CA2963390C - Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives - Google Patents
Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives Download PDFInfo
- Publication number
- CA2963390C CA2963390C CA2963390A CA2963390A CA2963390C CA 2963390 C CA2963390 C CA 2963390C CA 2963390 A CA2963390 A CA 2963390A CA 2963390 A CA2963390 A CA 2963390A CA 2963390 C CA2963390 C CA 2963390C
- Authority
- CA
- Canada
- Prior art keywords
- methoxyphenyl
- cancer
- hydrogen
- hydroxyphenyl
- compound
- 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.)
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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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36476010P | 2010-07-15 | 2010-07-15 | |
| US61/364,760 | 2010-07-15 | ||
| CA2805590A CA2805590C (en) | 2010-07-15 | 2011-07-14 | Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2805590A Division CA2805590C (en) | 2010-07-15 | 2011-07-14 | Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2963390A1 CA2963390A1 (en) | 2012-01-19 |
| CA2963390C true CA2963390C (en) | 2020-02-11 |
Family
ID=44533096
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2963390A Active CA2963390C (en) | 2010-07-15 | 2011-07-14 | Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives |
| CA2805590A Active CA2805590C (en) | 2010-07-15 | 2011-07-14 | Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2805590A Active CA2805590C (en) | 2010-07-15 | 2011-07-14 | Synthesis and anticancer activity of aryl and heteroaryl-quinolin derivatives |
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)
| 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)
| 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 |
-
2011
- 2011-07-13 US US13/181,978 patent/US8524740B2/en active Active
- 2011-07-14 CA CA2963390A patent/CA2963390C/en active Active
- 2011-07-14 KR KR1020137003810A patent/KR20130043194A/ko not_active Ceased
- 2011-07-14 EP EP16181738.2A patent/EP3112348A1/en not_active Withdrawn
- 2011-07-14 RU RU2013105151/04A patent/RU2584688C2/ru active
- 2011-07-14 CA CA2805590A patent/CA2805590C/en active Active
- 2011-07-14 WO PCT/US2011/043985 patent/WO2012009519A1/en not_active Ceased
- 2011-07-14 JP JP2013519818A patent/JP2013532634A/ja active Pending
- 2011-07-14 CN CN201180033144.1A patent/CN103347859B/zh active Active
- 2011-07-14 EP EP11740761.9A patent/EP2593435B1/en active Active
- 2011-07-14 BR BR112013000716-8A patent/BR112013000716B1/pt active IP Right Grant
- 2011-07-14 KR KR1020177029236A patent/KR101913194B1/ko active Active
- 2011-07-14 AU AU2011279118A patent/AU2011279118B2/en active Active
- 2011-07-15 TW TW100125130A patent/TWI499417B/zh active
-
2015
- 2015-08-07 JP JP2015157760A patent/JP6371741B2/ja active Active
-
2017
- 2017-05-24 JP JP2017102672A patent/JP6457584B2/ja active Active
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 |
| 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 |
| 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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