WO2010010578A3 - A key intermediate for the preparation of stilbenes - Google Patents

A key intermediate for the preparation of stilbenes Download PDF

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Publication number
WO2010010578A3
WO2010010578A3 PCT/IN2009/000313 IN2009000313W WO2010010578A3 WO 2010010578 A3 WO2010010578 A3 WO 2010010578A3 IN 2009000313 W IN2009000313 W IN 2009000313W WO 2010010578 A3 WO2010010578 A3 WO 2010010578A3
Authority
WO
WIPO (PCT)
Prior art keywords
stilbenes
preparation
key intermediate
tetrahydropyranylstilbene
tetrahydropyranyl
Prior art date
Application number
PCT/IN2009/000313
Other languages
French (fr)
Other versions
WO2010010578A2 (en
Inventor
Venkata Subbaraju Gottumukkala
Mahesh Masna
Rama Mohan Hindupur
Suresh Thatipally
Original Assignee
Aptuit Laurus Private Limited
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 Aptuit Laurus Private Limited filed Critical Aptuit Laurus Private Limited
Priority to PCT/US2010/022285 priority Critical patent/WO2010141107A1/en
Publication of WO2010010578A2 publication Critical patent/WO2010010578A2/en
Publication of WO2010010578A3 publication Critical patent/WO2010010578A3/en
Priority to US13/011,593 priority patent/US8524782B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides a scalable process for the preparation of Stilbenes by (i) condensing 3,5-dialkylbenzyl phosphonates with 4'-O-tetrahydropyranyl benzaldehyde to get 3,5-alkyl-4'-O-tetrahydropyranyl Stilbene (ii) deprotecting the obtained 3,5-Dialkyl- 4'-O-tetrahydropyranylstilbene yields Stilbenes. The present invention also provides a novel intermediate 3,5-Dialkyl-4'-O-tetrahydropyranylstilbene, which is a key intermediate for the synthesis of Stilbenes such as Pterostilbene and Resveratrol.
PCT/IN2009/000313 2008-07-23 2009-06-01 A key intermediate for the preparation of stilbenes WO2010010578A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/US2010/022285 WO2010141107A1 (en) 2009-06-01 2010-01-27 Solid forms of pterostilbene
US13/011,593 US8524782B2 (en) 2008-07-23 2011-01-21 Key intermediate for the preparation of Stilbenes, solid forms of Pterostilbene, and methods for making the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1766/CHE/2008 2008-07-23
IN1766CH2008 2008-07-23

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/022285 Continuation-In-Part WO2010141107A1 (en) 2008-07-23 2010-01-27 Solid forms of pterostilbene

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/011,593 Continuation-In-Part US8524782B2 (en) 2008-07-23 2011-01-21 Key intermediate for the preparation of Stilbenes, solid forms of Pterostilbene, and methods for making the same

Publications (2)

Publication Number Publication Date
WO2010010578A2 WO2010010578A2 (en) 2010-01-28
WO2010010578A3 true WO2010010578A3 (en) 2010-11-11

Family

ID=41570679

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2009/000313 WO2010010578A2 (en) 2008-07-23 2009-06-01 A key intermediate for the preparation of stilbenes

Country Status (1)

Country Link
WO (1) WO2010010578A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103102254B (en) * 2013-02-06 2015-08-26 浙江新赛科药业有限公司 The synthetic method of a kind of Pterostilene
CN103450130A (en) * 2013-09-13 2013-12-18 陕西嘉禾植物化工有限责任公司 Toluylene compound and preparation method thereof
CN103467255B (en) * 2013-09-13 2015-07-01 陕西嘉禾植物化工有限责任公司 Synthetic method of natural product pterostilbene
CN114929659B (en) * 2019-12-20 2024-05-28 晶体工程智能研究中心公司 Co-crystals of pterostilbene and compositions containing same
CN116217471A (en) * 2023-03-20 2023-06-06 贵州大学 Pterocarpus stilbene pyridine salt compound, intermediate compound, composition, medicine, preparation method and application

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1948274A (en) * 2006-10-25 2007-04-18 沈阳药科大学 Verakanol derivative, its preparation method and use
CN1955153A (en) * 2005-10-24 2007-05-02 南京莱因医药科技有限公司 Synthetic method of pterostilbene

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1955153A (en) * 2005-10-24 2007-05-02 南京莱因医药科技有限公司 Synthetic method of pterostilbene
CN1948274A (en) * 2006-10-25 2007-04-18 沈阳药科大学 Verakanol derivative, its preparation method and use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YUE-QING, LI ET AL.: "Synthesis of stilbene derivatives with inhibition of SARS coronavirus replication", pages 1085 - 1086 *

Also Published As

Publication number Publication date
WO2010010578A2 (en) 2010-01-28

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