WO2008081247A3 - A process for the preparation of secotaxanes - Google Patents

A process for the preparation of secotaxanes Download PDF

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Publication number
WO2008081247A3
WO2008081247A3 PCT/IB2007/003951 IB2007003951W WO2008081247A3 WO 2008081247 A3 WO2008081247 A3 WO 2008081247A3 IB 2007003951 W IB2007003951 W IB 2007003951W WO 2008081247 A3 WO2008081247 A3 WO 2008081247A3
Authority
WO
WIPO (PCT)
Prior art keywords
secotaxanes
preparation
oxazolidine
dimethoxyphenyl
boc
Prior art date
Application number
PCT/IB2007/003951
Other languages
French (fr)
Other versions
WO2008081247A2 (en
Inventor
Gabriele Fontana
Ezio Bombardelli
Bruno Gabetta
Giovanni Appendino
Francesco Mainieri
Original Assignee
Indena Spa
Gabriele Fontana
Ezio Bombardelli
Bruno Gabetta
Giovanni Appendino
Francesco Mainieri
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 Indena Spa, Gabriele Fontana, Ezio Bombardelli, Bruno Gabetta, Giovanni Appendino, Francesco Mainieri filed Critical Indena Spa
Priority to AU2007341070A priority Critical patent/AU2007341070A1/en
Priority to CA002673238A priority patent/CA2673238A1/en
Priority to JP2009542257A priority patent/JP2010513459A/en
Priority to MX2009006581A priority patent/MX2009006581A/en
Priority to EP07859076A priority patent/EP2091931A2/en
Publication of WO2008081247A2 publication Critical patent/WO2008081247A2/en
Publication of WO2008081247A3 publication Critical patent/WO2008081247A3/en
Priority to NO20092337A priority patent/NO20092337L/en

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
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms 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 atoms
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Epoxy Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention discloses a process for the preparation of secotaxanes starting from 10-deacetylbaccatin III and (4S,5R)-N-Boc-2-(2,4- dimethoxyphenyl)-4-isobutyl-1 -oxazolidine-5-carboxylic acid.
PCT/IB2007/003951 2006-12-21 2007-12-17 A process for the preparation of secotaxanes WO2008081247A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2007341070A AU2007341070A1 (en) 2006-12-21 2007-12-17 A process for the preparation of secotaxanes
CA002673238A CA2673238A1 (en) 2006-12-21 2007-12-17 A process for the preparation of secotaxanes
JP2009542257A JP2010513459A (en) 2006-12-21 2007-12-17 Method for preparing secotaxane
MX2009006581A MX2009006581A (en) 2006-12-21 2007-12-17 A process for the preparation of secotaxanes.
EP07859076A EP2091931A2 (en) 2006-12-21 2007-12-17 A process for the preparation of secotaxanes
NO20092337A NO20092337L (en) 2006-12-21 2009-06-18 Process for the preparation of secotaxans

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI2006A002479 2006-12-21
IT002479A ITMI20062479A1 (en) 2006-12-21 2006-12-21 PROCESS FOR PREPARING SECOTASSANS

Publications (2)

Publication Number Publication Date
WO2008081247A2 WO2008081247A2 (en) 2008-07-10
WO2008081247A3 true WO2008081247A3 (en) 2008-10-09

Family

ID=39589051

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2007/003951 WO2008081247A2 (en) 2006-12-21 2007-12-17 A process for the preparation of secotaxanes

Country Status (11)

Country Link
EP (1) EP2091931A2 (en)
JP (1) JP2010513459A (en)
KR (1) KR20090092285A (en)
CN (1) CN101631782A (en)
AU (1) AU2007341070A1 (en)
CA (1) CA2673238A1 (en)
IT (1) ITMI20062479A1 (en)
MX (1) MX2009006581A (en)
NO (1) NO20092337L (en)
RU (1) RU2009123160A (en)
WO (1) WO2008081247A2 (en)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994007877A1 (en) * 1992-10-05 1994-04-14 Rhone-Poulenc Rorer S.A. Method of preparing taxane derivatives
WO1996003394A1 (en) * 1994-07-26 1996-02-08 Indena S.P.A. Semi-synthetic taxanes with anti-tumoural activity
US5965739A (en) * 1993-06-11 1999-10-12 Pharmacia & Upjohn Company Δ6,7 -taxols antineoplastic use and pharmaceutical compositions containing them
WO2000052003A1 (en) * 1999-03-02 2000-09-08 Indena S.P.A. A process for the preparation of taxanes from 10-deacetylbaccatin iii
WO2001002407A2 (en) * 1999-07-06 2001-01-11 Indena S.P.A. Taxane derivatives and processes for the preparation thereof
US20030229135A1 (en) * 2002-05-07 2003-12-11 Sharma Arun Prakash Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl)ethoxycarbonyl]-5-oxazolidine carboxylic acids
US20040073044A1 (en) * 2002-05-10 2004-04-15 Sharma Arun Prakash Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994007877A1 (en) * 1992-10-05 1994-04-14 Rhone-Poulenc Rorer S.A. Method of preparing taxane derivatives
US5965739A (en) * 1993-06-11 1999-10-12 Pharmacia & Upjohn Company Δ6,7 -taxols antineoplastic use and pharmaceutical compositions containing them
WO1996003394A1 (en) * 1994-07-26 1996-02-08 Indena S.P.A. Semi-synthetic taxanes with anti-tumoural activity
WO2000052003A1 (en) * 1999-03-02 2000-09-08 Indena S.P.A. A process for the preparation of taxanes from 10-deacetylbaccatin iii
WO2001002407A2 (en) * 1999-07-06 2001-01-11 Indena S.P.A. Taxane derivatives and processes for the preparation thereof
US20030229135A1 (en) * 2002-05-07 2003-12-11 Sharma Arun Prakash Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl)ethoxycarbonyl]-5-oxazolidine carboxylic acids
US20040073044A1 (en) * 2002-05-10 2004-04-15 Sharma Arun Prakash Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
APPENDINO G ET AL: "Synthesis and Evaluation of C-Seco Paclitaxel Analogues", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 38, no. 24, 16 June 1997 (1997-06-16), pages 4273 - 4276, XP004074809, ISSN: 0040-4039 *
APPENDINO G ET AL: "The Reductive Fragmentation of 7-Hydroxy-9,10-dioxotaxoids", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH VERLAG, WEINHEIM, DE, no. 22, 1 January 2003 (2003-01-01), pages 4422 - 4431, XP002395174, ISSN: 1434-193X *

Also Published As

Publication number Publication date
CA2673238A1 (en) 2008-07-10
KR20090092285A (en) 2009-08-31
RU2009123160A (en) 2010-12-27
EP2091931A2 (en) 2009-08-26
MX2009006581A (en) 2009-06-30
WO2008081247A2 (en) 2008-07-10
AU2007341070A1 (en) 2008-07-10
NO20092337L (en) 2009-07-14
JP2010513459A (en) 2010-04-30
CN101631782A (en) 2010-01-20
ITMI20062479A1 (en) 2008-06-22

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