CA2347100C - Novel indenoisoquinolines as antineoplastic agents - Google Patents

Novel indenoisoquinolines as antineoplastic agents Download PDF

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Publication number
CA2347100C
CA2347100C CA2347100A CA2347100A CA2347100C CA 2347100 C CA2347100 C CA 2347100C CA 2347100 A CA2347100 A CA 2347100A CA 2347100 A CA2347100 A CA 2347100A CA 2347100 C CA2347100 C CA 2347100C
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CA
Canada
Prior art keywords
hydrogen
group
alkoxy
alkyl
och2o
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
CA2347100A
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English (en)
French (fr)
Other versions
CA2347100A1 (en
Inventor
Mark S. Cushman
Pamela M. Nagafuji
Muthusamy Jayaraman
Yves G. Pommier
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.)
Purdue Research Foundation
Government of the United States of America
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Purdue Research Foundation
Government of the United States of America
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Publication date
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Publication of CA2347100A1 publication Critical patent/CA2347100A1/en
Application granted granted Critical
Publication of CA2347100C publication Critical patent/CA2347100C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2347100A 1998-10-14 1999-10-14 Novel indenoisoquinolines as antineoplastic agents Expired - Fee Related CA2347100C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10422698P 1998-10-14 1998-10-14
US60/104,226 1998-10-14
PCT/US1999/023900 WO2000021537A1 (en) 1998-10-14 1999-10-14 Novel indenoisoquinolines as antineoplastic agents

Publications (2)

Publication Number Publication Date
CA2347100A1 CA2347100A1 (en) 2000-04-20
CA2347100C true CA2347100C (en) 2010-12-14

Family

ID=22299324

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2347100A Expired - Fee Related CA2347100C (en) 1998-10-14 1999-10-14 Novel indenoisoquinolines as antineoplastic agents

Country Status (8)

Country Link
US (1) US6509344B1 (https=)
EP (2) EP2050452A1 (https=)
JP (1) JP4580556B2 (https=)
AT (1) ATE424204T1 (https=)
AU (1) AU765135B2 (https=)
CA (1) CA2347100C (https=)
DE (1) DE69940523D1 (https=)
WO (1) WO2000021537A1 (https=)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6956035B2 (en) 2001-08-31 2005-10-18 Inotek Pharmaceuticals Corporation Isoquinoline derivatives and methods of use thereof
US20030096833A1 (en) 2001-08-31 2003-05-22 Jagtap Prakash G. Substituted ideno[1,2-c]isoquinoline derivatives and methods of use thereof
WO2003041660A2 (en) 2001-11-14 2003-05-22 Rutgers, The State University Solubilized topoisomerase poisons
ES2311639T3 (es) 2001-11-14 2009-02-16 Rutgers, The State University Agentes citotoxicos.
JP4789414B2 (ja) * 2001-11-14 2011-10-12 ラトガーズ，ザ ステイト ユニバーシティ 可溶化トポイソメラーゼ毒性剤
ATE390923T1 (de) * 2001-11-14 2008-04-15 Univ Rutgers Topoisomerase-giftmittel
US6992089B2 (en) 2002-08-09 2006-01-31 Rutgers, The University Of New Jersey Nitro and amino substituted topoisomerase agents
WO2004014862A1 (en) * 2002-08-09 2004-02-19 Rutgers, The State University Nitro and amino substituted heterocycles as topoisomerase i targeting agents
WO2004014918A1 (en) 2002-08-09 2004-02-19 Rutgers, The State University Nitro and amino substituted topoisomerase agents
AU2003290818A1 (en) * 2002-11-12 2004-06-03 Edmond J. Lavoie Topoisomerase-targeting agents
EP1603567A4 (en) * 2003-02-28 2006-10-18 Inotek Pharmaceuticals Corp TETRACYCLIC BENZAMIDE DERIVATIVES AND METHOD OF USE THEREOF
WO2004100891A2 (en) * 2003-05-12 2004-11-25 Purdue Research Foundation Cytotoxic indeno and isoindoloisoquinolones
US20050228007A1 (en) * 2004-02-26 2005-10-13 Prakash Jagtap Isoquinoline derivatives and methods of use thereof
EP1735281A4 (en) * 2004-03-17 2009-11-04 Purdue Research Foundation Synthesis of Indinoisoquinoline Compounds and Their Use
US7495100B2 (en) * 2004-05-07 2009-02-24 Purdue Research Foundation Synthesis of indenoisoquinolines
JP2008531562A (ja) 2005-02-25 2008-08-14 イノテック ファーマシューティカルズ コーポレイション 四環アミノ化合物および四環カルボキサミド化合物およびこれらの使用法
CN101316592A (zh) 2005-08-24 2008-12-03 伊诺泰克制药公司 茚并异喹啉酮类似物及其用法
CA2629530C (en) * 2005-11-14 2014-07-08 The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services N-substituted indenoisoquinolines and syntheses thereof
US9399660B2 (en) 2005-11-14 2016-07-26 Purdue Research Foundation N-substituted indenoisoquinolines and syntheses thereof
KR20090115879A (ko) 2007-02-28 2009-11-09 이노텍 파마슈티컬스 코포레이션 인데노이소퀴놀리논 유사체와 이의 이용 방법
WO2010077663A2 (en) * 2008-12-08 2010-07-08 Inotek Pharmaceuticals Corporation Substituted tetracyclic 1h-indeno (1,2-b) pyridine-2 (5h)-one analogs thereof and uses thereof
DK2403856T3 (da) 2009-03-06 2013-04-08 Univ Rutgers Methylendioxybenzo[i]phenanthridinderivater anvendt til behandling af cancer
WO2010127363A1 (en) 2009-05-01 2010-11-04 Rutgers, The State University Of New Jersey Toposiomerase inhibitors
EP2528440A4 (en) * 2010-01-27 2013-08-07 Purdue Research Foundation SUBSTITUTED NORINDEN ISOCHINOLINE, SYNTHESIS THEREOF AND METHOD OF USE THEREOF
US9073920B2 (en) 2010-08-17 2015-07-07 Purdue Research Foundation Substituted dibenzonaphthyridines, pharmaceutical uses thereof and processes therfor
US9682990B2 (en) 2011-05-25 2017-06-20 Purdue Research Foundation Alcohol-, diol-, and carbohydrate-substituted indenoisoquinolines as topoisomerase I inhibitors
US9328073B2 (en) 2011-05-25 2016-05-03 Purdue Research Foundation Alcohol-, diol-, and carbohydrate-substituted indenoisoquinolines as topoisomerase I inhibitors
US8912213B2 (en) 2012-04-13 2014-12-16 Purdue Research Foundation Synthesis and use of dual tyrosyl-DNA phosphodiesterase I (TDP1)- topoisomerase I (TOP1) inhibitors
US9034870B2 (en) 2012-07-13 2015-05-19 Purdue Research Foundation Azaindenoisoquinoline topoisomerase I inhibitors
US8686146B2 (en) 2012-07-13 2014-04-01 Purdue Research Foundation Azaindenoisoquinoline topoisomerase I inhibitors
US10759795B2 (en) 2016-03-15 2020-09-01 Purdue Research Foundation Aza-A-ring indenoisoquinoline topoisomerase I poisons
JP2019515025A (ja) 2016-04-04 2019-06-06 ラトガース ザ ステイト ユニバーシティー オブ ニュージャージー トポイソメラーゼ毒
CN110167936A (zh) 2016-12-22 2019-08-23 珀杜研究基金会 氮杂茚并异喹啉化合物及其用途
EP3768266A4 (en) * 2018-03-20 2021-12-22 Merck Sharp & Dohme Corp. OXO-TETRAHYDRO-ISOCHINOLINE-CARBOXYLIC ACIDS AS STING INHIBITORS
WO2020023700A2 (en) * 2018-07-25 2020-01-30 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services OXYNITIDINE DERIVATIVES USEFUL AS INHIBITORS OF TOPOISOMERASE IB (Top1) AND TYROSYL-DNA PHOSPHODIESTERASE 1 (Tdp1)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3912740A (en) * 1974-02-28 1975-10-14 Us Health Method for the preparation of oxygenated benzo{8 c{9 phenanthridine compounds
US5597831A (en) * 1991-08-29 1997-01-28 Vufb A.S 6-[X-(2-hydroxyethyl) aminoalkyl]-5,11-dioxo-5,6-dihydro-11-H-indeno[1,2-c]isoquinolines and their use as antineoplastic agents
CZ281473B6 (cs) * 1991-08-29 1996-10-16 Vúfb, A.S. Deriváty 6-/X-(2-hydroxyethyl)aminoalkyl/-5,11 -dioxo-5,6-dihydro-11H-indeno/1,2-c/-isochinolinu a způsob jejich výroby
JP3141148B2 (ja) * 1995-08-08 2001-03-05 大鵬薬品工業株式会社 縮合インダン誘導体及びその塩
JP3643916B2 (ja) * 1995-11-17 2005-04-27 大鵬薬品工業株式会社 新規な縮合インデン誘導体又はその塩

Also Published As

Publication number Publication date
EP1123099A1 (en) 2001-08-16
ATE424204T1 (de) 2009-03-15
US6509344B1 (en) 2003-01-21
DE69940523D1 (de) 2009-04-16
EP1123099A4 (en) 2002-08-21
AU765135B2 (en) 2003-09-11
JP2002527396A (ja) 2002-08-27
JP4580556B2 (ja) 2010-11-17
EP1123099B1 (en) 2009-03-04
AU1204300A (en) 2000-05-01
EP2050452A1 (en) 2009-04-22
WO2000021537A1 (en) 2000-04-20
CA2347100A1 (en) 2000-04-20

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CA2347100C (en) Novel indenoisoquinolines as antineoplastic agents
Jayaraman et al. Synthesis of new dihydroindeno [1, 2-c] isoquinoline and indenoisoquinolinium chloride topoisomerase I inhibitors having high in vivo anticancer activity in the hollow fiber animal model
Cushman et al. Synthesis of new indeno [1, 2-c] isoquinolines: cytotoxic non-camptothecin topoisomerase I inhibitors
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