CN103347859B - 芳基及杂芳基喹啉衍生物之合成及抗癌活性 - Google Patents

芳基及杂芳基喹啉衍生物之合成及抗癌活性 Download PDF

Info

Publication number
CN103347859B
CN103347859B CN201180033144.1A CN201180033144A CN103347859B CN 103347859 B CN103347859 B CN 103347859B CN 201180033144 A CN201180033144 A CN 201180033144A CN 103347859 B CN103347859 B CN 103347859B
Authority
CN
China
Prior art keywords
fluorophenyl
compound
hydrogen
hydroxyl
nmr
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.)
Active
Application number
CN201180033144.1A
Other languages
English (en)
Chinese (zh)
Other versions
CN103347859A (zh
Inventor
郭盛助
李国雄
黃丽娇
周立琛
吴天赏
魏宗德
钟景光
杨家欣
黃济鸿
蔡孟东
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.)
Efficient Pharma Management Corp
Original Assignee
Efficient Pharma Management Corp
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 Efficient Pharma Management Corp filed Critical Efficient Pharma Management Corp
Publication of CN103347859A publication Critical patent/CN103347859A/zh
Application granted granted Critical
Publication of CN103347859B publication Critical patent/CN103347859B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

Landscapes

  • 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)
CN201180033144.1A 2010-07-15 2011-07-14 芳基及杂芳基喹啉衍生物之合成及抗癌活性 Active CN103347859B (zh)

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

Publications (2)

Publication Number Publication Date
CN103347859A CN103347859A (zh) 2013-10-09
CN103347859B true CN103347859B (zh) 2015-12-02

Family

ID=44533096

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201180033144.1A Active CN103347859B (zh) 2010-07-15 2011-07-14 芳基及杂芳基喹啉衍生物之合成及抗癌活性

Country Status (11)

Country Link
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)

Families Citing this family (9)

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

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP2468747B1 (en) * 2006-12-07 2014-09-03 China Medical University 2-Selenophene-4-quinolones as anticancer agents
AU2008345225A1 (en) * 2007-12-21 2009-07-09 University Of Rochester Method for altering the lifespan of eukaryotic organisms

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
AU2011279118B2 (en) 2014-12-18
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
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

Similar Documents

Publication Publication Date Title
JP6457584B2 (ja) アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性
CN107530556B (zh) Dna烷化剂
PT2010496E (pt) 4-anilinoquinolina-3-carboxamidas como inibidores de csf-1r cinase
ES2594252T3 (es) Compuesto de quinolona y composición farmacéutica
JP2016516696A (ja) ヘモグロビンの修飾のための化合物及びその使用
FR3008978A1 (fr) "nouveaux derives d'indole et de pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent"
JP2024528251A (ja) Ｈｄａｃとｎａｄ合成を標的とする多標的阻害剤及びその用途
JP2024073414A (ja) ゲムシタビン誘導体の新規小分子薬物コンジュゲート
JP7423655B2 (ja) キノリル含有化合物、医薬組成物およびその使用
JPH05271214A (ja) ベンゾフラニル−およびチオフエニルメチルチオ−アルカンカルボン酸誘導体
WO2005080392A1 (ja) ピラゾロキノロン誘導体およびその用途
EP1541149A1 (en) Phosphodiesterase inhibitor
JP2024054873A (ja) ゲムシタビンモノホスフェートの小分子薬物コンジュゲート
KR101071359B1 (ko) 항암 활성을 가지는 2-메틸-2-알킬-6-아미도-2ｈ-벤조피란 유도체
CN1294120C (zh) 吡咯烷类基质金属蛋白酶抑制剂及其应用
WO2025240834A1 (en) Nsd2-targeted chemical degraders and compositions and methods of use thereof
CA2886744C (en) Imatinib derivatives, their preparation and use to treat cancer and bacterial and viral infections
JP2011016754A (ja) 置換フェナントレン化合物を有効成分とするがんを予防および／または治療するための医薬組成物
DE10043791A1 (de) Arzneimittel gegen virale Erkrankungen
WO2014179401A1 (en) 2-arylnaphthyridin-4-ones as potent antitumor agents targeting tumorigenic cell lines

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant