Chalcogen Bonded Directly At 2-position Of The Oxazole Ring Patents (Class 548/229)
  • Patent number: 4372963
    Abstract: Bisamidines carrying one unsaturated nitrogen heterocyclo-containing substituent, representative of which i; 1-[N'-(2-(5-methyl-4-imidazolyl)methylthio)ethyl)guanidino]-8-[N'-methylgu anidino]octane, are histamine H.sub.2 -antagonists.
    Type: Grant
    Filed: March 27, 1981
    Date of Patent: February 8, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Peter D. Miles
  • Patent number: 4355033
    Abstract: 2-Imino-imidazolidine derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as hereinafter set forth, and pharmaceutically acceptable acid addition salts thereof, are described. The 2-imino-imidazolidine derivatives are useful in the treatment of hypertension.
    Type: Grant
    Filed: August 14, 1980
    Date of Patent: October 19, 1982
    Assignee: Hoffman-La Roche Inc.
    Inventor: Henri Ramuz
  • Patent number: 4351945
    Abstract: Azole and azoline disulfides useful as corrosion inhibitors and antiwear agents are prepared by the halogen-induced coupling of a thiol reactant e.g., hydrocarbyl mercaptans, with a metal azole thiolate, e.g. the potassium salt of 3,5-bis-mercapto 1,2,4-thiadiazole or 2,5-bis-mercapto 1,3,4 thiadiazole in a 2-phase reaction medium comprising a mixture of a hydrocarbon and water.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: September 28, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventors: Stanley J. Brois, Antonio Gutierrez
  • Patent number: 4340606
    Abstract: This invention relates to novel 3-(p-alkylsulfonylphenyl)oxazolidinone derivatives, pharmaceutical compositions containing them and methods of using them to alleviate bacterial infections in mammals.
    Type: Grant
    Filed: October 23, 1980
    Date of Patent: July 20, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Robert B. Fugitt, Raymond W. Luckenbaugh
  • Patent number: 4332813
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: June 1, 1982
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4329347
    Abstract: Compounds of the formula ##STR1## wherein W is vinylene, methyl-vinylene, methylene or ethylene;m is 0, 1 or 2;D is straight or branched alkylene of 2 to 6 carbon atoms, straight or branched hydroxy-alkylene of 3 to 6 carbon atoms, or xylylene;R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms;R.sub.2 is cycloalkyl of 3 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 11 carbon atoms, heteroaryl, heteroarlkyl, 1,2,4-triazolyl, triphenylmethyl, 4,5-bis-(p-chlorophenyl)-oxazol-2-yl, N-methyl-cyclohexylamino-carbonylmethyl,-amino-iminomethyl or, when m is 1 or D is hydroxyalkylene or xylylene, also alkyl of 1 to 6 carbon atoms; andR.sub.3 and R.sub.4 are each hydrogen, halogen, alkyl of 1 to 4 carbon atoms, amino, acetylamino or nitro.The compounds of the invention are useful as cardiotonics and as antithrombotics.
    Type: Grant
    Filed: July 24, 1980
    Date of Patent: May 11, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Erich Muller, Josef Nickl, Josef Roch, Berthold Narr, Walter Haarmann, Johannes M. Weisenberger
  • Patent number: 4309425
    Abstract: Sulfonamides, such as N-[N-(2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide, are useful for control of arthropod pests of plants and animals and fungus disease of plants.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: January 5, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Jiin-Duey Cheng
  • Patent number: 4304780
    Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, N-oxides, hydrates and bioprecursors thereof,in which Y represents .dbd.O, .dbd.S, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 represents hydrogen, nitro, cyano, lower alkyl, aryl, lower alkylsulphonyl or arylsulphonyl;R.sub.1 and R.sub.2, which may be the same or different, each represent hydrogen lower alkyl, cycloalkyl, lower alkenyl, aralkyl, hydroxy, lower trifluoroalkyl, lower alkyl substituted by hydroxy, lower alkoxy, amine, lower alkylamino or dialkylamino, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a 5 to 7 membered heterocyclic ring which may contain other heteroatoms or the group ##STR2## where R.sub.
    Type: Grant
    Filed: June 6, 1980
    Date of Patent: December 8, 1981
    Assignee: Glaxo Group Limited
    Inventors: Michael Martin-Smith, Barry Price, John Bradshaw, John W. Clitherow
  • Patent number: 4287348
    Abstract: Sulphoalkyl quaternary salts of the formula ##STR1## wherein X is --O--, --Se--, --S--, --NR-- or --CR(R)--, R is hydrogen or alkyl, R.sub.1 is hydrogen, methyl or ethyl, R.sub.2 and R.sub.3 are each hydrogen or substituents or together represent the atoms necessary to complete an optionally substituted benzene ring, R.sub.4 is optionally substituted alkylene of 3 or 4 carbon atoms and n is 1 or 0, except that when n is 1, R.sub.1 cannot be hydrogen, are prepared by heating at a temperature above 80.degree. C. a heterocyclic base of the formula ##STR2## wherein X, R.sub.1, R.sub.2, R.sub.3 and n have the indicated meanings with a hydroxysulphonic acid of the formula HOR.sub.4 SO.sub.3 H.
    Type: Grant
    Filed: June 5, 1978
    Date of Patent: September 1, 1981
    Assignee: Ciba-Geigy AG
    Inventors: Rainer Kitzing, Geoffrey E. Ficken, Victor W. Dolden
  • Patent number: 4286096
    Abstract: Azole and azoline disulfides useful as corrosion inhibitors and antiwear agents are prepared by the halogen-induced coupling of a thiol reactant e.g., hydrocarbyl mercaptans, with a metal azole thiolate, e.g. the potassium salt of 3,5-bis-mercapto 1,2,4-thiadiazole or 2,5-bis-mercapto 1,3,4-thiadiazole in a 2-phase reaction medium comprising a mixture of a hydrocarbon and water.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: August 25, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Stanley J. Brois, Antonio Gutierrez
  • Patent number: 4281200
    Abstract: A process for recovering amino alcohols, e.g. diisopropanolamine, from their corresponding cyclic reaction products, which products are the result of the reaction of CO.sub.2 and the amino alcohol, i.e., oxazolidinones, a situation commonly encountered in acid gas removal processes employing the amino alcohols alone or in combination with other liquids such as sulfolane (tetrahydrothiophene-1,1-dioxide) for example, by reacting the cyclic product with a small but catalytic amount (less than about 10 mol percent) of a base metal compound such as the hydroxide or a base which will convert into a hydroxide under the conditions of reaction, i.e. the acid carbonates, carbonates, metaborates, oxides or hydrides at temperatures above about 105.degree. C. to about the atmospheric boiling point of the reaction medium and, optionally, recovering the amino alcohol from the reaction mass.
    Type: Grant
    Filed: August 30, 1979
    Date of Patent: July 28, 1981
    Assignee: The Dow Chemical Company
    Inventor: Karel A. J. Snoble
  • Patent number: 4277485
    Abstract: The compounds are ethylene derivatives which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A compound of this invention is 1-nitro-2-methylamino-2-[2-((4-methyl-5-imidazolyl)methylthio)-ethylamino] ethylene.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: July 7, 1981
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon F. Ganellin, Hunter D. Prain
  • Patent number: 4275200
    Abstract: The condensation of an .alpha.-halogen carbonyl compound with carbamic acid esters in the presence of a basic condensing agent and an aprotic solvent enables the production of oxazolinone-2-compounds in a high degree of purity, and in high yields in one step by using simple and readily available starting compounds.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: June 23, 1981
    Assignee: AGFA-Gevaert, A.G.
    Inventors: Fritz Benker, Hans-Heinrich Credner, Wolfgang Lassig, Ernst Meier, Siegfried Schleger
  • Patent number: 4272455
    Abstract: A method for the formation of monoalkyleneglycols, monoalkanolamines and alkylenediamines, comprising the steps of: (a) reacting ammonia or ammonium carbonate with an alkylenecarbonate to form a carbamate, (b) heating the carbamate to form a monoalkyleneglycol, an alkyleneurea and a 2-oxazolidinone, (c) further reacting the alkyleneurea and the 2-oxazolidinone with ammonium hydroxide to form ammonia or ammonium carbonate, a monoalkanolamine, and an alkylenediamine, (d) separating the ammonia or ammonium carbonate, the monoalkyleneglycol, the alkylenediamine, and the monoalkanolamine, and (e) recycling the ammonia or ammonium carbonate to reaction step (a).
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: June 9, 1981
    Assignee: The Dow Chemical Company
    Inventors: Frank T. Cook, Daniel W. Baugh, Jr., Robert V. Chambers, Jr.
  • Patent number: 4256756
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen or substituents of various types;R.sub.4 is hydrogen; alkyl of 1 to 5 carbon atoms; or optionally substituted aralkyl of 7 to 14 carbon atoms;R.sub.5 is a heterocycle;D is alkylene of 1 to 12 carbon atoms; andA is hydrogen or acyl;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as .alpha.- and .beta.-adrenergic receptor blocking agents and antidepressants.
    Type: Grant
    Filed: January 17, 1979
    Date of Patent: March 17, 1981
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Herbert Koppe, Anton Mentrup, Ernst-Otto Renth, Kurt Schromm, Wolfgang Hoefke, Gojko Muacevic
  • Patent number: 4254266
    Abstract: Fluorinated-alkyl sulfides represented by [R.sub.f (CH.sub.2).sub.n S].sub.z Q where R.sub.f is fluoroalkyl, n is 2 or 3, z is 1 or 2, and Q is an aryl, alkylaryl, alkyl heterocyclic or heterocyclic radical, are useful as surfactants or as intermediates for the preparation of salt-type, quaternary-salt, or amphoteric surfactants.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: March 3, 1981
    Assignee: Pennwalt Corporation
    Inventors: Sameeh S. Toukan, Murray Hauptschein
  • Patent number: 4251665
    Abstract: Amino resins, e.g., urea-formaldehyde and melamine-formaldehyde thermosetting resin systems, are cured with thermally-decomposable adducts of aromatic sulfonic acids and oxa-azacyclopentanes. The resin products cured with these adducts provide surface coatings having superior water resistance properties. The cured compositions can include other conventional ingredients capable of co-reacting with the amino resins, such as polyols, polyacids, alkyd resins, polyester resins, epoxies, acrylics and the like, to provide compositions curable to products having a wide range of properties.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: February 17, 1981
    Assignee: King Industries, Inc.
    Inventor: Leonard J. Calbo
  • Patent number: 4250318
    Abstract: There are disclosed 3-substituted phenyl-5-hydroxymethyl oxazolidinones which possess anti-depressant properties. The compounds are prepared by cyclizing, with ethyl carbonate, 1-substituted phenylamino-2,3-propanediol compounds.
    Type: Grant
    Filed: August 9, 1978
    Date of Patent: February 10, 1981
    Assignee: Delalande S.A.
    Inventors: Philippe L. Dostert, Colette A. Douzon, Guy R. Bourgery, Claude G. Gouret, Gisele C. Mocquet, Jean-Alain Coston
  • Patent number: 4240963
    Abstract: A process for the preparation of an indolenine of the general formula I ##STR1## where R, R.sup.1 and R.sup.2 are aliphatic radicals and R.sup.1 and R.sup.2 may also be linked and the ring A may be additionally substituted, wherein a compound of the formula II ##STR2## is heated in the presence of a Lewis acid and of a halide. The products are valuable starting compounds for the preparation of dyes.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: December 23, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Harald Laas, Axel Nissen, Hans-Joachim Opgenorth, Horst Scheuermann, Hans-Richard Mueller, Wolfgang Schulte
  • Patent number: 4236012
    Abstract: 5-Phenethyl oxazolidone compounds having the formula: ##STR1## wherein R represents a hydrogen or halogen atom or a lower alkoxy group have muscular relaxing, analgetic and antiinflammatory activities.
    Type: Grant
    Filed: January 8, 1979
    Date of Patent: November 25, 1980
    Assignee: Nippon Chemiphar Company, Limited
    Inventors: Yasuo Fujimoto, Terumi Tamada
  • Patent number: 4230865
    Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-thioureas and ureas which are inhibitors of histamine activity.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: October 28, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin
  • Patent number: 4228291
    Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines which are inhibitors of histamine activity.
    Type: Grant
    Filed: October 4, 1978
    Date of Patent: October 14, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Genellin
  • Patent number: 4221584
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo, R.sup.2, R.sup.3 and R.sup.4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R.sup.5 and R.sup.
    Type: Grant
    Filed: February 9, 1979
    Date of Patent: September 9, 1980
    Assignee: Chevron Research Company
    Inventor: Stephen D. Ziman
  • Patent number: 4220652
    Abstract: The compounds are ethylene derivatives which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A compound of this invention is 1-nitro-2-methylamino-2-[2-((4-methyl-5-imidazolyl)methylthio)ethylamino]e thylene.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: September 2, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin, Hunter D. Prain
  • Patent number: 4209628
    Abstract: Process for preparing 2-oxazolidone and its derivatives by reacting react carbon dioxide with aziridine compound, preferably, in the presence of Lewis acid as a catalyst.
    Type: Grant
    Filed: April 26, 1978
    Date of Patent: June 24, 1980
    Assignee: Tokyo Institute of Technology
    Inventors: Sakuji Ikeda, Kazuo Soga
  • Patent number: 4198339
    Abstract: Substituted 1,3-dithietane-2-carboxylic acid derivatives useful as intermediates for the preparation of highly effective penicillin and cephalosporin derivatives and the preparation thereof.
    Type: Grant
    Filed: June 7, 1978
    Date of Patent: April 15, 1980
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Masaru Iwanami, Tetsuya Maeda, Yoshinobu Nagano, Masaharu Fujimoto, Noriaki Nagano, Atsuki Yamazaki, Kazaharu Tamazawa, Kiyoshi Murase, Tadao Shibanuma
  • Patent number: 4197305
    Abstract: The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N"-disubstituted guanidino), N-(N'-substituted thioureido), N-(nitrometylene amidino) or S-(N-substituted isothioureido)groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)ethyl)isothiour eido]propane. The compounds of this invention are inhibitors of H-2 histamine receptors.
    Type: Grant
    Filed: September 11, 1978
    Date of Patent: April 8, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4188323
    Abstract: A compound having pharmacological properties comprising the structural formula ##STR1## wherein R is selected from the isopropyl, n-octyl, n-butyl or isobutyl groups; R.sub.1 is selected from the 1-naphthyloxymethyl, (2-allylphenoxy)-methyl, 4-nitrophenyl, {2-[(tetrahydrofurfuryl)oxy-]-phenoxy}-methyl, [4-(2-methoxyethyl)phenoxy]methyl, 4-isopropylthiophenyl, 4-acetaminophenoxymethyl groups; and R.sub.2 represents a hydrogen atom or a methyl group. A method for synthetizing the compound is also disclosed comprising the cyclization of aminoalcohol or halogenurethane.
    Type: Grant
    Filed: May 11, 1978
    Date of Patent: February 12, 1980
    Assignee: A. Menarini S.A.S.
    Inventors: Vittorio Pestellini, Mario Ghelardoni, Claudio Bianchini, Piero Del Soldato, Giovanna Volterra, Alberto Meli
  • Patent number: 4186129
    Abstract: Novel 5-(substituted phenyl)-oxazolidinones and their sulfur analogs of Formula I ##STR1## wherein R.sub.1 is optionally substituted lower alkyl, cycloalkyl or cycloalkylalkyl;R.sub.2 is hydrogen, optionally substituted lower alkyl, cycloalkyl, cycloalkylalkyl, optionally substituted aryl, optionally substituted aralkyl, alkenyl or a heterocyclic group;R.sub.3 is hydrogen, optionally substituted lower alkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, or optionally substituted acyl;R.sub.4 is hydrogen or optionally substituted lower alkyl;R.sub.5 is hydrogen or optionally substituted lower alkyl or optionally substituted lower alkoxycarbonyl; andX is oxygen or sulfur, have valuable pharmacological effects.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: January 29, 1980
    Assignee: Schering Aktiengesellschaft
    Inventors: Andreas Huth, Ralph Schmiechen, Wolfgang Kehr, Gert Paschelke, Helmut Wachtel, Herbert H. Schneider, Dieter Palenschat
  • Patent number: 4170594
    Abstract: This relates to oxazolyl alkyl disulphides.
    Type: Grant
    Filed: May 15, 1978
    Date of Patent: October 9, 1979
    Assignee: Givaudan Corporation
    Inventors: Paul Dubs, Heiner Kuntzel
  • Patent number: RE30721
    Abstract: The instant invention is directed to novel color and hydrolytically stable thermoplastic polyester urethanes. The invention broadly consists of adding 2-oxazolidones to the components of the polyurethane, or to the polyurethane itself.
    Type: Grant
    Filed: June 6, 1980
    Date of Patent: August 25, 1981
    Assignee: Mobay Chemical Corporation
    Inventors: Herbert L. Heiss, Robert P. Yeater, Russell P. Carter, Jr.