2,6,6-trialkylcyclohexenyl (e.g., Vitamin A Derivatives, Etc.) Patents (Class 568/668)
  • Patent number: 8097762
    Abstract: The present invention relates to a process for converting lutein and/or lutein esters to (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. (3R)-?-Cryptoxanthin and (3R,6?R)-?-cryptoxanthin are two rare food carotenoids that are not commercially available and the former exhibits vitamin A activity. In the first synthetic step, commercially available lutein and/or lutein esters are transformed into a mixture of dehydration products of lutein (anhydroluteins) in the presence of a catalytic amount of an acid. The resulting anhydroluteins are then converted to (3R)-?-cryptoxanthin (major product) and (3R,6?R)-?-cryptoxanthin (minor product) by heterogeneous catalytic hydrogenation employing transition elements of group VIII (Pt, Pd, Rh supported on alumina or carbon) in a variety of organic solvents under atmospheric pressure of hydrogen and at temperatures ranging from ?15° C. to 40° C.
    Type: Grant
    Filed: July 12, 2010
    Date of Patent: January 17, 2012
    Assignee: University of Maryland, College Park
    Inventors: Frederick Khachik, Yufa Liu, Holly Showalter
  • Publication number: 20100247551
    Abstract: Methods of identifying compounds that modulate lipocalin 2 activity or expression are described, as are methods of reducing insulin resistance or increasing insulin sensitivity by administering compounds that modulate lipocalin 2 expression. Methods of diagnosing insulin resistance or related conditions, by measuring lipocalin 2 activity, are also described.
    Type: Application
    Filed: August 29, 2007
    Publication date: September 30, 2010
    Inventor: Evan D. Rosen
  • Patent number: 7115786
    Abstract: The present invention relates to a method of reacting (3R,3?R,6?R)-lutein with a catalytic amount of an acid to obtain a mixture of anhydroluteins, rich in anhydrolutein III, with substantially no Z-isomers being formed. The mixture is converted to (3R)-?-cryptoxanthin (major product) and (3R,6?R)-?-cryptoxanthin (minor product) by reacting the anhydroluteins with borane-amine complexes (e.g. Me3N.BH3) or other hydride donors and an acid in a chlorinated solvent, preferably dichloromethane, at ambient temperature to produce (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin.
    Type: Grant
    Filed: February 6, 2003
    Date of Patent: October 3, 2006
    Assignee: University of Maryland, College Park
    Inventor: Frederick Khachik
  • Patent number: 7071228
    Abstract: A method of treating said musculoskeletal and connective tissue inflammations including osteoarthritis and associated articular and periarticular inflammations, and non-articular Rheumatism including capsulitis, tendonitis, fibrositis, and perarticular inflammations is disclosed. The method includes administering to a patient of a therapeutically effective amount of a composition comprising 13-cis-retinoic acid. Preferably, the treatment method includes administering to a patient of an initial dosage of a composition comprising 13-cis-retinoic acid for an initial treatment period, and thereafter administering a maintenance dosage of the composition.
    Type: Grant
    Filed: October 23, 2002
    Date of Patent: July 4, 2006
    Inventor: L. Dean Parks
  • Publication number: 20040236154
    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.
    Type: Application
    Filed: June 1, 2004
    Publication date: November 25, 2004
    Inventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
  • Patent number: 6180670
    Abstract: Skin aging and related conditions can be effectively treated with a conjugate of a retinoid and a bioactive organic acid preferably selected from among alpha-hydroxy acids, beta-hydroxy acids, and keto-acids; preferred conjugates include retinyl glycolyl ether and retinyl glycolate (as either the ester or reverse ester).
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: January 30, 2001
    Assignee: Avon Products, Inc.
    Inventors: John A. Duffy, Janice J. Teal, Mark S. Garrison, George P. Serban
  • Patent number: 5908957
    Abstract: A process is disclosed for the catalyzed isomerization of a Z-isomer of a vitamin A compound or of a mixture of several of such isomers into a mixture of the corresponding all-E- and 13-Z-isomers of this vitamin A compound. The process utilizes nitrogen monoxide or a gas mixture containing nitrogen monoxide as the isomerization catalyst. Vitamin A acetate or vitamin A acid is preferably used as the vitamin A compound. The thus-produced all-E vitamin A and its alkanoyl esters have of all isomers by far the highest biological activity and are accordingly almost exclusively used in human and animal nutrition. The 13-Z-vitamin A compounds in turn play an important role as pharmaceutically active substances.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: June 1, 1999
    Assignee: Roche Vitamins Inc.
    Inventor: Angela Wildermann
  • Patent number: 5663459
    Abstract: The present invention relates to novel intermediates for the preparation of vitamin A and carotenoids corresponding to the formula (II): ##STR1## in which A represents a hydrogen or an alkyl, alkenyl or alkoxy group containing 1 to 4 carbon atoms, and X represents a carbon atom, and to a process for their preparation and their use, and further relates to compounds for preparing intermediates of formula (II) corresponding to the formula (III): ##STR2## in which R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkylcarbonyl, alkenylcarbonyl, alkoxyalkyl or alkoxyalkenyl group in which the alkyl groups have 1 to 10 carbon atoms and the alkenyl groups have 2 to 10 carbon atoms, each of said groups being linear or branched and each being substituted or unsubstituted.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 2, 1997
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Hugues Bienayme, Pierre Meilland
  • Patent number: 5313002
    Abstract: The invention relates to novel ethers and their use as aroma precursors. The ethers are derived from ionol and related compounds. These aroma precursors do not have a substantial aroma as such under ambient conditions, but will break up into a complex mixture having useful organoleptic properties under heating. The ethers are especially suitable for use in products which are heated, burned or smouldered in some stage of their use. The compounds according to the invention are especially suitable for application to tobacco. Mixtures obtained by degrading (e.g. by heating) the ethers according to the invention may be used in a flavouring or perfuming mixture as well due to their organoleptic properties.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: May 17, 1994
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Johannes T. De Heij, Franciscus P. Van Lier, Harrie Renes
  • Patent number: 5243094
    Abstract: Derivatives of long-chain fatty alcohols, and methods of obtaining them, are provided, as well as pharmaceutical compositions containing derivatives and their uses, in particular in treating or preventing neuro-degenerative illnesses, conditions linked to skin ageing, the phenomena of thrombosis and atherosclerosis, and immune deficiencies.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: September 7, 1993
    Assignee: Medafor
    Inventor: Jacques Borg
  • Patent number: 5066815
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: November 19, 1991
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 4952716
    Abstract: A process for the manufacture of compounds of the general formula ##STR1## wherein R.sup.1 signifies hydroxy or an etherified hydroxy group, and of zeaxanthin by converting a compound of the general formula ##STR2## wherein R.sup.1 has the above significance, in an inert organic solvent into the acetylenide and reacting this with methyl vinyl ketone, reducing the alcoholate obtained or the alcohol (obtained after hydrolysis of the alcoholate) of the general formula ##STR3## wherein R.sup.1 has the above significance, and subsequently hydrolyzing to give the compound of formula IV and, if desired, converting the compound of formula IV obtained into zeaxanthin.
    Type: Grant
    Filed: March 4, 1988
    Date of Patent: August 28, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup
  • Patent number: 4701540
    Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 20, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • Patent number: 4614747
    Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: September 30, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
  • Patent number: 4487944
    Abstract: New acetylenic and allenic carbinols of formula ##STR1## respectively, wherein symbol R stands for a trialkyl-silyl or a C.sub.1 to C.sub.6 alkyl radical, preferably a methyl, a tert-butyl or an isoamyl radical, or a group of formula ##STR2## wherein, when taken separately, each of symbols R.sup.1 and R.sup.2 represents a lower alkyl radical or, when taken together, R.sup.1 and R.sup.2 represent a tetramethylene group, are useful intermediates for the preparation of .beta.-damascenone.
    Type: Grant
    Filed: September 27, 1983
    Date of Patent: December 11, 1984
    Assignee: Firmenich, SA
    Inventors: Karl-Heinrich Schulte-Elte, Bernard M/u/ ller
  • Patent number: 4474983
    Abstract: 1,5-Dimethyl-hexa-1,5-dienylene compounds, and especially Vitamin A and derivatives thereof, are made by desuphonylating with a basic reagent a sulphone of the formula: ##STR1## in which the sulphonyl group --SO.sub.2 R replaces a hydrogen atom on carbon atom (a) or (b), R represents a phenyl or napthyl group, A is 2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl, and Q is --CH.sub.2 OH or an ether or ester thereof, CHO, or an acetal group.
    Type: Grant
    Filed: February 4, 1982
    Date of Patent: October 2, 1984
    Assignee: Rhone-Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4331814
    Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.
    Type: Grant
    Filed: February 1, 1973
    Date of Patent: May 25, 1982
    Assignee: Rhone Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4296259
    Abstract: A new process for preparing 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-1,4-pentadien-3-ol, a intermediate for canthaxanthin, from hydroxy-.beta.-ionone.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: October 20, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Urs Hengartner
  • Patent number: 4227022
    Abstract: A total synthesis of canthaxanthin or dinor-canthaxanthin, known food coloring agents, from pentols.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: October 7, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger