AU2011279118B2 - Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives - Google Patents

Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives Download PDF

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Publication number
AU2011279118B2
AU2011279118B2 AU2011279118A AU2011279118A AU2011279118B2 AU 2011279118 B2 AU2011279118 B2 AU 2011279118B2 AU 2011279118 A AU2011279118 A AU 2011279118A AU 2011279118 A AU2011279118 A AU 2011279118A AU 2011279118 B2 AU2011279118 B2 AU 2011279118B2
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hydrogen
methoxyphenyl
fluorophenyl
compound
hydroxyphenyl
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AU2011279118A1 (en
Inventor
Li-Chen Chou
Jing-Gung Chung
Chi-Hung Huang
Li-Jiau Huang
Sheng-Chu Kuo
Kuo-Hsiung Lee
Meng-Tung Tsai
Tzong-Der Way
Tian-Shung Wu
Jai-Sing Yang
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Tairx Inc
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Tairx Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4741—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having oxygen as a ring hetero atom, e.g. tubocuraran derivatives, noscapine, bicuculline
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • C07D215/38—Nitrogen atoms
    • 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
    • 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
    • C07D403/04—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 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
AU2011279118A 2010-07-15 2011-07-14 Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives Active AU2011279118B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US36476010P 2010-07-15 2010-07-15
US61/364,760 2010-07-15
PCT/US2011/043985 WO2012009519A1 (en) 2010-07-15 2011-07-14 Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives

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AU2011279118A1 AU2011279118A1 (en) 2012-12-20
AU2011279118B2 true AU2011279118B2 (en) 2014-12-18

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US (1) US8524740B2 (enExample)
EP (2) EP3112348A1 (enExample)
JP (3) JP2013532634A (enExample)
KR (2) KR20130043194A (enExample)
CN (1) CN103347859B (enExample)
AU (1) AU2011279118B2 (enExample)
BR (1) BR112013000716B1 (enExample)
CA (2) CA2963390C (enExample)
RU (1) RU2584688C2 (enExample)
TW (1) TWI499417B (enExample)
WO (1) WO2012009519A1 (enExample)

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US20150370707A1 (en) * 2014-06-24 2015-12-24 Qualcomm Incorporated Disunited shared-information and private-information caches
EP3302488B1 (en) * 2015-06-03 2020-09-30 Tairx, Inc. Novel use of aryl-quinolin derivatives as inhibitors of vasculogenic mimicry
CN108911967A (zh) * 2018-08-03 2018-11-30 上海华堇生物技术有限责任公司 2,5–二甲氧基苯甲酰氯的制备方法
CN112358462B (zh) * 2020-11-10 2023-11-10 成都伊诺达博医药科技有限公司 一种胡椒环衍生物的合成方法
SMT202500447T1 (it) 2021-11-02 2026-01-12 Flare Therapeutics Inc Agonisti inversi di pparg e loro usi
JP2025513455A (ja) 2022-04-22 2025-04-24 バーテックス ファーマシューティカルズ インコーポレイテッド 疼痛の治療のためのヘテロアリール化合物
CN116789567B (zh) * 2023-05-18 2026-03-27 福建凯昕药业有限公司 抗血小板减少症药芦曲泊帕中间体及其制备方法
US20250367314A1 (en) * 2024-05-31 2025-12-04 Du-Shieng Chien Linker-payload, an antibody-drug conjugate made thereby and uses thereof
CN120695016B (zh) * 2025-08-29 2025-12-02 北京大学 一种二氢喹啉衍生物在制备预防或治疗脂肪肝产品中的用途

Citations (1)

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Publication number Priority date Publication date Assignee Title
WO2008070176A1 (en) * 2006-12-07 2008-06-12 China Medical University Novel hydrophilic derivatives of 2-aryl-4-quinolones as anticancer agents

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WO1994002145A2 (en) 1992-07-22 1994-02-03 Genelabs Technologies, Inc. 2-aryl-4-quinolones as antitumor compounds
JPH0733743A (ja) * 1993-07-22 1995-02-03 Kyorin Pharmaceut Co Ltd ２−アリール−４−キノリノール誘導体
US5571822A (en) * 1994-09-30 1996-11-05 The University Of North Carolina At Chapel Hill Antitumor compounds
US6569870B1 (en) * 2000-09-25 2003-05-27 The University Of North Carolina At Chapel Hill Fluorinated quinolones as antimitotic and antitumor agents
SE0103648D0 (sv) * 2001-11-01 2001-11-01 Astrazeneca Ab Therapeutic quinolone compounds
US6916831B2 (en) * 2003-02-24 2005-07-12 The University Of North Carolina At Chapel Hill Flavone acetic acid analogs and methods of use thereof
US6897316B2 (en) * 2003-08-08 2005-05-24 China Medical University Substituted 2-phenyl-4-quinolone-3-carboxylic acid compounds and their use as antitumor agents
AU2008345225A1 (en) * 2007-12-21 2009-07-09 University Of Rochester Method for altering the lifespan of eukaryotic organisms

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008070176A1 (en) * 2006-12-07 2008-06-12 China Medical University Novel hydrophilic derivatives of 2-aryl-4-quinolones as anticancer agents

Also Published As

Publication number Publication date
JP2017206511A (ja) 2017-11-24
EP2593435A1 (en) 2013-05-22
US20120015908A1 (en) 2012-01-19
AU2011279118A1 (en) 2012-12-20
CA2963390C (en) 2020-02-11
CA2805590A1 (en) 2012-01-19
JP2013532634A (ja) 2013-08-19
CN103347859A (zh) 2013-10-09
KR20130043194A (ko) 2013-04-29
WO2012009519A1 (en) 2012-01-19
EP2593435B1 (en) 2016-09-07
EP3112348A1 (en) 2017-01-04
BR112013000716A2 (pt) 2019-10-01
TW201206439A (en) 2012-02-16
US8524740B2 (en) 2013-09-03
CN103347859B (zh) 2015-12-02
JP2016028032A (ja) 2016-02-25
KR101913194B1 (ko) 2018-10-31
CA2805590C (en) 2017-05-16
CA2963390A1 (en) 2012-01-19
TWI499417B (zh) 2015-09-11
RU2584688C2 (ru) 2016-05-20
KR20170118244A (ko) 2017-10-24
RU2013105151A (ru) 2014-08-20
JP6457584B2 (ja) 2019-01-23
JP6371741B2 (ja) 2018-08-08
BR112013000716B1 (pt) 2021-10-05

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