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WO2015160489A3 - Substituted cyclopenta pyrimidine bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof - Google Patents

Substituted cyclopenta pyrimidine bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof Download PDF

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Publication number
WO2015160489A3
WO2015160489A3 PCT/US2015/022871 US2015022871W WO2015160489A3 WO 2015160489 A3 WO2015160489 A3 WO 2015160489A3 US 2015022871 W US2015022871 W US 2015022871W WO 2015160489 A3 WO2015160489 A3 WO 2015160489A3
Authority
WO
WIPO (PCT)
Prior art keywords
methods
antimitotic
antitumor activity
bicyclic compounds
substituted cyclopenta
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/US2015/022871
Other languages
French (fr)
Other versions
WO2015160489A2 (en
Inventor
Aleem Gangjee
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.)
Duquesne University of the Holy Spirit
Original Assignee
Duquesne University of the Holy Spirit
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
Priority claimed from US14/244,445 external-priority patent/US9624178B2/en
Application filed by Duquesne University of the Holy Spirit filed Critical Duquesne University of the Holy Spirit
Priority to EP15779898.4A priority Critical patent/EP3125897A4/en
Priority to JP2016559903A priority patent/JP6532887B2/en
Priority to CA2944450A priority patent/CA2944450C/en
Publication of WO2015160489A2 publication Critical patent/WO2015160489A2/en
Publication of WO2015160489A3 publication Critical patent/WO2015160489A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention provides substituted cyclopenta and cyclopentyl pyrimidine bicyclic compounds of Formula III, and 5,6 - saturated and unsaturated and pharmaceutically acceptable salts, prodrugs, solvates, and hydrates thereof, having antimitotic activity, anti-multidrug resistance activity, such as for example P-glycoprotein inhibition, and antitumor activity, and which inhibit paclitaxel sensitive and resistant tumor cells. Also provided are methods of utilizing these compounds for treating tumor cells and inhibiting mitosis of cancerous cells.
PCT/US2015/022871 2014-04-03 2015-03-27 Substituted cyclopenta pyrimidine bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof Ceased WO2015160489A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP15779898.4A EP3125897A4 (en) 2014-04-03 2015-03-27 Substituted cyclopenta pyrimidine bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof
JP2016559903A JP6532887B2 (en) 2014-04-03 2015-03-27 Substituted cyclopentapyrimidine bicyclic compounds having antimitotic and / or antitumor activity and methods of use thereof
CA2944450A CA2944450C (en) 2014-04-03 2015-03-27 Substituted cyclopenta pyrimidine bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14/244,445 US9624178B2 (en) 2008-07-10 2014-04-03 Substituted cyclopenta pyrimidine bicyclic compounds having antitmitotic and/or antitumor activity methods of use thereof
US14/244,445 2014-04-03

Publications (2)

Publication Number Publication Date
WO2015160489A2 WO2015160489A2 (en) 2015-10-22
WO2015160489A3 true WO2015160489A3 (en) 2016-03-31

Family

ID=54324696

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2015/022871 Ceased WO2015160489A2 (en) 2014-04-03 2015-03-27 Substituted cyclopenta pyrimidine bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof

Country Status (4)

Country Link
EP (1) EP3125897A4 (en)
JP (1) JP6532887B2 (en)
CA (1) CA2944450C (en)
WO (1) WO2015160489A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100010016A1 (en) * 2008-07-10 2010-01-14 Aleem Gangjee Bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof
US20110160203A1 (en) * 2009-12-30 2011-06-30 Arqule, Inc. Substituted Pyrrolo-Aminopyrimidine Compounds
US20130029942A1 (en) * 2003-07-03 2013-01-31 Myrexis, Inc. Compounds and therapeutical uses thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57203072A (en) * 1981-06-05 1982-12-13 Sankyo Co Ltd 4-anilinopyrimidine derivative, its preparation, antidepressant comprising it as active ingredient
WO2012106522A2 (en) * 2011-02-04 2012-08-09 Duquesne University Of The Holy Spirit Bicyclic and tricyclic pyrimidine tyrosine kinase inhibitors with antitubulin activity and methods of treating a patient

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130029942A1 (en) * 2003-07-03 2013-01-31 Myrexis, Inc. Compounds and therapeutical uses thereof
US20100010016A1 (en) * 2008-07-10 2010-01-14 Aleem Gangjee Bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof
US20140303188A1 (en) * 2008-07-10 2014-10-09 Duquesne University Of The Holy Spirit Substituted Cyclopenta Pyrimidine Bicyclic Compounds Having Antitmitotic And/Or Antitumor Activity And Methods Of Use Thereof
US20110160203A1 (en) * 2009-12-30 2011-06-30 Arqule, Inc. Substituted Pyrrolo-Aminopyrimidine Compounds

Also Published As

Publication number Publication date
WO2015160489A2 (en) 2015-10-22
EP3125897A4 (en) 2017-11-15
EP3125897A2 (en) 2017-02-08
JP2017512805A (en) 2017-05-25
CA2944450C (en) 2023-03-21
JP6532887B2 (en) 2019-06-19
CA2944450A1 (en) 2015-10-22

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