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

Condensed n-acylindoles as antitumor agents Download PDF

Info

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)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (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
GB9707394.4 1997-04-10
GBGB9707394.4A GB9707394D0 (en) 1997-04-10 1997-04-10 Further cyclopropylindoles and their seco precursors, and their use as prodrugs
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 (OSRAM)
JP (1) JP4155598B2 (OSRAM)
AT (1) ATE310725T1 (OSRAM)
AU (1) AU721037B2 (OSRAM)
CA (1) CA2265874C (OSRAM)
DE (1) DE69734722T2 (OSRAM)
ES (1) ES2253786T3 (OSRAM)
NZ (1) NZ334344A (OSRAM)
WO (1) WO1998011101A2 (OSRAM)

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
ES2260570T3 (es) 1998-08-27 2006-11-01 Spirogen Limited Pirrolobenziodiazepinas dimericas.
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
BR0110414A (pt) * 2000-04-28 2003-02-11 Baxter Healthcare Sa Derivados de 2-acil indol e seu uso como agentes antitumores
WO2001083448A2 (de) * 2000-05-02 2001-11-08 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
DE60211905T2 (de) * 2001-02-22 2007-01-18 School Of Pharmacy, University Of London Benz-indol- und benzo-chinolin-derivate als prodrugs zur tumorbehandlung
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
US20050032868A1 (en) * 2003-05-02 2005-02-10 Garofalo Albert W. Selected substituted pyrazole derivatives and related compounds as bradykinin B1 receptor antagonists
TW200509910A (en) 2003-05-02 2005-03-16 Elan Pharm Inc Substituted pyrazole derivatives and related compounds as bradykinin B1 receptor antagonists
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
US8940784B2 (en) * 2006-02-02 2015-01-27 Syntarga B.V. 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
TW200900059A (en) 2007-02-21 2009-01-01 Medarex Inc Chemical linkers with single amino acids and conjugates thereof
US9901567B2 (en) 2007-08-01 2018-02-27 Syntarga B.V. Substituted CC-1065 analogs and their conjugates
RU2562232C2 (ru) 2008-11-03 2015-09-10 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
HUE030846T2 (en) 2010-04-21 2017-06-28 Syntarga Bv Conjugates of cc-1065 analogs and bifunctional linkers
PL3092010T3 (pl) 2014-01-10 2019-01-31 Synthon Biopharmaceuticals B.V. Sposób oczyszczania połączonych cysteiną koniugatów przeciwciało-lek
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
HRP20160697T1 (hr) 2014-01-10 2016-07-15 Synthon Biopharmaceuticals B.V. Duokarmicin adcs koji pokazuje poboljšanu antitumorsku aktivnost in vivo
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
JP2598819B2 (ja) * 1986-12-19 1997-04-09 ジ・アップジョン・カンパニー 新規なｃｃ‐１０６５同族体
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
KR100208957B1 (ko) * 1990-04-25 1999-07-15 로렌스 티. 마이젠헬더 신규한 cc-1065 유사체
GB9516943D0 (en) * 1995-08-18 1995-10-18 Cancer Soc Auckland Div Nz Inc Novel cyclopropylindoles and their secoprecursors,and their use as prodrugs
US6548530B1 (en) * 1995-10-03 2003-04-15 The Scripps Research Institute CBI analogs of CC-1065 and the duocarmycins
EP0888301B1 (en) * 1996-03-08 2005-08-10 The Scripps Research Institute Mcbi analogs of cc-1065 and the duocarmycins

Also Published As

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

Similar Documents

Publication Publication Date Title
CA2265874C (en) Condensed n-acylindoles as antitumor agents
US6130237A (en) Condensed N-aclyindoles as antitumor agents
US6271231B1 (en) Pharmaceutically active compounds
US5985909A (en) Cyclopropylindoles and their seco precursors, and their use as prodrugs
CN110981870B (zh) 基于pH和GSH双重响应的β-咔啉-环烯酮衍生物及其用途
EA006371B1 (ru) Противовоспалительные конденсированные пирролокарбазолы
CA2368205A1 (en) N-protected amines and their use as prodrugs
JP2004529887A (ja) 腫瘍治療のためのプロドラッグとしてのピロロ−インドールおよびピロロ−キノリン誘導体
AU2005296389B2 (en) Nitrobenzindoles and their use in cancer therapy
JP4862120B2 (ja) 腫瘍治療のためのプロドラッグとしてのベンズ−インドールおよびベンゾ−キノリン誘導体
WO2003097635A1 (en) 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
US6251933B1 (en) Seco precursors of cyclopropylindolines and their use as prodrugs
CN116239640B (zh) 吉西他滨前药及其医药用途
AU728053B2 (en) Precursors of cyclopropylindoles and their use as prodrugs
US6458792B1 (en) Compounds
JP2007291050A (ja) ピログルタミン酸誘導体の合成および用途
JP2004509897A (ja) シクロヘキシルアミン誘導体の立体選択的製造方法
WO2025247357A1 (zh) 一类氧代芳杂环结构的cd73抑制剂、及其制法和药物组合物与用途
JPH08151380A (ja) ビス（トリフルオロメチルピロロインドールカルボン酸エステル）誘導体及びその製造方法
JPH0834788A (ja) ピロロベンゾカルバゾール誘導体及びその製造方法
JPH0834787A (ja) ピロロカルバゾール誘導体及びその製造方法
JPH0834786A (ja) トリフルオロメチルピロロインドール誘導体及びその製造方法
JPH06122684A (ja) ピロロインドールジカルボン酸ジエステル誘導体及びその製造方法
HK1104294A (en) Oxazolidinones containing oxindoles as antibacterial agents

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed