Title:
METHOD OF OBTAINING TAXOSTEROIDS AND PRECURSORS THEREOF
Document Type and Number:
WIPO Patent Application WO2005002496
Kind Code:
A3
Abstract:
The invention relates to a method of obtaining taxosteroids and the precursors thereof from hydrindane bicyclic systems. According to the invention, the compounds have a tetracyclic system which combines the structural characteristics of: taxanes, such as the bicyclic[5.3.1]undecane system (cycles A and B) which is fused to a ring with six members (C), and steroids, such as the CD-bicyclic system, the A ring and side chain (Sc). The invention also relates to the method of preparing said compounds and to the use thereof as compositions with beneficial pharmacological properties.
Inventors:
GRANJA GUILLAN JUAN (ES)
CASTEDO EXPOSITO LUIS (ES)
GARCIA FANDINO REBECA (ES)
CASTEDO EXPOSITO LUIS (ES)
GARCIA FANDINO REBECA (ES)
Application Number:
PCT/ES2004/000313
Publication Date:
March 10, 2005
Filing Date:
July 02, 2004
Export Citation:
Assignee:
UNIV SANTIAGO COMPOSTELA (ES)
GRANJA GUILLAN JUAN (ES)
CASTEDO EXPOSITO LUIS (ES)
GARCIA FANDINO REBECA (ES)
GRANJA GUILLAN JUAN (ES)
CASTEDO EXPOSITO LUIS (ES)
GARCIA FANDINO REBECA (ES)
International Classes:
C07J53/00; C07J63/00; C07J75/00; A61K; (IPC1-7): C07J63/00; C07J53/00; C07J75/00
Other References:
GARCIA-FANDINO R. ET AL.: "Tandem RCM of dienynes for the construction of taxol-type carbocyclic systems", ORGANIC LETTERS, vol. 6, no. 2, 2004, pages 193 - 196, XP002994682
LIU C. ET AL.: "Design, synthesis and bioactivities of steroid-linked Taxol analogues as potential targeted drugs for prostate and breast cancer", J. NAT. PROD., vol. 67, no. 2, 2004, pages 152 - 159, XP002995410
VERDIER-PINARD P. ET AL.: "A steroid derivative with Paclitaxel-like effects on tubulin polymerization", MOLECULAR PHARMACOLOGY, vol. 57, 2000, pages 568 - 575, XP000989650
VILLALVA-SERVIN N.P. ET AL.: "A direct carbometallation-stereoselective cycloaddition-ring closing metathesis route to the triciclic ABC core of taxoids", SYNLETT, vol. 9, 11 July 2003 (2003-07-11), pages 1263 - 1266, XP002994683
WANG Z. ET AL.: "Synthesis of B-ring homologated estradiol analogues that modulate tubulin polymerization and microtubule stability", J. MED. CHEM., vol. 43, no. 12, 2000, pages 2419 - 2429, XP002161895
CODESIDO E.M. ET AL.: "Towards an analogue of the transition state of PreD3-D3 isomerization: stereoselective synthesis of linearly fused 6-8-6 carbocyclic systems", ORG. LETT., vol. 4, no. 10, 2002, pages 1651 - 1654, XP002994684
OJIMA I. ET AL.: "Macrocycle formation by ring-closing metathesis. Application to the synthesis of novel mecrocyclic taxoids", J. AM. CHEM. SOC., vol. 122, no. 22, 2000, pages 5343 - 5353, XP000945956
LIU C. ET AL.: "Design, synthesis and bioactivities of steroid-linked Taxol analogues as potential targeted drugs for prostate and breast cancer", J. NAT. PROD., vol. 67, no. 2, 2004, pages 152 - 159, XP002995410
VERDIER-PINARD P. ET AL.: "A steroid derivative with Paclitaxel-like effects on tubulin polymerization", MOLECULAR PHARMACOLOGY, vol. 57, 2000, pages 568 - 575, XP000989650
VILLALVA-SERVIN N.P. ET AL.: "A direct carbometallation-stereoselective cycloaddition-ring closing metathesis route to the triciclic ABC core of taxoids", SYNLETT, vol. 9, 11 July 2003 (2003-07-11), pages 1263 - 1266, XP002994683
WANG Z. ET AL.: "Synthesis of B-ring homologated estradiol analogues that modulate tubulin polymerization and microtubule stability", J. MED. CHEM., vol. 43, no. 12, 2000, pages 2419 - 2429, XP002161895
CODESIDO E.M. ET AL.: "Towards an analogue of the transition state of PreD3-D3 isomerization: stereoselective synthesis of linearly fused 6-8-6 carbocyclic systems", ORG. LETT., vol. 4, no. 10, 2002, pages 1651 - 1654, XP002994684
OJIMA I. ET AL.: "Macrocycle formation by ring-closing metathesis. Application to the synthesis of novel mecrocyclic taxoids", J. AM. CHEM. SOC., vol. 122, no. 22, 2000, pages 5343 - 5353, XP000945956
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