CA2353822C - Camptothecin analogs and methods of preparation thereof - Google Patents

Camptothecin analogs and methods of preparation thereof Download PDF

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Publication number
CA2353822C
CA2353822C CA2353822A CA2353822A CA2353822C CA 2353822 C CA2353822 C CA 2353822C CA 2353822 A CA2353822 A CA 2353822A CA 2353822 A CA2353822 A CA 2353822A CA 2353822 C CA2353822 C CA 2353822C
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CA
Canada
Prior art keywords
group
compound
alkyl
independently
hydroxy
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
CA2353822A
Other languages
English (en)
French (fr)
Other versions
CA2353822A1 (en
Inventor
Dennis P. Curran
Hubert Josien
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 Pittsburgh
Original Assignee
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 Pittsburgh filed Critical University of Pittsburgh
Publication of CA2353822A1 publication Critical patent/CA2353822A1/en
Application granted granted Critical
Publication of CA2353822C publication Critical patent/CA2353822C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
    • C07F7/083—Syntheses without formation of a Si-C bond

Landscapes

  • 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)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2353822A 1998-12-15 1999-12-15 Camptothecin analogs and methods of preparation thereof Expired - Fee Related CA2353822C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/212,178 US6136978A (en) 1993-06-30 1998-12-15 Camptothecin analogs and methods of preparation thereof
US09/212,178 1998-12-15
PCT/US1999/029937 WO2000035924A1 (en) 1998-12-15 1999-12-15 Camptothecin analogs and methods of preparation thereof

Publications (2)

Publication Number Publication Date
CA2353822A1 CA2353822A1 (en) 2000-06-22
CA2353822C true CA2353822C (en) 2011-05-31

Family

ID=22789889

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2353822A Expired - Fee Related CA2353822C (en) 1998-12-15 1999-12-15 Camptothecin analogs and methods of preparation thereof

Country Status (10)

Country Link
US (1) US6136978A (enExample)
EP (1) EP1140948A4 (enExample)
JP (1) JP4638987B2 (enExample)
KR (1) KR100750693B1 (enExample)
CN (1) CN1177850C (enExample)
AU (1) AU777786B2 (enExample)
CA (1) CA2353822C (enExample)
HK (1) HK1044156B (enExample)
NZ (1) NZ512210A (enExample)
WO (1) WO2000035924A1 (enExample)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6150343A (en) * 1993-06-30 2000-11-21 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US6207832B1 (en) 1999-04-09 2001-03-27 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US6497896B2 (en) 2001-02-12 2002-12-24 Supergen, Inc. Method for administering camptothecins via injection of a pharmaceutical composition comprising microdroplets containing a camptothecin
US6509027B2 (en) 2001-02-12 2003-01-21 Supergen, Inc. Injectable pharmaceutical composition comprising coated particles of camptothecin
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
KR20040048995A (ko) 2001-10-25 2004-06-10 다케다 야쿠힌 고교 가부시키가이샤 퀴놀린 화합물
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
CA2548543C (en) * 2003-12-17 2012-01-03 Bionumerik Pharmaceuticals, Inc. Process for making camptothecin derivatives
US7654501B2 (en) * 2007-06-06 2010-02-02 Matthews Stewart D Vehicle parking assistance device and method for use of same
US7687497B2 (en) * 2007-10-16 2010-03-30 Bionumerik Pharmaceuticals, Inc. C10-substituted camptothecin analogs
HUE031374T2 (en) 2007-10-16 2017-07-28 Bionumerik Pharmaceuticals Inc C10-substituted camptothecin analogs
JP5467046B2 (ja) * 2007-10-16 2014-04-09 バイオニューメリック・ファーマスーティカルズ・インコーポレイテッド Ｃ７−置換カンプトテシン類似体
US8569265B2 (en) * 2011-05-06 2013-10-29 Bionumerik Pharmaceuticals, Inc. Deuterated analogs of (4S)-4-ethyl-4-hydroxy-11-[2- (trimethylsilyl)ethyl]-1H-pyrano[3′, 4′:6,7] indolizino [1,2-b]quinoline-3,14(4H, 12H)-dione and methods of use thereof
US8722886B1 (en) * 2012-11-13 2014-05-13 Bionumerik Pharmaceuticals, Inc. Methods for the total chemical synthesis of enantiomerically-pure 7-(2′-trimethylsilyl)ethyl camptothecin
EP3209666B1 (en) * 2014-10-22 2019-08-21 Vivacitas Oncology Inc. Methods and systems for camptothecin analog synthesis
CN107964257B (zh) * 2016-10-20 2021-07-09 香港理工大学深圳研究院 喹啉鎓离子骨架结构有机染料化合物及其制备方法和应用
CA3241157A1 (en) * 2021-12-16 2023-06-22 Wei Zhou Camptothecin compound and conjugate thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5405963A (en) * 1993-06-10 1995-04-11 Smithkline Beecham Corporation Process for asymmetric total synthesis of camptothecin analogues
US6150343A (en) * 1993-06-30 2000-11-21 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US5744605A (en) * 1993-06-30 1998-04-28 University Of Pittsburgh Intermediates in the synthesis of (+) camptothecin and related compounds and synthesis thereof
JPH09123996A (ja) * 1995-10-30 1997-05-13 Sanshin Ind Co Ltd 船外機のシフト駆動機構
DE69728152T2 (de) * 1996-08-19 2004-08-05 Bionumerik Pharmaceuticals, Inc., San Antonio Hoch-lipophile campothecin-derivate
DK1017675T3 (da) * 1997-02-14 2006-10-16 Bionumerik Pharmaceuticals Inc Stærkt lipofile camptothecinderivater

Also Published As

Publication number Publication date
KR100750693B1 (ko) 2007-08-22
CN1352646A (zh) 2002-06-05
JP2002532505A (ja) 2002-10-02
EP1140948A4 (en) 2008-01-02
CN1177850C (zh) 2004-12-01
HK1044156B (zh) 2005-04-08
WO2000035924A1 (en) 2000-06-22
JP4638987B2 (ja) 2011-02-23
NZ512210A (en) 2004-12-24
US6136978A (en) 2000-10-24
EP1140948A1 (en) 2001-10-10
CA2353822A1 (en) 2000-06-22
AU777786B2 (en) 2004-10-28
KR20010101250A (ko) 2001-11-14
AU3123600A (en) 2000-07-03
HK1044156A1 (en) 2002-10-11

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