediates of the formula ##STR2## in which A.sup.1 represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, alkoxy or dialkylamino andA.sup.2 represents hydrogen, or represents in each case optionally substituted alkyl, cycloalkyl, aralkyl, aryl or alkoxy,provided that both A.sup.1 and A.sup.Type: GrantFiled: April 29, 1991Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Werner Daum, Klaus-Helmut Muller, Michael Schwamborn, Peter Babczinski, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5091392Abstract: A quinolin-2-yl-methoxy)phenylacyl-sulphonamide or -cyanamide of the formula ##STR1## in which A, B, D, E, F and G are identical or different andrepresent hydrogen, hydroxyl, halogen, carboxyl, nitro, trifluoromethyl, trifluoromethoxy or a group of the formula --NH.sup.3 R.sup.4, in whichR.sup.3 and R.sup.4 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 8 carbon atoms or aryl having 6 to 10 carbon atoms,represent straight-chain or branched alkyl, alkoxy or alkoxycarbonyl in each case having up to 12 carbon atoms,represent aryl having 6 to 10 carbon atoms,R.sup.1 represents cycloalkyl having 3 to 8 carbon atoms,R.sup.2 represents hydrogen orstraight-chain or branched alkyl having up to 10 carbon atoms,represents an alkali metal,represents cycloalkyl having 3 to 8 carbon atoms,X represents a group of the formula --SO.sub.2 --R.sup.5, in whichR.sup.Type: GrantFiled: May 1, 1990Date of Patent: February 25, 1992Assignee: Bayer AktiengesellschaftInventors: Siegfried Raddatz, Klaus-Helmut Mohrs, Romanis Fruchtmann, Christian Kohlsdorfer, Pia Theisen-Popp, Reiner Muller-Peddinghaus
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Patent number: 5086180Abstract: Sulphamoylathiophenes of the formula ##STR1## in which Y denotes O or S,A denotes a single bond or a straight-chain or branched alkylene group having 1-5 carbon atoms,R.sub.1 denotes methyl or trifluoromethyl andR.sub.2 denotes hydrogen or a group COOH or COOR.sub.3, in whichR.sub.3 represents (C.sub.1 -C.sub.4)-alkyl,and, in the case in which R.sub.2 denotes a group COOH, their pharmaceutically tolerable salts, a process for their preparation, pharmaceutical preparations which contain these compounds and their use in medicaments as leukotriene antagonists for the treatment of asthma and allergies.Type: GrantFiled: June 15, 1990Date of Patent: February 4, 1992Assignee: Chemisch Pharmazeutische Forschungsgesellschaft m.b.H.Inventors: Dieter Binder, Franz Rovenszky, Norman Brunner, Hubert P. Ferber
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Quinoline substituted naphthalenepropionic acid derivatives as anti-inflammatory/antiallergic agents
Patent number: 5084575Abstract: There are disclosed compounds of the formula ##STR1## wherein a is alkyl 3-19 carbon atoms, diloweralkyl allyl, diahaloallyl, diphenylallyl, lower alkynyl, ##STR2## W is --CR.sub.2 O--, --CH.dbd.CH-- or --CH.dbd.CHCH.sub.2 O-- X is N or CR;Z is ##STR3## R is hydrogen or lower alkyl; Y is ##STR4## R.sup.1 is hydrogen, lower alkyl or phenyl; R.sup.2 is hydrogen or lower alkyl; orR.sup.1 and R.sup.2 taken together form a benzene ring, optionally substituted by halo;R.sup.3 is --OR, ##STR5## -- NHSO.sub.2 R.sup.4 ; R.sup.4 is phenyl or loweralkyl substituted phenyl;R.sup.5 is halo;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as alelrgic rhinitis, allergic bronchial asthma and the like, in psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other immediate hypersensitivity reactions.Type: GrantFiled: September 6, 1990Date of Patent: January 28, 1992Assignee: American Home Products CorporationInventors: Anthony F. Kreft, III., John H. Musser, James J. Bicksler, John W. Giberson, Dennis M. Kubrak, Annette L. Banker -
Patent number: 5084463Abstract: This invention relates to N-heteroalkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing anti-arrhythmic activity, to pharmaceutical compositions and to methods for production thereof.Type: GrantFiled: December 27, 1990Date of Patent: January 28, 1992Assignee: American Home Products CorporationInventors: John A. Butera, Jehan F. Bagli
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Patent number: 5082943Abstract: Disclosed are novel imidazole derivatives having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are H, alkyl, cycloalkyl, aryl, aralkyl or halogen-substituted alkyl, or R.sup.1 and R.sup.2 are combined to form a heterocyclic ring; R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are H, halogen, alkoxy, aralkyloxy, alkyl, alkoxycarbonyl, nitro, amino, acyl, fluorine substituted-alkyl, or fluorine substituted-alkoxy, or R.sup.3 is combined with R.sup.2 to form a heterocyclic ring; R.sup.8 and R.sup.9 are H, halogen, alkoxy, alkyl, alkoxycarbonyl, nitro, amino, acyl, fluorine substituted-alkyl, fluorine substituted-alkoxy, or aryl group which may have a substituent, or R.sup.8 and R.sup.9 are combined to form an alicyclic ring; R.sup.7 is, where R.sup.8 and R.sup.9 are not combined, H, and, where R.sup.8 and R.sup.9 are combined, H, alkyl which may have a substituent, aryl which may have a substituent, arylcarbonyl which may have a substituent, or a sulfur-containing heterocyclic group; and n is 0 or 1.Type: GrantFiled: February 20, 1991Date of Patent: January 21, 1992Assignee: Nippon Chemiphar Co., Ltd.Inventors: Susumu Okabe, Mitsuo Masaki, Tomio Yamakawa, Hitoshi Matsukura, Yutaka Nomura
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Patent number: 5082849Abstract: This invention relates to certain quinolinyl-benzopyran compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists and/or mediator release inhibitors possessing anti-inflammatory and anti-allergic properties.Type: GrantFiled: March 8, 1991Date of Patent: January 21, 1992Inventors: Fu-Chich Huang, Henry F. Campbell, Keith S. Learn
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Patent number: 5071988Abstract: There are disclosed compounds of the formulaA(CH.sub.2).sub.n O--BwhereinA is ##STR1## n is 1-2; B is ##STR2## wherein R.sup.4 and R.sup.5 are each, independently, hydrogen or lower alkyl;R.sup.6 is hydrogen, halo or nitro; ##STR3## R.sup.8 is lower alkyl; m is 0-3;and the pharmacologically acceptable salts thereof, and their use in the treatment of inflammatory conditions, such as rheumatoid arthritis, ulcerative colitis, psoriasis and other immediate hypersensitivity reactions; in the treatment of leukotriene-mediated nasobronchial obstructive air-passageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like; and as gastric cytoprotective agents.Type: GrantFiled: February 27, 1991Date of Patent: December 10, 1991Assignee: American Home Products CorporationInventors: Amedeo A. Failli, Anthony F. Kreft, III, John H. Musser, Annette L. Banker, James A. Nelson, Uresh S. Shah
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Patent number: 5062879Abstract: 8-Azolylmethylquinolines I ##STR1## (R=H, halogen, CN, C.sub.1 -C.sub.4 -alkyl; X=halogen; A=the 1-yl radical of a 5-membered, aromatic heterocycle with 2 or 3 nitrogen atoms in the ring, which may also bear further substituents; B=Cl, Br, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, an amine radical which may be mono- or disubstituted, a radical ZR.sup.4 where R.sup.4 =phenyl which may bear further substituents, and Z=oxygen, sulfur or an amine radical which may be alkylated) and the acid addition salts and metal complexes of I.The compounds I and the salts and metal complexes thereof are suitable as herbicides.Type: GrantFiled: May 9, 1990Date of Patent: November 5, 1991Assignee: BASF AktiengesellschaftInventors: Rainer Seele, Gunter Brill, Reiner Kober, Thomas Saupe, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5055473Abstract: A series of novel N-alkyl-N-(alkanesulphonamidoheterocyclicmethyl) -4-alkanesulphonamidophenethylamines have been prepared, including their pharmaceutically acceptable salts and various key novel intermediates therefor. The heterocyclic moiety present in these compounds is a benzo-fused heterocyclic group derived from either benzofuran, benzothiophene, benzoxazole or quinoline, and it is attached to the adjacent methyl group of the molecule by means of the available ring carbon atom which is situated alpha to the hetero atom. These particular compounds are useful in therapy as highly effective anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. Preferred member compounds include N-methyl-N-(5-methanesulphonamidobenzofur-2-ylmethyl)-4 -methanesulphonamidophenethylamine and N-methyl-N-(6- methanesulphonamidoquinol-2-ylmethyl)-4-methane-sulphonamidophenethylamine . Methods for preparing all these compounds from known starting materials are provided.Type: GrantFiled: May 29, 1990Date of Patent: October 8, 1991Assignee: Pfizer Inc.Inventors: John E. Arrowsmith, Peter E. Cross, Geoffrey N. Thomas
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Patent number: 5047540Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sub.1 is alkyl or alkylcarbamoyl; R.sub.2 is lower alkyloxy, lower alkylcarbamoyloxy, lower alkylcarbonylamino, lower alkyloxycarbonylamino, lower alkylureido, lower alkyloxymethyl, lower alkylcarbonylmethyl, cyanomethyl, heterocyclic group, or he0 terocyclyloxy; R.sub.2 ' is hydrogen or R.sub.2 and R.sub.2 ' taken together form --O(CH.sub.2).sub.m -- wherein m is an integer of 1 to 5; R.sub.3, R.sub.4, and R.sub.5 each is hydrogen or lower alkyl or two or three of R.sub.3, R.sub.4, and R.sub.5 taken together with the adjacent nitrogen atom form cyclic ammonio; R.sub.6 is hydrogen or lower alkylcarbonyl; X.sup.- is a counter anion; Y is oxygen or sulfur; and n is an integer of 1 to 10, being useful as PAF antagonists, e.g., as antithrombotic, antivasoconstricting, antibronchoconstricting agent or antitumor agent.Type: GrantFiled: November 29, 1988Date of Patent: September 10, 1991Assignee: Shionogi & Co., Ltd.Inventors: Susumu Kamata, Tatsuo Tsuri, Nobuhiro Haga, Takeaki Matsui, Morio Kishi, Kimio Takahashi, Sanji Hagashita, Kaoru Seno
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Patent number: 5047412Abstract: The invention describes novel (2-styryl-, 2-naphthyl- and 2-phenethyl-4-o-hydroxyphenyl-1,3-dioxan-5-yl)alkenoic acids and related tetrazoles and sulphonamides, of the formula I wherein Q completes a benzene or pyridine ring, Y is vinylene, Z is carboxy, 1(H)-tetrazol-5-yl or a group of the formula --CO.NHSO.sub.2 R.sup.6, and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, A.sup.1, A.sup.2, n and m have the meanings defined in the specification, and pharmaceutically acceptable salts thereof, for use in conjunction with their pharmaceutical compositions in treating certain pulmonary and/or vascular disorders. The invention also describes various processes and intermediates for the manufacture of the novel compounds.Type: GrantFiled: February 1, 1989Date of Patent: September 10, 1991Assignee: Imperial Chemical Industries PLCInventors: George R. Brown, Michael J. Smithers
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Leukotriene-inhibiting substituted (quinolin-2-yl-methoxy)phenyl-N,N'-sulphonylureas and use thereas
Patent number: 5045547Abstract: Lipoxygenase-inhibiting and leukotriene-inhibiting substituted (quinolin-2-yl-methoxy)phenyl-N,N'-sulphonylureas of the formula ##STR1## and physiologically acceptable salts thereof.Type: GrantFiled: February 23, 1990Date of Patent: September 3, 1991Assignee: Bayer AktiengesellschaftInventors: Siegfried Raddatz, Klaus Mohrs, Romanis Fruchtmann, Christian Kohlsdorfer, Reiner Muller-Peddinghaus, Pia Theisen-Popp -
Patent number: 5041453Abstract: This invention relates to certain quinolinyl-benzoheterobicyclic compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists and/or as mediator release inhibitors useful as anti-inflammatory and anti-allergic agents.Type: GrantFiled: May 30, 1990Date of Patent: August 20, 1991Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Fu-Chih Huang, Keith S. Learn, Ashvin V. Gavai
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Patent number: 5032592Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.Type: GrantFiled: May 30, 1989Date of Patent: July 16, 1991Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, John Oldfield, Howard Tucker
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Patent number: 5032590Abstract: Substituted hydroxylamines of the formula ##STR1## in which R.sup.1 stands for an aromatic or heterocyclic radical,are especially useful in the treatment of hyperlipoproteinaemia, lipoproteinaemia and atherosclerosis.Type: GrantFiled: March 8, 1990Date of Patent: July 16, 1991Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
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Patent number: 5030654Abstract: A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: May 19, 1989Date of Patent: July 9, 1991Assignee: Pfizer Inc.Inventors: Ian T. Barnish, John C. Danilewicz, Keith James, Gillian M. R. Samuels, Nicholas K. Terrett, Michael T. Williams, Martin J. Wythes
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Patent number: 5028709Abstract: The invention relates to vat dyes of the formula ##STR1## wherein [A] and [A'] and X are as defined in claim 1. The vat dyes of formula I are suitable for dyeing or printing a wide range of materials. Dyeings with good fastness properties are obtained in particular on cellulose material.Type: GrantFiled: January 21, 1987Date of Patent: July 2, 1991Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
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Patent number: 5017583Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: February 23, 1988Date of Patent: May 21, 1991Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
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Patent number: 5013826Abstract: The azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.2 is a group of the formula, --CN, --CON(R.sub.8)R.sub.9, --COR.sub.10, --COOR.sub.11, --SO.sub.2 R.sub.12 or --CONHNHR.sub.13, R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.10 alkoxy or phenoxy, R.sub.4 is substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, R.sub.5 is C.sub.1 -C.sub.4 alkyl, R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.8, R.sub.9 and R.sub.13, independently of one another, are hydrogen or substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, R.sub.10, R.sub.11 and R.sub.12 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl, X is an oxygen atom or a group of the formula --CH(R.sub.14)-- in which R.sub.14 is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: February 21, 1989Date of Patent: May 7, 1991Assignee: Ciba-Giegy CorporationInventor: Harald Walter
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Patent number: 5006534Abstract: Substituted benzyl ethers, benzyl thioethers, and benzylamines of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and represent hydrogen, alkyl, alkenyl, cycloalkyl, alkoxy, alkylthio, halogenoalkyl, sulphonylalkyl, halogenoalkoxy, halogenoalkylthio, aralkoxy, aralkylthio, halogen, nitro, cyano or hydroxyl, or represent a group of the formula ##STR2## wherein R.sup.4 and R.sup.5 are identical or different and represent hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl or acyl,R.sup.3 represents a group of the formula ##STR3## in which R.sup.6 represents hydrogen, alkyl or acyl,R.sup.7 represents hydrogen or alkyl andn represents a number from 3 to 10,B represents --CH.sub.2 --X-- or --X--CH.sub.2 --,wherein X represents O, S or NR.sup.7,and wherein R.sup.7 has the abovementioned meaning and the group ##STR4## represents a benzo-fused heterocyclic system, A in the heterocyclic radical being 3-, 4- or 5-membered and containing nitrogen, oxygen and/or sulphur as hetero-atoms.Type: GrantFiled: January 30, 1989Date of Patent: April 9, 1991Assignee: Bayer AktiengesellschaftInventors: Klaus-Helmut Mohrs, Romanis Fruchtmann, Christian Kohlsdorfer
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Patent number: 5003077Abstract: Methine dye which contains a cycloheptimidazole nucleus having a substituent at its 1-position thereof and in which the 7-membered ring moiety is substituted by a methine bond having an auxochrome, at the terminal thereof, for forming a conjugated resonance chromophoric group with the 10 .pi. electron series of the nucleus, showing a long absorption with one or a few methine bonds and have high light-stability and solution-stability.Type: GrantFiled: August 7, 1989Date of Patent: March 26, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Takanori Hioki, Kazuhiko Matsumoto
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Patent number: 4996214Abstract: This invention covers quinolinyl substituted phenyl/thioalkanoic acid substituted propionic acids leukotriene inhibitors having the following general formula ##STR1## where the substituents are defined herein.Type: GrantFiled: June 28, 1990Date of Patent: February 26, 1991Assignee: SmithKline Beecham CorporationInventors: Russell D. Cousins, James S. Frazee, John G. Gleason, Ralph F. Hall
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Patent number: 4994469Abstract: There are provided new compounds of the Formula I ##STR1## obtained by the condensation of 2,2,2-trimethyl-1,2-dihydroquinoline or salts thereof with an oxo derivative of the Formula R.sub.1 R.sub.2 CO--whereinR.sub.1 stands for optionally substituted C.sub.1-4 alkyl andR.sub.2 stands for optionally substituted C.sub.1-2 alkyl,X stands for hydrogen or SO.sub.3 M--wherein M stands for hydrogen, alkali or alkaline earth metal ion,Y stands for hydrogen or acyl. The new compounds can be used as antioxidants, and particularly for increasing coccidiostatic effect.Type: GrantFiled: December 16, 1988Date of Patent: February 19, 1991Assignee: Material Vegyipari KisszovetkezetInventors: Janos Szvoboda, Tamas Rozsnyai, Jozsef Szente, Laszlo Melovits, Imre tvos, Ilona Legradi, Laszlo Prohaszka, Jeno Fekete
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Patent number: 4992456Abstract: Fungicidal 2,5-disubstituted 1,3,4-thiadiazoles of the formula ##STR1## in which R.sup.1 represents alkyl or unsubstituted or substituted aralkyl andR.sup.2 represents in each case unsubstituted or substituted aryl or aralkyl, or represents an unsubstituted or substituted and optionally benzo-fused heterocyclic radical,excluding the compound 2,5-bis[(phenylmethyl)-sulphonyl]-1,3,4-thiadiazole.Type: GrantFiled: November 1, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Diehr, Albrecht Marhold, Wilhelm Brandes, Gerd Hanssler
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Patent number: 4977162Abstract: This invention relates to certain quinolinyl-chromone compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties.Type: GrantFiled: July 13, 1989Date of Patent: December 11, 1990Assignee: Rorer Pharmaceutical CorporationInventors: Fu-Chih Huang, Henry F. Campbell, Keith S. Learn, Robert A. Galemmo, Jr.
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Patent number: 4968681Abstract: Substituted hydroxylamines of the formula ##STR1## in which R.sup.1 stands for an aromatic or heterocyclic radical, are especially useful in the treatment of hyperlipoproteinaemia, lipoproteinaemia and atherosclerosis.Type: GrantFiled: November 15, 1988Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
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1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, process for producing them and use thereof
Patent number: 4968680Abstract: The present invention relates to novel 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime-O-sulfonic acid compound, processes for producing said compounds, intermediate compounds to produce said compounds and compositions containing said compounds with potent diuretic activity that can be used for treating and/or preventing hypertension, oedema and/or for removing ascites.The present invention is based on the selection of 1-acyl-7-halo-2,3-dihydro-4(1H)-quinolinone-4-oxime-O-sulfonic acid compounds, namely heterocyclic-or fused heterocyclic- carbonyl derivatives at 1 position.The compounds of the present invention containing these substituents have potent hypotensive, antioedematous and diuretic effect as well as an activity to remove ascites and are extremely useful for the treatment of diseases and disorders mentioned above.Type: GrantFiled: October 28, 1988Date of Patent: November 6, 1990Assignees: Mochida Pharmaceutical Co., Ltd., Hodogaya Chemical Co., Ltd.Inventors: Ei Mochida, Akio Uemura, Kazuo Kato, Hiroki Tokunaga, Akinori Haga -
Patent number: 4966855Abstract: The invention provides new redox indicators and uses for these redox compounds (I): ##STR1## Wherein X is oxygen or sulphur, R.sub.1 is julolidine or tetrahydroquinoline, which can carry an alkyl radical on the nitrogen atom which, in turn, can be substituted by a sulphuric, phosphonic or carboxylic acid residues, or is (II); wherein R.sub.4 is hydroxyl or a mono- or dialkylated amino group, R.sub.5 and R.sub.6, which can be the same or different, are hydrogen, alkyl or alkoxy, R.sub.2 is hydrogen or alkyl, julolidine or tetrahydroquinoline, which can carry an alkyl on the nitrogen atom which alkyl can be substituted by sulphuric, phosphonic or carboxylic acids, or is III; wherein R.sub.5 and R.sub.6 are the same as in R.sub.1 and R'.sub.4 is hydroxyl, an amino or a mono-or dialkylated amino group, whereby the alkyl radicals can be substituted one or more times by hydroxyl, alkoxy, halogen, morpholine or a sulphuric, carboxylic or phosphonic acid residue, which acids can also be esterified, and R.sub.Type: GrantFiled: July 2, 1985Date of Patent: October 30, 1990Assignee: Boehringer Mannheim GmbHInventors: Ulfert Deneke, Werner Guthlein, Wolfgang Weckerle, Hans Wielinger
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Patent number: 4963566Abstract: A hydroquinoline compound of the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, A, l, m and n are as defined or its pharmaceutically acceptable salt, composition containing the compound and processes for preparing same are disclosed. The compound is useful as an antiulcer agent.Type: GrantFiled: March 27, 1987Date of Patent: October 16, 1990Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Minoru Uchida, Seiji Morita, Masatoshi Chihiro
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Patent number: 4937255Abstract: For inhibiting 3-hydroxy-3-methylglutaryl coenzyme A and cholesterol biosynthesis, the novel disubstituted pyrroles of the formula ##STR1## in which R.sup.1 is aryl or heteroaryl,R.sup.2 is cycloalkyl or optionally substituted alkyl,R.sup.3 is hydrogen or cycloalkyl, or optionally substituted alkyl, aryl or heteroaryl,X is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,A is ##STR2## R.sup.6 is hydrogen or alkyl, and R.sup.7 is hydrogen, a cation or alkyl, aryl or aralkyl.Type: GrantFiled: March 16, 1989Date of Patent: June 26, 1990Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gunter Thomas
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Patent number: 4927935Abstract: A compound of the formula I ##STR1## where A is nitro, amino, halocarbonyl or halosulfonyl, R is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkanoylamino, hydroxyl, C.sub.1 -C.sub.4 -alkoxy phenoxy which is unsubstituted by methyl or chloro, mercapto, C.sub.1 -C.sub.4 -alkylthio, phenylthio which is unsubstituted or substituted by ethyl, fluoro, or methoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenoxycarbonyl which is unsubstituted or substituted by isopropyl, bromo, or methoxy, carbamoyl, hydroxysulfonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl which is unsubstituted or substituted by ethyl, chloro, or isopropoxy, sulfamoyl or trifluoromethyl or is C.sub.1 -C.sub.4 -alkyl which may be substituted by hydroxyl, C.sub.1 -C.sub.4 -alkoxy or halogen, and X and Y are each, independently of one another, halogen, hydroxysulfonyl, C.sub.1 -C.sub.Type: GrantFiled: November 7, 1988Date of Patent: May 22, 1990Assignee: BASF AktiengesellschaftInventors: Alfred Hackenberger, Manfred Patsch
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Patent number: 4920132Abstract: This invention relates to certain quinoline-diaryl compounds and their use as leukotriene D.sub.4 antagonists for the treatment of hypersensitive disorders.Type: GrantFiled: November 3, 1987Date of Patent: April 24, 1990Assignee: Rorer Pharmaceutical Corp.Inventors: Fu-chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
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Patent number: 4920131Abstract: This invention relates to quinolinyl compounds of the general formula: ##STR1## and the use of these compounds as pharmacological agents which are lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties and their pharmaceutical compositions and processes for this preparation.Type: GrantFiled: June 21, 1988Date of Patent: April 24, 1990Assignee: Rorer Pharmaceutical Corp.Inventors: Fu-Chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
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Patent number: 4920130Abstract: This invention relates to certain quinoline-diaryl compounds and their use as leukotriene D.sub.4 antagonists for the treatment of hypersensitive disorders.Type: GrantFiled: November 3, 1987Date of Patent: April 24, 1990Assignee: Rorer Pharamceutical Corp.Inventors: Fu-chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
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Patent number: 4920133Abstract: This invention relates to certain quinoline-diaryl compounds and their use as leukotriene D.sub.4 antagonists for the treatment of hypersensitive disorders.Type: GrantFiled: November 3, 1987Date of Patent: April 24, 1990Assignee: Rorer Pharmaceutical Corp.Inventors: Fu-chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell