CA2265874C - Condensed n-acylindoles as antitumor agents - Google Patents

Condensed n-acylindoles as antitumor agents Download PDF

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Publication number
CA2265874C
CA2265874C CA002265874A CA2265874A CA2265874C CA 2265874 C CA2265874 C CA 2265874C CA 002265874 A CA002265874 A CA 002265874A CA 2265874 A CA2265874 A CA 2265874A CA 2265874 C CA2265874 C CA 2265874C
Authority
CA
Canada
Prior art keywords
indole
chloromethyl
dihydro
mmol
benz
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
CA002265874A
Other languages
English (en)
French (fr)
Other versions
CA2265874A1 (en
Inventor
William Alexander Denny
Moana Tercel
Graham John Atwell
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.)
Auckland Uniservices Ltd
Original Assignee
Auckland Uniservices Ltd
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
Priority claimed from GBGB9619082.2A external-priority patent/GB9619082D0/en
Priority claimed from GBGB9707394.4A external-priority patent/GB9707394D0/en
Application filed by Auckland Uniservices Ltd filed Critical Auckland Uniservices Ltd
Publication of CA2265874A1 publication Critical patent/CA2265874A1/en
Application granted granted Critical
Publication of CA2265874C publication Critical patent/CA2265874C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA002265874A 1996-09-12 1997-09-12 Condensed n-acylindoles as antitumor agents Expired - Fee Related CA2265874C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GBGB9619082.2A GB9619082D0 (en) 1996-09-12 1996-09-12 Further cyclopropylindoles and their seco precursors,and their use as prodrugs
GB9619082.2 1997-04-10
GBGB9707394.4A GB9707394D0 (en) 1997-04-10 1997-04-10 Further cyclopropylindoles and their seco precursors, and their use as prodrugs
GB9707394.4 1997-04-10
PCT/NZ1997/000117 WO1998011101A2 (en) 1996-09-12 1997-09-12 Condensed n-aclyindoles as antitumor agents

Publications (2)

Publication Number Publication Date
CA2265874A1 CA2265874A1 (en) 1998-03-19
CA2265874C true CA2265874C (en) 2007-08-28

Family

ID=26310030

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002265874A Expired - Fee Related CA2265874C (en) 1996-09-12 1997-09-12 Condensed n-acylindoles as antitumor agents

Country Status (9)

Country Link
EP (1) EP0938474B1 (enExample)
JP (1) JP4155598B2 (enExample)
AT (1) ATE310725T1 (enExample)
AU (1) AU721037B2 (enExample)
CA (1) CA2265874C (enExample)
DE (1) DE69734722T2 (enExample)
ES (1) ES2253786T3 (enExample)
NZ (1) NZ334344A (enExample)
WO (1) WO1998011101A2 (enExample)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9818730D0 (en) 1998-08-27 1998-10-21 Univ Portsmouth Collections of compounds
DK1193270T3 (da) 1998-08-27 2003-09-15 Spirogen Ltd Pyrrolobenzodiazepiner
GB9909612D0 (en) * 1999-04-26 1999-06-23 Cancer Res Campaign Tech N-protected amines and their use as prodrugs
US6909006B1 (en) 1999-08-27 2005-06-21 Spirogen Limited Cyclopropylindole derivatives
RU2002132253A (ru) * 2000-04-28 2004-07-10 Бакстэ Хелскеа СА (CH) Производные 2-ацилиндола, их применение (варианты) и способ получения, лекарственное средство и способ его получения, противоопухолевое средство и способ его получения
DE50104114D1 (de) 2000-05-02 2004-11-18 Tietze Lutz F Neue prodrugs von 6-hydroxy-2,3-dihydro-1h-indolen, 5-hydroxy-1,2-dihydro-3h-pyrrolo 3,2-e]indolen und 5-hydroxy-1,2-dihydro-3h-benzo e]indolen sowie von 6-hydroxy-1,2,3,4-tetrahydro-benzo f]chinolin-derivaten für eine selektive krebstherapie
EP1408960B1 (en) 2001-02-22 2006-05-31 School Of Pharmacy, University Of London Benz-indole and benzo-quinoline derivatives as prodrugs for tumour treatment
US7235578B2 (en) * 2002-05-17 2007-06-26 Auckland Uniservices Limited Processes for preparing 3-substituted 1-(chloromethyl)-1,2-dihydro-3H-[ring fused indol-5-yl-(amine-derived)] compounds and analogues thereof, and to products obtained therefrom
GB0226593D0 (en) 2002-11-14 2002-12-24 Consultants Ltd Compounds
US7417152B2 (en) 2003-05-02 2008-08-26 Elan Pharmaceuticals, Inc. 4-bromo-5-(2-chloro-benzoylamino)-1H-pyrazole-3-carboxylic acid amide derivatives and related compounds as bradykinin B1 receptor antagonists for the treatment of inflammatory diseases
EP1635821B1 (en) * 2003-05-02 2009-07-08 Elan Pharmaceuticals, Inc. 4-bromo-5-(2-chloro-benzoylamino)-1h-pyrazole-3-carboxylic acid (phenyl)amide derivatives and related compounds as bradykinin b1 receptor antagonists for the treatment of inflammatory diseases
GB0321295D0 (en) 2003-09-11 2003-10-15 Spirogen Ltd Synthesis of protected pyrrolobenzodiazepines
NZ536107A (en) * 2004-10-22 2007-06-29 Auckland Uniservices Ltd Nitrobenzindoles and their use in cancer therapy
WO2007059404A2 (en) * 2005-11-10 2007-05-24 Medarex, Inc. Duocarmycin derivatives as novel cytotoxic compounds and conjugates
AU2007210377B2 (en) * 2006-02-02 2012-08-09 Georg-August-Universitat Gottingen Stiftung Offentlichen Rechts (Ohne Bereich Humanmedizin) Water-soluble CC-1065 analogs and their conjugates
WO2008039087A2 (en) * 2006-09-29 2008-04-03 Auckland Uniservices Limited Indoline derivatives and uses thereof
TWI412367B (zh) 2006-12-28 2013-10-21 Medarex Llc 化學鏈接劑與可裂解基質以及其之綴合物
KR20090122439A (ko) 2007-02-21 2009-11-30 메다렉스, 인코포레이티드 단일 아미노산을 갖는 화학적 링커 및 이의 접합체
US9901567B2 (en) 2007-08-01 2018-02-27 Syntarga B.V. Substituted CC-1065 analogs and their conjugates
RU2628069C2 (ru) 2008-11-03 2017-08-14 Синтарга Б.В. Новые аналоги сс-1065 и их конъюгаты
DE102009051438A1 (de) 2009-10-30 2011-05-05 Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts Fluoreszenzfarbstoffe
LT3108886T (lt) 2010-04-21 2020-08-25 Syntarga B.V. Cc-1065 analogų ir bifunkcinių jungtukų konjugatai
JP6224268B2 (ja) 2014-01-10 2017-11-01 シントン・バイオファーマシューティカルズ・ビー．ブイ．Ｓｙｎｔｈｏｎ Ｂｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｂ．Ｖ． 子宮内膜癌の治療において使用するためのデュオカルマイシンａｄｃ
TR201810856T4 (tr) 2014-01-10 2018-08-27 Synthon Biopharmaceuticals Bv CYS'le bağlı antikor-ilaç konjugatlarını saflaştırmak için usul.
HUE029255T2 (en) 2014-01-10 2017-02-28 Synthon Biopharmaceuticals Bv Duocarmycin adcs showing improved in vivo antitumor activity
CN108653288B (zh) * 2018-05-29 2020-05-05 福建医科大学孟超肝胆医院(福州市传染病医院) 一种乏氧响应聚合物纳米粒及其应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988004659A2 (en) * 1986-12-19 1988-06-30 The Upjohn Company Novel cc-1065 analogs
JP2642165B2 (ja) * 1988-07-22 1997-08-20 協和醗酵工業株式会社 新規ｄｃ−８９化合物およびその製造法
AU648313B2 (en) * 1990-04-25 1994-04-21 Pharmacia & Upjohn Company Novel CC-1065 analogs
GB9516943D0 (en) * 1995-08-18 1995-10-18 Cancer Soc Auckland Div Nz Inc Novel cyclopropylindoles and their secoprecursors,and their use as prodrugs
WO1997012862A1 (en) * 1995-10-03 1997-04-10 The Scripps Research Institute Cbi analogs of cc-1065 and the duocarmycins
JP2000506168A (ja) * 1996-03-08 2000-05-23 ザ スクリップス リサーチ インスティテュート Ｃｃ―１０６５及びデュオカマイシンのｍｃｂｉ類似体

Also Published As

Publication number Publication date
AU721037B2 (en) 2000-06-22
CA2265874A1 (en) 1998-03-19
EP0938474A2 (en) 1999-09-01
DE69734722D1 (de) 2005-12-29
WO1998011101A2 (en) 1998-03-19
NZ334344A (en) 2000-08-25
WO1998011101A3 (en) 1998-04-23
DE69734722T2 (de) 2006-07-20
ATE310725T1 (de) 2005-12-15
JP4155598B2 (ja) 2008-09-24
EP0938474B1 (en) 2005-11-23
ES2253786T3 (es) 2006-06-01
JP2000517292A (ja) 2000-12-26
AU4403997A (en) 1998-04-02

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