CA2302226C - Camptothecin analogs and methods of preparation thereof - Google Patents

Camptothecin analogs and methods of preparation thereof Download PDF

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Publication number
CA2302226C
CA2302226C CA2302226A CA2302226A CA2302226C CA 2302226 C CA2302226 C CA 2302226C CA 2302226 A CA2302226 A CA 2302226A CA 2302226 A CA2302226 A CA 2302226A CA 2302226 C CA2302226 C CA 2302226C
Authority
CA
Canada
Prior art keywords
group
camptothecin
compound
amino
mmol
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
CA2302226A
Other languages
English (en)
French (fr)
Other versions
CA2302226A1 (en
Inventor
Dennis P. Curran
Hubert Josien
David Bom
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 CA2302226A1 publication Critical patent/CA2302226A1/en
Application granted granted Critical
Publication of CA2302226C publication Critical patent/CA2302226C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • 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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CA2302226A 1997-08-29 1998-08-26 Camptothecin analogs and methods of preparation thereof Expired - Fee Related CA2302226C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/921,102 1997-08-29
US08/921,102 US6150343A (en) 1993-06-30 1997-08-29 Camptothecin analogs and methods of preparation thereof
PCT/US1998/017683 WO1999009996A1 (en) 1997-08-29 1998-08-26 Camptothecin analogs and methods of preparation thereof

Publications (2)

Publication Number Publication Date
CA2302226A1 CA2302226A1 (en) 1999-03-04
CA2302226C true CA2302226C (en) 2010-08-24

Family

ID=25444921

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2302226A Expired - Fee Related CA2302226C (en) 1997-08-29 1998-08-26 Camptothecin analogs and methods of preparation thereof

Country Status (9)

Country Link
US (6) US6150343A (enExample)
EP (1) EP1017399B1 (enExample)
JP (1) JP4903936B2 (enExample)
AT (1) ATE418338T1 (enExample)
AU (1) AU760543B2 (enExample)
CA (1) CA2302226C (enExample)
DE (1) DE69840388D1 (enExample)
ES (1) ES2320183T3 (enExample)
WO (1) WO1999009996A1 (enExample)

Families Citing this family (17)

* 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
US6743917B2 (en) 1993-06-30 2004-06-01 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
FR2754179B1 (fr) 1996-10-08 1998-12-24 Theramex Nouvelle composition hormononale et son utilisation
US6207832B1 (en) * 1999-04-09 2001-03-27 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
WO2002062340A1 (en) * 2001-02-07 2002-08-15 University Of Kentucky Research Foundation Highly lipophilic camptothecin prodrugs, methods of preparation, and formulations thereof
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
AU2003239538A1 (en) * 2002-05-22 2003-12-12 University Of Pittsburgh Synthesis of polycyclic quinolines
CA2548543C (en) 2003-12-17 2012-01-03 Bionumerik Pharmaceuticals, Inc. Process for making camptothecin derivatives
US7346153B2 (en) * 2004-11-12 2008-03-18 International Business Machines Corporation Dynamically alerting callers of changes to menu structures in a telephone prompting system
PE20080145A1 (es) 2006-03-21 2008-02-11 Janssen Pharmaceutica Nv Tetrahidro-pirimidoazepinas como moduladores de trpv1
AU2007232206B2 (en) 2006-03-30 2013-04-04 Drais Pharmaceuticals, Inc. Camptothecin-cell penetrating peptide conjugates and pharmaceutical compositions containing the same
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
HUE031374T2 (en) * 2007-10-16 2017-07-28 Bionumerik Pharmaceuticals Inc C10-substituted camptothecin analogs
WO2009078999A1 (en) 2007-12-17 2009-06-25 Janssen Pharmaceutica N.V. Imidazolo-, oxazolo-, and thiazolopyrimidine modulators of trpv1
EP3209666B1 (en) * 2014-10-22 2019-08-21 Vivacitas Oncology Inc. Methods and systems for camptothecin analog synthesis

Family Cites Families (14)

* 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
US6743917B2 (en) * 1993-06-30 2004-06-01 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
US6211371B1 (en) 1993-06-30 2001-04-03 University Of Pittsburgh Intermediates in the synthesis of camptothecin and related compounds and synthesis thereof
US6252079B1 (en) * 1993-06-30 2001-06-26 University Of Pittsburgh Intermediates in the synthesis of camptothecin and related compounds and synthesis thereof
US5744605A (en) 1993-06-30 1998-04-28 University Of Pittsburgh Intermediates in the synthesis of (+) camptothecin and related compounds and synthesis thereof
US6136978A (en) * 1993-06-30 2000-10-24 University Of Pittsburgh Camptothecin analogs and methods of preparation thereof
DE69728152T2 (de) * 1996-08-19 2004-08-05 Bionumerik Pharmaceuticals, Inc., San Antonio Hoch-lipophile campothecin-derivate
US6169080B1 (en) * 1997-02-13 2001-01-02 Bionumerik Pharmaceuticals, Inc. Highly lipophilic camptothecin derivatives
DK1017675T3 (da) * 1997-02-14 2006-10-16 Bionumerik Pharmaceuticals Inc Stærkt lipofile camptothecinderivater
US6948279B1 (en) 1997-04-22 2005-09-27 Caldwell Manufacturing Company Support system for laterally removable sash
US6057303A (en) * 1998-10-20 2000-05-02 Bionumerik Pharmaceuticals, Inc. Highly lipophilic Camptothecin derivatives
US6403604B1 (en) * 2001-03-01 2002-06-11 California Pacific Medical Center Nitrogen-based camptothecin derivatives
US7687497B2 (en) * 2007-10-16 2010-03-30 Bionumerik Pharmaceuticals, Inc. C10-substituted camptothecin analogs

Also Published As

Publication number Publication date
US6150343A (en) 2000-11-21
AU760543B2 (en) 2003-05-15
WO1999009996A1 (en) 1999-03-04
US7271159B2 (en) 2007-09-18
ATE418338T1 (de) 2009-01-15
US20030105324A1 (en) 2003-06-05
AU9205698A (en) 1999-03-16
US6455699B1 (en) 2002-09-24
CA2302226A1 (en) 1999-03-04
US7655640B2 (en) 2010-02-02
ES2320183T3 (es) 2009-05-19
DE69840388D1 (de) 2009-02-05
JP4903936B2 (ja) 2012-03-28
US7514418B2 (en) 2009-04-07
US20070259905A1 (en) 2007-11-08
EP1017399A1 (en) 2000-07-12
JP2001513567A (ja) 2001-09-04
EP1017399A4 (en) 2002-11-13
EP1017399B1 (en) 2008-12-24
US20040029835A1 (en) 2004-02-12
US20080269169A1 (en) 2008-10-30

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