CA2369270C - Camptothecin analogs and methods of preparation thereof - Google Patents

Camptothecin analogs and methods of preparation thereof Download PDF

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Publication number
CA2369270C
CA2369270C CA2369270A CA2369270A CA2369270C CA 2369270 C CA2369270 C CA 2369270C CA 2369270 A CA2369270 A CA 2369270A CA 2369270 A CA2369270 A CA 2369270A CA 2369270 C CA2369270 C CA 2369270C
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CA
Canada
Prior art keywords
group
compound
alkyl
hydroxy
alkynyl
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
CA2369270A
Other languages
English (en)
French (fr)
Other versions
CA2369270A1 (en
Inventor
Dennis P. Curran
David Bom
Thomas G. Burke
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.)
University of Kentucky Research Foundation
University of Pittsburgh
Original Assignee
University of Kentucky Research Foundation
University of Pittsburgh
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 University of Kentucky Research Foundation, University of Pittsburgh filed Critical University of Kentucky Research Foundation
Publication of CA2369270A1 publication Critical patent/CA2369270A1/en
Application granted granted Critical
Publication of CA2369270C publication Critical patent/CA2369270C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines Containing Plant Substances (AREA)
CA2369270A 1999-04-09 2000-04-07 Camptothecin analogs and methods of preparation thereof Expired - Fee Related CA2369270C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/290,019 US6207832B1 (en) 1999-04-09 1999-04-09 Camptothecin analogs and methods of preparation thereof
US09/290,019 1999-04-09
PCT/US2000/009401 WO2000061146A1 (en) 1999-04-09 2000-04-07 Camptothecin analogs and methods of preparation thereof

Publications (2)

Publication Number Publication Date
CA2369270A1 CA2369270A1 (en) 2000-10-19
CA2369270C true CA2369270C (en) 2011-08-16

Family

ID=23114196

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2369270A Expired - Fee Related CA2369270C (en) 1999-04-09 2000-04-07 Camptothecin analogs and methods of preparation thereof

Country Status (13)

Country Link
US (7) US6207832B1 (enExample)
EP (1) EP1173180B1 (enExample)
JP (1) JP4866505B2 (enExample)
KR (1) KR100717900B1 (enExample)
CN (2) CN101058579A (enExample)
AT (1) ATE399171T1 (enExample)
AU (1) AU781302B2 (enExample)
CA (1) CA2369270C (enExample)
DE (1) DE60039291D1 (enExample)
ES (1) ES2308977T3 (enExample)
HK (1) HK1046374B (enExample)
NZ (1) NZ514635A (enExample)
WO (1) WO2000061146A1 (enExample)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2790261B1 (fr) * 1999-02-26 2004-09-10 Sod Conseils Rech Applic Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation
US6207832B1 (en) 1999-04-09 2001-03-27 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US6629995B1 (en) * 2000-03-31 2003-10-07 Super Gen, Inc. Camptothecin conjugates
US6350756B1 (en) 2001-01-18 2002-02-26 California Pacific Medical Center Camptothecin derivatives
US6855720B2 (en) * 2001-03-01 2005-02-15 California Pacific Medical Center Nitrogen-based camptothecin derivatives
US6403604B1 (en) * 2001-03-01 2002-06-11 California Pacific Medical Center Nitrogen-based camptothecin derivatives
US6372906B1 (en) 2001-04-12 2002-04-16 University Of Pittsburgh Synthesis of silyl camptothecins and silyl homocamptothecins
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
AU2003207369A1 (en) * 2002-02-18 2003-09-04 Dr. Reddy's Laboratories Limited A process for the preparation of 10-hydroxy-9-n,n-dimethylaminomethyl-5-(2'-fluoroethoxy)-20(s)-camptothecin hydrochloride
WO2003099825A1 (en) * 2002-05-22 2003-12-04 University Of Pittsburgh Synthesis of polycyclic quinolines
AU2003243380A1 (en) * 2002-06-03 2003-12-19 California Pacific Medical Center Nitrogen-based homo-camptothecin derivatives
WO2003101406A1 (en) * 2002-06-03 2003-12-11 California Pacific Medical Center Homo-camptothecin derivatives
AU2003280592B2 (en) * 2002-10-31 2008-12-18 Nippon Kayaku Kabushiki Kaisha High-molecular weight derivatives of camptothecins
US7064206B1 (en) 2003-05-12 2006-06-20 University Of Kentucky Research Foundation Highly lipophilic camptothecin intermediates and prodrugs and methods of preparation thereof
US7064202B1 (en) 2003-05-12 2006-06-20 University Of Kentucky Research Foundation Camptothecin intermediates and prodrugs and methods of preparation thereof
ITRM20040241A1 (it) * 2004-05-13 2004-08-13 Ist Naz Stud Cura Dei Tumori Camptotecine coniugate in posizione 20 con antagonisti delle integrine.
JP4820758B2 (ja) * 2004-09-22 2011-11-24 日本化薬株式会社 新規ブロック共重合体、ミセル調製物及びそれを有効成分とする抗癌剤
KR101378484B1 (ko) * 2005-03-02 2014-03-27 뉴 센츄리 파마슈티컬스, 인코포레이티드 알부민 결합성 약물의 안전성 및 효능을 증가시키는 방법및 조성물
US7875602B2 (en) * 2005-10-21 2011-01-25 Sutter West Bay Hospitals Camptothecin derivatives as chemoradiosensitizing agents
KR20080106254A (ko) 2006-03-28 2008-12-04 니폰 가야꾸 가부시끼가이샤 탁산류의 고분자 결합체
RU2447095C2 (ru) 2006-05-18 2012-04-10 Ниппон Каяку Кабусики Кайся Высокомолекулярный конъюгат подофиллотоксинов
US20090239782A1 (en) * 2006-10-03 2009-09-24 Masaharu Nakamura High-molecular weight conjugate of resorcinol derivatives
US8334364B2 (en) 2006-11-06 2012-12-18 Nipon Kayaku Kabushiki Kaisha High-molecular weight derivative of nucleic acid antimetabolite
US8188222B2 (en) 2006-11-08 2012-05-29 Nippon Kayaku Kabushiki Kaisha High molecular weight derivative of nucleic acid antimetabolite
WO2009041570A1 (ja) 2007-09-28 2009-04-02 Nippon Kayaku Kabushiki Kaisha ステロイド類の高分子結合体
CN101977631A (zh) * 2008-03-18 2011-02-16 日本化药株式会社 生理活性物质的高分子量偶联物
JP5366940B2 (ja) 2008-05-08 2013-12-11 日本化薬株式会社 葉酸若しくは葉酸誘導体の高分子結合体
WO2010131675A1 (ja) 2009-05-15 2010-11-18 日本化薬株式会社 水酸基を有する生理活性物質の高分子結合体
US9018323B2 (en) 2010-11-17 2015-04-28 Nippon Kayaku Kabushiki Kaisha Polymer derivative of cytidine metabolic antagonist
RU2623426C2 (ru) 2011-09-11 2017-06-26 Ниппон Каяку Кабусики Кайся Способ получения блок-сополимера

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5428166A (en) * 1992-06-18 1995-06-27 North Carolina State University Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs
US5405963A (en) 1993-06-10 1995-04-11 Smithkline Beecham Corporation Process for asymmetric total synthesis of camptothecin analogues
US5744605A (en) * 1993-06-30 1998-04-28 University Of Pittsburgh Intermediates in the synthesis of (+) camptothecin and related compounds and synthesis thereof
US6211371B1 (en) * 1993-06-30 2001-04-03 University Of Pittsburgh Intermediates in the synthesis of camptothecin and related compounds and synthesis thereof
US6150343A (en) 1993-06-30 2000-11-21 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US6136978A (en) 1993-06-30 2000-10-24 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US5491237A (en) * 1994-05-03 1996-02-13 Glaxo Wellcome Inc. Intermediates in pharmaceutical camptothecin preparation
US5935967A (en) 1995-06-05 1999-08-10 Bionumerik Pharmaceuticals, Inc. Pharmaceutical formulations of highly lipophilic camptothecin derivatives
FR2768431B1 (fr) 1997-08-29 2000-03-24 Sod Conseils Rech Applic Nouveaux analogues optiquement purs de la camptothecine, nouvel intermediaire de synthese optiquement pur et son procede de preparation
GB9512670D0 (en) * 1995-06-21 1995-08-23 Sod Conseils Rech Applic Camptothecin analogues
JP3576171B2 (ja) 1995-06-21 2004-10-13 ソシエテ・ド・コンセイユ・ド・ルシエルシエ・エ・ダアツプリカーション・シヤンテイフイツク・（エス．セー．エール．アー．エス） カンプトテシンの新規な同族体、その製造方法、その医薬としての用途及びこれを含有する医薬組成物
FR2757514B1 (fr) 1996-12-20 1999-02-12 Sod Conseils Rech Applic Nouveaux analogues de la camptothecine, des procedes de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant
FR2790261B1 (fr) * 1999-02-26 2004-09-10 Sod Conseils Rech Applic Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation
ES2214634T3 (es) 1996-08-19 2004-09-16 Bionumerik Pharmaceuticals, Inc. Derivados muy lipofilos de la camptotecina.
UA57757C2 (uk) * 1996-12-20 2003-07-15 Сос'Єте Де Консей Де Решерш Е Даплікасьон С'Єнтіфік (С.К.Р.А.С.) Аналоги камптотецину, спосіб їх отримання (варіанти) і фармацевтична композиція
CA2280905C (en) 1997-02-14 2006-08-29 Bionumerik Pharmaceuticals, Inc. Highly lipophilic camptothecin derivatives
WO1999006310A2 (en) * 1997-08-04 1999-02-11 Abb Power T & D Company Inc. Method and apparatus for manufacturing a variable insulated helically wound electrical coil
US6057303A (en) 1998-10-20 2000-05-02 Bionumerik Pharmaceuticals, Inc. Highly lipophilic Camptothecin derivatives
US6207832B1 (en) * 1999-04-09 2001-03-27 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US6250342B1 (en) * 1999-09-02 2001-06-26 David Lonardelli Cv joint boot clamp tightening tool

Also Published As

Publication number Publication date
EP1173180B1 (en) 2008-06-25
HK1046374A1 (en) 2003-01-10
US6410731B2 (en) 2002-06-25
NZ514635A (en) 2004-02-27
US20120136153A1 (en) 2012-05-31
WO2000061146A1 (en) 2000-10-19
KR20010113784A (ko) 2001-12-28
US20050014775A1 (en) 2005-01-20
JP2002541201A (ja) 2002-12-03
CN101058579A (zh) 2007-10-24
ATE399171T1 (de) 2008-07-15
US20010003779A1 (en) 2001-06-14
WO2000061146A9 (en) 2002-01-03
US20030088101A1 (en) 2003-05-08
EP1173180A4 (en) 2004-12-01
CA2369270A1 (en) 2000-10-19
AU4217700A (en) 2000-11-14
US20090198061A1 (en) 2009-08-06
HK1046374B (zh) 2007-08-24
ES2308977T3 (es) 2008-12-16
CN1367694A (zh) 2002-09-04
US7220860B2 (en) 2007-05-22
AU781302B2 (en) 2005-05-12
US6207832B1 (en) 2001-03-27
US7982041B2 (en) 2011-07-19
JP4866505B2 (ja) 2012-02-01
US20080027224A1 (en) 2008-01-31
US6809103B2 (en) 2004-10-26
KR100717900B1 (ko) 2007-05-14
US7538220B2 (en) 2009-05-26
DE60039291D1 (de) 2008-08-07
EP1173180A1 (en) 2002-01-23
CN1319975C (zh) 2007-06-06

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