CN1241926C - 用于制备喜树碱衍生物（cpt－11）以及相关化合物的新的中间体和方法 - Google Patents

用于制备喜树碱衍生物（cpt－11）以及相关化合物的新的中间体和方法 Download PDF

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CN1241926C
CN1241926C CNB031030998A CN03103099A CN1241926C CN 1241926 C CN1241926 C CN 1241926C CN B031030998 A CNB031030998 A CN B031030998A CN 03103099 A CN03103099 A CN 03103099A CN 1241926 C CN1241926 C CN 1241926C
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alkyl
substituted
aryl
item
benzyl
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CN1434046A (zh
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K·E·汉尼格
J·C·赛
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Pharmacia and Upjohn Co
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Pharmacia and Upjohn Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Paper (AREA)
  • Lubricants (AREA)
  • Steroid Compounds (AREA)
CNB031030998A 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt－11）以及相关化合物的新的中间体和方法 Expired - Fee Related CN1241926C (zh)

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US41964395A 1995-04-07 1995-04-07
US08/419,643 1995-04-07

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CN96193138A Division CN1100058C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物(cpt－11)以及相关化合物的中间体及方法

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CN1434046A CN1434046A (zh) 2003-08-06
CN1241926C true CN1241926C (zh) 2006-02-15

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CN96193138A Expired - Fee Related CN1100058C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物(cpt－11)以及相关化合物的中间体及方法
CNB031030998A Expired - Fee Related CN1241926C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt－11）以及相关化合物的新的中间体和方法
CN03103098XA Expired - Fee Related CN1434043B (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt-11）以及相关化合物的中间体和方法
CNB031031005A Expired - Fee Related CN100537538C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt-11）以及相关化合物的中间体和方法
CNB031030971A Expired - Fee Related CN100396682C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt-11）以及相关化合物的中间体和方法

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CN96193138A Expired - Fee Related CN1100058C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物(cpt－11)以及相关化合物的中间体及方法

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CN03103098XA Expired - Fee Related CN1434043B (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt-11）以及相关化合物的中间体和方法
CNB031031005A Expired - Fee Related CN100537538C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt-11）以及相关化合物的中间体和方法
CNB031030971A Expired - Fee Related CN100396682C (zh) 1995-04-07 1996-04-01 用于制备喜树碱衍生物（cpt-11）以及相关化合物的中间体和方法

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Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG116433A1 (en) 1996-10-30 2005-11-28 Tanabe Seiyaku Co S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof.
WO2000020405A1 (en) * 1998-10-07 2000-04-13 Mitsubishi Chemical Corporation Mixtures of optical isomers of 1,2-disubstituted-2,3-epoxypropanes, process for producing the same, pesticides containing the same as the active ingredient and intermediates thereof
FR2794123B1 (fr) 1999-05-28 2001-07-27 Aventis Pharma Sa Preparation de derives de la camptothecine et de la nothapodytine
EP2289549A3 (en) 1999-10-01 2011-06-15 Immunogen, Inc. Immunoconjugates for treating cancer
US6855294B2 (en) * 2000-11-22 2005-02-15 Resonance, Inc. Apparatus and methods for efficient generation of chlorine dioxide
AR035684A1 (es) * 2001-02-21 2004-06-23 Yakult Honsha Kk Procedimiento para preparar 2'-amino-5'-hidroxipropiofenona, uso de la misma para la preparacion de analogos de camptotecina, procedimiento para prepararlos, compuestos intermediarios, procedimiento para preparar una cetona triciclica utilizada en la sintesis de analogos de camptotecina
US6723853B2 (en) 2001-08-27 2004-04-20 University Of Pittsburgh Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
BR0309284A (pt) * 2002-04-17 2005-02-22 Pharmacia Corp Compostos úteis na preparação de derivados de camptotecina
CN100344633C (zh) 2003-05-12 2007-10-24 台湾神隆股份有限公司 用于制备7－烷基－10－羟基－20(s)－喜树碱的方法
CZ299329B6 (cs) 2003-08-26 2008-06-18 Pliva-Lachema A.S. Zpusob výroby 7-ethyl-10-[ 4-(1-piperidino)-1-piperidino]karbonyloxykamptothecinu
US8394365B2 (en) * 2003-09-17 2013-03-12 Nektar Therapeutics Multi-arm polymer prodrugs
US7744861B2 (en) * 2003-09-17 2010-06-29 Nektar Therapeutics Multi-arm polymer prodrugs
CZ299593B6 (cs) 2003-12-16 2008-09-10 Pliva-Lachema A. S. Zpusob výroby 7-ethyl-10-hydroxykamptothecinu
US20050197355A1 (en) * 2004-03-02 2005-09-08 Henegar Kevin E. Compounds useful in preparing camptothecin derivatives
US20050267141A1 (en) * 2004-05-28 2005-12-01 Phytogen Life Sciences Inc. Process to prepare camptothecin derivatives
US20050272757A1 (en) * 2004-06-04 2005-12-08 Phytogen Life Sciences Inc. Process to prepare camptothecin derivatives and novel intermediate and compounds thereof
JP2008509211A (ja) * 2004-08-09 2008-03-27 シルパ・メディケア・リミテッド 塩酸イリノテカン三水和物の改良された製造方法
US20060046993A1 (en) * 2004-09-01 2006-03-02 Pharmacia Italia S.P.A. Crystalline polymorphic form of irinotecan hydrochloride
ATE446299T1 (de) * 2005-02-07 2009-11-15 Fermion Oy Verfahren zur herstellung von 7-ethyl-10- hydroxycamptothecin
WO2006084941A2 (en) 2005-02-08 2006-08-17 Fermion Oy Process for the preparation of irinotecan hydrochloride
EP1846371B1 (en) * 2005-02-08 2013-07-31 Fermion Oy Process for producing [1,4']bipiperidinyl-1'-carbonyl chloride or hydrochloride thereof
TWI375678B (en) 2005-06-09 2012-11-01 Yakult Honsha Kk A method of preparation of a tricyclic ketone
EP1803725A1 (en) * 2005-12-13 2007-07-04 W.C. Heraeus GmbH Methods for preparing irinotecan
US7671067B2 (en) * 2006-02-09 2010-03-02 Enzon Pharmaceuticals, Inc. Treatment of non-hodgkin's lymphomas with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamtothecin
US7462627B2 (en) * 2006-02-09 2008-12-09 Enzon Pharmaceuticals, Inc. Multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin for treatment of breast, colorectal, pancreatic, ovarian and lung cancers
AU2007325631B9 (en) 2006-11-30 2014-01-30 Nektar Therapeutics Method for preparing a polymer conjugate
EP2109448B1 (en) * 2007-02-09 2013-09-11 Enzon Pharmaceuticals, Inc. Treatment of resistant or refractory cancers with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin
BRPI0916605A2 (pt) * 2008-07-31 2017-07-04 Lubrizol Corp novos copolimeros e composições lubrificantes destes
US8637466B2 (en) 2008-08-11 2014-01-28 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
TW201010732A (en) * 2008-08-29 2010-03-16 Enzon Pharmaceuticals Inc Method of treating RAS associated cancer
EP2349346B1 (en) 2008-09-23 2019-08-28 Nektar Therapeutics Method of metronomic dosing with camptothecin prodrugs (e.g. peg-irinotecan)
KR20110075029A (ko) * 2008-10-21 2011-07-05 엔즌 파마슈티칼스, 인코포레이티드 7-에틸-10-하이드록시캄토테신의 다중-암 고분자 컨쥬게이트로 신경모세포종의 치료
WO2012032531A1 (en) * 2010-09-06 2012-03-15 Avra Laboratories Pvt. Ltd. Process for the manufacture of irinotecan hydrochloride by total synthesis
WO2012088445A1 (en) 2010-12-22 2012-06-28 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
US20130331443A1 (en) 2010-12-22 2013-12-12 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds
JO3283B1 (ar) 2011-04-26 2018-09-16 Sanofi Sa تركيب يتضمن أفليبيرسيبت, حمض فولينيك, 5- فلورويوراسيل (5- Fu) وإرينوسيتان (FOLFIRI)
DK3170005T3 (da) 2014-07-18 2019-07-08 Sanofi Sa Fremgangsmåde til forudsigelse af resultatet af en behandling med aflibercept hos en patient, der mistænkes for at lide af cancer
US10087194B2 (en) * 2015-10-27 2018-10-02 California Pacific Medical Center Podophyllotoxin derivatives and their use
CN112759603B (zh) 2015-10-27 2022-09-09 加州太平洋医疗中心 鬼臼毒素衍生物及其应用
JP7158023B2 (ja) 2016-03-15 2022-10-21 オリソン ヘノミクス エセ． アー． 固形腫瘍の治療における使用のための、ｌｓｄ１阻害剤の組合せ
CN105965710B (zh) * 2016-06-28 2019-03-22 常州大学 一种硅棒金钢线切割树脂板的制备方法及应用
ES2951064T3 (es) 2019-01-15 2023-10-17 Laurus Labs Ltd Procedimiento de preparación de 2-amino-5-hidroxipropiofenona
CN112300184B (zh) * 2019-08-02 2022-12-06 华东师范大学 一种三元环化合物的制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5217499A (en) * 1975-07-31 1977-02-09 Nippon Chemiphar Co Ltd Preparation of mappicine
DE3682874D1 (de) * 1985-10-21 1992-01-23 Daiichi Seiyaku Co Pyranoindolizinderivate und verfahren zu ihrer herstellung.
US4981968A (en) * 1987-03-31 1991-01-01 Research Triangle Institute Synthesis of camptothecin and analogs thereof
US4894456A (en) * 1987-03-31 1990-01-16 Research Triangle Institute Synthesis of camptothecin and analogs thereof
US5053512A (en) * 1987-04-14 1991-10-01 Research Triangle Institute Total synthesis of 20(S) and 20(R)-camptothecin and compthothecin derivatives
US5883255A (en) * 1990-10-31 1999-03-16 Smithkline Beecham Corporation Substituted indolizino 1,2-b!quinolinones
US5405963A (en) * 1993-06-10 1995-04-11 Smithkline Beecham Corporation Process for asymmetric total synthesis of camptothecin analogues
GB9316352D0 (en) * 1993-08-06 1993-09-22 Erba Carlo Spa Process for the preparation of 9-amino camptothecin
GB9319944D0 (en) * 1993-09-28 1993-11-17 Erba Carlo Spa Process for the preparation of 9-amino camptothecin

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US6121451A (en) 2000-09-19
CN1434043A (zh) 2003-08-06
HK1054236A1 (zh) 2003-11-21
PL186446B1 (pl) 2004-01-30
IL117684A (en) 2002-02-10
NO20050408L (no) 1997-12-08
CA2214793A1 (en) 1996-10-10
JP2008069170A (ja) 2008-03-27
RU2164917C2 (ru) 2001-04-10
CN1100058C (zh) 2003-01-29
PL322651A1 (en) 1998-02-16
HK1009448A1 (en) 1999-09-10
ATE224899T1 (de) 2002-10-15
NO974608D0 (no) 1997-10-06
KR100423627B1 (ko) 2004-07-27
CN1434046A (zh) 2003-08-06
DE69623960T2 (de) 2003-06-05
IL117684A0 (en) 1996-07-23
US6235907B1 (en) 2001-05-22
CN100396682C (zh) 2008-06-25
NO329776B1 (no) 2010-12-13
CN1434044A (zh) 2003-08-06
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