WO2001046157A1 - 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
WO2001046157A1
WO2001046157A1 PCT/GB2000/004609 GB0004609W WO0146157A1 WO 2001046157 A1 WO2001046157 A1 WO 2001046157A1 GB 0004609 W GB0004609 W GB 0004609W WO 0146157 A1 WO0146157 A1 WO 0146157A1
Authority
WO
WIPO (PCT)
Prior art keywords
benzo
carboxylic acid
amide
ethyl
dimethylamino
Prior art date
Application number
PCT/GB2000/004609
Other languages
English (en)
Inventor
John Milton
Nigel Vicker
Adrian John Folkes
Shouming Wang
William Alexander Denny
Original Assignee
Xenova Limited
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 to AU17184/01A priority Critical patent/AU784397B2/en
Application filed by Xenova Limited filed Critical Xenova Limited
Priority to PL00356482A priority patent/PL356482A1/xx
Priority to MXPA02005476A priority patent/MXPA02005476A/es
Priority to US10/148,601 priority patent/US20030139409A1/en
Priority to JP2001547068A priority patent/JP2003518103A/ja
Priority to EP00979799A priority patent/EP1240148A1/fr
Priority to HU0300392A priority patent/HUP0300392A3/hu
Priority to CA002392873A priority patent/CA2392873A1/fr
Priority to GB0215275A priority patent/GB2373499B/en
Priority to BR0016093-8A priority patent/BR0016093A/pt
Publication of WO2001046157A1 publication Critical patent/WO2001046157A1/fr
Priority to HK02107392.7A priority patent/HK1046133B/zh
Priority to US11/024,759 priority patent/US7132419B2/en

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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

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  • 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 R1 à R4 sont identiques ou différents et sont respectivement sélectionnés parmi un hydrogène, un halogène, hydroxy, alcoxy en C¿1?-C6 substitué ou non, hétéroaryloxy, alkyle en C1-C6 Substitué ou non, nitro, cyano, azido, amidoxime, CO2R?10, CON(R12)¿2, OCON(R?12), SR10, SOR11, SO¿2(R11), SO2N(R12)2, N(R12)2, NR10SO2R11, N(SO¿2R?11)2NR10(CH2)nCN, NR?10COR11, OCOR11 ou COR10; R5 à R7¿ sont identiques ou différents et sont sélectionnés parmi un hydrogène, un halogène, hydroxy, alcoxy en C¿1?-C6, alkyle en C1-C6, SR?10 et N(R12)¿2; Q représente alkylène en C1-C6 substitué ou non par (I) alkyle en C1-C6 Substitué ou non, (ii) hydroxy, sachant que le groupe hydroxy ne représente pas α pour un atome d'azote quelconque adjacent à Q dans la formule (I), (iii) CO2R10, ou (iv) CON(R?12); R8 et R9¿, sont identiques ou différents et représentent respectivement un hydrogène ou alkyle en C¿1?-C6, ou R?8 et R9¿ 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 R8 ou R9 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 R1 à R4 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.
PCT/GB2000/004609 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 WO2001046157A1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
EP00979799A EP1240148A1 (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
PL00356482A PL356482A1 (en) 1999-12-02 2000-12-01 Benzo[a]phenazin-11-carboxamide derivatives and their use as joint inhibitors of topomerase i and ii
MXPA02005476A MXPA02005476A (es) 1999-12-02 2000-12-01 Derivados de benzo(a)fenacin-11-carboxamidas y su uso como inhibidores de topoisomerasa i y ii.
US10/148,601 US20030139409A1 (en) 1999-12-02 2000-12-01 Benzo[A] [phenazin-11-carboxamide derivatives and their use as joint inhibitors of topomerase I and II
JP2001547068A JP2003518103A (ja) 1999-12-02 2000-12-01 ベンゾ［ａ］フェナジン−１１−カルボキサミド誘導体およびトポメラーゼｉおよびｉｉの同時インヒビターとしてのそれらの使用
AU17184/01A AU784397B2 (en) 1999-12-02 2000-12-01 Benzo(A)phenazin-11-carboxamide derivatives and their use as joint inhibitors of topomerase I and II
HU0300392A HUP0300392A3 (en) 1999-12-02 2000-12-01 Benzo[a]phenazin-11-carboxamide derivatives, their use for producing pharmaceutical compositions with effect joint inhibitors of topomerase i and ii, process for their preparation and their intermediates
BR0016093-8A BR0016093A (pt) 1999-12-02 2000-12-01 Composto, processo para produzir o mesmo, uso de um composto, e, composição farmacêutica
GB0215275A GB2373499B (en) 1999-12-02 2000-12-01 Pharmaceutical compounds
CA002392873A 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
HK02107392.7A HK1046133B (zh) 1999-12-02 2002-10-10 藥物化合物
US11/024,759 US7132419B2 (en) 1999-12-02 2004-12-30 Pharmaceutical compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9928542.1 1999-12-02
GBGB9928542.1A GB9928542D0 (en) 1999-12-02 1999-12-02 Pharmaceutical compounds

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10148601 A-371-Of-International 2000-12-01
US11/024,759 Continuation US7132419B2 (en) 1999-12-02 2004-12-30 Pharmaceutical compounds

Publications (1)

Publication Number Publication Date
WO2001046157A1 true WO2001046157A1 (fr) 2001-06-28

Family

ID=10865607

Family Applications (1)

Application Number Title Priority Date Filing Date
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

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)

Cited By (2)

* 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
CN103360329A (zh) * 2013-07-18 2013-10-23 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

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024096A2 (fr) * 1992-05-28 1993-12-09 Xenova Limited Utilisation de n-(2-(dimethylamino)ethyl) acridine-4-carboxamide et de ses analogues dans le traitement du cancer
WO1998012181A1 (fr) * 1996-09-23 1998-03-26 Rutgers, The State University Of New Jersey Composes heterocycliques de substitution s'utilisant comme agents anti-tumoraux
WO1998045272A1 (fr) * 1997-04-07 1998-10-15 Latrobe University Inhibiteurs de la topoisomerase

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5696131A (en) * 1993-01-22 1997-12-09 Xenova Limited Treatment of cancers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024096A2 (fr) * 1992-05-28 1993-12-09 Xenova Limited Utilisation de n-(2-(dimethylamino)ethyl) acridine-4-carboxamide et de ses analogues dans le traitement du cancer
WO1998012181A1 (fr) * 1996-09-23 1998-03-26 Rutgers, The State University Of New Jersey Composes heterocycliques de substitution s'utilisant comme agents anti-tumoraux
WO1998045272A1 (fr) * 1997-04-07 1998-10-15 Latrobe University Inhibiteurs de la topoisomerase

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
REWCASTLE G W ET AL: "POTENTIAL ANTITUMOR AGENTS. 51. SYNTHESIS AND ANITITUMOR ACITIVITY OF SUBSTITUTED PHENAZINE-1-CARBOXAMIDES", JOURNAL OF MEDICINAL CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 30, no. 5, 1987, pages 843 - 851, XP002051604, ISSN: 0022-2623 *

Cited By (3)

* 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
CN103360329A (zh) * 2013-07-18 2013-10-23 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
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

Also Published As

Publication number Publication date
GB9928542D0 (en) 2000-02-02
MY136029A (en) 2008-07-31
JP2003518103A (ja) 2003-06-03
MXPA02005476A (es) 2003-09-22
KR100767613B1 (ko) 2007-10-19
CN1433406A (zh) 2003-07-30
CN1304380C (zh) 2007-03-14
HUP0300392A2 (hu) 2003-07-28
AU1718401A (en) 2001-07-03
BR0016093A (pt) 2002-08-20
AU784397B2 (en) 2006-03-23
CA2392873A1 (fr) 2001-06-28
GB2373499A (en) 2002-09-25
HK1046133B (zh) 2005-04-15
ZA200204296B (en) 2003-05-29
HUP0300392A3 (en) 2003-09-29
PL356482A1 (en) 2004-06-28
HK1046133A1 (en) 2002-12-27
GB0215275D0 (en) 2002-08-14
TWI280242B (en) 2007-05-01
GB2373499B (en) 2004-11-17
EP1240148A1 (fr) 2002-09-18
KR20020070305A (ko) 2002-09-05

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