DE69618812T2 - Zwischerprodukte für die hemisynthese von taxanen und deren verfahren zu herstellung - Google Patents

Zwischerprodukte für die hemisynthese von taxanen und deren verfahren zu herstellung

Info

Publication number
DE69618812T2
DE69618812T2 DE69618812T DE69618812T DE69618812T2 DE 69618812 T2 DE69618812 T2 DE 69618812T2 DE 69618812 T DE69618812 T DE 69618812T DE 69618812 T DE69618812 T DE 69618812T DE 69618812 T2 DE69618812 T2 DE 69618812T2
Authority
DE
Germany
Prior art keywords
hemisynthesis
taxans
production
intermediate products
taxane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
DE69618812T
Other languages
English (en)
Other versions
DE69618812D1 (de
Inventor
Luc Chanteloup
Bruno Chauveau
Christine Corbin
Robert Dhal
Guen Sonia Le
Arnaud Lamy
Antoine Leze
Jean-Pierre Robin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe dEtude et de Recherche en Ingenierie Pharmaceutique SAS SERIPHARM
Original Assignee
Societe dEtude et de Recherche en Ingenierie Pharmaceutique SAS SERIPHARM
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Societe dEtude et de Recherche en Ingenierie Pharmaceutique SAS SERIPHARM filed Critical Societe dEtude et de Recherche en Ingenierie Pharmaceutique SAS SERIPHARM
Application granted granted Critical
Publication of DE69618812D1 publication Critical patent/DE69618812D1/de
Publication of DE69618812T2 publication Critical patent/DE69618812T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/64Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/87Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18Oxygen atoms
    • C07D263/20Oxygen atoms attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18Oxygen atoms
    • C07D263/20Oxygen atoms attached in position 2
    • C07D263/26Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/48Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D305/00Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0834Compounds having one or more O-Si linkage
    • C07F7/0838Compounds with one or more Si-O-Si sequences
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • C07F7/1872Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epoxy Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
DE69618812T 1995-10-27 1996-10-25 Zwischerprodukte für die hemisynthese von taxanen und deren verfahren zu herstellung Expired - Lifetime DE69618812T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9512739A FR2740451B1 (fr) 1995-10-27 1995-10-27 Nouveaux intermediaires pour l'hemisynthese de taxanes, leurs procedes de preparation et leur utilisation dans la synthese generale des taxanes
PCT/FR1996/001676 WO1997015562A1 (fr) 1995-10-27 1996-10-25 Intermediaires pour l'hemisynthese de taxanes et leurs procedes de preparation

Publications (2)

Publication Number Publication Date
DE69618812D1 DE69618812D1 (de) 2002-03-14
DE69618812T2 true DE69618812T2 (de) 2002-08-29

Family

ID=9484016

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69618812T Expired - Lifetime DE69618812T2 (de) 1995-10-27 1996-10-25 Zwischerprodukte für die hemisynthese von taxanen und deren verfahren zu herstellung

Country Status (25)

Country Link
US (5) US6265587B1 (de)
EP (1) EP0863887B1 (de)
JP (1) JP2000500437A (de)
KR (1) KR100489865B1 (de)
CN (1) CN100374428C (de)
AT (1) ATE212342T1 (de)
AU (1) AU710314B2 (de)
BR (1) BR9610908A (de)
CZ (1) CZ125598A3 (de)
DE (1) DE69618812T2 (de)
DK (1) DK0863887T3 (de)
EE (1) EE03610B1 (de)
ES (1) ES2170876T3 (de)
FR (1) FR2740451B1 (de)
GE (1) GEP20001938B (de)
HU (1) HU225507B1 (de)
IL (1) IL155876A (de)
NO (1) NO981823D0 (de)
NZ (1) NZ320356A (de)
PL (1) PL327458A1 (de)
PT (1) PT863887E (de)
RU (1) RU2159237C2 (de)
SK (1) SK52398A3 (de)
TR (1) TR199800713T2 (de)
WO (1) WO1997015562A1 (de)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2740451B1 (fr) * 1995-10-27 1998-01-16 Seripharm Nouveaux intermediaires pour l'hemisynthese de taxanes, leurs procedes de preparation et leur utilisation dans la synthese generale des taxanes
KR100225535B1 (ko) * 1996-08-27 1999-10-15 정지석 파클리탁셀의 제조방법
US6150537A (en) 1997-12-12 2000-11-21 Emory University Methods for the esterification of alcohols and compounds useful therefor as potential anticancer agents
KR100267596B1 (ko) * 1998-04-17 2000-10-16 강재헌 베타-아미노-알파-하이드록시산과 균등한 옥사졸린 유도체의 입체선택적 합성방법
US6143900A (en) * 1999-10-26 2000-11-07 Dong Kook Pharmaceutical Co., Ltd. Stereoselective synthesis of oxazoline derivative
ES2178539B1 (es) * 2000-03-14 2004-08-01 Dong Kook Pharmaceutical Co., Ltd. Procedimiento para la preparacion de un compuesto de oxazolina.
WO2002066448A1 (en) * 2001-02-20 2002-08-29 Dabur India Limited Method of preparation of paclitaxel (taxol) using 3-(alk-2-ynyloxy) carbonyl-5-oxazolidine carboxylic acid
FR2846327B1 (fr) * 2002-10-25 2006-03-24 Merck Sante Sas Derives de n-benzodioxolyl, n-benzodioxanyl et n-benzodioxepinyl arylcarboxamides utilisables dans le traitement de dyslipidemies et compositions pharmaceutiques les contenant.
BRPI0611771A2 (pt) * 2005-06-10 2011-12-20 Univ Florida State Res Found processos para a preparação de paclitaxel
US7667055B2 (en) 2005-06-10 2010-02-23 Florida State University Research Foundation, Inc. Processes for the production of polycyclic fused ring compounds
GB0701523D0 (en) * 2007-01-26 2007-03-07 Chatham Biotec Ltd Semi-synthetic process for the preparation of taxane derivatives
CN101468974B (zh) * 2007-12-28 2011-02-09 上海百灵医药科技有限公司 多烯紫杉醇的半合成方法
RU2014146265A (ru) 2009-12-30 2015-07-10 Басф Фарма (Калланиш) Лимитед Способ хроматографического разделения с псевдодвижущимся слоем
GB201111595D0 (en) 2011-07-06 2011-08-24 Equateq Ltd Improved process
GB201111589D0 (en) 2011-07-06 2011-08-24 Equateq Ltd New modified process
GB201111601D0 (en) 2011-07-06 2011-08-24 Equateq Ltd New process
GB201111591D0 (en) 2011-07-06 2011-08-24 Equateq Ltd Further new process
GB201111594D0 (en) 2011-07-06 2011-08-24 Equateq Ltd New improved process
CN103508918B (zh) * 2012-06-18 2015-09-09 上海医药工业研究院 带有环丁基的α-羟基β-氨基酯类化合物及其制备方法
GB201300354D0 (en) 2013-01-09 2013-02-20 Basf Pharma Callanish Ltd Multi-step separation process
US9428711B2 (en) 2013-05-07 2016-08-30 Groupe Novasep Chromatographic process for the production of highly purified polyunsaturated fatty acids
US8802880B1 (en) 2013-05-07 2014-08-12 Group Novasep Chromatographic process for the production of highly purified polyunsaturated fatty acids
EP2883860B1 (de) 2013-12-11 2016-08-24 Novasep Process Chromatografisches Verfahren zur Herstellung von mehrfach ungesättigten Fettsäuren
EP3092218B1 (de) 2014-01-07 2022-03-09 Novasep Process Solutions Verfahren zur reinigung von aminosäuren
CN107848990B (zh) * 2015-07-07 2021-06-11 万代忠胜 紫杉醇和多烯紫杉醇的侧链前体的制造方法
CN112876503B (zh) * 2021-03-18 2022-04-29 中国科学院兰州化学物理研究所 用于癌症硼中子俘获治疗药物的硼酸盐化合物及其制备
CN114195820B (zh) * 2021-12-17 2023-11-10 中山大学 异丝氨酸衍生物及其制备与在紫杉醇合成中的应用

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4876399A (en) * 1987-11-02 1989-10-24 Research Corporation Technologies, Inc. Taxols, their preparation and intermediates thereof
US5008411A (en) * 1988-05-24 1991-04-16 Hoffmann-La Roche Inc. Glycidic acid ester and process of preparation
US5274300A (en) * 1988-10-26 1993-12-28 Sepracor, Inc. Enzymatic hydrolysis of glycidate esters in the presence of bisulfite anion
CA2023645C (fr) * 1989-08-23 2002-03-26 Jean-Noel Denis Procede pour la preparation enantioselective de derives de la phenylisoserine
US5304670A (en) 1989-08-23 1994-04-19 Centre National De La Recherche Scientifique Process for the enantioselective preparation of phenylisoserine derivatives
JPH088879B2 (ja) * 1989-09-13 1996-01-31 田辺製薬株式会社 光学活性3―フェニルグリシッド酸エステル類化合物の製法
FR2658513B1 (fr) * 1990-02-21 1994-02-04 Rhone Poulenc Sante Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r).
FR2678930B1 (fr) 1991-07-10 1995-01-13 Rhone Poulenc Rorer Sa Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii.
WO1993010076A1 (en) * 1991-11-22 1993-05-27 The University Of Mississippi Synthesis and optical resolution of the taxol side chain and related compounds
PL186176B1 (pl) * 1992-12-23 2003-11-28 Bristol Myers Squibb Co Sposób wytwarzania zawierającego oksazolinowy łańcuch boczny taksanu, zwierający łańcuch boczny taksan, oksazolinowy związek, sposób wytwarzania związku oksazolinowego, sposób wytwarzania zawierającego łańcuch boczny taksanu, pochodna taksanu, prekursor paklitakselu, sposób wytwarzania bakatyny, sposób wytwarzania paklitakselu i pochodna bakatyny
FR2740451B1 (fr) * 1995-10-27 1998-01-16 Seripharm Nouveaux intermediaires pour l'hemisynthese de taxanes, leurs procedes de preparation et leur utilisation dans la synthese generale des taxanes
US6228955B1 (en) * 1996-04-19 2001-05-08 Chirotech Technology, Ltd. Asymmetric epoxides, their synthesis and use

Also Published As

Publication number Publication date
US20040220256A1 (en) 2004-11-04
PL327458A1 (en) 1998-12-07
AU710314B2 (en) 1999-09-16
CZ125598A3 (cs) 1998-08-12
NZ320356A (en) 2000-01-28
BR9610908A (pt) 1999-07-13
US20070208185A1 (en) 2007-09-06
KR19990067124A (ko) 1999-08-16
DK0863887T3 (da) 2002-04-22
ATE212342T1 (de) 2002-02-15
IL155876A (en) 2008-07-08
US6825365B2 (en) 2004-11-30
KR100489865B1 (ko) 2006-01-27
HUP9802487A2 (hu) 1999-09-28
PT863887E (pt) 2002-07-31
RU2159237C2 (ru) 2000-11-20
NO981823L (no) 1998-04-23
AU7308696A (en) 1997-05-15
US20020068833A1 (en) 2002-06-06
FR2740451B1 (fr) 1998-01-16
HUP9802487A3 (en) 2000-07-28
WO1997015562A1 (fr) 1997-05-01
US20050222089A1 (en) 2005-10-06
ES2170876T3 (es) 2002-08-16
JP2000500437A (ja) 2000-01-18
CN1200731A (zh) 1998-12-02
EP0863887A1 (de) 1998-09-16
NO981823D0 (no) 1998-04-23
TR199800713T2 (xx) 1998-09-21
GEP20001938B (en) 2000-02-05
SK52398A3 (en) 1998-09-09
EE03610B1 (et) 2002-02-15
US7279586B2 (en) 2007-10-09
EP0863887B1 (de) 2002-01-23
FR2740451A1 (fr) 1997-04-30
CN100374428C (zh) 2008-03-12
US7220871B2 (en) 2007-05-22
US7432383B2 (en) 2008-10-07
DE69618812D1 (de) 2002-03-14
EE9800149A (et) 1998-12-15
HU225507B1 (en) 2007-01-29
US6265587B1 (en) 2001-07-24

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Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8328 Change in the person/name/address of the agent

Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN

8328 Change in the person/name/address of the agent

Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC