WO2001012579A3 - New stilbenes with vascular damaging activity - Google Patents

New stilbenes with vascular damaging activity Download PDF

Info

Publication number
WO2001012579A3
WO2001012579A3 PCT/GB2000/003067 GB0003067W WO0112579A3 WO 2001012579 A3 WO2001012579 A3 WO 2001012579A3 GB 0003067 W GB0003067 W GB 0003067W WO 0112579 A3 WO0112579 A3 WO 0112579A3
Authority
WO
WIPO (PCT)
Prior art keywords
stilbenes
vascular damaging
new
damaging activity
alkyl
Prior art date
Application number
PCT/GB2000/003067
Other languages
French (fr)
Other versions
WO2001012579A2 (en
Inventor
Peter David Davis
Original Assignee
Angiogene Pharm Ltd
Peter David Davis
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 Angiogene Pharm Ltd, Peter David Davis filed Critical Angiogene Pharm Ltd
Priority to EP00951727A priority Critical patent/EP1206429A2/en
Priority to AU64581/00A priority patent/AU779980B2/en
Priority to NZ517069A priority patent/NZ517069A/en
Priority to CA002379544A priority patent/CA2379544A1/en
Priority to JP2001516880A priority patent/JP2003507356A/en
Publication of WO2001012579A2 publication Critical patent/WO2001012579A2/en
Publication of WO2001012579A3 publication Critical patent/WO2001012579A3/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
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/52—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an inorganic compound, e.g. an inorganic ion that is complexed with the active ingredient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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

Abstract

A group of novel cis-stilbenes as disclosed of formula (1) wherein: R?1, R2 and R3¿ are each independently alkyl, R4 is alkyl, haloalkyl, alkenyl, alkynyl, alkylthio, alkylsulphinyl, alkylsulphonyl or halo, R5 is hydrogen, alkoxy, alkyl, alkylthio, hydroxy or halo, or a pharmaceutically acceptable salt thereof or a prodrug such as a phosphate ester. These compounds have vascular damaging activity and are therefore potentially of value in treatment of diseases where reversal of neovascularisation may have therapeutic benefit.
PCT/GB2000/003067 1999-02-16 2000-08-09 New stilbenes with vascular damaging activity WO2001012579A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP00951727A EP1206429A2 (en) 1999-08-12 2000-08-09 Stilbenes with vascular damaging activity
AU64581/00A AU779980B2 (en) 1999-02-16 2000-08-09 New stilbenes with vascular damaging activity
NZ517069A NZ517069A (en) 1999-08-12 2000-08-09 New stilbenes with vascular damaging activity
CA002379544A CA2379544A1 (en) 1999-08-12 2000-08-09 New stilbenes with vascular damaging activity
JP2001516880A JP2003507356A (en) 1999-08-12 2000-08-09 New stilbenes with vascular damage activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9918912.8A GB9918912D0 (en) 1999-08-12 1999-08-12 New stilbenes with vascular damaging activity
GB9918912.8 1999-08-12

Publications (2)

Publication Number Publication Date
WO2001012579A2 WO2001012579A2 (en) 2001-02-22
WO2001012579A3 true WO2001012579A3 (en) 2001-10-11

Family

ID=10858950

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/003067 WO2001012579A2 (en) 1999-02-16 2000-08-09 New stilbenes with vascular damaging activity

Country Status (6)

Country Link
EP (1) EP1206429A2 (en)
JP (1) JP2003507356A (en)
CA (1) CA2379544A1 (en)
GB (1) GB9918912D0 (en)
NZ (1) NZ517069A (en)
WO (1) WO2001012579A2 (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2267255T3 (en) 1998-04-03 2007-03-01 Ajinomoto Co., Inc. ANTITUMOR AGENTS.
GB0019944D0 (en) 2000-08-15 2000-09-27 Angiogene Pharm Ltd Compositions with vascular damaging activity
CA2432640A1 (en) * 2000-12-21 2002-06-27 Cancer Research Technology Limited Substituted stilbenes, their reactions and anticancer activity
FR2838437B1 (en) 2002-04-11 2004-06-04 Aventis Pharma Sa PROCESSES FOR THE PREPARATION OF COMBRETASTATINS
GB0306908D0 (en) * 2003-03-26 2003-04-30 Angiogene Pharm Ltd Bioreductively activated stilbene prodrugs
KR20060115325A (en) * 2003-12-16 2006-11-08 지티엑스, 인코포레이티드 Prodrugs of selective androgen receptor modulators and methods of use thereof
CN1723884A (en) * 2004-07-21 2006-01-25 中国人民解放军军事医学科学院放射医学研究所 Cis-1, the diphenyl ethylene derivatives that 2-replaces are used to prepare the purposes of the medicine of treatment or prevent diabetes
CN101085743B (en) * 2006-06-06 2012-02-15 浙江大德药业集团有限公司 Fluorine-containing alkoxy combretastatin derivative, preparation method and use thereof
WO2009067706A1 (en) 2007-11-21 2009-05-28 Oxigene, Inc. Method for treating hematopoietic neoplasms
JP2011016777A (en) * 2009-07-10 2011-01-27 Nipro Corp New cysteine derivative
EP2609089A1 (en) 2010-08-27 2013-07-03 Universität des Saarlandes Selective 17beta-hydroxysteroid dehydrogenase type 1 inhibitors
US9353150B2 (en) 2012-12-04 2016-05-31 Massachusetts Institute Of Technology Substituted pyrazino[1′,2′:1 ,5]pyrrolo[2,3-b]-indole-1,4-diones for cancer treatment
CA2905509A1 (en) 2013-03-15 2014-09-18 Memorial Sloan-Kettering Cancer Center Hsp90-targeted cardiac imaging and therapy
EP3337495A4 (en) 2015-08-18 2019-04-10 Mateon Therapeutics, Inc. Use of vdas to enhance immunomodulating therapies against tumors
US10918627B2 (en) 2016-05-11 2021-02-16 Massachusetts Institute Of Technology Convergent and enantioselective total synthesis of Communesin analogs
US11932650B2 (en) 2017-05-11 2024-03-19 Massachusetts Institute Of Technology Potent agelastatin derivatives as modulators for cancer invasion and metastasis
US10640508B2 (en) 2017-10-13 2020-05-05 Massachusetts Institute Of Technology Diazene directed modular synthesis of compounds with quaternary carbon centers
CN113227398A (en) 2018-10-29 2021-08-06 塞弗德公司 Exponential-base-3 nucleic acid amplification with nested overlapping primers at reduced amplification time
WO2020247054A1 (en) 2019-06-05 2020-12-10 Massachusetts Institute Of Technology Compounds, conjugates, and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines and uses thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992016486A1 (en) * 1991-03-22 1992-10-01 Aston Molecules Limited Substituted diphenylethylenes and analogues or derivatives thereof
EP0641767A1 (en) * 1993-09-08 1995-03-08 Ajinomoto Co., Inc. Cytotoxic stilbene derivatives and pharmaceutical composition containing them
US5561122A (en) * 1994-12-22 1996-10-01 Arizona Board Of Regents Acting On Behalf Of Arizona State University Combretastatin A-4 prodrug
WO2000048590A1 (en) * 1999-02-16 2000-08-24 Angiogene Pharmaceuticals Ltd. Substituted stilbene compounds with vascular damaging activity

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992016486A1 (en) * 1991-03-22 1992-10-01 Aston Molecules Limited Substituted diphenylethylenes and analogues or derivatives thereof
EP0641767A1 (en) * 1993-09-08 1995-03-08 Ajinomoto Co., Inc. Cytotoxic stilbene derivatives and pharmaceutical composition containing them
US5561122A (en) * 1994-12-22 1996-10-01 Arizona Board Of Regents Acting On Behalf Of Arizona State University Combretastatin A-4 prodrug
WO2000048590A1 (en) * 1999-02-16 2000-08-24 Angiogene Pharmaceuticals Ltd. Substituted stilbene compounds with vascular damaging activity

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
J. A. WOODS: "The interaction with tubulin of a series of stilbenes based on combretastatin A-4", BRITISH JOURNAL OF CANCER, vol. 71, 1995, pages 705 - 711, XP000978556 *
K. OHSUMI: "Novel combretastatin analogues effective against murine solid tumors: design and structure-activity relationships", JOURNAL OF MEDICINAL CHEMISTRY, vol. 41, 1998, WASHINGTON US, pages 3022 - 3032, XP002102895 *
M. CUSHMAN: "Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization", JOURNAL OF MEDICINAL CHEMISTRY, vol. 34, 1991, WASHINGTON US, pages 2579 - 2588, XP000571676 *

Also Published As

Publication number Publication date
JP2003507356A (en) 2003-02-25
EP1206429A2 (en) 2002-05-22
NZ517069A (en) 2004-04-30
GB9918912D0 (en) 1999-10-13
CA2379544A1 (en) 2001-02-22
WO2001012579A2 (en) 2001-02-22

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