Polyoxy Patents (Class 568/648)
  • Publication number: 20090036542
    Abstract: The present invention provides compounds represented by formula (1) shown below: (wherein R1, R2, R3, R4, and R5 are each individually selected from among a hydrogen atom, methyl group, acetyl group, hydroxyl group, and alkoxy group; and X represents an alkylene group or alkenylene group); and compounds represented by formula (2) shown below: (wherein R6, R7, R8, R9, and R10 are each individually selected from among a hydrogen atom, alkyl group, acetyl group, hydroxyl group, and alkoxy group; A represents an oxygen atom or NH, and m is 0 or 1; and Y represents an alkylene group or alkenylene group, and Z represents a hydrogen atom or hydroxyl group). The compounds of the present invention are useful for preventing or treating brain dysfunctions, motor dysfunctions, or urinary dysfunctions caused by the degeneration and/or loss of the central nervous system or peripheral nervous system cells.
    Type: Application
    Filed: February 23, 2006
    Publication date: February 5, 2009
    Inventors: Bang Luu, Dominique Bagnard, Mazen Hanbali, Masashi Yamada, Hiroto Suzuki
  • Publication number: 20080228010
    Abstract: This invention provides an alkoxylation process for creating alkoxylating chain extension of phenolic compounds by reacting phenolic compounds with alkylene glycol and urea in the presence of suitable catalysts to obtain alkoxylated compounds, which may be used as polymer intermediates, especially for use as raw materials to synthesize polyurethane (PU) or polyester.
    Type: Application
    Filed: October 30, 2007
    Publication date: September 18, 2008
    Inventors: Shenghong A. Dai, Hsing-Yo Lin, Chien-Sheng Wen
  • Patent number: 7422702
    Abstract: The present invention provides, in a method for transporting charge using the molecular orientation in a liquid-crystalline state, a novel benzene derivative having a long, linear conjugated structure expected to have satisfactory charge-transport properties without photoexcitation, a process for producing the benzene derivative, and a liquid-crystal material including the benzene derivative.
    Type: Grant
    Filed: March 22, 2004
    Date of Patent: September 9, 2008
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventor: Yuichiro Haramoto
  • Patent number: 7393465
    Abstract: A process for preparing hydrophobic polyols that includes reacting A) a mixture having an OH content of from 180 to 300 mg KOH/g, a viscosity at 23° C. of from 5000 to 20 000 mPas and an OH functionality of from 2.8 to 4.5 including from 5 to 20 wt. % of 3-pentadecadienylphenol, from 5 to 10 wt. % of 3-pentadecadienyl-recorcinol and from 1 to 5 wt. % of 2-methyl 3-pentadecadienylrecorcinol; with B) alkylene oxides (AO) with addition of the AO monomers onto the AO-reactive groups of component A); the ratio of the amounts of A) to B) being from 1:9 to 9:1; where the hydrophobic polyols have an OH number of from 140 to 220 mg KOH/g and a viscosity at 23° C. of from 1000 to 4000 mPas. The hydrophobic polyols can be used in polyurethane systems, in coatings, adhesive bonds, sealants or moulding compounds, which can be used to coat substrates.
    Type: Grant
    Filed: February 24, 2005
    Date of Patent: July 1, 2008
    Assignee: Bayer MaterialScience AG
    Inventors: Meike Niesten, Jack Reese, Joachim Simon, Gerhard Ruttmann
  • Patent number: 7230141
    Abstract: A process for preparing toluene derivatives of the formula I, where R1, R2 and R3 independently of one another are hydrogen, halogen, C1–C6-alkyl, hydroxyl or C1–C6-alkoxy, by hydrogenating benzaldehydes and/or benzyl alcohols of the formula II, with hydrogen in the presence of a catalyst, which is described in more detail in the description.
    Type: Grant
    Filed: January 20, 2003
    Date of Patent: June 12, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
  • Patent number: 7208639
    Abstract: The present invention provides a method for obtaining reduced coenzyme Q10 which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. suited for a commercial scale production in high quality and efficiently. The high-quality oily reduced coenzyme Q10 which has low viscosity and thereby easily handled may be produced by separating an aqueous phase from the reaction mixture obtainable by oily reacting oxidized coenzyme Q10 with a reducing agent in water, or by distilling off an coexisting organic solvent at or above the melting temperature of reduced coenzyme Q10 in concentrating the organic phase containing reduced coenzyme Q10. Moreover, a solution or slurry of reduced coenzyme Q10 may be obtained by adding a desired solvent to the obtained oily product, or a solid of reduced coenzyme Q10 may be produced by contacting the oily product with a seed crystal.
    Type: Grant
    Filed: July 15, 2002
    Date of Patent: April 24, 2007
    Assignee: Kaneka Corporation
    Inventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
  • Patent number: 7183444
    Abstract: The present invention relates to a method for the preparation of anisalcohol (methoxybenzyl alcohol) by hydrogenation of anisaldehyde (methoxybenzaldehyde) in the presence of Raney nickel and a basic additive, the use of the anisalcohol and hygiene or care products containing anisalcohol.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: February 27, 2007
    Assignee: Symrise GmbH & Co. KG
    Inventors: Walter Kuhn, Hans-Ulrich Funk, Gerhard Senft
  • Patent number: 7119123
    Abstract: Antimicrobially active 4-methyl-4-aryl-2-pentanols of the Formula 1 below, methods for the preparation of these compounds and their use as antimicrobial active compounds are described. Surprisingly, compounds of the Formula 1 for which: R=hydrogen, hydroxyl, alkoxy group with up to 10 C atoms, straight-chain or branched, saturated or unsaturated alkyl with up to 10 C atoms, alkylthioether group with up to 10 C atoms, the alkylthioether group being bonded to the aromatic ring via a thioether bridge, fluorine, chlorine, bromine, iodine, or alkyl with up to 10 C atoms that is interrupted by one or more oxygen and/or sulphur atoms, have proved to be antimicrobially active.
    Type: Grant
    Filed: March 3, 2004
    Date of Patent: October 10, 2006
    Assignee: Symrise GmbH & Co. KG
    Inventors: Gerhard Schmaus, Holger Joppe
  • Patent number: 7115784
    Abstract: The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate.
    Type: Grant
    Filed: January 4, 2005
    Date of Patent: October 3, 2006
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Artis Klapars, Jon C. Antilla, Gabriel E. Job, Martina Wolter, Fuk Y. Kwong, Gero Nordmann, Edward J. Hennessy
  • Patent number: 7034166
    Abstract: A novel process for efficiently and easily producing a compound represented by the formula: wherein ring A is a benzene ring that may be optionally further substituted in addition to the group represented by W, or a salt thereof; which comprises reacting a compound represented by the formula: wherein R1 and R2 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, Y is a halogen atom, ring A is a benzene ring that may be optionally further substituted in addition to the group represented by Y and ring B is an optionally substituted benzene ring, or a salt thereof, with a compound represented by the formula: WH wherein W is wherein ring C is an optionally substituted benzene ring, ring D is an optionally substituted 5- to 7-membered nitrogen-containing heterocyclic ring, R3 is a hydrogen atom, an aliphatic hydrocarbon group containing an aromatic group or an acyl group, and R4 is a hydrogen atom, an optio
    Type: Grant
    Filed: July 11, 2002
    Date of Patent: April 25, 2006
    Assignee: Takeda Pharmaceutical Company Limited
    Inventors: Hiroyuki Tawada, Makoto Yamashita, Yujiro Ono
  • Patent number: 6992226
    Abstract: A process for preparing toluene derivatives of the formula I where R1, R2 and R3 are, independently of one another, hydrogen, alkyl radicals, hydroxyl groups and/or alkoxy groups, comprises reacting the corresponding benzoic acids, benzoic esters or benzoic anhydrides with hydrogen in the presence of a catalyst.
    Type: Grant
    Filed: April 24, 2002
    Date of Patent: January 31, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf-Hartmuth Fischer, Markus Rösch, Norbert Götz
  • Patent number: 6969778
    Abstract: The present invention relates to neolignan (NEOLASA-I) 3-ethyl-2-methyl-3-(2?,4?,5?-trimethoxy-phenyl-1-(2?,4?,5?-trimethoxy)phenyl-1-propene and a process for the preparation of high purity, higher yield neolignan, ?-asarone, 2,4,5-trimethoxy-phenyl propionone from ?-asarone or ?-asarone rich Acorus calamus oil containing ? and ?-asarone by hydrogenating and dimerizing by treatment with DDQ in presence of an organic acid.
    Type: Grant
    Filed: September 12, 2003
    Date of Patent: November 29, 2005
    Assignee: Council of Scientific & Industrial Research
    Inventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Ruchi Acharya
  • Patent number: 6881868
    Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: April 19, 2005
    Assignee: Speedel Pharma AG
    Inventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
  • Patent number: 6867323
    Abstract: Improved methods for generating a —C—C— bond by cross-coupling of a transferable group with an acceptor group. The transferable group is a substituent of an organosilicon nucleophile and the acceptor group is provided as an organic electrophile. The reaction is catalyzed by a Group 10 transition metal complex (e.g., Ni, Pt or Pd), particularly by a palladium complex. Certain methods of this invention use improved organosilicon nucleophiles which are readily prepared, can give high product yields and exhibit high stereoselectivity. Methods of this invention employ activating ions such as halides, hydroxide, hydride and silyloxides. In specific embodiments, organosilicon nucleophilic reagents of this invention include siloxanes, particularly cyclic siloxanes. The combination of the cross-coupling reactions of this invention with ring-closing metathesis, hydrosilylation and intramolecular hydrosilylation reactions provide useful synthetic strategies that have wide application.
    Type: Grant
    Filed: June 6, 2001
    Date of Patent: March 15, 2005
    Assignee: The Board of Trustees of the University of Illinois
    Inventors: Scott E. Denmark, Jun Young Choi, Daniel Wehrli, Zhicai Wu, Luc Neuville, Weitao Pan, Ramzi F. Sweis, Zhigang Wang, Shyh-Ming Yang
  • Patent number: 6852895
    Abstract: The present invention provides a convergent method for the synthesis of ubiquinones and ubiquinone analogues. Also provided are precursors of ubiquinones and their analogues that are useful in the methods of the invention.
    Type: Grant
    Filed: September 27, 2002
    Date of Patent: February 8, 2005
    Assignee: Zymes, Inc.
    Inventors: Bruce H. Lipshutz, Paul Mollard
  • Patent number: 6806395
    Abstract: A process for producing a 3,5-bisalkylphenol (2) according to the following reaction scheme: (wherein R1 represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, or a hydroxyl-protecting group (other than methyl group); R2 represents a C1 to C5 lower alkyl group or an optionally substituted phenyl group; and each of R3 and R4, which may be identical to or different from each other, represents a lower alkyl group, an aralkyl group, or an aryl group); a carbinol compound (1); and a process for producing the carbinol compound. The production process of the present invention enables efficient and safe production of a variety of 3,5-bisalkylphenols including 3,5-diisopropylphenol, which are important as synthesis intermediates for drugs and agricultural chemicals, in shorter steps at high purity in high yield, thus contributing to consistent supply of drugs and agricultural chemicals.
    Type: Grant
    Filed: March 18, 2003
    Date of Patent: October 19, 2004
    Assignee: Kowa Co., Ltd.
    Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
  • Patent number: 6774250
    Abstract: The invention relates to the process for the preparation of liquid reaction products of cycloaliphatic epoxides with mono- or multifunctional hydroxy compounds. The process comprises reacting a polyfunctional cycloaliphatic epoxy resin with a mono- or multifunctional hydroxy compound in the presence of a heterogeneous surface-active catalyst. The invention also relates to curable compositions containing the product obtained by the process.
    Type: Grant
    Filed: August 2, 2002
    Date of Patent: August 10, 2004
    Assignee: Huntsman Advanced Materials Americas Inc.
    Inventors: Kevin B. Hatton, Pauline G. Barker, Claus W. Rabener, Christiane Rabener
  • Patent number: 6689817
    Abstract: The invention pertains to a process for preparing guaifenesin tannate. The process involves the steps of mixing guaifenesin with tannic acid in the presence of water, continuing to mix the reaction mixture for about 5 minutes to about 4 hours and thereafter removing at least about 80 wt.% of the water by freeze-drying the reaction mixture.
    Type: Grant
    Filed: December 14, 2001
    Date of Patent: February 10, 2004
    Assignee: Jame Fine Chemicals, Inc.
    Inventors: Cheng Guo, Vilas M. Chopdekar
  • Patent number: 6620977
    Abstract: A process for preparing a butanetriol derivative of the formula (1) useful as intermediates of medicines wherein R1 is the same defined below, which comprises reacting a compound of the formula (3) wherein R1 and R2 are the different protecting groups, and an ethylene glycol derivative in a basic condition to prepare a compound of the formula (4) or (4a) wherein R1 and R2 are the same defined above, and then subjecting the compound (4) or (4a) to selective deprotection reaction.
    Type: Grant
    Filed: June 9, 2000
    Date of Patent: September 16, 2003
    Assignee: Daiso Co., Ltd.
    Inventors: Makoto Hirata, Masafumi Mikami, Yoshiro Furukawa
  • Patent number: 6617475
    Abstract: Optically active &agr;-hydroxyethers are prepared from prochiral &agr;-ketoethers by heterogeneous hydrogenation using platinum catalysts in the presence of a chiral nitrogen base in high chemical and optical yields, since this type of hydrogenation selectively hydrogenates only one diastereomer virtually to completion. The yields may be substantially increased by adding a solid, strong base which has a racemizing effect on the non-hydrogenatable diasteromer.
    Type: Grant
    Filed: September 4, 2002
    Date of Patent: September 9, 2003
    Assignee: Solvias AG
    Inventors: Martin Studer, Stephan Burkhardt
  • Patent number: 6608232
    Abstract: The invention concerns a method for preparing a benzylic-type ether from an aromatic compound. The inventive method for preparing a benzylic-type ether from an aromatic compound is characterised in that it consists in: in a first step, acylating an aromatic compound by reacting said aromatic compound with an acylating agent, in the presence of an efficient amount of zeolite or a Friedel-Crafts catalyst leading to a ketonic compound; in a second step, reducing the carbonyl group into carbinol leading to a benzylic alcohol; in a third step, etherifying the hydroxyl group, by reacting the benzylic alcohol with another alcohol, in the presence of an efficient amount of zeolite.
    Type: Grant
    Filed: July 3, 2001
    Date of Patent: August 19, 2003
    Inventors: Roland Jacquot, Michel Spagnol
  • Patent number: 6590127
    Abstract: The present invention relates to a process for the preparation of high purity and yield &agr;-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from &bgr;-asarone or &bgr;-asarone rich Acorus calamus oil containing &agr; and &ggr;-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and &agr;-asarone can also be obtained by treating the hydrogenated product of &bgr;-asarone or &bgr;-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: July 8, 2003
    Assignee: Council of Scientific & Industrial Research
    Inventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Ruchi Acharya
  • Publication number: 20030065013
    Abstract: The invention provides sodium channel modulating compounds which are useful for treating diseases or conditions associated with sodium channel activity, such as neuropathic pain. The invention also provides pharmaceutical compositions comprising a compound of the present invention, as well as therapeutic methods comprising administering such a compound or salt to a mammal (e.g. a human).
    Type: Application
    Filed: January 15, 2002
    Publication date: April 3, 2003
    Inventors: Seok-Ki Choi, Paul R. Fatheree, David C. Green, Daniel Marquess
  • Publication number: 20030036666
    Abstract: A method for reducing a malonate having the formula R1R2C(CO2R3)(Co2R4) to a diol having the formula R1R2C(CH2OH)2 comprising treating said malonate with sodium aluminum hydride.
    Type: Application
    Filed: April 25, 2002
    Publication date: February 20, 2003
    Inventors: Won Suh Park, John Hiroshi Yamamoto
  • Patent number: 6512147
    Abstract: A mixed liquid of two or more components different in boiling temperature from each other and soluble in or compatible with each other is evaporated into a mixed vapor having a similar composition to that of the mixed liquid by using an apparatus having a thin film evaporator (1) having a feed inlet (1a) and a delivery outlet (1b), while forcedly circulating the non-evaporated portion of the mixed multi-component liquid by withdrawing the non-evaporated mixed liquid portion from the delivery side end portion of the evaporator and returning the mixed liquid portion into the feed side end portion of the evaporator through a circulating line (3), and the resultant mixed multi-component vapor can be used as a mixed material vapor for a gas phase catalytic reaction for producing, for example, a mono and/or a di-alkylether of an aromatic dihydroxy compound.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: January 28, 2003
    Assignee: UBE Industries, Ltd.
    Inventors: Yukio Inaba, Kazunori Fujita, Hiroshi Kofuji
  • Patent number: 6498278
    Abstract: A method for the preparation of &ggr;-hydroxy ethers from cyclic organic carbonates and active-hydrogen-containing compounds in one form includes the steps of contacting an active-hydrogen-containing compound and a cyclic organic carbonate compound containing a six-membered ring, and a catalyst, running the reaction at a suitable temperature, and isolating the &ggr;-hydroxy ether as a mixture that can be purified or used directly as produced in the reaction.
    Type: Grant
    Filed: September 5, 2001
    Date of Patent: December 24, 2002
    Assignee: Huntsman Petrochemical Corporation
    Inventors: John H. Clements, Howard P. Klein, Edward T. Marquis
  • Patent number: 6448449
    Abstract: A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol, which is a useful intermediate in the synthesis of the widely used antibiotic Levofloxacin is provided. A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-2-trimethylsiloxypropane is also described. The process includes the ring opening of (R)-propylene oxide with 2,3-difluoro-6-nitrophenyl trimethylsilyl ether in the presence of an optically active Co(salen) catalyst. The trimethylsilyl group of the reactant is transferred to the product aryloxy alcohol, which serves to protect the secondary alcohol in situ. Upon isolation, the trimethylsilyl group is removed and the resulting regioisomeric mixture purified to yield the desired (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol in high purity and yield.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: September 10, 2002
    Assignee: Rhodia ChiRex, Inc.
    Inventor: Jay Francis Larrow
  • Patent number: 6403843
    Abstract: The subject of our invention is the process for the preparation of the 1-(3,4-dimethoxyphenyl)ethanol of formula (I), by the reduction of 3,4-dimethoxyacetophenone of formula (II), characterized in that the carbonyl group of the 3,4-dimethoxyacetophenone of formula (II) is reduced by 1 mol of hydrogen under the conditions of catalytic hydrogenation.
    Type: Grant
    Filed: March 29, 2000
    Date of Patent: June 11, 2002
    Assignee: Agro-Chemie
    Inventors: Matyas Aradi, Geza Arvai, Bela Bertok, Zsuzsanna Kuruczne Ribai, Erzsebet Szalay, Istvan Szekely
  • Patent number: 6399837
    Abstract: A method of polymerizing at least one olefin comprising contacting the olefin with a catalyst composition comprising: 1) a procatalyst composition comprising a magnesium and titanium-containing component and an electron donor compound of the structure: wherein R1 is ethoxy, and R2 is an alkoxy group having from one to ten carbon atoms, and R3-R6 are each individually, hydrogen, hydrocarbyl, hydrocarboxy, nitro, a silyl group or a halogen, 2) a cocatalyst and optionally 3) a selectivity control agent.
    Type: Grant
    Filed: June 5, 2000
    Date of Patent: June 4, 2002
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stanley Edward Wilson, Robert Converse Brady, III
  • Patent number: 6384273
    Abstract: The invention concerns a method for orthometalation of a carbocyclic aromatic derivative bearing at least an electron donor group, characterised in that it consists in reacting said carbocyclic aromatic derivative with an efficient amount of at least one alkaline metal in the presence of a compound of formula (I): RX, wherein: R represents a hydrocarbon radical having 1 to 20 carbon atoms which can be a saturated or unsaturated, linear or branched, acyclic aliphatic radical; a saturated or unsaturated, monocyclic or polycyclic cycloaliphatic radical; a saturated or unsaturated, linear or branched aliphatic radical bearing a cyclic substituent; and X represents a bromine or chlorine atom.
    Type: Grant
    Filed: January 24, 2001
    Date of Patent: May 7, 2002
    Assignee: Rhodia Chimie
    Inventors: Virginie Pevere, Jean Roger Desmurs, Charles Mioskowski, Alain Wagner, Arnaud Gissot
  • Patent number: 6355813
    Abstract: Invented is an improved process for preparing aromatic ring-fused cyclopentane derivatives. Preferred compounds prepared by this invention are indane carboxylates and cyclopentanopyridine derivatives. The most preferred compounds prepared by this invention are (+)(1S, 2R, 3S)-3-[2-(2-hydroxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof and (+)(1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof. Also invented are novel intermediates useful in preparing these compounds.
    Type: Grant
    Filed: June 29, 2000
    Date of Patent: March 12, 2002
    Assignee: SmithKline Beecham Corporation
    Inventors: William Morrow Clark, Ivan Lantos, Robert John Mills, Lendon Norwood Pridgen, Ann Marie Tickner
  • Patent number: 6274635
    Abstract: The present invention provides a method, compounds, and compositions for treating a disease associated with immune dysfunction. In accordance with the method, a pharmacologically-acceptable composition including at least one compound selected from the group of compounds consisting of 5-alkyl-resorcinol derivatives, cannabinol derivatives, cannabidiol derivatives, cannabigerol derivatives, and combinations thereof is administered to a patient under conditions sufficient to attenuate the dysfunction within the immune system. The invention also provides an antiviral cannabinol derivative that can be used in the inventive method. The invention also provides an alkylated resorcinol derivative and a method of using the alkylated resorcinol derivative to attenuate the growth of a neoplasm. The method and compound are useful for treating diseases of the immune system, such as HIV disease and neoplastic disorders.
    Type: Grant
    Filed: March 22, 2000
    Date of Patent: August 14, 2001
    Assignee: Immugen Pharmaceuticals Inc.
    Inventor: Craig A. Travis
  • Publication number: 20010009770
    Abstract: A propargylic alcohol, enriched in the (R)-enantiomer, has the formula 1
    Type: Application
    Filed: February 2, 2001
    Publication date: July 26, 2001
    Inventors: Martin Edward Fox, Julian Simon Parratt
  • Publication number: 20010004670
    Abstract: A process for condensing at least one carbonyl compound carrying at least one electron-withdrawing group with an aromatic derivative carrying at least one hydroxyl functional group, wherein the electron-withdrawing group present on the carbonyl compound is selected from fluoroalkyl derivatives, esters, including orthoesters, and nitrites and said condensation is carried out in a basic medium.
    Type: Application
    Filed: November 29, 2000
    Publication date: June 21, 2001
    Inventors: Roland Jacquot, Michel Spagnol
  • Patent number: 6229054
    Abstract: The present invention comprises a process for the hydroxyalkylation of cardanol with cyclic organic carbonates in the presence of organic or inorganic catalysts and a novel composition of matter produced by that process. The unique molecular structure of cardanol allows the use of a variety of organic or inorganic basic catalysts, including triethylamine, imidazol, sodium hydroxide and sodium carbonate, in the hydroxyalkylation reaction without forming quantities of undesirable side-products. According to this invention, the final product, monohydroxyalkylcardanyl ether, can be obtained with high yield and high purity. The product has a light color and its color stability is enhanced by replacing the phenol's hydroxyl group with a more stable hydroxyalkoxyl group.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: May 8, 2001
    Assignee: Cardolite Corporation
    Inventors: Zhisheng Dai, Meng J. Chen
  • Patent number: 6218581
    Abstract: The present invention relates to a process of producing optically active alcohol having high optical purity by performing an enzyme conversion reaction on a raw material serving as the substrate, examples of which include racemic alcohol, ketone and the acylated form of a racemic alcohol, followed by hydrolysis as necessary, using as an optical separation catalyst a immobilized water-soluble protein extracted from inexpensive and safe grains or beans in order to solve the problems of the reaction process consisting of low yield due to the occurrence of side reactions, detrimental effects on the ecosystem and their accompanying cost burden, the need for aseptic procedures and the extended amount of time of subculturing, all of which are problems associated with production processes of optically active alcohols of the prior art that use microorganisms, microorganism enzymes, animal tissue enzymes and cultured plant cells.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: April 17, 2001
    Assignee: Sanyo Shokuhin Co., Ltd.
    Inventor: Hiroyuki Nagaoka
  • Patent number: 6172268
    Abstract: A method for producing an optically active 1-substituted 2-propanol of the following formula 1, which comprises reacting a hydroxy aromatic compound of the following formula 2 with an optically active propylene oxide in the presence of a catalyst: AOH  Formula 2 CH3C*H(OH)CH2OA  Formula 1 wherein A is a univalent aromatic group, and C* is an asymmetric carbon atom.
    Type: Grant
    Filed: January 28, 2000
    Date of Patent: January 9, 2001
    Assignee: Asahi Glass Company, Limited
    Inventors: Toshihiko Tohma, Tomoyuki Asai
  • Patent number: 6140274
    Abstract: Dihalopropene compounds of the general formula: ##STR1## wherein R.sup.1 is substituted alkyl; R.sup.2, R.sup.3 and R.sup.4 are each independently halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro or cyano; A is O, S(O).sub.t or NR.sup.14 in which R.sup.14 is H or alkyl and t is 0 to 2; B is substituted alkylene, alkenylene or alkynylene; r is 0 to 2; X's are each independently halogen; Y is O, S or NH; Z is O, S or NR.sup.25 in which R.sup.25 is H, acetyl or alkyl, which are useful as active ingredients of insecticidal/acaricidal agents.
    Type: Grant
    Filed: June 12, 1998
    Date of Patent: October 31, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Ikegami, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Hirotaka Takano
  • Patent number: 6130346
    Abstract: A process for preparing an organic compound, comprising conducting an organic reaction in the presence of a phosphine oxide represented by formula (1); ##STR1## where R.sup.1 is the same or different and each represents a hydrogen or hydrocarbon group with 1 to 10 carbon atoms, and x is the amount of water as a molar ratio which is 0 to 5.0, exhibiting a high catalytic performance especially in an organic reaction involving an alkylene oxide.
    Type: Grant
    Filed: April 13, 1999
    Date of Patent: October 10, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tadahito Nobori, Takaomi Hayashi, Isao Hara, Shinji Kiyono, Atsushi Shibahara, Katsuhiko Funaki, Tatsuhiro Urakami, Keisuke Takuma, Usaji Takaki
  • Patent number: 6124474
    Abstract: A process for preparing chiral isomers of N-protected 2-azetidinemethanol compounds, particularly N-(phenylmethyl)-2-azetidinemethanol and N-BOC-2-azetidinemethanol, and especially the (R)-isomers thereof, as well as O-substituted derivatives thereof.
    Type: Grant
    Filed: December 21, 1999
    Date of Patent: September 26, 2000
    Assignee: Abbott Laboratories
    Inventors: Anthony R. Haight, John E. Lallaman, Gregory S. Wayne
  • Patent number: 6124507
    Abstract: Novel compositions of the structure ##STR1## wherein R.sup.1 and R.sup.2 are each an alkoxy group which may be the same or different and have from one to ten carbon atoms, and R.sup.3 -R.sup.6 are each individually, hydrogen, hydrocarbyl, hydrocarboxy, nitro, a silyl group or a halogen, with the provisos that if either R.sup.1 or R.sup.2 are methoxy, then at least one of R.sup.3 -R.sup.6 is not hydrogen, if R.sup.1 and R.sup.2 are both ethoxy, then at least one of R.sup.3 -R.sup.6 is not hydrogen, and R.sup.1 and R.sup.2 cannot both be methoxy, are taught herein, which may be used as electron donors, either internal or external, for catalysts used in the polymerization of olefins.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: September 26, 2000
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stanley Edward Wilson, Robert Converse Brady, III
  • Patent number: 5922903
    Abstract: An arrangement for a falling film type reactor uses corrugated plates to improve the distribution and dispersion of the gaseous reactant into the liquid. Corrugated plates introduce increased turbulence for promoting better distribution and dispersion of the gas. Corrugation angles can be varied to suit the fluid flow properties of the liquid reactant. The reactor arrangement can also include heat transfer channels defined by the corrugated plates in an alternate arrangement of heat transfer channels and gas liquid contacting channels. The corrugations may also be varied to suit the particular heat transfer requirements of the reactions. The corrugated plates are spaced apart in the contacting channels to prevent localized film contact and placed in contact in the heat exchange portion to stabilize the plate elements defining the corrugations.
    Type: Grant
    Filed: November 10, 1997
    Date of Patent: July 13, 1999
    Assignee: UOP LLC
    Inventor: Peter R. Pujado
  • Patent number: 5874460
    Abstract: Compounds of the formula ##STR1## where W is (CH.sub.2).sub.n where n is 1 or 2, or n is 0 and W represents lower alkyl groups attached to each oxygen;m is an integer between 1 and 8;R.sub.1 is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.4, CONR.sub.5 R.sub.6, CONR.sub.5 SO.sub.2 R.sub.7, CH.sub.2 OH, CH.sub.2 OR.sub.7, CH.sub.2 O--COR.sub.7, CH.sub.2 O--CONR.sub.5,R.sub.7, CH.sub.2 OCOOR.sub.7, CH.sub.2 NH.sub.2, CH.sub.2 NR.sub.5 R.sub.6, etc. where R.sub.4 is an alkyl group, or a cycloalkyl group, or R.sub.4 is phenyl or lower alkylphenyl, R.sub.5 and R.sub.6 independently are hydrogen, an alkyl group, etc., R.sub.7 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.8 is lower alkyl, and R.sub.9 is divalent alkyl radical of 2-5 carbons, R.sub.10 is an alkyl OR cycloalkyl containing 1 to 5 carbons;R.sub.2 is H, COR.sub.7, R.sub.7, CO--OR.sub.7, CO--NR.sub.5,R.sub.7, PO(OH)OR.sub.7, PO(OR.sub.7).sub.2, POR.sub.7 OH, or POR.sub.7 (OR.sub.7) ;R.sub.
    Type: Grant
    Filed: June 9, 1998
    Date of Patent: February 23, 1999
    Assignee: Allergan Sales Inc.
    Inventors: Robert M. Burk, David F. Woodward
  • Patent number: 5844056
    Abstract: The synthesis and characterization of novel linear polymers and multi-arm star polymers comprising polyisobutylene arms connected to a well-defined calixarene core are described. The polymers are directly telechelic. They synthesis has been achieved using the "core first" method wherein multifunctional calix?n!arene (where n=4 to 16) derivatives or their monofunctional analogues are used as initiators which, in conjunction with certain Freidel-Crafts acids as co-initiators, induce the living polymerization of isobutylene or a similar carbocationic polymerizable monomer. Novel initiators suitable for inducing the polymerization are also described.
    Type: Grant
    Filed: August 7, 1996
    Date of Patent: December 1, 1998
    Assignee: The University of Akron
    Inventors: Joseph P. Kennedy, Istvan J. Majoros, Sunny Jacob
  • Patent number: 5840997
    Abstract: Alkoxybenzaldehydes and aryloxybenzaldehydes are converted to the corresponding phenols by reacting the benzaldehydes in an organic solvent phase with formic acid and hydrogen peroxide in an aqueous solvent phase to produce the corresponding formate ester. The formate ester is then saponified to produce the corresponding phenol.
    Type: Grant
    Filed: March 31, 1997
    Date of Patent: November 24, 1998
    Assignee: Dakota Gasification Company
    Inventors: Paul D. Pansegrau, Brant P. Munson
  • Patent number: 5698727
    Abstract: A chemiluminescent 1,2-dioxetane derivative having a formula (I): ##STR1## wherein R.sup.1 and R.sup.4 each represent, individually, hydrogen, an alkyl group, an alkoxyl group, a hydroxyl group, or --OSi(R.sup.9 R.sup.10 R.sup.11) in which R.sup.9, R.sup.10 and R.sup.11 each represent an alkyl group; R.sup.2, R.sup.3, R.sup.5 and R.sup.6 each represent, individually, hydrogen or an alkyl group, provided that R.sup.2, R.sup.3, R.sup.5 and R.sup.6 each cannot be hydrogen at the same time, and that R.sup.2 and R.sup.3, and R.sup.5 and R.sup.6, each taken together, can form a cycloalkyl group; R.sup.7 represents an alkyl group; R.sup.8 represents hydrogen, an alkoxyl group, a phosphate salt group, or --OSi(R.sup.9 R.sup.10 R.sup.11); intermediates for synthesizing the above 1,2-dioxetane derivative; and methods of producing the intermediates are provided.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 16, 1997
    Inventor: Masakatsu Matsumoto
  • Patent number: 5679871
    Abstract: A process for the production of hydroxyalkylated phenolic or hydroxyalkylated thiophenolic compounds is disclosed. The process comprises providing a phenolic or thiophenolic compound, a cyclic organic carbonate compound, and a catalyst selected from the group consisting of an alkali metal, an alcohol-derived salt of the alkali metal, and mixtures thereof; and reacting the phenolic compound and the cyclic organic carbonate compound in the presence of the catalyst to form the hydroxyalkylated phenolic or hydroxyalkylated thiophenolic compound. Preferably, the alkali metal is selected from sodium, potassium, or lithium.
    Type: Grant
    Filed: September 26, 1996
    Date of Patent: October 21, 1997
    Assignee: Reichhold Chemicals, Inc.
    Inventor: Hildeberto Nava
  • Patent number: 5621133
    Abstract: Novel compounds having the formula ##STR1## and the pharmaceutically acceptable salts, esters and amides thereof, whereinA is --O--, --S-- or --CR.sup.2 R.sup.8 --;R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, X and Y are specifically defined; andup to one combination of (a) R.sup.2 and R.sup.5, (b) R.sup.5 and R.sup.6, (c) R.sup.5 and R.sup.7, (d) R.sup.6 and R.sup.7, and (e) R.sup.7 and Y, taken together with the atoms to which they are attached, may form a ring, the compounds being useful for treating dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of cognitive impairment, attention deficit disorder, and substance abuse and other addictive behavior disorders.Also disclosed are intermediates and processes useful in the preparation of the above compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 15, 1997
    Inventors: Michael P. DeNinno, Richard J. Perner
  • Patent number: 5608104
    Abstract: Described is a detection method of a pyrethroid compound which comprises providing a first antibody against the pyrethroid compound, said first antibody having been obtained by immunizing a responder with an immunogen which is a first conjugate between a first carrier and a first haptenic compound represented by the following formula (1) or (2): ##STR1## mixing the first antibody with the sample solution, causing any unreacted portion of the first antibody to be bound on a second conjugate as a coated antigen, said second conjugate being formed of a second carrier and a second haptenic compound and having been coated on a surface of a solid phase carrier, whereby an antigen-antibody conjugate is obtained; andreacting the antigen-antibody conjugate with a second antibody against the first antibody, said second antibody having a labelled enzyme linked therewith.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: March 4, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Hideo Ohkawa, Koji Kitajima, Kenji Kodaka, Yasunori Fumoto, Takako Kumeta
  • Patent number: 5583230
    Abstract: A novel mildew resistant polymerizable compound of the formula: ##STR1## wherein X is --0-- or --S--; and Y is a residue of a known mildew proofing compound, preferably, a residue of a compound selected from the group consisting of phenol substituted with 1 to 5 halogen atoms, p-chloro-m-cresol, o-phenylphenol, p-chloro-m-xylenol, salicylanilide, 8-hydroxyquinoline, 2-(4'-thiazolyl)benzimidazole, 2,5-dibromo-4-methylaniline, 1,2-benzoisothiazolin-3-one and 2-pyridinethiol-1-oxide. A polymer of the compound [I] and polyurethane composition containing the polymer are also disclosed.
    Type: Grant
    Filed: July 7, 1993
    Date of Patent: December 10, 1996
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Hideyuki Mitamura, Yoshikazu Arimatsu