JP4281075B2 - カンプトテシン誘導体（ｃｐｔ−１１）および関連化合物を製造するための新規な中間体および方法 - Google Patents

カンプトテシン誘導体（ｃｐｔ−１１）および関連化合物を製造するための新規な中間体および方法 Download PDF

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JP4281075B2
JP4281075B2 JP53035696A JP53035696A JP4281075B2 JP 4281075 B2 JP4281075 B2 JP 4281075B2 JP 53035696 A JP53035696 A JP 53035696A JP 53035696 A JP53035696 A JP 53035696A JP 4281075 B2 JP4281075 B2 JP 4281075B2
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JPH11503156A (ja
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ヘネガー，ケビン・イー
シー，ジョン・シー
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ファルマシア・アンド・アップジョン・カンパニー・エルエルシー
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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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Paper (AREA)
  • Lubricants (AREA)
  • Steroid Compounds (AREA)
JP53035696A 1995-04-07 1996-04-01 カンプトテシン誘導体（ｃｐｔ−１１）および関連化合物を製造するための新規な中間体および方法 Expired - Fee Related JP4281075B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41964395A 1995-04-07 1995-04-07
US08/419,643 1995-04-07
PCT/US1996/004163 WO1996031513A1 (en) 1995-04-07 1996-04-01 Novel intermediates and process for the manufacture of camptothecin derivatives (cpt-11) and related compounds

Related Child Applications (1)

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JP2007277903A Division JP2008069170A (ja) 1995-04-07 2007-10-25 カンプトテシン誘導体（ｃｐｔ−１１）および関連化合物を製造するための新規な中間体および方法

Publications (3)

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JPH11503156A JPH11503156A (ja) 1999-03-23
JPH11503156A5 JPH11503156A5 (https=) 2004-07-22
JP4281075B2 true JP4281075B2 (ja) 2009-06-17

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JP53035696A Expired - Fee Related JP4281075B2 (ja) 1995-04-07 1996-04-01 カンプトテシン誘導体（ｃｐｔ−１１）および関連化合物を製造するための新規な中間体および方法
JP2007277903A Pending JP2008069170A (ja) 1995-04-07 2007-10-25 カンプトテシン誘導体（ｃｐｔ−１１）および関連化合物を製造するための新規な中間体および方法

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US (3) US6121451A (https=)
EP (1) EP0835257B1 (https=)
JP (2) JP4281075B2 (https=)
KR (1) KR100423627B1 (https=)
CN (5) CN1100058C (https=)
AT (1) ATE224899T1 (https=)
AU (1) AU717179B2 (https=)
CA (1) CA2214793C (https=)
CZ (1) CZ297862B6 (https=)
DE (1) DE69623960T2 (https=)
DK (1) DK0835257T3 (https=)
ES (1) ES2183943T3 (https=)
HK (2) HK1054234B (https=)
HU (1) HUP9801436A3 (https=)
IL (1) IL117684A (https=)
MX (1) MX9707706A (https=)
NO (2) NO320482B1 (https=)
NZ (1) NZ306664A (https=)
PL (2) PL186564B1 (https=)
PT (1) PT835257E (https=)
RU (1) RU2164917C2 (https=)
SI (1) SI0835257T1 (https=)
TW (1) TW438775B (https=)
WO (1) WO1996031513A1 (https=)
ZA (1) ZA962747B (https=)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG103322A1 (en) * 1996-10-30 2004-04-29 Tanabe Seiyaku Co S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof
KR20010052811A (ko) * 1998-10-07 2001-06-25 미우라 아끼라 1,2-이치환-2,3-에폭시프로판류의 광학이성체 혼합물과 그제조법 및 이것을 유효성분으로 하는 농약, 그리고 중간체
FR2794123B1 (fr) 1999-05-28 2001-07-27 Aventis Pharma Sa Preparation de derives de la camptothecine et de la nothapodytine
AU775373B2 (en) 1999-10-01 2004-07-29 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
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
WO2003089413A1 (en) * 2002-04-17 2003-10-30 Pharmacia Corporation Pharmacia corporation
US7151179B2 (en) 2003-05-12 2006-12-19 Scinopharm Taiwan, Ltd. Process for the preparation of 7-alkyl-10-hydroxy-20(S)-camptothecin
CZ299329B6 (cs) 2003-08-26 2008-06-18 Pliva-Lachema A.S. Zpusob výroby 7-ethyl-10-[ 4-(1-piperidino)-1-piperidino]karbonyloxykamptothecinu
CA2537336C (en) * 2003-09-17 2013-02-26 Nektar Therapeutics Al, Corporation Multi-arm polymer prodrugs
US8394365B2 (en) 2003-09-17 2013-03-12 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
WO2006082279A1 (en) * 2005-02-07 2006-08-10 Fermion Oy Process for the manufacturing of 7-ethyl-10-hydroxy camptothecin
PL1928883T3 (pl) * 2005-02-08 2014-03-31 Fermion Oy Sposób otrzymywania chlorowodorku irynotekanu
CA2591071C (en) * 2005-02-08 2014-04-29 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
CN101583380B (zh) * 2006-11-30 2013-07-10 尼克塔治疗公司 用于制备聚合物轭合物的方法
KR20090108082A (ko) * 2007-02-09 2009-10-14 엔존 파마슈티컬즈, 인코포레이티드 7-에틸-10-하이드록시캄토테신 다분지형 고분자 접합체를 이용한 내성 또는 불응성 암의 치료방법
KR101659099B1 (ko) * 2008-07-31 2016-09-22 더루우브리졸코오포레이션 신규 공중합체 및 이의 윤활 조성물
AU2009282413B2 (en) 2008-08-11 2014-07-17 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
TW201010732A (en) * 2008-08-29 2010-03-16 Enzon Pharmaceuticals Inc Method of treating RAS associated cancer
LT2349346T (lt) 2008-09-23 2019-09-25 Nektar Therapeutics Kamptotecino provaistų (pvz., peg-irinotekano) metronominio dozavimo būdas
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
WO2012088422A1 (en) 2010-12-22 2012-06-28 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)
EA035674B1 (ru) 2014-07-18 2020-07-24 Санофи Способ определения того, является ли пациент, предположительно страдающий от рака, кандидатом для терапии афлиберцептом
CN106937529B (zh) 2015-10-27 2021-02-05 加州太平洋医疗中心 鬼臼毒素衍生物及其应用
US10087194B2 (en) * 2015-10-27 2018-10-02 California Pacific Medical Center Podophyllotoxin derivatives and their use
ES3057783T3 (en) 2016-03-15 2026-03-04 Oryzon Genomics Sa Combinations of lsd1 inhibitors for use in the treatment of neoplastic diseases
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
EP3911660B1 (en) 2019-01-15 2023-05-10 Laurus Labs Limited Process for preparation of 2-amino-5-hydroxy propiophenone
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.
US5053512A (en) * 1987-04-14 1991-10-01 Research Triangle Institute Total synthesis of 20(S) and 20(R)-camptothecin and compthothecin derivatives
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
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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HK1054236B (zh) 2010-02-05
PL322651A1 (en) 1998-02-16
RU2164917C2 (ru) 2001-04-10
PL186564B1 (pl) 2004-01-30
PT835257E (pt) 2003-01-31
CN100537538C (zh) 2009-09-09
EP0835257B1 (en) 2002-09-25
IL117684A (en) 2002-02-10
NO329776B1 (no) 2010-12-13
NZ306664A (en) 1999-11-29
MX9707706A (es) 1997-12-31
WO1996031513A1 (en) 1996-10-10
DE69623960T2 (de) 2003-06-05
HK1055118A1 (zh) 2003-12-24
CN1434043B (zh) 2010-04-28
CN1181083A (zh) 1998-05-06
KR19980703691A (ko) 1998-12-05
CZ311097A3 (cs) 1998-03-18
ZA962747B (en) 1998-04-06
KR100423627B1 (ko) 2004-07-27
AU717179B2 (en) 2000-03-16
JPH11503156A (ja) 1999-03-23
HUP9801436A3 (en) 1998-11-30
TW438775B (en) 2001-06-07
CA2214793A1 (en) 1996-10-10
JP2008069170A (ja) 2008-03-27
SI0835257T1 (en) 2003-04-30
HK1009448A1 (en) 1999-09-10
HK1054234B (zh) 2010-12-24
ES2183943T3 (es) 2003-04-01
CN1434046A (zh) 2003-08-06
HK1054236A1 (zh) 2003-11-21
US6121451A (en) 2000-09-19
IL117684A0 (en) 1996-07-23
EP0835257A1 (en) 1998-04-15
CZ297862B6 (cs) 2007-04-18
HUP9801436A2 (hu) 1998-10-28
HK1055119A1 (en) 2003-12-24
CN1434044A (zh) 2003-08-06
NO320482B1 (no) 2005-12-12
DE69623960D1 (de) 2002-10-31
US6235907B1 (en) 2001-05-22
ATE224899T1 (de) 2002-10-15
US6444820B1 (en) 2002-09-03
NO20050408L (no) 1997-12-08
CN100396682C (zh) 2008-06-25
CN1100058C (zh) 2003-01-29
CN1434043A (zh) 2003-08-06
CN1434037A (zh) 2003-08-06
NO974608L (no) 1997-12-08
PL186446B1 (pl) 2004-01-30
HK1054234A1 (zh) 2003-11-21
CN1241926C (zh) 2006-02-15
NO974608D0 (no) 1997-10-06
CA2214793C (en) 2009-10-20
DK0835257T3 (da) 2003-02-03
AU5527896A (en) 1996-10-23

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