WO2003031381A3 - Synthesis of (z)-3,5,4'-trimethoxystilbene, and use thereof - Google Patents

Synthesis of (z)-3,5,4'-trimethoxystilbene, and use thereof Download PDF

Info

Publication number
WO2003031381A3
WO2003031381A3 PCT/FR2002/003492 FR0203492W WO03031381A3 WO 2003031381 A3 WO2003031381 A3 WO 2003031381A3 FR 0203492 W FR0203492 W FR 0203492W WO 03031381 A3 WO03031381 A3 WO 03031381A3
Authority
WO
WIPO (PCT)
Prior art keywords
compound
synthesis
trimethoxystilbene
invention concerns
medicine
Prior art date
Application number
PCT/FR2002/003492
Other languages
French (fr)
Other versions
WO2003031381A2 (en
Inventor
Francis Raul
Yann Schneider
Raymond Brouillard
Andre Fougerousse
Philippe Chabert
Emmanuel Gonzalez
Original Assignee
Univ Pasteur
Inst Nat Sante Rech Med
Centre Nat Rech Scient
Francis Raul
Yann Schneider
Raymond Brouillard
Andre Fougerousse
Philippe Chabert
Emmanuel Gonzalez
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 Univ Pasteur, Inst Nat Sante Rech Med, Centre Nat Rech Scient, Francis Raul, Yann Schneider, Raymond Brouillard, Andre Fougerousse, Philippe Chabert, Emmanuel Gonzalez filed Critical Univ Pasteur
Priority to AU2002350838A priority Critical patent/AU2002350838A1/en
Publication of WO2003031381A2 publication Critical patent/WO2003031381A2/en
Publication of WO2003031381A3 publication Critical patent/WO2003031381A3/en

Links

Classifications

    • 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
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • 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
    • 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
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • 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
    • C07C41/32—Preparation of ethers by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention concerns the field of organic chemistry and more particularly that related to the synthesis of novel molecules capable of exhibiting biological properties, in particular therapeutic and more particularly properties for preventing or treating certain diseases such as in particular cancer-type diseases. The invention concerns a novel method for chemical synthesis of (Z)-3,5,4'-trimethoxystilbene (compound R3), the compound obtainable by said method, the use of said compound as medicine in particular as synthetic anticancer drug at low production cost, the corresponding medicine and various uses of said compound (R3).
PCT/FR2002/003492 2001-10-12 2002-10-11 Synthesis of (z)-3,5,4'-trimethoxystilbene, and use thereof WO2003031381A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002350838A AU2002350838A1 (en) 2001-10-12 2002-10-11 Synthesis of (z)-3,5,4'-trimethoxystilbene, and use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0113220A FR2830860A1 (en) 2001-10-12 2001-10-12 New process for preparing (Z)-3,5,4'-trimethoxystilbene from (E)-3,5,4'-trimethoxystilbene, and its use against cancer, malaria, cystic fibrosis and other disorders
FR01/13220 2001-10-12

Publications (2)

Publication Number Publication Date
WO2003031381A2 WO2003031381A2 (en) 2003-04-17
WO2003031381A3 true WO2003031381A3 (en) 2004-02-26

Family

ID=8868265

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2002/003492 WO2003031381A2 (en) 2001-10-12 2002-10-11 Synthesis of (z)-3,5,4'-trimethoxystilbene, and use thereof

Country Status (3)

Country Link
AU (1) AU2002350838A1 (en)
FR (1) FR2830860A1 (en)
WO (1) WO2003031381A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100586428C (en) * 2001-11-02 2010-02-03 加州大学校务委员会 Compositions for prevention and treatment of inflammatory disease, autoimmune disease, and transplant rejection and application thereof in preparing medicine
TW200819409A (en) * 2006-10-19 2008-05-01 Univ Taipei Medical Z-stilbenes derivatives and the pharmaceutical composition thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4940707A (en) * 1988-02-24 1990-07-10 Hoffman-La Roche Inc. Stilbene derivatives for treatment of skin disorders
WO2001021165A1 (en) * 1999-09-21 2001-03-29 Rutgers, The State University Resveratrol analogs for prevention of disease
WO2001042231A2 (en) * 1999-12-06 2001-06-14 Welichem Biotech Inc. Polyhydroxystilbenes and stilbene oxides as antisoriatic agents and protein kinase inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4940707A (en) * 1988-02-24 1990-07-10 Hoffman-La Roche Inc. Stilbene derivatives for treatment of skin disorders
WO2001021165A1 (en) * 1999-09-21 2001-03-29 Rutgers, The State University Resveratrol analogs for prevention of disease
WO2001042231A2 (en) * 1999-12-06 2001-06-14 Welichem Biotech Inc. Polyhydroxystilbenes and stilbene oxides as antisoriatic agents and protein kinase inhibitors

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
B. C. TRELA ET AL: "Resveratrol: isomeric molar absorptivities and stability", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 44, no. 5, 1996, pages 1253 - 1257, XP000583846 *
G. R. PETTIT ET AL: "Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, no. 10, 1995, WASHINGTON US, pages 1666 - 1672, XP002203198 *
M. CUSHMAN ET AL: "Synthesis and evaluation of analogues of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, no. 12, 1992, WASHINGTON US, pages 2293 - 2306, XP000571677 *
M. YASUDA ET AL: "Regiochemistry on photoamination of stilbene derivatives with ammonia via electron transfer", JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 5, 28 February 1992 (1992-02-28), EASTON US, pages 1351 - 1354, XP002203203 *

Also Published As

Publication number Publication date
FR2830860A1 (en) 2003-04-18
AU2002350838A1 (en) 2003-04-22
WO2003031381A2 (en) 2003-04-17

Similar Documents

Publication Publication Date Title
WO2003032994A3 (en) Novel tri-substituted pyrimidines, method for production and use thereof as medicament
IL176062A0 (en) Dpp-iv inhibitors
MXPA03011972A (en) Arylamines for the treatment of conditions associated with gsk-3.
WO2006064033A3 (en) Glucopyranosyl-substituted benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
WO2003080582A3 (en) Fredericamycin derivatives
EP1875910A4 (en) Application of levo-ornidazole in preparation of anti-anaerobic bacteria infection medicine
WO2004074232A8 (en) 1-phenylalkanecarboxylic acid derivatives for the treatment of neurodegenerative diseases
WO2005037798A3 (en) Amide or thiomide derivatives and their use in the treatment of pain
WO2005021497A3 (en) Tethered dimers and trimers of 1,4-diphenylazetidn-2-ones
UA90504C2 (en) Novel drugs for treating respiratory diseases
HK1090354A1 (en) Novel dibenzo [b,f]oxepine-10-carboxamides and pharmaceutical uses thereof
AU2003293296A1 (en) A group of novel synthetic antibiotic peptides
WO2003015780A8 (en) Isoxazolopyridinones and use thereof in the treatment of parkinson's disease
BRPI0409069A (en) chemical compounds
WO2003018568A3 (en) Ascorbic acid derivatives, methods of synthesis and pharmaceutical use thereof
WO2005039589A3 (en) Cftr channel modulators
WO2003031381A3 (en) Synthesis of (z)-3,5,4'-trimethoxystilbene, and use thereof
WO2008102888A1 (en) Novel pseudoglycolipid and use thereof
WO2007003767A3 (en) Novel chemical compounds and the uses thereof as a medicine
WO2005007083A3 (en) Chemical compounds
BR0211223A (en) Substituted 4-aminocyclohexanol derivatives
WO2004091542A3 (en) Nitrogen containing integrin targeting compounds
AU2003290418A1 (en) Novel molecules to develop drug for the treatment of osteoporosis
WO2004112714A3 (en) Chemical compounds
WO2005014542A3 (en) Novel n-substituted indolyl-3-glyoxylic acid amides, use thereof as a medicament against cancer, and method for the production thereof

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR LC LK LR LS LT LU LV MA MD MG MN MW MX MZ NO NZ OM PH PL PT RU SD SE SG SI SK SL TJ TM TN TR TZ UA UG US UZ VC VN YU ZA ZM

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ UG ZM ZW AM AZ BY KG KZ RU TJ TM AT BE BG CH CY CZ DK EE ES FI FR GB GR IE IT LU MC PT SE SK TR BF BJ CF CG CI GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP