DE69424939D1 - Synthese von taxol und seinen derivaten - Google Patents

Synthese von taxol und seinen derivaten

Info

Publication number
DE69424939D1
DE69424939D1 DE69424939T DE69424939T DE69424939D1 DE 69424939 D1 DE69424939 D1 DE 69424939D1 DE 69424939 T DE69424939 T DE 69424939T DE 69424939 T DE69424939 T DE 69424939T DE 69424939 D1 DE69424939 D1 DE 69424939D1
Authority
DE
Germany
Prior art keywords
taxol
synthesis
derivatives
tricyclic
intermediates
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 - Fee Related
Application number
DE69424939T
Other languages
English (en)
Other versions
DE69424939T2 (de
Inventor
Robert A Holton
Carmen Somoza
Hyeong B Kim
Mitsuru Shindo
Ronald J Biediger
P Douglas Boatman
Chase Smith
Feng Liang
Krishna Murthi
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.)
Florida State University
Original Assignee
Florida State University
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 Florida State University filed Critical Florida State University
Application granted granted Critical
Publication of DE69424939D1 publication Critical patent/DE69424939D1/de
Publication of DE69424939T2 publication Critical patent/DE69424939T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • 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
DE69424939T 1993-07-20 1994-07-20 Synthese von taxol und seinen derivaten Expired - Fee Related DE69424939T2 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US9516193A 1993-07-20 1993-07-20
US13822993A 1993-10-15 1993-10-15
US08/189,058 US5405972A (en) 1993-07-20 1994-01-27 Synthetic process for the preparation of taxol and other tricyclic and tetracyclic taxanes
PCT/US1994/008350 WO1995003265A1 (en) 1993-07-20 1994-07-20 Synthesis of taxol and its derivatives

Publications (2)

Publication Number Publication Date
DE69424939D1 true DE69424939D1 (de) 2000-07-20
DE69424939T2 DE69424939T2 (de) 2000-11-02

Family

ID=27377903

Family Applications (2)

Application Number Title Priority Date Filing Date
DE69432569T Expired - Fee Related DE69432569T2 (de) 1993-07-20 1994-07-20 Synthese von Taxol und deren Derivate
DE69424939T Expired - Fee Related DE69424939T2 (de) 1993-07-20 1994-07-20 Synthese von taxol und seinen derivaten

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE69432569T Expired - Fee Related DE69432569T2 (de) 1993-07-20 1994-07-20 Synthese von Taxol und deren Derivate

Country Status (15)

Country Link
US (4) US5405972A (de)
EP (2) EP0710223B1 (de)
JP (2) JP3564135B2 (de)
KR (3) KR100353666B1 (de)
CN (1) CN1046261C (de)
AT (2) ATE238289T1 (de)
AU (1) AU687428B2 (de)
CA (1) CA2167718C (de)
DE (2) DE69432569T2 (de)
DK (2) DK0960881T3 (de)
ES (2) ES2198827T3 (de)
GR (1) GR3034343T3 (de)
PT (2) PT710223E (de)
SG (2) SG97813A1 (de)
WO (1) WO1995003265A1 (de)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
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US5998656A (en) * 1991-09-23 1999-12-07 Florida State University C10 tricyclic taxanes
US5714513A (en) * 1991-09-23 1998-02-03 Florida State University C10 taxane derivatives and pharmaceutical compositions
US5728725A (en) * 1991-09-23 1998-03-17 Florida State University C2 taxane derivaties and pharmaceutical compositions containing them
US5654447A (en) * 1991-09-23 1997-08-05 Florida State University Process for the preparation of 10-desacetoxybaccatin III
US6028205A (en) * 1991-09-23 2000-02-22 Florida State University C2 tricyclic taxanes
US5489601A (en) * 1991-09-23 1996-02-06 Florida State University Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them
US6794523B2 (en) 1991-09-23 2004-09-21 Florida State University Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
US5728850A (en) * 1991-09-23 1998-03-17 Florida State University Taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US6335362B1 (en) 1991-09-23 2002-01-01 Florida State University Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them
US5721268A (en) 1991-09-23 1998-02-24 Florida State University C7 taxane derivatives and pharmaceutical compositions containing them
US6005138A (en) 1991-09-23 1999-12-21 Florida State University Tricyclic taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US6495704B1 (en) 1991-09-23 2002-12-17 Florida State University 9-desoxotaxanes and process for the preparation of 9-desoxotaxanes
US5739362A (en) * 1991-09-23 1998-04-14 Florida State University Taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US6018073A (en) * 1991-09-23 2000-01-25 Florida State University Tricyclic taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US6011056A (en) 1991-09-23 2000-01-04 Florida State University C9 taxane derivatives and pharmaceutical compositions containing them
FR2698871B1 (fr) 1992-12-09 1995-02-24 Rhone Poulenc Rorer Sa Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
US5973160A (en) 1992-12-23 1999-10-26 Poss; Michael A. Methods for the preparation of novel sidechain-bearing taxanes
US6339164B1 (en) 1993-01-29 2002-01-15 Florida State University C2 substituted phenyl taxane derivatives and pharmaceutical compositions containing them
PT687260E (pt) * 1993-03-05 2003-07-31 Univ Florida State Processo para a preparacao de 9-desoxotaxanos
US6710191B2 (en) 1993-03-05 2004-03-23 Florida State University 9β-hydroxytetracyclic taxanes
US6005120A (en) 1993-07-20 1999-12-21 Florida State University Tricyclic and tetracyclic taxanes
FR2718137B1 (fr) * 1994-04-05 1996-04-26 Rhone Poulenc Rorer Sa Procédé de préparation de trialcoylsilyl-7 baccatine III.
DE4416374A1 (de) * 1994-05-05 1995-11-09 Schering Ag Neue Borneolderivate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung
US5508447A (en) * 1994-05-24 1996-04-16 Board Of Regents, The University Of Texas System Short synthetic route to taxol and taxol derivatives
US5677470A (en) * 1994-06-28 1997-10-14 Tanabe Seiyaku Co., Ltd. Baccatin derivatives and processes for preparing the same
CA2162759A1 (en) * 1994-11-17 1996-05-18 Kenji Tsujihara Baccatin derivatives and processes for preparing the same
US6545168B1 (en) * 1996-05-06 2003-04-08 Florida State University 1-deoxy baccatin III, 1-deoxy taxol and 1-deoxy taxol analogs and method for the preparation thereof
CA2188190A1 (en) 1996-10-18 1998-04-18 Sarala Balachandran The semi-synthesis of a protected bacatin iii compound
US7288665B1 (en) * 1997-08-18 2007-10-30 Florida State University Process for selective derivatization of taxanes
AU739303B2 (en) 1997-08-21 2001-10-11 Florida State University Method for the synthesis of taxanes
US6150537A (en) 1997-12-12 2000-11-21 Emory University Methods for the esterification of alcohols and compounds useful therefor as potential anticancer agents
US6156789A (en) * 1998-03-17 2000-12-05 Rhone-Poulenc Rorer S.A. Method for treating abnormal cell proliferation in the brain
CA2385528C (en) 1999-10-01 2013-12-10 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
US6452024B1 (en) 2000-02-22 2002-09-17 Chaichem Pharmaceuticals International Process for extraction and purification of paclitaxel from natural sources
CZ2003837A3 (cs) 2000-09-22 2004-12-15 Bristol-Myers Squibb Company Způsob pro snížení toxicity při kombinovaných chemoterapiích
EP1337275A4 (de) 2000-11-02 2007-05-09 Sloan Kettering Inst Cancer Verfahren zur verbesserung der wirksamkeit von zytotoxischen mitteln durch verwendung von hsp90-hemmern
JP2006513152A (ja) * 2002-10-09 2006-04-20 ファイトジェン ライフ サイエンシズ インコーポレイテッド 新規タキサンならびにその使用および調製に関する方法
US6759539B1 (en) 2003-02-27 2004-07-06 Chaichem Pharmaceuticals International Process for isolation and purification of paclitaxel from natural sources
US8088737B2 (en) 2003-04-04 2012-01-03 Incyte Corporation Compositions, methods and kits relating to Her-2 cleavage
US7202370B2 (en) * 2003-10-27 2007-04-10 Conor Medsystems, Inc. Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III
EP1871753B1 (de) * 2005-03-31 2012-07-18 Accord Healthcare Inc. Herstellung von taxanen aus 9-dihydro-13-acetylbaccatin iii
EP1948669B1 (de) * 2005-11-04 2013-07-10 Accord Healthcare Inc. Neue verfahren zur herstellung von taxanen unter verwendung von chiralen hilfsstoffen
EP2132178B1 (de) 2006-12-20 2015-08-19 Merck Sharp & Dohme Corp. Jnk-hemmer
EP2483263B1 (de) 2009-09-30 2018-07-18 Merck Sharp & Dohme Corp. Heterocyclische verbindungen als erk-hemmer
JP6486002B2 (ja) 2010-08-23 2019-03-20 シントリックス・バイオシステムズ・インコーポレイテッドＳｙｎｔｒｉｘ Ｂｉｏｓｙｓｔｅｍｓ， Ｉｎｃ． Ｃｘｃｒ２モジュレーターとしてのアミノピリジンカルボキサミドおよびアミノピリミジンカルボキサミド
CN104744409A (zh) * 2011-06-07 2015-07-01 株式会社吴羽 氧杂环丁烷化合物的制造方法、唑甲基环戊醇化合物的制造方法、以及中间体化合物
US10561676B2 (en) 2013-08-02 2020-02-18 Syntrix Biosystems Inc. Method for treating cancer using dual antagonists of CXCR1 and CXCR2
US10046002B2 (en) 2013-08-02 2018-08-14 Syntrix Biosystems Inc. Method for treating cancer using chemokine antagonists
JP6509851B2 (ja) 2013-08-02 2019-05-08 シントリックス・バイオシステムズ・インコーポレイテッドＳｙｎｔｒｉｘ Ｂｉｏｓｙｓｔｅｍｓ， Ｉｎｃ． ２−［５−［ｎ−（４−フルオロフェニル）カルバモイル］ピリミジン−２−イルスルファニルメチル］−４−（トリフルオロメトキシ）フェニル」ボロン酸
US8969365B2 (en) 2013-08-02 2015-03-03 Syntrix Biosystems, Inc. Thiopyrimidinecarboxamides as CXCR1/2 modulators
CN110201717B (zh) * 2019-05-21 2021-11-23 南京工业大学 一种铜基金属有机多面体复合材料的制备方法与应用
CN114423459A (zh) 2019-09-19 2022-04-29 飞跃治疗公司 Dkk-1抑制剂用于治疗癌症的用途
IL293090A (en) 2019-11-22 2022-07-01 Leap Therapeutics Inc Methods for treating cancer using dkk-1 inhibitors

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2601676B1 (fr) * 1986-07-17 1988-09-23 Rhone Poulenc Sante Procede de preparation du taxol et du desacetyl-10 taxol
FR2601675B1 (fr) * 1986-07-17 1988-09-23 Rhone Poulenc Sante Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent
US4876399A (en) * 1987-11-02 1989-10-24 Research Corporation Technologies, Inc. Taxols, their preparation and intermediates thereof
FR2629818B1 (fr) * 1988-04-06 1990-11-16 Centre Nat Rech Scient Procede de preparation du taxol
USRE34277E (en) * 1988-04-06 1993-06-08 Centre National De La Recherche Scientifique Process for preparing taxol
FR2629819B1 (fr) * 1988-04-06 1990-11-16 Rhone Poulenc Sante Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii
US5175315A (en) * 1989-05-31 1992-12-29 Florida State University Method for preparation of taxol using β-lactam
US5015744A (en) * 1989-11-14 1991-05-14 Florida State University Method for preparation of taxol using an oxazinone
FR2662441B1 (fr) * 1990-05-22 1992-10-23 Rhone Poulenc Sante Procede de preparation enantioselective de derives de la phenylisoserine.
FR2662440B1 (fr) * 1990-05-22 1992-07-31 Rhone Poulenc Sante Procede de preparation stereoselective de derives de la phenylisoserine.
US5380916A (en) * 1990-11-02 1995-01-10 University Of Florida Method for the isolation and purification of taxane derivatives
WO1993002064A1 (fr) * 1991-07-16 1993-02-04 Centre National De La Recherche Scientifique (Cnrs) Nouveau derive de la 7-desacetoxy baccatine iv, sa preparation et son emploi
US5229526A (en) * 1991-09-23 1993-07-20 Florida State University Metal alkoxides
US5597931A (en) * 1992-03-30 1997-01-28 Sloan-Kettering Institute For Cancer Research Total synthesis of taxol and analogues thereof
US5488116A (en) * 1992-03-30 1996-01-30 Sloan-Kettering Institute For Cancer Research Total synthesis of taxol and analogues thereof
US5416225A (en) * 1992-03-30 1995-05-16 Sloan-Kettering Institute For Cancer Research Total synthesis of taxol
US5254703A (en) * 1992-04-06 1993-10-19 Florida State University Semi-synthesis of taxane derivatives using metal alkoxides and oxazinones
US5248796A (en) * 1992-06-18 1993-09-28 Bristol-Myers Squibb Company Taxol derivatives
US5461169A (en) * 1992-06-23 1995-10-24 The Scripps Research Institute Total synthesis of taxol and taxol analogs
US5274137A (en) * 1992-06-23 1993-12-28 Nicolaou K C Intermediates for preparation of taxols
US5481007A (en) * 1992-06-23 1996-01-02 The Scripps Research Institute Taxoid synthesis
PT668762E (pt) * 1992-11-13 2004-02-27 Univ Florida State Taxanos substituidos com isobutenilo e suas composicoes farmaceuticas
US5508447A (en) * 1994-05-24 1996-04-16 Board Of Regents, The University Of Texas System Short synthetic route to taxol and taxol derivatives

Also Published As

Publication number Publication date
SG44727A1 (en) 1997-12-19
EP0960881A1 (de) 1999-12-01
KR960703837A (ko) 1996-08-31
DE69424939T2 (de) 2000-11-02
AU7404294A (en) 1995-02-20
ES2149883T3 (es) 2000-11-16
DK0710223T3 (da) 2000-09-11
ES2198827T3 (es) 2004-02-01
EP0960881B1 (de) 2003-04-23
EP0710223A1 (de) 1996-05-08
PT710223E (pt) 2000-12-29
GR3034343T3 (en) 2000-12-29
DK0960881T3 (da) 2003-08-11
SG97813A1 (en) 2003-08-20
ATE193880T1 (de) 2000-06-15
JP2004115526A (ja) 2004-04-15
WO1995003265A1 (en) 1995-02-02
DE69432569D1 (de) 2003-05-28
US5760252A (en) 1998-06-02
US5405972A (en) 1995-04-11
DE69432569T2 (de) 2003-11-27
KR100325791B1 (ko) 2002-10-11
ATE238289T1 (de) 2003-05-15
CN1137789A (zh) 1996-12-11
EP0710223A4 (de) 1996-08-21
CN1046261C (zh) 1999-11-10
JP3564135B2 (ja) 2004-09-08
CA2167718A1 (en) 1995-02-02
KR100353666B1 (ko) 2002-09-23
AU687428B2 (en) 1998-02-26
KR100323273B1 (ko) 2002-03-15
JPH09501153A (ja) 1997-02-04
US5637732A (en) 1997-06-10
PT960881E (pt) 2003-09-30
US5618952A (en) 1997-04-08
CA2167718C (en) 2006-10-03
EP0710223B1 (de) 2000-06-14

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Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee