EP2029563A4 - Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin iii - Google Patents
Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin iiiInfo
- Publication number
- EP2029563A4 EP2029563A4 EP07719967A EP07719967A EP2029563A4 EP 2029563 A4 EP2029563 A4 EP 2029563A4 EP 07719967 A EP07719967 A EP 07719967A EP 07719967 A EP07719967 A EP 07719967A EP 2029563 A4 EP2029563 A4 EP 2029563A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- iii
- docetaxel
- paclitaxel
- dihydro
- semi
- 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.)
- Withdrawn
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 2
- WPPPFZJNKLMYBW-FAEUQDRCSA-N 13-acetyl-9-dihydrobaccatin iii Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](OC(C)=O)[C@H](O)[C@]3(C)[C@@H](O)C[C@H]4OC[C@]4([C@H]31)OC(C)=O)C2(C)C)C)OC(=O)C)C(=O)C1=CC=CC=C1 WPPPFZJNKLMYBW-FAEUQDRCSA-N 0.000 title 1
- FFCWRLFQIKDRNO-UHFFFAOYSA-N 9-dihydro-13-acetyl baccatin III Natural products CC(=O)OC1C2C(O)CC(OC(=O)C)C3(CO3)C2C(OC(=O)C)C4(O)CC(OC(=O)C)C(=C(C1OC(=O)C)C4(C)C)C FFCWRLFQIKDRNO-UHFFFAOYSA-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
- 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)
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 route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin iii |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP2029563A4 (en) |
| WO (1) | WO2007143839A1 (en) |
Citations (2)
| 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)
| 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 |
| CA2231837A1 (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 |
| AU2004275881A1 (en) * | 2003-09-25 | 2005-04-07 | Tapestry Pharmaceuticals, Inc. | 9,10-alpha,alpha-OH-taxane analogs and methods for production thereof |
| US20090156828A1 (en) * | 2005-12-21 | 2009-06-18 | 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 active Search and Examination
Patent Citations (2)
| 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)
| 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 |
|---|---|
| EP2029563A1 (en) | 2009-03-04 |
| WO2007143839A1 (en) | 2007-12-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 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 |
|
| 17P | Request for examination filed |
Effective date: 20081212 |
|
| 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 |
|
| AX | Request for extension of the european patent |
Extension state: AL BA HR MK RS |
|
| A4 | Supplementary search report drawn up and despatched |
Effective date: 20091102 |
|
| 17Q | First examination report despatched |
Effective date: 20100318 |
|
| DAX | Request for extension of the european patent (deleted) | ||
| 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 |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20130323 |