EP2029563A4 - SEMI-SYNTHETIC PATHWAY FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL AND 10-DEACETYLBACCATINE III FROM 9-DIHYDRO-13-ACETYLBACCATINE III - Google Patents

SEMI-SYNTHETIC PATHWAY FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL AND 10-DEACETYLBACCATINE III FROM 9-DIHYDRO-13-ACETYLBACCATINE III

Info

Publication number: EP2029563A4
Authority: EP; European Patent Office
Prior art keywords: iii; docetaxel; paclitaxel; dihydro; semi
Prior art date: 2006-06-12
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP07719967A

Other languages

German (de)

French (fr)

Other versions

EP2029563A1 (en

Inventor

Liu Jian

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.)

6570763 Canada Inc

Original Assignee

6570763 Canada Inc

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.)

2006-06-12

Filing date

2007-06-12

Publication date

2009-12-02

2006-06-12 Priority claimed from CA002549951A external-priority patent/CA2549951A1/en

2006-06-19 Priority claimed from US11/425,034 external-priority patent/US7847111B2/en

2007-06-12 Application filed by 6570763 Canada Inc filed Critical 6570763 Canada Inc

2009-03-04 Publication of EP2029563A1 publication Critical patent/EP2029563A1/en

2009-12-02 Publication of EP2029563A4 publication Critical patent/EP2029563A4/en

Status Withdrawn legal-status Critical Current

Links

YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 title 1
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 title 1
229930012538 Paclitaxel Natural products 0.000 title 1
229960003668 docetaxel Drugs 0.000 title 1
229960001592 paclitaxel Drugs 0.000 title 1
230000037361 pathway Effects 0.000 title 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title 1

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
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

EP07719967A 2006-06-12 2007-06-12 SEMI-SYNTHETIC PATHWAY FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL AND 10-DEACETYLBACCATINE III FROM 9-DIHYDRO-13-ACETYLBACCATINE III Withdrawn EP2029563A4 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CA002549951A CA2549951A1 (en)	2006-06-12	2006-06-12	Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin iii
US11/425,034 US7847111B2 (en)	2006-06-19	2006-06-19	Semi-synthetic route for the preparation of paclitaxel, docetaxel, and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III
PCT/CA2007/001051 WO2007143839A1 (en)	2006-06-12	2007-06-12	Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin iii

Publications (2)

Publication Number	Publication Date
EP2029563A1 EP2029563A1 (en)	2009-03-04
EP2029563A4 true EP2029563A4 (en)	2009-12-02

Family

ID=38831365

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP07719967A Withdrawn EP2029563A4 (en)	2006-06-12	2007-06-12	SEMI-SYNTHETIC PATHWAY FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL AND 10-DEACETYLBACCATINE III FROM 9-DIHYDRO-13-ACETYLBACCATINE III

Country Status (2)

Country	Link
EP (1)	EP2029563A4 (en)
WO (1)	WO2007143839A1 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0400971A2 (en) *	1989-05-31	1990-12-05	Florida State University	Method for preparation of taxol
EP0428376A1 (en) *	1989-11-14	1991-05-22	Florida State University	Method for preparation of taxol using an oxazinone

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6593482B2 (en) *	1993-02-01	2003-07-15	Aventis Pharma S.A.	Methods for preparing new taxoids and pharmaceutical compositions containing them
US6710191B2 (en) *	1993-03-05	2004-03-23	Florida State University	9β-hydroxytetracyclic taxanes
IT1275936B1 (en) *	1995-03-17	1997-10-24	Indena Spa	DERIVATIVES OF 10-DEACETYLBACCATIN III AND OF 10-DEACETYL-14B- HYDROXYBACCATIN III THEIR METHOD OF PREPARATION AND FORMULATIONS
WO1997009979A1 (en) *	1995-09-13	1997-03-20	Florida State University	Radiosensitizing taxanes and their pharmaceutical preparations
CA2188190A1 (en) *	1996-10-18	1998-04-18	Sarala Balachandran	The semi-synthesis of a protected bacatin iii compound
CA2307548C (en) *	1997-05-01	2001-07-17	Jian Liu	Process for converting 9-dihydro-13-acetylbaccatin iii into taxol and derivatives thereof
US20010041803A1 (en) *	2000-03-21	2001-11-15	Kasitu Gertrude C.	Conversion of 9-dihydro-13-acetylbaccatin III to baccatin III and 10-deacetyl baccatin III
US6812356B2 (en) *	2002-09-26	2004-11-02	John Findlay	Conversion 9-dihydro-13-acetylbaccatin III into 10-deacetylbaccatin III
EP1785416A3 (en) *	2003-09-25	2007-05-30	Tapestry Pharmaceuticals, Inc.	9, 10-alpha, alpha-OH-Taxane Analogs and methods for production thereof
MX2008008120A (en) *	2005-12-21	2008-09-24	Tapestry Pharmaceuticals Inc	Novel compounds and methods for forming taxanes and using the same.

2007
- 2007-06-12 EP EP07719967A patent/EP2029563A4/en not_active Withdrawn
- 2007-06-12 WO PCT/CA2007/001051 patent/WO2007143839A1/en not_active Ceased

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0400971A2 (en) *	1989-05-31	1990-12-05	Florida State University	Method for preparation of taxol
EP0428376A1 (en) *	1989-11-14	1991-05-22	Florida State University	Method for preparation of taxol using an oxazinone

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
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 *
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 *
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 *
See also references of WO2007143839A1 *

Also Published As

Publication number	Publication date
WO2007143839A1 (en)	2007-12-21
EP2029563A1 (en)	2009-03-04

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Legal Events

Date	Code	Title	Description
2009-01-30	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
2009-03-04	17P	Request for examination filed	Effective date: 20081212
2009-03-04	AK	Designated contracting states	Kind code of ref document: A1 Designated state(s): 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
2009-03-04	AX	Request for extension of the european patent	Extension state: AL BA HR MK RS
2009-12-02	A4	Supplementary search report drawn up and despatched	Effective date: 20091102
2010-04-14	17Q	First examination report despatched	Effective date: 20100318
2012-08-08	DAX	Request for extension of the european patent (deleted)
2013-09-20	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN
2013-10-23	18D	Application deemed to be withdrawn	Effective date: 20130323