Unsaturated Carbocyclic Ring Attached Directly To The Quinoline Ring System By Nonionic Bonding (e.g., Quinophthalones, Etc.) Patents (Class 546/173)
  • Patent number: 5541223
    Abstract: Novel podophyllotoxin compounds and their use in treating tumors are disclosed. The analogs have the general formula: ##STR1## wherein NH--R is a selected aryl amine, dialkylaminoalkyleneamino, or dialkylaminoanilino group.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: July 30, 1996
    Assignees: Yale University, The University of North Carolina at Chapel Hill
    Inventors: Kuo-Hsiung Lee, Yung-Chi Cheng
  • Patent number: 5529978
    Abstract: Certain N-acetonyl-substituted-amides of the formula: ##STR1## wherein A is a heterocycle, a phenylalkyl, a phenylalkoxy, naphthyl, cycloalkyl, alkoxyalkyl, alkyl, haloalkyl or alkenyl group; X, Y and Z are selected from the group consisting of hydrogen, halo, cyano, thiocyano, isothiocyano, methylsulfonyloxy, thio(C.sub.1 -C.sub.2)alkyl, (C.sub.1 -C.sub.2)alkoxy, carbamoyl, dithiocarbamoyl, hydroxy, azide, trifluoromethylcarboxy, (C.sub.1 -C.sub.4)alkylcarbonyloxy, phenylcarbonyloxy, phenoxy, thiophenyl, imidazolyl or triazolyl group as described herein; R.sup.1 and R.sup.2 are each independently a hydrogen atom or a (C.sub.1 -C.sub.6)alkyl group; and compositions containing these amides are fungicidally active, particularly against phytopathogenic fungi.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: June 25, 1996
    Assignee: Rohm and Haas Company
    Inventor: Ashok K. Sharma
  • Patent number: 5527955
    Abstract: The invention concerns a method for treating depression or senile dementia using a compound which acts selectively as an agonist of gamma aminobutyric acid (GABA) at GABA autoreceptors with the proviso that the compound is not fengabine and progabide.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: June 18, 1996
    Assignee: John Wyeth & Brother, Limited
    Inventors: Michael C. W. Minchin, John F. White
  • Patent number: 5523312
    Abstract: Disclosed herein are compounds and pharmaceutical compositions useful for combating picornaviruses and preventing or treating picornaviral infections. The compounds have the formula: ##STR1## wherein Het.sub.1 is chosen from the group consisting of oxazolyl, isoxazolyl, oxadiazolyl;Y is an alkylene bridge of 3 to 9 carbon atoms;Het.sub.2 is benzofuranyl or indolyl;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, acetyl, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinyl alkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluromethyl, or cyano; andR.sub.3 is oxazolyl, oxadiazolyl, isoxazolyl or any of these substituted with alkyl, halo, alkoxyalkyl, cycloalkyl, haloalkyl, hydroxyalkyl, alkoxy, hydroxy, furyl, thienyl, or fluoroalkyl;the N-oxide thereof or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: June 4, 1996
    Assignee: Sterling Winthrop Inc.
    Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Gee-Hong Kuo, Theodore J. Nitz, Michael Reuman
  • Patent number: 5519022
    Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: November 10, 1993
    Date of Patent: May 21, 1996
    Assignees: Imperial Chemical Industries Plc, ICI Pharma
    Inventors: Philip N. Edwards, David Waterson
  • Patent number: 5514804
    Abstract: A diastereomer salt of optically active quinolinemevalonic acid of the formula ((-)I.multidot.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: May 7, 1996
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Yoshio Ohara, Mikio Suzuki, Yoshinobu Yanagawa, Hiroshi Iwasaki, Nobuhide Miyachi
  • Patent number: 5492915
    Abstract: This invention relates to compounds having selective LTB.sub.4 antagonist properties. Therapeutic compositions comprising said compounds and methods for the treatment of disorders involving LTB.sub.4 agonist-mediated activity utilizing said compositions wherein the compounds are described by the formula ##STR1## wherein R.sub.4, X, R, Y, R', Q, m and n are herein defined, and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: February 20, 1996
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Norbert Dereu, Wolfram Hendel, Richard Labaudiniere
  • Patent number: 5482942
    Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5478832
    Abstract: 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: Grant
    Filed: May 4, 1993
    Date of Patent: December 26, 1995
    Assignees: 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
  • Patent number: 5476941
    Abstract: A compound of formula (1): ##STR1## in which R.sub.1 represents a 1,1-dimethylethyl, triphenylmethyl, methoxymethyl or benzyloxymethyl group; andR.sub.2 represents a C.sub.1 -C.sub.4 alkyl group.
    Type: Grant
    Filed: October 3, 1994
    Date of Patent: December 19, 1995
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Jose Ruiz-Montes, Guy Rossey
  • Patent number: 5473075
    Abstract: A diastereomer salt of optically active quinolinemevalonic acid of the formula ((-)I.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: December 5, 1995
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Yoshio Ohara, Mikio Suzuki, Yoshinobu Yanagawa, Hiroshi Iwasaki, Nobuhide Miyachi
  • Patent number: 5468862
    Abstract: A process for the manufacture of a quinophthalone, in particular Solvent Yellow 33 (D & C Yellow 11) is described. The quinophthalone, in particular Solvent Yellow 33, is made by a process in which quinaldine is condensed with a molar excess of either phthalic acid or phthalic anhydride, the acid or anhydride being employed not only as a reactant, but also as a solvent for the reaction. This process can also employ phthalic acid (or recycled phthalic acid) and phthalic anhydride together, one as the solvent and the other as the reactant.
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: November 21, 1995
    Assignee: Warner-Jenkinson Company
    Inventor: Puthalath K. Sujeeth
  • Patent number: 5463067
    Abstract: Intermediates of structural formula ##STR1## can be made by reacting glycidol or an activated derivative thereof with an amide. The process and intermediates are useful for synthesizing HIV protease inhibitor compounds.
    Type: Grant
    Filed: January 26, 1994
    Date of Patent: October 31, 1995
    Assignee: Merck & Co., Inc.
    Inventors: David Askin, Kan K. Eng, Ralph P. Volante
  • Patent number: 5457112
    Abstract: 3-(6-Quinolylmethyl)-4H-imidazol-4-one derivatives corresponding to the formula (I): ##STR1## in which R.sub.1 represents an unbranched or branched (C.sub.2 -C.sub.5) alkyl group,R.sub.2 and R.sub.3 represent, each independently of one another, either a hydrogen atom, or an unbranched or branched (C.sub.1 -C.sub.5)alkyl group, or a (CH.sub.2).sub.n -aryl group where n=0 to 3, or R.sub.2 and R.sub.3 with the imidazole ring can form a spirocyclo(C.sub.3 -C.sub.8)alkyl group,as well as their addition salts with pharmaceutically acceptable acids and bases.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: October 10, 1995
    Assignee: Synthelabo
    Inventors: Gerard Cremer, Jean Claude Muller
  • Patent number: 5455252
    Abstract: A compound of the formula ##STR1## wherein: R.sup.1 is independently selected from hydrogen, lower-alkyl, cycloalkyl, cycloalkyl lower-alkyl, lower-alkoxy, formyl, (lower-alkyl)-hydroxylmethyl, aryl, benzyl, arylmethyl, pyridylmethyl,where aryl, benzyl, arylmethyl and pyridylmethyl are unsubstituted or independently mono, di or tri substituted with hydrogen, hydroxy, thiol, amino, halo, nitro, lower-alkylthio, lower-alkoxy, mono-lower-alkylamino, di-lower-alkylamino, hydroxycarbonyl, lower-alkoxycarbonyl, hydroxysulfonyl, lower-alkoxysulfonyl, lower-alkylsulfonyl, lower-alkylsulfinyl, trifluoromethyl, cyano, tetrazoyl, carbamoyl, lower-alkylcarbamoyl, and di-lower-alkylcarbamoyl; andR.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as set forth in the specification.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: October 3, 1995
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Robert S. Wilhelm, Paul R. Fatheree, Ronnie L. Chin
  • Patent number: 5455253
    Abstract: Compounds of formula I ##STR1## wherein R.sup.2, R.sup.3, R.sup.4, R.sup.10 and R.sup.11 have any of the meanings given in the specification, and their pharmaceutically acceptable salts are useful in the treatment of urinery incontinence. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: October 3, 1995
    Assignee: Zeneca Limited
    Inventors: Cyrus J. Ohnmacht, Jr., Diane Trainor, Janet M. Forst, Mark M. Stein, Robert J. Harris
  • Patent number: 5436247
    Abstract: A compound represented by the general formula: ##STR1## wherein Y represents a nitrogen atom or C--G (G represents a carboxyl group which may be esterified); ring R is a nitrogen-containing unsaturated heterocyclic group which may be substituted or unsubstituted; each of rings A and B may have a substituent; n represents an integer from 1 to 4; k represents the integer 0 or 1, or a salt thereof, which serves well as an anti-inflammatory agent, particularly a therapeutic agent for arthritis.
    Type: Grant
    Filed: January 26, 1994
    Date of Patent: July 25, 1995
    Assignee: Takeda Chemical Industries
    Inventors: Takashi Sohda, Haruhiko Makino, Atsuo Baba
  • Patent number: 5434162
    Abstract: Compounds characterized as quinolinyl- or isoquinolinyl-terminated alkylamino ethynyl alanine amino diol derivatives are useful as renin inhibitors for the treatment of hypertension and are of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 ; X is selected from oxygen atom and methylene; G is a quinolinyl or isoquinolinyl group; R.sub.1 is selected from hydrido, methyl, ethyl, isopropyl and n-propyl; R.sub.2 is phenylmethyl; each of R.sub.3 and R.sub.5 is hydrido; R.sub.4 is--(CH.sub.2).sub.q --C--V;V is selected from hydrido and methyl; R.sub.6 is cyclohexylmethyl; R.sub.7 is selected from isobutyl, cyclopropyl and cyclopropylmethyl; q is a number selected from zero through three, inclusive; and n is a number selected from zero through three, inclusive; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: July 18, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, Robert E. Manning
  • Patent number: 5432283
    Abstract: The present invention provides a compound which is a quinoline derivative of the formula (I) ##STR1## in which R.sub.1 represents either 1H-tetrazol-5-yl, or CO.sub.2 H,R.sub.2 represents either (C.sub.1-7)alkyl or (C.sub.2-6)alkenyl,R.sub.3 and R.sub.4 represent, independently of each other, hydrogen, halogen, cyano group, (C.sub.1-7)alkyl, (C.sub.3-7)cycloalkyl(C.sub.1-4)alkyl, aryl, aryl(C.sub.1-4)alkyl, aryl(C.sub.2-6)alkenyl, --(CH.sub.2).sub.m --COR.sub.5 in which m=0 to 4 and R.sub.5 represents hydrogen, --OH, --(C.sub.1-6)alkoxy, or --NR.sub.7 R.sub.8, R.sub.7 and R.sub.8 representing, independently of each other, hydrogen or --(C.sub.1-4)alkyl group, or a --(CH.sub.2).sub.n --R.sub.6 group in which n=1 to 4 and R.sub.6 represents --OH, --(C.sub.1-6)alkoxy, --(C.sub.1-4)alkoxy(C.sub.1-4)alkoxy, or (C.sub.3-7)cycloalkyl(C.sub.1-4)alkoxy group, or a pharmaceutically acceptable salt thereof and their therapeutic applications.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: July 11, 1995
    Assignee: Synthelabo
    Inventors: Gerard Cremer, Pascale Goberville, Jean-Claude Muller
  • Patent number: 5416117
    Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
  • Patent number: 5356891
    Abstract: The present invention relates to compounds having anti-ischaemic activity of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and Z are as defined herein. The present invention further relates to a method of preparing such compounds, as well as compositions having anti-ischaemic activity which comprise such compounds and a method of treating ischaemia.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: October 18, 1994
    Inventors: Donald T. Witiak, Ineke van Wijngaarden, Raghunathan V. Nair, Josephus H. M. Lange, Jacobus A. J. den Hartog
  • Patent number: 5328909
    Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: July 12, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
  • Patent number: 5326759
    Abstract: Novel 9-amino-7-(substituted amino)-6-demethyl-6-deoxytetracyclines having activity against a wide spectrum of organisms including organisms which are resistant to tetracyclines are disclosed. Also disclosed are intermediates and methods for making the novel compounds of the present invention.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: July 5, 1994
    Assignee: American Cyanamid Company
    Inventors: Joseph J. Hlavka, Phaik-Eng Sum, Yakov Gluzman, Ving J. Lee
  • Patent number: 5306820
    Abstract: (Quinolin-2-yl-methoxy)phenylacetic acids are known as inhibitors of enzymatic reactions in the context of arachidonic acid metabolism.Enantiomerically pure (quinolin-2-yl-methoxy)phenylacetic acids can be prepared in a simple manner and in high purity and yield by diastereoselective alkylation of corresponding (quinolin-2-yl-methoxy)phenylacetic acid menthyl esters and subsequent specific removal of the ester radical with acids.
    Type: Grant
    Filed: April 10, 1992
    Date of Patent: April 26, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Matthias Decker, Klaus-Helmut Mohrs, Siegfried Raddatz
  • Patent number: 5284953
    Abstract: A diastereomer salt of optically active quinolinemevalonic acid of the formula ((-)I.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: February 8, 1994
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Yoshio Ohara, Mikio Suzuki, Yoshinobu Yanagawa, Hiroshi Iwasaki, Nobuhide Miyachi
  • Patent number: 5283250
    Abstract: Non-peptidyl compounds characterized generally as quinolinyl/quinolinylalkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; and wherein R.sub.7 is isobutyl or ethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: February 1, 1994
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5276154
    Abstract: The present invention provides optically active esters of 7-substituted 3,5-difunctionalized 6-heptenoic acids represented by the following formula: ##STR1## wherein R is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group or a substituted vinyl group;Ar is a condensed aromatic group;X.sup.1 and Y.sup.1 are not the same and each is a hydrogen atom or a hydroxyl group, or may be combined to represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X.sup.1 and Y.sup.1 are attached; andX.sup.2 and Y.sup.2 are not the same and each is a hydrogen atom or a hydroxyl group, or may be combined to represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X.sup.2 and Y.sup.2 are attached,or enantiomers thereof.The present invention further provides processes for preparing the above optically active esters and 7-substituted (3R, 5S, 6E)-3,5-dihydroxy-6-hepten-1,5-olides.
    Type: Grant
    Filed: August 21, 1991
    Date of Patent: January 4, 1994
    Assignee: Sagami Chemical Research Center
    Inventors: Tamejiro Hiyama, Tatsuya Minami, Takeshi Hanamoto, Guntoori B. Reddy
  • Patent number: 5268380
    Abstract: (1H-azol-1-ylmethyl)substituted quinoline derivatives, compositions containing the same, and methods of treating mammals suffering from disorders which are characterized by an increased proliferation and/or abnormal differentiation of epithelial tissues.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: December 7, 1993
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Gerard C. Sanz, Marc G. Venet, Eddy J. E. Freyne, Alfons H. M. Raeymakers
  • Patent number: 5243052
    Abstract: A mixed carbonate ester of a quinophthalone dye and a tertiary alkanol containing not more than about 9 carbon atoms, preferably a compound of the formula: ##STR1## wherein X is a sulfur atom or a carbonyl group; each Y independently is a hydrogen atom, a halogen atom, a --CO--OR.sup.4 or a --CO--NHR.sup.4 group, wherein R.sup.4 is an alkyl group containing not more than about 10 carbon atoms; R is a hydrogen atom or an --O--C(.dbd.O)--O--CR.sup.5 R.sup.6 R.sup.7 group; and R.sup.1, R.sup.2, R.sup.3, R.sup.5, R.sup.6 and R.sup.7 are each an alkyl group, subject to the proviso that R.sup.1, R.sup.2 and R.sup.3 together contain a total of not more than about 8 carbon atoms, and R.sup.5, R.sup.6 and R.sup.7 together contain a total of not more than about 8 carbon atoms.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: September 7, 1993
    Assignee: Polaroid Corporation
    Inventors: Lloyd D. Taylor, David P. Waller
  • Patent number: 5204344
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.
    Type: Grant
    Filed: February 5, 1991
    Date of Patent: April 20, 1993
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Petpiboon Prasit, Rejean Fortin, John H. Hutchinson, Michel L. Belley, Serge Leger, John Gillard, Richard Frenette
  • Patent number: 5192771
    Abstract: For inhibiting lipoxygenzce, (quinolin-2-yl-methoxy) phenylacetic acid derivatives containing cyclic substituents of the formula ##STR1## in which A, Q, D, E, G, T and M are hydrogen or various radicals,R.sup.3 is halogen or an alkyl or phenyl radical, andR.sup.1 and R.sup.2 complete a carbocyclic ring which may be substituted and/or fused to another ring,and salts thereof.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: March 9, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Mohrs, Siegfried Raddatz, Romanis Fruchtmann, Christian Kohlsdorfer, Reiner Muller-Peddinghaus, Pia Theisen-Popp
  • Patent number: 5189165
    Abstract: A process for preparing a compound I ##STR1## with A=t-butyl, aryl andR=alkyl, alkenyl, alkynyl, alkenynyl, cycloalkyl(alkyl), aryl, arylalkyl, alkyl-S-(-O)-arylby reacting a compound III ##STR2## with a compound IV ##STR3## under the conditions of a phase-transfer reaction, is described. The process gives excellent yields and is not associated with the unpleasant odor of mercaptans.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Burdinski, Reinhard Kirsch, Hariolf Kottmann
  • Patent number: 5185328
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are independently hydrogen, C.sub.1-6 alkyl, C.sub.1-6 cycloalkyl, C.sub.1-3 alkoxy, n-butoxy, i-butoxy, sec-butoxy, R.sup.7 R.sup.8 N-- (wherein R.sup.7 and R.sup.8 are independently hydrogen or C.sub.1-3 alkyl), trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoro, chloro, bromo, phenyl, phenoxy, benzyloxy, hydroxy, trimethylsilyloxy, diphenyl-t-butylsilyloxy, hydroxymethyl or --O(CH.sub.2).sub.l OR.sup.19 (wherein R.sup.19 is hydrogen or C.sub.1-3 alkyl, and l is 1,2 or 3); or when located at the ortho position to each other, R.sup.1 and R.sup.2, or R.sup.3 and R.sup.4 together form --CH.dbd.CH--CH.dbd.CH--; or when located at the ortho position to each other, R.sup.1 and R.sup.2 together form --OC(R.sup.15 l) (R.sup.16)O-- (wherein R.sup.15 and R.sup.16 are independently hydrogen or C.sub.1-3 alkyl); Y is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 --CH.dbd.CH-- or -- CH.dbd.CH--CH.sub.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: February 9, 1993
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Yoshihiro Fukikawa, Mikio Suzuki, Hiroshi Iwasaki, Mitsuaki Sakashita, Masaki Kitahara
  • Patent number: 5180836
    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: November 1, 1991
    Date of Patent: January 19, 1993
    Assignee: Nippon Chemiphar Co., Ltd.
    Inventors: Susumu Okabe, Mitsuo Masaki, Tomio Yamakawa, Hitoshi Matsukura, Yutaka Nomura
  • Patent number: 5166210
    Abstract: Quinolinyl styryl compounds and their use as pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties.
    Type: Grant
    Filed: July 2, 1991
    Date of Patent: November 24, 1992
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Fu-Chi Huang, Robert A. Galemmo, Jr., Henry F. Campbell
  • Patent number: 5112832
    Abstract: The invention concerns compounds of formula I ##STR1## or a salt thereof, wherein R.sup.1 and R.sup.2 each independently represent hydrogen, lower alkyl, lower alkoxy, carboxyloweralkyl, carboxy, hydroxyloweralkyl, halogen, haloloweralkyl, lower alkoxycarbonyl, optionally substituted aryl or optionally substituted aralkyl, n represents an integer from 3 to 6; R.sup.3 represents hydrogen or single or multiple substitution on one or more of the aliphatic carbons by one or more substituents selected from lower alkyl, optionally substituted aryl and optionally substituted aralkyl; A represents a group of formula (i) or (ii) below:--CR.sup.4 R.sup.5 --(CR.sup.6 R.sup.7).sub.m -- (i)--CX--(CR.sup.6 R.sup.7).sub.m -- (ii)in which R.sup.4, R.sup.6 and R.sup.7 each independently represent hydrogen or lower alkyl (providing that when R.sup.5 is NH.sub.2, R.sup.0 is hydrogen); m is 0 or 1; R.sup.5 represents hydrogen, NH.sub.2, OH or loweralkoxy, and X is .dbd.O, .dbd.NH or .dbd.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: May 12, 1992
    Assignee: John Wyeth & Brother Limited
    Inventors: Roger Crossley, Albert Opalko, Robin G. Shepherd
  • Patent number: 5110347
    Abstract: The invention relates to certain substituted fused compounds of Formula I ##STR1## which are useful as herbicides, and their agriculturally suitable compositions, as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.
    Type: Grant
    Filed: November 26, 1990
    Date of Patent: May 5, 1992
    Assignee: E. I Du Pont de Nemours and Company
    Inventor: Thomas Selby
  • Patent number: 5106980
    Abstract: A process for the preparation of a quinophthalone of the formula ##STR1## in which X is hydrogen, chlorine or bromine and n is an integer from 1 to 4, by condensing 8-aminoquinaldine with a phthalic anhydride, optionally monosubstituted or polysubstituted by chlorine or bromine, in the presence of molten benzoic acid acting as diluent.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: April 21, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Burkhard Ort, Guido Kuth
  • 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: 5081126
    Abstract: The invention relates to dithioacetal compounds having 5-lipoxygenase-inhibiting activity, of the formula: ##STR1## wherein R.sup.1 is lower alkyl, di-(lower)alkylamino, aryl, or heterocyclic group which may have one or more substitutents selected from halogen, lower alkyl, lower alkoxy and phenyl,R.sup.2 and R.sup.3 are each lower alkyl, aryl or ar-(lower)alkyl, or R.sup.2 and R.sup.3 are together to form 1,3-dithian ring,R.sup.4 is hydrogen or lower alkoxy, andn is 0 or an integer 1 to 4 and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: January 14, 1992
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Teruo Oku, Yoshio Kawai, Hiroshi Kayakiri, Kazuyoshi Kuratani, Masashi Hashimoto
  • Patent number: 5071987
    Abstract: Quinoline-4-carboxylic acids derivatives are useful as dye-forming components for pressure- and heat-sensitive recording materials and have of the general formula I ##STR1## where one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen while the other two are each independently of each other hydrogen, fluorine, chlorine, bromine, linear or branched C.sub.1 -C.sub.5 -alkyl, hydroxyl, C.sub.1 -C.sub.10 -alkoxy, which may be interrupted in the alkyl by 1 or 2 oxygen atoms, or is ##STR2## R.sup.7 is hydrogen, methyl or ethyl and R.sup.8 is C.sub.1 -C.sub.4 -alkanoyl, benzoyl, p-chlorobenzoyl, C.sub.1 -C.sub.6 -alkyl, benzyl or p-chlorobenzyl, orR.sup.1 and R.sup.2 together are a fused-on benzene ring,R.sup.2 and R.sup.3 together are unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted methylenedioxy or ethylenedioxy,R.sup.4 is hydroxyl, C.sub.1 -C.sub.10 -alkoxy, which may be interrupted by 1-4 oxygen atoms, or unsubstituted or chlorine-substituted phenyl-C.sub.1 -C.sub.2 -alkoxy,R.sup.5 is hydroxyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: December 10, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Raulfs, Udo Mayer
  • Patent number: 5047417
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydrogen or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: September 10, 1991
    Assignee: Eisai Co. Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • 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: 5026854
    Abstract: The invention concerns compounds of formula I ##STR1## or a salt thereof, wherein R.sup.1 and R.sup.2 each independently represent hydrogen, lower alkyl, lower alkoxy, carboxyloweralkyl, carboxy, hydroxyloweralkyl, halogen, haloloweralkyl, lower alkoxycarbonyl, optionally substituted aryl or optionally substituted aralkyl, n represents an integer from 3 to 6; R.sup.3 which is optionally present represents single or multiple substitution on one or more of the aliphatic carbons by one or more substituents selected from lower alkyl, optionally substituted aryl and optionally substituted aralkyl; A represents a group of formula (i) or (ii) below:--CR.sup.4 R.sup.5 --(CR.sup.6 R.sup.7).sub.m -- (i)--CX--(CR.sup.6 R.sup.7).sub.m -- (ii)in which R.sup.4, R.sup.6 and R.sup.7 each independently represent hydrogen or lower alkyl (providing that when R.sup.5 is NH.sub.2, R.sup.4 is hydrogen); m is 0 or 1; R.sup.5 represents hydrogen, NH.sub.2, OH or loweralkoxy, and X is .dbd.O, .dbd.NH or .dbd.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: June 25, 1991
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shepherd
  • Patent number: 5017583
    Abstract: 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: Grant
    Filed: February 23, 1988
    Date of Patent: May 21, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
  • Patent number: 5011930
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are independently hydrogen, C.sub.1-6 alkyl, C.sub.1-6 cycloalkyl, C.sub.1-3 alkoxy, n-botoxy, i-botoxy, sec-butoxy, R.sup.7 R.sup.8 N-- (wherein R.sup.7 and R.sup.8 are independently hydrogen or C.sub.1-3 alkyl), trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoro, chloro, bromo, phenyl, phenoxy, benzyloxy, hydroxy, trimethylsilyloxy, diphenyl-t-butylsilyloxy, hydroxymethyl or --O(CH.sub.2).sub.l OR.sup.19 (wherein R.sup.19 is hydrogen or C.sub.1-3 alkyl, and l is 1,2 or 3); or when located at the ortho position to each other, R.sup.1 and R.sup.2, and R.sup.3 and R.sup.4 together form --CH.dbd.CH--CH.dbd.CH--; or when located at the ortho position to each other, R.sup.1 and R.sup.2 together form --OC(R.sup.15)(R.sup.16)O-- (wherein R.sup.15 and R.sup.16 are independently hydrogen or C.sub.1-3 alkyl); Y is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 CH.dbd.CH-- or --CH.dbd.CH-- CH.sub.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: April 30, 1991
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Yoshihiro Fujikawa, Mikio Suzuki, Hiroshi Iwasaki, Mitsuaki Sakashita, Masaki Kitahara
  • Patent number: 5008276
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: April 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • 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: 4943310
    Abstract: The invention relates to new 4-benzoyl-3-hydroxy-5-oxo-3-cyclohexenecarboxylic acid derivatives of general formula I ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.2 and R.sup.3 have the meanings given in the description, and their use as plant growth regulants.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: July 24, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Alfred Angermann, Helga Franke, Gerhard Johann
  • Patent number: 4940705
    Abstract: N-substituted derivatives of 1-desoxynojirimycin and 1-desoxymannojirimycin of the formula ##STR1## in which one of R and R' are hydroxyl and the other is hydrogenn is a number from 1 to 6R.sup.1 is hydrogen, alkyl or benzyl andR.sup.2 is alkyl which is optionally substituted by an optionally substituted aryl or by pyridyl, thienyl, furyl, pyrimidyl, pyrazinyl or quinolyl or R.sub.1 is cycloalkyl or R.sup.2 is optionally substituted by aryl or R.sup.2 is a saturated bridged heterocycle or R.sup.1 and R.sup.2 together can form a heterocyclic ring which is optionally substituted. These compounds are useful in the treatment of and prophylaxis of viral infections.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: July 10, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Boshagen, Bodo Junge, Arnold Paessens, Matthias Schuller