KR101913194B1 - 아릴 및 헤테로아릴-퀴놀린 유도체의 합성 및 이의 항암 효과 - Google Patents

아릴 및 헤테로아릴-퀴놀린 유도체의 합성 및 이의 항암 효과 Download PDF

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KR101913194B1
KR101913194B1 KR1020177029236A KR20177029236A KR101913194B1 KR 101913194 B1 KR101913194 B1 KR 101913194B1 KR 1020177029236 A KR1020177029236 A KR 1020177029236A KR 20177029236 A KR20177029236 A KR 20177029236A KR 101913194 B1 KR101913194 B1 KR 101913194B1
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compound
cancer
nmr
mhz
mmol
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KR20170118244A (ko
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셍-츄 궈
궈-슝 이
리-지유 황
리-첸 츄
티엔-숭 우
종-더 웨이
징-궁 청
재-추 양
치-훙 황
멩-퉁 자이
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타이알엑스, 아이엔씨.
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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
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    • 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
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    • 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
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    • 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
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    • 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)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (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)
KR1020177029236A 2010-07-15 2011-07-14 아릴 및 헤테로아릴-퀴놀린 유도체의 합성 및 이의 항암 효과 Active KR101913194B1 (ko)

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

Related Parent Applications (1)

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KR1020137003810A Division KR20130043194A (ko) 2010-07-15 2011-07-14 아릴 및 헤테로아릴-퀴놀린 유도체의 합성 및 이의 항암 효과

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KR20170118244A KR20170118244A (ko) 2017-10-24
KR101913194B1 true KR101913194B1 (ko) 2018-10-31

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KR1020177029236A Active KR101913194B1 (ko) 2010-07-15 2011-07-14 아릴 및 헤테로아릴-퀴놀린 유도체의 합성 및 이의 항암 효과
KR1020137003810A Ceased KR20130043194A (ko) 2010-07-15 2011-07-14 아릴 및 헤테로아릴-퀴놀린 유도체의 합성 및 이의 항암 효과

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US (1) US8524740B2 (https=)
EP (2) EP2593435B1 (https=)
JP (3) JP2013532634A (https=)
KR (2) KR101913194B1 (https=)
CN (1) CN103347859B (https=)
AU (1) AU2011279118B2 (https=)
BR (1) BR112013000716B1 (https=)
CA (2) CA2963390C (https=)
RU (1) RU2584688C2 (https=)
TW (1) TWI499417B (https=)
WO (1) WO2012009519A1 (https=)

Families Citing this family (9)

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US20150370707A1 (en) * 2014-06-24 2015-12-24 Qualcomm Incorporated Disunited shared-information and private-information caches
CA2983769C (en) * 2015-06-03 2020-09-22 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
PT4426434T (pt) 2021-11-02 2025-11-24 Flare Therapeutics Inc Agonistas inversos de pparg e suas utilizações
WO2023205463A1 (en) 2022-04-22 2023-10-26 Vertex Pharmaceuticals Incorporated Heteroaryl compounds for the treatment of pain
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)

* 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

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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
WO2009086303A2 (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

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JP2017206511A (ja) 2017-11-24
EP3112348A1 (en) 2017-01-04
KR20170118244A (ko) 2017-10-24
JP2013532634A (ja) 2013-08-19
CA2963390A1 (en) 2012-01-19
JP2016028032A (ja) 2016-02-25
JP6457584B2 (ja) 2019-01-23
BR112013000716B1 (pt) 2021-10-05
TWI499417B (zh) 2015-09-11
AU2011279118A1 (en) 2012-12-20
CA2805590C (en) 2017-05-16
US20120015908A1 (en) 2012-01-19
AU2011279118B2 (en) 2014-12-18
TW201206439A (en) 2012-02-16
RU2584688C2 (ru) 2016-05-20
EP2593435A1 (en) 2013-05-22
KR20130043194A (ko) 2013-04-29
CN103347859B (zh) 2015-12-02
CA2805590A1 (en) 2012-01-19
EP2593435B1 (en) 2016-09-07
CA2963390C (en) 2020-02-11
WO2012009519A1 (en) 2012-01-19
US8524740B2 (en) 2013-09-03
CN103347859A (zh) 2013-10-09
RU2013105151A (ru) 2014-08-20
JP6371741B2 (ja) 2018-08-08
BR112013000716A2 (pt) 2019-10-01

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