Quinolines Which Are Unsubstituted Or Which Are Alkyl Or Alkenyl Substituted Only, Or Salt Thereof Patents (Class 546/181)
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Patent number: 5753676Abstract: This invention concerns a compound of generic formula: ##STR1## or a pharmaceutically acceptable salt thereof, where the dotted lines represent optional bonds,R.sup.3 is an optionally substituted C.sub.6 -C.sub.10 aryl or heteroaryl group; optionally substituted by one or more substituents the same or different,R' represents one or more optional substituents the same or different, selected from the following: halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.7 alkoxycarbonyl, C.sub.1 -C.sub.6 hydroxyalkyl, CN, aminocarbonyl, C.sub.2 -C.sub.7 alkanoyloxy(C.sub.1 -C.sub.6 )alkyl, carboxy, C.sub.2 -C.sub.7 alkanoxylamino, optionally substituted C.sub.6 -C.sub.10 or heteroaryl or an optionally substituted (C.sub.6 -C.sub.10 aryl)alkyl or a heteroaryl alkyl radical; andR" represents one or more optional mono- or di- valent substituents in the 5, 7 or 8 positions the same or different: monovalent substituents being selected from the following: C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.7 alkanoyloxy, hydroxy, amino, C.Type: GrantFiled: September 29, 1995Date of Patent: May 19, 1998Inventors: Roger Crossley, Albert Opalko, Peter Jonathan Meade, Anderson Decourtney Ifill, Brian John Bushell
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Patent number: 5714488Abstract: Compounds having the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein W is selected from the group consisting of optionally substituted quinolyl, optionally substituted benzothiazolyl, optionally substituted benzoxazolyl, optionally substituted benzimidazolyl, optionally substituted quinoxalyl, optionally substituted pyridyl, optionally substituted pyrimidyl, and optionally substituted thiazolyl; R.sup.1 and R.sup.2 are one or more groups independently selected from hydrogen, alkyl, halolalkyl, alkoxy, and halogen; Z is selected from the group consisting of N--OH, N--O--A--COM, CH--COM, and CH--CH.dbd.N--0--A--COM wherein A is selected from the group consisting of alkylene, alkenylene, cycloalkylene, and optionally substituted alkylphenyl wherein the alkyl portion is of one to six carbon atoms, and M is selected from the group consisting of a pharmaceutically acceptable, metabolically clearable group, --OR.sup.3, and --NR.sup.4 R.sup.Type: GrantFiled: September 17, 1996Date of Patent: February 3, 1998Assignee: Abbott LaboratoriesInventors: Clint D. W. Brooks, Pramila Bhatia, Teodozyj Kolasa
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Patent number: 5700942Abstract: There are provided processes for preparing quinolines by vapor phase reaction of a substituted or unsubstituted aniline base, formaldehyde and a C.sub.2 -C.sub.4 aldehyde wherein the aldehydes:aniline base molar ratio is at least 2:1. More preferred processes of the invention achieve high selectivities and yields of 8-methylquinoline, and high conversions of the aniline base.Type: GrantFiled: July 11, 1996Date of Patent: December 23, 1997Assignee: Reilly Industries, Inc.Inventors: Colin H. McAteer, Robert D. Davis, Sr., Joel R. Calvin
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Patent number: 5695684Abstract: A mesomorphic compound represented by a formula (I) containing a quinoline-2,6-diyl skeleton is suitable as a component for a liquid crystal composition providing improved response characteristics and a high contrast. A liquid crystal device is constituted by disposing the liquid crystal composition between a pair of electrode plates. The liquid crystal device may preferably be used as a display panel constituting a liquid crystal apparatus providing good display characteristics.Type: GrantFiled: March 27, 1995Date of Patent: December 9, 1997Assignee: Canon Kabushiki KaishaInventors: Yoko Kosaka, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Shinichi Nakamura
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Patent number: 5691363Abstract: Compounds having the formula ##STR1## wherein Q is ##STR2## R.sup.1 is C.sub.1 -C.sub.8 alkyl; R.sup.2 is C.sub.4 -C.sub.17 heterocyclic aryl, unsubstituted or substituted with one or more C.sub.1 -C.sub.6 alkyl, halo or nitro, containing a sulfur atom, a nitrogen atom, or one or two oxygen atoms;X is nitrogen; andn is 2, 3 or 4,or a stereoisomer thereof. These compounds are useful as fungicides.Type: GrantFiled: August 14, 1996Date of Patent: November 25, 1997Assignee: Uniroyal Chemical Company, Inc.Inventors: Shih-Yu Ma, Robert Allan Davis
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Patent number: 5677458Abstract: Compounds of the formula ##STR1## which are intermediates in the preparation of hydantoin aldose reductase inhibitors and methods of preparing these intermediates.Type: GrantFiled: October 3, 1996Date of Patent: October 14, 1997Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5552549Abstract: Chlorinated aromatic compounds are dechlorinated in a simple and inexpensive manner by heating them to 300.degree. to 450.degree. C. in a salt melt in the presence of water and/or water vapor and carbon.Type: GrantFiled: September 29, 1994Date of Patent: September 3, 1996Assignee: Bayer AktiengesellschaftInventors: Christian Rasp, Helmut Waldmann, Hans-Joachim Traenckner
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Patent number: 5541196Abstract: Substituted quinolines having formula (1), wherein R.sub.1, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 each independently represent a hydrogen atom, a linear or branched C.sub.1-7 alkyl, alkenyl, epoxy-alkyl or mono/polyalcohol group; an amine group or an amide group, an OR group in which R is hydrogen or a C.sub.1-7 alkyl or alkenyl group or a phenyl group; and R.sub.2 is an OR group in which R is as defined above, or a C.sub.1-7 alkyl alkenyl or epoxyalkyl group, a phenyl, phenol, methylenedioxyphenyl, or dimethoxyphenyl group, or a C.sub.1-7 alkyl, alkenyl or epoxyalkyl group, a phenyl, phenol, methylenedioxyphenyl, or dimethoxphenyl group or a C.sub.1-7 alkyl, alkenyl or epoxy-alklyl group comprising at least one of the following substituents: a C.sub.1-4 alkyl or alkenyl group; a phenyl, phenol, dimethylphenyl, dimethoxyphenyl or methylenedioxphenyl group; or an OR group in which R is hydrogen or a C.sub.1-4 alkyl or alkenyl group; or an NHR group in which R is hydrogen or a C.sub.Type: GrantFiled: June 9, 1994Date of Patent: July 30, 1996Assignee: Institut Francais de Recherche Scientifique Pour le Developpment en Cooperation (ORSTOM)Inventors: Alain Fournet, Alcira Angelo Barrios, Victoria Munoz, Reynald Hocquemiller, Fran.cedilla.ois Roblot, Jean Bruneton, Pascal Richomme, Jean Charles Gantier
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Patent number: 5491164Abstract: The present invention comprises dipeptide analogs that inhibit the farnesylation of Ras. These farnesyl-protein transferase inhibitors are characterized by the inclusion of a cyclic amine in the backbone of the dipeptide. Further contained in this invention are chemotherapeutic compositions containing these farnesyl transferase inhibitors and methods for their production.Type: GrantFiled: September 29, 1994Date of Patent: February 13, 1996Assignee: Merck & Co., Inc.Inventors: S. Jane deSolms, Samuel J. Graham
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Patent number: 5486613Abstract: The present invention relates to vulcanization accelerators constituted by compounds, derived from secondary amines, belonging to the class of enamines and to a process for their preparation.Type: GrantFiled: July 11, 1994Date of Patent: January 23, 1996Assignee: Great Lakes Chemical Italia S.r.l.Inventors: Fabio Broussard, Mauro Adovasio, Corrado Callierotti, Gianbattista Taroni, Jose Roncalli
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Patent number: 5478832Abstract: A quinoline compound represented by the formula (1) or a salt thereof: ##STR1## wherein the definition of each substituents are described in the specification, which have angiotensin II antagonism and hypotensive action and are useful as an agent for the prevention and treatment of cardiovascular system diseases such as hypertension, heart failure and the like.Type: GrantFiled: May 4, 1993Date of Patent: December 26, 1995Assignees: The Green Cross Corporation, Asahi Glass Co., Ltd.Inventors: Yoshihisa Inoue, Hajime Ebisu, Naomichi Ishida, Norifumi Nakamura, Jun Sasaki, Takashi Okazoe, Yoshitomi Morizawa, Arata Yasuda
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Patent number: 5474994Abstract: This invention provides bicyclic heterocyclic derivatives and their pharmaceutically acceptable salts useful for the treatment of hypertension, urethral and lower urinary tract contractions, and other disorders. The compounds are also useful for binding .alpha..sub.1 -adrenergic and 5HT.sub.1A serotonergic receptors, in vitro or in vivo.Type: GrantFiled: May 26, 1993Date of Patent: December 12, 1995Assignee: Recordati S.A., Chemical and Pharmaceutical CompanyInventors: Amedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
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Patent number: 5457103Abstract: Compounds of the general formula (I): ##STR1## in which R represents: a hydrogen atom, ora radical --OR'in which R' is as defined in the description.Type: GrantFiled: August 18, 1993Date of Patent: October 10, 1995Assignee: Adir et CompagnieInventors: Yves Rolland, Guy Lewin, Jean-Paul Vilaine, Albert Lenaers, Catherine Thollon
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Patent number: 5438140Abstract: Nickelized shaped articles are produced by electrodeposition of nickel from aqueous acidic baths containing as essential constituents one or more nickel salts, one or more inorganic acids and one or more brighteners, the brighteners used being cyclic ammonium compounds I ##STR1## where the nitrogen atom is part of a pyridine, quinoline or isoquinoline ring system which can additionally carry one or two C.sub.1 -C.sub.4 -alkyl substituents,R.sup.1 and R.sup.2 are each hydrogen or C.sub.1 -C.sub.4 alkyl,A is a group of the formula --CO--O--R.sup.3, --CO--CH.sub.2 --CO--O--R.sup.3, --O--CO--R.sup.3 or --O--R.sup.3,whereR.sup.3 is C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, C.sub.7 -C.sub.12 -phenylalkyl or phenyl which can be substituted by one or two C.sub.1 -C.sub.4 -alkyl radicals, C.sub.1 -C.sub.4 -alkoxy radicals, halogen atoms, hydroxyl groups, phenyl radicals or C.sub.1 -C.sub.4 alkoxycarbonyl groups, m is from 0 to 10, n is from 1 to 4, p is 0 or 1, and X.sup..crclbar.Type: GrantFiled: April 28, 1994Date of Patent: August 1, 1995Assignee: BASF AktiengesellschaftInventors: Alfred Oftring, Bernd Burkhart, Volker Schwendemann, Klaus Glaser
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Patent number: 5411969Abstract: The present invention relates to novel dihydroquinolines which are useful for cholesterol lowering and as antioxidant agents. Also provided is a process for preparing the dihydroquinolines of the present invention, pharmaceutical compositions, and a method of treating or inhibiting hypercholesterolemia, hyperlipidemia, atherosclerosis, and LDL oxidation which comprises administering to birds and mammals in need of such treatment an effective amount of a compound of the present invention.Type: GrantFiled: April 16, 1993Date of Patent: May 2, 1995Assignee: Bristol-Myers Squibb CompanyInventors: Bradley C. Pearce, John J. Wright
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Patent number: 5409929Abstract: There are provided novel nitrogen-containing bicyclic 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 17, 1993Date of Patent: April 25, 1995Assignee: The DuPont Merck Pharmaceutical CompanyInventor: Engelbert Ciganek
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Patent number: 5410052Abstract: Mthods and apparatus for the extraction of a ligand such as molecular oxygen from a first fluid environment and for release of a ligand such as molecular oxygen, as well as ligand carrier compounds therefore comprising linear, pentadentate polyalkylamines and transition metal ions. The carrier compounds have the general formula: ##STR1## where, each of R.sub.1 and R.sub.2 is independently an organic group including a sulfur, an oxygen or a nitrogen coordinated to M;each of m, n. o, and p is 1, 2 3, or 4;X is selected from the group consisting of 2,6-pyridyl, 2,6-piperidyl, 2,5pyrrolyl, 2,4-imidazolyl, substituted heterocyclic amines, --O--, --S-- >P--R.sub.3, and >N--R.sub.3 where R.sub.3 is hydrogen, lower alkyl, or aralkyl; andM is a transition metal ion.Type: GrantFiled: September 25, 1990Date of Patent: April 25, 1995Assignee: The Regents of the University of CaliforniaInventors: Kevin M. Smith, Joseph P. Ciccone, N. Venkata Ramana
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Patent number: 5296484Abstract: The compounds of the formula: ##STR1## wherein the substituents are herein below defined; are plant fungicides, insecticides, and miticides.Type: GrantFiled: March 20, 1989Date of Patent: March 22, 1994Assignee: DowElancoInventors: Michael J. Coghlan, Barry A. Dreikorn, Glen P. Jourdan, Robert G. Suhr
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Patent number: 5294622Abstract: The compounds of the formula: ##STR1## where the substituents are herein below defined, are fungicides, insecticides, and miticides.Type: GrantFiled: March 24, 1992Date of Patent: March 15, 1994Assignee: DowElancoInventors: Barry A. Dreikorn, Glen P. Jourdan, Robert G. Suhr
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Patent number: 5260442Abstract: The invention concerns quinolinium salt intermediates of the formula I ##STR1## and processes for their manufacture; and their use in the manufacture of aryloxymethyl-substituted 1-alkyl-2-quinolone derivatives which are 5-lipoxygenase inhibitors.Type: GrantFiled: December 5, 1991Date of Patent: November 9, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Jonathan Hutton, David Waterson
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Patent number: 5221677Abstract: The invention concerns a heterocyclic derivative 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;X.sup.1 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 or (3-6C)alkynyl; andR.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.2 is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: September 21, 1990Date of Patent: June 22, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Philip N. Edwards
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Patent number: 5212313Abstract: Compounds of the Formula VII: ##STR1## Wherein: X.sup.1 and X.sup.2 are each independently selected from --H, cyano, alkyl, alkoxy, aryl, carbamoyl, sulphamoyl, COOH and carboxylic acid ester;Z.sup.2 and Z.sup.2 are both --O--;R.sup.1 and R.sup.2 are each independently selected from H, or an optionally substituted alkyl, alkenyl, cycloalkyl, aryl and aralkyl group;R.sup.4, R.sup.5, R.sup.7 and R.sup.8 are each independently --H, halogen or an optionally substituted alkyl, alkenyl or alkoxy group; orR.sup.1 and R.sup.4 or R.sup.2 and R.sup.5 together with N atom and Ring B from a tetrahydroquinolinyl group; and R.sup.6 is selected from H, halogen or an optionally substituted alkyl or alkoxy group and a group NR.sup.1 R.sup.2 in which each of R.sup.1 and R.sup.2 are independently as hereinbefore described and where R.sup.6 is NR.sup.1 R.sup.2, R.sup.6 is the same or different form the NR.sup.1 R.sup.2 group present in Ring B.Type: GrantFiled: October 23, 1991Date of Patent: May 18, 1993Assignee: Imperial Chemical Industries PlcInventors: Ronald W. Kenyon, David F. Newton, Derek Thorp
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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: 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: 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: 5157182Abstract: A dehydrocyclization process is described for producing polynuclear organic compounds by contacting a starting organic material having at least one ring moiety comprising at least two adjacent ring carbon atoms each bonded to an independently selected monovalent radical comprising at most about eight carbon atoms provided at least one of the monovalent hydrocarbon radicals comprises more than one carbon atom with a crystalline copper aluminum borate catalyst. The preferred catalyst comprises at least one member selected from the group consisting of (a) crystalline copper aluminum borate and (b) zero valent copper on a support comprising at least one member selected from the group consisting of Al.sub.4 B.sub.2 O.sub.9 and the crystalline copper aluminum borate, the zero valent copper on the support being formed by the reduction of the crystalline copper aluminum borate.Type: GrantFiled: June 19, 1991Date of Patent: October 20, 1992Assignee: Amoco CorporationInventors: Patrick E. McMahon, Larry C. Satek
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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: 5124455Abstract: There are disclosed compounds of the formula ##STR1## wherein R is ##STR2## R.sup.1 is hydrogen, lower alkyl or ##STR3## a is 1-3; b is 1-3;c is 0-2;X, Y and Z are each, independently, a bond, O, S. or NH, with the proviso that if one of X or Y is O, S or NH, the other must be a bond;R.sup.2 is amino, loweralkylamino, arylamino, loweralkoxy or aryloxy;R.sup.3 is hydrogen, halo, hydroxy, lower alkoxy, aryloxy, loweralkanoyloxy, amino, lower alkylamino, arylamino or loweralkanoylamino;R.sup.4 and R.sup.5 are each, independently hydrogen or lower alkyl;m is 0-4;n is 1-4; ando is 1-4;and, which by virtue of their ability to selectively inhibit an isoenzyme of 3':5'-cyclic AMP phosphodiesterase located in pulmonary smooth muscle tissue and inflammatory cells, are bronchodilatory and antinflammatory and so are useful in the treatment of acute and chronic bronchial asthma and associated pathologies.Type: GrantFiled: August 8, 1990Date of Patent: June 23, 1992Assignee: American Home Products CorporationInventor: Louis J. Lombardo
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Patent number: 5061718Abstract: The invention relates to an anti-inflammatory or antiallergic composition containing a compound of the formula ##STR1## wherein A is ##STR2## R.sup.1 is aryl which may have cyano or carbamoyl, or heterocyclic group which may have lower alkyl,R.sup.2 is hydrogen or lower alkyl,R.sup.3 is lower alkyl,X is hydrogen, halogen, hydroxy or lower alkyl,m is an integer 1 or 2, andn is an integer 1 to 4, or pharmaceutically acceptable salts thereof.Type: GrantFiled: January 30, 1990Date of Patent: October 29, 1991Assignee: Fujisawa Pharmaceutical Company, Ltd.Inventors: Teruo Oku, Yoshio Kawai, Hiroshi Kayakiri, Kazuyoshi Kuratani, Masashi Hashimoto
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Patent number: 5001294Abstract: Aromatic alkenes, especially diarylbutadienes are produced in a simple economic process by reaction of an anil with an organic compound having a non-aromatic unsaturated system conjugated with an aromatic system, and a terminal methyl group pendent from the non-aromatic unsaturated system; in particular the organic compound is a propenyl-substituted aromatic compound.Type: GrantFiled: October 31, 1988Date of Patent: March 19, 1991Inventor: Allan S. Hay
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Patent number: 4962203Abstract: Compounds having the formula: ##STR1## are selective antagonists of leukotrienes of D.sub.4. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.Type: GrantFiled: August 14, 1989Date of Patent: October 9, 1990Assignee: Merck Frost Canada, Inc.Inventors: Robert N. Young, Haydn W. R. Williams, Serge Leger, Richard Frenette, Robert Zamboni
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Patent number: 4927936Abstract: The invention concerns a compound formula II ##STR1## or an acid addition salt thereof, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are the same or different and represent hydrogen, or loweralkyl, cycloalkyl or lower aralkyl, any of which radicals may be substituted by lower alkyl, lower alkoxy or CF.sub.3 or phenyl radicals which may be substituted by lower alkyl or CF.sub.3 or R.sup.2 and R.sup.3 taken together, form a 5, 6 or 7 membered saturated ring R.sup.4 and R.sup.5 may also represent lower alkoxy, or cycloalkoxy, n is 1, 2, or 3 and, if more than one R.sup.4 radical is present the R.sup.4 radicals may be the same or different with the provisos that (1) when R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are all hydrogen, R.sup.6 R.sup.7 are not both hydrogen, (2) when R.sup.1 and R.sup.3 are both phenyl and when R.sup.1 is methyl and R.sup.4 is methyl then R.sup.6 and R.sup.7 are not both methyl, and (3) when R.sup.1 is hydrogen or methyl, R.sup.Type: GrantFiled: December 16, 1988Date of Patent: May 22, 1990Assignee: John Wyeth and Brother Ltd.Inventors: Roger Crossley, Kenneth Heatherington
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Patent number: 4923991Abstract: The invention provides a compound of formula III ##STR1## or an acid addition salt thereof, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are the same or different and represent hydrogen or lower alkyl, cycloalkyl, lower aralkyl or phenyl radicals any of which radicals may be substituted by lower alkyl, lower alkoxy or trifluoromethyl or R.sup.2 and R.sup.3 taken together, form a 5, 6 or 7 membered saturated ring, R.sup.4 and R.sup.5 may also represent lower alkoxy or cycloalkoxy, n is 1, 2 or 3 and, if more than one R.sup.4 radical is present the R.sup.4 radicals may be the same or different and esters of carboxylic acids with the hydroxy group shown, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n are as defined above, with the provisos that (1) R.sup.6 and R.sup.7 are other than hydrogen when R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are all hydrogen and (2) R.sup.6 and R.sup.7 are not both methyl when R.sup.4 is methyl.Type: GrantFiled: December 16, 1988Date of Patent: May 8, 1990Assignee: John Weyth & Brother LimitedInventors: Roger Crossley, Kenneth Heatherington
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Patent number: 4923881Abstract: The invention relates to an anti-inflammatory or antiallergic composition containing a compound of the formula ##STR1## wherein A is ##STR2## R.sup.1 is aryl which may have cyano or carbamoyl, or heterocyclic group which may have lower alkyl,R.sup.2 is hydrogen or lower alkyl,R.sup.3 is lower alkyl,X is hydrogen, halogen, hydroxy or lower alkyl,m is an integer 1 or 2, andn is an integer 1 to 4, or pharmaceutically acceptable salts thereof.Type: GrantFiled: April 13, 1988Date of Patent: May 8, 1990Assignee: Fujisawa Phatmaceutical Co., Ltd.Inventors: Teruo Oku, Yoshio Kawai, Hiroshi Kayakiri, Kazuyoshi Kuratani, Masashi Hashimoto
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Patent number: 4897482Abstract: Oligomeric 2,2,4-trimethyl-1,2-dihydroquinoline (TMQ) is prepared from monomeric TMQ by heating the latter in the presence of a polybasic aliphatic carboxylic acid and in the presence of small amounts of water.Type: GrantFiled: May 31, 1989Date of Patent: January 30, 1990Assignee: Bayer AktiengesellschaftInventors: Manfred Blazejak, Karl J. Wemmje, Heinz Hammer
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Patent number: 4889934Abstract: Novel organic mixed complexes are provided which have the general formulaD.sup.+.[A.TCNQ]wherein D.sup.+ is an N-alkylonium cation derived from a nitrogen-containing hetercyclic compound (D) selected from the group consisting of pyridines, guinolines, isoquinolines and imidazoles and [A.TCNQ] is an anion radical derived from a 2,5-bis[(alkoxycarbonyl)-ethyl]-7,7,8,8-tetracyanoquinodimethane (A) of the formula ##STR1## in which R is an alkyl group containing 1-10 carbon atoms, and 7,7,8,8-tetracyanoquinodimethane (TCNQ).Type: GrantFiled: January 26, 1988Date of Patent: December 26, 1989Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Takeo Kawabata, Masahiko Miyashita, Akira Taisha
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Patent number: 4885368Abstract: Novel radical ion salts of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each hydrogen, methyl, ethyl, phenyl, methoxy, ethoxy, fluorine, chlorine or bromine, or R.sup.1 or R.sup.1 and R.sup.3 may furthermore be tert-butyl and/or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4 together may in each case form a radical of the formula ##STR2## where z is 0, 1, 2 or 3, and the fused aromatic rings are unsubstituted or monosubstituted or disubstituted by chlorine, bromine, methyl and/or methoxy, M.sup.m.sym. is an m-valent alkali metal, alkaline earth metal, transition metal, tin, lead, thallium, ammonium, phosphonium, arsonium or stibonium ion, k is from 1 to 5, l is from 0.1 to 4, m is from 1 to 3, n is from 0.1 to 4, x is from 0 to 2 and y is from 0 to 6, and k, l, n, x and y may furthermore be non-integral numbers and (l+x)=n.m, are electrically conductive in the crystalline state. A number of the salts are stable at 300.degree. C. and above.Type: GrantFiled: November 23, 1987Date of Patent: December 5, 1989Assignee: BASF AktiengesellschaftInventors: Siegfried Huenig, Alexander Aumueller, Peter Erk
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Patent number: 4868304Abstract: A method of synthesizing nitrogen heterocycles such as indoles, indolines, oxindoles, quinolines, isoquinolines, and isoquinolones, all of which are pharmacologically active. The method involves cyclizing a haloaryl alkene in the presence of a catalytically effective amount of a palladium(II) ion source and in the presence of a cyclizing promoting base such as an alkali metal salt.Type: GrantFiled: May 27, 1988Date of Patent: September 19, 1989Assignee: Iowa State University Research Foundation, Inc.Inventors: Richard C. Larok, Srinivasan Babu
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Patent number: 4847364Abstract: Methine-azo compounds of the formula ##STR1## in which A is the complement to a heterocyclic 5- or 6-membered ring which has a quaternized N atom as a ring member, which can contain further hetero atoms and which can be substituted or/and be fused with carbocyclic or heterocyclic rings,R is hydrogen, cyano or C.sub.2 --C.sub.3 -alkylene which is bonded to an N atom of ring A to form a 5- or 6-membered ring,B is substituted or unsubstituted phenylene or naphthylene,X.sup..crclbar. is an anion andKK is the radical of an open-chain coupling component which contains active methylene groups, except that, if A is the complement to a pyridinium ring, KK cannot be the radical of acetoacetanilide which is unsubstituted or alkyl-substituted in the aniline ring.They are suitable for use as dyes for dyeing and printing cationically dyeable substrates, in particular paper.Type: GrantFiled: June 16, 1987Date of Patent: July 11, 1989Inventor: Peter Mockli
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Patent number: 4837329Abstract: A process for preparing dihydro compounds of formula I, by rearranging compounds of formula II, e.g. in the presence of acids or noble metal catalysts, is described. The compounds II may be prepared from intermediates of formula III. ##STR1## In these formulae R.sup.1,R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are the same or different and represent hydrogen, or alkyl, cycloalkyl, aralkyl, or aryl radicals any of which radicals may be substituted, or R.sup.1 and R.sup.2 taken together or R.sup.2 and R.sup.3 taken together, form a 5, 6 or 7 membered ring which may be saturated or unsaturated and substituted or unsubstituted, R.sup.4 and R.sup.5 may also represent alkoxy, or cycloalkoxy, n is 1, 2 or 3 and, if more than one R.sup.4 radical is present the R.sup.4 radicals may be the same or different and R.sup.6 and R.sup.7 represent hydrogen, alkyl, cycloalkyl, or aralkyl radicals.Most of the compounds I, II and III are novel and are claimed. They are intermediates for anti-ulcer agents.Type: GrantFiled: January 18, 1984Date of Patent: June 6, 1989Assignee: American Home Products CorporationInventors: Roger Crossley, Kenneth Heatherington
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Patent number: 4835272Abstract: A process for formation of a base, which comprises reacting an acetylide compound with a salt. The acetylide compound has the following formula:(R--C.tbd.C--).sub.n Mwherein R is a monovalent group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heterocyclic group, each of which may have one or more substituent groups; M is an n-valent transition metal atom; and n is 1, 2 or 3. The salt is composed of an anion having an affinity for the transition metal (M) (the affinity of the anion for the transition metal is more than that of the acetylide anion (R--C.tbd.C.crclbar.)), and a cation derived from one selected from the group consisting of an alkali metal, an alkaline earth metal, ammonia and an organic base. A light-sensitive material containing the acetylide compound and the salt is also disclosed.Type: GrantFiled: July 16, 1987Date of Patent: May 30, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Shunichi Ishikawa, Ken Kawata
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Patent number: 4801713Abstract: Novel, highly electroconductive organic complexes are disclosed which have the general formulaD.sup.+.A.sup.-wherein the constituent D.sup.+ is an N-alkyl-onium cation (D.sup.+) derived from a nitrogen-containing heterocyclic compound (D) selected from the group consisting of pyridines, quinolines, isoquinolines and imidazoles and the constituent A.sup.- is the anion radical corresponding to a 2,5-disubstituted-7,7,8,8-tetracyanoquinodimethane (A) of the general formula ##STR1## wherein X is --COOR (R being an alkyl group containing 1-10 carbon atoms) or --CN.Type: GrantFiled: January 26, 1988Date of Patent: January 31, 1989Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Takeo Kawabata, Akira Taisha
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Patent number: 4755600Abstract: Thermosettable prepolymers or resins are prepared by reacting (1) a pyrazine compound containing at least two substituent groups which have a hydrogen atom attached to a carbon atom which is attached to the ring such as tetramethylpyrazine, (2) a material containing at least two aromatic aldehyde groups, and (3) at least one of (a) a nitrogen containing aromatic heterocyclic compound containing at least one hydrogen atom attached to a carbon atom attached to the ring and a polymerizable unsaturated group such as 2-methyl-5-vinylpyridine or (b) an aldehyde containing at least one polymerizable unsaturated group such as 4-isopropenyl-1-cyclohexene-1-carboxaldehyde. These prepolymers or resins are curable to thermoset products having good mechanical and thermal properties by heat and pressure or by homopolymerization or copolymerization with N,N'-bis-imides such as 1,1'-(methylenedi-4,1-phenylene)bismaleimide. The prepolymers are suitable for preparing composites.Type: GrantFiled: March 17, 1986Date of Patent: July 5, 1988Assignee: The Dow Chemical CompanyInventor: Duane S. Treybig
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Patent number: 4746743Abstract: Process for producing 2,2,4-trimethyl-1,2-dihydroquinoline by reacting aniline with an acetone compound at 80.degree.-150.degree. C. in the presence of, as catalyst, both hydrogen fluoride and boron trifluoride.Type: GrantFiled: June 21, 1985Date of Patent: May 24, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Masakatsu Yoshimura, Takeo Fujii, Kikumitsu Inoue, Masahito Umehara, Hideo Nagasaki
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Patent number: 4642347Abstract: There are disclosed compounds of the formula ##STR1## wherein Z is CR or N, when n=1; or Z is O, S, or NR, when n=0; n is 0 or 1; p is 1-10; R.sup.1 is hydrogen, loweralkyl, loweralkoxy or halo; R.sup.2 is hydrogen, loweralkyl, loweralkoxy or halo; or R.sup.1 and R.sup.2 taken together form a benzene ring; and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like.Type: GrantFiled: May 21, 1985Date of Patent: February 10, 1987Assignee: American Home Products CorporationInventors: Anthony F. Kreft, III, Thomas W. Pattison, John H. Musser
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Patent number: 4622400Abstract: Methods are provided for making certain m-aminophenols using a sulfonation/alkali fusion procedure. The aminophenols are key intermediates in the synthesis of dyes, particularly efficient, stable dyes for laser application. Preparations of some rhodamine and phenoxazone dyes from the m-aminophenols are described.Type: GrantFiled: December 29, 1983Date of Patent: November 11, 1986Assignee: The United States of America as represented by the United States Department of EnergyInventor: Peter R. Hammond
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Patent number: 4617395Abstract: Quinoline and substituted quinolines are prepared by reacting aniline or a substituted aniline with an .alpha., .beta.-monounsaturated aldehyde in a high-boiling mineral oil by a method in which the high-boiling mineral oil is replaced when it becomes enriched with by-products, and the said mineral oil enriched with by-products is removed.Type: GrantFiled: October 15, 1984Date of Patent: October 14, 1986Assignee: BASF AktiengesellschaftInventors: Toni Dockner, Helmut Hagen, Herbert Krug
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Patent number: 4537713Abstract: The invention concerns a process for the reduction of groups containing unsaturated C,C--, C,N--,N,N--,N,O-- bonds, especially of NO.sub.2 --,NO--,NOH--,NR--,CN--,N.sub.3 --,N.sub.2 -groups or C.dbd.C or C-halogen- or acyl groups with hydrogen on MPc or with a suitable reduction agent on [MPc].sup..crclbar., whereby a platinum metal-phthalocyanine is used as the catalyst. It is possible that by the reversible change (control) of the oxidation phase z of the platinum metal from z.gtoreq.2 to z.ltoreq.1 using the same MPc complex, basically different reductions can be selectively catalysed.Thus the invention concerns a process for selective reduction using platinum metal-phthalocyanine catalysts with reaction specificity in three different reaction patterns.The inventive process is suitable, especially for the synthesis of .alpha.-phenylalkylamines, benzylalkylamines, N-alkyl-amino carboxylic acids, .alpha.Type: GrantFiled: May 19, 1982Date of Patent: August 27, 1985Inventor: Heiner Eckert
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Patent number: 4514570Abstract: Disclosed is a process for preparing 2,2,4-trimethyl-1,2-dihydroquinoline compounds by reacting acetone with an aniline compound in the presence of a strongly acidic sulfonic acid-type macroreticular cation exchange resin catalyst. 2,2,4-Trimethyl-1,2-dihydroquinoline compounds are obtained in good yield and containing substantially no catalyst residue contaminant.Type: GrantFiled: March 2, 1984Date of Patent: April 30, 1985Assignee: Eastman Kodak CompanyInventor: Joseph S. Bowers, Jr.
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Patent number: 4400318Abstract: Disclosed are azo compounds having the formula ##STR1## in which R.sup.4 is straight or branched lower alkylene, Z is 1-3 groups selected from such heteroatom groups as --OH, lower alkanoyloxy, lower alkoxy, lower alkoxycarbonyl, lower alkoxyalkoxy, mono- or dialkylamino, --CN, carbamoyl, formamide, lower alkyl substituted carbamoyl, lower alkoxycarbonylamino, lower alkanoylamino, hydroxy substituted lower alkoxy, halogen, lower alkylthio, lower alkylsulfonyl, and various heterocyclic groups such as furyl and pyrrolidono, R is selected from straight or branched lower alkyl, phenyl and phenyl substituted with straight or branched lower alkyl, halogen, or straight or branched lower alkoxy, R.sup.2 is hydrogen or lower alkyl, and A is an aniline, tetrahydroquinoline, or benzomorpholine coupler component which may be substituted with a wide variety of groups.Type: GrantFiled: November 4, 1981Date of Patent: August 23, 1983Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, Clarence A. Coates, Jr.