The Chalcogen, X, Is In A -c(=x)- Group Patents (Class 546/340)
  • Patent number: 5225436
    Abstract: Certain aryl substituted naphthalene, benzoxepine, benzazepine and henzocycloheptene derivatives are disclosed. The compounds are useful in treating hyperproliferative skin disease, allergic reactions and inflammation.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: July 6, 1993
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
  • Patent number: 5223518
    Abstract: This invention relates to 1-phenyl-3-aryl-2-propyne-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: June 29, 1993
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Robert J. Dinerstein, Jeffrey S. Sabol, Keith A. Diekema
  • Patent number: 5214027
    Abstract: Described is pyridine derivatives defined according to one of generic formula (I) ##STR1## wherein R.sup.2 represents isopropenyl group when R.sup.1 is methyl or ethyl group, R.sup.2 represents isopropenyl or acetyl group when R.sup.1 is isopropenyl group, R.sup.2 represents methyl group when R.sup.1 is isopropyl group and R.sup.2 represents isopropenyl, or isopropyl group when R.sup.1 is acetyl group; and perfumery composition containing the derivatives.
    Type: Grant
    Filed: April 3, 1992
    Date of Patent: May 25, 1993
    Assignees: Shiono Koryo Kaisha, Ltd., Lion Corporation
    Inventors: Masakazu Ishihara, Tomoyuki Tsuneya, Minoru Shiga, Hiroshi Sato, Fumio Yoshida, Keiichi Yamagishi
  • Patent number: 5214151
    Abstract: The present invention relates to a method for the preparation of .alpha., .beta.-unsaturated ketones represented by general formula (II) ##STR1## (where R is a heterocyclic group with nitrogen atom in the ring or a phenyl group with electron donative substituents) which comprises reacting aldehydes represented by general formula (I)RCHO (I)(where R is a s defined above) with acetone, in the presence as a catalyst of one or tow or more compounds selected from the group consisting of perhydroisoindole and pyrrolidine which may have substituents, in a water solvent, at 20.degree. C. to 40.degree. C., and then reacting at the reflux temperature.The compound (II) is extremely important as an intermediate for pharmaceuticals and agricultural chemicals.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: May 25, 1993
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Masashi Nakajima, Tadashi Kyotani, Keiichi Tsukashima
  • Patent number: 5212316
    Abstract: Compounds of formula I ##STR1## wherein Ar is an optionally substituted phenyl ring; B is a single bond, a group --(CH.sub.2 OCH.sub.2).sub.n being n=or 2, a a 2,4-disubstituted-1,3-dioxolane ring or a 2,4-disubstituted-1,3-thioxolane ring, R is a single bond, an optionally substituted methylene or ethylene group and T is 2, 3- or 4-pyridyl, an optionally salified or esterified carboxy group or a carboxyamide group. Said compounds are useful in treatment of respiratory diseases.
    Type: Grant
    Filed: July 30, 1990
    Date of Patent: May 18, 1993
    Assignee: Boehringer Mannheim Italia
    Inventors: Silvano Spinelli, Roberto Di Domenico, Ernesto Menta, Bruno Lumachi, Licia Gallico, Sergio Tognella
  • Patent number: 5204018
    Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 -- and R.sup.2 denotes a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --; ring A.sup.1 signifies unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; A.sup.3, A.sup.4 and ring A.sup.2 each independently represent unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen or trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1, Z.sup.2 and Z.sup.3 each independently signify a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.tbd.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or the trans form of --CH.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: April 20, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Stephen Kelly
  • Patent number: 5177089
    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 hydroben 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: July 25, 1990
    Date of Patent: January 5, 1993
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5175167
    Abstract: Hetarylalkenes of the general formula I ##STR1## where Ar is hetaryl,A is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl or unsubstituted or monosubstituted, disubstituted or trisubstituted aryl or aralkyl, ##STR2## Z is whereR is hydrogen, C.sub.2 -C.sub.4 -acyl, unsubstituted or substituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted phenylsulfonyl or a radical R.sup.1,R.sup.1 is C.sub.1 -C.sub.4 -alkyl or unsubstituted or substituted phenyl or benzyland Hal is fluorine, chlorine, bromine or iodine,and B is unsubstituted or substituted mononuclear or dinuclear aryl, aralkyl or hetaryl,and their N-oxides and addition salts, the preparation of these substances, intermediates for this purpose and the preparation thereof, fungicides containing hetarylalkenes and a corresponding method for controlling harmful fungi.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: December 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Zipperer, Manfred Lauer, Norbert Goetz, Thomas Zierke, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5164114
    Abstract: Ethyne derivatives of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.3 --C.tbd.C--A.sup.4 --(Z.sup.2 --A.sup.2).sub.n --R.sup.2 Iwherein R.sup.1, A.sup.1, Z.sup.1, m, A.sup.3, A.sup.4, .sub.2 Z.sup.2 and n have the meaning given in Claim 1 and R.sup.2 is --OCF.sub.3, --OC.sub.2 F.sub.4 H or --OC.sub.2 F.sub.5, are suitable as components of liquid crystal phases.
    Type: Grant
    Filed: November 25, 1988
    Date of Patent: November 17, 1992
    Assignee: Merck Patent Gesellschaft Mit Beschraenkter Haftung
    Inventors: Hans A. Kurmeier, Volker Reiffenrath, Eike Poetsch, Joachim Krause, Georg Weber
  • Patent number: 5162329
    Abstract: .beta.-picoline derivatives of the formula ##STR1## where A is CR.sup.1 R.sup.2, R.sup.1 and R.sup.2 independently of each other are hydrogen, alkyl, alkenyl or alkynyl, or R.sup.1 and R.sup.2 together form a methylene chain,B is one of the groups CH.sub.2, CHOR.sup.3, CHalR.sup.4, C.dbd.O or C.dbd.N-O-R.sup.5, R.sup.3 being hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, acyl, phenyl, benzyl or benzoyl, where the phenyl ring is substituted or unsubstituted, R.sup.4 being hydrogen, fluorine, chlorine, bromine or iodine, R.sup.5 being hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, phenyl or benzyl, the phenyl ring being substituted or unsubstituted,Ar is a substituted or unsubstituted aryl radical,their N-oxides and plant-tolerated acid addition salts, and fungicides containing these compounds.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: November 10, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Wagner, Bernhard Zipperer, Norbert Goetz, Michael Keil, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5151428
    Abstract: A pyridine derivative of the formula: ##STR1## wherein R.sup.1 is, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy gorup, a C.sub.1 -C.sub.3 haloalkoxy group, a cyano group or a nitro group; R.sup.2 is, the same or different, each a hydrogen atom, a halogen atom or a methyl group; R.sup.3 is a halogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sub.4 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sup.5 is, the same or different, each a halogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy group or a C.sub.1 -C.sub.3 haloalkoxy group; X is an oxygen atom, a sulfur atom, a carbonyl group, a sulfinyl group, a sulfonyl group, an imino group or a methylene group; Y is an oxygen atom or a sulfur atom; l is an integer of 1 to 5; m is an integer of 1 to 3; and n is an integer of 1 to 4, which is useful for control of insect pest.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: September 29, 1992
    Inventors: Noriyasu Sakamoto, Hirosi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda, Noritada Matsuo
  • Patent number: 5151436
    Abstract: Therapeutically useful thioformamide derivatives of the formula: ##STR1## wherein R represents alkyl, Het represents pyrid-3-yl, isoquinolin-4-yl, tetrahydroquinolin-3-yl, quinolin-3-yl, pyridazin-4-yl, pyrimid-5-yl, thiazol-5-yl, thieno[2,3-b]-pyridin-5-yl, pyrazin-2-yl, indol-3-yl and thieno[3,2-b]-pyridin-6-yl, Y represents ethylene, methylene or a valency bond, and X represents carbonyl, hydroxymethylene, >C.dbd.NOR.sup.1, >C.dbd.NN(R.sup.1).sub.2 or >C.dbd.NN(R.sup.1)CON(R.sup.1).sub.2 in which R.sup.1 represents hydrogen or optionally substituted alkyl, benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl or pyrid-3-ylmethyl, or two R.sup.1 substituents on the same nitrogen atom may together form an optionally substituted alkylene radical chain and salts thereof, processes for their preparation and compositions containing them are described.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: September 29, 1992
    Assignee: Rhone-Poulenc Sante
    Inventors: David C. Cook, Terance W. Hart, Iain M. Mc Lay, Malcolm N. Palfreyman, Brian W. Sharp, Roger J. A. Walsh
  • Patent number: 5149705
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: September 22, 1992
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5137923
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 --OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which: 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: August 11, 1992
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 5134167
    Abstract: 1-Azabutadienes of the formula ##STR1## where R.sup.1 and R.sup.2 are each phenyl, biphenyl, naphthyl or pyridyl, and these radicals may be substituted, or are each alkyl which is unsubstituted or substituted, R.sup.3 is substituted or unsubstituted phenyl or a radical OR.sup.4, where R.sup.4 is hydrogen, alkyl or an aromatic or aliphatic acyl group, or R.sup.3 is a radical NHR.sup.5, where R.sup.5 is hydrogen, substituted or unsubstituted phenyl, or the carbamide group, and fungicidal agents containing these compounds.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: July 28, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Lauer, Bernhard Zipperer, Norbert Goetz, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5089168
    Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.
    Type: Grant
    Filed: May 16, 1989
    Date of Patent: February 18, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Reinhard Hopf, Volker Reiffenrath, Eike Poetsch, Bernhard Scheuble, Thomas Geelhaar
  • Patent number: 5084575
    Abstract: There are disclosed compounds of the formula ##STR1## wherein a is alkyl 3-19 carbon atoms, diloweralkyl allyl, diahaloallyl, diphenylallyl, lower alkynyl, ##STR2## W is --CR.sub.2 O--, --CH.dbd.CH-- or --CH.dbd.CHCH.sub.2 O-- X is N or CR;Z is ##STR3## R is hydrogen or lower alkyl; Y is ##STR4## R.sup.1 is hydrogen, lower alkyl or phenyl; R.sup.2 is hydrogen or lower alkyl; orR.sup.1 and R.sup.2 taken together form a benzene ring, optionally substituted by halo;R.sup.3 is --OR, ##STR5## -- NHSO.sub.2 R.sup.4 ; R.sup.4 is phenyl or loweralkyl substituted phenyl;R.sup.5 is halo;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as alelrgic rhinitis, allergic bronchial asthma and the like, in psoriasis, ulcerative colitis, rheumatoid arthritis as well as in other immediate hypersensitivity reactions.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: January 28, 1992
    Assignee: American Home Products Corporation
    Inventors: Anthony F. Kreft, III., John H. Musser, James J. Bicksler, John W. Giberson, Dennis M. Kubrak, Annette L. Banker
  • Patent number: 5081250
    Abstract: A regiospecific, catalyzed process for preparing acyl derivatives of aromatic nitrogen-containing heterocyclic compounds in which the keto group is selectively added ortho to the nitrogen atom on the aromatic ring. In the presence of a ruthenium carbonyl compound, carbon monoxide and an olefin, the aromatic heterocyclic compound which has an unsubstituted carbon atom ortho to at least one of the heterocyclic atoms adds the acyl group essentially completely in ortho position.
    Type: Grant
    Filed: August 15, 1989
    Date of Patent: January 14, 1992
    Assignee: Amoco Corporation
    Inventors: Eric J. Moore, Wayne R. Pretzer
  • Patent number: 5079361
    Abstract: Cross-linking reagents which are highly specific for sulphydryl groups and react with thiols at an excellent rate. The essential feature of the reagents is at least one vinyl group conjugated with an armoatic nitrogen heterocycle. Particular examples include vinyl pyridines, vinyl pyrimidines and vinyl triazines.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 7, 1992
    Assignee: Celltech Limited
    Inventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
  • Patent number: 5077409
    Abstract: Methods of preparing bis-aryl amide and urea compounds of the general formula: ##STR1## wherein x is a divalent amide or urea substituent and Y is a nitrogen containing heterocycle, which compounds are inhibitors of platelet activating factor.
    Type: Grant
    Filed: May 4, 1990
    Date of Patent: December 31, 1991
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • 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: 5013854
    Abstract: An improved process for preparing trialkylsilyl ester and acid halide derivatives of carboxylic acids is provided along with novel trialkylsilyl ester intermediates of 2-(2-furyl)-2-methoximinoacetic acid.
    Type: Grant
    Filed: February 2, 1989
    Date of Patent: May 7, 1991
    Assignee: Eli Lilly and Company
    Inventor: Charles A. Bunnell
  • 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: 5001156
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: March 19, 1991
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 4958023
    Abstract: There are provided gastric antiulcer and cytoprotective substituted N-phenyl-2-pyridinecarbothioamides. The process for their production and formulation is disclosed.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: September 18, 1990
    Assignee: American Home Products Corporation
    Inventors: William A. Kinney, Nancy E. Lee
  • Patent number: 4946852
    Abstract: 4(R)-Substituted 6(S)-phenyloxymethyl-, 6(S)-.beta.-phenylethyl- and 6(S)-.beta.-styryl-tetrahydropyran-2-ones of the general formula V ##STR1## in which R.sup.7, R.sup.8 and A have the meanings given, and the corresponding open-chain hydroxycarboxylic acids, pharmacologically acceptable salts and esters thereof, processes for the preparation of these compounds, their use as medicaments and pharmaceutical products are described. Novel .alpha.,.beta.-unsaturated lactones for the preparation of the compounds of the formula V are also described.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: August 7, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heiner Jendralla, Gerhard Beck, Gunther Wess, Bela Kerekjarto
  • Patent number: 4933475
    Abstract: Compounds having the formula ##STR1## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: June 12, 1990
    Assignee: Pfizer, Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4923884
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: May 8, 1990
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 4920232
    Abstract: Known and novel substituted acroleins of the general formula I ##STR1## where R.sup.1 is alkoxy, phenoxy, halogen, haloalkyl, haloalkoxy, haloalkylthiyl or nitro, n is an integer from 1 to 5, in the case of n being greater than 1 the R.sup.1 s being identical or different and in the event of nitro substitution the aromatic ring carrying not more than 3 nitro groups, and where R.sup.2 is alkyl, cycloalkyl, unsubstituted or substituted aryl or hetaryl or a nonaromatic heterocyclic radical, are prepared by reacting a phenylacetaldehyde of the general formula II ##STR2## with an aldehyde of the general formula III[R.sup.2 -CHO] IIIin the presence of a base and a solvent. These acroleins are useful to prepare hydroxymethyloxiranes which are intermediates in the synthesis of antimycotic and fungicidal azoylmethyloxiranes.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: April 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Stefan Karbach, Hans-Gert Recker
  • Patent number: 4898947
    Abstract: A compound of the formula: ##STR1## (wherein R.sup.1 is hydrogen or a lower alkyl) can be produced advantageously by (1) reacting a compound of the formula: ##STR2## (wherein R.sup.1 has the meaning given above) with a halogenating agent or sulfonyl halide to give a compound of the formula: ##STR3## (wherein R.sup.1 has the meaning given above and X is a halogen or an alkyl- or aryl-sulfonyloxy), (2) reacting the resulting compound with a compound of the formula: ##STR4## to give a compound of the formula: ##STR5## (wherein R.sup.1 has the meaning given above), (3) reacting the resulting compound with a compound of the formula: ##STR6## to give a compound of the formula: ##STR7## (wherein R.sup.1 has the meaning given above), and (4) subjecting the resulting compound to catalytic reduction.
    Type: Grant
    Filed: December 29, 1988
    Date of Patent: February 6, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kanji Meguro, Takeshi Fujita, Chitoshi Hatanaka, Satoru Ooi
  • Patent number: 4889865
    Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 26, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • 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: 4876349
    Abstract: The compounds of the formula ##STR1## wherein X and Y are independently --CH.sub.2 -- or >C(CH.sub.3).sub.2 ; Z is --CHR.sup.8 --, >Co, >CR.sup.8 OR.sup.7 , --CHR.sup.8 --CHR.sup.8 --, --CHOR.sup.7 --CH.sub.2 --, --CO--CHOR.sup.7 or --CHOR.sup.7 --CHOR.sup.7 --R.sup.1 is a 5- or 6-membered, monocyclic heterocyclic group which optionally can be C-substituted by halogen, lower-alkyl, lower-alkoxy, acyloxy, nitro, hydroxy, amino, lower-alkylamino or di-lower-alkylamino and/or which can be substituted on a ring --NH-- group by lower-alkyl; R.sup.2 and R.sup.3 are independently hydrogen, lower-alkyl, trifluoromethyl or halogen and one of R.sup.2 and R.sup.3 always is trifluoromethyl or lower-alkyl; R.sup.4 and R.sup.5 are independently hydrogen, alkyl, alkoxy or halogen; R.sup.6 is hydrogen, lower-alkyl or --OR.sup.7 ; R.sup.7 is hydrogen, lower-alkyl or acyl; R.sup.8 is hydrogen or lower-alkyl; and R.sup.7 and R.sup.8 can be the same or different from one another.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: October 24, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Ekkehard Weiss
  • Patent number: 4845228
    Abstract: The present invention relates to cyclohexanone derivatives represented by general formula: ##STR1## wherein R represents a hydrogen atom or an acetyl group. The cyclohexanone derivatives are important intermediates for producing isoquinoline derivatives which are useful as drugs, especially for heart drugs.
    Type: Grant
    Filed: January 26, 1988
    Date of Patent: July 4, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tsuneji Suzuki, Sannohe, Kunio, Toshihiko Ito, Masahiko Maruyama, Joji Kamiya, Makoto Hirayama, Takafumi Kitano, Akira Awaya
  • Patent number: 4845219
    Abstract: A compound of the general formula [I]: ##STR1## wherein R.sub.1 represents a higher alkyl group or an N-(higher alkyl)carbamoyl group, R.sub.2 represents a lower alkyl group, an acyl group having at least three carbon atoms, an N-(lower alkyl)carbamoyl group, an N-(lower alkyl)thiocarbamoyl group or a benzyl group, R represents a primary, secondary or tertiary amino group or a quaternary ammonium group, x is 1 or 2, y is a number of 0, 1 or 2, and z is an integer of 2-10, or a pharmaceutically acceptable salt thereof. The novel substances have both anti-tumor activity and platelet activating factor-inhibiting property, and they are effective as an anti-tumor agent without circulatory trouble.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: July 4, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Aono
  • Patent number: 4834904
    Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: May 30, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
  • Patent number: 4826531
    Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: May 2, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 4824612
    Abstract: Aromatic ketones or .alpha.-diketones can be prepared from the corresponding carbinols by reaction with molar amounts of a sulfonyl chloride in the presence of a base. The corresponding sulfinic acid or salt thereof with the base is formed simultaneously.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: April 25, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Rutsch, Mario Slongo
  • Patent number: 4814458
    Abstract: This invention relates to a novel process for preparing 4-acetyl-1-methyl-7-pyridyl-5,6,7,8-tetrahydro-3(2H)-isoquinolinone characterized by condensing 2-acetyl-4-pyridyl cyclohexanone with acetoacetamide. This compound is useful as pharmaceuticals, particularly cardiotonics.
    Type: Grant
    Filed: February 2, 1987
    Date of Patent: March 21, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Nobuyuki Fukazawa, Tatsuo Kaiho, Hiroyuki Yamashita
  • Patent number: 4797411
    Abstract: The invention relates to cycloalkyl-substituted 4-pyridyl derivatives of formula (I) ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl;each of R.sub.1 and R.sub.2 is, independently, hydrogen or C.sub.1 -C.sub.4 alkyl;n is an integer of 1 to 5; and either(a) A is >C.dbd.O and B is --O--, --NH-- or --CH.sub.2 --; or(b) A is --CH.sub.2 --and B is --O--, --NH--, --CH.sub.2 -- or >C.dbd.O; or(c) A is --O-- and B is >C.dbd.O or --CH.sub.2 --; or(d) A is --NH-- and B is >C.dbd.O or --CH.sub.2 --,and their pharmaceutically acceptable salts.The compounds of the invention show aromatase inhibiting activity and can be useful, e.g., in treating hormone-dependent tumors and prostatic hyperplasia.
    Type: Grant
    Filed: July 13, 1987
    Date of Patent: January 10, 1989
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Angelo Crugnola, Enrico di Salle, Paolo Lombardi
  • Patent number: 4786733
    Abstract: Substituted pyridine compounds particularly alkyl-substituted pyridines, are directly fluorinated to the corresponding 2-fluoro alkyl-substituted pyridines. Fluorine gas, preferably diluted with an inert gas, is passed into the substituted pyridine, preferably in a solvent, at a temperature of +25.degree. C. to -40.degree. C., preferably about -25.degree. C.
    Type: Grant
    Filed: July 9, 1987
    Date of Patent: November 22, 1988
    Assignee: Allied-Signal Inc.
    Inventors: Michael Van Der Puy, Richard E. Eibeck
  • Patent number: 4772714
    Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: September 20, 1988
    Assignee: Agency of Industrial Science & Technology
    Inventors: Masato Tanaka, Toshiyasu Sakakura
  • Patent number: 4753911
    Abstract: Insoluble complex oxidation catalysts comprising chromium salts bound on an insoluble polymer supports having pendant pyridine groups, that are useful in oxidation reactions such as Tetralino.RTM. to .alpha.-tetralone, ethylbenzene to acetophenone, and 2-methyl-5-ethylpyridine to 2-methyl-5-acetylpyridine. Also disclosed are processes for accomplishing such oxidations utilizing such catalysts.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: June 28, 1988
    Assignee: Reilly Tar and Chemical Corp.
    Inventors: Gerald L. Goe, Thomas D. Bailey, James R. Beadle
  • Patent number: 4752413
    Abstract: A novel liquid crystal compound exhibiting smectic phases and useful for display elements and a chiral smectic liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 and R.sup.2 each represent an alkyl group of 1 to 20 carbon atoms and X represents H atom or F atom, and which composition comprises at least one kind of the compounds of the formula (I) and an optically active compound.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: June 21, 1988
    Assignee: Chisso Corporation
    Inventors: Hiromichi Inoue, Takashi Inukai, Kouji Ohno, Shinichi Saito, Kazutoshi Miyazawa
  • Patent number: 4745120
    Abstract: The present invention relates to new pyridines substituted in the 3-position, of the formula ##STR1## and to a process for their preparation. The compounds bring about specific inhibition of thromboxane synthetase and can thus be used as medicaments.
    Type: Grant
    Filed: August 21, 1985
    Date of Patent: May 17, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Wess, Wilhelm Bartmann, Gerhard Beck, Hans-Hermann Lau
  • Patent number: 4739079
    Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: April 19, 1988
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4733011
    Abstract: Compounds of the formula ##STR1## wherein A is C--C single bond, --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 --CH.sub.2 --, CH(CH.sub.3)CH.sub.2 --, --C(CH.sub.3).sub.2 CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 O--; R.sup.1a and R.sup.1 each independently is hydrogen or a protective group which can be cleaved by solvolysis or by hydrogenolysis; R.sup.2 is H or alkyl of 1 to 3 C atoms; R.sup.3 is alkyl of 3 to 5 C atoms, phenyl or phenyl which is monosubstituted to trisubstituted by F, Cl, OH, OCH.sub.3, OC.sub.2 H.sub.5, CF.sub.3 or alkyl of 1 to 3 C atoms, or, when A is not --CH.sub.2 O--, can also be pyridyl, thienyl, naphthyl or alkoxy of 1 to 4 C atoms; indicates a bond in the .beta.-position and wavy line ( ) means that the bond can be in the .alpha.- or .beta.-position, are valuable intermediates for the stereospecific preparation of 13-thiaprostaglandin derivatives. The latter are prepared by U.V.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: March 22, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Bernhard Riefling, Hans-Eckart Radunz
  • Patent number: 4709097
    Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: November 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
  • Patent number: 4692450
    Abstract: Polycyclic salts of the formulaA.sup.- XN.sup.+ CH.sub.2 --(Y).sub.n --(CH.sub.2).sub.p --(Z).sub.q --L--(T).sub.r --M IwhereinA.sup.- is the anion of a strong organic or inorganic acid;XN.sup.+ is pyridinium, pyrimidinium, thiazolium or imidazolium substituted by R.sup.1, R.sup.2 and R.sup.3 ;n, q and r individually are the integer 1 or 0 and p is an integer from 1 to 15;Y is CH.sub.2, C(H,OH) or C(O);Z is O, S, CH.sub.2, C(O), NQ.sup.1, SO.sub.2, C(O)O, OC(O), C(O)N(Q.sup.1) or N(Q.sup.1)C(O);L is p-phenylene substituted by R.sup.4 ; andM is phenyl substituted by R.sup.5 and R.sup.6,T has one of the meanings given above, for Z or is C(CH.sub.3).sub.2, C.sub.2 H.sub.4, C(Q.sup.2).dbd.C(Q.sup.3), C.tbd.C, CH.sub.2 C(O), C(O)CH.sub.2, CH.sub.2 O or OCH.sub.2,R.sup.1 is a group Ar, Ar--C.sub.1-4 -alkyl, ArO or Arc(O),Ar is phenyl substituted by R.sup.7, R.sup.8 and R.sup.9 ;R.sup.2 and R.sup.3 individually are H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.6 H.sub.
    Type: Grant
    Filed: January 10, 1986
    Date of Patent: September 8, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Jean-Marie Cassal, Albrecht Edenhofer, Henri Ramuz
  • Patent number: 4686291
    Abstract: A process for the preparation of a methyl ketone of the formula ##STR1## in which R.sup.1 is alkyl, alkenyl, alkinyl, optionally substituted aryl or optionally substituted heteroaryl,R.sup.2 is alkyl,R.sup.3 is alkyl orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, from a cycloalkyl ring,comprising reacting a methyl sec.-alkyl ketone of the formula ##STR2## with a halide of the formulaR.sup.1 --CH.sub.2 --Xin whichX is halogen,in the presence of a base, a diluent, and a phase-transfer catalyst.
    Type: Grant
    Filed: November 26, 1985
    Date of Patent: August 11, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hans-Ludwig Elbe