KR101146839B1 - 10-데아세틸-n-데벤조일-파클리탁셀의 반합성 제조 방법 - Google Patents
10-데아세틸-n-데벤조일-파클리탁셀의 반합성 제조 방법 Download PDFInfo
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- KR101146839B1 KR101146839B1 KR1020077007382A KR20077007382A KR101146839B1 KR 101146839 B1 KR101146839 B1 KR 101146839B1 KR 1020077007382 A KR1020077007382 A KR 1020077007382A KR 20077007382 A KR20077007382 A KR 20077007382A KR 101146839 B1 KR101146839 B1 KR 101146839B1
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- Prior art keywords
- deacetyl
- phenyl
- dimethoxyphenyl
- iii
- ester
- Prior art date
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
Description
* 케미칼 시프트(chemical shifts)는 외부표준(external standard)으로 테트라메틸실란(tetramethylsilane) 0 ppm에 관한 것이다.
* 케미칼 시프트(chemical shifts)는 외부표준(external standard)으로 테트라메틸실란(tetramethylsilane) 0 ppm에 관한 것이다.
Claims (16)
- 다음의 단계들로 구성된 10-데아세틸-N-데벤조일-파클리탁셀(10-deacetyl-N-debenzoyl-paclitaxel)(Ⅰ)의 제조 방법 :a) 2-(2,4-디메톡시페닐)-3-(2-니트로벤젠설페닐)-4(에스)-페닐-5(알)-옥사졸리딘카복실산(2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzensulfenyl)-4(S)-phenyl-5(R)-oxazolidine carboxylic acid)(V)을, 10-데아세틸-비스-7,10-트리클로로아세틸바카틴 Ⅲ(10-deacetiyl-bis-7,10-trichloroacetylbaccatin Ⅲ)(Ⅵ)와 반응시켜 2-(2,4-디메톡시페닐)-3-(2-니트로벤젠설페닐)-4(에스)-페닐-5(알)-옥사졸리딘카복실산, 10-데아세틸-7,10-비스-트리클로로아세틸바카틴 Ⅲ 13-일-에스테르(2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzenesulfenyl)-4(S)-phenyl-5(R)-oxazolidinecarboxylic acid, 10-deacetyl-7,10-bis-trichloroacetylbaccatin Ⅲ 13-yl-ester)(Ⅶ)을 얻고,b) 구조식(Ⅶ)의 화합물의 7-과 10- 위치의 트리클로로아세틸(trichloroacetyl) 그룹을 가수분해시켜 2-(2,4-디메톡시페닐)-3-(2-니트로벤젠설페닐)-4(에스)-페닐-5(알)-옥사졸리딘 카복실산, 10-데아세틸바카틴 Ⅲ 13-일-에스테르(2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzensulfenyl)-4(S)-phenyl-5(R)-oxazolidine carboxylic acid, 10-deacetylbaccatin Ⅲ 13-yl-ester)(Ⅷ)을 얻으며,c) 구조식(Ⅷ) 화합물을 산 처리하여 10-데아세틸-N-데벤조일-파클리탁셀(10-deacetyl-N-debenzoyl-paclitaxel)(Ⅰ)을 얻는다.
- 청구항 1에 있어서, a) 단계가 할로겐화된 지방족 용매(halogenated aliphatic solvent) 중에서 선택된 용매로 수행하는 제조 방법.
- 청구항 2에 있어서,할로겐화된 지방족 용매(halogenated aliphatic solvent)가 메틸렌 클로라이드(methylene chloride)인 제조 방법.
- 청구항 1 내지 3 중 어느 한 항에 있어서, a) 단계가 축합반응제(condensing agent)가 디사이클로헥실카보디이미드(dicyclohexylcarbodiiimide)이고, 활성화제(activating agent)가 4-디메틸아미노-피리딘(4-dimethylamino-pyridine) 존재 하에서 수행되는 제조 방법.
- 삭제
- 청구항 1 내지 3 중 어느 한 항에 있어서, b) 단계가 용매로 테트라하이드로푸란(tetrahydrofuran) 중 암모니움 하이드록사이드(ammonium hydroxide)로 수행되는 제조 방법.
- 청구항 1 내지 3 중 어느 한 항에 있어서, c) 단계가 수성 염산(aqueous hydrochloric acid)의 메탄올(methanol) 용액으로 수행되는 제조 방법.
- 삭제
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Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US61684004P | 2004-10-08 | 2004-10-08 | |
EP04425752A EP1647552A1 (en) | 2004-10-08 | 2004-10-08 | Semisynthesis process for the preparation of 10-deacetyl-n-debenzoyl-paclitaxel |
US60/616840 | 2004-10-08 | ||
EP04425752.5 | 2004-10-08 | ||
EP05007888A EP1712552A1 (en) | 2005-04-11 | 2005-04-11 | Semisynthesis process for the preparation of 10-deacetyl-n-debenzoyl-paclitaxel |
EP05007888.0 | 2005-04-11 | ||
PCT/EP2005/010822 WO2006037653A1 (en) | 2004-10-08 | 2005-10-07 | Semisynthesis process for the preparation of 10-deacetyl-n-debenzoyl-paclitaxel |
Related Child Applications (1)
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KR1020097007134A Division KR101216885B1 (ko) | 2004-10-08 | 2005-10-07 | 10-데아세틸-n-데벤조일-파클리탁셀의 반합성 제조 방법 |
Publications (2)
Publication Number | Publication Date |
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KR20070062533A KR20070062533A (ko) | 2007-06-15 |
KR101146839B1 true KR101146839B1 (ko) | 2012-05-16 |
Family
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KR1020097007134A KR101216885B1 (ko) | 2004-10-08 | 2005-10-07 | 10-데아세틸-n-데벤조일-파클리탁셀의 반합성 제조 방법 |
KR1020077007382A KR101146839B1 (ko) | 2004-10-08 | 2005-10-07 | 10-데아세틸-n-데벤조일-파클리탁셀의 반합성 제조 방법 |
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KR1020097007134A KR101216885B1 (ko) | 2004-10-08 | 2005-10-07 | 10-데아세틸-n-데벤조일-파클리탁셀의 반합성 제조 방법 |
Country Status (21)
Country | Link |
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US (3) | US7446126B2 (ko) |
EP (2) | EP2161260B1 (ko) |
JP (2) | JP4971169B2 (ko) |
KR (2) | KR101216885B1 (ko) |
CN (2) | CN101704804B (ko) |
AT (1) | ATE451360T1 (ko) |
AU (2) | AU2005291357B2 (ko) |
CA (2) | CA2582545C (ko) |
DE (1) | DE602005018238D1 (ko) |
DK (2) | DK1797059T3 (ko) |
ES (2) | ES2333738T3 (ko) |
HK (2) | HK1108317A1 (ko) |
IL (2) | IL182396A (ko) |
MX (1) | MX2007004157A (ko) |
NO (2) | NO339631B1 (ko) |
NZ (2) | NZ585629A (ko) |
PL (2) | PL2161260T3 (ko) |
PT (2) | PT2161260E (ko) |
RU (2) | RU2510395C2 (ko) |
SI (2) | SI1797059T1 (ko) |
WO (1) | WO2006037653A1 (ko) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7446126B2 (en) * | 2004-10-08 | 2008-11-04 | Indena S.P.A. | Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel |
ITMI20050614A1 (it) * | 2005-04-12 | 2006-10-13 | Indena Spa | Processo per la purificazione della 10-deacetilbaccatina iii dalla 10-deacetil-2-debenzoil-2-pentenoilbaccatina iii |
JP2009533330A (ja) * | 2006-03-21 | 2009-09-17 | ドクター レディズ ラボラトリーズ リミテッド | ドセタキセルの多形体およびプロセス |
PL210984B1 (pl) * | 2006-10-31 | 2012-03-30 | Inst Farmaceutyczny | Sposób wytwarzania docetakselu |
PL388144A1 (pl) | 2009-05-29 | 2010-12-06 | Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością | Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie |
KR101149600B1 (ko) * | 2009-12-31 | 2012-05-29 | 주식회사 삼양제넥스바이오 | 고순도 무수결정형 도세탁셀 제조방법 |
SG185389A1 (en) | 2010-05-03 | 2012-12-28 | Teikoku Pharma Usa Inc | Non-aqueous taxane pro-emulsion formulations and methods of making and using the same |
JO3685B1 (ar) | 2012-10-01 | 2020-08-27 | Teikoku Pharma Usa Inc | صيغ التشتيت الجسيمي للتاكسين غير المائي وطرق استخدامها |
WO2014200571A2 (en) | 2013-02-19 | 2014-12-18 | United Technologies Corporation | Composite attachment structure with 3d weave |
CN108822062B (zh) * | 2018-09-07 | 2020-08-28 | 无锡紫杉药业有限公司 | 一种多西他赛的精制方法 |
WO2020249507A1 (en) | 2019-06-11 | 2020-12-17 | Indena S.P.A. | Anhydrous crystalline form of cabazitaxel, a process for its preparation and pharmaceutical compositions containing it |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1992009589A1 (fr) * | 1990-11-23 | 1992-06-11 | Rhone-Poulenc Rorer S.A. | Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent |
WO1994007877A1 (fr) * | 1992-10-05 | 1994-04-14 | Rhone-Poulenc Rorer S.A. | Procede de preparation de derives du taxane |
US6500966B1 (en) * | 1999-03-02 | 2002-12-31 | Indena S.P.A. | Process for the preparation of taxanes from 10-deacetylbaccatin III |
US6737534B2 (en) * | 2000-11-28 | 2004-05-18 | Indena S.P.A. | Process for the preparation of taxan derivatives |
Family Cites Families (7)
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FR2718963B1 (fr) * | 1994-04-25 | 1996-05-24 | Rhone Poulenc Rorer Sa | Nouvelle composition pharmaceutique à base de taxoïdes. |
CA2170661A1 (en) * | 1995-03-22 | 1996-09-23 | John K. Thottathil | Novel methods for the preparation of taxanes using oaxzolidine intermediates |
IT1318678B1 (it) * | 2000-08-10 | 2003-08-27 | Indena Spa | Procedimento per la preparazione di derivati della baccatina iii. |
US6881852B2 (en) * | 2002-02-05 | 2005-04-19 | Dabur India Limited | Process of purification of paclitaxel and docetaxel |
ITMI20020782A1 (it) | 2002-04-12 | 2003-10-13 | Indena Spa | Processo semisintetico per la preparazione di n-debenzoilpaclitaxel |
PE20050206A1 (es) * | 2003-05-26 | 2005-03-26 | Schering Ag | Composicion farmaceutica que contiene un inhibidor de histona deacetilasa |
US7446126B2 (en) * | 2004-10-08 | 2008-11-04 | Indena S.P.A. | Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1992009589A1 (fr) * | 1990-11-23 | 1992-06-11 | Rhone-Poulenc Rorer S.A. | Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent |
WO1994007877A1 (fr) * | 1992-10-05 | 1994-04-14 | Rhone-Poulenc Rorer S.A. | Procede de preparation de derives du taxane |
US6500966B1 (en) * | 1999-03-02 | 2002-12-31 | Indena S.P.A. | Process for the preparation of taxanes from 10-deacetylbaccatin III |
US6737534B2 (en) * | 2000-11-28 | 2004-05-18 | Indena S.P.A. | Process for the preparation of taxan derivatives |
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