WO2006039685A2 - Methods for synthesis of chiral intermediates of carotenoids, carotenoid analogs, and carotenoid derivatives - Google Patents

Methods for synthesis of chiral intermediates of carotenoids, carotenoid analogs, and carotenoid derivatives Download PDF

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Publication number
WO2006039685A2
WO2006039685A2 PCT/US2005/035599 US2005035599W WO2006039685A2 WO 2006039685 A2 WO2006039685 A2 WO 2006039685A2 US 2005035599 W US2005035599 W US 2005035599W WO 2006039685 A2 WO2006039685 A2 WO 2006039685A2
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Prior art keywords
optically active
compound
alkyl
aryl
chiral catalyst
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PCT/US2005/035599
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English (en)
French (fr)
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WO2006039685A3 (en
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Samuel F. Lockwood
Peng Cho Tang
Geoff Nadolski
Zhiqiang Fang
Yishu Du
Min Yang
William Geiss
Richard Williams
William Burdick
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Hawaii Biotech, Inc.
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Publication of WO2006039685A2 publication Critical patent/WO2006039685A2/en
Publication of WO2006039685A3 publication Critical patent/WO2006039685A3/en

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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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PCT/US2005/035599 2004-10-01 2005-10-03 Methods for synthesis of chiral intermediates of carotenoids, carotenoid analogs, and carotenoid derivatives WO2006039685A2 (en)

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
US61503204P 2004-10-01 2004-10-01
US60/615,032 2004-10-01
US67595705P 2005-04-29 2005-04-29
US60/675,957 2005-04-29
US69151805P 2005-06-17 2005-06-17
US60/691,518 2005-06-17
US69268205P 2005-06-21 2005-06-21
US60/692,682 2005-06-21
US69965305P 2005-07-15 2005-07-15
US60/699,653 2005-07-15
US70238005P 2005-07-26 2005-07-26
US60/702,380 2005-07-26
US71235005P 2005-08-30 2005-08-30
US60/712,350 2005-08-30

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006119125A2 (en) * 2005-04-29 2006-11-09 Cardax Pharmaceuticals, Inc. Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
US7247752B2 (en) 2004-10-01 2007-07-24 Cardax Pharmaceuticals, Inc. Methods for the synthesis of astaxanthin
WO2007147163A2 (en) * 2006-06-16 2007-12-21 Cardax Pharmaceuticals, Inc. Compositions comprising carotenoid analogs or derivatives and methods for synthesis
WO2008116714A1 (de) * 2007-03-28 2008-10-02 Basf Se Verfahren zur enantioselektiven herstellung von optisch aktiven 4-hydroxy-2,6,6-trimethyl-cyclohex-2-enon-derivaten
EP2130833A1 (en) 2008-06-05 2009-12-09 DSM IP Assets B.V. Process for the preparation of zeacarotenes
US7919527B2 (en) 2002-02-25 2011-04-05 Diffusion Pharmaceuticals Llc Bipolar trans carotenoid salts and their uses
US8030350B2 (en) 2005-02-24 2011-10-04 Diffusion Pharmaceuticals Llc Trans carotenoids, their synthesis, formulation and uses
US8206751B2 (en) 2007-10-31 2012-06-26 Diffusion Pharmaceuticals Llc Class of therapeutics that enhance small molecule diffusion
US8269027B2 (en) 2002-02-25 2012-09-18 Diffusion Pharmaceuticals Llc Bipolar trans carotenoid salts and their uses
CN105541573A (zh) * 2016-01-19 2016-05-04 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
CN106795109A (zh) * 2014-08-12 2017-05-31 巴斯夫欧洲公司 用于由虾红素制备虾青素的方法
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
WO2018114732A1 (en) 2016-12-19 2018-06-28 Basf Se Process for preparing (4s)- or (4r)-3,4-dihydroxy-2,6,6-trimethylcyclohex-2-enone
US10016384B2 (en) 2010-06-02 2018-07-10 Diffusion Pharmaceuticals Llc Oral formulations of bipolar trans carotenoids
US10130689B2 (en) 2009-06-22 2018-11-20 Diffusion Pharmaceuticals Llc Diffusion enhancing compounds and their use alone or with thrombolytics
US11185523B2 (en) 2016-03-24 2021-11-30 Diffusion Pharmaceuticals Llc Use of bipolar trans carotenoids with chemotherapy and radiotherapy for treatment of cancer

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2495167C (en) * 2002-07-29 2018-08-21 Hawaii Biotech, Inc. Structural carotenoid analogs for the inhibition and amelioration of disease
US7375133B2 (en) * 2002-07-29 2008-05-20 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
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
US20050059635A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling C-reactive protein levels
US7763649B2 (en) * 2002-07-29 2010-07-27 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for controlling connexin 43 expression
US7521584B2 (en) * 2002-07-29 2009-04-21 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US7723327B2 (en) * 2002-07-29 2010-05-25 Cardax Pharmaceuticals, Inc. Carotenoid ester 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
US20090099061A1 (en) * 2006-01-27 2009-04-16 Foss Bente J Synthesis of carotenoid analogs or derivatives with improved antioxidant characteristics
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
US8063101B2 (en) * 2007-03-23 2011-11-22 Cardax Pharmaceuticals, Inc. Carotenoid analogs and derivatives for the prevention of platelet aggregation
US9238043B2 (en) 2009-07-23 2016-01-19 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using algae based oils
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
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
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
US9399047B2 (en) 2009-07-23 2016-07-26 U.S. Nutraceuticals, LLC Composition and method to alleviate joint pain using phospholipids and roe extract
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
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
WO2016007587A2 (en) 2014-07-08 2016-01-14 Valent Biosciences Corporation 3'-substituted-abscisic acid derivatives
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
WO2016023772A1 (de) 2014-08-12 2016-02-18 Basf Se Verfahren zur herstellung zyklischer alpha-ketoalkohole aus zyklischen alpha-ketoenolen
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
CN110088094A (zh) * 2016-12-19 2019-08-02 巴斯夫欧洲公司 制备立体异构纯c9-缩醛的方法
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

Family Cites Families (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH420822A (de) * 1960-10-17 1966-09-15 Hoffmann La Roche Wasserdispergierbare Carotinoidzubereitung
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
FR2076448A5 (US20060178538A1-20060810-C00127.png) * 1970-01-15 1971-10-15 Rhone Poulenc Sa
US3989757A (en) * 1973-08-29 1976-11-02 Hoffmann-La Roche Inc. Isomerizing cis-carotenoids to all-trans-carotenoids
DE2965093D1 (en) * 1978-06-02 1983-05-05 Hoffmann La Roche Derivatives of cyclohexene, process for their peparation, as well as their uses
DE2964401D1 (en) * 1978-06-02 1983-02-03 Hoffmann La Roche Process for the preparation of cyclohexenyl derivatives, and intermediates produced in the synthesis
DE3048000A1 (de) * 1980-12-19 1982-07-15 Basf Ag Stabile injizierbare (beta)-carotin-solubilisate und verfahren zu ihrer herstellung
ATE13876T1 (de) 1982-01-28 1985-07-15 Hoffmann La Roche Verfahren zur herstellung von cycloalkenonderivaten.
DE3377127D1 (en) * 1982-08-20 1988-07-28 Hoffmann La Roche Process for the preparation of astaxanthine and intermediates in the astaxanthine synthesis
DK171297B1 (da) * 1987-03-27 1996-08-26 Hoffmann La Roche Fremgangsmåde til fremstilling af cyclohexenderivater som mellemprodukter til fremstilling af zeaxanthin samt cyclohexenderivater
US5227507A (en) * 1987-03-27 1993-07-13 Hoffmann-La Roche Inc. Ethynylcyclohexene compounds and processes for manufacture thereof
DE59003205D1 (de) * 1989-07-25 1993-12-02 Hoffmann La Roche Verfahren zur Herstellung von Carotinoidpräparaten.
AU660630B2 (en) * 1990-10-01 1995-07-06 Brigham And Women's Hospital Beta-carotene and vitamin E therapy for inhibition of major vascular events
US5328845A (en) * 1992-03-27 1994-07-12 Universal Foods Corporation Fungal negative microorganism capable of producing high levels of beta-carotene
IL104736A0 (en) * 1992-03-27 1993-06-10 Zeagen Inc Method for producing beta-carotene using a fungal mated culture
DE69327100T2 (de) * 1992-06-04 2000-04-13 Betatene Pty Ltd Gemisch mit hohem gehalt an cis beta-carotin
US5310554A (en) * 1992-10-27 1994-05-10 Natural Carotene Corporation High purity beta-carotene
DE4322277A1 (de) * 1993-07-05 1995-01-12 Basf Ag Verbessertes Verfahren zur Herstellung von Astaxanthin, neue Zwischenprodukte hierfür sowie ein Verfahren zu deren Herstellung
FR2707184B1 (fr) * 1993-07-08 1995-08-11 Rhone Poulenc Nutrition Animal Procédé de préparation de sphérules contenant un principe actif alimentaire ou pharmaceutique.
US5607839A (en) * 1993-07-22 1997-03-04 Nippon Oil Company, Ltd. Bacteria belonging to new genus process for production of carotenoids using same
CH685189A5 (de) * 1993-11-19 1995-04-28 Marigen Sa Ultramikroemulsionen aus spontan dispergierbaren Konzentraten mit antitumoral wirksamen Xanthophyll-Estern.
JPH07300421A (ja) 1994-04-28 1995-11-14 Itano Reitou Kk 抗炎症剤
US5543559A (en) * 1994-07-07 1996-08-06 Hoffman-La Roche Inc. Process for the enantioselective hydrogenation of ketosiophorone derivatives
JPH0873312A (ja) 1994-09-02 1996-03-19 Noevir Co Ltd 皮膚外用剤
DE69511515T2 (de) * 1994-12-21 2000-01-20 Hoffmann La Roche Carotenoide Ketone und Ester
DE19509955A1 (de) * 1995-03-18 1996-09-19 Basf Ag Verfahren zur Herstellung von Astaxanthin
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
US6060511A (en) * 1995-10-05 2000-05-09 Gainer; John L. Trans-sodium crocetinate, methods of making and methods of use thereof
JP4115524B2 (ja) * 1995-10-17 2008-07-09 昭和電工株式会社 高純度トコフェロールリン酸エステル類、その製造方法、その分析方法並びに化粧料
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
JPH09202730A (ja) 1996-01-24 1997-08-05 Nippon Mektron Ltd 発ガン抑制作用剤
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
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
SE512531C2 (sv) * 1997-09-04 2000-03-27 Astacarotene Ab Användning av åtminstone en typ av xantofyller för framställning av ett läkemedel för profylaktisk och/eller terapeutisk förbättring av muskelfunktionsdurationen hos däggdjur och/eller behandling av muskelstörningar eller - sjukdomar hos däggdjur
US5959138A (en) 1997-11-25 1999-09-28 Industrial Organica S.A. De C.V. Short chain diesters and process for making the same
SE511237C2 (sv) * 1997-12-16 1999-08-30 Astacarotene Ab Användning av åtminstone en typ av xantofyller för framställning av ett humant eller verinärmedicinskt läkemedel för profylaktisk behandling av mastit hos däggdjursmammor
DE19802134A1 (de) * 1998-01-21 1999-07-22 Basf Ag Verwendung von Carotinoid-Aggregaten als Färbemittel
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
DE19946816A1 (de) * 1999-09-30 2001-04-05 Basf Ag Verfahren zur Herstellung von 1,1,4,4-Tetramethoxybuten-2
DE10103708A1 (de) * 2001-01-26 2002-08-01 Basf Ag Thermische Isomerisierung von Lycopin
ES2300441T3 (es) 2001-02-23 2008-06-16 Luis W. Levy Esteres de carotenoides novedosos.
DE10112067A1 (de) * 2001-03-12 2002-09-19 Basf Ag Verfahren zur Herstellung von 2,7-Dimethyl-2,4,6-octarienal-monoacetalen
DE10145223A1 (de) * 2001-09-13 2003-04-03 Basf Ag Verfahren zur Herstellung von meso-Zeaxanthin
US7063955B2 (en) * 2001-11-20 2006-06-20 E. I. Du Pont De Nemours And Company Method for production of asymmetric carotenoids
EP1474388B2 (en) 2002-02-06 2013-03-06 DSM IP Assets B.V. Astaxanthin esters
US7320997B2 (en) * 2002-07-29 2008-01-22 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ester 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
US7345091B2 (en) * 2002-07-29 2008-03-18 Cardax Pharmaceuticals, Inc. Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
CA2495167C (en) * 2002-07-29 2018-08-21 Hawaii Biotech, Inc. Structural carotenoid analogs for the inhibition and amelioration of disease
US7521584B2 (en) * 2002-07-29 2009-04-21 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US7763649B2 (en) 2002-07-29 2010-07-27 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for controlling connexin 43 expression
US20050059635A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid ester 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
US20050026874A1 (en) * 2002-07-29 2005-02-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease
US20050009788A1 (en) * 2002-07-29 2005-01-13 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling connexin 43 expression
US7375133B2 (en) * 2002-07-29 2008-05-20 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050059659A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling C-reactive protein levels
US20050049248A1 (en) 2002-07-29 2005-03-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for controlling C-reactive protein levels
US7723327B2 (en) * 2002-07-29 2010-05-25 Cardax Pharmaceuticals, Inc. Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease
US20050004235A1 (en) * 2002-07-29 2005-01-06 Lockwood Samuel Fournier Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease
DE10358003A1 (de) 2003-12-11 2005-07-14 Basf Ag Verfahren zur Herstellung von Astaxanthin- und Canthaxanthin-Vorprodukten
WO2005102356A1 (en) 2004-04-14 2005-11-03 Hawaii Biotech, Inc. 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
US7247752B2 (en) * 2004-10-01 2007-07-24 Cardax Pharmaceuticals, Inc. Methods for the synthesis of astaxanthin

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
D. LIOTTA ET AL.: "Pyridinium Dichromate-Induced 1,3-oxidative Rearrangements of Enynols" TETRAHEDRON LETT., vol. 28, no. 10, 1987, pages 1069-1072, XP002393247 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002393250 Database accession no. Reaction ID 4538814 & SRIKRISHNA ADUSUMILLI ET AL.: J. CHEM. SOC. PERKIN TRANS 1, 11, 1996, pages 1305-1312, *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002393251 Database accession no. RN 3699622 & TAKAHASHI, SHUNYA ET AL.: AGRIC. BIOL. CHEM., vol. 51, no. 4, 1987, pages 1143-1148, *
HAUGAN J A ET AL: "TOTAL SYNTHESIS OF C31-METHYL KETONE APOCAROTENOIDS 3. ON THE STRUCTURE OF HOPKINSIAXANTHIN: FIRST TOTAL SYNTHESIS OF (ALL-E)-(3S)- AND (9Z)-(3S)-7'-APOHOPKINSIAXANTHIN" ACTA CHEMICA SCANDINAVICA, MUNKSGAARD, COPENHAGEN, DK, vol. 51, no. 12, 1997, pages 1201-1216, XP009063786 ISSN: 0904-213X *
HENNIG M ET AL: "Synthesis of (R)- and (S)-4-hydroxyisophorone by ruthenium-catalyzed asymmetric transfer hydrogenation of ketoisophorone" TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 11, no. 9, May 2000 (2000-05), pages 1849-1858, XP004205809 ISSN: 0957-4166 cited in the application *
KIENZLE F ET AL: "SYNTHESE VON OPTISCH AKTIVEN, NATUERLICHEN CAROTINOIDEN UND STRUKTURELL VERWANDTEN NATURPRODUKTEN. II. SYNTHESE VON (3S,3'S)-ASTAXANTHIN" HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA. BASEL, CH, vol. 61, no. 7, 1978, pages 2609-2615, XP009048844 ISSN: 0018-019X *
TANAKA A ET AL: "Lipase-Catalyzed Asymmetric Synthesis of (R)- and (S)-4-tert-Butyldimethylsilyloxy-2,6,6-tri methyl-2-cyclohexenone and Their Dihydro Derivatives" TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 6, no. 6, June 1995 (1995-06), pages 1273-1278, XP004048170 ISSN: 0957-4166 *
VON ARX, M. ET AL: "Unprecedented selectivity behavior in the hydrogenation of an .alpha.,.beta.-unsaturated ketone: hydrogenation of ketoisophorone over alumina-supported Pt and Pd" JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 148, no. 1-2, 1999, pages 275-283, XP002374375 *
WIDMER E ET AL: "TECHNISCHE VERFAHREN ZUR SYNTHESE VON CAROTINOIDEN UND VERWANDTEN VERBINDUNGEN AUS 6-OXO-ISOPHORON. II. EIN NEUES KONZEPT FUER DIE SYNTHESE VON (3RS,3'RS)-ASTAXANTHIN" HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA. BASEL, CH, vol. 64, no. 239, 1981, pages 2436-2446, XP009063882 ISSN: 0018-019X cited in the application *
WIDMER E ET AL: "TECHNISCHE VERFAHREN ZUR SYNTHESE VON CAROTINOIDEN UND VERWANDTEN VERBINDUNGEN AUS OXO-ISOPHORON. I. MODIFIZIERUNG DER KIENZLE-MAYER-SYNTHESE VON (3S,3'S)-ASTAXANTHIN" HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA. BASEL, CH, vol. 64, no. 237, 1981, pages 2405-2418, XP009063877 ISSN: 0018-019X *
ZELL R ET AL: "TECHNISCHE VERFAHREN ZUR SYNTHESE VON CAROTINOIDEN UND VERWANDTEN VERBINDUNGEN AUS 6-OXO-ISOPHORON. III. EIN NEUES KONZEPT FUER DIE SYNTHESE DER ENANTIOMEREN ASTAXANTHINE" HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA. BASEL, CH, vol. 64, no. 7, 1981, pages 2447-2462, XP001202861 ISSN: 0018-019X cited in the application *

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