RU2008144391A - Способ получения производного таксана - Google Patents
Способ получения производного таксана Download PDFInfo
- Publication number
- RU2008144391A RU2008144391A RU2008144391/04A RU2008144391A RU2008144391A RU 2008144391 A RU2008144391 A RU 2008144391A RU 2008144391/04 A RU2008144391/04 A RU 2008144391/04A RU 2008144391 A RU2008144391 A RU 2008144391A RU 2008144391 A RU2008144391 A RU 2008144391A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- viii
- vii
- reaction
- carbonate
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 N-Boc-β-isobutylserinyl Chemical group 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 8
- 238000006243 chemical reaction Methods 0.000 claims abstract 6
- FNZPZCTVRVPPAB-YZSQHPIKSA-N 14beta-Hydroxy-10-deacetylbaccatin III Natural products O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)[C@H](O)[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 FNZPZCTVRVPPAB-YZSQHPIKSA-N 0.000 claims abstract 2
- 230000021736 acetylation Effects 0.000 claims abstract 2
- 238000006640 acetylation reaction Methods 0.000 claims abstract 2
- 239000003513 alkali Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 230000001681 protective effect Effects 0.000 claims abstract 2
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims abstract 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract 2
- 0 CC1(C)C([C@]2*C(C)=O)=C(C)C[C@@](CC(C3)O)[C@@]13C[C@@](C)(C1([C@@](C[Am]C(C)=O)C1C1)[C@]1C[C@@]1CC(*)=*)[C@]1(C)C2=O Chemical compound CC1(C)C([C@]2*C(C)=O)=C(C)C[C@@](CC(C3)O)[C@@]13C[C@@](C)(C1([C@@](C[Am]C(C)=O)C1C1)[C@]1C[C@@]1CC(*)=*)[C@]1(C)C2=O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1. Способ получения 13-(N-Boc-β-изобутилсеринил)-14β-гидроксибаккатин III-1,14-карбоната (I): ! ! который включает следующие стадии: ! а) ацетилирование 10-гидрокси группы 14β-гидрокси-10-дезацетилбаккатина III (IV) ! ! б) реакцию (V) с бис(трихлорметил)карбонатом с получением 1,14-карбонатного производного (VI) ! ! в) реакцию (VI) с трихлорацетилхлоридом с получением (VII) ! ! реакцию (VII) с (4S,5R)-N-Boc-2-(2,4-диметоксифенил)-4-изобутил-1-оксазолидин-5-карбоновой кислотой с получением (VIII) ! ! г) удаление щелочью защитной трихлорацетильной группы из соединения (VIII) ! ! д) удаление диметоксибензилиденовой защитной группы из соединения (IX) ! ! 2. Соединение формулы (VII): ! ! 3. Соединение формулы (VIII):
Claims (3)
1. Способ получения 13-(N-Boc-β-изобутилсеринил)-14β-гидроксибаккатин III-1,14-карбоната (I):
который включает следующие стадии:
а) ацетилирование 10-гидрокси группы 14β-гидрокси-10-дезацетилбаккатина III (IV)
б) реакцию (V) с бис(трихлорметил)карбонатом с получением 1,14-карбонатного производного (VI)
в) реакцию (VI) с трихлорацетилхлоридом с получением (VII)
реакцию (VII) с (4S,5R)-N-Boc-2-(2,4-диметоксифенил)-4-изобутил-1-оксазолидин-5-карбоновой кислотой с получением (VIII)
г) удаление щелочью защитной трихлорацетильной группы из соединения (VIII)
д) удаление диметоксибензилиденовой защитной группы из соединения (IX)
2. Соединение формулы (VII):
3. Соединение формулы (VIII):
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06009813.4 | 2006-05-12 | ||
| EP06009813A EP1854799B1 (en) | 2006-05-12 | 2006-05-12 | Process for the preparation of a taxane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008144391A true RU2008144391A (ru) | 2010-05-20 |
| RU2434014C2 RU2434014C2 (ru) | 2011-11-20 |
Family
ID=37708167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008144391/04A RU2434014C2 (ru) | 2006-05-12 | 2007-04-25 | Способ получения производного таксана |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1854799B1 (ru) |
| JP (1) | JP5154546B2 (ru) |
| KR (1) | KR101402122B1 (ru) |
| CN (1) | CN101448839B (ru) |
| AR (1) | AR061088A1 (ru) |
| AT (1) | ATE507231T1 (ru) |
| BR (1) | BRPI0711805B8 (ru) |
| CA (1) | CA2652008C (ru) |
| DE (1) | DE602006021546D1 (ru) |
| DK (1) | DK1854799T3 (ru) |
| ES (1) | ES2363524T3 (ru) |
| IL (1) | IL195220A (ru) |
| MX (1) | MX2008014447A (ru) |
| NO (1) | NO334210B1 (ru) |
| PE (1) | PE20080398A1 (ru) |
| RU (1) | RU2434014C2 (ru) |
| UY (1) | UY30341A1 (ru) |
| WO (1) | WO2007131601A1 (ru) |
| ZA (1) | ZA200809613B (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2389518T3 (es) | 2008-01-18 | 2012-10-26 | Indena S.P.A. | Formas sólidas de ortataxel |
| CN105985353B (zh) | 2015-02-11 | 2020-07-21 | 中国科学院上海药物研究所 | 一种化合物的a晶型及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0102407B1 (de) * | 1982-09-03 | 1986-02-19 | Wieland-Werke Ag | Rippenrohr mit inneren Vorsprüngen sowie Verfahren und Vorrichtung zu dessen Herstellung |
| DE3440141A1 (de) * | 1984-11-02 | 1986-05-07 | Heiner Dipl.-Chem. Dr. 8000 München Eckert | Verwendung von kohlensaeure-bis-trichlormethylester als proreagens fuer phosgen |
| KR100225535B1 (ko) * | 1996-08-27 | 1999-10-15 | 정지석 | 파클리탁셀의 제조방법 |
| ITMI991483A1 (it) * | 1999-07-06 | 2001-01-06 | Indena Spa | Derivati tassanici e procedimenti per la loro preparazione |
| IT1320107B1 (it) * | 2000-11-28 | 2003-11-18 | Indena Spa | Procedimento per la preparazione di derivati tassanici. |
| IT1319682B1 (it) * | 2000-12-06 | 2003-10-23 | Indena Spa | Procedimento di sintesi del paclitaxel. |
-
2006
- 2006-05-12 DK DK06009813.4T patent/DK1854799T3/da active
- 2006-05-12 DE DE602006021546T patent/DE602006021546D1/de active Active
- 2006-05-12 AT AT06009813T patent/ATE507231T1/de active
- 2006-05-12 EP EP06009813A patent/EP1854799B1/en not_active Not-in-force
- 2006-05-12 ES ES06009813T patent/ES2363524T3/es active Active
-
2007
- 2007-04-25 CA CA2652008A patent/CA2652008C/en not_active Expired - Fee Related
- 2007-04-25 BR BRPI0711805A patent/BRPI0711805B8/pt not_active IP Right Cessation
- 2007-04-25 JP JP2009508174A patent/JP5154546B2/ja not_active Expired - Fee Related
- 2007-04-25 WO PCT/EP2007/003643 patent/WO2007131601A1/en not_active Ceased
- 2007-04-25 MX MX2008014447A patent/MX2008014447A/es active IP Right Grant
- 2007-04-25 RU RU2008144391/04A patent/RU2434014C2/ru active
- 2007-04-25 CN CN200780017066XA patent/CN101448839B/zh not_active Expired - Fee Related
- 2007-04-25 KR KR1020087027590A patent/KR101402122B1/ko not_active Expired - Fee Related
- 2007-05-10 UY UY30341A patent/UY30341A1/es not_active Application Discontinuation
- 2007-05-10 AR ARP070102026A patent/AR061088A1/es active IP Right Grant
- 2007-05-10 PE PE2007000562A patent/PE20080398A1/es not_active Application Discontinuation
-
2008
- 2008-11-11 NO NO20084753A patent/NO334210B1/no not_active IP Right Cessation
- 2008-11-11 ZA ZA2008/09613A patent/ZA200809613B/en unknown
- 2008-11-11 IL IL195220A patent/IL195220A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| MX2008014447A (es) | 2008-11-26 |
| BRPI0711805B8 (pt) | 2021-05-25 |
| ZA200809613B (en) | 2010-02-24 |
| IL195220A0 (en) | 2009-08-03 |
| IL195220A (en) | 2014-03-31 |
| PE20080398A1 (es) | 2008-05-26 |
| ES2363524T3 (es) | 2011-08-08 |
| CN101448839A (zh) | 2009-06-03 |
| UY30341A1 (es) | 2007-11-30 |
| EP1854799A1 (en) | 2007-11-14 |
| WO2007131601A1 (en) | 2007-11-22 |
| NO334210B1 (no) | 2014-01-13 |
| ATE507231T1 (de) | 2011-05-15 |
| BRPI0711805B1 (pt) | 2020-09-24 |
| CN101448839B (zh) | 2011-09-21 |
| CA2652008A1 (en) | 2007-11-22 |
| BRPI0711805A2 (pt) | 2011-12-06 |
| JP2009536928A (ja) | 2009-10-22 |
| EP1854799B1 (en) | 2011-04-27 |
| DE602006021546D1 (de) | 2011-06-09 |
| DK1854799T3 (da) | 2011-07-18 |
| KR101402122B1 (ko) | 2014-05-30 |
| NO20084753L (no) | 2008-11-11 |
| HK1111985A1 (en) | 2008-08-22 |
| KR20090015923A (ko) | 2009-02-12 |
| CA2652008C (en) | 2014-12-30 |
| JP5154546B2 (ja) | 2013-02-27 |
| AR061088A1 (es) | 2008-08-06 |
| RU2434014C2 (ru) | 2011-11-20 |
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