Unsaturation In The Ring Patents (Class 568/823)
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Patent number: 8716535Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: October 16, 2008Date of Patent: May 6, 2014Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 8716534Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: October 16, 2008Date of Patent: May 6, 2014Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 8614345Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts, or pre-catalysts, in hydrogenation processes for the reduction of ketones and/or aldehydes into the corresponding alcohol respectively. Said catalysts are ruthenium complexes comprising a tetradentate ligand (L4) coordinating the ruthenium with: —two nitrogen atoms, each in the form of a primary or secondary amine (i.e. a NH2 or NH group) or N-alkyl imine functional groups (i.e. a C?N group), and —two sulfur atoms, each in the form of thioether functional groups.Type: GrantFiled: December 19, 2011Date of Patent: December 24, 2013Assignee: Firmenich SAInventors: Francesco Santoro, Lionel Saudan, Michel Alfred Joseph Saudan, Sylvia Joyeuse Adélaïde Ada Saudan
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Patent number: 8278332Abstract: The photostabilizing electronic excited state energy—particularly singlet state energy from retinoid compounds—has been found to be readily transferred to (accepted by) ?-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, preferably C1-C8, more preferably methoxy, and the non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, preferably C2-C20. The alkoxycrylene compounds of formula (I) significantly increase the photostability of retinoid compounds in a composition by at least 3-fold.Type: GrantFiled: October 27, 2011Date of Patent: October 2, 2012Assignee: Hallstar Innovations Corp.Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
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Patent number: 8263051Abstract: The photostabilizing electronic excited state energy—particularly singlet state energy from resveratrol compounds—has been found to be readily transferred to (accepted by) ?-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, preferably C1-C8, more preferably methoxy, and the non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, preferably C2-C20. The alkoxycrylene compounds of formula (I) significantly increase the photostability of resveratrol compounds in a composition by at least 3-fold and as much as 10-fold or greater. The ability of the alkoxycrylene compounds to stabilize the resveratrol compound is concentration dependent, with the amount of resveratrol photostabilization increasing with the concentration of the alkoxycrylene compound.Type: GrantFiled: April 5, 2011Date of Patent: September 11, 2012Assignee: Hallstar Innovations Corp.Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
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Patent number: 8133477Abstract: A composition comprising an inorganic particulate material in an amount of about 20 wt % to about 70 wt %, a carrier for the particulate material comprising a compound of formula (I) in an amount of about 1 wt % to about 70 wt %, a particulate material coating material in an amount of about 0 wt % to about 5 wt %, and a dispersing agent for the particulate material in an amount of about 0 wt % to about 5 wt %, based on the total weight of the composition, wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, and the non-alkoxy R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical.Type: GrantFiled: September 4, 2009Date of Patent: March 13, 2012Assignee: Hallstar Innovations Corp.Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
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Patent number: 8115036Abstract: The present invention relates to a fluorine-containing cyclic compound of formula (5): wherein R2-R4 and R9-R15 are independently a hydrogen atom, a halogen atom, or a C1-C25 straight-chain, branched or cyclic alkyl group, and may contain fluorine atom, oxygen atom, sulfur atom, or nitrogen atom. R10 and R11, R12 and R13, or R14 and R15 may be bonded together to form a ring. In such a case, it is a C1-C25 alkylene group that may contain a hetero atom such as oxygen, sulfur and nitrogen, “a” is 0 or 1, “b” is an integer of 0-2 and “c” is an integer of 0-2.Type: GrantFiled: April 22, 2010Date of Patent: February 14, 2012Assignee: Central Glass Company, LimitedInventors: Haruhiko Komoriya, Shinichi Sumida, Michitaka Ootani, Takeo Komata, Kazuhiko Maeda
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Patent number: 8070989Abstract: The photostabilizing electronic excited state energy—particularly singlet state energy from retinoid compounds—has been found to be readily transferred to (accepted by) ?-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, preferably C1-C8, more preferably methoxy, and the non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, preferably C2-C20. The alkoxycrylene compounds of formula (I) significantly increase the photostability of retinoid compounds in a composition by at least 3-fold and as much as 10-fold or greater. The ability of the alkoxycrylene compounds to stabilize the retinoid compound is concentration dependent, with the amount of retinoid photostabilization increasing with the concentration of the alkoxycrylene compound.Type: GrantFiled: July 31, 2009Date of Patent: December 6, 2011Assignee: Hallstar Innovations Corp.Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
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Patent number: 8063254Abstract: The present invention aims to provide reduced coenzyme Q10, which is useful as food, food with nutrient function claims, food for specified health use, nutritional supplement, nutritional product, animal drug, drink, feed, cosmetic, pharmaceutical product, therapeutic drug, prophylactic drug and the like, and a production method of reduced coenzyme Q10. The present invention provides a production method of reduced coenzyme Q10, which includes reducing oxidized coenzyme Q10 with ascorbic acid or its analogue(s) as a reducing agent in a water-containing organic solvent at not more than pH 5. Using the method, the reaction time can be drastically shortened even without adding a basic substance and the like, and unpreferable side reactions can be minimized. Therefore, reduced coenzyme Q10 with high quality can be produced.Type: GrantFiled: October 29, 2008Date of Patent: November 22, 2011Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura
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Patent number: 7902393Abstract: The present invention concerns a process for the preparation of a compound of formula (I) wherein R represents a Me or Et group, as well said compound in the form of any one of its stereoisomers or mixture thereof. The invention concerns also the use of compound (I) for the synthesis of ?-santalol or of derivatives thereof.Type: GrantFiled: May 18, 2009Date of Patent: March 8, 2011Assignee: Firmenich SAInventors: Charles Fehr, Magali Vuagnoux
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Patent number: 7875751Abstract: A novel process for the preparation of highly purified carotenoids from plant extracts, especially the marigold flower extracts, is disclosed. The process includes the formation, isolation and purification of carotenoids, primarily lutein and zeaxanthin, at lower temperatures with the use of at least a polar solvent and at least a non-polar solvent. The highly purified carotenoids so obtained are useful for human consumption, such as nutritional supplements and pharmaceuticals.Type: GrantFiled: November 7, 2008Date of Patent: January 25, 2011Assignee: Allied Biotech CorporationInventors: Chia-Line Chuang, Hsin-Ke Li, Chong-Nan Chuang
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Patent number: 7767866Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: March 12, 2009Date of Patent: August 3, 2010Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Publication number: 20090324570Abstract: The photostabilizing electronic excited state energy—particularly singlet state energy from retinoid compounds—has been found to be readily transferred to (accepted by) ?-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, preferably C1-C8, more preferably methoxy, and the non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, preferably C2-C20. The alkoxycrylene compounds of formula (I) significantly increase the photostability of retinoid compounds in a composition by at least 3-fold and as much as 10-fold or greater. The ability of the alkoxycrylene compounds to stabilize the retinoid compound is concentration dependent, with the amount of retinoid photostabilization increasing with the concentration of the alkoxycrylene compound.Type: ApplicationFiled: July 31, 2009Publication date: December 31, 2009Applicant: HALLSTAR INNOVATIONS CORP.Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
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Patent number: 7550417Abstract: The use as fragrance ingredient of a compound of formula (I) wherein R1 and Y have the same meaning as given in the description, and fragrance applications comprising them.Type: GrantFiled: September 8, 2006Date of Patent: June 23, 2009Assignee: Givandan SAInventors: Jerzy A. Bajgrowicz, Iris Frank
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Patent number: 7521582Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: August 24, 2007Date of Patent: April 21, 2009Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 7495135Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: December 4, 2003Date of Patent: February 24, 2009Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 7442828Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: August 24, 2007Date of Patent: October 28, 2008Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 7323607Abstract: A process for preparing (+)-p-mentha-2,8-diene-1-ol comprising reacting (+)-limonene oxide with at least one amine in the presence of at least one Lewis acid to form amine adduct intermediates. The amine adduct is then oxidized to form an N-oxide that is pyrolized to form (+)-p-mentha-2,8-diene-1-ol.Type: GrantFiled: April 14, 2004Date of Patent: January 29, 2008Assignee: Mallinckrodt Inc.Inventors: Hong Gu, J. Kendall Killgore, John R. Duchek
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Patent number: 7153979Abstract: A triterpene derivative useful for the treatment of hepatic disorders is disclosed. This compound comprises as an active ingredient a triterpene derivative represented by the following formula (I) or a salt thereof: wherein R1 represents a hydroxyl group, arylmethyloxy, lower alkoxy, or lower alkanoyloxy, R2 represents lower alkyl, lower alkenyl, —CH2OR5, formyl, —COOR6, or —CH2N(R7)R8, or R1 and R2 may combine with each other to form —O—C(R9)R10—O—CH2—, R3 and R4, which may be the same or different, represent a hydrogen atom, a hydroxyl group, lower alkyl, lower alkenyl, aryl, hydroxymethyl, —N(R11)R12, formyl, —COOR6, or —OR13, or R3 and R4 may combine with each other to form oxo, hydroxyimino, or alkylidene and X represents O, CH2, or NH.Type: GrantFiled: February 24, 2003Date of Patent: December 26, 2006Assignee: Meiji Seika Kaisha, Ltd.Inventors: Kazue Sasaki, Nobuto Minowa, Shoji Nishiyama, Hiroyuki Kuzuhara
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Patent number: 7145044Abstract: The present invention relates to a method of conveniently and efficiently producing reduced coenzyme Q10 having excellent qualities which is useful in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, drinks, feeds, animal drugs, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. In a method of synthesizing reduced coenzyme Q10 by reducing oxidized coenzyme Q10, followed by crystallization, at least one species selected from among hydrocarbons, fatty acid esters, ethers and nitrites is used as a solvent. Thus, the reduced coenzyme Q10 can be protected from oxidation, and as a result, the formation of the oxidized coenzyme Q10 as a by-product can be minimized, thereby giving reduced coenzyme Q10 having excellent qualities.Type: GrantFiled: July 15, 2002Date of Patent: December 5, 2006Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
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Patent number: 7132391Abstract: An alkyl gycol ether having the following formula wherein R is a C1–C7 saturated, unsaturated, straight-chain or branched, acyclic or cyclic alkyl group, is useful as a fragrance material in perfumes, cosmetics, consumer products, and the like. When R is a saturated, straight-chain or branched, acyclic or cyclic alkyl group, these compounds are especially stable when used as fragrance materials in bleach containing products.Type: GrantFiled: July 10, 2002Date of Patent: November 7, 2006Assignee: Takasago International CorporationInventors: Takashi Aida, Andrew T. Lupo, Hiroyuki Matsuda
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Patent number: 7105709Abstract: The present invention relates to a method of conveniently and efficiently producing high-quality reduced coenzyme Q10 which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof. A method of producing a reduced coenzyme Q10 which comprises reducing an oxidized coenzyme Q10 in an aqueous medium with the use of dithionous acid or a salt thereof, said reduction being carried out in the coexistence of a salt and/or under deoxygenated atmosphere, and at pH of 7 or below. Thus, the formation of the oxidized coenzyme Q10 as a by-product due to oxidation can be minimized, thereby giving reduced coenzyme Q10 having excellent qualities in a high yield.Type: GrantFiled: July 15, 2002Date of Patent: September 12, 2006Assignee: Kaneka CorporationInventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
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Patent number: 7078570Abstract: The present invention relates to substituted cyclohexenes, to their use as well as to their preparation method. These compounds have powerful long lasting natural fruity grapefruit notes with minty and fresh green tonalities.Type: GrantFiled: December 3, 2001Date of Patent: July 18, 2006Assignee: Givaudan SAInventor: Andreas Goeke
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Patent number: 7012161Abstract: There is disclosed a fluorine-containing polymerizable cyclic olefin compound that has one or more partial structures represented by the following general formula (1) or (2).Type: GrantFiled: August 16, 2004Date of Patent: March 14, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Takeshi Kinsho, Yuji Harada
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Patent number: 6951964Abstract: The present invention relates to a novel thermo-isomerization method for rapidly and simply producing macrocyclic ketones of the formula Ia or Ib. The macrocyclic ketones are prepared in the gas phase at temperatures above 500° C. rapidly and in a simple manner from alcohols of the formula IIa and IIb directly with a high yield. In the formulae Ia, Ib, IIa and IIb, R1-R5, and n have the meanings given in the description.Type: GrantFiled: February 15, 2002Date of Patent: October 4, 2005Assignee: Givaudan SAInventors: Georg Frater, Matthias Nagel
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Patent number: 6894198Abstract: An alkali metal alkoxide or alkaline earth metal alkoxide in granular form.Type: GrantFiled: October 15, 2002Date of Patent: May 17, 2005Assignee: Degussa AGInventors: Andreas Harthun, Christoph Theis, André Noppe, Josef Metz
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Patent number: 6867335Abstract: The present invention relates to process wherein (+)-2-carene epoxide is coupled with a compound X—Y that contains nucleophilic and electrophilic moieties, to produce a compound of formula (5). The reaction mixture consists essentially of a source of (+)-2-carene epoxide, compound X—Y, optionally an inert solvent and optionally a pH buffer. No acid catalyst is used in the process.Type: GrantFiled: May 9, 2002Date of Patent: March 15, 2005Assignee: Johnson Matthey Public Limited CompanyInventors: Michael Casner, Theodore Maurice Resnick, Lee Jonathan Silverberg
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Patent number: 6759557Abstract: A melanin synthesis inhibitor composition containing at least one macrocyclic compound represented by Formula (1) wherein X is a group selected among the groups consisting of C═O; CH—OH and O═C—CHOH; R being a chain hydrocarbon having 13 to 24 carbon atoms, R forms a ring with X and may be saturated or contain 1 to 3 unsaturated bonds and may be substituted by a lower alkyl group of 1 to 3 carbon atoms.Type: GrantFiled: June 10, 2002Date of Patent: July 6, 2004Assignee: Takasago International CorporationInventors: Hiroyuki Matsuda, Hiroyasu Kumamoto, Eiko Tamai, Misao Yagi, Kenichi Yamamoto, Toshimitsu Hagiwara, Shinya Watanabe
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Patent number: 6717017Abstract: The present invention provides a method of synthesizing compounds of formula (I) or (II): wherein R1 is hydrogen, R′ is (C1-C4)alkyl and X is a hydroxyl protecting group.Type: GrantFiled: August 30, 2002Date of Patent: April 6, 2004Assignee: The Regents of the University of CaliforniaInventor: Trevor C. McMorris
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Publication number: 20030149310Abstract: The present invention relates to a process for the preparation of iron-doped ruthenium catalysts supported on carbon, and their use for the selective liquid phase hydrogenation of carbonyl compounds to give the corresponding alcohols, in particular for the hydrogenation of citral to give geraniol or nerol or of citronellal to give citronellol.Type: ApplicationFiled: December 4, 2002Publication date: August 7, 2003Inventors: Till Gerlach, Hans-Georg Gobbel, Frank Funke, Klaus Ebel, Ekkehard Schwab, Signe Unverricht, Reinhard Korner, Lisa Lobree
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Publication number: 20030092775Abstract: A process for the preparation of optically pure acetylenediols of the formulae R-I and S-I 1Type: ApplicationFiled: September 10, 2002Publication date: May 15, 2003Inventors: Hansgeorg Ernst, Klaus Henrich, Klaus Ditrich
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Patent number: 6559118Abstract: Novel compounds having the structure (I) where R1 is a lower alkyl group, R2, R3, R4 and R5 is each independently hydrogen or a lower alkyl group, R6 is hydrogen, a lower alkyl group, an alkylidene group or a lower alkenyl group and R7 is hydrogen or a lower alkyl group, have desirable odor properties, possibly of a blackcurrant, green, buchu, cassis nature, and find use in perfumes and perfumed products.Type: GrantFiled: December 7, 2001Date of Patent: May 6, 2003Assignee: Quest International B.V.Inventor: Kenneth Palmer
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Patent number: 6515185Abstract: Cyclododecanone and cyclododecanol are produced each in high yield by reacting a epoxycyclododecane compound with hydrogen in the presence of a solid catalyst containing (a) catalytic component including a platinum group metal, (b) a promoter component including a VIII group, IIb group, IIIb group, IVb group, Vb group VIb group or VIIb group element or lanthanoid element or compound of the element, and (c) a carrier supporting the components (a) and (b) thereon.Type: GrantFiled: October 3, 2000Date of Patent: February 4, 2003Assignee: Ube Industries, Ltd.Inventors: Nobuyuki Kuroda, Hiroshi Shiraishi, Takato Nakamura
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Patent number: 6410807Abstract: A process for producing cyclohexene dimethanol or cyclohexane dimethanol compounds is provided. By controlling the rates of addition of certain reaction components and/or by controlling reaction solution temperatures at specific stages during synthesis, this invention provides a process for producing high purity cyclohexene dimethanol or cyclohexane dimethanol compounds without the need for solvent extraction and/or recrystallization procedures.Type: GrantFiled: May 10, 2000Date of Patent: June 25, 2002Assignee: Chevron Phillips Chemical Company LPInventors: Hu Yang, Ta Yen Ching, Gangfeng Cai
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Patent number: 6376722Abstract: A lutein to zeaxanthin isomerization process which includes a saponification or alkali treatment of a plant extract containing lutein followed by a heating period under controlled conditions, is carried out in the presence of a surface active agent having an HLB of from 1 to 40 as a catalyst for the lutein to zeaxanthin isomerization reaction, at a temperature between 70 to 140° C., in order to obtain a reaction product with high zeaxanthin concentrations of up to 80% of the total carotenoids.Type: GrantFiled: October 29, 1998Date of Patent: April 23, 2002Inventors: Vicente Ernesto Ridaura Sanz, Oscar Rubén García Correa, Armando Prado Naranjo
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Patent number: 6303837Abstract: Using the process according to the invention, it is possible to provide, with few reaction steps, a novel route to &agr;-substituted ring systems, which optionally have further substituents.Type: GrantFiled: August 31, 1999Date of Patent: October 16, 2001Assignee: Bayer AktiengesellschaftInventors: Christoph Gürtler, Manfred Jautelat
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Patent number: 6245952Abstract: The present invention relates to a process for the preparation of alcohols by reduction of the carbonyl function in substrates belonging to the class of aldehydes, ketones, esters or lactones, which substrates may contain unsaturated functions other than carbonyl. This process includes the steps of reacting the carbonyl substrate with stoichiometric amounts of a silane in the presence of catalytic amounts of an active zinc compound which is monomeric and not a hydride, hydrolyzing the thus-obtained siloxane with a basic agent, and separating and purifying, if necessary, the thus-obtained alcohol. The catalytically active compound is generally obtained by the reaction of an oligomeric or polymeric precursor compound of zinc with a complexing agent.Type: GrantFiled: March 1, 1999Date of Patent: June 12, 2001Assignee: Firmenich SAInventor: Hubert Mimoun
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Patent number: 6160184Abstract: The present invention provides a method of synthesizing compounds of ##STR1## wherein R and R' are independently (C.sub.1 -C.sub.4)alkyl.Type: GrantFiled: January 6, 2000Date of Patent: December 12, 2000Assignee: The Regents of the University of CaliforniaInventor: Trevor C. McMorris
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Patent number: 6111125Abstract: A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia ##STR1## which is required for preparing the red dye capsorubin which is in demand, starts from 2,2,6-trimethylcyclohexanones of the general formula II ##STR2## where R is hydrogen or a protective group, via the novel intermediates of the general formulae V and VI ##STR3## by diastereoselective epoxidation and reaction of the resulting 7-oxabicyclo[4.1.0]heptanes of the general formula VIII ##STR4## with Lewis acids and, where appropriate, removal of the protective group. Also claimed are the novel intermediates of the formula V and their (1S) and (1R) isomers and those of the formula VIII as well as their (1R,3S,6S), (1S,3S,6R) and (1R,3R,6S) isomers.Type: GrantFiled: March 3, 1995Date of Patent: August 29, 2000Assignee: BASF AktiengesellschaftInventors: Michael John, Udo Rheude, Joachim Paust, Joachim Meyer
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Patent number: 6103940Abstract: Preparing (3R, 3'R)-zeaxanthin of the formula I ##STR1## starting from (4-hydroxy-2,2,6-trimethylcyclohexanone of the formula II ##STR2## via the novel intermediates (4R,6R)-1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane of the formula IV ##STR3## (4R,6R)-1-(3-oxo-1-butenyl)-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane of the formula V ##STR4## (4R,6R)-1-(3- hydroxy-3-methyl-1,4-pentadienyl)-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptan e of the formula VI ##STR5## [5-(4R,6R)-(4-hydr oxy-2,2,6-trimethyl-1-cyclohexylidene)-3-methyl-1,3-pentadienyl]triarylphos phonium salt of the formula iso-III ##STR6## where Ar is aryl and X is one equivalent of an anion of a strong acid. The (4R,6R)-1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane of formula IV is obtained by reacting the ketone of the formula II with dichloromethyllithium, which can be prepared by metallation of dichloromethane with butyllithium or lithium diisopropylamide.Type: GrantFiled: June 4, 1998Date of Patent: August 15, 2000Assignee: BASF AktiengesellschaftInventors: Joachim Paust, Wolfgang Kriegl
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Patent number: 5973211Abstract: A method of isomerizing lutein to yield a mixture of epimers of zeaxanthin includes the following steps: mixing a lutein-containing extract in a glycol solution to obtain a mixture, treating the mixture with alkali to obtain an alkali-containing mixture, reacting the alkali-containing mixture in the presence of heat for a duration consistent with achieving a desired level of isomerization of lutein to zeaxanthin.Type: GrantFiled: July 18, 1997Date of Patent: October 26, 1999Assignee: Prodemex, S.A. DE C.V.Inventor: Gustavo Rodriguez
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Patent number: 5919986Abstract: Compounds of formula I: ##STR1## wherein the dotted carbon-carbon bond in the D-ring is C--C or C.dbd.C; C(R,R) is CH.sub.2 or C.dbd.CH.sub.2,R.sup.1 is H, F or OH,R.sup.2 and R.sup.3 are each independently C.sub.1-4 -alkyl or CF.sub.3, or together with the carbon to which they are bound form C.sub.3-6 -cycloalkyl.are useful in the treatment of vitamin D dependent disorders, such as psoriasis, leukemia; acne and seborrhoic dermatitis; osteoporosis hyperparathyroidism accompanying renal failure; and multiple sclerosis.Type: GrantFiled: October 13, 1998Date of Patent: July 6, 1999Assignee: Hoffmann-la Roche Inc.Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
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Patent number: 5814612Abstract: The present invention provides a purified retinoid compound characterized by a molecular mass of about 320 daltons and an atomic composition of C.sub.20 H.sub.32 O.sub.3. The present invention also provides a purified retinoid compound having the structure: ##STR1## wherein the configuration of the C7, C9, and C11 double bond independently is Z or E and the absolute configuration at C13 and C14 is independently R or S; wherein R1 is alkyl, alkyl halide, alcohol, ester, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, acyl halide, amide, nitrile, or amine; R2 and R3 are independently hydroxyl, halide, alkoxy, ester, alkyl, alcohol, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, nitrile, amine, azide, alkyl halide, acid halide, acid azide, or amide; or wherein R2 and R3, or R1 and R2 are replaced by a 13,14-oxirane or a 14,15-oxirane group, respectively.Type: GrantFiled: May 6, 1992Date of Patent: September 29, 1998Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia in the City of New YorkInventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
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Patent number: 5763689Abstract: This application relates to 3-substituted and 4-substituted cis-diols. Specifically, there are provided 3-substituted diols of formula (II) and 4-substituted cis-diols having (1S, 2R) and (1R, 2S) absolute configurations of formulae (III) and (IV). Also provided are processes For making such 3- and 4-substituted cis-diols using a reductive fission reaction. The compounds described herein are useful as synthons for the preparation of various compounds including therapeutics, agricultural, polymers and other classes of compounds. In formulae (II, III and IV), R is halogen, CN, aryl alkyl, alkenyl alkynyl O-alkyl, CF.sub.3 or NO.sub.2.Type: GrantFiled: February 29, 1996Date of Patent: June 9, 1998Inventors: Derek R. Boyd, Howard Dalton
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Patent number: 5648563Abstract: This invention provides a homogeneous retro-retinoid compound, a method of enhancing the growth of a cell in a vitamin A reduced environment, a method for enhancing transcription of a gene regulated by retinoid in a cell, and a method for enhancing an immune response in a subject, wherein the compound has the structure: ##STR1##Type: GrantFiled: June 7, 1995Date of Patent: July 15, 1997Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia University in the City of New YorkInventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
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Patent number: 5608088Abstract: A process for producing 3,4-caranediol of the formula [I] includes subjecting 3,4-epoxycarane, which is obtained by epoxidizing 3-carene under specific conditions, to a hydration reaction in the presence of a base catalyst in aqueous ethanol under pressure to obtain 3,4-caranediol.Type: GrantFiled: September 8, 1995Date of Patent: March 4, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Keisuke Watanabe, Noboru Yamamoto, Atsushi Kaetsu, Yoshimi Yamada
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Patent number: 5521221Abstract: This invention provides a purified retro-retinoid compound characterized by a molecular mass of about 302 daltons. Also provided by this invention is a method of enhancing the growth of a cell in a vitamin A reduced environment which comprises contacting the cell with an effective growth enhancing amount of a compound having a structure: ##STR1## wherein the configuration of the C6, C8, C10 and C12 double bond independently is Z or E and the absolute configuration at C-14 is independently R or S; wherein R.sub.1 is alkyl, alkyl halide, alcohol, ester, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, acid halide, amide, nitrile, or amine; and wherein R.sub.2 is hydroxyl, halide, alkoxy, ester, alkyl, alcohol, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, nitrile, amine, azide, alkyl halide, acid halide, acid azide, or amide; or wherein R.sub.1 and R.sub.2 are replaced by a 14, 15-oxirane group; and wherein the retro structure is alpha or gamma.Type: GrantFiled: April 9, 1991Date of Patent: May 28, 1996Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia University in the City of New YorkInventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
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Patent number: RE40912Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.Type: GrantFiled: June 10, 2005Date of Patent: September 8, 2009Assignee: The Catholic University of AmericaInventor: Frederick Khachik
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Patent number: RE40931Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.Type: GrantFiled: January 10, 2006Date of Patent: October 6, 2009Assignee: The Catholic University of AmericaInventor: Frederick Khachik
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Patent number: RE40938Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.Type: GrantFiled: February 5, 2007Date of Patent: October 13, 2009Assignee: The Catholic University of AmericaInventor: Frederick Khachik