Global Patent Index - EP 2029563 A4

EP 2029563 A4 20091202 - SEMI-SYNTHETIC ROUTE FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL AND 10-DEACETYLBACCATIN III FROM 9-DIHYDRO-13-ACETYLBACCATIN III

Title (en)

SEMI-SYNTHETIC ROUTE FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL AND 10-DEACETYLBACCATIN III FROM 9-DIHYDRO-13-ACETYLBACCATIN III

Title (de)

HALBSYNTHETISCHE ROUTE ZUR HERSTELLUNG VON PACLITAXEL, DOCETAXEL UND 10-DEACETYLBACCATIN III AUS 9-DIHYDRO-13-ACETYLBACCATIN III

Title (fr)

VOIE SEMI-SYNTHÉTIQUE POUR LA PRÉPARATION DE PACLITAXEL, DOCÉTAXEL ET 10-DÉSACÉTYLBACCATINE III À PARTIR DE 9-DIHYDRO-13-ACÉTYLBACCATINE III

Publication

EP 2029563 A4 20091202 (EN)

Application

EP 07719967 A 20070612

Priority

  • CA 2007001051 W 20070612
  • CA 2549951 A 20060612
  • US 42503406 A 20060619

Abstract (en)

[origin: WO2007143839A1] A novel semi-synthetic route has been provided in the preparation of docetaxel and paclitaxel. This new process involves the conversion of 9-dihydro-13-acetylbaccatinIII to docetaxel and paclitaxel by the step of converting 9-dihydro-13-acetylbaccatin III into 7-O-triethylsilyl-9,10-diketobaccatin III, and adding docetaxel and paclitaxel side chain precursors, respectively, to form a new class of taxane intermediates, such as 7-O-triethylsilyl-9,10-diketodocetaxel and 7-O-triethylsilyl-9,10-diketopaclitaxeltaxel. These new intermediates then by a series reduction, acetylation of the 10-hydroxyl position for paclitaxel and finally deprotection to yield docetaxel and paclitaxel, the most important anti-cancer drugs.

IPC 8 full level

C07D 305/14 (2006.01); C07F 7/18 (2006.01)

CPC (source: EP)

C07D 305/14 (2013.01); C07F 7/1804 (2013.01)

Citation (search report)

  • [X] EP 0400971 A2 19901205 - UNIV FLORIDA STATE [US]
  • [X] EP 0428376 A1 19910522 - UNIV FLORIDA STATE [US]
  • [X] DENIS J-N: "A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 110, no. 17, 1988, pages 5917 - 5920, XP000654163, ISSN: 0002-7863
  • [X] 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, XP002486097, ISSN: 1434-193X
  • See references of WO 2007143839A1

Citation (examination)

OJIMA I ET AL: "NEW AND EFFICIENT APPROACHES TO THE SEMISYNTHESIS OF TAXOL AND ITS C-13 SIDE CHAIN ANALOGS BY MEANS OF -LACTAM SYNTHON METHOD", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 48, no. 34, 21 August 1992 (1992-08-21), pages 6985 - 7012, XP000561212, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)91210-4

Designated contracting state (EPC)

AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR

DOCDB simple family (publication)

WO 2007143839 A1 20071221; EP 2029563 A1 20090304; EP 2029563 A4 20091202

DOCDB simple family (application)

CA 2007001051 W 20070612; EP 07719967 A 20070612