JP5328357B2 - 化学放射線増感剤としてのカンプトテシン誘導体 - Google Patents

化学放射線増感剤としてのカンプトテシン誘導体 Download PDF

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Publication number
JP5328357B2
JP5328357B2 JP2008536850A JP2008536850A JP5328357B2 JP 5328357 B2 JP5328357 B2 JP 5328357B2 JP 2008536850 A JP2008536850 A JP 2008536850A JP 2008536850 A JP2008536850 A JP 2008536850A JP 5328357 B2 JP5328357 B2 JP 5328357B2
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cpt
hydroxy
lower alkyl
amino
hydrogen
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JP2008536850A
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JP2009512714A5 (enExample
JP2009512714A (ja
Inventor
リ−シ・ヤン
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Catholic Healthcare West
Sutter West Bay Hospitals
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Catholic Healthcare West
Sutter West Bay Hospitals
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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
    • C07D491/12—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
    • 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
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (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)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
JP2008536850A 2005-10-21 2006-10-19 化学放射線増感剤としてのカンプトテシン誘導体 Expired - Fee Related JP5328357B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US72892405P 2005-10-21 2005-10-21
US60/728,924 2005-10-21
US11/444,150 2006-05-30
US11/444,150 US7875602B2 (en) 2005-10-21 2006-05-30 Camptothecin derivatives as chemoradiosensitizing agents
PCT/US2006/041175 WO2007048002A2 (en) 2005-10-21 2006-10-19 Camptothecin derivatives as chemoradiosensitizing agents

Publications (3)

Publication Number Publication Date
JP2009512714A JP2009512714A (ja) 2009-03-26
JP2009512714A5 JP2009512714A5 (enExample) 2009-12-03
JP5328357B2 true JP5328357B2 (ja) 2013-10-30

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JP2008536850A Expired - Fee Related JP5328357B2 (ja) 2005-10-21 2006-10-19 化学放射線増感剤としてのカンプトテシン誘導体

Country Status (11)

Country Link
US (3) US7875602B2 (enExample)
EP (1) EP1951231B1 (enExample)
JP (1) JP5328357B2 (enExample)
KR (1) KR101320160B1 (enExample)
CN (1) CN101300009B (enExample)
AU (1) AU2006304811C1 (enExample)
CA (1) CA2626032C (enExample)
ES (1) ES2428088T3 (enExample)
NZ (2) NZ593706A (enExample)
TW (1) TWI402270B (enExample)
WO (1) WO2007048002A2 (enExample)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10046022B2 (en) 2015-05-29 2018-08-14 Toagosei Co. Ltd. Synthetic peptide that increases radiosensitivity of tumor cells and use of same
US10981953B2 (en) 2013-12-26 2021-04-20 Toagosei Co, Ltd. Method for promoting expression of calreticulin, and synthetic peptide for use in method for promoting expression of calreticulin

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101402640B (zh) * 2008-09-02 2011-06-15 暨南大学 双酯化喜树碱衍生物及其制备方法和应用
DE102009004204A1 (de) * 2009-01-09 2010-07-15 Christian-Albrechts-Universität Zu Kiel Verfahren zur verbesserten Bioaktivierung von Arzneistoffen
US8168648B2 (en) * 2009-03-06 2012-05-01 Taiwan Liposome Co., Ltd. Camptothecin derivatives and uses thereof
US8575188B2 (en) 2009-06-17 2013-11-05 Threshold Pharmaceuticals, Inc. Camptothecin derivatives
US10391056B2 (en) 2011-11-03 2019-08-27 Taiwan Lipsome Company, LTD. Pharmaceutical compositions of hydrophobic camptothecin derivatives
US10980798B2 (en) 2011-11-03 2021-04-20 Taiwan Liposome Company, Ltd. Pharmaceutical compositions of hydrophobic camptothecin derivatives
US20140135357A1 (en) * 2012-11-12 2014-05-15 Taiwan Liposome Company, Ltd. Dose regime for camptothecin derivatives
AU2014216178B2 (en) 2013-02-15 2018-06-28 KALA BIO, Inc. Therapeutic compounds and uses thereof
US9688688B2 (en) 2013-02-20 2017-06-27 Kala Pharmaceuticals, Inc. Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof
EP2958895B1 (en) 2013-02-20 2020-08-19 Kala Pharmaceuticals, Inc. Therapeutic compounds and uses thereof
US9890173B2 (en) 2013-11-01 2018-02-13 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
CA2928658A1 (en) 2013-11-01 2015-05-07 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
US10087194B2 (en) 2015-10-27 2018-10-02 California Pacific Medical Center Podophyllotoxin derivatives and their use
ES2806624T3 (es) 2015-10-27 2021-02-18 California Pacific Medical Center Derivados de podofilotoxina y su uso
AU2017324713B2 (en) 2016-09-08 2020-08-13 KALA BIO, Inc. Crystalline forms of therapeutic compounds and uses thereof
CA3036340A1 (en) 2016-09-08 2018-03-15 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
CA3036065A1 (en) 2016-09-08 2018-03-15 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
CN114341141A (zh) 2019-07-11 2022-04-12 太阳医药高级研究有限公司 具有二硫部分和哌嗪部分的喜树碱衍生物
JP2023512214A (ja) 2020-01-28 2023-03-24 リフレクション メディカル， インコーポレイテッド 放射性核種および外部ビーム放射線療法の共同最適化

Family Cites Families (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US554990A (en) * 1896-02-18 Target-throwing trap
US4399282A (en) 1979-07-10 1983-08-16 Kabushiki Kaisha Yakult Honsha Camptothecin derivatives
JPS6019790A (ja) 1983-07-14 1985-01-31 Yakult Honsha Co Ltd 新規なカンプトテシン誘導体
US5196413A (en) 1984-12-10 1993-03-23 Johnson Matthey, Inc. Platinum complexes and the like
US4663161A (en) 1985-04-22 1987-05-05 Mannino Raphael J Liposome methods and compositions
US5032617A (en) 1985-05-03 1991-07-16 Sri International Substituted benzamide radiosensitizers
US5041653A (en) 1985-05-03 1991-08-20 Sri International Substituted benzamide radiosensitizers
US5175278A (en) 1985-06-28 1992-12-29 Merck & Co., Inc. Heteropolysaccharide S-657
US4727068A (en) 1985-10-23 1988-02-23 Johnson Matthey, Inc. Radiosensitization by cobalt and Fe(III) complexes
US5175287A (en) 1986-09-25 1992-12-29 S R I International Process for preparing 1,2,4-benzotriazine oxides
US5026694A (en) 1987-04-13 1991-06-25 The British Columbia Cancer Foundation Platinum complexes with one radiosensitizing ligand
US4921963A (en) 1987-04-13 1990-05-01 British Columbia Cancer Foundation Platinum complexes with one radiosensitizing ligand
CA1329206C (en) 1987-06-10 1994-05-03 Tsutomu Kagiya Fluorine-containing nitroazole derivatives and radiosensitizer comprising the same
US5304654A (en) 1987-06-10 1994-04-19 Yasunori Nishijima Fluorine-containing nitroimidazole compounds
US4797397A (en) 1987-07-31 1989-01-10 Warner-Lambert Company 2-nitroimidazole derivatives useful as radiosensitizers for hypoxic tumor cells
US4943579A (en) 1987-10-06 1990-07-24 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Water soluble prodrugs of camptothecin
JPH0819111B2 (ja) 1987-10-22 1996-02-28 ポーラ化成工業株式会社 ２―ニトロイミダゾール誘導体及びこれを有効成分とする放射線増感剤
US5036096A (en) 1988-11-25 1991-07-30 Warner-Lambert Company Aziridino derivatives of nitroimidazoles and pharmaceutical compositions of selected derivatives
US4954515A (en) 1988-11-25 1990-09-04 Warner-Lambert Company Haloalkylaminomethyl-2-nitro-1H-imidazoles
US5043165A (en) 1988-12-14 1991-08-27 Liposome Technology, Inc. Novel liposome composition for sustained release of steroidal drugs
IL92597A0 (en) 1988-12-14 1990-08-31 Yasunori Nishijima President K Novel fluorine-containing 2-nitroimidazole derivatives and radiosensitizer comprising the same
US5077057A (en) 1989-04-05 1991-12-31 The Regents Of The University Of California Preparation of liposome and lipid complex compositions
US5549910A (en) 1989-03-31 1996-08-27 The Regents Of The University Of California Preparation of liposome and lipid complex compositions
US5013556A (en) 1989-10-20 1991-05-07 Liposome Technology, Inc. Liposomes with enhanced circulation time
US5294715A (en) 1991-02-01 1994-03-15 University Of Pittsburgh Acridine-intercalator based hypoxia selective cytotoxins
CA2097163C (en) 1992-06-01 2002-07-30 Marianna Foldvari Topical patch for liposomal drug delivery system
MX9304399A (es) 1992-07-31 1994-02-28 Warner Lambert Co Proceso novedoso para preparar [[2-bromoetil)-amino]metil]-2-nitro-1h-imidazol-1-etanol quiral y compuestos relacionados.
US5552156A (en) 1992-10-23 1996-09-03 Ohio State University Liposomal and micellular stabilization of camptothecin drugs
US5631237A (en) 1992-12-22 1997-05-20 Dzau; Victor J. Method for producing in vivo delivery of therapeutic agents via liposomes
GB9320781D0 (en) 1993-10-08 1993-12-01 Erba Carlo Spa Polymer-bound camptothecin derivatives
US5965566A (en) 1993-10-20 1999-10-12 Enzon, Inc. High molecular weight polymer-based prodrugs
US5919455A (en) 1993-10-27 1999-07-06 Enzon, Inc. Non-antigenic branched polymer conjugates
US5646159A (en) 1994-07-20 1997-07-08 Research Triangle Institute Water-soluble esters of camptothecin compounds
GB9504065D0 (en) 1995-03-01 1995-04-19 Pharmacia Spa Poly-pyrrolecarboxamidonaphthalenic acid derivatives
US5736156A (en) 1995-03-22 1998-04-07 The Ohio State University Liposomal anf micellular stabilization of camptothecin drugs
US6060604A (en) 1995-03-31 2000-05-09 Florida State University Pharmaceutical compounds comprising polyamines substituted with electron-affinic groups
JPH08333370A (ja) 1995-06-08 1996-12-17 Kyorin Pharmaceut Co Ltd 水に可溶な新規フルオロエチルカンプトテシン誘導体、及びその製造方法
US6339091B1 (en) 1995-06-21 2002-01-15 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) Comptothecin analogues, preparation methods therefor, use thereof as drugs, and pharmaceutical compositions containing said analogues
GB9512670D0 (en) 1995-06-21 1995-08-23 Sod Conseils Rech Applic Camptothecin analogues
CN1211919A (zh) 1995-09-13 1999-03-24 佛罗里达州立大学 放射增敏性紫杉烷及其药物制剂
WO1997019085A1 (en) 1995-11-22 1997-05-29 Research Triangle Institute Camptothecin compounds with combined topoisomerase i inhibition and dna alkylation properties
US6096336A (en) 1996-01-30 2000-08-01 The Stehlin Foundation For Cancer Research Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs
US5731316A (en) 1996-01-30 1998-03-24 The Stehlin Foundation For Cancer Research Derivatives of camptothecin and methods of treating cancer using these derivatives
US5874105A (en) 1996-01-31 1999-02-23 Collaborative Laboratories, Inc. Lipid vesicles formed with alkylammonium fatty acid salts
ATE261974T1 (de) 1996-08-19 2004-04-15 Bionumerik Pharmaceuticals Inc Hoch-lipophile campothecin-derivate
AU4424797A (en) 1996-09-18 1998-04-14 Dragoco Inc. Liposome encapsulated active agent dry powder composition
AU739028B2 (en) 1996-09-27 2001-10-04 Bristol-Myers Squibb Company Hydrolyzable prodrugs for delivery of anticancer drugs to metastatic cells
ATE210673T1 (de) 1996-09-30 2001-12-15 Bayer Ag Glycokonjugate von modifizierten camptothecin- derivaten (20-o-verknüpfung)
KR100219562B1 (ko) * 1996-10-28 1999-09-01 윤종용 반도체장치의 다층 배선 형성방법
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
US5827533A (en) 1997-02-06 1998-10-27 Duke University Liposomes containing active agents aggregated with lipid surfactants
ES2262223T3 (es) 1997-02-14 2006-11-16 Bionumerik Pharmaceuticals, Inc. Derivados de camptotecina altamente lipofilos.
JP3209509B2 (ja) * 1997-03-28 2001-09-17 インターナショナル・ビジネス・マシーンズ・コーポレーション ディスク状記録装置及びディスクドライブ装置
ID23424A (id) 1997-05-14 2000-04-20 Bayer Ag Glikokonjugat dari 20(s)-kamptotesin
GB9721070D0 (en) 1997-10-03 1997-12-03 Pharmacia & Upjohn Spa Bioactive derivatives of camptothecin
US5935949A (en) 1998-03-20 1999-08-10 Trustees Of Dartmouth College Use of androgen therapy in fibromyalgia and chronic fatigue syndrome
US6153655A (en) 1998-04-17 2000-11-28 Enzon, Inc. Terminally-branched polymeric linkers and polymeric conjugates containing the same
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
US6281223B1 (en) 1999-04-13 2001-08-28 Supergen, Inc. Radioenhanced camptothecin derivative cancer treatments
WO2000066127A1 (en) 1999-05-04 2000-11-09 Bionumerik Pharmaceuticals, Inc. Novel highly lipophilic camptothecin analogs
US6765019B1 (en) 1999-05-06 2004-07-20 University Of Kentucky Research Foundation Permeable, water soluble, non-irritating prodrugs of chemotherapeutic agents with oxaalkanoic acids
US6228855B1 (en) * 1999-08-03 2001-05-08 The Stehlin Foundation For Cancer Research Aromatic esters of camptothecins and methods to treat cancers
CA2391534A1 (en) * 1999-11-15 2001-05-25 Drug Innovation & Design, Inc. Selective cellular targeting: multifunctional delivery vehicles
US6423707B1 (en) 2000-08-28 2002-07-23 California Pacific Medical Center Nitroimidazole ester analogues and therapeutic applications
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
GB0119578D0 (en) 2001-08-10 2001-10-03 Pharmacia & Upjohn Spa Fluoro linkers
AU2003243380A1 (en) 2002-06-03 2003-12-19 California Pacific Medical Center Nitrogen-based homo-camptothecin derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10981953B2 (en) 2013-12-26 2021-04-20 Toagosei Co, Ltd. Method for promoting expression of calreticulin, and synthetic peptide for use in method for promoting expression of calreticulin
US10046022B2 (en) 2015-05-29 2018-08-14 Toagosei Co. Ltd. Synthetic peptide that increases radiosensitivity of tumor cells and use of same

Also Published As

Publication number Publication date
CA2626032C (en) 2011-12-06
AU2006304811C1 (en) 2012-11-01
NZ593706A (en) 2012-11-30
TWI402270B (zh) 2013-07-21
NZ567454A (en) 2011-07-29
US20110184009A1 (en) 2011-07-28
TW200730532A (en) 2007-08-16
AU2006304811B2 (en) 2012-03-22
WO2007048002A2 (en) 2007-04-26
US7875602B2 (en) 2011-01-25
WO2007048002A3 (en) 2007-09-13
EP1951231A4 (en) 2010-09-22
JP2009512714A (ja) 2009-03-26
US8563537B2 (en) 2013-10-22
CA2626032A1 (en) 2007-04-26
ES2428088T3 (es) 2013-11-05
KR101320160B1 (ko) 2013-10-23
EP1951231A2 (en) 2008-08-06
US8779138B2 (en) 2014-07-15
HK1115321A1 (en) 2008-11-28
AU2006304811A1 (en) 2007-04-26
US20070093432A1 (en) 2007-04-26
EP1951231B1 (en) 2013-07-31
CN101300009A (zh) 2008-11-05
KR20080086436A (ko) 2008-09-25
US20080318873A1 (en) 2008-12-25
CN101300009B (zh) 2013-04-03

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