CA2214793C - Novel intermediates and process for the manufacture of camptothecin derivatives (cpt-11) and related compounds - Google Patents

Novel intermediates and process for the manufacture of camptothecin derivatives (cpt-11) and related compounds Download PDF

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Publication number
CA2214793C
CA2214793C CA002214793A CA2214793A CA2214793C CA 2214793 C CA2214793 C CA 2214793C CA 002214793 A CA002214793 A CA 002214793A CA 2214793 A CA2214793 A CA 2214793A CA 2214793 C CA2214793 C CA 2214793C
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Prior art keywords
alkyl
substituted
amino
group
alkyl substituted
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Expired - Fee Related
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CA002214793A
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English (en)
French (fr)
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CA2214793A1 (en
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Kevin E. Henegar
John C. Sih
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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)
  • 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)
CA002214793A 1995-04-07 1996-04-01 Novel intermediates and process for the manufacture of camptothecin derivatives (cpt-11) and related compounds Expired - Fee Related CA2214793C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41964395A 1995-04-07 1995-04-07
US419,643 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

Publications (2)

Publication Number Publication Date
CA2214793A1 CA2214793A1 (en) 1996-10-10
CA2214793C true CA2214793C (en) 2009-10-20

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ID=23663114

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CA002214793A Expired - Fee Related CA2214793C (en) 1995-04-07 1996-04-01 Novel intermediates and process for the manufacture of camptothecin derivatives (cpt-11) and related compounds

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US (3) US6121451A (enExample)
EP (1) EP0835257B1 (enExample)
JP (2) JP4281075B2 (enExample)
KR (1) KR100423627B1 (enExample)
CN (5) CN100396682C (enExample)
AT (1) ATE224899T1 (enExample)
AU (1) AU717179B2 (enExample)
CA (1) CA2214793C (enExample)
CZ (1) CZ297862B6 (enExample)
DE (1) DE69623960T2 (enExample)
DK (1) DK0835257T3 (enExample)
ES (1) ES2183943T3 (enExample)
HK (2) HK1054234B (enExample)
HU (1) HUP9801436A3 (enExample)
IL (1) IL117684A (enExample)
MX (1) MX9707706A (enExample)
NO (2) NO320482B1 (enExample)
NZ (1) NZ306664A (enExample)
PL (2) PL186564B1 (enExample)
PT (1) PT835257E (enExample)
RU (1) RU2164917C2 (enExample)
SI (1) SI0835257T1 (enExample)
TW (1) TW438775B (enExample)
WO (1) WO1996031513A1 (enExample)
ZA (1) ZA962747B (enExample)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG104284A1 (en) * 1996-10-30 2004-06-21 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
EP1229934B1 (en) 1999-10-01 2014-03-05 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
TWI245768B (en) * 2001-02-21 2005-12-21 Yakult Honsha Kk Process for synthesizing camptothecin related compound(s)
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
JP3839813B2 (ja) * 2002-04-17 2006-11-01 ファルマシア コーポレイション カンプトテシン誘導体の調製に有用な化合物
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
US8394365B2 (en) 2003-09-17 2013-03-12 Nektar Therapeutics Multi-arm polymer prodrugs
CN1852740B (zh) * 2003-09-17 2011-05-11 耐科塔医药公司 多支链聚合物的药物前体
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
US20080182990A1 (en) * 2004-08-09 2008-07-31 Shilpa Medicare Limited Process for the Preparation of Irinotecan Hydrochloride Trihydrate
US20060046993A1 (en) * 2004-09-01 2006-03-02 Pharmacia Italia S.P.A. Crystalline polymorphic form of irinotecan hydrochloride
ES2333462T3 (es) * 2005-02-07 2010-02-22 Fermion Oy Procedimiento para la preparacion de 7-etil-10-hidroxi camptotecina.
JP5133703B2 (ja) * 2005-02-08 2013-01-30 フェルミオン オサケ ユキチュア ［１，４’］ビピペリジニル−１’−カルボニルクロリドまたはその塩酸塩の製造方法
US7767813B2 (en) * 2005-02-08 2010-08-03 Fermion Oy Preparation method
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
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
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
KR101441709B1 (ko) 2006-11-30 2014-09-18 넥타르 테라퓨틱스 중합체 컨쥬게이트의 제조 방법
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
CN104277144A (zh) * 2008-07-31 2015-01-14 卢布里佐尔公司 共聚物及其润滑组合物
EP2331140B1 (en) * 2008-08-11 2018-07-04 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
WO2010025337A1 (en) * 2008-08-29 2010-03-04 Enzon Pharmaceuticals, Inc. Method of treating ras associated cancer
RS59607B1 (sr) 2008-09-23 2020-01-31 Nektar Therapeutics Metod metronomskog doziranja kamptotecinskih prolekova (npr. peg-irinotekan)
JP2012506380A (ja) * 2008-10-21 2012-03-15 エンゾン ファーマシューティカルズ，インコーポレーテッド ７−エチル−１０−ヒドロキシカンプトテシンのマルチアーム型ポリマーコンジュゲートによる神経芽腫の治療
WO2012032531A1 (en) * 2010-09-06 2012-03-15 Avra Laboratories Pvt. Ltd. Process for the manufacture of irinotecan hydrochloride by total synthesis
US10894087B2 (en) 2010-12-22 2021-01-19 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)
SI3170005T1 (sl) 2014-07-18 2019-08-30 Sanofi Postopek napovedovanja izida zdravljenja z afliberceptom, pacienta, pri katerem obstaja sum, da je zbolel za rakom
ES2806624T3 (es) 2015-10-27 2021-02-18 California Pacific Medical Center Derivados de podofilotoxina y su uso
US10087194B2 (en) * 2015-10-27 2018-10-02 California Pacific Medical Center Podophyllotoxin derivatives and their use
SG11201807965YA (en) 2016-03-15 2018-10-30 Oryzon Genomics Sa Combinations of lsd1 inhibitors for use in the treatment of solid tumors
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
US11434196B2 (en) 2019-01-15 2022-09-06 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
EP0220601B1 (en) * 1985-10-21 1991-12-11 Daiichi Seiyaku Co., Ltd. Pyranoindolizine derivatives and preparation process thereof
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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CN100396682C (zh) 2008-06-25
US6444820B1 (en) 2002-09-03
CZ311097A3 (cs) 1998-03-18
US6235907B1 (en) 2001-05-22
IL117684A0 (en) 1996-07-23
KR100423627B1 (ko) 2004-07-27
CN1434043B (zh) 2010-04-28
HK1055118A1 (zh) 2003-12-24
HK1055119A1 (en) 2003-12-24
ES2183943T3 (es) 2003-04-01
CN1181083A (zh) 1998-05-06
HK1054236B (zh) 2010-02-05
JPH11503156A (ja) 1999-03-23
MX9707706A (es) 1997-12-31
HK1054234B (zh) 2010-12-24
PT835257E (pt) 2003-01-31
CN1434046A (zh) 2003-08-06
NO329776B1 (no) 2010-12-13
NZ306664A (en) 1999-11-29
EP0835257A1 (en) 1998-04-15
HK1054236A1 (zh) 2003-11-21
DE69623960T2 (de) 2003-06-05
AU5527896A (en) 1996-10-23
PL186446B1 (pl) 2004-01-30
DK0835257T3 (da) 2003-02-03
PL322651A1 (en) 1998-02-16
SI0835257T1 (en) 2003-04-30
NO320482B1 (no) 2005-12-12
CN1100058C (zh) 2003-01-29
JP4281075B2 (ja) 2009-06-17
CZ297862B6 (cs) 2007-04-18
HUP9801436A2 (hu) 1998-10-28
PL186564B1 (pl) 2004-01-30
HUP9801436A3 (en) 1998-11-30
US6121451A (en) 2000-09-19
CN1434037A (zh) 2003-08-06
HK1009448A1 (en) 1999-09-10
CA2214793A1 (en) 1996-10-10
CN100537538C (zh) 2009-09-09
ATE224899T1 (de) 2002-10-15
AU717179B2 (en) 2000-03-16
EP0835257B1 (en) 2002-09-25
DE69623960D1 (de) 2002-10-31
NO974608L (no) 1997-12-08
KR19980703691A (ko) 1998-12-05
HK1054234A1 (zh) 2003-11-21
RU2164917C2 (ru) 2001-04-10
NO20050408L (no) 1997-12-08
WO1996031513A1 (en) 1996-10-10
CN1434044A (zh) 2003-08-06
CN1241926C (zh) 2006-02-15
TW438775B (en) 2001-06-07
ZA962747B (en) 1998-04-06
IL117684A (en) 2002-02-10
CN1434043A (zh) 2003-08-06
NO974608D0 (no) 1997-10-06
JP2008069170A (ja) 2008-03-27

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