CN100341867C - 多酚的合成方法 - Google Patents
多酚的合成方法 Download PDFInfo
- 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
Links
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D311/28—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 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- 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
- C07D311/60—Benzo[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
-
- 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
- C07D311/60—Benzo[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
- C07D311/62—Benzo[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)
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)
| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| US8916526B2 (en) * | 2009-07-31 | 2014-12-23 | National University Corporation Okayama University | Flavanone derivative |
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| US20120238638A1 (en) * | 2011-03-18 | 2012-09-20 | Jorma Antero Virtanen | Biological biocide additives for polymers |
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| US9522131B2 (en) | 2013-01-11 | 2016-12-20 | Wisconsin Alumni Research Foundation | Tannin-containing gastrointestinal formulations and methods of use |
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| 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 |
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| 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 |
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-
1997
- 1997-10-09 US US08/948,226 patent/US6207842B1/en not_active Expired - Fee Related
-
1998
- 1998-10-09 CA CA002306851A patent/CA2306851A1/en not_active Abandoned
- 1998-10-09 ES ES98953371T patent/ES2189260T3/es not_active Expired - Lifetime
- 1998-10-09 WO PCT/US1998/021392 patent/WO1999019319A1/en not_active Ceased
- 1998-10-09 DE DE69811526T patent/DE69811526T2/de not_active Expired - Lifetime
- 1998-10-09 CN CNB988119412A patent/CN100341867C/zh not_active Expired - Fee Related
- 1998-10-09 JP JP2000515891A patent/JP2001519426A/ja active Pending
- 1998-10-09 DK DK98953371T patent/DK1027345T3/da active
- 1998-10-09 AU AU10766/99A patent/AU760031B2/en not_active Ceased
- 1998-10-09 AT AT98953371T patent/ATE232857T1/de active
- 1998-10-09 CN CNA2007100018908A patent/CN101066962A/zh active Pending
- 1998-10-09 EP EP98953371A patent/EP1027345B1/en not_active Expired - Lifetime
- 1998-10-09 US US09/169,554 patent/US6420572B1/en not_active Expired - Fee Related
- 1998-10-09 KR KR1020007003771A patent/KR100560463B1/ko not_active Expired - Fee Related
- 1998-10-09 IL IL13534498A patent/IL135344A/xx not_active IP Right Cessation
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2001
- 2001-12-14 US US10/017,812 patent/US6528664B2/en not_active Expired - Fee Related
-
2003
- 2003-01-31 US US10/355,606 patent/US6849746B2/en not_active Expired - Fee Related
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2004
- 2004-05-28 US US10/858,449 patent/US7268240B2/en not_active Expired - Fee Related
- 2004-06-14 US US10/867,160 patent/US20040235941A1/en not_active Abandoned
Patent Citations (3)
| 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 |
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