Ketones Patents (Class 568/303)
  • Patent number: 6229048
    Abstract: A method for treating cancer comprising administering a 1,3,4,6-tetrahydroxy-helianthrone derivative. The compounds can be used in the absence of light irradiation or for photodynamic therapy of solid tumors wherein the tumor site is subjected to light irradiation after administration of the active ingredient. A preferred compound is 10,13-dimethyl-1,3,4,6-tetrahydroxy-helianthrone.
    Type: Grant
    Filed: January 31, 2000
    Date of Patent: May 8, 2001
    Assignees: Yeda Research and Development Co. Ltd. at the Weizmann Institute of Science, New York University
    Inventors: Yehuda Mazur, Gad Lavie
  • Patent number: 6211397
    Abstract: A process for the preparation of &agr;-chloromethylene-triorganylphosphorane derivatives I (radicals R are C-organic substituents and A stands for CN or CO-B where B is a C-organic or O-organic radical which is inert under chlorination conditions) by chlorination of phosphoranes II with chlorine, wherein the chlorination is carried out in the presence of a mineral base as hydrogen chloride acceptor and the chlorine and base are fed to the reaction mixture concurrently but separately at the rates at which they are consumed. The reaction products I are important intermediates for plant protectants.
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: April 3, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Schaefer, Ernst Buschmann, Gernot Reissenweber
  • Patent number: 6191171
    Abstract: para-Aminomethylaryl carboxamides of Formula I are antagonists of VLA-4 and/or &agr;4&bgr;7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of asthma, allergies, inflammation, multiple sclerosis, and other inflammatory and autoimmune disorders.
    Type: Grant
    Filed: November 13, 1998
    Date of Patent: February 20, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Stephen E. DeLaszlo, William K. Hagmann
  • Patent number: 6162926
    Abstract: The invention is directed to multiply-substituted fullerene derivatives of novel configurations, and methods for their preparation and use. The methods involve the combinatorial synthesis of a library of fullerene derivatives and comprises the steps of forming a mixture of fullerene derivatives by reacting the C.sub.n fullerene with two or more reactive precursor compounds, and removing the unreacted compounds to yield the fullerene derivatives having the desired activity. Methods for the identification and screening of a combinatorial library of fullerenes by .sup.3 He-nuclear magnetic resonance and electrospray mass spectrometry to define members with the optimal desired activity are also provided.
    Type: Grant
    Filed: November 13, 1997
    Date of Patent: December 19, 2000
    Assignee: Sphere Biosystems, Inc.
    Inventors: Randall B. Murphy, Stephen R. Wilson, Quing Lu
  • Patent number: 6156429
    Abstract: The invention concerns monomers with dilactonic cycle and the corresponding polymers, their preparation, and materials containing these polymers. The monomers are of formula (IIIa) ##STR1## in which R is the residue of an acid derived from an ose such as glyconic, gylcuronic or glycaric acid and X represents in particular a methylene or ethylene group optionally substituted by at least an alkyl, allyl, aryl or aralkyl. The corresponding polymers are in the form of degradable non-toxic products and are used for example for packaging (films) or in medicine (implants).
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: December 5, 2000
    Assignee: Centre National de la Recherche Scientifique (CNRS)
    Inventors: Katarina Marcincinova, Mahfoud Boustta, Jean Coudane, Michel Vert
  • Patent number: 6127140
    Abstract: A method for determining concentration of an analyte in a biological sample comprising the steps of:(a) combining the biological sample, at least one oxidizing enzyme for the analyte of interest, nicotinamide adenine dinucleotide (hereinafter NAD.sup.+), and a chemiluminescent label to form a reaction mixture;(b) allowing the analyte to undergo an oxidation-reduction reaction and NAD.sup.+ to be converted to the reduced form of nicotinamide adenine dinucleotide (hereinafter NADH) and further allowing the chemiluminescent label to react with NADH; and(c) determining the concentration of the analyte of interest in the biological sample by correlating the quantity of light emitted with the concentration of NADH.
    Type: Grant
    Filed: June 18, 1999
    Date of Patent: October 3, 2000
    Assignee: Abbott Laboratories
    Inventors: Momcilo S. Vidakovic, David C. Leahy, Donna M. Massie
  • Patent number: 6114493
    Abstract: This invention relates to methods for preparing novel, solid-phase transfer reagents, specifically phosgenated oxime resins and non-symmetrical ureas, that are useful as supports in combinatorial synthesis for the creation of libraries of compounds for lead identification.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: September 5, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Mark Andrew Scialdone
  • Patent number: 6054490
    Abstract: The invention relates to the use of a sesquiterpene for inhibiting an oxidative enzyme, preferably a cytochrome P450 enzyme. The invention also relates to compositions comprising a sesquiterpene and a drug which exhibits instability in the presence of an oxidative enzyme.
    Type: Grant
    Filed: April 10, 1998
    Date of Patent: April 25, 2000
    Assignee: Zylepsis Limited
    Inventors: John Thomas Sime, Peter Samuel James Cheetham, Michelle Lorraine Gradley, Nigel Eric Banister
  • Patent number: 6037501
    Abstract: By subjecting an aromatic compound of the formula (I), which is an inexpensive raw material, to a vapor-phase intramolecular cyclodehydrogenation reaction, fluorenes of the formula (II) can be obtained industrially advantageously in a high yield. Fluorenes (II) are expected to be used as raw materials for heat-resistant epoxy resins, polycarbonates or polyesters. wherein R.sub.1 and R.sub.2 each represent a hydrogen atom, a methyl group or an ethyl group, or R.sub.1 and R.sub.2 represent .dbd.O at the same time; and R and R' each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: June 6, 1998
    Date of Patent: March 14, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Noboru Saito, Toshiya Iida, Isamu Maeda
  • Patent number: 6025323
    Abstract: The compounds of formula ##STR1## in which R stands for a methyl or ethyl group, are used as perfume ingredients for the preparation of perfuming compositions and perfumed articles, to which they confer aromatic and thujonic notes. The compounds can be used in the form of a mixture of enantiomers or in an enantiomerically pure state. The invention also comprises original processes for the preparation of these compounds.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: February 15, 2000
    Assignee: Firmenich SA
    Inventors: Charles Fehr, Christian Margot
  • Patent number: 5998330
    Abstract: A method of treating vegetation by application of a microbial insecticide in which a quinone has been covalently bonded to the viral occlusion body surface of the microbial insecticide in order to improve the UV stability of the microbial insecticide by forming a protective shield around the pathogen.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: December 7, 1999
    Assignee: The Board of Trustees of the University of Arkansas
    Inventor: Gary W. Felton
  • Patent number: 5994392
    Abstract: The invention involves the formation of a prodrug from a fatty acid carrier and a neuroactive drug. The prodrug is stable in the environment of both the stomach and the bloodstream and may be delivered by ingestion. The prodrug passes readily through the blood brain barrier. Once in the central nervous system, the prodrug is hydrolyzed into the fatty acid carrier and the drug to release the drug. In a preferred embodiment, the carrier is 4, 7, 10, 13, 16, 19 docosahexa-enoic acid and the drug is dopamine. Both are normal components of the central nervous system. The covalent bond between the drug and the carrier preferably is an amide bond, which bond may survive the conditions in the stomach. Thus, the prodrug may be ingested and will not be hydrolyzed completely into the carrier molecule and drug molecule in the stomach.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: November 30, 1999
    Assignee: Neuromedica, Inc.
    Inventor: Victor E. Shashoua
  • Patent number: 5968482
    Abstract: The invention relates to the use of .alpha.-hydroxyketoalkyl derivatives as light protection filters for cosmetic or pharmaceutical products, the .alpha.-hydroxyketoalkyl group being linked, if appropriate via a spacer, to a chromophoric group which has an absorption maximum in a wavelength range of between 280 and 400 nm and has a conjugated .pi.-electron system of at least 8 .pi.-electrons, and to new .alpha.-hydroxyalkyl derivatives, processes for their preparation and pharmaceutical and cosmetic formulations comprising these derivatives as light protection substances.
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: October 19, 1999
    Assignee: Merck Patent Gesellschaft MIT Beschrankter Haftung
    Inventors: Roland Martin, Ingeborg Stein, Ulrich Heywang, Michael Schwarz, Thekla Kurz
  • Patent number: 5907069
    Abstract: In producing nabumetone or precursor thereof, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl bromide or methyl chloride, in a halogen-free liquid solvent comprising at least about 40% by weight of one or more compounds of the formula RZ where R is a hydrogen atom or an alkyl group, and Z is a hydroxyl group or a cyanide group with the proviso that if Z is a cyanide group, R is an alkyl group, and in the presence of at least one strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: May 25, 1999
    Assignee: Albemarle Corporation
    Inventors: Brian F. Becnel, Mahmood Sabahi, Kevin J. Theriot
  • Patent number: 5858738
    Abstract: Natural products such as certain ermophilane sesquiterpenoids and derivatives thereof are described. These compounds are useful in the inhibition of HIV integrase, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. The fungal culture MF6254, Xylaria sp. (ATCC 74397) is also described and disclosed.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: January 12, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Russell B. Lingham, Jon David Polishook, Ali Shafiee, Keith C. Silverman, Sheo Bux Singh, Deborah L. Zink
  • Patent number: 5852160
    Abstract: This invention relates to methods for preparing novel, solid-phase transfer reagents, specifically phosgenated oxime resins and non-symmetrical ureas, that are useful as supports in combinatorial synthesis for the creation of libraries of compounds for lead identification.
    Type: Grant
    Filed: August 19, 1997
    Date of Patent: December 22, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Mark Andrew Scialdone
  • Patent number: 5675038
    Abstract: The invention is directed to a process for reducing or reductively cleaving an organic compound susceptible to dissolving metal reduction comprising exposing the organic compound to a solution of lithium in a polyamine including at least two amino groups, selected from the group consisting of primary and secondary amino groups and mixtures thereof, e.g. ethylenediamine and R--NH.sub.2, optionally containing a lower alkyl alcohol, wherein R is chosen from the group consisting of ethyl, propyl, and butyl, including all straight and branched chain isomers thereof, for a time sufficient to effect reduction.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: October 7, 1997
    Assignee: Allergan
    Inventors: Lloyd J. Dolby, Nestor A. Fedoruk, Shervin Esfandiari, Natalie C. Chamberlain, Michael E. Garst
  • Patent number: 5604262
    Abstract: A method to inhibit microbial growth is provided comprising topically administering to a mammal afflicted with a pathology associated with microbial growth, such as a dermatological condition, an effective amount of a linear (C.sub.12 -C.sub.22) 3-alken-2-one or 3,.omega.-alkadien-2-one.
    Type: Grant
    Filed: March 22, 1995
    Date of Patent: February 18, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventor: William F. Wood
  • Patent number: 5552218
    Abstract: The invention relates to polyketone yarns of which the maximum tangential modulus at an elongation of more than 0.2% is at least 10 N/tex which display both high strength and, if so desired, a high elongation at break. The quality number, which is measured on a single filament out of a bundle of at least about 30 filaments spun simultaneously through one spinneret and given as .sigma...epsilon., is higher than 85 mN/tex, preferably higher than 100 mN/tex. The quality number of a yarn spun through one spinneret of one or more holes is higher than 110 mN/tex, preferably higher than 120 mN/tex. The yarns are manufactured by extruding a solution of a linear polymer of alternating ethylene and carbon monoxide units in a resorcinol-containing solvent, after which the solvent is removed with the aid of methanol as coagulant.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: September 3, 1996
    Assignee: Akzo Nobel N.V.
    Inventors: Hendrik T. Maat, Peter J. Cloos, Harm Van Der Werff, Bert J. Lommerts
  • Patent number: 5523509
    Abstract: Synthetic manganese oxide octahedral molecular sieves, e.g., OMS-1 and OMS-2, are employed as acid-base catalysts in a variety of acid-base organic conversion reactions.
    Type: Grant
    Filed: November 7, 1994
    Date of Patent: June 4, 1996
    Assignee: Texaco Inc.
    Inventors: Chi-Lin O'Young, Robert A. Sawicki, Yan-Fei Shen, Steven L. Suib
  • Patent number: 5514675
    Abstract: This invention provides methods of treating a physiological disorder associated with an excess of bradykinins in a mammal which comprises administering to a mammal in need of said treatment a compound selected from a series of substituted dihydronaphthalenes and naphthalenes.
    Type: Grant
    Filed: October 20, 1994
    Date of Patent: May 7, 1996
    Assignee: Eli Lilly and Company
    Inventors: Robert F. Bruns, Jr., Donald R. Gehlert, J. Jeffry Howbert, William H. W. Lunn
  • Patent number: 5462810
    Abstract: A magnetic recording medium comprises a nonmagnetic substrate and at least one ferromagnetic metal layer applied thereon and a protective layer formed on this metal layer and consisting of a compound which consists of an unfluorinated or partially fluorinated alkyl radical and a disulfide, hydroxyl or keto group.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: October 31, 1995
    Assignee: BASF Magnetics GmbH
    Inventors: Harald Keller, Ulrich Jaeger, Helmut Steininger, Helmut Kopke, Klaus D. Schomann, Hans-Peter Schildberg
  • Patent number: 5371295
    Abstract: A new process for the preparation of 1-fluorocyclopropyl methyl ketone of the formula ##STR1## which process comprises a) in a first step, reacting 2-acetyl-2-chloro-4-butanolide of the formula ##STR2## with an addition product of triethylamine and hydrogen fluoride of the formula(C.sub.2 H.sub.5).sub.3 N.n HFin whichn represents the numbers 1, 2 or 3, in the presence of a diluent at a temperature between 20.degree. C. and 120.degree. C. andb) in a second step, reacting the resulting 2-acetyl-2-fluoro-4-butanolide of the formula ##STR3## with a nucleophilic agent in the presence of a diluent at a temperature between 50.degree. C. and 200.degree. C.New halogenoketones of the formula ##STR4## in which Hal represents chlorine or bromine.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: December 6, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Bohm, Albrecht Marhold
  • Patent number: 5352822
    Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Robert J. Blade, George S. Cockerill, John E. Robinson
  • Patent number: 5264632
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: December 8, 1992
    Date of Patent: November 23, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5258547
    Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5113021
    Abstract: A process for the manufacture of .alpha.- and .beta.-irone, namely the compounds of formula I, as well as novel intermediates in the process is provided.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: May 12, 1992
    Assignee: Givaudan Corporation
    Inventors: Georg Frater, Daniel Helmlinger
  • Patent number: 5094701
    Abstract: This invention is a residue-free cleaning process for removing metal-containing contaminants from a surface of a substrate of the type used in manufacturing semi-conductor devices. The process comprises contacting the substrate with an effective amount of a cleaning agent comprising a .beta.-diketone or .beta.-ketoimine dispersed in an atmosphere capable of oxidizing the metal-contaminants at a temperature sufficient to form volatile metal-ligand complexes on the surface of the substrate. The volatile metal-ligand complexes are sublimed from the surface of the substrate leaving essentially no residue.
    Type: Grant
    Filed: April 1, 1991
    Date of Patent: March 10, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John A. T. Norman, John C. Ivankovits, David A. Roberts, David A. Bohling
  • Patent number: 5095147
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5081283
    Abstract: Novel intermediates for fungicides, comprising fluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl,X represents hydrogen, chlorine or bromine andR.sup.1 represents hydroxyl, alkoxy, alkyl or halogen.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: January 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 4992577
    Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4943384
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 24, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
  • Patent number: 4912134
    Abstract: Azulene derivatives of the following formula ##STR1## wherein R.sup.1 stands for an alkyl group of 1 to 3 carbon atoms, R.sup.2 stands for an alkyl group of 1 to 3 carbon atoms, and R.sup.3 is at the 5- or 6-position and stands for an alkyl group of 1 to 6 carbon atoms, an aryl group of 6 to 9 carbon atoms or an aralkyl group of 7 to 10 carbon atoms; have antihyperlipidemic activity. Many of the compounds are also novel per se.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: March 27, 1990
    Assignee: Ajinomoto Company, Inc.
    Inventors: Masabumi Yasunami, Kahei Takase, Takashi Meguro, Katsumi Suzuki, Osamu Hiwatashi, Masaru Okutsu, Nobuo Kato, Toru Nakamura
  • Patent number: 4894483
    Abstract: Vinylglyoxal derivatives of the general formula I ##STR1## where R is straight-chain or branched alkyl or alkenyl, cycloalkyl or unsubstituted or substituted phenyl, are prepared by a process in which bicyclo[2.2.1]hept-5-enecarbaldehyde of the formula V ##STR2## is either (a) subjected to autocondensation with formation of a compound of the formula VII ##STR3## or (b) reacted with a compound of the general formula IIR-CH.dbd.O (II)where R has the above meanings, with formation of a mixture of the compounds of the general formulae VIII (a) and (b) ##STR4## where R is as defined above, in the presence of a catalyst, and the compound of the formula VII or the compounds of the formulae VIII (a) and (b) is or are oxidized to the corresponding dicarbonyl compounds, after which gas-phase pyrolysis is carried out at from 500.degree. to 700.degree. C. and under reduced pressure, in particular less than 10.sup.-1 mbar, and, if desired, the resulting compound of the general formula I is further purified.
    Type: Grant
    Filed: October 28, 1987
    Date of Patent: January 16, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Hans-Dieter Martin, Roland Kramme, Ralf T. Weimann
  • Patent number: 4855460
    Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Tordeux, Claude Wakselman, Catherine Francese
  • Patent number: 4845129
    Abstract: The invention discloses certain diaryl substituted cyclopentane and cyclopentene derivatives useful as PAF inhibitors, pharmaceutical compositions containing said compounds as an active ingredient thereof and a method of using such compositions for inhibiting PAF-induced blood platelet aggregation, PAF-mediated broncho-constriction and extravasation, PAF-induced hypotension, PAF-induced ischemic bowel disease and PAF-mediated, endotoxin induced lug injury.
    Type: Grant
    Filed: March 14, 1988
    Date of Patent: July 4, 1989
    Assignee: Sandoz Pharm. Corp.
    Inventors: Robert C. Anderson, William J. Houlihan, Howard C. Smith, Edwin B. Villhauer
  • Patent number: 4740612
    Abstract: A novel process for producing a .beta.-dihalogenoethenylcyclopropane derivative of the formula, ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl group, R.sub.3 is a hydrogen atom, lower alkyl, acyl, carboxyl or alkoxycarbonyl group and R is a hydrogen atom or a lower alkyl group and each of Y.sub.1 and Y.sub.2 is a fluorine, chlorine or bromine atom respectively, which is an acidic moiety of the useful synthetic insecticides of the pyrethrin type, which process comprises a combination of a series of sequential steps starting from alkyl 3-butenyl ketone derivative of the formula (I), which may be shown according to the following reaction scheme: ##STR2## According to this process, objective compound of the formula (VI) having any cis/trans ratio can be produced by selecting the reaction condition of the Stages II-1, II-2, and IV-2.
    Type: Grant
    Filed: February 5, 1986
    Date of Patent: April 26, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Matsuo, Nobushige Itaya, Osamu Magara
  • Patent number: 4737482
    Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidiation of the olefin in the presence of molecular oxygen and water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: April 12, 1988
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4528142
    Abstract: Described are 1-hydroxymethyl-2-acyl cyclopropane derivatives having one of the structures: ##STR1## and utilities thereof for their organoleptic properties.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: July 9, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna, Theodore J. Tyszkiewicz
  • Patent number: 4518797
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: May 21, 1985
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4500448
    Abstract: Described are 1-hydroxymethyl-2-acyl cyclopropane derivatives defined according to the structure: ##STR1## wherein Z represents hydrogen, acyl having the structure: ##STR2## and substituted oxyacyl having the structure: ##STR3## and cyclic condensation products thereof having the structure: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 represent C.sub.1 -C.sub.10 alkyl; wherein R.sub.1 ' represents C.sub.1 -C.sub.10 alkylidene and wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or C.sub.1 -C.sub.3 lower alkyl; processes for preparing same by means of a reaction of a halomethyloxirane or substituted halomethyloxirane with a substituted 1,3-propanedione derivative; and organoleptic uses of such 1-hydroxymethyl-2-acyl cyclopropane derivatives in augmenting or enhancing the aroma or taste of perfume compositions, perfumed articles (e.g.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: February 19, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna, Theodore J. Tyszkiewicz
  • Patent number: 4481225
    Abstract: Described is the use of the compound having the structure: ##STR1## in augmenting or enhancing the aroma or taste of foodstuffs.
    Type: Grant
    Filed: November 30, 1983
    Date of Patent: November 6, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna, Theodore J. Tyszkiewicz
  • Patent number: 4324915
    Abstract: Novel pyrethroid intermediates ##STR1## wherein R.sup.1 and R.sup.2 each is alkyl are prepared by treating 2,2-dimethyl-3-(2-oxopropyl)cyclopropylacetaldehyde with a trialkylsilyldialkylamine. The above compounds can be treated with ozone to form 2,2-dimethyl-3-(2-oxopropyl)cyclopropanecarbaldehyde.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: April 13, 1982
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4314072
    Abstract: 2-(2-Hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde and certain derivatives thereof are useful intermediates for the preparation of dihalovinyl-type pyrethroid esters.
    Type: Grant
    Filed: November 23, 1979
    Date of Patent: February 2, 1982
    Assignee: Shell Oil Company
    Inventor: Johannes L. M. Syrier
  • Patent number: 4298757
    Abstract: 2-(2,2-Dihalovinyl-3,3-dimethylcyclopropyl)vinyl alkanoates in which the alkanoate moiety contains from two to six carbon atoms are new chemical compounds useful as intermediates in the preparation of certain pyrethroid acids. The alkanoates are prepared by reacting 2-(2,2-dihalovinyl-3,3-dimethylcyclopropyl)ethanal with the appropriate alkanoic acid anhydride.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: November 3, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4298756
    Abstract: Preparation of novel alkyl 2,2-dihalovinylcyclopropylacetates (intermediates in the preparation of insecticides) by reaction of a phosphine with a compound generating a dihalocarbene and reaction of the product resulting therefrom with an alkyl formylcyclopropylacetate, both reactions being carried out in a solvent.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: November 3, 1981
    Assignee: Shell Oil Company
    Inventors: Pieter A. Verbrugge, Petrus A. Kramer
  • Patent number: 4296226
    Abstract: Vinyl polymers with acetylacetoxy groups form the basis of polymer dispersions which are used as binding agent dispersions in paints, particularly suitable vinyl polymers are obtained by polymerizing an acetylacetoxy compound together with a least one further olefinically unsaturated compound, while using as acetylacetoxy compound an allyl ether derivative of the formula ##STR1## The copolymerization is carried out in particular in emulsion at a temperature in the range of from -30.degree. to 200.degree. C. As comonomers there are used especially vinyl esters and (meth-)acrylic acid esters. The polymerization is commonly effected in the presence of a radical-forming initiator and optionally in the presence of emulsifiers and protective colloids.
    Type: Grant
    Filed: July 9, 1980
    Date of Patent: October 20, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Braun, Helmut Rinno, Karl J. Rauterkus
  • Patent number: 4281203
    Abstract: New compounds of formula: ##STR1## wherein R.sup.1 is an alkyl group and R.sup.2 a 2-oxopropyl group or a 2,2-dihalovinyl group are prepared by elimination of an alcohol R.sup.1 OH from an acetal of formula: ##STR2## The compounds are intermediates in route to pyrethroid insecticides.
    Type: Grant
    Filed: May 28, 1980
    Date of Patent: July 28, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes L. M. Syrier, Johannes Van Berkel
  • Patent number: 4258207
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman