EA199900096A1 - Способ ацилирования 10-деацетилбаккатина iii селективно в положение с-10 - Google Patents
Способ ацилирования 10-деацетилбаккатина iii селективно в положение с-10Info
- Publication number
- EA199900096A1 EA199900096A1 EA199900096A EA199900096A EA199900096A1 EA 199900096 A1 EA199900096 A1 EA 199900096A1 EA 199900096 A EA199900096 A EA 199900096A EA 199900096 A EA199900096 A EA 199900096A EA 199900096 A1 EA199900096 A1 EA 199900096A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- iii
- baccatin iii
- solution
- produce
- ether solvent
- Prior art date
Links
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)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Предлагается способ ацилирования 10-деацетилбаккатина III в положение С-10, не затрагивая гидрокси групп в положении С-7 с получением баккатина III, проводимый сначала растворением 10-деацетилбаккатина III в безводном эфирном растворителе, таком как тетрагидрофуран, при пониженной температуре, предпочтительно -78°С. Далее добавляют, по крайней мере, один эквивалент литиевого основания, предпочтительно примерно два эквивалента н-бутиллития, с последующим добавлением ацилирующего агента, такого как ацетилхлорид. Полученный раствор гасят, например, хлоридом аммония, для удаления избытка литиевого основания и ацилирующего агента. Результатом является баккатин III в растворе. Баккатин III может быть выделен удалением эфирного растворителя в вакууме с получением остатка, который может быть затем растворен, например, в этилацетате с промыванием полученного раствора для удаления нежелательных соединений солей. Для очистки баккатина III может применяться перекристаллизация или хроматография на колонке.Международная заявка была опубликована вместе с отчетом о международном поиске.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/678,759 US5750736A (en) | 1996-07-11 | 1996-07-11 | Method for acylating 10-deacetylbaccatin III selectively at the c-10 position |
| PCT/US1997/012307 WO1998002427A1 (en) | 1996-07-11 | 1997-07-09 | Method for acylating 10-deacetylbaccatin iii selectively at the c-10 position |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199900096A1 true EA199900096A1 (ru) | 1999-08-26 |
| EA002001B1 EA002001B1 (ru) | 2001-10-22 |
Family
ID=24724151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199900096A EA002001B1 (ru) | 1996-07-11 | 1997-07-09 | Способ ацилирования 10-деацетилбаккатина iii селективно в положение с-10 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5750736A (ru) |
| EP (1) | EP0918764B1 (ru) |
| JP (1) | JP2000514458A (ru) |
| KR (1) | KR20000023649A (ru) |
| CN (1) | CN1096453C (ru) |
| AT (1) | ATE266650T1 (ru) |
| AU (1) | AU731651B2 (ru) |
| BR (1) | BR9710234A (ru) |
| CA (1) | CA2259906A1 (ru) |
| DE (1) | DE69729100D1 (ru) |
| EA (1) | EA002001B1 (ru) |
| HK (1) | HK1019596A1 (ru) |
| IL (1) | IL127850A (ru) |
| NO (1) | NO986066L (ru) |
| NZ (1) | NZ333889A (ru) |
| WO (1) | WO1998002427A1 (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6005120A (en) | 1993-07-20 | 1999-12-21 | Florida State University | Tricyclic and tetracyclic taxanes |
| US7288665B1 (en) | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
| US5914411A (en) * | 1998-01-21 | 1999-06-22 | Napro Biotherapeutics, Inc. | Alternate method for acylating 10-deacetylbaccatin III selectively at the C-10 position |
| US6066749A (en) * | 1998-05-01 | 2000-05-23 | Napro Biotherapeutics, Inc. | Method for conversion of C-2'-O-protected-10-hydroxy taxol to c-2'-O-protected taxol:useful intermediates in paclitaxel synthesis |
| IL139316A0 (en) * | 1998-05-01 | 2001-11-25 | Napro Biotherapeutics Inc | Methods and intermediate compounds for preparing paclitaxel |
| US6143902A (en) * | 1999-06-21 | 2000-11-07 | Napro Biotherapeutics, Inc. | C-2 hydroxyl protected-N-acyl (2R,3S)-3-phenylisoserine N-imido activated esters and method for production thereof |
| US6136999A (en) * | 1999-06-21 | 2000-10-24 | Napro Biotherapeutics, Inc. | C-2 hydroxyl protected-n-acyl (2R,3S)-3-phenylisoserine substituted phenyl activated esters and method for production thereof |
| US6495705B2 (en) | 2000-03-16 | 2002-12-17 | Napro Biotherapeutics, Inc. | Efficient process for the production of 10-DAB III by selective hydrazinolysis of various taxanes |
| US6281368B1 (en) | 2000-03-16 | 2001-08-28 | Napro Biotherapeutics, Inc. | Simple and efficient hydrazinolysis of C-10 and C-13 ester functionalities of taxanes to obtain 10-DAB III |
| US6358996B1 (en) | 2000-06-09 | 2002-03-19 | Napro Biotherapeutics, Inc. | Stable isotope labeling of paclitaxel |
| AU2003273671A1 (en) * | 2002-10-09 | 2004-05-04 | Phytogen Life Sciences, Inc. | Novel taxanes and methods related to use and preparation thereof |
| US7202370B2 (en) * | 2003-10-27 | 2007-04-10 | Conor Medsystems, Inc. | Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5229526A (en) * | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
| IT1254517B (it) * | 1992-03-06 | 1995-09-25 | Indena Spa | 14-beta idrossi-10-deacetil-baccatina iii, suoi derivati, loro prepazione ed impiego terapeutico |
| FR2696463B1 (fr) * | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé d'obtention de la désacétyl-10 baccatine III. |
| FR2750989B1 (fr) * | 1996-07-09 | 1998-09-25 | Rhone Poulenc Rorer Sa | Procede de monoacylation d'hydroxy taxanes |
| ATE252569T1 (de) * | 1997-05-02 | 2003-11-15 | Pharmachemie Bv | Verfahren zur herstellung von baccatin iii und seiner derivate ausgehend von 10-deacetylbaccatin iii. |
| US7288665B1 (en) * | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
-
1996
- 1996-07-11 US US08/678,759 patent/US5750736A/en not_active Expired - Fee Related
-
1997
- 1997-07-09 EA EA199900096A patent/EA002001B1/ru not_active IP Right Cessation
- 1997-07-09 CA CA002259906A patent/CA2259906A1/en not_active Abandoned
- 1997-07-09 EP EP97934954A patent/EP0918764B1/en not_active Expired - Lifetime
- 1997-07-09 IL IL12785097A patent/IL127850A/en not_active IP Right Cessation
- 1997-07-09 DE DE69729100T patent/DE69729100D1/de not_active Expired - Lifetime
- 1997-07-09 JP JP10506245A patent/JP2000514458A/ja not_active Ceased
- 1997-07-09 BR BR9710234-2A patent/BR9710234A/pt unknown
- 1997-07-09 CN CN97196319A patent/CN1096453C/zh not_active Expired - Fee Related
- 1997-07-09 AT AT97934954T patent/ATE266650T1/de not_active IP Right Cessation
- 1997-07-09 WO PCT/US1997/012307 patent/WO1998002427A1/en active IP Right Grant
- 1997-07-09 NZ NZ333889A patent/NZ333889A/xx unknown
- 1997-07-09 AU AU38002/97A patent/AU731651B2/en not_active Ceased
-
1998
- 1998-12-22 NO NO986066A patent/NO986066L/no not_active Application Discontinuation
-
1999
- 1999-01-08 KR KR1019997000102A patent/KR20000023649A/ko not_active Application Discontinuation
- 1999-10-25 HK HK99104736A patent/HK1019596A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL127850A0 (en) | 1999-10-28 |
| EA002001B1 (ru) | 2001-10-22 |
| KR20000023649A (ko) | 2000-04-25 |
| BR9710234A (pt) | 2000-01-11 |
| EP0918764A1 (en) | 1999-06-02 |
| CA2259906A1 (en) | 1998-01-22 |
| JP2000514458A (ja) | 2000-10-31 |
| AU3800297A (en) | 1998-02-09 |
| NO986066L (no) | 1999-03-05 |
| WO1998002427A1 (en) | 1998-01-22 |
| ATE266650T1 (de) | 2004-05-15 |
| CN1225089A (zh) | 1999-08-04 |
| US5750736A (en) | 1998-05-12 |
| NZ333889A (en) | 1999-03-29 |
| DE69729100D1 (de) | 2004-06-17 |
| NO986066D0 (no) | 1998-12-22 |
| IL127850A (en) | 2001-11-25 |
| AU731651B2 (en) | 2001-04-05 |
| EP0918764B1 (en) | 2004-05-12 |
| EP0918764A4 (en) | 1999-09-01 |
| CN1096453C (zh) | 2002-12-18 |
| HK1019596A1 (en) | 2000-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA199900096A1 (ru) | Способ ацилирования 10-деацетилбаккатина iii селективно в положение с-10 | |
| US6133462A (en) | C-7 CBZ baccatin III and production method therefor | |
| EA200000782A1 (ru) | Альтернативный способ селективного ацилирования 10-деацетилбаккатина iii по 10-ому положению | |
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| EP1497276B1 (en) | Conversion of taxane molecules | |
| US5973170A (en) | C-7 metal alkoxides of baccatin III | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |