CN100341867C - 多酚的合成方法 - Google Patents

多酚的合成方法 Download PDF

Info

Publication number
CN100341867C
CN100341867C CNB988119412A CN98811941A CN100341867C CN 100341867 C CN100341867 C CN 100341867C CN B988119412 A CNB988119412 A CN B988119412A CN 98811941 A CN98811941 A CN 98811941A CN 100341867 C CN100341867 C CN 100341867C
Authority
CN
China
Prior art keywords
substituted
protected
group
polyphenol
proanthocyanidin
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
CNB988119412A
Other languages
English (en)
Chinese (zh)
Other versions
CN1302295A (zh
Inventor
小L·J·罗曼赛克
A·P·科兹科夫斯基
W·特克曼特尔
M·E·利普曼
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.)
Mars Inc
Original Assignee
Mars 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 Mars Inc filed Critical Mars Inc
Publication of CN1302295A publication Critical patent/CN1302295A/zh
Application granted granted Critical
Publication of CN100341867C publication Critical patent/CN100341867C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/06Benzopyran radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic 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
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26Benzo[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
    • C07D311/28Benzo[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 2 only
    • C07D311/322,3-Dihydro derivatives, e.g. flavanones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic 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
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic 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
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Compounds Of Unknown Constitution (AREA)
CNB988119412A 1997-10-09 1998-10-09 多酚的合成方法 Expired - Fee Related CN100341867C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/948,226 US6207842B1 (en) 1997-10-09 1997-10-09 Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives
US08/948,226 1997-10-09

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CNA2007100018908A Division CN101066962A (zh) 1997-10-09 1998-10-09 多酚的合成方法

Publications (2)

Publication Number Publication Date
CN1302295A CN1302295A (zh) 2001-07-04
CN100341867C true CN100341867C (zh) 2007-10-10

Family

ID=25487506

Family Applications (2)

Application Number Title Priority Date Filing Date
CNB988119412A Expired - Fee Related CN100341867C (zh) 1997-10-09 1998-10-09 多酚的合成方法
CNA2007100018908A Pending CN101066962A (zh) 1997-10-09 1998-10-09 多酚的合成方法

Family Applications After (1)

Application Number Title Priority Date Filing Date
CNA2007100018908A Pending CN101066962A (zh) 1997-10-09 1998-10-09 多酚的合成方法

Country Status (13)

Country Link
US (6) US6207842B1 (https=)
EP (1) EP1027345B1 (https=)
JP (1) JP2001519426A (https=)
KR (1) KR100560463B1 (https=)
CN (2) CN100341867C (https=)
AT (1) ATE232857T1 (https=)
AU (1) AU760031B2 (https=)
CA (1) CA2306851A1 (https=)
DE (1) DE69811526T2 (https=)
DK (1) DK1027345T3 (https=)
ES (1) ES2189260T3 (https=)
IL (1) IL135344A (https=)
WO (1) WO1999019319A1 (https=)

Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030017998A1 (en) * 1997-05-16 2003-01-23 Snow Alan D. Proanthocyanidins for the treatment of amyloid and alpha-synuclein diseases
US6207842B1 (en) * 1997-10-09 2001-03-27 Mars Incorporated Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives
US7015338B1 (en) * 1999-04-15 2006-03-21 Mars Incorporated Synthetic methods for preparing procyanidin oligomers
US6562864B1 (en) * 1999-09-02 2003-05-13 Drake Larson Catechin multimers as therapeutic drug delivery agents
US6476241B1 (en) * 2000-09-05 2002-11-05 Mars Incorporated Synthesis of 4α-arylepicatechins
US20070208087A1 (en) 2001-11-02 2007-09-06 Sanders Virginia J Compounds, compositions and methods for the treatment of inflammatory diseases
KR100418390B1 (ko) * 2000-12-11 2004-02-11 김도훈 녹차로부터 추출된 항암효과가 우수한 폴리페놀류 화합물
US7297800B2 (en) * 2001-12-27 2007-11-20 Ajinomoto Co., Inc. Process of producing glutamate derivatives
US7514107B2 (en) 2002-03-21 2009-04-07 Mars, Incorporated Treatment of diseases involving defective gap junctional communication
US7595074B2 (en) * 2002-04-05 2009-09-29 University Of Massachusetts Lowell Polymeric antioxidants
EP1492856A4 (en) * 2002-04-05 2010-11-10 Univ Massachusetts Lowell POLYMER ANTIOXIDANTS
US7067679B2 (en) * 2002-10-02 2006-06-27 Mars, Inc. Synthesis of dimeric, trimeric, tetrameric pentameric, and higher oligomeric epicatechin-derived procyanidins having 4,8-interflavan linkages and their use to inhibit cancer cell growth through cell cycle arrest
AU2002348822A1 (en) * 2002-12-17 2004-07-09 Council Of Scientific And Industrial Research A new antioxidant from natural source
EP1524270B1 (en) * 2003-05-26 2009-08-26 Amino Up Chemical Co. Ltd. Sulfur-containing proanthocyanidin oligomer composition and process for producing the same
JP2007508316A (ja) * 2003-10-10 2007-04-05 マーズ インコーポレイテッド ErbB2キナーゼ過剰発現に関連する病気の治療
CA2575952A1 (en) * 2004-01-21 2005-08-04 University Of Massachusetts Lowell Post-coupling synthetic approach for polymeric antioxidants
EP1742656B1 (en) 2004-03-12 2010-06-16 University Of Georgia Research Foundation, Inc. Novel peanut skin extract as a vaccine adjuvant
RU2007101288A (ru) * 2004-06-14 2008-07-20 Марс Композиции и способы применения димерных дигаллатов
JP2008507613A (ja) * 2004-07-23 2008-03-13 ポルノクス コーポレーション 抗酸化マクロモノマーおよび抗酸化ポリマー、ならびにその作製方法および使用方法
US20060128930A1 (en) * 2004-12-03 2006-06-15 Ashish Dhawan Synthesis of sterically hindered phenol based macromolecular antioxidants
WO2006060803A2 (en) * 2004-12-03 2006-06-08 Polnox Corporation One pot process for making polymeric antioxidants
US7678877B2 (en) * 2004-12-03 2010-03-16 Polnox Corporation Process for the synthesis of polyalkylphenol antioxidants
WO2006060800A1 (en) 2004-12-03 2006-06-08 Polnox Corporation Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers
EP1861484A2 (en) 2005-02-22 2007-12-05 Polnox Corporation Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications
CA2606303A1 (en) 2005-03-25 2006-10-05 Polnox Corporation Alkylated and polymeric macromolecular antioxidants and methods of making and using the same
WO2006116532A2 (en) * 2005-04-28 2006-11-02 University Of Massachusetts Lowell Synthesis of oligo/poly(catechins) and methods of use
AU2006263561A1 (en) * 2005-06-28 2007-01-04 Mars, Incorporated Compositions and methods of use of derivatized flavanols
US20070004796A1 (en) * 2005-06-29 2007-01-04 Romanczyk Leo Jr Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4B,8)-epicatechin or -catechin dimers and their digallates
CN101248057A (zh) * 2005-06-29 2008-08-20 马尔斯公司 (+)-儿茶素、(-)-表儿茶素、(-)-儿茶素、(+)-表儿茶素以及它们的5,7,3',4'-四-o-苄基类似物的制备
CN101300007A (zh) 2005-06-29 2008-11-05 马尔斯公司 诱导周围血管的血管舒张
WO2007003068A1 (fr) * 2005-06-30 2007-01-11 Hangzhou Lixin Biotechnology Co. Ltd. Additif pour nourriture, procédé de préparation de celui-ci et application de celui-ci
EP2258358A3 (en) 2005-08-26 2011-09-07 Braincells, Inc. Neurogenesis with acetylcholinesterase inhibitor
EP1928437A2 (en) 2005-08-26 2008-06-11 Braincells, Inc. Neurogenesis by muscarinic receptor modulation
EP1940389A2 (en) 2005-10-21 2008-07-09 Braincells, Inc. Modulation of neurogenesis by pde inhibition
WO2007050985A2 (en) 2005-10-27 2007-05-03 Polnox Corporation Macromolecular antioxidants based on stξrically hindered phenolic phosphites
US20070106059A1 (en) * 2005-10-27 2007-05-10 Cholli Ashok L Macromolecular antioxidants and polymeric macromolecular antioxidants
EP1966293A1 (en) * 2005-10-27 2008-09-10 Polnox Corporation Stabilized polyolefin compositions
US20070112017A1 (en) 2005-10-31 2007-05-17 Braincells, Inc. Gaba receptor mediated modulation of neurogenesis
WO2007053642A1 (en) * 2005-11-01 2007-05-10 Mars, Incorporated Flavanols and b-type procyanidins and cox-2 expression
US20070161522A1 (en) 2005-12-02 2007-07-12 Cholli Ashok L Lubricant oil compositions
JP2009521475A (ja) 2005-12-23 2009-06-04 マース インコーポレーテッド 皮膚の保護および改善
WO2007084648A2 (en) * 2006-01-20 2007-07-26 Mars, Incorporated Mixed 4→6 procyanidin dimers and their use
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
AU2007249399A1 (en) 2006-05-09 2007-11-22 Braincells, Inc. Neurogenesis by modulating angiotensin
WO2007134077A2 (en) 2006-05-09 2007-11-22 Braincells, Inc. 5 ht receptor mediated neurogenesis
CN101505745A (zh) 2006-06-15 2009-08-12 玛尔斯有限公司 改善认知功能的方法和组合物
WO2008005358A2 (en) 2006-07-06 2008-01-10 Polnox Corporation Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same
CA2657915A1 (en) 2006-07-21 2008-01-24 Mars, Incorporated Improvement of arginase levels/activity
EP2068872A1 (en) * 2006-09-08 2009-06-17 Braincells, Inc. Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en) 2006-09-19 2010-07-22 Braincells, Inc. Modulation of neurogenesis by ppar agents
US7767853B2 (en) 2006-10-20 2010-08-03 Polnox Corporation Antioxidants and methods of making and using the same
JP5160149B2 (ja) * 2007-06-22 2013-03-13 明治薬品株式会社 柿ポリフェノールオリゴマー
JP5295744B2 (ja) * 2008-12-11 2013-09-18 三井農林株式会社 テアシネンシンの製造方法
WO2010099217A1 (en) 2009-02-25 2010-09-02 Braincells, Inc. Modulation of neurogenesis using d-cycloserine combinations
US8916526B2 (en) * 2009-07-31 2014-12-23 National University Corporation Okayama University Flavanone derivative
US8932468B2 (en) * 2010-01-12 2015-01-13 The United States Of America As Represented By The Secretary Of The Army Separation of enzymatically synthesized polyepicatechin via high performance liquid chromatography
US20120238638A1 (en) * 2011-03-18 2012-09-20 Jorma Antero Virtanen Biological biocide additives for polymers
JP5437537B1 (ja) * 2012-10-05 2014-03-12 フジッコ株式会社 低重合度プロアントシアニジンの製法
US9522131B2 (en) 2013-01-11 2016-12-20 Wisconsin Alumni Research Foundation Tannin-containing gastrointestinal formulations and methods of use
WO2015077635A2 (en) 2013-11-22 2015-05-28 Polnox Corporation Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same
US20180251695A1 (en) 2017-03-01 2018-09-06 Polnox Corporation Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same
CN108047271B (zh) * 2017-12-06 2020-05-26 石家庄学院 一种槲皮素二聚体衍生物及其制备方法和应用
CN109503800B (zh) * 2018-10-30 2021-07-09 合肥科天水性科技有限责任公司 一种改性水性聚氨酯及其制备方法
JP7679064B2 (ja) * 2021-06-15 2025-05-19 国立大学法人信州大学 ガレート型エピカテキン重合体又はガレート型エピガロカテキン重合体の製造方法
CN117658967A (zh) * 2023-10-09 2024-03-08 朗华生物科学(深圳)有限公司 一种黄烷-3,4-二醇类衍生物的制备方法
CN117534646B (zh) * 2023-11-20 2025-02-25 朗华生物科学(深圳)有限公司 一种原花青素b2的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1518003A1 (de) * 1964-01-18 1969-01-30 Merck Ag E Verfahren zur Herstellung von substituierten Flavanderivaten
EP0039844A2 (de) * 1977-11-25 1981-11-18 Zyma SA Verfahren zur Herstellung von O-substituierten Derivaten des (+)-Cyanidan-3-ols
CN1221344A (zh) * 1996-04-02 1999-06-30 火星有限公司 可提取物化合物以及其制备方法和用途

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE39844C (de) 1886-09-23 1887-06-22 Black John Melton Neuerung an der Controlb}chse f}r Conducteure.
JPS58154571A (ja) 1982-03-08 1983-09-14 Nippon Shinyaku Co Ltd 新規タンニン
GB2122608B (en) 1982-06-01 1985-10-02 Zyma Sa (+)-cyanidan-3-ol derivatives
JPS61205272A (ja) 1985-03-08 1986-09-11 Tsumura Juntendo Inc 新規なタンニン
US4698360B1 (en) * 1985-04-09 1997-11-04 D Investigations Pharmacologiq Plant extract with a proanthocyanidins content as therapeutic agent having radical scavenger effect and use thereof
JPS631936A (ja) * 1986-06-23 1988-01-06 Asahi Optical Co Ltd 光電変換回路
JPH0231074B2 (ja) * 1986-08-26 1990-07-11 Nippon Shinyaku Co Ltd Shintannin
JPS63214183A (ja) * 1987-03-03 1988-09-06 Mitsui Norin Kk アンジオテンシン1変換酵素阻害剤
EP0472531B1 (fr) * 1989-05-12 1995-08-16 Cariel, Léon Composition a base de proanthocyanidols; leur application pharmacologique
US5358713A (en) * 1990-02-23 1994-10-25 Mitsui Norin Co., Ltd. Method of preventing the transmission of infection caused by methicillin-resistant Staphylococcus aureus
FR2668373B1 (fr) 1990-10-26 1994-04-08 Intertechnique Equipement respiratoire de protection d'equipage d'aeronef.
JP2857646B2 (ja) 1990-11-26 1999-02-17 キッコーマン株式会社 抗変異原性剤
GB9209734D0 (en) * 1992-05-06 1992-06-17 Philips Electronics Uk Ltd An image sensor
JP3139134B2 (ja) * 1992-06-03 2001-02-26 カシオ計算機株式会社 液晶表示装置
JP2821347B2 (ja) * 1993-10-12 1998-11-05 日本電気株式会社 電流制御型発光素子アレイ
JPH07236029A (ja) * 1993-12-29 1995-09-05 Xerox Corp コンパクト・ドキュメント・イメージャ
US5554645A (en) * 1994-10-03 1996-09-10 Mars, Incorporated Antineoplastic cocoa extracts and methods for making and using the same
US5627364A (en) * 1994-10-11 1997-05-06 Tdk Corporation Linear array image sensor with thin-film light emission element light source
US5625210A (en) * 1995-04-13 1997-04-29 Eastman Kodak Company Active pixel sensor integrated with a pinned photodiode
JP3436629B2 (ja) * 1996-01-08 2003-08-11 シャープ株式会社 表示および撮像のための装置
FI102345B1 (fi) * 1996-02-20 1998-11-13 Nokia Telecommunications Oy Menetelmä päätelaitteen nopeuden määrittämiseksi ja vastaanotin
WO1997036597A1 (en) * 1996-04-02 1997-10-09 Mars, Incorporated Cocoa extract compounds and methods for making and using the same
US6188380B1 (en) * 1997-02-03 2001-02-13 Nanao Corporation Photodetector of liquid crystal display and luminance control device using the same
JP3641342B2 (ja) * 1997-03-07 2005-04-20 Tdk株式会社 半導体装置及び有機elディスプレイ装置
JP3887826B2 (ja) * 1997-03-12 2007-02-28 セイコーエプソン株式会社 表示装置及び電子機器
US5912363A (en) 1997-08-29 1999-06-15 Interhealth Nutraceuticals Method for extraction of proanthocyanidins from plant material
JP4013293B2 (ja) * 1997-09-01 2007-11-28 セイコーエプソン株式会社 表示装置兼用型イメージセンサ装置及びアクティブマトリクス型表示装置
EP1014969B1 (en) * 1997-09-09 2008-11-12 Rutgers, The State University of New Jersey Plant proanthocyanidin extract effective at inhibiting adherence of bacteria with p-type fimbriae to surfaces
US6207842B1 (en) 1997-10-09 2001-03-27 Mars Incorporated Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives
US6476864B1 (en) * 1998-05-11 2002-11-05 Agilent Technologies, Inc. Pixel sensor column amplifier architecture
JP4164910B2 (ja) * 1998-09-21 2008-10-15 ソニー株式会社 有機elディスプレイおよび有機elディスプレイの製造方法
US6156912A (en) 1999-04-09 2000-12-05 Mars, Incorporated 88, 66, and 68 catechin and epicatechin dimers and methods for their preparation
US7015338B1 (en) 1999-04-15 2006-03-21 Mars Incorporated Synthetic methods for preparing procyanidin oligomers
US6480305B1 (en) * 1999-05-25 2002-11-12 Hewlett-Packard Company Imaging device
JP2001075524A (ja) * 1999-09-03 2001-03-23 Rohm Co Ltd 表示装置
US6747638B2 (en) * 2000-01-31 2004-06-08 Semiconductor Energy Laboratory Co., Ltd. Adhesion type area sensor and display device having adhesion type area sensor
US6476241B1 (en) 2000-09-05 2002-11-05 Mars Incorporated Synthesis of 4α-arylepicatechins
US7067679B2 (en) 2002-10-02 2006-06-27 Mars, Inc. Synthesis of dimeric, trimeric, tetrameric pentameric, and higher oligomeric epicatechin-derived procyanidins having 4,8-interflavan linkages and their use to inhibit cancer cell growth through cell cycle arrest

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1518003A1 (de) * 1964-01-18 1969-01-30 Merck Ag E Verfahren zur Herstellung von substituierten Flavanderivaten
EP0039844A2 (de) * 1977-11-25 1981-11-18 Zyma SA Verfahren zur Herstellung von O-substituierten Derivaten des (+)-Cyanidan-3-ols
CN1221344A (zh) * 1996-04-02 1999-06-30 火星有限公司 可提取物化合物以及其制备方法和用途

Also Published As

Publication number Publication date
US6528664B2 (en) 2003-03-04
AU760031B2 (en) 2003-05-08
AU1076699A (en) 1999-05-03
WO1999019319A1 (en) 1999-04-22
US20040236123A1 (en) 2004-11-25
US6849746B2 (en) 2005-02-01
US20030176620A1 (en) 2003-09-18
US20020128493A1 (en) 2002-09-12
ATE232857T1 (de) 2003-03-15
DE69811526T2 (de) 2003-11-06
DK1027345T3 (da) 2003-06-10
CN101066962A (zh) 2007-11-07
KR20010030986A (ko) 2001-04-16
EP1027345A1 (en) 2000-08-16
EP1027345B1 (en) 2003-02-19
CN1302295A (zh) 2001-07-04
CA2306851A1 (en) 1999-04-22
IL135344A (en) 2005-11-20
JP2001519426A (ja) 2001-10-23
KR100560463B1 (ko) 2006-03-13
US20040235941A1 (en) 2004-11-25
ES2189260T3 (es) 2003-07-01
US7268240B2 (en) 2007-09-11
IL135344A0 (en) 2001-05-20
US6420572B1 (en) 2002-07-16
US6207842B1 (en) 2001-03-27
DE69811526D1 (en) 2003-03-27

Similar Documents

Publication Publication Date Title
CN100341867C (zh) 多酚的合成方法
CN1207292C (zh) 制备矢车菊苷配质低聚物的合成方法
CN1056849C (zh) 抗真菌的粪壳菌素衍生物及其制备方法和其在制药中的应用
CN1153771C (zh) 苯并呋喃并[3,4-f]喹啉衍生物、含有其的药物组合物及其应用
CN1085561A (zh) 治疗血胆甾醇过多的甾族苷类
CN88102182A (zh) 4-脱甲氧基-4-氨基蒽环类的制备方法
CN1190097A (zh) 苯基乙基酮衍生物及其制备方法
FR2601676A1 (fr) Procede de preparation du taxol et du desacetyl-10 taxol
CN101056868A (zh) 取代的苯并二氢吡喃衍生物、药物及其在治疗中的应用
US9611255B2 (en) Process for total synthesis of flavonoid compounds and isomers thereof
JP2006510730A (ja) エピカテキンおよびカテキン由来のプロシアニジン類オリゴマーの合成法
CN1022569C (zh) 制备泰乐菌素和10,11,12,13-四氢泰乐菌素衍生物的方法
CN101952270B (zh) 制备奈必洛尔的方法
CN1050719A (zh) 表鬼臼毒素阿卓糖苷衍生物的制备方法
CN1440404A (zh) 苯并呋喃衍生物及其作为药物制剂的应用
CN1124922A (zh) 天然产物及相关合成化合物在治疗心血管疾病中的用途
EP1260517B1 (en) Process for preparing flavonoids
CN1106401A (zh) 新的大环内酯类化合物及其应用
CN1699368A (zh) 分离自藤黄树脂并具有抑制肿瘤/癌细胞生长活性的化合物以及包含其的药物组合物
CN87107993A (zh) 含n-羟乙酰神经氨(糖)酸的糖脂及其制备方法
CN1056150C (zh) 3-或4-糖氧基苯并吡喃衍生物和含此衍生物作为活性成分的抗变应剂
CN1050364C (zh) 7-糖氧基苯并吡喃衍生物及抗变应性剂
Chan Neoclerodane diterpenoids from Ajuga taiwanensis
CN1177842C (zh) 新的沉香呋喃衍生物、它们的药物组合物及它们制备药物的用途
CN1086188C (zh) 新颖的菲啶鎓衍生物

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20071010

Termination date: 20091109