Chalcogen Attached Directly To The Carbocyclic Ring Of The Quinoline Ring System By Nonionic Bonding Patents (Class 546/177)
  • Patent number: 5109009
    Abstract: 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: Grant
    Filed: September 10, 1990
    Date of Patent: April 28, 1992
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventors: Ole Bent T. Nielsen, Ian Ahnfelt-Ronne
  • Patent number: 5093340
    Abstract: New phenylsulphonamides of the formula in which ##STR1## R.sup.1 represents a pyridyl, quinolyl or isoquinolyl radical which is unsubstituted or substituted by halogen, alkyl, cycloalkyl, alkoxy, cyano, nitro, halogenoalkyl, halogenoalkoxy, alkoxycarbonyl or alkylsulphonyl,R.sup.2 represents hydrogen, cyano, nitro, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or alkoxycarbonyl,R.sup.3 represents an aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, halogenoalkyl, halogenoalkoxy, alkyl, alkoxy, alkylthio, alkylsulphonyl, cyano, nitro or alkoxycarbonyl, the substitutents being identical or different, or represents pentafluorophenyl or represents a straight-chain, branched or cyclic alkyl which is unsubstituted or substituted by halogen, aryl, aryloxy, cyano, alkoxycarbonyl, alkoxy, alkylthio or trifluoromethyl, andX represents an --O--, --A--B-- or --B--A-- group, whereA denotes --O--, ##STR2## B denotes --O--; ##STR3## where R.sup.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: March 3, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Mohrs, Elisabeth Perzborn, Friedel Seuter, Romanis Fruchtmann, Christian Kohlsdorfer
  • Patent number: 5082943
    Abstract: 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: Grant
    Filed: February 20, 1991
    Date of Patent: January 21, 1992
    Assignee: Nippon Chemiphar Co., Ltd.
    Inventors: Susumu Okabe, Mitsuo Masaki, Tomio Yamakawa, Hitoshi Matsukura, Yutaka Nomura
  • Patent number: 5075303
    Abstract: Pyridine derivatives of formula ##STR1## their heteroaromatic N-oxides and their pharmaceutically acceptable acid addition salts are disclosed. In the formula z is 0, 1 and 2 and R, R.sup.1, R.sup.2 and R.sup.2 have specified meanings. The compounds exhibit activity as 5-HT.sub.1A agonists, antagonists or partial agonists and are useful for the treatment of CNS disorders e.g. anxiety, as antihypertensives and in treating anorexia.
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: December 24, 1991
    Assignee: John Wyeth & Brother Limited
    Inventors: Ian A. Cliffe, Howard L. Mansell, Richard S. Todd, Alan C. White
  • Patent number: 5070096
    Abstract: New phenylsulphonamide of the formula in which ##STR1## R.sup.1 represents a pyridyl, quinolyl or isoquinolyl radical which is unsubstituted or substituted by halogen, alkyl, cycloalkyl, alkoxy, cyano, nitro, halogenoalkyl, halogenoalkoxy, alkoxycarbonyl or alkylsulphonyl,R.sup.2 represents hydrogen, cyano, nitro, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or alkoxycarbonyl,R.sup.3 represents an aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, halogenoalkyl, halogenoalkoxy, alkyl, alkoxy, alkylthio, alkylsulphonyl, cyano, nitro or alkoxycarbonyl, the substituents being identical or different, or represents pentafluorophenyl or represents a straight-chain, branched or cyclic alkyl which is unsubstituted or substituted by halogen, aryl, aryloxy, cyano, alkoxycarbonyl, alkoxy, alkylthio or trifluoromethyl, andX represents an --O--, --A--B-- or --B--A-- groupwhereA denotes --O--, ##STR2## and B denotes --CH.sub.2 -- or ##STR3## where R.sup.
    Type: Grant
    Filed: November 15, 1990
    Date of Patent: December 3, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Mohrs, Elisabeth Perzborn, Friedel Seuter, Romanis Fruchtmann, Christian Kohlsdorfer
  • Patent number: 5032590
    Abstract: 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: Grant
    Filed: March 8, 1990
    Date of Patent: July 16, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
  • Patent number: 5021438
    Abstract: Novel compounds having an affinity for 5-hydroxytryptamine receptors of the formula ##STR1## in which R.sup.1 stands for H, alkyl, aralkyl or heteroarylalkyl,X stands for H, OCH.sub.3, OH, SCH.sub.3, halogen, CN or CONH.sub.2,Y stands for a straight-chain or branched, saturated or unsaturated alkylene chain having up to 6 carbon atomsandZ stands for a group of the formula ##STR2## --OR.sup.4, --SO.sub.m R.sup.5, --COOR.sup.6 or CONR.sup.7 R.sup.8 or salts thereof.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: June 4, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bodo Junge, Bernd Richter, Thomas Glaser, Jorg Traber
  • Patent number: 5002957
    Abstract: Azaneophyl and silazaneophyl sulfides, processes for their preparation, agents containing them, and their use as pesticides.Compounds of the formula I, their optical isomers and mixtures thereof ##STR1## where M denotes C or Si,R.sup.1 denotes unsubstituted or substituted pyridyl, unsubstituted or substituted pyrimidyl, andwhen M=C- denotes unsubstituted or substituted pyridazinyl, unsubstituted or substituted pyrazinyl, unsubstituted or substituted 1,2,4-triazinyl, unsubstituted or substituted 1,2,4,5-tetrazinyl,R.sup.2, R.sup.3 independently or one another denote alkyl, alkenyl, haloalkyl, phenyl, or R.sup.2 and R.sup.3 denote an alkylene chain which - together with the quaternary central atom (M) - form an unsubstituted or fluorine-substituted ring having four to six ring members (when M=Si) or having three to six ring members (when M=C),R.sup.4 denotes H, F, --CN, --CCl.sub.3, --C.dbd.CH, (C.sub.1 -C.sub.4)alkyl, ##STR2## R.sup.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: March 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans H. Schubert, Gerhard Salbeck, Hans-Peter Krause, Werner Knauf, Anna Waltersdorfer, Manfred Kern
  • Patent number: 5003077
    Abstract: 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: Grant
    Filed: August 7, 1989
    Date of Patent: March 26, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Takanori Hioki, Kazuhiko Matsumoto
  • Patent number: 4996218
    Abstract: Compounds of the general formula (I) ##STR1## and physiologically acceptable salts and solvates thereof, which have .beta..sub.2 -adrenoreceptor stimulant activity. They may be used in the treatment of diseases associated with reversible airways obstruction, such as asthma and chronic bronchitis.In preferred embodiments, Q represents a chlorine atom or a trifluoromethyl group, X represents a C.sub.3-4 alkylene chain, Y a C.sub.1-5 alkylene chain, R, R.sup.1 and R.sup.2 are each preferably a hydrogen atom or a methyl group and Het represents a pyrimidinyl pyrazinyl, triazinyl, thiazolyl, quinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl or pyridyl group.
    Type: Grant
    Filed: August 10, 1988
    Date of Patent: February 26, 1991
    Assignee: Glaxo Group Limited
    Inventor: Lawrence H. C. Lunts
  • Patent number: 4980351
    Abstract: The present invention are novel 3-aminopropoxyaryl derivatives, compositions and methods of use thereof for treating congestive heart failure, coronary heart disease, or myocardial ischemia.
    Type: Grant
    Filed: November 4, 1987
    Date of Patent: December 25, 1990
    Assignee: Warner-Lambert Company
    Inventors: Hubert G. K. Barth, Ila Sircar
  • Patent number: 4968681
    Abstract: 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: Grant
    Filed: November 15, 1988
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
  • Patent number: 4960890
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4959480
    Abstract: Novel pyrazoloazole couplers comprise an aryl or heterocyclic group having, in at least one of the ortho positions to the carbon atom (A) that is bonded to the pyrazoloazole nucleus, a substituent (B) that enables the pyrazoloazole coupler to form a magenta dye that has increased stability and has absorption controllably shifted, that is shifted hypsochromically relative to a dye formed from a similar coupler lacking substituent (B). These couplers are useful in photographic silver halide materials and processes.
    Type: Grant
    Filed: March 9, 1988
    Date of Patent: September 25, 1990
    Assignee: Eastman Kodak Company
    Inventors: Sharon E. Normandin, Arlyce T. Bowne, Nigel E. Milner, David Clarke
  • Patent number: 4937255
    Abstract: 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: Grant
    Filed: March 16, 1989
    Date of Patent: June 26, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gunter Thomas
  • Patent number: 4927935
    Abstract: 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: Grant
    Filed: November 7, 1988
    Date of Patent: May 22, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Hackenberger, Manfred Patsch
  • Patent number: 4921959
    Abstract: An anthraquinone compound represented by formula: ##STR1## wherein R and X are as defined in the specification, and a polarizing film containing the same. The anthraquinone compound exhibits satisfactory compatibility with organic polymers and high dichroism, and the polarizing films have excellent performance characteristics.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: May 1, 1990
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Konoe Miura, Tetsuo Ozawa, Seigo Okumura, Shinji Kubo
  • Patent number: 4920131
    Abstract: 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: Grant
    Filed: June 21, 1988
    Date of Patent: April 24, 1990
    Assignee: Rorer Pharmaceutical Corp.
    Inventors: Fu-Chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
  • Patent number: 4920132
    Abstract: This invention relates to certain quinoline-diaryl compounds and their use as leukotriene D.sub.4 antagonists for the treatment of hypersensitive disorders.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: April 24, 1990
    Assignee: Rorer Pharmaceutical Corp.
    Inventors: Fu-chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
  • Patent number: 4920130
    Abstract: This invention relates to certain quinoline-diaryl compounds and their use as leukotriene D.sub.4 antagonists for the treatment of hypersensitive disorders.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: April 24, 1990
    Assignee: Rorer Pharamceutical Corp.
    Inventors: Fu-chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
  • Patent number: 4920133
    Abstract: This invention relates to certain quinoline-diaryl compounds and their use as leukotriene D.sub.4 antagonists for the treatment of hypersensitive disorders.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: April 24, 1990
    Assignee: Rorer Pharmaceutical Corp.
    Inventors: Fu-chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
  • Patent number: 4918081
    Abstract: 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: Grant
    Filed: June 20, 1988
    Date of Patent: April 17, 1990
    Assignee: Rorer Pharmaceutical Corp.
    Inventors: Fu-Chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
  • Patent number: 4908056
    Abstract: This invention relates to novel heterocyclic carbonyl sulfonamides which are particularly useful as agricultural chemicals.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: March 13, 1990
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Chi-Ping Tseng
  • Patent number: 4906643
    Abstract: N-(3-hydroxy-4-piperidinyl)substituted benzamides, their N-oxide forms and pharmaceutically acceptable acid-addition salts having gastrointestinal motility stimulating properties, compositions containing the same, and methods of treating warm blooded animals suffering from a decreased peristalsis of the gastrointestinal system.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: March 6, 1990
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Freddy F. Vlaeminck, Karel J. Van Loon
  • Patent number: 4900825
    Abstract: 4-Nitro-5-imidazolyl ethers and thioethers of the formula I ##STR1## where R.sup.1 is alkyl, alkoxyalkyl, cycloalkyl, aryl, aralkyl or alkylaryl, R.sup.2 is hydrogen, alkyl, cycloalkyl, aryl, aralkyl or alkylaryl, R.sup.3 is alkyl, cycloalkyl, aryl, aralkyl, alkylaryl or a heterocyclic or heteroaromatic radical or a counter-ion of the corresponding alcoholate or thiolate or, where X is sulfur, R.sup.3 is hydrogen, and X is oxygen or sulfur, and the stated organic radicals may furthermore carry substituents which are inert under the reaction conditions, are prepared by reacting a dinitroimidazole of the formula II ##STR2## with an alcohol or thiol of the formula IIIR.sup.3 --XH (III)in a solvent or diluent at a pH of the from 4 to 16.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: February 13, 1990
    Assignee: BASF Aktiengsellschaft
    Inventors: Hermann Koehler, Toni Dockner
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • Patent number: 4889935
    Abstract: There are disclosed compounds of the formula ##STR1## wherein ##STR2## R is hydrogen, lower alkyl, phenyl or benzyl; R.sup.1 is hydrogen, lower alkyl, trifluoromethyl, amino, mono- or di-lower alkylamino, nitro, hydroxy, carboxy, lower alkoxycarbonyl, lower alkoxy or halo;R.sup.2 is hydrogen or lower alkyl;and the pharmaceutically acceptable salts thereof, and their use in the treatment of psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other inflammatory conditions.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: December 26, 1989
    Assignee: American Home Products Corporation
    Inventor: John H. Musser
  • Patent number: 4888427
    Abstract: The invention provides novel amino acids and peptides containing them which comprise a dihydropyridine.revreaction.pyridinium salt-type redox system and which provide site-specific and sustained delivery of pharmacologically active peptides to the brain. These new amino acids contain a redox system appended directly or via an alkylene bridge to the carbon atom adjacent to the carboxyl carbon and may be incorporated into a peptide chain at a variety of positions, including non-terminal positions.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: December 19, 1989
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4886811
    Abstract: This invention relates to novel quinolyloxazole-2-ones which are useful as protein kinase C inhibitors, effective in the treatment of hypertension and asthma. This invention also includes a novel procedure for producing an intermediate ketone compound involving the reaction of a bromo-quinoline compound with butyl lithium and further reacting the lithiated compound with N-methyl-N-methoxyalkanamide.
    Type: Grant
    Filed: October 24, 1988
    Date of Patent: December 12, 1989
    Assignee: Merrell Dow Pharmaceuticals
    Inventors: Winton D. Jones, George P. Claxton, Richard C. Dage, Hsien C. Cheng, Phillip J. Robinson
  • Patent number: 4881966
    Abstract: The use of quinoline derivatives of the formula ##STR1## against the harmful effects of herbicidally active 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionic acid derivatives.
    Type: Grant
    Filed: March 30, 1988
    Date of Patent: November 21, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Nyffeler, Adolf Hubele
  • Patent number: 4876347
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: October 24, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4863945
    Abstract: Pyrrolobenzimidazoles of the formula: ##STR1## are useful for treatment of heart and circulatory diseases. R.sub.1 is substituted phenyl; or optionally substituted naphthyl or a five- or six-membered heterocyclic group which can be condensed with a phenyl ring to form a bicyclic radical. R.sub.2 is hydrogen, alkyl, alkenyl or cycloalkenyl; R.sub.3 is alkyl, alkenyl or hydroxyalkyl or with R.sub.2 together forms cycloakylene; or R.sub.2 and R.sub.3 together form alkylidene or cycloalkylidene. R.sub.4 is hydrogen or lower alkanoyl. X is a valency bond, alkylene, vinylene, imino or carbonylamino. T stands for two hydrogen atoms. When X is a valency bond, R.sub.1 can also be hydrogen, hydrocarbyl which may also contain oxygen, amino, sulfur, carbonyl and sulfonyl groups. When X is imino or carbonylamino or when R.sub.1 is a bicyclic radical, T can also be oxygen. The compounds also include the tautomers and physiologically acceptable salts with inorganic and organic acids.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: September 5, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
  • Patent number: 4851409
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes and inhibitors of their biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.
    Type: Grant
    Filed: February 5, 1987
    Date of Patent: July 25, 1989
    Assignee: Merck Frosst Canada Inc.
    Inventors: Robert N. Young, Robert Zamboni, Serge Leger
  • Patent number: 4826987
    Abstract: The present invention relates to compounds of formula I ##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, 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: Grant
    Filed: February 28, 1986
    Date of Patent: May 2, 1989
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
  • Patent number: 4822884
    Abstract: A process for the protection of cultivated plants against harmful effects of aggressive agricultural chemicals by the use of compounds of the formula I ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another are each hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro or cyano,R.sub.4, R.sub.5 and R.sub.6 independently of one another are each hydrogen, halogen or C.sub.1 -C.sub.3 -alkyl,A is any one of the groups --CH.sub.2 --, --CH.sub.2 --CH.sub.2 -- or --CH(CH.sub.3)--, and Z is cyano, or admidoxime which can be acylated on the oxygen atom,including acid addition salts and metal complexes thereof.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: April 18, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Hubele
  • Patent number: 4806540
    Abstract: Novel microbicidally active 1-heteroaryl-4-arylpyrazole derivatives of the formulae (I) and/or (1A) ##STR1## in which R represents hydrogen or alkyl,R.sup.1 represents halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, a radical --S(O).sub.p -alkyl which is optionally substituted in the alkyl part, nitro or optionally substituted amino, or represents a fused-on carbocyclic or heterocyclic radicalp represents the integer 0, 1 or 2,n represents an integer from 0 to 5,X represents .dbd.CH--, or represents a nitrogen atom,Y represents CO or SO.sub.2 andR.sup.2 represents hydrogen, in each case optionaly substituted alkyl, cycloalkyl or aryl or a heterocyclic radical, or represents OR.sup.3, or also represents SR.sup.3, if Y is CO,whereinR.sup.3 represents optionally substituted alkyl or aryl, orR.sup.2 represents a radical ##STR2## wherein R.sup.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: February 21, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Sasse, Gerd Hanssler, Hans-Georg Schmitt, Wilfried Paulus
  • Patent number: 4801717
    Abstract: Novel hydroxylamino derivatives of the formulaAr--ONH.sub.2 Iwherein Ar is selected from the group consisting of mono- and polycyclic aromatics and hetero-aromatics, both optionally substituted with at least one member of the group consisting of --OH, halogen, --NO.sub.2, --CN, ##STR1## --R.sub.7, --OR.sub.8, ##STR2## --SO.sub.2 R.sub.12, --SO.sub.3 R.sub.13, --COOR.sub.14, aryl of 6 to 14 carbon atoms, --OR.sub.16, --CH.sub.2 --CN and --CH.sub.2 SO.sub.2 --R.sub.15, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, R.sub.7 and R.sub.8 are optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen and cyano, R.sub.9, R.sub.10, R.sub.11, R.sub.12 and R.sub.
    Type: Grant
    Filed: June 24, 1986
    Date of Patent: January 31, 1989
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Pierre Girault, Jean-Jacques Herve, Charles-Jacques Van Assche
  • Patent number: 4792559
    Abstract: 5-aminopentanenitrile compounds of the formula: ##STR1## in which: Ar represents ##STR2## in which: R.sub.1 is hydrogen, halogen trifluoromethyl or C.sub.1 -C.sub.5 -alkoxy, andR.sub.2 and R.sub.3, which are identical or different, each are hydrogen or C.sub.1 -C.sub.5 -alkoxy or together form --O--CH.dbd.CH--O-- or --O--CH.sub.2 --O--; or together form with the phenyl ring to which they are bound a benzoxazolyl, benzothiazolyl, benzothiadiazolyl or quinolyl radical;R is C.sub.3 -C.sub.15 -alkyl or ##STR3## in which: X is S or SO.sub.2 and Z is hydrogen, chlorine or C.sub.1 -C.sub.5 -alkyl or C.sub.1 -C.sub.5 -alkoxy;R' is C.sub.1 -C.sub.5 -alkyl, andAr' represents ##STR4## in which: R'.sub.1 is C.sub.1 -C.sub.5 -alkyl andR'.sub.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl; and moreover when R is ##STR5## Ar' may be ##STR6## in which Y is C.sub.1 -C.sub.5 alkoxy andY' is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: September 25, 1986
    Date of Patent: December 20, 1988
    Assignee: ADIR et Compagnie
    Inventors: Gilbert Regnier, Yves-Michel Gargouil, Jean-Paul Vilaine
  • Patent number: 4783472
    Abstract: A compound of the general formula I; ##STR1## in which R is hydrogen or a halogen or an alkyl, alkyloxy, alkylthio, trifluoromethyl, amino, alkylamino, dialkylamino, hydroxy, cyano, carboxy, alkylsulphinyl, alkylsulphonyl, sulphamido, alkylsulphamido, dialkylsulphamido, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, phenylcarbamoyl, diphenylcarbamoyl, pyridylcarbamoyl, dipyridylcarbamoyl, benzyl, alkylcarbonyl, benzoyl, alkyloxycarbonyl, phenoxycarbonyl, alkylcarbonyloxy, benzoyloxy, alkylcarbonylamino, benzamido, phenyl, phenoxy or phenylthio group, X is oxygen or sulphur or an imino, alkylimino, phenylimino, benzylimino, sulphinyl, sulphonyl, carbonyl, carbonylmethylene, methylenecarbonyl, carbonylvinylene or vinylenecarbonyl group, or X represents a valency bond or a straight-chain alkylene group containing 1 to 4 carbon atoms and Ar is a phenyl, naphthyl, pyridyl, quinolinyl, isoquinolinyl, thienyl, benzothienyl, thieno[3,2-b]thien-2-yl or thieno[2,3-b]thien-2-yl group, it being possible for the group Ar to
    Type: Grant
    Filed: July 2, 1987
    Date of Patent: November 8, 1988
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Louis Fabre, Claude James, Daniel Lave
  • Patent number: 4778802
    Abstract: The invention relates to compounds of formula ##STR1## or a salt thereof, wherein .dbd.X-- is .dbd.CH-- or .dbd.N--, R and R.sup.1 independently represent hydrogen, halogen or lower alkoxy and R.sup.2 is hydrogen or a substituent selected from halogen, lower alkyl, lower alkoxy or halolower alkyl which compounds exhibit psychotropic activity and are useful as antidepressants.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: October 18, 1988
    Assignee: John Wyeth & Brother, Ltd.
    Inventors: John L. Archibald, Terence J. Ward
  • Patent number: 4769461
    Abstract: There are disclosed compounds of the formula ##STR1## wherein W represents a covalent bond or ##STR2## X is N or CR.sup.2 ; Y is O, S, NR.sup.2 or C(R.sup.2).sub.2 when n=0, or N or CR.sup.2 when n=1Z is ##STR3## R.sup.1 is hydrogen, lower alkyl, trifluoromethyl, nitro, hydroxy, lower alkoxy, mercapto, loweralkylthio or halo;R.sup.2 is hydrogen or lower alkyl;n is 0-1;m is 1-6 with the proviso that m is 0-5 when W represents a covalent bond;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, in psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other immediate hypersensitivity reactions.
    Type: Grant
    Filed: September 16, 1986
    Date of Patent: September 6, 1988
    Assignee: American Home Products Corporation
    Inventors: John H. Musser, Dennis M. Kubrak
  • Patent number: 4757079
    Abstract: Novel compounds of the formula: ##STR1## are described wherein Z is a bicyclic aryl group containing between 9 and 10 ring atoms, up to two of which may be nitrogen and up to one of which may be oxygen or sulfur; A is an ethenyl group which may be lower-alkyl-substituted; and R and R' each represent H or an aliphatic group of 1-4 carbon atoms; or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: June 24, 1986
    Date of Patent: July 12, 1988
    Assignee: Dynamac Corporaton
    Inventor: Allan P. Gray
  • Patent number: 4751309
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: June 14, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4751233
    Abstract: Novel 8-thiotetrahydroquinolines of the formula ##STR1## wherein X is selected from the group consisting of ##STR2## Alk is alkyl of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 are Alk individually selected from the group consisting of hydrogen and aryl or taken together with the carbon atoms to which they are attached form a phenyl optionally substituted with at least one member of the group consisting of alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, halogen, ##STR3## and Alk' is alkyl of 1 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antiallergic activity and their preparation.
    Type: Grant
    Filed: February 26, 1986
    Date of Patent: June 14, 1988
    Assignee: Roussel Uclaf
    Inventors: Stephen Clements-Jewery, Peter D. Kennewell, Robert Westwood
  • Patent number: 4727149
    Abstract: Nitriles of fused ring pyridine compounds such as 5,6,7,8-tetrahydroquinolines are prepared from metal derivatives of the starting compounds such as 8-litho-5,6,7,8-tetrahydroquinolines which have been prepared by treating a 5,6,7,8-tetrahydroquinoline with a metal amide prepared in situ from a metal alkyl and an N-benzylidine-N-alkylamine.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: February 23, 1988
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shepherd
  • Patent number: 4707552
    Abstract: Nitriles and thioamides of fused ring pyridine compounds such as 5,6,7,8-tetrahydroquinolines are prepared from metal derivatives of the starting compounds such as 8-lithio-5,6,7,8-tetrahydroquinolines which have been prepared by treating a 5,6,7,8-tetrahydroquinoline with a metal amide prepared in situ from a metal alkyl and an N-benzylidine-N-alkylamine.
    Type: Grant
    Filed: September 18, 1985
    Date of Patent: November 17, 1987
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shepherd
  • Patent number: 4704390
    Abstract: Novel phenyl and heterocyclic tetrahydropyridyl and piperazinyl alkoxy benzheterocyclic compounds are described which have valuable neuroleptic properties by virtue of their dopamine autoreceptor agonist activity. Methods of preparation, pharmaceutical compositions, and methods for treating psychoses, such as schizophrenia, are also described.
    Type: Grant
    Filed: November 5, 1986
    Date of Patent: November 3, 1987
    Assignee: Warner-Lambert Company
    Inventors: Bradley W. Caprathe, Horace A. DeWald, Juan C. Jaen, Lawrence D. Wise
  • Patent number: 4677210
    Abstract: Z is a chemical bond or an alkylene chain containing up to 5 carbons in the principal chain and up to a total of 7 carbons;X is O or S;R and R.sub.1 are independently hydrogen, hydroxy, lower alkoxy, lower alkanoyloxy, halo, cyano, carboloweralkoxy, carboxyloweralkyl, aryloxy or benzyloxy;R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl, lower aralkyl, lower alkenyl, lower alkynyl, aryl or carboxyloweralkyl;and pharmaceutically acceptable salts thereof have pharmaceutical activity, particularly as lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic properties.
    Type: Grant
    Filed: June 19, 1985
    Date of Patent: June 30, 1987
    Assignee: Rorer Pharmaceutical Corporation
    Inventor: Fu-chih Huang
  • Patent number: 4647557
    Abstract: This invention relates to novel heterocyclic derivatives bearing an amino group and to processes for making said compounds.More particularly this invention provides novel heterocyclic compounds the hetero ring of which has two hetero atoms, the same or different, substituted with a free or substituted amino group.These compounds are useful as active ingredients of drugs.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: March 3, 1987
    Inventors: Gerard Moinet, Michel Schaeffer, Pierre Bessin, Jacqueline Bonnet
  • Patent number: 4629733
    Abstract: The present invention relates to novel indolinones of the general formula ##STR1## wherein R represents an aryl group having from 6 to 10 carbon atoms, unsubstituted or mono- or disubstituted by alkyl groups having from 1 to 5 carbon atoms, hydroxyl groups, alkoxy groups having from 1 to 3 carbon atoms, or halogen atoms, whereby the substituents may be the same or different and whereby the phenyl nucleus of the aryl group may also be substituted by an amino group, a hydroxyl group, or an alkanoylamino group with altogether from 1 to 3 carbon atoms; an aryl group having from 6 to 10 carbon atoms, substituted by 3 or 4 alkyl groups having from 1 to 5 carbon atoms each; a phenyl group substituted by a phenyl, halogenphenyl, or cycloalkyl group with 5 to 7 carbon atoms; an aralkyl group having from 7 to 11 carbon atoms; or a pentamethylphenyl, pyridyl, or quinolyl group; m represents the number 0, 1, or 2; and n represents the number 2, 3, 4, 5, or 6.
    Type: Grant
    Filed: July 27, 1984
    Date of Patent: December 16, 1986
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Erich Muller, Josef Nickl, Josef Roch, Berthold Narr