Carbonyl Of -coo- Group Bonded Directly To A Ring Patents (Class 544/172)
  • Patent number: 5731436
    Abstract: Processes for producing benzothiophenes employing ethylene carbonate or propylene carbonate are provided.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: March 24, 1998
    Assignee: Eli Lilly and Company
    Inventor: Douglas P. Kjell
  • Patent number: 5686586
    Abstract: A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis.In the formula, X represents --CH.dbd.CH--, O or S,R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl, R.sub.2 represents hydroxy, hydrogen, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 chain ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,R.sub.3 represents --CH.sub.2 OH or --COR.sub.4, or --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 chain ring,R.sub.4 represents --OR.sub.5 or ##STR2## R.sub.
    Type: Grant
    Filed: October 4, 1996
    Date of Patent: November 11, 1997
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5686623
    Abstract: A method for preparing taxane derivatives of general formula (I) by esterifying protected baccatin III or protected 10-deacetyl baccatin III with an acid of general formula (II). In general formulae (I) and (II), Ar is an aryl radical; R.sub.1 and R.sub.2 which are the same or different, are a hydrogen atom, an alkyl, phenylalkyl, phenyl, alkoxyphenyl or dialkoxyphenyl radical, or R.sub.1 or R.sub.2, together with the carbon atom to which they are attached, form a 4-7 membered ring; R.sub.3 is an acetyl radical or a hydroxy function protective grouping, and R.sub.4 is a hydroxy function protective grouping; R is a phenyl radical or a radical of formula R.sub.5 --O-- wherein R.sub.5 -- is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl or saturated or unsaturated nitrogenous heterocylcyl radical. The products of general formula (I) are particularly useful for preparing taxol, Taxotere and analogues thereof having remarkable antitumor properties.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: November 11, 1997
    Assignee: Rhone-Poulenc Rorer, S.A.
    Inventors: Jean-Noel Denis, Andrew-Elliot Greene, Alice Kanazawa
  • Patent number: 5637583
    Abstract: Aminocyclohexylester compounds, including thioesters, are disclosed. The compounds of the present invention may be incorporated in compositions and kits. The present invention also discloses a variety of in vitro and in vivo uses for the compounds and compositions, including the blockade of ion channels and the treatment of arrhythmias.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: June 10, 1997
    Assignee: University of British Columbia
    Inventors: Bernard A. MacLeod, Michael J. A. Walker, Richard A. Wall
  • Patent number: 5631369
    Abstract: Novel processes for producing compounds of formula I ##STR1## wherein R.sup.1 and R.sup.2 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form piperidinyl, pyrrolidinyl, methylpyrrolidinyl, dimethylpyrrolidinyl, morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; andn is 2 or 3;or a pharmaceutically acceptable salt thereof employing alkylacetate solvents are provided.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: May 20, 1997
    Assignee: Eli Lilly and Company
    Inventors: Douglas P. Kjell, Fred M. Perry
  • Patent number: 5552543
    Abstract: Novel six-membered hetero "N" compounds having antibiotic activity, represented by the formula: ##STR1## where X.dbd.S, O, CH.sub.2, or SeY.dbd.OH, NH.sub.2, NHCOR.sub.9, or SHR.sub.1,R.sub.2,R.sub.3,R.sub.4,R.sub.5,R.sub.6,R.sub.7 (which may be identical or different).dbd.H, alkyl, or arylR.sub.9 .dbd.a .beta.-lactam active side chain;computer models for evaluating such compounds and processes for preparing them.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: September 3, 1996
    Assignee: Simon Fraser University
    Inventors: Saul Wolfe, Stephen Bruder
  • Patent number: 5512565
    Abstract: The compounds of the formula: ##STR1## in which ##STR2## where R.sup.7 is hydrogen, alkyl, hydroxy, alkanoyloxy, hydroxyalkyl, hydroxycarbonyl, alkoxycarbonyl, phenyl or substituted phenyl, in which the substituent is alkyl, alkoxy, halo, nitro, cyano, haloalkyl, perhaloalkyl or dialkylaminoalkyl; R.sup.8 is hydrogen or alkyl or R.sup.7 and R.sup.8 taken together are polymethylene; R.sup.9 is hydrogen, alkyl, phenyl or substituted phenyl, in which the substituent is alkyl, alkoxy, halo, nitro, cyano or perhaloalkyl; R.sup.10 is hydrogen, alkyl or gemdialkyl; n is one of the integers 0, 1 or 2; and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are, independently, hydrogen, alkyl, alkoxy, halo, nitro, cyano or perhaloalkyl, alkoxycarbonyl or hydroxycarbonyl; and when X is --NR.sup.9 -- or R.sup.7 is an amino alkyl group, a pharmaceutically acceptable salt thereof; are useful as inhibitors of cholesterol ester hydrolase.
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: April 30, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard E. Mewshaw, Thomas J. Commons, Donald P. Strike
  • Patent number: 5506227
    Abstract: Compounds having the formula I: ##STR1## are antagonists of the actions of leukotrienes. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: April 9, 1996
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert Zamboni, Daniel Guay, Jacques-Yves Gauthier
  • Patent number: 5373009
    Abstract: A compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independently, halo, trifluoromethyl, cyano, nitro, alkyl, alkoxy, --CO.sub.2 H, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, mono- or di-alkylaminocarbonyl, or mono- or di-alkylaminocarbonyloxy;m is 0, 1 or 2 andR.sup.3 is alkyl;n and p are, independently, 0, 1 or 2;X is O, S or CR.sup.4 R.sup.5,where R.sup.4 and R.sup.5 are, independently, H or alkyl or R.sup.4 and R.sup.5 together with the interposed carbon atom form a 3 to 8 membered carbocyclic ring, are anti-cholesterolemic agents.
    Type: Grant
    Filed: February 2, 1994
    Date of Patent: December 13, 1994
    Assignee: American Home Products Corporation
    Inventors: Thomas J. Commons, Donald P. Strike
  • Patent number: 5336684
    Abstract: Antineoplastic taxol derivatives are derived by selective oxidation of the alkene portion of the side chain of cephalomannine. The derivative displays high activity in promoting assembly of microtubulin and also displays cytotoxic activity against malignant cells.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: August 9, 1994
    Assignee: Hauser Chemical Research, Inc.
    Inventors: Christopher K. Murray, Jeffrey T. Beckvermit, Timothy D. Ziebarth
  • Patent number: 5321139
    Abstract: Two processes are described for the preparation of the optically pure compounds of formula 1: ##STR1## in which R.sup.1 and R.sup.2 are e.g. alkyl, R.sup.3 and R.sup.4 are e.g. hydrogen and R.sup.5 is e.g. hydrogen. Both processes include, as key steps, the enantioselective hydrogenation of a C.dbd.C double bond and the regioselective formation of a dicarboxylic acid monoamide derivative. In one process a phenylitaconic acid derivative is asymmetrically hydrogenated to give an optically active (R)-benzylsuccinic acid which is then converted to a diester, said diester being converted to the monoamide compound of formula 1. In the second process, a phenylitaconic acid derivative is converted to its anhydride, and the anhydride is then converted to a monoamide which is then asymmetrically hydrogenated to give the compound of formula 1.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: June 14, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ulrich Lerch, Heiner Jendralla, Bernhard Seuring, Rainer Henning
  • Patent number: 5298649
    Abstract: A naphthalene derivative having the formula is new and useful for medicine. ##STR1## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group or an acyl group;R.sup.2 independently represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a cycloalkyl group, a cycloalkylalkyl group, a hydroxyl group, an aryl group which may be substituted, an arylalkyl group whose aryl group may be substituted, a heteroaryl group, or a heteroarylalkyl group;R.sup.3 and R.sup.4 are the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkenyl group, an aryl group which may have a substituent, an arylalkyl group whose aryl group may be substituted, an arylalkenyl group whose aryl group may be substituted, a cycloalkyl group, an alkoxyalkyl group, a heteroaryl group, a heteroarylalkyl group, a carboxyl group, a carboxyalkyl group, an aminoalkyl group, or a cyano group;R.sup.5 represents a group of the formula, --OR.sup.7, (wherein R.sup.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: March 29, 1994
    Assignee: Eisai Co., Ltd.
    Inventors: Makoto Okita, Hiroshi Shirota, Masayuki Tanaka, Toshihiko Kaneko, Katsuya Tagami, Shigeki Hibi, Yasushi Okamoto, Seiichiro Nomoto, Takeshi Suzuki, Kenichi Chiba, Masaki Goto, Ryoichi Hashida, Hideki Ono, Hideto Ohhara, Hideki Sakurai, Shigeru Souda, Yoshimasa Machida, Kouichi Katayama, Isao Yamatsu
  • Patent number: 5281720
    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 angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: January 25, 1994
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Yves Girard, John W. Gillard, Laird A. Trimble, John Scheigetz, James A. Yergey, Yves Ducharme, Deborah A. Nicoll-Griffith, John H. Hutchinson
  • Patent number: 5190940
    Abstract: The compounds of the formula: ##STR1## in which R.sup.1 is hydrogen or alkyl; R.sup.2 is alkyl, cycloalkyl, cycloalkylalkyl, phenylalkyl or alkylphenylalkyl; or R.sup.1 and R.sup.2 taken together complete a heterocyclic moiety of the formula: ##STR2## in which X is ##STR3## where R.sup.3,R.sup.4 and R.sup.5 are, independently hydrogen, alkyl, phenyl or substituted phenyl, in which the substituents are halogeno, alkoxy or trifluoromethyl; R.sup.6 is hydrogen, alkyl or gemdialkyl and n is one of the integers 0, 1 or 2, are cholesterol ester hydrolase inhibitors useful in the treatment of high serum cholesterol levels and associated disease states in the mammal such as coronary heart disease, atherosclerosis, familial hypercholesterolemia, hyperlipemia, and the like.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: March 2, 1993
    Assignee: American Home Products Corporation
    Inventors: Thomas J. Commons, Richard E. Mewshaw, Donald P. Strike
  • Patent number: 5183889
    Abstract: A benzonphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjuctive tissues.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: February 2, 1993
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5173487
    Abstract: Antihypercholesterolemic activity, due to competitive inhibition of HMG CoA reductase, is exhibited by a compound of the formula ##STR1## m is 0 to 3; R is selected from:(1) alkyl;(2) substituted alkyl;(3) alkoxy;(4) alkenyl;(5) cycloalkyl;(6) phenyl; and(7) substituted aryl; andR.sup.1 and R.sup.2 are as defined in the specification.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: December 22, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jeffrey O. Saunders, Eric M. Gordon
  • Patent number: 5162571
    Abstract: Novel phenol derivatives of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, Y and n are as defined in the specification, which have therapeutic and prophylactic activities against cerebral, cardiac, renal and pulmonary circulatory system diseases, respiratory diseases, allergy, anaphylactic shock, endotoxin shock, inflammation and the like as well as inhibiting activities against vascularization by oncocytes.
    Type: Grant
    Filed: June 8, 1988
    Date of Patent: November 10, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsuru Shiraishi, Kohei Mishikawa
  • Patent number: 5145958
    Abstract: 2,4- or 2,6-dihalogeno-aniline can be prepared by reacting an amino-benzoic acid ester of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 have the meanings indicated in the description, with 2-2.5 moles of a chlorinating or brominating agent in an inert reaction medium at a temperature of 40.degree.-160.degree. C. and subsequently hydrolyzing and decarboxylating the dihalogenated amino-benzoic acid ester.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Kissener, Helmut Fiege
  • Patent number: 5142048
    Abstract: The invention relates to novel intermediate compounds for preparation of novel amino acid derivatives having renin inhibiting activity.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: August 25, 1992
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Keiji Hemmi, Masahiro Neya, Hiroshi Marusawa, Keisuke Imai, Natsuko Kayakiri, Masashi Hashimoto
  • Patent number: 5116979
    Abstract: Dihydrocaffeic acid derivatives are here disclosed which are applicable as medicines having excellent absorbency in the case of oral administration and good concentration retention in blood.The disclosed compounds have the function to induce the production and secretion of a nerve growth factor (NGF) in the brain tissue, and therefore they are effective as medicines for the progression inhibition and therapy of regressive disorders of the central nervous system.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: May 26, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobuyuki Fukazawa, Hajime Iizuka, Osamu Yano, Yukio Miyama
  • Patent number: 5114960
    Abstract: Compounds of the formula ##STR1## wherein A taken together with the two carbon atoms denoted as .alpha. and .beta. is a group of the formula ##STR2## and the dotted line is the double bond present in formulas (i) and (iii); and wherein n is zero, 1, 2 or 3, one of R.sup.1 and R.sup.2 is carboxy or alkoxycarbonyl and the other is hydrogen, R.sup.3 is hydrogen, alkyl, alkoxy, aryloxy, azido, cyano or alkylthio, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each, independently, is hydrogen or alkyl or, when R.sup.1 is carboxy or alkoxycarbonyl and n stands for 1, R.sup.4 and R.sup.6 taken together can be a carbon-carbon bond or, when R.sup.2 is carboxy or alkoxycarbonyl, R.sup.5 and R.sup.7 taken together can be a carbon-carbon bond, R.sup.8 is halogen, alkyl, haloalkyl or alkoxy and R.sup.9 is hydrogen, halogen, alkyl or alkoxy, and pharmaceutically acceptable salts of the compounds of formula I in which one of R.sup.1 and R.sup.
    Type: Grant
    Filed: June 26, 1990
    Date of Patent: May 19, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Geoffrey Lawton, John M. Osbond, Christopher R. Self
  • Patent number: 5055577
    Abstract: The present invention provides a process for preparing urethanes from primary or secondary amines, carbon dioxide and a diolefin. The amine is reacted with carbon dioxide to form the ammonium carbamate salt which is then reacted with a stoichiometric amount of a diolefin coordinated to palladium(II).
    Type: Grant
    Filed: June 18, 1990
    Date of Patent: October 8, 1991
    Assignee: Monsanto Company
    Inventors: Dennis P. Riley, William D. McGhee
  • Patent number: 4997848
    Abstract: Compounds of formula (I): ##STR1## in which: R represents hydrogen, methyl of hydroxy; X represents an alkyl, alkenyl, cycloalkyl, aryl, aralkyl, or heterocyclic group; A represents a single bond, or an alkylene, alkenylene, alkynylene or alkadienylene group; Y represents hydrogen, or an aryl, cycloalkyl or heterocyclic group] have valuable antihypercholesteremic activities and may be used in the treatment of disorders arising from a blood cholesterol imbalance in humans and other animals.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: March 5, 1991
    Assignee: Sankyo Company, Limited
    Inventors: Masaaki Kurabayashi, Hiroshi Kogen, Hiroshi Kadokawa, Hideshi Kurihara, Kazuo Hasegawa, Masao Kuroda
  • Patent number: 4968706
    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=1 or 2, 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: August 11, 1988
    Date of Patent: November 6, 1990
    Assignee: Boehringer Mannhein Italia, S.p.A.
    Inventors: Silvano Spinelli, Roberto Di Domenico, Ernesto Menta, Bruno Lumachi, Licia Gallico, Sergio Tognella
  • Patent number: 4940727
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as anti-hypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1##
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: July 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Edward S. Inamine, Otto D. Hensens, David R. Houck, Ta J. Lee, Robert L. Smith, Wasyl Halczenko, George D. Hartman, Gerald E. Stokker
  • Patent number: 4910200
    Abstract: Compounds of the formula ##STR1## wherein A is ##STR2## B is ##STR3## R.sup.1 is hydrogen; halogen, cyano or optionally substituted C.sub.1-4 alkyl; andQ is NR.sup.8 R.sup.9 or ##STR4## where R.sup.2 to R.sup.11 are substituents of various types. The compounds are useful as fungicides.
    Type: Grant
    Filed: October 9, 1986
    Date of Patent: March 20, 1990
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Jurgen Curtze, Helmut Pieper, Josef Nickl, Heinz-Manfred Becher, Guido Albert, Christo Drandarevski, Sigmund Lust, Ludwig Schroder
  • Patent number: 4904661
    Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: February 27, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
  • Patent number: 4857547
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1##
    Type: Grant
    Filed: January 7, 1988
    Date of Patent: August 15, 1989
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Ta J. Lee
  • Patent number: 4803268
    Abstract: The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C.
    Type: Grant
    Filed: January 29, 1987
    Date of Patent: February 7, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Urs Muller
  • Patent number: 4783535
    Abstract: A process for the preparation of 1,4-oxazepinones and thiones having the formula: ##STR1## wherein A is an aromatic ring selected from benzene, naphthalene, quinoline or pyridine; n is 1 to 3; Z is an amino radical; R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl; and R.sup.4 and R.sup.5 are hydrogen and loweralkyl starting from chloroaromatic carboxylates and alkanolamines is disclosed. The oxazepinones and oxazepinethiones prepared by the process have utility as antihistaminics with low sedative potential. Novel intermediate compounds are also disclosed.
    Type: Grant
    Filed: March 18, 1986
    Date of Patent: November 8, 1988
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Young S. Lo, Albert D. Cale, Jr.
  • Patent number: 4774241
    Abstract: A derivative of benzoquinonylphenyl alkanoic acid amide having the formula: ##STR1## wherein X represents an oxygen atom, sulfur atom, or methylated nitrogen atom, Me represents methyl, and n is 2 or 3. This derivative is effective as a cerebral insufficiency improver.
    Type: Grant
    Filed: March 27, 1987
    Date of Patent: September 27, 1988
    Assignee: Suntory Limited
    Inventors: Toshio Tatsuoka, Kenji Suzuki, Kayoko Imao, Fumio Satoh, Seiji Miyano, Kunihiro Sumoto
  • Patent number: 4772695
    Abstract: A process for the preparation of vinyl carbamates of formula I ##STR1## is described which comprises heating an .alpha.-halogeno-carbamate of formula II ##STR2## in which X is a halogen atom at a temperature between 70.degree. and 250.degree. C. for a period of time between several minutes up to several hours. R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different. The process is applicable to a great variety of products in which R.sub.1, R.sub.2, R.sub.3, and R.sub.4 have different meanings. The process permits to prepare in a simple and economical fashion, vinyl carbamates, which have industrial value and novel vinyl carbamates.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: September 20, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Roy A. Olofson, Gary P. Wooden, Jonathan T. Martz
  • Patent number: 4766110
    Abstract: Novel inhibitors of angiotensin converting enzyme are disclosed which have the general formula ##STR1## wherein R.sub.1 and/or R.sub.3 form complex amides and imides thereof, R.sub.4 and R.sub.5 form with --N--C-- a 4-6 membered ring structure as described and the other R substituents are selected from a variety of disclosed groups.
    Type: Grant
    Filed: October 31, 1986
    Date of Patent: August 23, 1988
    Inventors: James W. Ryan, Alfred Chung
  • Patent number: 4760146
    Abstract: Novel compounds and processes for making and using them. The compounds include ethyl 1-[3-(1-piperidinyl)propyl]-6-phenyl-3-cyclohexene-1-carboxylate, 1-[3-(1-piperidinyl)propyl]-6-phenyl-3-cyclohexene-1-carboxyamide, and N,N-dimethyl-1-[3-(1-piperidinyl)propyl]-6-phenyl-3-cyclohexene-1-carboxam ide.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 26, 1988
    Assignee: Pennwalt Corporation
    Inventor: Bruce H. Toder
  • Patent number: 4753934
    Abstract: Compounds of the formula ##STR1## wherein A, B, R.sub.1, X and Q are substituents of various types, and acid addition salts thereof. The compounds are useful as fungicides.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: June 28, 1988
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Josef Nickl, Helmut Pieper, Jurgen Curtze, Christo Drandarevski, Sigmund Lust
  • Patent number: 4742169
    Abstract: The invention is a process for the preparation of halohydroxyalkyl carbamates which comprises contacting an epihalohydrin carbonate with a secondary amine-containing compound, wherein the secondary amine has a pKa at which the secondary amine will react with the epihalohydrin carbonate and which does not catalyze the formation of unwanted by-products in the further presence of an acid scavenger capable of forming a salt with the hydrogen halide by-product formed, in an amount sufficient to prevent the formation of unwanted by-products, in a polar organic solvent under conditions such that a halohydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared.
    Type: Grant
    Filed: April 5, 1985
    Date of Patent: May 3, 1988
    Assignee: The Dow Chemical Company
    Inventors: Marsha A. Paul, George A. Doorakian
  • Patent number: 4725680
    Abstract: The invention relates to a process for preparing carbamic acid derivatives of formula: ##STR1## in which R.sup.1 or R.sup.2 denotes a hydrogen atom or a substituted or unsubstituted, saturated or unsaturated aliphatic, cycloaliphatic or heterocyclic radical, or R.sup.1 and R.sup.2 together form a ring, and Y denotes OR, SR, ##STR2## groups, R being a substituted or unsubstituted, saturated or unsaturated aliphatic or cycloaliphatic radical, or a substituted or unsubstituted aromatic radical, R.sup.3 and R.sup.4 denote a hydrogen atom or an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical or together form a ring, and R.sup.6 and R.sup.7 denote a saturated or unsaturated, substituted or unsubstituted aliphatic or cycloaliphatic radical, a hydrogen atom, an alkylthio radical or an alkyloxy radical.According to the process, a compound of formula ##STR3## is reacted with an .alpha.-halogenated derivative of formula ##STR4## at a temperature of -5.degree. to 150.degree. C.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: February 16, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
  • Patent number: 4626597
    Abstract: 16-Fluoro-16,17-didehydro prostanoids, processes for their preparation, compositions containing them and methods of using them are disclosed. The compounds and compositions have pharmaceutical utility including, for example, luteolytic activity.
    Type: Grant
    Filed: August 22, 1984
    Date of Patent: December 2, 1986
    Assignee: Farmitalia Carlo Erba, S.p.A.
    Inventors: Franco Faustini, Roberto d'Alessio, Achille Panzeri, Enrico di Salle
  • Patent number: 4621143
    Abstract: A number of novel amides were found to be highly effective as cockroach repellents.
    Type: Grant
    Filed: June 27, 1984
    Date of Patent: November 4, 1986
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terrence P. McGovern, George S. Burden
  • Patent number: 4621149
    Abstract: A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising:(a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and(b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules,in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80.degree. C. to about 300.degree. C. under a pressure of from about 1 Kg/cm.sup.2 to about 500 Kg/cm.sup.2.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: November 4, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shinsuke Fukuoka, Masazumi Chono
  • Patent number: 4612386
    Abstract: Carboxylic acid esters are produced by the reaction of a carboxylic acid halide with a carbonate ester in the presence of an initiator. The reaction of a dicarboxylic acid dihalide and a bis(alkyl carbonate) ester produces a polymeric polyester.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: September 16, 1986
    Assignee: The Dow Chemical Company
    Inventor: James M. Renga
  • Patent number: 4596800
    Abstract: A compound of formula (I) ##STR1## or a pharmaceutically acceptable salt thereof, in which R.sup.1 is hydrogen, halogen, or trifluoromethyl;R.sup.2 is hydrogen or halogen;R.sup.3 is hydrogen or methyl;R.sup.4 is --O(CH.sub.2).sub.a CO.sub.2 H or an ester or amide derivative thereof, O(CH.sub.2).sub.b M or --CO.sub.2 H or an ester or amide derivative thereofwhereina is an integer from 1 to 6,b is an integer from 2 to 7, andM is hydroxy, C.sub.1-6 alkoxy or ##STR2## wherein R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-6 alkyl or ##STR3## together form a five or six membered ring; R.sup.5 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by carboxy or esters and amides thereof; or phenyl optionally substituted by C.sub.1-6 alkyl, halogen, alkoxy or trifluoromethyl;R.sup.8 is hydrogen or C.sub.1-6 alkyl or R.sup.8 together withR.sup.5 form a carbocyclic ring; andn is 1 or 2.Processes for preparing these compounds and their use in therapy is also described.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: June 24, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: Anthony T. Ainsworth, Richard M. Hindley
  • Patent number: 4593023
    Abstract: A compound of formula (I): ##STR1## or a pharmaceutically acceptable salt, thereof, in which R.sup.1 is hydrogen, halogen, or trifluoromethyl,R.sup.2 is hydrogen or halogen,R.sup.3 is hydrogen or methyl.R.sup.4 is --O(CH.sub.2).sub.a CO.sub.2 H, --O(CH.sub.2).sub.b M, --CO.sub.2 H or an esteror amide derivative thereof in whicha is an integer from 1 to 6,b is an integer from 2 to 7, andM is hydroxy, C.sub.1-6 alkoxy or ##STR2## in which R.sup.5 and R.sup.6 are each hydrogen or C.sub.1-6 alkyl or ##STR3## together form a five or six membered ring, and n is 1 or 2; a process for preparing such a compound and its use in medicine and agriculture.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: June 3, 1986
    Assignee: Beecham Group p.l.c.
    Inventor: Richard M. Hindley
  • Patent number: 4564685
    Abstract: This disclosure describes compounds of Formula I. ##STR1## (including their pharmaceutically acceptable salts and esters) which have potent antihistamine activity which are substantially free from sedative effects.
    Type: Grant
    Filed: March 10, 1983
    Date of Patent: January 14, 1986
    Inventors: John W. A. Findlay, Geoffrey G. Coker
  • Patent number: 4533732
    Abstract: This invention relates to derivatives of 3-propionylsalicylic acid represented by the formula (1) ##STR1## wherein R represents a hydrogen atom, a lower alkyl group or a group ##STR2## (wherein R.sup.1 and R.sup.2 represent a lower alkyl group or R.sup.1 and R.sup.2, when taken together with the nitrogen atom to which they are attached, may form a heterocyclic ring with or without an intervening hetero atom, and n is an integer of 1 to 4), and X represents a hydrogen atom or a halogen atom, R being the group ##STR3## when X is a hydrogen atom. This invention also relates to processes for preparing the same.
    Type: Grant
    Filed: September 30, 1983
    Date of Patent: August 6, 1985
    Assignees: Yamamoto Chemical Industrial Company, Limited, Osaka Municipal Government
    Inventors: Hiroshige Inoue, Kenichi Fukushima, Ikuzo Nishiguchi
  • Patent number: 4521242
    Abstract: There are provided novel substituted phenyl (thiono)carbamates capable of effectively controlling broad-leaved annual weeds and annual weeds belonging to the families Gramineae and Cyperaceae such as wild Echinochloa species, monochoria, toothcup and umbrella plant, herbicidal compositions containing these (thiono)carbamates as active ingredient and a method of controlling weeds using these (thiono)carbamates. The (thiono)carbamates are substantially nonphytotoxic to useful crop plants such as the paddy rice plant.
    Type: Grant
    Filed: August 3, 1982
    Date of Patent: June 4, 1985
    Assignee: Kuraray Co., Ltd.
    Inventors: Tetsuo Takematsu, Makoto Konnai, Takeo Hosogai, Takashi Nishida
  • Patent number: 4486588
    Abstract: Precursors to benzyl compounds, useful in the manufacture of pyrethroid insecticides, are prepared by regiospecific addition of an enamine to a heterocyclic diene accompanied by elimination of volatile by-products.
    Type: Grant
    Filed: October 19, 1982
    Date of Patent: December 4, 1984
    Assignee: FMC Corporation
    Inventors: William A. Van Saun, David M. Roush
  • Patent number: 4482549
    Abstract: Compounds are described of the formula ##STR1## in which --COR.sup.1 is a complex ester or thioester group,W is alkylene,X is cis or trans --CH.dbd.CH or --CH.sub.2 CH.sub.2 --,n is 1 or 2,Y is a saturated heterocyclic amino group having 5-8 ring members, andR.sup.2 is unsubstituted or substituted phenylalkyl, thienzlalkyl, naphthylalkyl or cinnamyl, and their salts and solvates.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and antiasthmatic agents.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: November 13, 1984
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes, John Bradshaw, Malcolm Carter, Alan Wadsworth
  • Patent number: 4478598
    Abstract: The amphoteric styrene derivatives correspond to the formula ##STR1## in which X is oxygen, sulfur, a direct bond, --SO.sub.2 N(R.sub.5 --, --CON(R.sub.5 -- or --COO--, Y.sub.1 and Y.sub.2 independently of one another are C.sub.1 -C.sub.4 -alkylene or hydroxypropylene, R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.4 -alkyl or, together with the N atom, are a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, and R.sub.1, together with R.sub.5, is also a piperazine ring, R.sub.3 and R.sub.4 are hydrogen, C.sub.1-4 -alkyl, chlorine, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl or together, in the o-position relative to one another, are a trimethylene or tetramethylene group, R.sub.5 is hydrogen, C.sub.1-4 -alkyl or cyanoethyl or, together with R.sub.1, is a piperazine ring, Q is --COO or --SO.sub.3 and n is the number 1 or 2, and can be prepared by reacting the corresponding amine compounds with a halide of the formula Hal--Y.sub.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: October 23, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans R. Meyer, Max Morf
  • Patent number: 4476311
    Abstract: Analgesic and anti-inflammatory compounds are provided. These compounds possess the following general formula: ##STR1## wherein R=--COOR.sub.5, --CH.sub.2 CO.sub.2 H, ##STR2## wherein A and B=hydrogen, lower alkyl, hydroxy alkyl, lower alkyl amine, substituted lower alkyl amine, aminoalkyl, substituted aminoalkyl;R.sub.5 =lower alkyl;R.sub.1 =aryl, substituted aryl, aralkyl, alkyl, hydrogen, substituted aralkyl and heterocycle;R.sub.2 =aryl, substituted aryl, aralkyl, alkyl, substituted aralkyl, heterocycle, substituted heterocycle, biphenyl, substituted biphenyl, naphthyl, and substituted naphthyl;R.sub.3 =aryl, substituted aryl, hydrogen, aralkyl, substituted aralkyl, alkyl, heterocycle and substituted heterocycle;R.sub.2 and R.sub.3 together form a ring;R.sub.4 =hydrogen, phenyl, substituted phenyl, heterocycle; alkyl, substituted alkyl; or, R.sub.1 and R.sub.4 may form a ring;X=>C.dbd.O, --CH.sub.2 --;Y=--S--CHR.sub.4 --, --O--OHR.sub.4 --, --CHR.sub.4 --, --CR.sub.6 R.sub.7 --CHR.sub.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: October 9, 1984
    Assignee: The Purdue Frederick Company
    Inventors: Bola V. Shetty, Arthur McFadden, Peter Hofer