WO1994002145A3 - 2-aryl-4-quinolones utilisees comme composes antitumoraux - Google Patents

2-aryl-4-quinolones utilisees comme composes antitumoraux Download PDF

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Publication number
WO1994002145A3
WO1994002145A3 PCT/US1993/006893 US9306893W WO9402145A3 WO 1994002145 A3 WO1994002145 A3 WO 1994002145A3 US 9306893 W US9306893 W US 9306893W WO 9402145 A3 WO9402145 A3 WO 9402145A3
Authority
WO
WIPO (PCT)
Prior art keywords
aryl
quinolones
antitumor compounds
disclosed
cell growth
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.)
Ceased
Application number
PCT/US1993/006893
Other languages
English (en)
Other versions
WO1994002145A2 (fr
Inventor
Kuo-Hsiung Lee
Sheng-Chu Kuo
Tian-Shung Wu
Su-Ying Liu
Kou M Hwang
Hui Kang Weng
Le Peng Li
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.)
University of North Carolina at Chapel Hill
Genelabs Technologies Inc
Original Assignee
University of North Carolina at Chapel Hill
Genelabs Technologies Inc
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 University of North Carolina at Chapel Hill, Genelabs Technologies Inc filed Critical University of North Carolina at Chapel Hill
Priority to AU47807/93A priority Critical patent/AU4780793A/en
Publication of WO1994002145A2 publication Critical patent/WO1994002145A2/fr
Publication of WO1994002145A3 publication Critical patent/WO1994002145A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention se rapporte à un procédé pour inhiber la croissance de cellules tumorales, qui consiste à administrer une quantité pharmaceutiquement efficace d'un composé de 2-aryl-4-quinolone. Ce composé de 2-aryl-4-quinolone a pour effet d'inhiber la croissance des cellules tumorales dans des tumeurs dans lesquelles on rencontre des résistances multiples aux médicaments. L'invention décrit également de nouveaux composés antitumoraux à base de 2-aryl-4-quinolone.
PCT/US1993/006893 1992-07-22 1993-07-22 2-aryl-4-quinolones utilisees comme composes antitumoraux Ceased WO1994002145A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU47807/93A AU4780793A (en) 1992-07-22 1993-07-22 2-aryl-4-quinolones as antitumor compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US91882492A 1992-07-22 1992-07-22
US918,824 1992-07-22

Publications (2)

Publication Number Publication Date
WO1994002145A2 WO1994002145A2 (fr) 1994-02-03
WO1994002145A3 true WO1994002145A3 (fr) 1994-04-28

Family

ID=25441020

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/006893 Ceased WO1994002145A2 (fr) 1992-07-22 1993-07-22 2-aryl-4-quinolones utilisees comme composes antitumoraux

Country Status (2)

Country Link
AU (1) AU4780793A (fr)
WO (1) WO1994002145A2 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100236852B1 (ko) * 1992-10-09 2000-03-02 나가야마 오사무 플루오로 퀴놀린 유도체
US5571822A (en) * 1994-09-30 1996-11-05 The University Of North Carolina At Chapel Hill Antitumor compounds
KR19990069876A (ko) * 1998-02-13 1999-09-06 성재갑 4-퀴놀론 구조를 갖는 사이클린-의존 키나아제 저해제 화합물
FR2781218B1 (fr) 1998-07-15 2001-09-07 Lafon Labor Compositions pharmaceutiques comprenant des 2-quinolones
FR2797444B1 (fr) * 1999-08-13 2003-02-07 Lafon Labor Compositions pharmaceutiques comprenant des 4-quinolones
AU2001273639A1 (en) * 2000-06-26 2002-01-08 Neurogen Corporation Aryl fused substituted 4-oxy-pyridines
FR2813791B1 (fr) 2000-09-14 2004-03-12 Lafon Labor Utilisation de 2- et 4-quinolones pour inhiber la neo-proliferation intimale
CZ300589B6 (cs) 2006-09-04 2009-06-24 Univerzita Palackého Deriváty 2-fenyl-3-hydroxychinolin-4(1H)-onu a zpusob jejich prípravy a použití
EP2468747B1 (fr) * 2006-12-07 2014-09-03 China Medical University 2-Sélénophène-4-quinolones en tant qu'agents anticancéreux
EP2291355A4 (fr) * 2008-01-04 2011-08-03 Panjab University Nouvelles tétrahydroquinoléines en tant qu'inhibiteurs d'aromatase
US8524740B2 (en) 2010-07-15 2013-09-03 Tairx, Inc. Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives
CN102675200B (zh) * 2012-05-16 2014-04-09 中国药科大学 一类具有抗肿瘤活性的2-苯基-4-喹诺酮化合物、其制备方法及用途
SMT202500447T1 (it) 2021-11-02 2026-01-12 Flare Therapeutics Inc Agonisti inversi di pparg e loro usi

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725413A (en) * 1972-01-17 1973-04-03 Warner Lambert Co Process for the production of ethyl 8-hydroxy-1,3-dioxolo{8 4,5g{9 -quinoline-7-carboxylate
FR2276049A1 (fr) * 1974-06-25 1976-01-23 Chinoin Gyogyszer Es Vegyeszet Procede de preparation de nouveaux derives d'acides quinoleine-carboxyliques substitues en position 5 a action bacteriostatique
JPS567784A (en) * 1979-06-28 1981-01-27 Yoshitomi Pharmaceut Ind Ltd Imidazoquinolone derivative
EP0341104A2 (fr) * 1988-04-06 1989-11-08 MERCK PATENT GmbH Composés flavonoides substitués, leurs sels, procédé de leur préparation et compositions pharmaceutiques les contenant
EP0343574A1 (fr) * 1988-05-24 1989-11-29 Kirin Beer Kabushiki Kaisha Dérivés de la 4(1H)-quinoléione
US5126351A (en) * 1991-01-24 1992-06-30 Glaxo Inc. Antitumor compounds

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725413A (en) * 1972-01-17 1973-04-03 Warner Lambert Co Process for the production of ethyl 8-hydroxy-1,3-dioxolo{8 4,5g{9 -quinoline-7-carboxylate
FR2276049A1 (fr) * 1974-06-25 1976-01-23 Chinoin Gyogyszer Es Vegyeszet Procede de preparation de nouveaux derives d'acides quinoleine-carboxyliques substitues en position 5 a action bacteriostatique
JPS567784A (en) * 1979-06-28 1981-01-27 Yoshitomi Pharmaceut Ind Ltd Imidazoquinolone derivative
EP0341104A2 (fr) * 1988-04-06 1989-11-08 MERCK PATENT GmbH Composés flavonoides substitués, leurs sels, procédé de leur préparation et compositions pharmaceutiques les contenant
EP0343574A1 (fr) * 1988-05-24 1989-11-29 Kirin Beer Kabushiki Kaisha Dérivés de la 4(1H)-quinoléione
US5126351A (en) * 1991-01-24 1992-06-30 Glaxo Inc. Antitumor compounds

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
A. KASAHARA ET AL.: "A new synthesis of 2-aryl-4-quinolones", CHEM. IND., no. 4, 1981, pages 121 *
BANG-CHI CHEN: "A versatile synthesis of 2-alkyl and 2-aryl 4-quinolones", SYNTHESIS, vol. 5, 1987, pages 482 - 483 *
DATABASE WPI Week 8112, Derwent World Patents Index; AN 81-20215D *
J.B. JIANG ET AL.: "Synthesis and biological evaluation of 2-styrylquinazolin-4(3h)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization", J. MED. CHEM., vol. 33, 1990, pages 1721 - 1728 *
K. SHENG-CHU: "Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-quinolones and related compounds: Identification as antimitotic agents interacting with tubulin", J. MED. CHEM., vol. 36, no. 9, 30 April 1993 (1993-04-30), pages 1146 - 1156 *
P. VENTURELLA ET AL.: "On the reactions between ethyl benzoylacetate and anisidines", J. HETEROCYCL. CHEM., vol. 12, no. 4, 1975, pages 669 - 673 *
P. VENTURELLA ET AL.: "Synthesis of 1-methyl-2-phenyl-5-hydroxy-4-quinolone and improved synthesis of edulein", GAZZ. CHIM. ITAL., vol. 100, no. 7, 1970, pages 678 - 681 *
V.N. KALININ ET AL.: "A new route to 2-aryl-4-quinolones via palladium-catalyzed carbonylative coupling of o-iodoanilines with terminal arylacetylenes", TETRAHEDRON LETTERS, vol. 33, no. 3, 14 January 1992 (1992-01-14), pages 373 - 376 *

Also Published As

Publication number Publication date
WO1994002145A2 (fr) 1994-02-03
AU4780793A (en) 1994-02-14

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