CA2210924A1 - Paclitaxel analogs, preparation and use as antitumor agents - Google Patents

Paclitaxel analogs, preparation and use as antitumor agents

Info

Publication number
CA2210924A1
CA2210924A1 CA002210924A CA2210924A CA2210924A1 CA 2210924 A1 CA2210924 A1 CA 2210924A1 CA 002210924 A CA002210924 A CA 002210924A CA 2210924 A CA2210924 A CA 2210924A CA 2210924 A1 CA2210924 A1 CA 2210924A1
Authority
CA
Canada
Prior art keywords
cephalomannine
dihalo
epi
preparation
dihalocephalomannine
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002210924A
Other languages
French (fr)
Other versions
CA2210924C (en
Inventor
Ramesh C. Pandey
Luben K. Yankov
Raghu Nair
Alex Poulev
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xechem Inc
Original Assignee
Individual
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
Priority claimed from US08/571,427 external-priority patent/US5840748A/en
Priority claimed from US08/672,397 external-priority patent/US5854278A/en
Priority claimed from US08/654,424 external-priority patent/US5807888A/en
Application filed by Individual filed Critical Individual
Publication of CA2210924A1 publication Critical patent/CA2210924A1/en
Application granted granted Critical
Publication of CA2210924C publication Critical patent/CA2210924C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Epoxy Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

The present invention provides novel paclitaxel analogs, specifically 2", 3" side-chain halogenated cephalomannine of the formula wherein, I. (2"R,3"S)-dihalocephalomannine II. (2"S,3"R)-dihalocephalomannine III. (2"R,3"S)-dihalo-7-epi-cephalomannine IV. (2"S,3"R)-dihalo-7-epi-cephalomannine (2"y 3"S)-dihalocephalomannine R1=H R2=OH

(2" R~3"R)-dihalocepha~omannine R ' Rt=OH Ri=H
(2"'S~3"S)-dihalo-7-epi-cephalomannine Rl-H RZnOH
(2"R,3"R)-dihalo-7-epi-cephalomannine R _ R~=H Ri=OH
CA002210924A 1995-12-13 1996-12-13 Paclitaxel analogs, preparation and use as antitumor agents Expired - Fee Related CA2210924C (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US08/571,427 US5840748A (en) 1995-10-02 1995-12-13 Dihalocephalomannine and methods of use therefor
US08/672,397 US5854278A (en) 1995-12-13 1996-05-29 Preparation of chlorinated paclitaxel analogues and use thereof as antitumor agents
US08/654,424 US5807888A (en) 1995-12-13 1996-05-29 Preparation of brominated paclitaxel analogues and their use as effective antitumor agents
US08/672,397 1996-05-29
US08/571,427 1996-05-29
US08/654,424 1996-05-29
PCT/US1996/019676 WO1997029098A1 (en) 1995-12-13 1996-12-13 Paclitaxel analogs, preparation and use as antitumor agents
ZA976833A ZA976833B (en) 1995-12-13 1997-07-31 Paclitaxel analogs preparation and use as antitumor agents

Publications (2)

Publication Number Publication Date
CA2210924A1 true CA2210924A1 (en) 1997-06-13
CA2210924C CA2210924C (en) 2004-03-02

Family

ID=27504891

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002210924A Expired - Fee Related CA2210924C (en) 1995-12-13 1996-12-13 Paclitaxel analogs, preparation and use as antitumor agents

Country Status (5)

Country Link
CN (1) CN100339373C (en)
AU (1) AU724929B2 (en)
BR (1) BR9607101A (en)
CA (1) CA2210924C (en)
WO (1) WO1997029098A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1701699A (en) * 1997-11-19 1999-06-07 Xechem International, Inc. Halogenated paclitaxel derivatives
CN100396286C (en) * 2002-12-30 2008-06-25 北京大学第一医院 Use of homoharringtonine and harringtonine in inhibiting vascularization
CN101074218B (en) * 2006-05-19 2013-01-16 中国医学科学院药物研究所 Cephalotamannine derivative, its production, its medicinal composition and use
CN103232464B (en) * 2013-03-29 2015-08-19 四川农业大学 Taxoid compound and preparation thereof and the application in cancer therapy drug
CN110585189B (en) * 2019-09-05 2022-12-30 广东艾时代生物科技有限责任公司 Application of cephalomannine in preparation of medicines for treating malaria

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5470866A (en) * 1992-08-18 1995-11-28 Virginia Polytechnic Institute And State University Method for the conversion of cephalomannine to taxol and for the preparation of n-acyl analogs of taxol

Also Published As

Publication number Publication date
CN1190964A (en) 1998-08-19
AU724929B2 (en) 2000-10-05
CA2210924C (en) 2004-03-02
BR9607101A (en) 1997-11-04
AU1461797A (en) 1997-08-28
CN100339373C (en) 2007-09-26
WO1997029098A1 (en) 1997-08-14

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Legal Events

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