WO2002006279A1 - Efficient method of synthesizing combretastatin a-4 prodrugs - Google Patents

Efficient method of synthesizing combretastatin a-4 prodrugs Download PDF

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Publication number
WO2002006279A1
WO2002006279A1 PCT/US2001/022403 US0122403W WO0206279A1 WO 2002006279 A1 WO2002006279 A1 WO 2002006279A1 US 0122403 W US0122403 W US 0122403W WO 0206279 A1 WO0206279 A1 WO 0206279A1
Authority
WO
WIPO (PCT)
Prior art keywords
combretastatin
prodrugs
efficient method
synthesizing
synthesizing combretastatin
Prior art date
Application number
PCT/US2001/022403
Other languages
French (fr)
Other versions
WO2002006279A3 (en
WO2002006279A9 (en
WO2002006279A8 (en
Inventor
Faye Seyedi
Jonathan Gale
Reem Haider
John Hoare
Original Assignee
Oxigene Inc
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 Oxigene Inc filed Critical Oxigene Inc
Priority to AU2001296215A priority Critical patent/AU2001296215A1/en
Publication of WO2002006279A1 publication Critical patent/WO2002006279A1/en
Publication of WO2002006279A8 publication Critical patent/WO2002006279A8/en
Publication of WO2002006279A3 publication Critical patent/WO2002006279A3/en
Publication of WO2002006279A9 publication Critical patent/WO2002006279A9/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
    • 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

Abstract

Methods of synthesizing a phosphate ester of combretastatin A-4 and trans-isomers thereof in which combretastatin A-4 is reacted with dibenzylphosphite in the presence of carbon tetrabromide, or with 2,2,2-trichloroethyl phosphorodichloridate, to form a phosphate ester of combretastatin A-4 with protecting groups thereon.
PCT/US2001/022403 2000-07-17 2001-07-17 Efficient method of synthesizing combretastatin a-4 prodrugs WO2002006279A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001296215A AU2001296215A1 (en) 2000-07-17 2001-07-17 Efficient method of synthesizing combretastatin a-4 prodrugs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US21876600P 2000-07-17 2000-07-17

Publications (4)

Publication Number Publication Date
WO2002006279A1 true WO2002006279A1 (en) 2002-01-24
WO2002006279A8 WO2002006279A8 (en) 2002-02-14
WO2002006279A3 WO2002006279A3 (en) 2002-04-18
WO2002006279A9 WO2002006279A9 (en) 2003-04-03

Family

ID=22816425

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/022403 WO2002006279A1 (en) 2000-07-17 2001-07-17 Efficient method of synthesizing combretastatin a-4 prodrugs

Country Status (3)

Country Link
US (1) US6743937B2 (en)
AU (1) AU2001296215A1 (en)
WO (1) WO2002006279A1 (en)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004085421A2 (en) * 2003-03-26 2004-10-07 Angiogene Pharmaceuticals Limited Bioreductively-activated prodrugs
US7105695B2 (en) 2001-12-21 2006-09-12 Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University Synthesis of combretastatin A-2 prodrugs
EP1740588A2 (en) * 2004-04-16 2007-01-10 Choongwae Pharma Corporation Reverse-turn mimetics and method relating thereto
CN1312161C (en) * 2005-04-30 2007-04-25 中国科学院广州化学研究所 3-hydroxy-4,3',4',5'-tetromethoxy bibenzyl phosphate and its composition, prepn and application
WO2007077003A1 (en) 2005-12-30 2007-07-12 Ecopack France S.A.S. Improved bag valve
WO2008010463A1 (en) 2006-07-19 2008-01-24 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of combretastatin
WO2011036674A1 (en) * 2009-09-24 2011-03-31 Inogent Laboratories Private Limited A new process for the preparation of olmesartan medoxomil
WO2011067538A1 (en) 2009-12-03 2011-06-09 Sanofi-Aventis Combretastatin derivative preparation method
US8188222B2 (en) 2006-11-08 2012-05-29 Nippon Kayaku Kabushiki Kaisha High molecular weight derivative of nucleic acid antimetabolite
US8323669B2 (en) 2006-03-28 2012-12-04 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of taxane
US8334364B2 (en) 2006-11-06 2012-12-18 Nipon Kayaku Kabushiki Kaisha High-molecular weight derivative of nucleic acid antimetabolite
US8703878B2 (en) 2007-09-28 2014-04-22 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of steroids
US8808749B2 (en) 2009-05-15 2014-08-19 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of bioactive substance having hydroxy group
US8920788B2 (en) 2008-03-18 2014-12-30 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of physiologically active substances
US8940332B2 (en) 2006-05-18 2015-01-27 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of podophyllotoxins
US9018323B2 (en) 2010-11-17 2015-04-28 Nippon Kayaku Kabushiki Kaisha Polymer derivative of cytidine metabolic antagonist
CN104892668A (en) * 2015-05-12 2015-09-09 上海大学 Combretastatin A-4 analogue water soluble pro-prodrug, and preparation method thereof
US9149540B2 (en) 2008-05-08 2015-10-06 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of folic acid or folic acid derivative
US9346923B2 (en) 2011-09-11 2016-05-24 Nippon Kayaku Kabushiki Kaisha Method for manufacturing block copolymer
US9434822B2 (en) 2004-09-22 2016-09-06 Nippon Kayaku Kabushiki Kaisha Block copolymer, micelle preparation, and anticancer agent containing the same as active ingredient

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN100343216C (en) * 2004-05-25 2007-10-17 浙江大德药业集团有限公司 Synthesis of Combretastatin A-4 supported by polymer
CA2664852A1 (en) * 2006-10-03 2008-04-10 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of resorcinol derivatives
ES2529434T3 (en) * 2007-11-21 2015-02-20 Oxigene, Inc. Method to treat hematopoietic neoplasms
JP2012532113A (en) * 2009-07-02 2012-12-13 オキシジーン， インコーポレイテッド Combretastatin to prevent posterior capsule opacification
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
US11419934B2 (en) 2015-08-18 2022-08-23 Oncotelic Therapeutics, Inc. Use of VDAS to enhance immunomodulating therapies against tumors

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4670193A (en) * 1986-05-12 1987-06-02 E. R. Squibb & Sons, Inc. Process for preparing phosphonic acids

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4996237A (en) 1987-01-06 1991-02-26 Arizona Board Of Regents Combretastatin A-4
CA1338645C (en) 1987-01-06 1996-10-15 George R. Pettit Isolation, structural elucidation and synthesis of novel antineoplastic substances denominated "combretastatins"
GB9106177D0 (en) 1991-03-22 1991-05-08 Aston Molecules Ltd Substituted diphenylethylenes and analogues or derivatives thereof
US5561122A (en) 1994-12-22 1996-10-01 Arizona Board Of Regents Acting On Behalf Of Arizona State University Combretastatin A-4 prodrug
US7018987B1 (en) 1998-01-09 2006-03-28 Arizona Broad of Regents acting for and on behalf of Arizona State University Synthesis of combretastatin A-4 prodrugs and trans-isomers thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4670193A (en) * 1986-05-12 1987-06-02 E. R. Squibb & Sons, Inc. Process for preparing phosphonic acids

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7105695B2 (en) 2001-12-21 2006-09-12 Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University Synthesis of combretastatin A-2 prodrugs
WO2004085421A2 (en) * 2003-03-26 2004-10-07 Angiogene Pharmaceuticals Limited Bioreductively-activated prodrugs
WO2004085421A3 (en) * 2003-03-26 2005-03-24 Angiogene Pharm Ltd Bioreductively-activated prodrugs
EP1740588A2 (en) * 2004-04-16 2007-01-10 Choongwae Pharma Corporation Reverse-turn mimetics and method relating thereto
US9434822B2 (en) 2004-09-22 2016-09-06 Nippon Kayaku Kabushiki Kaisha Block copolymer, micelle preparation, and anticancer agent containing the same as active ingredient
CN1312161C (en) * 2005-04-30 2007-04-25 中国科学院广州化学研究所 3-hydroxy-4,3',4',5'-tetromethoxy bibenzyl phosphate and its composition, prepn and application
WO2007077003A1 (en) 2005-12-30 2007-07-12 Ecopack France S.A.S. Improved bag valve
US8323669B2 (en) 2006-03-28 2012-12-04 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of taxane
US8940332B2 (en) 2006-05-18 2015-01-27 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of podophyllotoxins
WO2008010463A1 (en) 2006-07-19 2008-01-24 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of combretastatin
US8334364B2 (en) 2006-11-06 2012-12-18 Nipon Kayaku Kabushiki Kaisha High-molecular weight derivative of nucleic acid antimetabolite
US8188222B2 (en) 2006-11-08 2012-05-29 Nippon Kayaku Kabushiki Kaisha High molecular weight derivative of nucleic acid antimetabolite
USRE46190E1 (en) 2007-09-28 2016-11-01 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of steroids
US8703878B2 (en) 2007-09-28 2014-04-22 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of steroids
US8920788B2 (en) 2008-03-18 2014-12-30 Nippon Kayaku Kabushiki Kaisha High-molecular weight conjugate of physiologically active substances
US9149540B2 (en) 2008-05-08 2015-10-06 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of folic acid or folic acid derivative
US8808749B2 (en) 2009-05-15 2014-08-19 Nippon Kayaku Kabushiki Kaisha Polymer conjugate of bioactive substance having hydroxy group
WO2011036674A1 (en) * 2009-09-24 2011-03-31 Inogent Laboratories Private Limited A new process for the preparation of olmesartan medoxomil
WO2011067538A1 (en) 2009-12-03 2011-06-09 Sanofi-Aventis Combretastatin derivative preparation method
US9018323B2 (en) 2010-11-17 2015-04-28 Nippon Kayaku Kabushiki Kaisha Polymer derivative of cytidine metabolic antagonist
US9346923B2 (en) 2011-09-11 2016-05-24 Nippon Kayaku Kabushiki Kaisha Method for manufacturing block copolymer
CN104892668A (en) * 2015-05-12 2015-09-09 上海大学 Combretastatin A-4 analogue water soluble pro-prodrug, and preparation method thereof
CN104892668B (en) * 2015-05-12 2017-03-29 上海大学 Prodrug and preparation method thereof before combretastatin analog water solublity

Also Published As

Publication number Publication date
WO2002006279A3 (en) 2002-04-18
US20020119951A1 (en) 2002-08-29
WO2002006279A9 (en) 2003-04-03
US6743937B2 (en) 2004-06-01
AU2001296215A1 (en) 2002-01-30
WO2002006279A8 (en) 2002-02-14

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