CA2392873A1 - Derives de benzo[a]phenazine-11-carboxamide et leur utilisation comme inhibiteurs communs de la topomerase i et ii - Google Patents

Derives de benzo[a]phenazine-11-carboxamide et leur utilisation comme inhibiteurs communs de la topomerase i et ii Download PDF

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Publication number
CA2392873A1
CA2392873A1 CA002392873A CA2392873A CA2392873A1 CA 2392873 A1 CA2392873 A1 CA 2392873A1 CA 002392873 A CA002392873 A CA 002392873A CA 2392873 A CA2392873 A CA 2392873A CA 2392873 A1 CA2392873 A1 CA 2392873A1
Authority
CA
Canada
Prior art keywords
benzo
phenazine
carboxylic acid
amide
dimethylamino
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.)
Abandoned
Application number
CA002392873A
Other languages
English (en)
Inventor
John Milton
Nigel Vicker
Adrian John Folkes
Shouming Wang
William Alexander Denny
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.)
Xenova Ltd
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2392873A1 publication Critical patent/CA2392873A1/fr
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/46—Phenazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un composé qui est un dérivé de benzo(a)phénazine-11-carboxamide de la formule (I) où R?1¿ à R?4¿ sont identiques ou différents et sont respectivement sélectionnés parmi un hydrogène, un halogène, hydroxy, alcoxy en C¿1?-C¿6? substitué ou non, hétéroaryloxy, alkyle en C¿1?-C¿6? Substitué ou non, nitro, cyano, azido, amidoxime, CO¿2?R?10¿, CON(R?12¿)¿2?, OCON(R?12¿), SR?10¿, SOR?11¿, SO¿2?(R¿11?), SO¿2?N(R?12¿)¿2?, N(R?12¿)¿2?, NR?10¿SO¿2?R?11¿, N(SO¿2?R?11¿)¿2?NR?10¿(CH¿2?)nCN, NR?10¿COR?11¿, OCOR?11¿ ou COR?10¿; R?5¿ à R?7¿ sont identiques ou différents et sont sélectionnés parmi un hydrogène, un halogène, hydroxy, alcoxy en C¿1?-C¿6?, alkyle en C¿1?-C¿6?, SR?10¿ et N(R?12¿)¿2?; Q représente alkylène en C¿1?-C¿6? substitué ou non par (I) alkyle en C¿1?-C¿6? Substitué ou non, (ii) hydroxy, sachant que le groupe hydroxy ne représente pas .alpha. pour un atome d'azote quelconque adjacent à Q dans la formule (I), (iii) CO¿2?R?10¿, ou (iv) CON(R?12¿); R?8¿ et R?9¿, sont identiques ou différents et représentent respectivement un hydrogène ou alkyle en C¿1?-C¿6?, ou R?8¿ et R?9¿ forment, avec l'atome d'azote auquel ils sont fixés, un noyau hétérocyclique saturé à 5 ou 6 chaînons, contenant de l'azote et pouvant contenir un hétéroatome additionnel choisi parmi oxygène, azote et soufre, ou bien R?8¿ ou R?9¿ représente une chaîne alkylène éventuellement interrompue par oxygène, azote et soufre et fixée à un atome de carbone de la chaîne d'alkylène représentée par Q pour compléter un noyau hétérocyclique saturé à 5 ou 6 chaînons et contenant de l'azote comme susmentionné; ou un de ses sels pharmaceutiquement compatibles; sous réserve qu'au moins un reste de R?1¿ à R?4¿ représente autre chose qu'un hydrogène. Ces composés, inhibiteurs de la topoisomérase I et/ou la topoisomérase II, peuvent servir à traiter des tumeurs, y compris des tumeurs qui expriment la résistance multi-médicaments.
CA002392873A 1999-12-02 2000-12-01 Derives de benzo[a]phenazine-11-carboxamide et leur utilisation comme inhibiteurs communs de la topomerase i et ii Abandoned CA2392873A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9928542.1A GB9928542D0 (en) 1999-12-02 1999-12-02 Pharmaceutical compounds
GB9928542.1 1999-12-02
PCT/GB2000/004609 WO2001046157A1 (fr) 1999-12-02 2000-12-01 Derives de benzo[a]phenazine-11-carboxamide et leur utilisation comme inhibiteurs communs de la topomerase i et ii

Publications (1)

Publication Number Publication Date
CA2392873A1 true CA2392873A1 (fr) 2001-06-28

Family

ID=10865607

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002392873A Abandoned CA2392873A1 (fr) 1999-12-02 2000-12-01 Derives de benzo[a]phenazine-11-carboxamide et leur utilisation comme inhibiteurs communs de la topomerase i et ii

Country Status (16)

Country Link
EP (1) EP1240148A1 (fr)
JP (1) JP2003518103A (fr)
KR (1) KR100767613B1 (fr)
CN (1) CN1304380C (fr)
AU (1) AU784397B2 (fr)
BR (1) BR0016093A (fr)
CA (1) CA2392873A1 (fr)
GB (2) GB9928542D0 (fr)
HK (1) HK1046133B (fr)
HU (1) HUP0300392A3 (fr)
MX (1) MXPA02005476A (fr)
MY (1) MY136029A (fr)
PL (1) PL356482A1 (fr)
TW (1) TWI280242B (fr)
WO (1) WO2001046157A1 (fr)
ZA (1) ZA200204296B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2433071A (en) * 2005-12-05 2007-06-13 Kontrakt Technology Ltd Organic acids comprising planar conjugated heterocyclic molecular system, & photoelectric layer thereof with rodlike supramolecules for use in solar cell
CN102898388B (zh) * 2012-09-26 2014-12-03 浙江工业大学 一种合成取代苯并[α]吩嗪类化合物的方法
CN103360329B (zh) * 2013-07-18 2015-11-18 中国科学院南海海洋研究所 一类吩嗪化合物及其在制备抗肿瘤药物中的应用
CN106554321B (zh) * 2015-09-25 2019-05-28 陆源 一种吩嗪类物质、其制备方法及其应用
CN113461623A (zh) * 2021-07-14 2021-10-01 长江大学 一种抗病毒化合物及其制备方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE195869T1 (de) * 1992-05-28 2000-09-15 Xenova Ltd Acridin carboxamide zur behandlung von krebs
US5696131A (en) * 1993-01-22 1997-12-09 Xenova Limited Treatment of cancers
TR199900636T2 (xx) * 1996-09-23 1999-10-21 Rutgers, The State University Of New Jersey Anti-t�m�r ajanlar� olarak ikameli/katk�l� heterosayk�llar.
WO1998045272A1 (fr) * 1997-04-07 1998-10-15 Latrobe University Inhibiteurs de la topoisomerase

Also Published As

Publication number Publication date
GB2373499A (en) 2002-09-25
GB2373499B (en) 2004-11-17
KR20020070305A (ko) 2002-09-05
HUP0300392A2 (hu) 2003-07-28
BR0016093A (pt) 2002-08-20
TWI280242B (en) 2007-05-01
HK1046133B (zh) 2005-04-15
CN1433406A (zh) 2003-07-30
CN1304380C (zh) 2007-03-14
KR100767613B1 (ko) 2007-10-19
JP2003518103A (ja) 2003-06-03
MY136029A (en) 2008-07-31
AU1718401A (en) 2001-07-03
GB9928542D0 (en) 2000-02-02
HK1046133A1 (en) 2002-12-27
GB0215275D0 (en) 2002-08-14
EP1240148A1 (fr) 2002-09-18
ZA200204296B (en) 2003-05-29
MXPA02005476A (es) 2003-09-22
WO2001046157A1 (fr) 2001-06-28
HUP0300392A3 (en) 2003-09-29
AU784397B2 (en) 2006-03-23
PL356482A1 (en) 2004-06-28

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Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued