IL154729A0 - SYNTHESIS OF 4alpha-ARYLEPICATECHINS - Google Patents
SYNTHESIS OF 4alpha-ARYLEPICATECHINSInfo
- Publication number
- IL154729A0 IL154729A0 IL15472901A IL15472901A IL154729A0 IL 154729 A0 IL154729 A0 IL 154729A0 IL 15472901 A IL15472901 A IL 15472901A IL 15472901 A IL15472901 A IL 15472901A IL 154729 A0 IL154729 A0 IL 154729A0
- Authority
- IL
- Israel
- Prior art keywords
- 4alpha
- epicatechin
- resulting
- synthesis
- hydride
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- 230000000707 stereoselective effect Effects 0.000 abstract 2
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical group C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 abstract 1
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001499 aryl bromides Chemical class 0.000 abstract 1
- -1 benzylic alcohols Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229920002770 condensed tannin Polymers 0.000 abstract 1
- 239000000539 dimer Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 abstract 1
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
- C07D311/74—Benzo[b]pyrans, 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
- C07D311/58—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/655,360 US6476241B1 (en) | 2000-09-05 | 2000-09-05 | Synthesis of 4α-arylepicatechins |
| PCT/US2001/026175 WO2002020506A2 (en) | 2000-09-05 | 2001-08-21 | SYNTHESIS OF 4α-ARYLEPICATECHINS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL154729A0 true IL154729A0 (en) | 2003-10-31 |
Family
ID=24628579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL15472901A IL154729A0 (en) | 2000-09-05 | 2001-08-21 | SYNTHESIS OF 4alpha-ARYLEPICATECHINS |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US6476241B1 (xx) |
| EP (1) | EP1317437B1 (xx) |
| JP (1) | JP2004508362A (xx) |
| CN (1) | CN100358885C (xx) |
| AT (1) | ATE374759T1 (xx) |
| AU (2) | AU2001283472B2 (xx) |
| CA (1) | CA2421513A1 (xx) |
| DE (1) | DE60130785D1 (xx) |
| IL (1) | IL154729A0 (xx) |
| RU (1) | RU2281942C2 (xx) |
| WO (1) | WO2002020506A2 (xx) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6476241B1 (en) * | 2000-09-05 | 2002-11-05 | Mars Incorporated | Synthesis of 4α-arylepicatechins |
| WO2004030480A1 (en) * | 2002-10-01 | 2004-04-15 | Nellcor Puritan Bennett Incorporated | Headband with tension indicator |
| 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 |
| EP1742656B1 (en) | 2004-03-12 | 2010-06-16 | University Of Georgia Research Foundation, Inc. | Novel peanut skin extract as a vaccine adjuvant |
| 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 |
| CA2611856C (en) | 2005-06-29 | 2018-02-27 | Mars, Incorporated | Inducing peripheral blood vessel vasodilation using polyphenols provided as cocoa |
| 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 |
| US20080145919A1 (en) * | 2006-12-18 | 2008-06-19 | Franklin Thomas D | Portable organ and tissue preservation apparatus, kit and methods |
| JP5290558B2 (ja) * | 2007-10-10 | 2013-09-18 | 株式会社エヌ・ティー・エイチ | ナチュラルヘナ抽出物とその用途 |
| EA201190219A1 (ru) * | 2009-04-17 | 2013-01-30 | Кардеро Терапьютикс, Инк. | Способы и композиции для лечения ишемических состояний и состояний, связанных с функцией митохондрий |
| AU2011311255B2 (en) | 2010-04-28 | 2015-10-08 | Sorrento Therapeutics, Inc. | Method for increasing permeability of an epithelial barrier |
| JP5890846B2 (ja) * | 2011-01-27 | 2016-03-22 | スファエラ ファーマ ピーティーイー リミテッド | ポリフェノールの新規合成方法 |
| JP6411375B2 (ja) | 2013-01-26 | 2018-10-24 | スファエラ ファーマ プライベート リミテッド | カテキンの新規合成手法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1493976C3 (de) | 1964-01-18 | 1973-09-13 | Merck Patent Gmbh, 6100 Darmstadt | Substituierte Flavandenvate sowie Verfahren zu ihrer Herstellung |
| US4255336A (en) | 1977-11-25 | 1981-03-10 | Ciba-Geigy Corporation | Process for the preparation of O-substituted derivatives of (+)-cyanidan-3-01 |
| GB2122608B (en) * | 1982-06-01 | 1985-10-02 | Zyma Sa | (+)-cyanidan-3-ol derivatives |
| EP0472531B1 (fr) | 1989-05-12 | 1995-08-16 | Cariel, Léon | Composition a base de proanthocyanidols; leur application pharmacologique |
| US5554645A (en) | 1994-10-03 | 1996-09-10 | Mars, Incorporated | Antineoplastic cocoa extracts and methods for making and using the same |
| US6207842B1 (en) * | 1997-10-09 | 2001-03-27 | Mars Incorporated | Process for preparing procyanidin(4-6 or 4-8) oligomers and their derivatives |
| EP1026164A1 (en) | 1999-02-02 | 2000-08-09 | ADM Cocoa B.V. | Process for extracting polyphenolic antioxidants from purine-containing plants |
| 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 |
| US6476241B1 (en) * | 2000-09-05 | 2002-11-05 | Mars Incorporated | Synthesis of 4α-arylepicatechins |
| US6420972B1 (en) * | 2000-10-18 | 2002-07-16 | Wms Gaming, Inc. | Door monitor for a gaming machine |
| 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 |
| EP1554270A2 (en) * | 2002-10-11 | 2005-07-20 | Proteotech, Inc. | Isolation, purification and synthesis of procyanidin b2 and uses thereof |
| US7756362B2 (en) * | 2005-01-28 | 2010-07-13 | Canon Kabushiki Kaisha | Image processing apparatus, control method therefor, computer program, and computer-readable storage medium |
-
2000
- 2000-09-05 US US09/655,360 patent/US6476241B1/en not_active Expired - Fee Related
-
2001
- 2001-08-21 CA CA002421513A patent/CA2421513A1/en not_active Abandoned
- 2001-08-21 RU RU2003109618/04A patent/RU2281942C2/ru not_active IP Right Cessation
- 2001-08-21 AT AT01962277T patent/ATE374759T1/de not_active IP Right Cessation
- 2001-08-21 AU AU2001283472A patent/AU2001283472B2/en not_active Ceased
- 2001-08-21 WO PCT/US2001/026175 patent/WO2002020506A2/en active IP Right Grant
- 2001-08-21 CN CNB018183212A patent/CN100358885C/zh not_active Expired - Fee Related
- 2001-08-21 DE DE60130785T patent/DE60130785D1/de not_active Expired - Lifetime
- 2001-08-21 EP EP01962277A patent/EP1317437B1/en not_active Expired - Lifetime
- 2001-08-21 IL IL15472901A patent/IL154729A0/xx unknown
- 2001-08-21 JP JP2002525127A patent/JP2004508362A/ja not_active Abandoned
- 2001-08-21 AU AU8347201A patent/AU8347201A/xx active Pending
-
2002
- 2002-08-08 US US10/214,830 patent/US6720432B2/en not_active Expired - Fee Related
-
2004
- 2004-02-20 US US10/783,801 patent/US7126014B2/en not_active Expired - Fee Related
-
2006
- 2006-10-05 US US11/543,415 patent/US20070197804A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6720432B2 (en) | 2004-04-13 |
| CA2421513A1 (en) | 2002-03-14 |
| ATE374759T1 (de) | 2007-10-15 |
| CN1473159A (zh) | 2004-02-04 |
| WO2002020506A3 (en) | 2003-02-06 |
| RU2281942C2 (ru) | 2006-08-20 |
| US7126014B2 (en) | 2006-10-24 |
| AU2001283472B2 (en) | 2007-05-24 |
| EP1317437A2 (en) | 2003-06-11 |
| US20050014958A1 (en) | 2005-01-20 |
| DE60130785D1 (de) | 2007-11-15 |
| US20070197804A1 (en) | 2007-08-23 |
| US20030100775A1 (en) | 2003-05-29 |
| US6476241B1 (en) | 2002-11-05 |
| WO2002020506A2 (en) | 2002-03-14 |
| AU2001283472B9 (en) | 2002-03-22 |
| JP2004508362A (ja) | 2004-03-18 |
| AU8347201A (en) | 2002-03-22 |
| CN100358885C (zh) | 2008-01-02 |
| EP1317437B1 (en) | 2007-10-03 |
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