Thioethers Patents (Class 568/38)
  • Patent number: 5961954
    Abstract: This invention relates to new bifunctional chelating agents with intermittent chalcogen atoms, pharmaceuticals containing these compounds, their use in radiodiagnostics and radiotherapy, and methods for the production of these compounds.The compound according to the invention has the general formula (I)M--Lwhere M represents a radionuclide and L a ligand of the general formula (II).It was found, surprisingly, that these new, bifunctional chelating agents with intermittent chalcogen atoms and their coupling products with compounds that accumulate specifically are excellently suited for producing radiopharmaceuticals for diagnostic and therapeutic purposes.
    Type: Grant
    Filed: December 9, 1996
    Date of Patent: October 5, 1999
    Assignee: Institut fur Diagnostikforschung GmbH an der Freien Universitat Berlin
    Inventors: Christoph-Stephan Hilger, Ludger Dinkelborg, Wolfgang Kramp, Hans-Martin Schier
  • Patent number: 5932707
    Abstract: Ligands for radiopharmaceutical use are capable of chelating radiometal species and of being bound to biological targeting molecules. The ligands have the formula (a) and (b), where A, A'=--SZ or Y, B=O or S, Y=(c), Z=H or a thiol protecting group, m=2 or 3, n=2 or 3, q=0 or 1, R=H or unsubstituted or substituted hydrocarbon and pharmaceutically acceptable salts, provided that at least one CR.sub.2 group represents CO and forms, together with an adjacent N atom; a --CONR-- amide group.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: August 3, 1999
    Assignee: Nycomed Amersham plc
    Inventors: Colin Mill Archer, Gary Robert Bower, Harjit Kaur Gill, Anthony Leonard Mark Riley, Anthony Eamon Storey, Lewis Reuben Canning, David Vaughan Griffiths
  • Patent number: 5902906
    Abstract: A mixture formed from one or more alkyl disulfides, benzene, and at least about 1.5 equivalents of Lewis acid catalyst is heated to form alkanethiobenzene. Reaction in a mixture formed from excess benzene, dimethyldisulfide (DMDS) and AlCl.sub.3 in which the mole ratio of AlCl.sub.3 to DMDS was 2:1 was complete in 2 hours and afforded 98% conversion and 93% yield of thioanisole. In contrast, the same reaction when attempted using a 1:1 mole ratio of AlCl.sub.3 to DMDS after 6 hours achieved only 66% conversion and a thioanisole yield of only 35%. So far as is known, this is the first example of a highly efficient electrophilic aromatic substitution of the inactivated benzene ring by an alkanethio group.
    Type: Grant
    Filed: May 1, 1997
    Date of Patent: May 11, 1999
    Assignee: Albemarle Corporation
    Inventors: K. Pushpananda A. Senaratne, Charles R. Everly, Won S. Park
  • Patent number: 5807814
    Abstract: Oil soluble compounds having the formula: ##STR1## wherein R and R.sup.1 are independently cyano, alkoxycarbonyl, aryloxycarbonyl, alkenyloxycarbonyl, alkylcarbonyl, arylcarbonyl, alkenylcarbonyl, alkylsulfonyl, arylsulfonyl, alkenylsulfonyl, substituted aminocarbonyl, alkylphosphoryl, arylphosphoryl, alkenylphosphoryl, aryl, or heterocyclics, or together form a carbocycle or heterocycle, and R.sup.2 and R.sup.3 are independently alkyl, alkenyl, hydroxyalkyl, sulfurized alkyl, alkoxycarbonylalkyl, arylalkyl, or borated hydroxyalkyl, with the proviso that R, R.sup.1, R.sup.2 and R.sup.3 together contain sufficient carbon atoms to render the compound oil soluble in an oil of lubricating viscosity. The compound are useful as wear protectants or extreme pressure agents to enhance wear protection or extreme pressure properties in lubricating oils and greases.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: September 15, 1998
    Assignee: Chevron Chemical Company
    Inventor: Andrew W. Ho
  • Patent number: 5770729
    Abstract: The present invention provides an ozonide reducing agent for use in the ozonolysis reaction of an organic compound, the ozonide reducing agent finding wide applications, and being safe and inexpensive from a commercial viewpoint and easy to treat for disposal.The ozonide reducing agent of the invention is a compound wherein sulfur has, at both ends of its molecule, a hydrocarbon residue substituted by a polar functional group.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: June 23, 1998
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Michio Sasaoka, Daisuke Suzuki, Takashi Shiroi
  • Patent number: 5744647
    Abstract: A process for the continuous preparation of 3-(methylthio)propanal. A liquid reaction medium is contacted with a gaseous acrolein feed stream in a gas/liquid contact zone. The reaction medium contains 3-(methylthio)propanal, methyl mercaptan and a catalyst for the reaction between methyl mercaptan and acrolein. The gaseous acrolein feed stream comprises acrolein vapor and non-condensable gas. Acrolein is transferred from the acrolein feed stream to the reaction medium and reacts with methyl mercaptan in that medium to produce a liquid reaction product containing 3-(methylthio)propanal. The non-condensable gas is separated from the liquid reaction product. The reaction product is divided into a product fraction and a circulating fraction, and the circulating fraction is recycled to the gas/liquid contact zone.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: April 28, 1998
    Assignee: Novus International, Inc.
    Inventors: Yung C. Hsu, Dennis A. Ruest
  • Patent number: 5696277
    Abstract: Lipid prodrugs of phosphonoacids and their analogs that have increased antiviral activity over the parent drugs in inhibiting cytomegalovirus and other susceptible viruses.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: December 9, 1997
    Assignee: Karl Y. Hostetler
    Inventors: Karl Y. Hostetler, Ganesh D. Kini
  • Patent number: 5689005
    Abstract: A process for the deoxygenation of organic oxo compounds, in particular phosphine oxides to phosphines and nitrobenzene to aniline, with reduced redox catalysts in a non-steady-state reaction with decoupled reductive regeneration of the redox catalyst entails the redox catalyst being reduced to a lower oxidation state and being reused for the deoxygenation.
    Type: Grant
    Filed: November 28, 1995
    Date of Patent: November 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Hagemeyer, Christopher William Rieker, Thomas Lautensack, Dieter Hermeling
  • Patent number: 5639887
    Abstract: Compounds of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are herein described, A is a straight or branched (C.sub.2 -C.sub.12)alkyl or a phenyl moiety and B is a moiety of the formula: ##STR2## The compounds are effective in potentiating the activity of chemotherapeutic anti-cancer agents by increasing the sensitivity of multi-drug resistant cells to such chemotherapeutic agents.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: June 17, 1997
    Assignee: American Cyanamid Company
    Inventors: Dennis Powell, Rolf Paul, William A. Hallett, Dan M. Berger, Minu D. Dutia
  • Patent number: 5534557
    Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3): ##STR2## where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 9, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5463138
    Abstract: Difluoromethoxyarenes and difluoromethylthioarenes of the general formula (I),Ar--Q--CHF.sub.2 (I)in whichAr represents optionally substituted aryl, andQ represents oxygen or sulphur,(which can be used as intermediates for preparing biologically active products) are obtained in very good yields and in a high degree of purity by reacting hydroxyarenes or mercaptoarenes of the general formulaAr--Q--H (II)with chlorodifluoromethane (ClCHF.sub.2) in the presence of an aqueous alkali metal hydroxide or alkaline earth metal hydroxide at temperatures of between 20.degree. C. and 120.degree. C.
    Type: Grant
    Filed: May 18, 1994
    Date of Patent: October 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus-Helmut Muller
  • Patent number: 5396011
    Abstract: An aromatic compound (such as benzene) is alkylated with a alkene (such as propylene) by contacting the two compounds together in the presence of a tungsten on zirconia catalyst. The reaction preferably takes place at elevated temperature and elevated pressure. The process of the invention has very high selectivity and conversion, and produces no or only very low amounts of undesirable oligomers (as measured by bromine number).
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: March 7, 1995
    Assignee: Mallinckrodt Chemical, Inc.
    Inventor: Deborah K. Kuhn
  • Patent number: 5393776
    Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5391650
    Abstract: A compound having at least one 2-hydroxy-1,3-propylidene, 2-acetoxy-1,3-propylidene, or 2-alkoxy-1,3-propylidene moiety between two benzocyclobutene end moieties is prepared by (a) contacting a diepoxide species with a benzocyclobutene species containing a functionality capable of reacting with an epoxy group, (b) contacting an epoxy-containing benzocyclobutene species with a species containing two functionalities capable of reacting with an epoxy group, (c) contacting an epoxy-containing benzocyclobutene species with a benzocyclobutene species containing a functionality capable of reacting with an epoxy group, (d) contacting epichlorohydrin with benzocyclobutene species capable of reacting with an epoxy group, or (e) contacting epihalohydrin with benzocyclobutene species and difunctional species, wherein both species contain functionalities capable of reacting with epoxy groups.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: February 21, 1995
    Assignee: The Dow Chemical Company
    Inventors: David J. Brennan, Jerry E. White, Daniel M. Scheck, Robert A. Kirchhoff, Charles Z. Hotz
  • Patent number: 5387718
    Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: February 7, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunther Kohler, Peter Bickert
  • Patent number: 5382686
    Abstract: Nitrodiphenyl(thio) ethers in which the nitro group is in the ortho- or para-position with respect to the ether oxygen or ether sulphur can be prepared from halonitrobenzones in which the nitro group is in the ortho- or para-position with respect to the halogen and, alkali metal (thio)phenolates in liquid ammonia, the reaction being carried out under pressure and at a temperature from -30.degree. C. to +140.degree. C. and the ammonia being separated off after the reaction is completed.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: January 17, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ferdinand Hagedorn, Helmut Fiege
  • Patent number: 5354511
    Abstract: Compounds having non-linear optical activity of the general formula ##STR1## wherein D and A are electron donor and acceptor groups, respectively, R.sup.1 and R.sup.2 are aromatic bridging groups, X and Y are preferably groups capable of partaking in polymerization reactions are suitable for use in polymer-based light modulator devices.
    Type: Grant
    Filed: November 27, 1992
    Date of Patent: October 11, 1994
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
  • Patent number: 5352758
    Abstract: A mercapto compound represented by the following formula (1): ##STR1## is obtained by reacting, in the presence of a mineral acid, thiourea with a compound represented by the following formula (2): ##STR2## wherein X means a hydroxyl group or a chlorine or bromine atom, and then adding a base to alkalinize the reaction mixture so that the reaction product is hydrolyzed.The mercapto compound represented by the formula (1) can be reacted with at least one cyanate compound selected from the group consisting of polyisocyanate compounds, polyisothiocyanate compounds and isocyanate-group-containing isothiocyanate compounds to form a sulfur- containing urethane resin. A lens made of the resin is colorless and transparent, has high refractive index and low dispersion characteristics, and is excellent especially in heat resistance.
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: October 4, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Yoshinobu Kanemura, Katsuyoshi Sasagawa, Seiichi Kobayashi
  • Patent number: 5352837
    Abstract: A process for the continuous preparation of 3-(methylthio)propanal. A liquid reaction medium is contacted with a gaseous acrolein feed stream in a gas/liquid contact zone. The reaction medium contains 3-(methylthio)propanal, methyl mercaptan and a catalyst for the reaction between methyl mercaptan and acrolein. The gaseous acrolein feed stream comprises acrolein vapor and non-condensable gas. Acrolein is transferred from the acrolein feed stream to the reaction medium and reacts with methyl mercaptan in that medium to produce a liquid reaction product containing 3-(methylthio)propanal. The non-condensable gas is separated from the liquid reaction product. The reaction product is divided into a product fraction and a circulating fraction, and the circulating fraction is recycled to the gas/liquid contact zone.
    Type: Grant
    Filed: June 8, 1993
    Date of Patent: October 4, 1994
    Assignee: Novus International, Inc.
    Inventors: Yung C. Hsu, Dennis A. Ruest
  • Patent number: 5349076
    Abstract: Disclosed is an improved method of preparation of trifluoromethylthiocopper n a very highly purified state and its application to the synthesis of organic and inorganic compounds containing the trifluoromethylthio moiety. Biological testing has shown that dimethyl(trifluoromethylthio)arsine is one of the most potent lung irritants known.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: September 20, 1994
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Shekar Munavalli, David I. Rossman
  • Patent number: 5347050
    Abstract: The compounds of formula I, ##STR1## wherein the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, are useful as cardioselective .beta.-adrenoceptor blocking agents.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: September 13, 1994
    Inventors: Richard Berthold, William J. Louis
  • Patent number: 5344959
    Abstract: Compounds of the formula ##STR1## wherein m is 1-4; R.sub.1 -R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R.sub.5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R.sub.6 is hydrogen, lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 OR NR.sub.11 --COR.sub.11 ; R.sub.20 is independently hydrogen or lower alkyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.
    Type: Grant
    Filed: May 18, 1993
    Date of Patent: September 6, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5321046
    Abstract: Disclosed herein are novel unsymmetrical dithiol ketals which are useful in the treatment or prevention of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: June 14, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: Sing-Yuen Sit, John J. Wright, Jeff A. Field
  • Patent number: 5321163
    Abstract: A multi-purpose distillation column reactor is disclosed which may be used for the production of tertiary amyl methyl ether from the reaction of the isoamylenes contained in a light naphtha with methanol. Two reaction distillation zones are disposed above a stripping section. The stripping, in addition to removing the TAME product, also removes the C.sub.6 and heavier components. The first reaction distillation zone contains a hydrotreating catalyst for removing diolefins and mercaptans. The second distillation reaction zone contains an acid cation exchange resin for the etherification reaction and the entire column serves to fractionate the multiple component reaction system (reacts, inerts, products and contaminants) concurrently with the multiple reactions.
    Type: Grant
    Filed: September 9, 1993
    Date of Patent: June 14, 1994
    Assignee: Chemical Research & Licensing Company
    Inventors: Thomas P. Hickey, John R. Adams
  • Patent number: 5283337
    Abstract: The present invention relates to a process for the preparation of perhaloalkylthioethers by bringing a perhaloalkyl halide, preferably a bromide or an iodide, into contact with a disulphide in the presence of zinc and of sulphur dioxide or of a dithionite or of a hydroxymethanesulphinate or of a formate anion and sulphur dioxide.
    Type: Grant
    Filed: November 8, 1991
    Date of Patent: February 1, 1994
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Claude Wakselman, Marc Tordeux, Bernard Langlois, Jean-Louis Clavel, Roland Nantermet
  • Patent number: 5283312
    Abstract: A mercapto compound represented by the following formula (1): ##STR1## is obtained by reacting, in the presence of a mineral acid, thiourea with a compound represented by the following formula (2): wherein X means a hydroxyl group or a chlorine or bromine atom, and then adding a base to alkalinize the reaction mixture so that the reaction product is hydrolyzed.The mercapto compound represented by the formula (1) can be reacted with at least one cyanate compound selected from the group consisting of polyisocyanate compounds, polyisothiocyanate compounds and isocyanate-group-containing isothiocyanate compounds to form a sulfur-containing urethane resin lens made of the resin is colorless and transparent, has high refractive index and low dispersion characteristics, and is excellent especially in heat resistance.
    Type: Grant
    Filed: August 4, 1992
    Date of Patent: February 1, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoshinobu Kanemura, Katsuyoshi Sasagawa, Seiichi Kobayashi
  • Patent number: 5274002
    Abstract: Novel trisubstituted phenyl analogs are now found to have activity as for the treatment of congestive heart failure.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: December 28, 1993
    Assignee: Warner-Lambert Company
    Inventor: Lynn D. Hawkins
  • Patent number: 5225601
    Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: October 31, 1991
    Date of Patent: July 6, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5219562
    Abstract: A hair treating composition comprising one or more thioglyceryl ethers provides effective wave formation, with a minimized mercapto smell and minimized irritation to the skin.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: June 15, 1993
    Assignee: Kao Corporation
    Inventors: Akira Fujiu, Naohisa Kure, Yoshiko Ogura
  • Patent number: 5216049
    Abstract: The present invention relates to an antidegradant system comprised of (A) an antidegradant selected from the group consisting of phenolic antidegradants, amine antidegradants and mixtures thereof; and (B) a unique polymerizable synergist. In addition, there is disclosed a stabilized polymer comprising (A) a polymer selected from the group consisting of (1) homopolymers and copolymers of monoolefins; (2) natural rubber; and (3) synthetic rubber derived from a diene monomer; (B) from about 0.05 to about 10 parts by weight based upon 100 parts of polymer of an antidegradant selected from the group consisting of phenolic antidegradants, amine antidegradants and mixtures thereof; and (C) from about 0.05 to about 20 parts by weight based upon 100 parts of polymer of a unique polymerizable aromatic sulfide synergist.
    Type: Grant
    Filed: September 18, 1992
    Date of Patent: June 1, 1993
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Dane K. Parker, Gerald O. Schulz
  • Patent number: 5196536
    Abstract: A novel class of cross-linking agent, which comprises a monomeric organic compound having at least two hydroxyl groups each bonded to a different carbon atom, wherein said hydroxyl groups are activated by reaction with 2-fluoro-1-methylpyridinium toluene-4-sulfonate (FMP). Suitable monomeric organic compounds include diols and polyols. Such cross-linking agents may be conveniently prepared by reaction of the monomeric organic compound with FMP in a suitable solvent, followed by recovery of the resultant reaction products, e.g., via precipitation and filtration. The novel cross-linking agents have a wide variety of uses, including the interconnection of subunits of multimeric enzymes and the covalent immobilization of organic ligands to suitable carriers or supports.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: March 23, 1993
    Assignee: UniSyn Fibertec Corporation
    Inventors: That T. Ngo, Faizy Ahmed
  • Patent number: 5162585
    Abstract: A process for preparing a dihydroxy bis-sulfide is disclosed, wherein a thiolate salt, a dihaloalkane, an ether solvent that is partially soluble in water and is substantially nonreactive with either said thiolate salt or said dehaloalkane; and water are contacted under reaction conditions sufficient to synthesize a dihydroxy bis-sulfide; to subsequently recover a dihydroxy bis-sulfide.
    Type: Grant
    Filed: April 8, 1991
    Date of Patent: November 10, 1992
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5132423
    Abstract: Reactions between a solid polar and a non-polar compound, especially nucleophilic aromatic substitution reactions between an alkali metal salt of a hydroxyaromatic compound or thio analog thereof and an activated halo- or nitro-substituted aromatic compound, are conducted in a non-polar organic solvent such as toluene or xylene, in the presence of a hexaalkylguanidinium or .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salt, or a corresponding heterocyclic salt, as a phase transfer catalyst. The method is particularly useful for the preparation of bisimides from bisphenol A or 4,4'-biphenol salts and 4-nitro- or 4-halophthalimides.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: July 21, 1992
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Deborah A. Haitko, James P. Barren, Sunita Singh
  • Patent number: 5116916
    Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: May 26, 1992
    Assignee: Union Oil Company of California
    Inventor: Donald C. Young
  • Patent number: 5100460
    Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5084214
    Abstract: Phenolic thioethers of the formula: ##STR1## wherein R is a hydrogen atom or a protective group for carboxyl, X is a straight or branched C.sub.4 -C.sub.15 alkylene group, a straight or branched C.sub.1 -C.sub.15 alkylene group having a phenylene group or a straight or branched C.sub.2 -C.sub.15 alkenylene group, and their salts, which inhibit the denaturation of low density lipoproteins (LDL) and the incorporation of LDL by macrophages and are useful as anti-arteriosclerosis agents.
    Type: Grant
    Filed: May 31, 1989
    Date of Patent: January 28, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Toru Kita, Shuh Narumiya, Masayuki Narisada, Fumihiko Watanabe, Saichi Matsumoto, Masami Doteuchi
  • Patent number: 5082945
    Abstract: The present invention relates to a process for the preparation of perhaloalkylthioethers by bringing a perhaloalkyl halide, preferably a bromide or an iodide, into contact with a disulphide in the presence of zinc and of sulphur dioxide or of a dithionite or of a hydroxymethanesulphinate or of a formate anion and sulphur dioxide.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: January 21, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Claude Wakselman, Marc Tordeux, Bernard Langlois, Jean-Louis Clavel, Roland Nantermet
  • Patent number: 5082974
    Abstract: 3-Haolgeno-2,3-diphenylacrylaldehyde derivatives represented by the formula ##STR1## wherein R is an alkyl group having 1 to 6 carbon atoms, X and Y each represent a halogen atom, and n is 0, 1, or 2, a process for preparing the derivatives, a medicament for preventing and treating hyperlipidemia containing a pharmacologically effective amount of the derivative, and a method for preventing or treating hyperlipidemia using the medicament.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: January 21, 1992
    Assignee: Otsuka Pharaceutical Factory, Inc.
    Inventors: Kinji Hashimoto, Makoto Inoue, Junichi Minamikawa
  • Patent number: 5047420
    Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: September 10, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
  • Patent number: 4964957
    Abstract: A process for preventing the substantial decomposition of an alkyl sulfide compound at high temperatures comprising combining a non-reactive basic compound with the alkyl sulfide compound prior to subjecting the resultant mixture to the high temperatures.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: October 23, 1990
    Assignee: Phillips Petroleum Company
    Inventors: James E. Shaw, John S. Roberts
  • Patent number: 4937388
    Abstract: The invention provides insecticidally active compounds of formula I: ##STR1## wherein A is selected from oxygen and a group of formula S(O).sub.n, where n represents 0, 1 or 2; W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms, selected from alkylene and alkylenedioxy; Y represents a substituted aryl group where each substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; Z represents a fluoroalkyl group of up to two carbon atoms; and either X' represents hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and acyloxy, or X and X' together represent a second bond between the adjacent carbon atoms.The invention also provides processes and intermediates useful for the preparation of the compounds of formula I, insecticidal compositions comprising the compounds of formula I, and methods of combating and controlling pests therewith.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: June 26, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 4894174
    Abstract: The present invention deals with compositions containing sulfur and oxygen which are useful in lubricants and automatic transmission fluids.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: January 16, 1990
    Assignee: The Lubrizol Corporation
    Inventor: Mary F. Salomon
  • Patent number: 4889955
    Abstract: ar-(Hydrocarbylthio)aromatic amines, such as (alkylthio) anilines, are prepared by heating one or more other ar-(hydrocarbylthio)aromatic amines in the presence of a catalyst, such as aluminum chloride, to redistribute the hydrocarbylthio groups with little or no co-formation of secondary or tertiary amines. The amine starting material is one or more primary aromatic amines having at least one free ring position and at least one hydrocarbylthio substituent in a ring position other than a meta-position.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: December 26, 1989
    Assignee: Ethyl Corporation
    Inventor: Paul F. Ranken
  • Patent number: 4876376
    Abstract: A process for the halogenation (bromination or chlorination)/nitration/fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with a halogen and a nitrating agent in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Specialistes Chimiques
    Inventors: Michael Desbois, Camille Disdier
  • Patent number: 4833164
    Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: May 23, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Douglas G. Batt
  • Patent number: 4795831
    Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopetanecarbonyl)-R-1,1-diaminoet hane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxymethylene, or --CH.sub.2 --O--.
    Type: Grant
    Filed: October 1, 1987
    Date of Patent: January 3, 1989
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
  • Patent number: 4727156
    Abstract: 3-(Substituting phenyl)-3-(1H-imidazol-1-ylmethyl)-2-methyl-5-{[(substituted phenyl)thio]m ethyl}isoxazolidines in which hydrogens of their phenyl rings may be replaced by halogen, lower alkoxy, lower alkyl or nitro groups, and the sulfur atom may be oxidized, are useful as antifungal agents.
    Type: Grant
    Filed: August 27, 1986
    Date of Patent: February 23, 1988
    Assignee: Pennwalt Corporation
    Inventors: Vassil St. Georgiev, George B. Mullen
  • Patent number: 4727191
    Abstract: A (hydrocarbylthio)aromatic amine, such as a methylthiosubstituted toluenediamine, is separated from corresponding aromatic amines containing fewer hydrocarbylthio groups by washing an organic solution of the amine mixture with a dilute aqueous acid having a pKa value below 7 to extract at least a portion of the corresponding aromatic amines.
    Type: Grant
    Filed: July 10, 1986
    Date of Patent: February 23, 1988
    Assignee: Ethyl Corporation
    Inventor: Christopher J. Nalepa
  • Patent number: 4716241
    Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxy-methylene, or --CH.sub.2 --O--.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: December 29, 1987
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
  • Patent number: 4700005
    Abstract: Phenolic ethers are produced by reacting a phenol with a compound selected from an alkyl halide, an aryl halide, a dialkyl sulphate and a diaryl sulphate in the presence as catalyst of an amidine.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: October 13, 1987
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green