US20060178538A1 - Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids - Google Patents

Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids Download PDF

Info

Publication number
US20060178538A1
US20060178538A1 US11/242,641 US24264105A US2006178538A1 US 20060178538 A1 US20060178538 A1 US 20060178538A1 US 24264105 A US24264105 A US 24264105A US 2006178538 A1 US2006178538 A1 US 2006178538A1
Authority
US
United States
Prior art keywords
compound
chiral
carotenoids
general structure
synthesis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US11/242,641
Other languages
English (en)
Inventor
Samuel Lockwood
Peng Tang
Geoff Nadolski
Henry Jackson
Zhiqiang Fang
Yishu Du
Min Yang
William Geiss
Richard Williams
David Burdick
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cardax Pharmaceuticals Inc
Original Assignee
Cardax Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cardax Pharmaceuticals Inc filed Critical Cardax Pharmaceuticals Inc
Priority to US11/242,641 priority Critical patent/US20060178538A1/en
Assigned to HAWAII BIOTECH, INC. reassignment HAWAII BIOTECH, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BURDICK, DAVID, DU, YISHU, FANG, ZHIQIANG, GEISS, WILLIAM, JACKSON, HENRY L., LOCKWOOD, SAMUEL F., NADOLSKI, GEOFF, TANG, PENG CHO, WILLIAMS, RICHARD, YANG, MIN
Publication of US20060178538A1 publication Critical patent/US20060178538A1/en
Assigned to CARDAX PHARMACEUTICALS, INC. reassignment CARDAX PHARMACEUTICALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HAWAII BIOTECH, INC.
Abandoned legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US11/242,641 2004-10-01 2005-10-03 Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids Abandoned US20060178538A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/242,641 US20060178538A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US61503204P 2004-10-01 2004-10-01
US67595705P 2005-04-29 2005-04-29
US69151805P 2005-06-17 2005-06-17
US69268205P 2005-06-21 2005-06-21
US69965305P 2005-07-15 2005-07-15
US70238005P 2005-07-26 2005-07-26
US71235005P 2005-08-30 2005-08-30
US11/242,641 US20060178538A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids

Publications (1)

Publication Number Publication Date
US20060178538A1 true US20060178538A1 (en) 2006-08-10

Family

ID=36042942

Family Applications (8)

Application Number Title Priority Date Filing Date
US11/242,641 Abandoned US20060178538A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids
US11/242,645 Abandoned US20060183185A1 (en) 2004-10-01 2005-10-03 Method for the synthesis of astaxanthin
US11/242,627 Abandoned US20060111580A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids
US11/242,615 Abandoned US20060155150A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of lutein
US11/242,643 Active US7247752B2 (en) 2004-10-01 2005-10-03 Methods for the synthesis of astaxanthin
US11/242,591 Abandoned US20060088904A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of astaxanthin
US11/242,609 Abandoned US20060167319A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids
US11/242,639 Abandoned US20060088905A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of zeazanthin

Family Applications After (7)

Application Number Title Priority Date Filing Date
US11/242,645 Abandoned US20060183185A1 (en) 2004-10-01 2005-10-03 Method for the synthesis of astaxanthin
US11/242,627 Abandoned US20060111580A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids
US11/242,615 Abandoned US20060155150A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of lutein
US11/242,643 Active US7247752B2 (en) 2004-10-01 2005-10-03 Methods for the synthesis of astaxanthin
US11/242,591 Abandoned US20060088904A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of astaxanthin
US11/242,609 Abandoned US20060167319A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids
US11/242,639 Abandoned US20060088905A1 (en) 2004-10-01 2005-10-03 Methods for the synthesis of zeazanthin

Country Status (2)

Country Link
US (8) US20060178538A1 (US20060178538A1-20060810-C00091.png)
WO (1) WO2006039685A2 (US20060178538A1-20060810-C00091.png)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050009930A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling connexin 43 expression
US20050037995A1 (en) * 2002-07-29 2005-02-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US20050065096A1 (en) * 2002-07-29 2005-03-24 Lockwood Samuel Fournier Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050090469A1 (en) * 2002-07-29 2005-04-28 Lockwood Samuel F. Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease
US20050113372A1 (en) * 2002-07-29 2005-05-26 Lockwood Samuel F. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US20060088905A1 (en) * 2004-10-01 2006-04-27 Lockwood Samuel F Methods for the synthesis of zeazanthin
US20090099061A1 (en) * 2006-01-27 2009-04-16 Foss Bente J Synthesis of carotenoid analogs or derivatives with improved antioxidant characteristics
US20090124574A1 (en) * 2007-03-23 2009-05-14 Lockwood Samuel F Carotenoid analogs and derivatives for the prevention of platelet aggregation
WO2016007587A3 (en) * 2014-07-08 2016-04-07 Valent Biosciences Corporation 3'-substituted-abscisic acid derivatives

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA83341C2 (uk) 2002-02-25 2008-07-10 Дифьюжен Фармасьютикалз Ллк Біополярні солі транс-каротиноїдів та їх використання
US7759506B2 (en) 2002-02-25 2010-07-20 Diffusion Pharmaceuticals Llc Bipolar trans carotenoid salts and their uses
US20050059659A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling C-reactive protein levels
US20050148517A1 (en) * 2002-07-29 2005-07-07 Lockwood Samuel F. Carotenoid ether analogs or derivatives for controlling connexin 43 expression
US20050049248A1 (en) * 2002-07-29 2005-03-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for controlling C-reactive protein levels
US20050059635A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling C-reactive protein levels
WO2006104610A2 (en) 2005-02-24 2006-10-05 Diffusion Pharmaceuticals Llc Trans carotenoids, their synthesis, formulation and uses
US7435861B2 (en) * 2005-04-29 2008-10-14 Cardax Pharmaceuticals, Inc. Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
US20080221377A1 (en) * 2006-06-16 2008-09-11 Lockwood Samuel F Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
CN101148433B (zh) * 2006-09-20 2011-01-12 浙江医药股份有限公司新昌制药厂 十五碳醇的合成方法
CN101646642A (zh) * 2007-03-28 2010-02-10 巴斯夫欧洲公司 对映选择性制备光学活性4-羟基-2,6,6-三甲基环己-2-烯酮衍生物的方法
EA201070544A1 (ru) 2007-10-31 2010-12-30 Диффьюжн Фармасьютикалз Ллс Новый класс терапевтических веществ, усиливающих диффузию низкомолекулярных соединений
EP2130833A1 (en) 2008-06-05 2009-12-09 DSM IP Assets B.V. Process for the preparation of zeacarotenes
KR101782023B1 (ko) 2009-06-22 2017-10-23 디퓨젼 파마슈티컬즈 엘엘씨 확산 촉진 화합물 및 그 화합물 단독 또는 혈전 용해제와 합쳐진 화합물의 용도
US9913810B2 (en) 2009-07-23 2018-03-13 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using phospholipids and astaxanthin
US8481072B2 (en) * 2009-07-23 2013-07-09 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain
US9238043B2 (en) 2009-07-23 2016-01-19 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using algae based oils
US9216164B2 (en) 2009-07-23 2015-12-22 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using a mixture of fish oil and fish oil derived, choline based, phospholipid bound fatty acid mixture including polyunsaturated EPA and DHA
US8557275B2 (en) 2009-07-23 2013-10-15 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using a mixture of fish oil and fish oil derived, choline based, phospholipid bound fatty acid mixture including polyunsaturated EPA and DHA
US9402857B2 (en) 2009-07-23 2016-08-02 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using low molecular weight hyaluronic acid and astaxanthin
US9399047B2 (en) 2009-07-23 2016-07-26 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using phospholipids and roe extract
KR101891357B1 (ko) 2010-06-02 2018-08-24 디퓨젼 파마슈티컬즈 엘엘씨 양극성 트랜스 카로티노이드의 경구용 제형
CN101906445B (zh) * 2010-06-18 2013-01-23 西南大学 2h-1-苯并吡喃-2-酮衍生物的合成方法
WO2016011130A1 (en) * 2014-07-17 2016-01-21 National Taiwan University Compositions and methods for the preparation of 4-oxy-2-cyclohexenone and 6-oxy-2-cyclohexenone compounds
US10017465B2 (en) 2014-08-12 2018-07-10 Basf Se Method for producing astaxanthin from astacin
JP2017524716A (ja) 2014-08-12 2017-08-31 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 環状α−ケトエノールから環状α−ケトアルコールを製造する方法
CN105541573B (zh) * 2016-01-19 2017-11-24 四川大学 一种制备2,6,11,15‑四甲基‑2,4,6,8,10,12,14‑十六碳七烯二醛的方法
JP7032320B2 (ja) 2016-03-24 2022-03-08 ディフュージョン・ファーマシューティカルズ・エルエルシー 癌を処置するための、化学療法及び放射線療法を伴う二極性トランスカロテノイドの使用
CN106520715B (zh) * 2016-10-17 2019-06-28 浙江大学 一种短链脱氢酶及其基因、重组表达载体、基因工程菌及其在虾青素手性中间体合成中的应用
CN110121489A (zh) 2016-12-19 2019-08-13 巴斯夫欧洲公司 制备(4s)-或(4r)-3,4-二羟基-2,6,6-三甲基环己-2-烯酮的方法
WO2018114733A1 (en) * 2016-12-19 2018-06-28 Basf Se Process for the preparation of stereoisomeric pure c9-acetals
CN107445791A (zh) * 2017-07-31 2017-12-08 肇庆巨元生化有限公司 一种番茄红素的制备方法
CN114573488A (zh) * 2020-12-02 2022-06-03 中国科学院大连化学物理研究所 一种利用制备色谱对雨生红球藻来源的虾青素进行分离纯化的方法
CN114369048B (zh) * 2021-12-21 2023-12-26 上虞新和成生物化工有限公司 一种催化合成虾青素的方法

Citations (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3206316A (en) * 1960-10-17 1965-09-14 Hoffmann La Roche Water dispersible carotenoid preparations and processes thereof
US3354218A (en) * 1963-05-10 1967-11-21 Hoffmann La Roche Process for preparing 4-(2, 6, 6-trimethyl-4-methoxy-1-cyclohexen-1-yl)-3-buten-2-one
US3755422A (en) * 1970-01-15 1973-08-28 Rhone Poulenc Sa Preparation of carotenoid compounds
US3989757A (en) * 1973-08-29 1976-11-02 Hoffmann-La Roche Inc. Isomerizing cis-carotenoids to all-trans-carotenoids
US4245109A (en) * 1978-06-02 1981-01-13 Hoffmann-La Roche Inc. Process for producing astaxanthin
US4283559A (en) * 1978-06-02 1981-08-11 Hoffmann-La Roche Inc. Process for the manufacture of cyclohexene derivatives
US4435427A (en) * 1980-12-19 1984-03-06 Basf Aktiengesellschaft Stable injectable β-carotene micellar solutions and their preparation
US4585885A (en) * 1982-08-20 1986-04-29 Hoffmann-La Roche Inc. Cyclohexenone derivatives and process for making same
US4952716A (en) * 1987-03-27 1990-08-28 Hoffmann-La Roche Inc. Ethynylcyclohexene compounds
US5227507A (en) * 1987-03-27 1993-07-13 Hoffmann-La Roche Inc. Ethynylcyclohexene compounds and processes for manufacture thereof
US5310554A (en) * 1992-10-27 1994-05-10 Natural Carotene Corporation High purity beta-carotene
US5328845A (en) * 1992-03-27 1994-07-12 Universal Foods Corporation Fungal negative microorganism capable of producing high levels of beta-carotene
US5364563A (en) * 1989-07-25 1994-11-15 Hoffmann-La Roche Inc. Powdered aqueous carotenoid dispersions
US5422247A (en) * 1992-03-27 1995-06-06 Universal Foods Corporation Blakeslea trispora mated culture capable of increased beta-carotene production
US5455362A (en) * 1993-07-05 1995-10-03 Basf Aktiengesellschaft Preparation of astaxanthin novel intermediates therefor and the preparation thereof
US5492701A (en) * 1993-07-08 1996-02-20 Rhone-Poulenc Nutrition Animale Process for the preparation of spherules
US5536504A (en) * 1993-11-19 1996-07-16 Marigen S.A. Ultramicroemulsions from spontaneously dispersible concentrates containing xanthophyll esters and having antitumor activity
US5543559A (en) * 1994-07-07 1996-08-06 Hoffman-La Roche Inc. Process for the enantioselective hydrogenation of ketosiophorone derivatives
US5607839A (en) * 1993-07-22 1997-03-04 Nippon Oil Company, Ltd. Bacteria belonging to new genus process for production of carotenoids using same
US5612485A (en) * 1992-06-04 1997-03-18 Betatene Ltd Of Cheltenham High cis beta-carotene composition
US5654488A (en) * 1995-03-18 1997-08-05 Basf Aktiengesellschaft Preparation of astaxanthin
US5849345A (en) * 1994-12-21 1998-12-15 Roche Vitamins Inc. Carotenoid ketones and esters
US5854015A (en) * 1995-10-31 1998-12-29 Applied Food Biotechnology, Inc. Method of making pure 3R-3'R stereoisomer of zeaxanthin for human ingestion
US5858700A (en) * 1997-04-03 1999-01-12 Kemin Foods, Lc Process for the isolation and purification of lycopene crystals
US5871766A (en) * 1990-10-01 1999-02-16 Brigham And Women's Hospital Beta-carotene vitamin E therapy for inhibition of major vascular events
US5876782A (en) * 1997-05-14 1999-03-02 Kemin Industries, Inc. Method for the conversion of xanthophylls in plant material
US5959138A (en) * 1997-11-25 1999-09-28 Industrial Organica S.A. De C.V. Short chain diesters and process for making the same
US6020003A (en) * 1998-02-23 2000-02-01 Basf Corporation Method of making spray-dried powders with high edible-oil loadings based on non-hydrolyzed gelatin
US6046181A (en) * 1995-10-17 2000-04-04 Showa Denko K.K. Highly purified tocopheryl phosphate, process for producing the same, analytical method therefor and cosmetic
US6060511A (en) * 1995-10-05 2000-05-09 Gainer; John L. Trans-sodium crocetinate, methods of making and methods of use thereof
US6245818B1 (en) * 1997-09-04 2001-06-12 Astacarotene Ab Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases
US6335015B1 (en) * 1997-12-16 2002-01-01 Astacarotene Ab Method of the prophylactic treatment of mastitis
US6540654B2 (en) * 2001-02-23 2003-04-01 Luis W. Levy Carotenoid esters
US20030143660A1 (en) * 2001-11-20 2003-07-31 Qiong Cheng Method for production of asymmetric carotenoids
US6610892B2 (en) * 2001-03-12 2003-08-26 Basf Aktiengesellschaft Process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals
US6673971B2 (en) * 1999-09-30 2004-01-06 Basf Aktiengesellschaft Preparation of 1,1,4,4-tetramethoxy-2-butene
US20040049082A1 (en) * 2001-01-26 2004-03-11 Christoph Wegner Thermal isomerizaton of lycopene
US6747177B2 (en) * 2001-09-13 2004-06-08 Basf Aktiengesellschaft Process for the preparation of meso-zeaxanthin
US20040162329A1 (en) * 2002-07-29 2004-08-19 Lockwood Samuel Fournier Structural carotenoid analogs for the inhibition and amelioration of disease
US6827941B1 (en) * 1998-01-21 2004-12-07 Basf Aktiengesellschaft Use of carotenoid aggregates as colorants
US20050004235A1 (en) * 2002-07-29 2005-01-06 Lockwood Samuel Fournier Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease
US20050009930A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling connexin 43 expression
US20050009758A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050009788A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling connexin 43 expression
US20050026874A1 (en) * 2002-07-29 2005-02-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease
US20050049248A1 (en) * 2002-07-29 2005-03-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for controlling C-reactive protein levels
US20050059635A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling C-reactive protein levels
US20050059659A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling C-reactive protein levels
US20050065096A1 (en) * 2002-07-29 2005-03-24 Lockwood Samuel Fournier Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050075316A1 (en) * 2002-07-29 2005-04-07 Lockwood Samuel Fournier Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease
US20050090469A1 (en) * 2002-07-29 2005-04-28 Lockwood Samuel F. Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease
US20050113372A1 (en) * 2002-07-29 2005-05-26 Lockwood Samuel F. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US20050143475A1 (en) * 2002-07-29 2005-06-30 Lockwood Samuel F. Carotenoid analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US20050148517A1 (en) * 2002-07-29 2005-07-07 Lockwood Samuel F. Carotenoid ether analogs or derivatives for controlling connexin 43 expression
US20050261254A1 (en) * 2004-04-14 2005-11-24 Lockwood Samuel F Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US20060058269A1 (en) * 2004-04-14 2006-03-16 Lockwood Samuel F Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US20060088905A1 (en) * 2004-10-01 2006-04-27 Lockwood Samuel F Methods for the synthesis of zeazanthin

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE13876T1 (de) 1982-01-28 1985-07-15 Hoffmann La Roche Verfahren zur herstellung von cycloalkenonderivaten.
JPH07300421A (ja) 1994-04-28 1995-11-14 Itano Reitou Kk 抗炎症剤
JPH0873312A (ja) 1994-09-02 1996-03-19 Noevir Co Ltd 皮膚外用剤
JPH08337592A (ja) 1995-06-13 1996-12-24 Kaiyo Bio Technol Kenkyusho:Kk 新規カロテノイド
JPH0984591A (ja) 1995-09-26 1997-03-31 Kaiyo Bio Technol Kenkyusho:Kk カロテノイド硫酸エステルおよびその製造方法
JPH09202730A (ja) 1996-01-24 1997-08-05 Nippon Mektron Ltd 発ガン抑制作用剤
JPH10327865A (ja) 1997-05-29 1998-12-15 Kirin Brewery Co Ltd カロテノイド配糖体およびその製造法
DE60317770T3 (de) 2002-02-06 2013-07-25 Dsm Ip Assets B.V. Astaxanthinester
DE10358003A1 (de) 2003-12-11 2005-07-14 Basf Ag Verfahren zur Herstellung von Astaxanthin- und Canthaxanthin-Vorprodukten

Patent Citations (67)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3206316A (en) * 1960-10-17 1965-09-14 Hoffmann La Roche Water dispersible carotenoid preparations and processes thereof
US3354218A (en) * 1963-05-10 1967-11-21 Hoffmann La Roche Process for preparing 4-(2, 6, 6-trimethyl-4-methoxy-1-cyclohexen-1-yl)-3-buten-2-one
US3755422A (en) * 1970-01-15 1973-08-28 Rhone Poulenc Sa Preparation of carotenoid compounds
US3989757A (en) * 1973-08-29 1976-11-02 Hoffmann-La Roche Inc. Isomerizing cis-carotenoids to all-trans-carotenoids
US4245109A (en) * 1978-06-02 1981-01-13 Hoffmann-La Roche Inc. Process for producing astaxanthin
US4283559A (en) * 1978-06-02 1981-08-11 Hoffmann-La Roche Inc. Process for the manufacture of cyclohexene derivatives
US4435427A (en) * 1980-12-19 1984-03-06 Basf Aktiengesellschaft Stable injectable β-carotene micellar solutions and their preparation
US4585885A (en) * 1982-08-20 1986-04-29 Hoffmann-La Roche Inc. Cyclohexenone derivatives and process for making same
US4952716A (en) * 1987-03-27 1990-08-28 Hoffmann-La Roche Inc. Ethynylcyclohexene compounds
US5227507A (en) * 1987-03-27 1993-07-13 Hoffmann-La Roche Inc. Ethynylcyclohexene compounds and processes for manufacture thereof
US5364563A (en) * 1989-07-25 1994-11-15 Hoffmann-La Roche Inc. Powdered aqueous carotenoid dispersions
US5871766A (en) * 1990-10-01 1999-02-16 Brigham And Women's Hospital Beta-carotene vitamin E therapy for inhibition of major vascular events
US5422247A (en) * 1992-03-27 1995-06-06 Universal Foods Corporation Blakeslea trispora mated culture capable of increased beta-carotene production
US5328845A (en) * 1992-03-27 1994-07-12 Universal Foods Corporation Fungal negative microorganism capable of producing high levels of beta-carotene
US5612485A (en) * 1992-06-04 1997-03-18 Betatene Ltd Of Cheltenham High cis beta-carotene composition
US5310554A (en) * 1992-10-27 1994-05-10 Natural Carotene Corporation High purity beta-carotene
US5455362A (en) * 1993-07-05 1995-10-03 Basf Aktiengesellschaft Preparation of astaxanthin novel intermediates therefor and the preparation thereof
US5492701A (en) * 1993-07-08 1996-02-20 Rhone-Poulenc Nutrition Animale Process for the preparation of spherules
US5607839A (en) * 1993-07-22 1997-03-04 Nippon Oil Company, Ltd. Bacteria belonging to new genus process for production of carotenoids using same
US5536504A (en) * 1993-11-19 1996-07-16 Marigen S.A. Ultramicroemulsions from spontaneously dispersible concentrates containing xanthophyll esters and having antitumor activity
US5543559A (en) * 1994-07-07 1996-08-06 Hoffman-La Roche Inc. Process for the enantioselective hydrogenation of ketosiophorone derivatives
US5849345A (en) * 1994-12-21 1998-12-15 Roche Vitamins Inc. Carotenoid ketones and esters
US5654488A (en) * 1995-03-18 1997-08-05 Basf Aktiengesellschaft Preparation of astaxanthin
US6060511A (en) * 1995-10-05 2000-05-09 Gainer; John L. Trans-sodium crocetinate, methods of making and methods of use thereof
US6046181A (en) * 1995-10-17 2000-04-04 Showa Denko K.K. Highly purified tocopheryl phosphate, process for producing the same, analytical method therefor and cosmetic
US5854015A (en) * 1995-10-31 1998-12-29 Applied Food Biotechnology, Inc. Method of making pure 3R-3'R stereoisomer of zeaxanthin for human ingestion
US5858700A (en) * 1997-04-03 1999-01-12 Kemin Foods, Lc Process for the isolation and purification of lycopene crystals
US5876782A (en) * 1997-05-14 1999-03-02 Kemin Industries, Inc. Method for the conversion of xanthophylls in plant material
US6245818B1 (en) * 1997-09-04 2001-06-12 Astacarotene Ab Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases
US5959138A (en) * 1997-11-25 1999-09-28 Industrial Organica S.A. De C.V. Short chain diesters and process for making the same
US6335015B1 (en) * 1997-12-16 2002-01-01 Astacarotene Ab Method of the prophylactic treatment of mastitis
US6827941B1 (en) * 1998-01-21 2004-12-07 Basf Aktiengesellschaft Use of carotenoid aggregates as colorants
US6020003A (en) * 1998-02-23 2000-02-01 Basf Corporation Method of making spray-dried powders with high edible-oil loadings based on non-hydrolyzed gelatin
US6673971B2 (en) * 1999-09-30 2004-01-06 Basf Aktiengesellschaft Preparation of 1,1,4,4-tetramethoxy-2-butene
US20040049082A1 (en) * 2001-01-26 2004-03-11 Christoph Wegner Thermal isomerizaton of lycopene
US6540654B2 (en) * 2001-02-23 2003-04-01 Luis W. Levy Carotenoid esters
US6610892B2 (en) * 2001-03-12 2003-08-26 Basf Aktiengesellschaft Process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals
US6747177B2 (en) * 2001-09-13 2004-06-08 Basf Aktiengesellschaft Process for the preparation of meso-zeaxanthin
US20030143660A1 (en) * 2001-11-20 2003-07-31 Qiong Cheng Method for production of asymmetric carotenoids
US20050065096A1 (en) * 2002-07-29 2005-03-24 Lockwood Samuel Fournier Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050075337A1 (en) * 2002-07-29 2005-04-07 Lockwood Samuel Fournier Pharmaceutical compositions including carotenoid analogs or derivatives for the inhabition and amelioration of disease
US20050009930A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling connexin 43 expression
US20050009758A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050009788A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling connexin 43 expression
US20050026874A1 (en) * 2002-07-29 2005-02-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease
US20050037995A1 (en) * 2002-07-29 2005-02-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US20050049248A1 (en) * 2002-07-29 2005-03-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for controlling C-reactive protein levels
US20050059635A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling C-reactive protein levels
US20050059659A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling C-reactive protein levels
US20050065097A1 (en) * 2002-07-29 2005-03-24 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US20040162329A1 (en) * 2002-07-29 2004-08-19 Lockwood Samuel Fournier Structural carotenoid analogs for the inhibition and amelioration of disease
US20050075316A1 (en) * 2002-07-29 2005-04-07 Lockwood Samuel Fournier Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease
US20050004235A1 (en) * 2002-07-29 2005-01-06 Lockwood Samuel Fournier Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease
US20050090469A1 (en) * 2002-07-29 2005-04-28 Lockwood Samuel F. Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease
US20050113372A1 (en) * 2002-07-29 2005-05-26 Lockwood Samuel F. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US20050143475A1 (en) * 2002-07-29 2005-06-30 Lockwood Samuel F. Carotenoid analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US20050148517A1 (en) * 2002-07-29 2005-07-07 Lockwood Samuel F. Carotenoid ether analogs or derivatives for controlling connexin 43 expression
US20060229446A1 (en) * 2002-07-29 2006-10-12 Hawaii Biotech, Inc. Structural carotenoid analogs for the inhibition and amelioration of disease
US20060058269A1 (en) * 2004-04-14 2006-03-16 Lockwood Samuel F Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US20050261254A1 (en) * 2004-04-14 2005-11-24 Lockwood Samuel F Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US20060088905A1 (en) * 2004-10-01 2006-04-27 Lockwood Samuel F Methods for the synthesis of zeazanthin
US20060088904A1 (en) * 2004-10-01 2006-04-27 Lockwood Samuel F Methods for the synthesis of astaxanthin
US20060111580A1 (en) * 2004-10-01 2006-05-25 Lockwood Samuel F Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids
US20060155150A1 (en) * 2004-10-01 2006-07-13 Lockwood Samuel F Methods for the synthesis of lutein
US20060167319A1 (en) * 2004-10-01 2006-07-27 Lockwood Samuel F Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids
US20060183947A1 (en) * 2004-10-01 2006-08-17 Lockwood Samuel F Methods for the synthesis of astaxanthin
US20060183185A1 (en) * 2004-10-01 2006-08-17 Lockwood Samuel F Method for the synthesis of astaxanthin

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7723327B2 (en) 2002-07-29 2010-05-25 Cardax Pharmaceuticals, Inc. Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease
US20050037995A1 (en) * 2002-07-29 2005-02-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US20050065096A1 (en) * 2002-07-29 2005-03-24 Lockwood Samuel Fournier Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050090469A1 (en) * 2002-07-29 2005-04-28 Lockwood Samuel F. Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease
US20050113372A1 (en) * 2002-07-29 2005-05-26 Lockwood Samuel F. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US20050009930A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling connexin 43 expression
US7763649B2 (en) 2002-07-29 2010-07-27 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for controlling connexin 43 expression
US20060088905A1 (en) * 2004-10-01 2006-04-27 Lockwood Samuel F Methods for the synthesis of zeazanthin
US20060088904A1 (en) * 2004-10-01 2006-04-27 Lockwood Samuel F Methods for the synthesis of astaxanthin
US20060167319A1 (en) * 2004-10-01 2006-07-27 Lockwood Samuel F Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids
US20060183185A1 (en) * 2004-10-01 2006-08-17 Lockwood Samuel F Method for the synthesis of astaxanthin
US20060183947A1 (en) * 2004-10-01 2006-08-17 Lockwood Samuel F Methods for the synthesis of astaxanthin
US7247752B2 (en) 2004-10-01 2007-07-24 Cardax Pharmaceuticals, Inc. Methods for the synthesis of astaxanthin
US20060155150A1 (en) * 2004-10-01 2006-07-13 Lockwood Samuel F Methods for the synthesis of lutein
US20060111580A1 (en) * 2004-10-01 2006-05-25 Lockwood Samuel F Methods for the synthesis of chiral dihydroxy ketone intermediates useful for the chiral synthesis of carotenoids
US20090099061A1 (en) * 2006-01-27 2009-04-16 Foss Bente J Synthesis of carotenoid analogs or derivatives with improved antioxidant characteristics
US20090124574A1 (en) * 2007-03-23 2009-05-14 Lockwood Samuel F Carotenoid analogs and derivatives for the prevention of platelet aggregation
US8063101B2 (en) 2007-03-23 2011-11-22 Cardax Pharmaceuticals, Inc. Carotenoid analogs and derivatives for the prevention of platelet aggregation
WO2016007587A3 (en) * 2014-07-08 2016-04-07 Valent Biosciences Corporation 3'-substituted-abscisic acid derivatives
US9781930B2 (en) 2014-07-08 2017-10-10 Valent Biosciences Llc 3′-substituted-abscisic acid derivatives
RU2688347C2 (ru) * 2014-07-08 2019-05-21 Вейлент Биосайенс Корпорейшн 3'-замещаемые производные абсцизовой кислоты
US10299476B2 (en) 2014-07-08 2019-05-28 Valent Biosciences Llc 3′-substituted-abscisic acid derivatives

Also Published As

Publication number Publication date
WO2006039685A2 (en) 2006-04-13
US20060167319A1 (en) 2006-07-27
US20060088904A1 (en) 2006-04-27
US20060088905A1 (en) 2006-04-27
US20060155150A1 (en) 2006-07-13
US20060183185A1 (en) 2006-08-17
US20060111580A1 (en) 2006-05-25
WO2006039685A3 (en) 2007-01-04
US20060183947A1 (en) 2006-08-17
US7247752B2 (en) 2007-07-24

Similar Documents

Publication Publication Date Title
US7247752B2 (en) Methods for the synthesis of astaxanthin
Shen et al. A novel and practical synthetic route for the total synthesis of lycopene
US20080221377A1 (en) Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
US6201155B1 (en) Process for making 4,4′-diketo-carotenoids
US7435861B2 (en) Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
US3558712A (en) Method for the synthesis of zeaxanthins,xanthophylis,and 3-oxo-beta carotene
EP0461653B1 (en) Process for producing beta-carotene, and intermediate compounds useful for the process
JPH1059894A (ja) ポリエンエステル及びポリエン酸の製造方法
EP2109597A1 (en) Process for preparing dienones
JP3961136B2 (ja) ポリエンアルデヒドの製造
US5237102A (en) Sulfone aldehydes useful for producing β-carotene
US5952519A (en) C-15 phosphonate reagent compositions for the manufacture of compounds such as canthaxanthin and methods of synthesizing the same
JP3961073B2 (ja) ポリエン（ジ）アルデヒドの製造方法
Oritani et al. Syntheses of pentadienoic acids structurally related to abscisic acid
Shikichi et al. Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6, 14-Dimethyl-2-octadecanone, Sex Pheromone Components of the Lyclene dharma dharma Moth, from the Enantiomers of Citronellal
Rivas et al. Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′, 8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
JP2506495B2 (ja) β―カロチンの製造方法
GB2123824A (en) 4-Methyl-2,3,5,6-tetrafluorobenzyl acetate and a process for its preparation
EP0404672B1 (fr) Nouveaux dérivés terpéniques, leur préparation et leur emploi
US20240116843A1 (en) Process for the preparation of vitamin k2 and novel intermediates
Matsui et al. The synthesis of methyl vitamin A
Pfander et al. Acyclic Carotenoids
Babler et al. A facile route to 3-alkoxy-2-methylpropenals, useful intermediates in the synthesis of carotenoids
Zhu Application of a novel carbonyl ene reaction: Total syntheses of phyllanthocin and chlorovulone II
Jose David et al. Studies On The Synthesis Of Vitamin A And Related Compounds

Legal Events

Date Code Title Description
AS Assignment

Owner name: HAWAII BIOTECH, INC., HAWAII

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LOCKWOOD, SAMUEL F.;TANG, PENG CHO;NADOLSKI, GEOFF;AND OTHERS;REEL/FRAME:017511/0546

Effective date: 20051219

AS Assignment

Owner name: CARDAX PHARMACEUTICALS, INC., HAWAII

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HAWAII BIOTECH, INC.;REEL/FRAME:018504/0990

Effective date: 20060808

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION