ATE538110T1 - Herstellung von taxol und von docetaxel unter verwendung primärer amine - Google Patents
Herstellung von taxol und von docetaxel unter verwendung primärer amineInfo
- Publication number
- ATE538110T1 ATE538110T1 AT96907021T AT96907021T ATE538110T1 AT E538110 T1 ATE538110 T1 AT E538110T1 AT 96907021 T AT96907021 T AT 96907021T AT 96907021 T AT96907021 T AT 96907021T AT E538110 T1 ATE538110 T1 AT E538110T1
- Authority
- AT
- Austria
- Prior art keywords
- taxol
- primary amine
- docetaxel
- production
- imine
- Prior art date
Links
- 229960001592 paclitaxel Drugs 0.000 title abstract 6
- 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 abstract 4
- 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 abstract 3
- 229930012538 Paclitaxel Natural products 0.000 title abstract 3
- 229960003668 docetaxel Drugs 0.000 title abstract 3
- 150000003141 primary amines Chemical class 0.000 title 1
- -1 Taxol primary amine Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 150000002466 imines Chemical class 0.000 abstract 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 2
- 239000002028 Biomass Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- DBXFAPJCZABTDR-WBYYIXQISA-N cephalomannine Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](OC(C)=O)C(=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@H](O)[C@@H](NC(=O)C(/C)=C/C)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DBXFAPJCZABTDR-WBYYIXQISA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- BEHTXUBGUDGCNQ-IEAAAIHOSA-N taxol c Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](OC(C)=O)C(=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@H](O)[C@@H](NC(=O)CCCCC)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 BEHTXUBGUDGCNQ-IEAAAIHOSA-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)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/380,679 US5679807A (en) | 1995-01-30 | 1995-01-30 | Preparation of taxol and docetaxel through primary amines |
| PCT/US1996/001322 WO1996023780A1 (en) | 1995-01-30 | 1996-01-30 | Preparation of taxol and docetaxel through primary amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE538110T1 true ATE538110T1 (de) | 2012-01-15 |
Family
ID=23502073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT96907021T ATE538110T1 (de) | 1995-01-30 | 1996-01-30 | Herstellung von taxol und von docetaxel unter verwendung primärer amine |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5679807A (de) |
| EP (1) | EP0852581B1 (de) |
| JP (1) | JPH11502516A (de) |
| AT (1) | ATE538110T1 (de) |
| AU (1) | AU694627B2 (de) |
| CA (1) | CA2211799C (de) |
| WO (1) | WO1996023780A1 (de) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994018186A1 (en) | 1993-02-05 | 1994-08-18 | Bryn Mawr College | Synthesis of taxol, analogs and intermediates with variable a-ring side chains |
| US6002025A (en) * | 1999-02-24 | 1999-12-14 | Bcm Developement Inc. | Method for the purification of taxanes |
| JP4776843B2 (ja) | 1999-10-01 | 2011-09-21 | イムノゲン インコーポレーティッド | 免疫複合体及び化学療法剤を用いる癌治療用組成物及び方法 |
| US6452024B1 (en) | 2000-02-22 | 2002-09-17 | Chaichem Pharmaceuticals International | Process for extraction and purification of paclitaxel from natural sources |
| CA2410632A1 (en) | 2000-06-22 | 2001-12-27 | David S. Garvey | Nitrosated and nitrosylated taxanes, compositions and methods of use |
| WO2002076448A1 (en) * | 2001-03-23 | 2002-10-03 | Napro Biotherapeutics, Inc. | Molecular conjugates for use in treatment of cancer |
| AU2002340038A1 (en) * | 2001-10-05 | 2003-04-22 | University Of Toledo, The | Method for the selective removal of acyl-functionality attached to the 2'-hydroxy-group of paclitaxel-related derivatives |
| DE60323079D1 (de) * | 2002-04-05 | 2008-10-02 | Natural Pharmaceuticals Inc | Umwandlung von taxanmolekülen |
| EP2286827A1 (de) * | 2002-05-10 | 2011-02-23 | Agennix Incorporated | Lactoferrin in der Behandlung maligner Neoplasmen und anderer hyperproliferativer Erkrankungen |
| EP1537094B1 (de) * | 2002-08-04 | 2014-07-02 | Phyton Holdings, LLC | Verfahren zur Umwandlung von Taxanamiden in Paclitaxel oder andere Taxane |
| EP1599457A4 (de) * | 2003-02-04 | 2008-05-07 | Natural Pharmaceuticals Inc | Verfahren und zusammensetzung für die zubereitung einer verbindung mit einem im wesentlichen ringchlorierungsfreien benzoylierenden wirkstoff |
| US6759539B1 (en) | 2003-02-27 | 2004-07-06 | Chaichem Pharmaceuticals International | Process for isolation and purification of paclitaxel from natural sources |
| EP1947094A3 (de) * | 2003-12-12 | 2009-02-18 | Quiral Quimica Do Brasil | Herstellungsverfahren für Taxanderivate |
| CN100540544C (zh) * | 2004-02-24 | 2009-09-16 | 查塔姆生物技术有限公司 | 紫杉烷中间体和氮丙啶类似物的半合成及其向太平洋紫杉醇和多烯紫杉醇的转化 |
| US20050192445A1 (en) * | 2004-03-01 | 2005-09-01 | Phytogen Life Sciences Inc. | Semi-synthesis of taxane intermediates and aziridine analogues and their conversion to paclitaxel and docetaxel |
| US7585986B2 (en) * | 2004-02-24 | 2009-09-08 | Chatham Biotec, Limited | Semi-synthesis of taxane intermediates and aziridine analogues and their conversion to paclitaxel and docetaxel |
| US7838694B2 (en) * | 2004-04-23 | 2010-11-23 | Chatham Biotec, Limited | 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 |
| FR2882363B1 (fr) * | 2005-02-24 | 2007-05-11 | Seripharm | Procede de preparation du docetaxel |
| CN100374429C (zh) * | 2006-06-19 | 2008-03-12 | 昆明多希生物技术有限公司 | 以10-去乙酰紫杉醇为原料转化生产多烯紫杉醇的方法 |
| CA2686915A1 (en) * | 2008-12-04 | 2010-06-04 | Queen's University At Kingston | Schwartz reagents: methods of in situ generation and use |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2601676B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Procede de preparation du taxol et du desacetyl-10 taxol |
| US4876399A (en) * | 1987-11-02 | 1989-10-24 | Research Corporation Technologies, Inc. | Taxols, their preparation and intermediates thereof |
| US5015744A (en) * | 1989-11-14 | 1991-05-14 | Florida State University | Method for preparation of taxol using an oxazinone |
| MX9102128A (es) * | 1990-11-23 | 1992-07-08 | Rhone Poulenc Rorer Sa | Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene |
| US5319112A (en) * | 1992-08-18 | 1994-06-07 | Virgnia Tech Intellectual Properties, Inc. | Method for the conversion of cephalomannine to taxol and for the preparation of N-acyl analogs of taxol |
| FR2696458B1 (fr) * | 1992-10-05 | 1994-11-10 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
| US5356928A (en) * | 1992-11-06 | 1994-10-18 | Hauser Chemical Research, Inc. | Cytotoxic agents |
-
1995
- 1995-01-30 US US08/380,679 patent/US5679807A/en not_active Expired - Lifetime
-
1996
- 1996-01-30 AU AU50210/96A patent/AU694627B2/en not_active Expired
- 1996-01-30 CA CA2211799A patent/CA2211799C/en not_active Expired - Lifetime
- 1996-01-30 EP EP96907021A patent/EP0852581B1/de not_active Expired - Lifetime
- 1996-01-30 JP JP8523705A patent/JPH11502516A/ja active Pending
- 1996-01-30 WO PCT/US1996/001322 patent/WO1996023780A1/en not_active Ceased
- 1996-01-30 AT AT96907021T patent/ATE538110T1/de active
-
1997
- 1997-05-07 US US08/852,358 patent/US5808113A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU694627B2 (en) | 1998-07-23 |
| US5808113A (en) | 1998-09-15 |
| CA2211799A1 (en) | 1996-08-08 |
| WO1996023780A1 (en) | 1996-08-08 |
| EP0852581A1 (de) | 1998-07-15 |
| EP0852581B1 (de) | 2011-12-21 |
| AU5021096A (en) | 1996-08-21 |
| EP0852581A4 (de) | 1998-07-15 |
| CA2211799C (en) | 2010-04-27 |
| JPH11502516A (ja) | 1999-03-02 |
| US5679807A (en) | 1997-10-21 |
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