CA2617665C - Method for enantioselective hydrogenation of chromenes - Google Patents

Method for enantioselective hydrogenation of chromenes Download PDF

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Publication number
CA2617665C
CA2617665C CA2617665A CA2617665A CA2617665C CA 2617665 C CA2617665 C CA 2617665C CA 2617665 A CA2617665 A CA 2617665A CA 2617665 A CA2617665 A CA 2617665A CA 2617665 C CA2617665 C CA 2617665C
Authority
CA
Canada
Prior art keywords
phenyl
chromene
equol
chroman
formula
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.)
Expired - Fee Related
Application number
CA2617665A
Other languages
English (en)
French (fr)
Other versions
CA2617665A1 (en
Inventor
Kenneth David Reginald Setchell
Victor Dmitrievich Sorokin
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.)
Cincinnati Childrens Hospital Medical Center
Ausio Pharmaceuticals LLC
Original Assignee
Cincinnati Childrens Hospital Medical Center
Girindus America 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 Cincinnati Childrens Hospital Medical Center, Girindus America Inc filed Critical Cincinnati Childrens Hospital Medical Center
Publication of CA2617665A1 publication Critical patent/CA2617665A1/en
Application granted granted Critical
Publication of CA2617665C publication Critical patent/CA2617665C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
    • C07D311/38—2,3-Dihydro derivatives, e.g. isoflavanones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrane Compounds (AREA)
CA2617665A 2005-08-01 2006-08-01 Method for enantioselective hydrogenation of chromenes Expired - Fee Related CA2617665C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/194,280 US7528267B2 (en) 2005-08-01 2005-08-01 Method for enantioselective hydrogenation of chromenes
US11/194,280 2005-08-01
PCT/US2006/029589 WO2007016423A2 (en) 2005-08-01 2006-08-01 Method for enantioselective hydrogenation of chromenes

Publications (2)

Publication Number Publication Date
CA2617665A1 CA2617665A1 (en) 2007-02-08
CA2617665C true CA2617665C (en) 2014-12-02

Family

ID=37695254

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2617665A Expired - Fee Related CA2617665C (en) 2005-08-01 2006-08-01 Method for enantioselective hydrogenation of chromenes

Country Status (8)

Country Link
US (4) US7528267B2 (https=)
EP (1) EP1919887B1 (https=)
JP (1) JP5507081B2 (https=)
CN (3) CN103755675B (https=)
AU (1) AU2006275587B2 (https=)
CA (1) CA2617665C (https=)
DK (1) DK1919887T3 (https=)
WO (1) WO2007016423A2 (https=)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2504682A1 (en) * 2002-10-29 2004-05-13 Colorado State University Research Foundation Use of equol for treating androgen mediated diseases
GB0610804D0 (en) * 2006-05-31 2006-07-12 Portela & Ca Sa New crystal forms
US7714348B2 (en) * 2006-10-06 2010-05-11 Ac-Led Lighting, L.L.C. AC/DC light emitting diodes with integrated protection mechanism
WO2008153158A1 (ja) * 2007-06-13 2008-12-18 Otsuka Pharmaceutical Co., Ltd. エクオール含有抽出物及びその製造方法、エクオール抽出方法、並びにエクオールを含む食品
EP2231648A1 (en) * 2007-12-05 2010-09-29 BIAL - Portela & Ca., S.A. New salts and crystal forms
EP2133080A1 (de) 2008-06-13 2009-12-16 Haelan Schweiz GmbH Zusammensetzungen enthaltend Equol
RU2364442C1 (ru) * 2008-06-30 2009-08-20 Государственное образовательное учреждение высшего профессионального образования "Тверской государственный технический университет" Способ приготовления модифицированного платинового катализатора для энантиоселективного гидрирования сложных эфиров альфа-кетокарбоновых кислот
EP2154133A1 (de) 2008-08-14 2010-02-17 System Biologie AG Synthese von Equol
US20110091435A1 (en) * 2008-10-24 2011-04-21 University Of Southern California Phytoestrogenic formulations for alleviation or prevention of hair loss
US7875736B2 (en) * 2009-05-19 2011-01-25 Kaohsiung Medical University Intermediate compounds and processes for the preparation of 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran
US7875735B2 (en) * 2009-05-19 2011-01-25 Kaohsiung Medical University Processes for preparing isoflavonoids using 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran as a starting material
WO2011034126A1 (ja) * 2009-09-18 2011-03-24 不二製油株式会社 エクオールの不斉合成法
CN102633763B (zh) * 2012-04-11 2014-02-26 黑龙江大学 一种(s)-雌马酚的制备方法
WO2015117202A1 (en) 2014-02-07 2015-08-13 Novogen Limited Functionalised benzopyran compounds and use thereof
JP6744860B2 (ja) * 2014-09-10 2020-08-19 システム バイオロジー アーゲー イソフラバンおよびその中間体の合成
JP2017531025A (ja) * 2014-10-14 2017-10-19 ジャクソン，リチャード・エル Ｓ−エクオールの無水結晶形
US10391079B2 (en) 2016-07-26 2019-08-27 Ausio Pharmaceuticals, Llc Methods of diagnosing and treating Alzheimer's disease with S-equol
AU2019285640A1 (en) 2018-06-15 2021-01-21 Board Of Regents Of The University Of Texas System Methods of treating and preventing breast cancer with S-equol
WO2019240872A1 (en) 2018-06-15 2019-12-19 The Board Of Regents Of The University Of Texas System Methods of treating and preventing melanoma with s-equol
WO2020071818A1 (ko) * 2018-10-02 2020-04-09 주식회사 글라세움 탄소 이중결합 함유 화합물의 비대칭 수소첨가 반응용 촉매
KR102819124B1 (ko) * 2018-10-02 2025-06-12 주식회사 글라세움 탄소 이중결합 함유 화합물의 비대칭 수소첨가 반응용 촉매

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4264509A (en) * 1977-06-08 1981-04-28 Z-L Limited Partnership Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same
GB8626344D0 (en) * 1986-11-04 1986-12-03 Zyma Sa Bicyclic compounds
AUPO203996A0 (en) * 1996-08-30 1996-09-26 Novogen Research Pty Ltd Therapeutic uses
KR20000057548A (ko) * 1996-12-13 2000-09-25 알프레드 엘. 미첼슨 광학적 전송물질 및 결합재
DE69833365T2 (de) * 1997-03-06 2006-09-28 Mitsui Chemicals, Inc. Verfahren zur herstellung optisch aktiver amine
AUPP868599A0 (en) * 1999-02-15 1999-03-11 Novogen Research Pty Ltd Production of isoflavone derivatives
US6576772B1 (en) * 1999-11-10 2003-06-10 The Penn State Research Foundation Chiral phosphines, transition metal complexes thereof and uses thereof in asymmetric reactions
SE9904850D0 (sv) * 1999-12-30 1999-12-30 Pharmacia & Upjohn Ab Novel process and intermediates
DE10044091A1 (de) * 2000-09-07 2002-04-04 Merck Patent Gmbh Chromanonderivate
ATE294806T1 (de) * 2000-09-21 2005-05-15 Solvias Ag Phosphinite-oxazoline und metallkomplexe
WO2003023056A2 (en) 2001-09-12 2003-03-20 F. Hoffmann-La Roche Ag Specific markers for multiple sclerosis
EP1545206B1 (en) * 2002-07-24 2020-03-04 Children's Hospital Medical Center Compositions and products containing enantiomeric equol, and methods for their making
DE10237648A1 (de) 2002-08-13 2004-02-26 Behr Gmbh & Co. Wärmeübertrager
CA2504682A1 (en) 2002-10-29 2004-05-13 Colorado State University Research Foundation Use of equol for treating androgen mediated diseases
AU2002952453A0 (en) 2002-11-01 2002-11-21 Novogen Research Pty Ltd Aminated isoflavonoid derivatives and uses thereof
PL377427A1 (pl) * 2002-12-19 2006-02-06 Pharmacia Corporation Sposoby i kompozycje do leczenia infekcji wirusem opryszczki z zastosowaniem inhibitorów selektywnych względem cyklooksygenazy-2 lub inhibitorów cyklooksygenazy-2 w połączeniu ze środkami przeciwwirusowymi
ITMI20031354A1 (it) 2003-07-02 2005-01-03 Istituto Di Chimica Biomolecolare D El Cnr Sezione Sintesis enantioselettiva di composti enantiomericamente arricchiti.

Also Published As

Publication number Publication date
CN101535286A (zh) 2009-09-16
US20120004427A1 (en) 2012-01-05
US7528267B2 (en) 2009-05-05
EP1919887A4 (en) 2011-01-19
WO2007016423A3 (en) 2009-04-30
CN103641808A (zh) 2014-03-19
AU2006275587A1 (en) 2007-02-08
JP2009503079A (ja) 2009-01-29
US7960573B2 (en) 2011-06-14
DK1919887T3 (en) 2015-05-26
JP5507081B2 (ja) 2014-05-28
CN103755675A (zh) 2014-04-30
AU2006275587B2 (en) 2012-09-13
US8716497B2 (en) 2014-05-06
WO2007016423A2 (en) 2007-02-08
EP1919887B1 (en) 2015-02-18
CN101535286B (zh) 2014-05-07
US20070027329A1 (en) 2007-02-01
US20100069653A1 (en) 2010-03-18
US20130116450A1 (en) 2013-05-09
US8263790B2 (en) 2012-09-11
CA2617665A1 (en) 2007-02-08
CN103755675B (zh) 2015-11-18
EP1919887A2 (en) 2008-05-14
CN103641808B (zh) 2016-04-20

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Effective date: 20220301

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