ATE409694T1 - Halbsynthetische darstellung von taxan- zwischenprodukten aus 9-dihydro-13-acetylbaccatin iii - Google Patents
Halbsynthetische darstellung von taxan- zwischenprodukten aus 9-dihydro-13-acetylbaccatin iiiInfo
- Publication number
- ATE409694T1 ATE409694T1 AT04796503T AT04796503T ATE409694T1 AT E409694 T1 ATE409694 T1 AT E409694T1 AT 04796503 T AT04796503 T AT 04796503T AT 04796503 T AT04796503 T AT 04796503T AT E409694 T1 ATE409694 T1 AT E409694T1
- Authority
- AT
- Austria
- Prior art keywords
- dihydro
- semi
- taxan
- acetylbaccatin iii
- iii
- Prior art date
Links
- 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 abstract 4
- 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 abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 3
- 239000013067 intermediate product Substances 0.000 title 1
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)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)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 abstract 2
- 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 abstract 2
- 229960003668 docetaxel Drugs 0.000 abstract 2
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 abstract 2
- HOJZAHQWDXAPDJ-UHFFFAOYSA-N 3-anilino-2-hydroxypropanoic acid Chemical group OC(=O)C(O)CNC1=CC=CC=C1 HOJZAHQWDXAPDJ-UHFFFAOYSA-N 0.000 abstract 1
- 229930012538 Paclitaxel Natural products 0.000 abstract 1
- 229940123237 Taxane Drugs 0.000 abstract 1
- 229930014667 baccatin III Natural products 0.000 abstract 1
- 125000003834 baccatin III group Chemical group 0.000 abstract 1
- 238000003780 insertion Methods 0.000 abstract 1
- 230000037431 insertion Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229960001592 paclitaxel Drugs 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 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 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/695,416 US7202370B2 (en) | 2003-10-27 | 2003-10-27 | Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE409694T1 true ATE409694T1 (de) | 2008-10-15 |
Family
ID=34549976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT04796503T ATE409694T1 (de) | 2003-10-27 | 2004-10-27 | Halbsynthetische darstellung von taxan- zwischenprodukten aus 9-dihydro-13-acetylbaccatin iii |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7202370B2 (de) |
| EP (2) | EP2003124B1 (de) |
| AT (1) | ATE409694T1 (de) |
| CA (1) | CA2583366C (de) |
| DE (1) | DE602004016888D1 (de) |
| TW (1) | TW200608958A (de) |
| WO (1) | WO2005044811A2 (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2598707A1 (en) * | 2004-02-24 | 2005-09-09 | Phytogen Life Sciences Inc. | Semi-synthesis of taxane intermediates and aziridine analogues and their conversion to paclitaxel and docetaxel |
| WO2005105767A1 (en) * | 2004-04-23 | 2005-11-10 | Chatham Biotec Ltd. | Semi-synthesis and isolation of taxane intermediates from a mixture of taxanes |
| US7893283B2 (en) * | 2004-06-04 | 2011-02-22 | Chatham Biotec, Limited | Semi-synthesis of taxane intermediates and their conversion to paclitaxel and docetaxel |
| US20050288520A1 (en) | 2004-06-25 | 2005-12-29 | Phytogen Life Sciences Inc. | One pot synthesis of taxane derivatives and their conversion to paclitaxel and docetaxel |
| US20050288521A1 (en) * | 2004-06-29 | 2005-12-29 | Phytogen Life Sciences Inc. | Semi-synthetic conversion of paclitaxel to docetaxel |
| US8415388B2 (en) * | 2005-02-22 | 2013-04-09 | Savvipharm Inc. | Pharmaceutical compositions containing paclitaxel orotate |
| US8263793B2 (en) * | 2005-03-31 | 2012-09-11 | Accord Healthcare Inc. | Preparation of taxanes from 9-dihydro-13-acetylbaccatin III |
| US7847111B2 (en) * | 2006-06-19 | 2010-12-07 | Canada Inc. | Semi-synthetic route for the preparation of paclitaxel, docetaxel, and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III |
| WO2008121476A1 (en) * | 2007-03-28 | 2008-10-09 | Tapestry Pharmaceuticals, Inc. | Biologically active taxane analogs and methods of treatment by oral administration |
| GB0701523D0 (en) * | 2007-01-26 | 2007-03-07 | Chatham Biotec Ltd | Semi-synthetic process for the preparation of taxane derivatives |
| CN101835769A (zh) * | 2007-08-22 | 2010-09-15 | 6570763加拿大有限公司 | 将9-二氢-13-乙酰基浆果赤霉素ⅲ转化为多烯紫杉醇或太平洋紫杉醇的方法 |
| CN101735179B (zh) * | 2008-11-19 | 2012-09-12 | 上海百灵医药科技有限公司 | 一种多烯紫杉醇的制备方法,其中间体及制备方法 |
| KR101096282B1 (ko) * | 2009-04-24 | 2011-12-20 | 주식회사 삼양제넥스 | 탁산 유도체를 제조하는 방법 |
| CN102408397B (zh) | 2011-10-19 | 2014-08-20 | 上海贝美医药科技有限公司 | 紫杉烷类衍生物及其制备方法 |
| CN104592173A (zh) * | 2014-12-31 | 2015-05-06 | 宁波绿之健药业有限公司 | 一种由9-dhb合成10-dab的制备方法 |
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| US34277A (en) * | 1862-01-28 | Improvement in lamps | ||
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| USRE34277E (en) | 1988-04-06 | 1993-06-08 | Centre National De La Recherche Scientifique | Process for preparing taxol |
| FR2629818B1 (fr) | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| FR2629819B1 (fr) | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
| US4960790A (en) | 1989-03-09 | 1990-10-02 | University Of Kansas | Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof |
| US5175315A (en) | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
| MY110249A (en) | 1989-05-31 | 1998-03-31 | Univ Florida State | Method for preparation of taxol using beta lactam |
| DE3927768A1 (de) * | 1989-08-23 | 1991-02-28 | Perkin Elmer Corp | Verfahren zur konzentrationsbestimmung mittels atomemissions-spektroskopie |
| US5136060A (en) | 1989-11-14 | 1992-08-04 | Florida State University | Method for preparation of taxol using an oxazinone |
| US5990325A (en) | 1993-03-05 | 1999-11-23 | Florida State University | Process for the preparation of 9-desoxotaxol, 9-desoxobaccatin III and analogs thereof |
| US5284864A (en) | 1991-09-23 | 1994-02-08 | Florida State University | Butenyl substituted taxanes and pharmaceutical compositions containing them |
| US5714513A (en) | 1991-09-23 | 1998-02-03 | Florida State University | C10 taxane derivatives and pharmaceutical compositions |
| US5430160A (en) | 1991-09-23 | 1995-07-04 | Florida State University | Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides |
| SG46582A1 (en) | 1991-09-23 | 1998-02-20 | Univ Florida State | 10-Desacetoxytaxol derivatives |
| US5654447A (en) | 1991-09-23 | 1997-08-05 | Florida State University | Process for the preparation of 10-desacetoxybaccatin III |
| US5489601A (en) | 1991-09-23 | 1996-02-06 | Florida State University | Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them |
| US5229526A (en) | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
| FR2687145B1 (fr) | 1992-02-07 | 1994-03-25 | Rhone Poulenc Rorer Sa | Nouveaux anhydrides d'acides, leur preparation et leur emplot et |
| US5200534A (en) | 1992-03-13 | 1993-04-06 | University Of Florida | Process for the preparation of taxol and 10-deacetyltaxol |
| US5416225A (en) | 1992-03-30 | 1995-05-16 | Sloan-Kettering Institute For Cancer Research | Total synthesis of taxol |
| US5254703A (en) | 1992-04-06 | 1993-10-19 | Florida State University | Semi-synthesis of taxane derivatives using metal alkoxides and oxazinones |
| JPH07505887A (ja) | 1992-04-17 | 1995-06-29 | アボツト・ラボラトリーズ | タキソール誘導体 |
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| WO1994005282A1 (en) | 1992-09-04 | 1994-03-17 | The Scripps Research Institute | Water soluble taxol derivatives |
| US5478854A (en) | 1992-10-01 | 1995-12-26 | Bristol-Myers Squibb Company | Deoxy taxols |
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| US5412116A (en) | 1992-11-06 | 1995-05-02 | Hauser Chemical Research, Inc. | Oxidation of glycoside substituted taxanes to taxol or taxol precursors and new taxane compounds formed as intermediates |
| FR2698363B1 (fr) | 1992-11-23 | 1994-12-30 | Rhone Poulenc Rorer Sa | Nouveaux dérivés du taxane, leur préparation et les compositions qui les contiennent. |
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| CA2204197A1 (en) | 1997-05-01 | 1998-11-01 | Jian Liu | Process for converting 9-dihydro-13-acetylbaccatin iii into taxol and derivatives thereof |
| ES2210451T3 (es) | 1997-05-02 | 2004-07-01 | Pharmachemie B.V. | Procedimiento de preparacion de baccatina iii y derivados de los mismos a partir de 10-desacetilbaccatina iii. |
| EP0933360A1 (de) | 1997-12-22 | 1999-08-04 | Pharmachemie B.V. | Synthese von Beta-lactamen |
| US5914411A (en) | 1998-01-21 | 1999-06-22 | Napro Biotherapeutics, Inc. | Alternate method for acylating 10-deacetylbaccatin III selectively at the C-10 position |
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| US6175023B1 (en) | 2000-01-31 | 2001-01-16 | Jian Liu | Synthesis of water soluble 9-dihydro-paclitaxel derivatives from 9-dihydro-13-acetylbaccatin III |
| US6229027B1 (en) | 2000-03-10 | 2001-05-08 | Jian Liu | Process for manufacturing paclitaxel and 13-acetyl-9-dihydrobaccatin IV |
-
2003
- 2003-10-27 US US10/695,416 patent/US7202370B2/en not_active Expired - Fee Related
-
2004
- 2004-09-07 TW TW093126988A patent/TW200608958A/zh unknown
- 2004-10-27 AT AT04796503T patent/ATE409694T1/de not_active IP Right Cessation
- 2004-10-27 CA CA2583366A patent/CA2583366C/en not_active Expired - Fee Related
- 2004-10-27 EP EP08165422.0A patent/EP2003124B1/de not_active Expired - Lifetime
- 2004-10-27 DE DE602004016888T patent/DE602004016888D1/de not_active Expired - Lifetime
- 2004-10-27 EP EP04796503A patent/EP1727810B1/de not_active Expired - Lifetime
- 2004-10-27 WO PCT/US2004/035583 patent/WO2005044811A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2003124A1 (de) | 2008-12-17 |
| US20050101789A1 (en) | 2005-05-12 |
| CA2583366A1 (en) | 2005-05-19 |
| WO2005044811A3 (en) | 2005-09-29 |
| EP1727810A2 (de) | 2006-12-06 |
| DE602004016888D1 (de) | 2008-11-13 |
| EP1727810B1 (de) | 2008-10-01 |
| TW200608958A (en) | 2006-03-16 |
| WO2005044811A2 (en) | 2005-05-19 |
| US7202370B2 (en) | 2007-04-10 |
| EP2003124B1 (de) | 2015-02-25 |
| CA2583366C (en) | 2012-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |