CA2920346A1 - Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside - Google Patents

Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside Download PDF

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Publication number
CA2920346A1
CA2920346A1 CA2920346A CA2920346A CA2920346A1 CA 2920346 A1 CA2920346 A1 CA 2920346A1 CA 2920346 A CA2920346 A CA 2920346A CA 2920346 A CA2920346 A CA 2920346A CA 2920346 A1 CA2920346 A1 CA 2920346A1
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CA
Canada
Prior art keywords
compound
formula
reacting
prepare
carried out
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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
CA2920346A
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English (en)
French (fr)
Inventor
Melpo Christofidou-Solomidou
Kyriacos C. Nicolaou
Roman A. Valiulin
Nicholas SIMMONS
Philipp M. Heretsch
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.)
Scripps Research Institute
University of Pennsylvania Penn
Original Assignee
Scripps Research Institute
University of Pennsylvania Penn
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Filing date
Publication date
Application filed by Scripps Research Institute, University of Pennsylvania Penn filed Critical Scripps Research Institute
Publication of CA2920346A1 publication Critical patent/CA2920346A1/en
Abandoned legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18Acyclic radicals, substituted by carbocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/18Antioxidants, e.g. antiradicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00General protective or antinoxious agents
    • A61P39/06Free radical scavengers or antioxidants
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/18Preparation of ethers by reactions not forming ether-oxygen bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Toxicology (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
CA2920346A 2013-06-10 2014-06-10 Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside Abandoned CA2920346A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361833258P 2013-06-10 2013-06-10
US61/833,258 2013-06-10
PCT/US2014/041636 WO2014200964A1 (en) 2013-06-10 2014-06-10 Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside

Publications (1)

Publication Number Publication Date
CA2920346A1 true CA2920346A1 (en) 2014-12-18

Family

ID=52022698

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2920346A Abandoned CA2920346A1 (en) 2013-06-10 2014-06-10 Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside

Country Status (21)

Country Link
US (2) US10030040B2 (https=)
EP (2) EP3488697A1 (https=)
JP (3) JP6321788B2 (https=)
KR (1) KR102270124B1 (https=)
CN (2) CN107955046A (https=)
AU (1) AU2014278362B2 (https=)
CA (1) CA2920346A1 (https=)
CY (1) CY1120759T1 (https=)
DK (1) DK3007557T3 (https=)
ES (1) ES2691845T3 (https=)
HR (1) HRP20181663T1 (https=)
HU (1) HUE040022T2 (https=)
IL (2) IL243029B (https=)
LT (1) LT3007557T (https=)
PL (1) PL3007557T3 (https=)
PT (1) PT3007557T (https=)
RS (1) RS57846B1 (https=)
SI (1) SI3007557T1 (https=)
SM (1) SMT201800575T1 (https=)
TR (1) TR201815423T4 (https=)
WO (1) WO2014200964A1 (https=)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RS57846B1 (sr) 2013-06-10 2018-12-31 Univ Pennsylvania Dobijanje (s,s)-sekoizolaricirezinol diglukozida i (r,r)-sekoizolaricirezinol diglukozida
AU2015266614A1 (en) * 2014-05-30 2016-12-15 The Trustees Of The University Of Pennsylvania Use of secoisolariciresinol diglucosides (SDGs) and related compounds for protection against radiation and chemical damage
US11197876B2 (en) 2014-05-30 2021-12-14 The Trusiees Of The University Of Pennsylvania Effects of LGM2605 on a primate model of asthma
US20170258821A1 (en) 2014-05-30 2017-09-14 The Trustees Of The University Of Pennsylvania USE OF SECOISOLARICIRESINOL DIGLUCOSIDES (SDGs) AND RELATED COMPOUNDS FOR PROTECTION AGAINST RADIATION AND CHEMICAL DAMAGE
AU2016315952A1 (en) * 2015-09-01 2018-04-05 The Trustees Of The University Of Pennsylvania Use of secoisolariciresinol diglucosides (SDGs) and related compounds for protection against radiation damage
ES2969209T3 (es) 2016-06-07 2024-05-17 Univ Pennsylvania Composiciones y métodos para proteger órganos de lesiones por isquemia/reperfusión asociadas con el trasplante
JP2020523394A (ja) 2017-06-12 2020-08-06 リグナメッド・エルエルシーLignamed,Llc (s,s)−セコイソラリシレシノールジグルコシド及び(r,r)−セコイソラリシレシノールジグルコシドの製造方法
CN110283218A (zh) * 2019-06-24 2019-09-27 暨南大学 提高木酚素油溶性的改性方法
CN111233944B (zh) * 2020-03-25 2023-02-28 宝鸡市辰光生物科技有限公司 一种同时制备分离四种木脂素类成分的高效液相方法

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3065925B2 (ja) * 1996-01-30 2000-07-17 日清製油株式会社 活性酸素種消去剤及び退色防止剤
AU3760699A (en) * 1998-04-24 1999-11-16 Washington State University Research Foundation Recombinant secoisolariciresinol dehydrogenase, and methods of use
FI110868B (fi) 2001-01-22 2003-04-15 Maa Ja Elintarviketalouden Tut Menetelmä sekoisolarisiresinolidiglykosidin (SDG) eristämiseksi ja puhdistamiseksi pellavansiemenistä
US20030060420A1 (en) 2001-09-14 2003-03-27 Rick Heintzman Process for extraction and stabilization of phytoestrogens from flaxseed and product therefrom
DE60333353D1 (de) 2002-04-02 2010-08-26 Lignan Res Llc Verfahren zur wiedergewinnung von secoisolariciresinol diglycosid aus entfetteten flachs-saatgut
JP2006347978A (ja) * 2005-06-17 2006-12-28 Nippon Flour Mills Co Ltd 抗肥満剤及びこれを含む食品並びにペットフード
JP2007308469A (ja) * 2005-11-11 2007-11-29 Nippon Flour Mills Co Ltd リグナンを有効成分とする男性用抗肥満剤
CN100395253C (zh) * 2006-05-12 2008-06-18 中国科学院山西煤炭化学研究所 一种由亚麻籽制备开环异落叶松树脂酚二葡萄糖苷的方法
CN101117641B (zh) * 2007-07-27 2011-05-11 大连医诺生物有限公司 开环异落叶松树脂酚二葡萄糖苷的制备方法
JP2010057367A (ja) 2008-09-01 2010-03-18 Nitto Boseki Co Ltd 魚肉の褐変防止剤および褐変防止方法
CN102050848A (zh) * 2009-11-01 2011-05-11 桂林莱茵生物科技股份有限公司 一种亚麻木酚素的制备方法
ES2362065B1 (es) * 2009-12-15 2012-05-18 Consejo Superior De Investigaciones Cient�?Ficas (Csic) Compuestos con actividad antiinflamatoria.
WO2012021983A1 (en) * 2010-08-20 2012-02-23 Fédération Des Producteurs Acéricoles Du Québec Sugar plant derived by-products and methods of production thereof
CN102558252A (zh) 2010-12-31 2012-07-11 西安天一生物技术有限公司 一种亚麻木酚素的生产工艺
RS57846B1 (sr) * 2013-06-10 2018-12-31 Univ Pennsylvania Dobijanje (s,s)-sekoizolaricirezinol diglukozida i (r,r)-sekoizolaricirezinol diglukozida

Also Published As

Publication number Publication date
HRP20181663T1 (hr) 2018-12-14
US10870670B2 (en) 2020-12-22
EP3007557A1 (en) 2016-04-20
ES2691845T3 (es) 2018-11-28
EP3007557B1 (en) 2018-07-18
WO2014200964A1 (en) 2014-12-18
HK1223792A1 (zh) 2017-08-11
IL269622A (en) 2019-11-28
PL3007557T3 (pl) 2019-04-30
US10030040B2 (en) 2018-07-24
HUE040022T2 (hu) 2019-02-28
IL243029B (en) 2019-09-26
LT3007557T (lt) 2018-11-12
SMT201800575T1 (it) 2019-01-11
PT3007557T (pt) 2018-11-09
CN107955046A (zh) 2018-04-24
DK3007557T3 (en) 2018-11-05
JP2018111721A (ja) 2018-07-19
AU2014278362A1 (en) 2016-02-04
JP2019147803A (ja) 2019-09-05
JP6785335B2 (ja) 2020-11-18
AU2014278362B2 (en) 2017-07-13
CY1120759T1 (el) 2019-12-11
TR201815423T4 (tr) 2018-11-21
KR102270124B1 (ko) 2021-06-25
CN105705018A (zh) 2016-06-22
RS57846B1 (sr) 2018-12-31
US20190062363A1 (en) 2019-02-28
KR20160023770A (ko) 2016-03-03
JP2016521748A (ja) 2016-07-25
JP6513853B2 (ja) 2019-05-15
CN105705018B (zh) 2018-01-12
EP3007557A4 (en) 2017-01-18
US20160137682A1 (en) 2016-05-19
JP6321788B2 (ja) 2018-05-09
SI3007557T1 (sl) 2018-12-31
EP3488697A1 (en) 2019-05-29

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Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20190516

FZDE Discontinued

Effective date: 20230411