RU2443671C2 - Новый способ синтеза (е)-стильбеновых производных, который позволяет получить ресвератрол и писатаннол - Google Patents

Новый способ синтеза (е)-стильбеновых производных, который позволяет получить ресвератрол и писатаннол Download PDF

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RU2443671C2
RU2443671C2 RU2009107169/04A RU2009107169A RU2443671C2 RU 2443671 C2 RU2443671 C2 RU 2443671C2 RU 2009107169/04 A RU2009107169/04 A RU 2009107169/04A RU 2009107169 A RU2009107169 A RU 2009107169A RU 2443671 C2 RU2443671 C2 RU 2443671C2
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Russia
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formula
compound
group
vii
carbon atoms
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RU2009107169/04A
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English (en)
Russian (ru)
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RU2009107169A (ru
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Ален ШУТЕТЕН (FR)
Ален ШУТЕТЕН
Себастьен ЖЮ (FR)
Себастьен ЖЮ
Жан-Клод ВАЛЛЕЖО (FR)
Жан-Клод ВАЛЛЕЖО
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Клариант Спешиалти Файн Кемикалз (Фрэнс)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation 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
    • C07C67/343—Preparation 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
RU2009107169/04A 2006-07-28 2007-07-25 Новый способ синтеза (е)-стильбеновых производных, который позволяет получить ресвератрол и писатаннол RU2443671C2 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0653178A FR2904311B1 (fr) 2006-07-28 2006-07-28 Nouveau procede de synthese de derives (e) stilbeniques perm permettant d'obtenir le resveratrol et le piceatannol
FR0653178 2006-07-28

Publications (2)

Publication Number Publication Date
RU2009107169A RU2009107169A (ru) 2010-09-10
RU2443671C2 true RU2443671C2 (ru) 2012-02-27

Family

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RU2009107169/04A RU2443671C2 (ru) 2006-07-28 2007-07-25 Новый способ синтеза (е)-стильбеновых производных, который позволяет получить ресвератрол и писатаннол

Country Status (9)

Country Link
US (1) US8101804B2 (enExample)
EP (2) EP2049459B8 (enExample)
JP (1) JP5254974B2 (enExample)
CN (1) CN101495436B (enExample)
CA (1) CA2658652C (enExample)
ES (2) ES2436034T3 (enExample)
FR (1) FR2904311B1 (enExample)
RU (1) RU2443671C2 (enExample)
WO (1) WO2008012321A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2826492C1 (ru) * 2023-09-29 2024-09-11 федеральное государственное бюджетное учреждение "Национальный исследовательский центр эпидемиологии и микробиологии имени почетного академика Н.Ф. Гамалеи" Министерства здравоохранения Российской Федерации Химическое соединение тетразамещенный гликолевой кислотой пайсатаннол (E)-2,2'-((4-(3,5-бис(карбоксилатометокси) стирил)-1,2-фенилен)бис(окси)) диацетат, фармацевтическая композиция и её применение для лечения системных воспалительных заболеваний и состояний, в том числе острого респираторного дистресс-синдрома

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2921921B1 (fr) * 2007-10-03 2011-08-19 Clariant Specialty Fine Chem F Procede de synthese de composes polyhydroxystilbeniques.
CN101139267B (zh) * 2007-10-09 2014-01-29 沈阳药科大学 白藜芦醇衍生物、类似物及其制备方法和用途
KR101048475B1 (ko) 2008-12-03 2011-07-11 전남대학교산학협력단 박테리아 사이토크롬 피450을 이용한 피세아타놀의 신규한 생산방법 및 이를 위한 조성물
JP2014527036A (ja) 2011-06-27 2014-10-09 ザ ジャクソン ラボラトリー 癌および自己免疫疾患の処置のための方法および組成物
CN103172512B (zh) * 2011-12-23 2016-08-03 中国医学科学院医药生物技术研究所 一组木豆素结构类似化合物、制备方法和应用
US9701621B2 (en) 2013-02-13 2017-07-11 Indiana University Research & Technology Corporation Poly-cyanostilbene macrocycles
WO2014127171A1 (en) * 2013-02-13 2014-08-21 Indiana University Research And Technology Corporation Poly-cyanostilbene macrocycles
US10077233B2 (en) 2013-02-13 2018-09-18 Indiana University Research And Technology Corporation Poly-cyanostilbene macrocycles
US8921614B1 (en) * 2013-02-26 2014-12-30 The United States Of America As Represented By The Secretary Of The Navy Selective deoxygenation of hydroxybenzaldehydes
CN103992290B (zh) * 2013-05-14 2016-07-06 中国医学科学院医药生物技术研究所 二芳基乙烯结构类似化合物及其制备方法和应用
FR3029912B1 (fr) * 2014-12-12 2018-03-09 L'oreal Nouveaux derives de resveratrol pour lutter contre le vieillissement cutane, compositions et utilisation en cosmetique
TW201702218A (zh) 2014-12-12 2017-01-16 美國杰克森實驗室 關於治療癌症、自體免疫疾病及神經退化性疾病之組合物及方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6407142B1 (en) * 1999-02-17 2002-06-18 L'oreal S.A. Use of stilbene derivatives substituted in position 3 as deodorant active agents in cosmetic compositions
RU2001106631A (ru) * 1998-09-11 2004-03-20 Адзиномото Ко., Инк. (Jp) Производные бензола и их фармацевтическое применение

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2537950A (en) * 1948-11-05 1951-01-16 Milton J Allen Preparation of substituted diamino-stilbenes from pinacols
US3767289A (en) * 1970-12-31 1973-10-23 Ibm Class of stable trans-stilbene compounds, some displaying nematic mesophases at or near room temperature and others in a range up to 100{20 {11 c
JP3330155B2 (ja) * 1991-02-22 2002-09-30 石原産業株式会社 ヒドラゾン系化合物、それらの製造方法及びそれらの製造用中間体ならびにそれらを含有する有害生物防除剤
CN1194674C (zh) 1999-05-18 2005-03-30 卡里克斯治疗公司 新的二苯乙烯化合物
WO2001060774A1 (en) * 2000-02-16 2001-08-23 Brigham Young University Synthesis of resveratrol
US7705188B2 (en) * 2002-04-10 2010-04-27 Arizona Board of Regents, a body corporate of the State of Arizona, Acting for and on Behalf of the Arizona State University Structural modification of resveratrol: sodium resverastatin phosphate
EP1466884A1 (fr) 2003-04-08 2004-10-13 Sochinaz SA Procédé de préparation du resvératrol et ses applications
EP1663926A2 (en) * 2003-09-05 2006-06-07 DSM IP Assets B.V. Process for the preparation of stilbene derivatives
AU2005207029B2 (en) 2004-01-20 2011-09-01 Brigham Young University Novel sirtuin activating compounds and methods for making the same
EP1884508A1 (en) 2006-07-28 2008-02-06 Portela & Ca., S.A. Process for the preparation of polyhydroxylated stilbenes via claisen condensation
WO2008012108A2 (en) * 2006-07-28 2008-01-31 Portela & Ca., S.A. Process for the preparation of polyhydroxylated stilbenes via claisen condensation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2001106631A (ru) * 1998-09-11 2004-03-20 Адзиномото Ко., Инк. (Jp) Производные бензола и их фармацевтическое применение
US6407142B1 (en) * 1999-02-17 2002-06-18 L'oreal S.A. Use of stilbene derivatives substituted in position 3 as deodorant active agents in cosmetic compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
A.Talvitie et al "Enrichment, Characterization and Absolute Configuration of the Enantiomers of 1-(3,5-Dimethoxyphenyl)-2-(4-methoxyphenyl)ethanol". Acta Chemica Scandinavica, 1996, 50, 1143-1146. J.C.Roberts et al "The photochemistry of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethyl ethanoate in alcohol solvents: A search for carbocation rearrangements". Can. J. Chem., 2003, 81, 709-722. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2828710C1 (ru) * 2019-12-23 2024-10-16 Кайнан Дьюк АйПи, ЭлЭлСи Соединения и производные замещенного гидроксистильбена, их синтез и применение
RU2826492C1 (ru) * 2023-09-29 2024-09-11 федеральное государственное бюджетное учреждение "Национальный исследовательский центр эпидемиологии и микробиологии имени почетного академика Н.Ф. Гамалеи" Министерства здравоохранения Российской Федерации Химическое соединение тетразамещенный гликолевой кислотой пайсатаннол (E)-2,2'-((4-(3,5-бис(карбоксилатометокси) стирил)-1,2-фенилен)бис(окси)) диацетат, фармацевтическая композиция и её применение для лечения системных воспалительных заболеваний и состояний, в том числе острого респираторного дистресс-синдрома

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Publication number Publication date
JP2009544663A (ja) 2009-12-17
EP2202215B8 (en) 2013-11-13
JP5254974B2 (ja) 2013-08-07
EP2049459A1 (en) 2009-04-22
EP2049459B8 (en) 2013-11-13
WO2008012321A1 (en) 2008-01-31
CA2658652C (en) 2014-10-28
EP2202215A2 (en) 2010-06-30
FR2904311B1 (fr) 2013-01-11
CN101495436A (zh) 2009-07-29
EP2202215B1 (en) 2013-10-02
US20100004483A1 (en) 2010-01-07
EP2202215A3 (en) 2010-09-08
CA2658652A1 (en) 2008-01-31
ES2436110T3 (es) 2013-12-27
CN101495436B (zh) 2014-02-26
EP2049459B1 (en) 2013-10-02
ES2436034T3 (es) 2013-12-26
US8101804B2 (en) 2012-01-24
RU2009107169A (ru) 2010-09-10
FR2904311A1 (fr) 2008-02-01

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