NO20074860L - Fremgangsmate for fremstilling av paclitaxel - Google Patents
Fremgangsmate for fremstilling av paclitaxelInfo
- Publication number
- NO20074860L NO20074860L NO20074860A NO20074860A NO20074860L NO 20074860 L NO20074860 L NO 20074860L NO 20074860 A NO20074860 A NO 20074860A NO 20074860 A NO20074860 A NO 20074860A NO 20074860 L NO20074860 L NO 20074860L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- paclitaxel
- oxazolidine
- hydroxy
- iii
- Prior art date
Links
- 229930012538 Paclitaxel Natural products 0.000 title abstract 4
- 229960001592 paclitaxel Drugs 0.000 title abstract 4
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- 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 3
- 230000001681 protective effect Effects 0.000 abstract 3
- 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 abstract 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 2
- 230000008025 crystallization Effects 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 150000004579 taxol derivatives Chemical class 0.000 abstract 2
- YWLXLRUDGLRYDR-UHFFFAOYSA-N 10-deacetylbaccatin Chemical compound CC(=O)OC12COC1CC(O)C(C(C(O)C1=C(C)C(O)CC3(O)C1(C)C)=O)(C)C2C3OC(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-UHFFFAOYSA-N 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 238000000746 purification Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Fremgangsmåte for fremstilling av paclitaxel, karakterisert ved at det utføres fra 10-deacetylbaccatin ifølge en "en-kammer"-reaksjon omfattende de følgende 3 fortløpende trinnene: a) beskyttelse av et hydroksyradikal i stiling -7 av 10-DAB med et silylradikal, deretter b) acetylering av hydroksyradikalet i stilling -10, c) eventuelt krystallisering av det oppnådde baccatin III-derivatet, etterfulgt av kondenseringen av (4S,5R)-3-N-benzoyl-2RS-metoksy-4-fenyl-l,3- oksazolidin-5-karboksylsyren, ved forestring i stilling -13 av 10-acetylderivatet av baccatin III oppnådd tidligere, deretter åpning av oksazolidin av den cykliske laterale kjeden og samtidig frigjøring av hydroksyradikalet i stilling -7, av dets beskyttende radikal og eventuell rensing av oppnådd paclitaxel.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0501838A FR2882362B1 (fr) | 2005-02-23 | 2005-02-23 | Procede de preparation du paclitaxel |
| PCT/FR2006/000387 WO2006090057A1 (fr) | 2005-02-23 | 2006-02-21 | Procede de preparation du paclitaxel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO20074860L true NO20074860L (no) | 2007-11-20 |
Family
ID=35079381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20074860A NO20074860L (no) | 2005-02-23 | 2007-09-24 | Fremgangsmate for fremstilling av paclitaxel |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7563914B2 (no) |
| EP (1) | EP1856081B1 (no) |
| JP (1) | JP2008531528A (no) |
| KR (1) | KR20070108181A (no) |
| CN (1) | CN101128448A (no) |
| AT (1) | ATE491699T1 (no) |
| AU (1) | AU2006217804A1 (no) |
| BR (1) | BRPI0608015A2 (no) |
| CA (1) | CA2597174A1 (no) |
| DE (1) | DE602006018873D1 (no) |
| FR (1) | FR2882362B1 (no) |
| IL (1) | IL185278A0 (no) |
| MX (1) | MX2007010271A (no) |
| NO (1) | NO20074860L (no) |
| RU (1) | RU2007134453A (no) |
| WO (1) | WO2006090057A1 (no) |
| ZA (1) | ZA200706798B (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0618176D0 (en) * | 2006-09-15 | 2006-10-25 | Chatham Biotech Ltd | One pot synthesis of taxane derivatives and their conversion to paclitaxel and docetaxel |
| GB0701523D0 (en) * | 2007-01-26 | 2007-03-07 | Chatham Biotec Ltd | Semi-synthetic process for the preparation of taxane derivatives |
| CA2723654A1 (en) * | 2008-05-07 | 2009-11-12 | Ivax Research, Llc | Processes for preparation of taxanes and intermediates thereof |
| KR101378537B1 (ko) * | 2011-09-30 | 2014-03-28 | 주식회사 삼양바이오팜 | 10-디아세틸파클리탁셀로부터 파클리탁셀을 제조하는 방법 |
| CN103130753B (zh) * | 2013-03-14 | 2015-09-02 | 上海龙翔生物医药开发有限公司 | 抗肿瘤药物紫杉醇的半合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US622053A (en) * | 1899-03-28 | John w | ||
| FR2696459B1 (fr) | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
| CA2170661A1 (en) * | 1995-03-22 | 1996-09-23 | John K. Thottathil | Novel methods for the preparation of taxanes using oaxzolidine intermediates |
| CA2188190A1 (en) * | 1996-10-18 | 1998-04-18 | Sarala Balachandran | The semi-synthesis of a protected bacatin iii compound |
| HK1042302B (en) * | 1999-05-17 | 2004-10-08 | Bristol-Myers Squibb Company | Novel reaction conditions for the cleavage of silyl ethers in the preparation of paclitaxel (taxol) and paclitaxel analogues |
| 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 |
-
2005
- 2005-02-23 FR FR0501838A patent/FR2882362B1/fr not_active Expired - Fee Related
-
2006
- 2006-02-21 DE DE602006018873T patent/DE602006018873D1/de not_active Expired - Lifetime
- 2006-02-21 AT AT06709353T patent/ATE491699T1/de not_active IP Right Cessation
- 2006-02-21 WO PCT/FR2006/000387 patent/WO2006090057A1/fr not_active Ceased
- 2006-02-21 KR KR1020077019123A patent/KR20070108181A/ko not_active Withdrawn
- 2006-02-21 RU RU2007134453/04A patent/RU2007134453A/ru not_active Application Discontinuation
- 2006-02-21 CA CA002597174A patent/CA2597174A1/fr not_active Abandoned
- 2006-02-21 BR BRPI0608015-4A patent/BRPI0608015A2/pt not_active Application Discontinuation
- 2006-02-21 JP JP2007556633A patent/JP2008531528A/ja active Pending
- 2006-02-21 CN CNA2006800058985A patent/CN101128448A/zh active Pending
- 2006-02-21 US US11/816,857 patent/US7563914B2/en not_active Expired - Fee Related
- 2006-02-21 EP EP06709353A patent/EP1856081B1/fr not_active Expired - Lifetime
- 2006-02-21 MX MX2007010271A patent/MX2007010271A/es not_active Application Discontinuation
- 2006-02-21 AU AU2006217804A patent/AU2006217804A1/en not_active Abandoned
-
2007
- 2007-08-14 IL IL185278A patent/IL185278A0/en unknown
- 2007-08-15 ZA ZA200706798A patent/ZA200706798B/xx unknown
- 2007-09-24 NO NO20074860A patent/NO20074860L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20080207929A1 (en) | 2008-08-28 |
| ZA200706798B (en) | 2008-10-29 |
| JP2008531528A (ja) | 2008-08-14 |
| CA2597174A1 (fr) | 2006-08-31 |
| ATE491699T1 (de) | 2011-01-15 |
| EP1856081A1 (fr) | 2007-11-21 |
| BRPI0608015A2 (pt) | 2009-11-03 |
| WO2006090057A1 (fr) | 2006-08-31 |
| MX2007010271A (es) | 2008-03-10 |
| RU2007134453A (ru) | 2009-03-27 |
| DE602006018873D1 (de) | 2011-01-27 |
| AU2006217804A1 (en) | 2006-08-31 |
| IL185278A0 (en) | 2008-02-09 |
| EP1856081B1 (fr) | 2010-12-15 |
| US7563914B2 (en) | 2009-07-21 |
| CN101128448A (zh) | 2008-02-20 |
| FR2882362A1 (fr) | 2006-08-25 |
| FR2882362B1 (fr) | 2007-05-11 |
| KR20070108181A (ko) | 2007-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC2A | Withdrawal, rejection or dismissal of laid open patent application |