Polyoxy Patents (Class 568/648)
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Publication number: 20090036542Abstract: 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: ApplicationFiled: February 23, 2006Publication date: February 5, 2009Inventors: Bang Luu, Dominique Bagnard, Mazen Hanbali, Masashi Yamada, Hiroto Suzuki
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Publication number: 20080228010Abstract: 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: ApplicationFiled: October 30, 2007Publication date: September 18, 2008Inventors: Shenghong A. Dai, Hsing-Yo Lin, Chien-Sheng Wen
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Patent number: 7422702Abstract: 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: GrantFiled: March 22, 2004Date of Patent: September 9, 2008Assignee: Nippon Chemical Industrial Co., Ltd.Inventor: Yuichiro Haramoto
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Patent number: 7393465Abstract: 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: GrantFiled: February 24, 2005Date of Patent: July 1, 2008Assignee: Bayer MaterialScience AGInventors: Meike Niesten, Jack Reese, Joachim Simon, Gerhard Ruttmann
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Patent number: 7230141Abstract: 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: GrantFiled: January 20, 2003Date of Patent: June 12, 2007Assignee: BASF AktiengesellschaftInventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
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Patent number: 7208639Abstract: 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: GrantFiled: July 15, 2002Date of Patent: April 24, 2007Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
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Patent number: 7183444Abstract: 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: GrantFiled: April 9, 2003Date of Patent: February 27, 2007Assignee: Symrise GmbH & Co. KGInventors: Walter Kuhn, Hans-Ulrich Funk, Gerhard Senft
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Patent number: 7119123Abstract: 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: GrantFiled: March 3, 2004Date of Patent: October 10, 2006Assignee: Symrise GmbH & Co. KGInventors: Gerhard Schmaus, Holger Joppe
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Patent number: 7115784Abstract: 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: GrantFiled: January 4, 2005Date of Patent: October 3, 2006Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Artis Klapars, Jon C. Antilla, Gabriel E. Job, Martina Wolter, Fuk Y. Kwong, Gero Nordmann, Edward J. Hennessy
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Patent number: 7034166Abstract: 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 optioType: GrantFiled: July 11, 2002Date of Patent: April 25, 2006Assignee: Takeda Pharmaceutical Company LimitedInventors: Hiroyuki Tawada, Makoto Yamashita, Yujiro Ono
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Patent number: 6992226Abstract: 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: GrantFiled: April 24, 2002Date of Patent: January 31, 2006Assignee: BASF AktiengesellschaftInventors: Rolf-Hartmuth Fischer, Markus Rösch, Norbert Götz
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Patent number: 6969778Abstract: 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: GrantFiled: September 12, 2003Date of Patent: November 29, 2005Assignee: Council of Scientific & Industrial ResearchInventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Ruchi Acharya
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Patent number: 6881868Abstract: 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: GrantFiled: June 26, 2001Date of Patent: April 19, 2005Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
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Patent number: 6867323Abstract: 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: GrantFiled: June 6, 2001Date of Patent: March 15, 2005Assignee: The Board of Trustees of the University of IllinoisInventors: Scott E. Denmark, Jun Young Choi, Daniel Wehrli, Zhicai Wu, Luc Neuville, Weitao Pan, Ramzi F. Sweis, Zhigang Wang, Shyh-Ming Yang
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Patent number: 6852895Abstract: 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: GrantFiled: September 27, 2002Date of Patent: February 8, 2005Assignee: Zymes, Inc.Inventors: Bruce H. Lipshutz, Paul Mollard
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Patent number: 6806395Abstract: 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: GrantFiled: March 18, 2003Date of Patent: October 19, 2004Assignee: Kowa Co., Ltd.Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
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Patent number: 6774250Abstract: 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: GrantFiled: August 2, 2002Date of Patent: August 10, 2004Assignee: Huntsman Advanced Materials Americas Inc.Inventors: Kevin B. Hatton, Pauline G. Barker, Claus W. Rabener, Christiane Rabener
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Patent number: 6689817Abstract: 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: GrantFiled: December 14, 2001Date of Patent: February 10, 2004Assignee: Jame Fine Chemicals, Inc.Inventors: Cheng Guo, Vilas M. Chopdekar
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Patent number: 6620977Abstract: 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: GrantFiled: June 9, 2000Date of Patent: September 16, 2003Assignee: Daiso Co., Ltd.Inventors: Makoto Hirata, Masafumi Mikami, Yoshiro Furukawa
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Patent number: 6617475Abstract: 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: GrantFiled: September 4, 2002Date of Patent: September 9, 2003Assignee: Solvias AGInventors: Martin Studer, Stephan Burkhardt
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Patent number: 6608232Abstract: 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: GrantFiled: July 3, 2001Date of Patent: August 19, 2003Inventors: Roland Jacquot, Michel Spagnol
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Patent number: 6590127Abstract: 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: GrantFiled: March 28, 2002Date of Patent: July 8, 2003Assignee: Council of Scientific & Industrial ResearchInventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Ruchi Acharya
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Publication number: 20030065013Abstract: 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: ApplicationFiled: January 15, 2002Publication date: April 3, 2003Inventors: Seok-Ki Choi, Paul R. Fatheree, David C. Green, Daniel Marquess
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Publication number: 20030036666Abstract: 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: ApplicationFiled: April 25, 2002Publication date: February 20, 2003Inventors: Won Suh Park, John Hiroshi Yamamoto
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Patent number: 6512147Abstract: 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: GrantFiled: March 28, 2002Date of Patent: January 28, 2003Assignee: UBE Industries, Ltd.Inventors: Yukio Inaba, Kazunori Fujita, Hiroshi Kofuji
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Patent number: 6498278Abstract: 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: GrantFiled: September 5, 2001Date of Patent: December 24, 2002Assignee: Huntsman Petrochemical CorporationInventors: John H. Clements, Howard P. Klein, Edward T. Marquis
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Patent number: 6448449Abstract: 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: GrantFiled: April 20, 2001Date of Patent: September 10, 2002Assignee: Rhodia ChiRex, Inc.Inventor: Jay Francis Larrow
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Patent number: 6403843Abstract: 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: GrantFiled: March 29, 2000Date of Patent: June 11, 2002Assignee: Agro-ChemieInventors: Matyas Aradi, Geza Arvai, Bela Bertok, Zsuzsanna Kuruczne Ribai, Erzsebet Szalay, Istvan Szekely
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Patent number: 6399837Abstract: 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: GrantFiled: June 5, 2000Date of Patent: June 4, 2002Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stanley Edward Wilson, Robert Converse Brady, III
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Patent number: 6384273Abstract: 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: GrantFiled: January 24, 2001Date of Patent: May 7, 2002Assignee: Rhodia ChimieInventors: Virginie Pevere, Jean Roger Desmurs, Charles Mioskowski, Alain Wagner, Arnaud Gissot
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Patent number: 6355813Abstract: 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: GrantFiled: June 29, 2000Date of Patent: March 12, 2002Assignee: SmithKline Beecham CorporationInventors: William Morrow Clark, Ivan Lantos, Robert John Mills, Lendon Norwood Pridgen, Ann Marie Tickner
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Patent number: 6274635Abstract: 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: GrantFiled: March 22, 2000Date of Patent: August 14, 2001Assignee: Immugen Pharmaceuticals Inc.Inventor: Craig A. Travis
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Publication number: 20010009770Abstract: A propargylic alcohol, enriched in the (R)-enantiomer, has the formula 1Type: ApplicationFiled: February 2, 2001Publication date: July 26, 2001Inventors: Martin Edward Fox, Julian Simon Parratt
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Publication number: 20010004670Abstract: 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: ApplicationFiled: November 29, 2000Publication date: June 21, 2001Inventors: Roland Jacquot, Michel Spagnol
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Patent number: 6229054Abstract: 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: GrantFiled: December 9, 1999Date of Patent: May 8, 2001Assignee: Cardolite CorporationInventors: Zhisheng Dai, Meng J. Chen
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Patent number: 6218581Abstract: 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: GrantFiled: August 6, 1999Date of Patent: April 17, 2001Assignee: Sanyo Shokuhin Co., Ltd.Inventor: Hiroyuki Nagaoka
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Patent number: 6172268Abstract: 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: GrantFiled: January 28, 2000Date of Patent: January 9, 2001Assignee: Asahi Glass Company, LimitedInventors: Toshihiko Tohma, Tomoyuki Asai
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Dihalopropene compounds, their use as insecticides/acaricides and intermediates for their production
Patent number: 6140274Abstract: 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: GrantFiled: June 12, 1998Date of Patent: October 31, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Ikegami, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Hirotaka Takano -
Patent number: 6130346Abstract: 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: GrantFiled: April 13, 1999Date of Patent: October 10, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Tadahito Nobori, Takaomi Hayashi, Isao Hara, Shinji Kiyono, Atsushi Shibahara, Katsuhiko Funaki, Tatsuhiro Urakami, Keisuke Takuma, Usaji Takaki
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Patent number: 6124474Abstract: 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: GrantFiled: December 21, 1999Date of Patent: September 26, 2000Assignee: Abbott LaboratoriesInventors: Anthony R. Haight, John E. Lallaman, Gregory S. Wayne
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Patent number: 6124507Abstract: 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: GrantFiled: December 10, 1997Date of Patent: September 26, 2000Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stanley Edward Wilson, Robert Converse Brady, III
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Patent number: 5922903Abstract: 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: GrantFiled: November 10, 1997Date of Patent: July 13, 1999Assignee: UOP LLCInventor: Peter R. Pujado
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Patent number: 5874460Abstract: 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: GrantFiled: June 9, 1998Date of Patent: February 23, 1999Assignee: Allergan Sales Inc.Inventors: Robert M. Burk, David F. Woodward
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Patent number: 5844056Abstract: 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: GrantFiled: August 7, 1996Date of Patent: December 1, 1998Assignee: The University of AkronInventors: Joseph P. Kennedy, Istvan J. Majoros, Sunny Jacob
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Patent number: 5840997Abstract: 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: GrantFiled: March 31, 1997Date of Patent: November 24, 1998Assignee: Dakota Gasification CompanyInventors: Paul D. Pansegrau, Brant P. Munson
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Patent number: 5698727Abstract: 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: GrantFiled: June 6, 1995Date of Patent: December 16, 1997Inventor: Masakatsu Matsumoto
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Patent number: 5679871Abstract: 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: GrantFiled: September 26, 1996Date of Patent: October 21, 1997Assignee: Reichhold Chemicals, Inc.Inventor: Hildeberto Nava
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Patent number: 5621133Abstract: 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: GrantFiled: June 5, 1995Date of Patent: April 15, 1997Inventors: Michael P. DeNinno, Richard J. Perner
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Patent number: 5608104Abstract: 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: GrantFiled: September 27, 1994Date of Patent: March 4, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Hideo Ohkawa, Koji Kitajima, Kenji Kodaka, Yasunori Fumoto, Takako Kumeta
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Patent number: 5583230Abstract: 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: GrantFiled: July 7, 1993Date of Patent: December 10, 1996Assignee: Toyo Boseki Kabushiki KaishaInventors: Hideyuki Mitamura, Yoshikazu Arimatsu