Unsaturation In The Ring Patents (Class 568/823)
  • Patent number: 8716535
    Abstract: 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: Grant
    Filed: October 16, 2008
    Date of Patent: May 6, 2014
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Patent number: 8716534
    Abstract: 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: Grant
    Filed: October 16, 2008
    Date of Patent: May 6, 2014
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Patent number: 8614345
    Abstract: 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: Grant
    Filed: December 19, 2011
    Date of Patent: December 24, 2013
    Assignee: Firmenich SA
    Inventors: Francesco Santoro, Lionel Saudan, Michel Alfred Joseph Saudan, Sylvia Joyeuse Adélaïde Ada Saudan
  • Patent number: 8278332
    Abstract: 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: Grant
    Filed: October 27, 2011
    Date of Patent: October 2, 2012
    Assignee: Hallstar Innovations Corp.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Patent number: 8263051
    Abstract: 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: Grant
    Filed: April 5, 2011
    Date of Patent: September 11, 2012
    Assignee: Hallstar Innovations Corp.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Patent number: 8133477
    Abstract: 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: Grant
    Filed: September 4, 2009
    Date of Patent: March 13, 2012
    Assignee: Hallstar Innovations Corp.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Patent number: 8115036
    Abstract: 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: Grant
    Filed: April 22, 2010
    Date of Patent: February 14, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Haruhiko Komoriya, Shinichi Sumida, Michitaka Ootani, Takeo Komata, Kazuhiko Maeda
  • Patent number: 8070989
    Abstract: 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: Grant
    Filed: July 31, 2009
    Date of Patent: December 6, 2011
    Assignee: Hallstar Innovations Corp.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Patent number: 8063254
    Abstract: 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: Grant
    Filed: October 29, 2008
    Date of Patent: November 22, 2011
    Assignee: Kaneka Corporation
    Inventors: Takahiro Ueda, Shiro Kitamura
  • Patent number: 7902393
    Abstract: 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: Grant
    Filed: May 18, 2009
    Date of Patent: March 8, 2011
    Assignee: Firmenich SA
    Inventors: Charles Fehr, Magali Vuagnoux
  • Patent number: 7875751
    Abstract: 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: Grant
    Filed: November 7, 2008
    Date of Patent: January 25, 2011
    Assignee: Allied Biotech Corporation
    Inventors: Chia-Line Chuang, Hsin-Ke Li, Chong-Nan Chuang
  • Patent number: 7767866
    Abstract: 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: Grant
    Filed: March 12, 2009
    Date of Patent: August 3, 2010
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Publication number: 20090324570
    Abstract: 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: Application
    Filed: July 31, 2009
    Publication date: December 31, 2009
    Applicant: HALLSTAR INNOVATIONS CORP.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Patent number: 7550417
    Abstract: 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: Grant
    Filed: September 8, 2006
    Date of Patent: June 23, 2009
    Assignee: Givandan SA
    Inventors: Jerzy A. Bajgrowicz, Iris Frank
  • Patent number: 7521582
    Abstract: 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: Grant
    Filed: August 24, 2007
    Date of Patent: April 21, 2009
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Patent number: 7495135
    Abstract: 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: Grant
    Filed: December 4, 2003
    Date of Patent: February 24, 2009
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Patent number: 7442828
    Abstract: 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: Grant
    Filed: August 24, 2007
    Date of Patent: October 28, 2008
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Patent number: 7323607
    Abstract: 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: Grant
    Filed: April 14, 2004
    Date of Patent: January 29, 2008
    Assignee: Mallinckrodt Inc.
    Inventors: Hong Gu, J. Kendall Killgore, John R. Duchek
  • Patent number: 7153979
    Abstract: 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: Grant
    Filed: February 24, 2003
    Date of Patent: December 26, 2006
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Kazue Sasaki, Nobuto Minowa, Shoji Nishiyama, Hiroyuki Kuzuhara
  • Patent number: 7145044
    Abstract: 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: Grant
    Filed: July 15, 2002
    Date of Patent: December 5, 2006
    Assignee: Kaneka Corporation
    Inventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
  • Patent number: 7132391
    Abstract: 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: Grant
    Filed: July 10, 2002
    Date of Patent: November 7, 2006
    Assignee: Takasago International Corporation
    Inventors: Takashi Aida, Andrew T. Lupo, Hiroyuki Matsuda
  • Patent number: 7105709
    Abstract: 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: Grant
    Filed: July 15, 2002
    Date of Patent: September 12, 2006
    Assignee: Kaneka Corporation
    Inventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
  • Patent number: 7078570
    Abstract: 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: Grant
    Filed: December 3, 2001
    Date of Patent: July 18, 2006
    Assignee: Givaudan SA
    Inventor: Andreas Goeke
  • Patent number: 7012161
    Abstract: 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: Grant
    Filed: August 16, 2004
    Date of Patent: March 14, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Takeshi Kinsho, Yuji Harada
  • Patent number: 6951964
    Abstract: 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: Grant
    Filed: February 15, 2002
    Date of Patent: October 4, 2005
    Assignee: Givaudan SA
    Inventors: Georg Frater, Matthias Nagel
  • Patent number: 6894198
    Abstract: An alkali metal alkoxide or alkaline earth metal alkoxide in granular form.
    Type: Grant
    Filed: October 15, 2002
    Date of Patent: May 17, 2005
    Assignee: Degussa AG
    Inventors: Andreas Harthun, Christoph Theis, André Noppe, Josef Metz
  • Patent number: 6867335
    Abstract: 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: Grant
    Filed: May 9, 2002
    Date of Patent: March 15, 2005
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Michael Casner, Theodore Maurice Resnick, Lee Jonathan Silverberg
  • Patent number: 6759557
    Abstract: 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: Grant
    Filed: June 10, 2002
    Date of Patent: July 6, 2004
    Assignee: Takasago International Corporation
    Inventors: Hiroyuki Matsuda, Hiroyasu Kumamoto, Eiko Tamai, Misao Yagi, Kenichi Yamamoto, Toshimitsu Hagiwara, Shinya Watanabe
  • Patent number: 6717017
    Abstract: 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: Grant
    Filed: August 30, 2002
    Date of Patent: April 6, 2004
    Assignee: The Regents of the University of California
    Inventor: Trevor C. McMorris
  • Publication number: 20030149310
    Abstract: 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: Application
    Filed: December 4, 2002
    Publication date: August 7, 2003
    Inventors: Till Gerlach, Hans-Georg Gobbel, Frank Funke, Klaus Ebel, Ekkehard Schwab, Signe Unverricht, Reinhard Korner, Lisa Lobree
  • Publication number: 20030092775
    Abstract: A process for the preparation of optically pure acetylenediols of the formulae R-I and S-I 1
    Type: Application
    Filed: September 10, 2002
    Publication date: May 15, 2003
    Inventors: Hansgeorg Ernst, Klaus Henrich, Klaus Ditrich
  • Patent number: 6559118
    Abstract: 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: Grant
    Filed: December 7, 2001
    Date of Patent: May 6, 2003
    Assignee: Quest International B.V.
    Inventor: Kenneth Palmer
  • Patent number: 6515185
    Abstract: 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: Grant
    Filed: October 3, 2000
    Date of Patent: February 4, 2003
    Assignee: Ube Industries, Ltd.
    Inventors: Nobuyuki Kuroda, Hiroshi Shiraishi, Takato Nakamura
  • Patent number: 6410807
    Abstract: 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: Grant
    Filed: May 10, 2000
    Date of Patent: June 25, 2002
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Hu Yang, Ta Yen Ching, Gangfeng Cai
  • Patent number: 6376722
    Abstract: 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: Grant
    Filed: October 29, 1998
    Date of Patent: April 23, 2002
    Inventors: Vicente Ernesto Ridaura Sanz, Oscar Rubén García Correa, Armando Prado Naranjo
  • Patent number: 6303837
    Abstract: 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: Grant
    Filed: August 31, 1999
    Date of Patent: October 16, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christoph Gürtler, Manfred Jautelat
  • Patent number: 6245952
    Abstract: 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: Grant
    Filed: March 1, 1999
    Date of Patent: June 12, 2001
    Assignee: Firmenich SA
    Inventor: Hubert Mimoun
  • Patent number: 6160184
    Abstract: 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: Grant
    Filed: January 6, 2000
    Date of Patent: December 12, 2000
    Assignee: The Regents of the University of California
    Inventor: Trevor C. McMorris
  • Patent number: 6111125
    Abstract: 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: Grant
    Filed: March 3, 1995
    Date of Patent: August 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael John, Udo Rheude, Joachim Paust, Joachim Meyer
  • Patent number: 6103940
    Abstract: 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: Grant
    Filed: June 4, 1998
    Date of Patent: August 15, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Paust, Wolfgang Kriegl
  • Patent number: 5973211
    Abstract: 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: Grant
    Filed: July 18, 1997
    Date of Patent: October 26, 1999
    Assignee: Prodemex, S.A. DE C.V.
    Inventor: Gustavo Rodriguez
  • Patent number: 5919986
    Abstract: 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: Grant
    Filed: October 13, 1998
    Date of Patent: July 6, 1999
    Assignee: Hoffmann-la Roche Inc.
    Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
  • Patent number: 5814612
    Abstract: 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: Grant
    Filed: May 6, 1992
    Date of Patent: September 29, 1998
    Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia in the City of New York
    Inventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
  • Patent number: 5763689
    Abstract: 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: Grant
    Filed: February 29, 1996
    Date of Patent: June 9, 1998
    Inventors: Derek R. Boyd, Howard Dalton
  • Patent number: 5648563
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: July 15, 1997
    Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia University in the City of New York
    Inventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
  • Patent number: 5608088
    Abstract: 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: Grant
    Filed: September 8, 1995
    Date of Patent: March 4, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keisuke Watanabe, Noboru Yamamoto, Atsushi Kaetsu, Yoshimi Yamada
  • Patent number: 5521221
    Abstract: 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: Grant
    Filed: April 9, 1991
    Date of Patent: May 28, 1996
    Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia University in the City of New York
    Inventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
  • Patent number: RE40912
    Abstract: 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: Grant
    Filed: June 10, 2005
    Date of Patent: September 8, 2009
    Assignee: The Catholic University of America
    Inventor: Frederick Khachik
  • Patent number: RE40931
    Abstract: 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: Grant
    Filed: January 10, 2006
    Date of Patent: October 6, 2009
    Assignee: The Catholic University of America
    Inventor: Frederick Khachik
  • Patent number: RE40938
    Abstract: 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: Grant
    Filed: February 5, 2007
    Date of Patent: October 13, 2009
    Assignee: The Catholic University of America
    Inventor: Frederick Khachik