CA2859985C - Anti-cancer compounds targeting ral gtpases and methods of using the same - Google Patents

Anti-cancer compounds targeting ral gtpases and methods of using the same Download PDF

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Publication number
CA2859985C
CA2859985C CA2859985A CA2859985A CA2859985C CA 2859985 C CA2859985 C CA 2859985C CA 2859985 A CA2859985 A CA 2859985A CA 2859985 A CA2859985 A CA 2859985A CA 2859985 C CA2859985 C CA 2859985C
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mmol
equ
aryl
ethanol
ral
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French (fr)
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CA2859985A1 (en
Inventor
Dan Theodorescu
Michael Fitzpatrick Wempe
David Ross
Samy MEROUEH
Martin A. Schwartz
Phillip REIGAN
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University of Colorado Boulder
UVA Licensing and Ventures Group
Indiana University Research and Technology Corp
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University of Colorado Boulder
Indiana University Research and Technology Corp
University of Virginia Patent Foundation
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4151,2-Diazoles
    • A61K31/41621,2-Diazoles condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41641,3-Diazoles
    • A61K31/41881,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/4353Heterocyclic 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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437Heterocyclic 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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/4738Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4745Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/55131,4-Benzodiazepines, e.g. diazepam or clozapine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic agents specific for metastasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/04Immunostimulants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic 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
    • C07D491/02Heterocyclic 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
    • C07D491/04Ortho-condensed systems
    • C07D491/044Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2859985A 2011-12-21 2012-12-21 Anti-cancer compounds targeting ral gtpases and methods of using the same Active CA2859985C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161578869P 2011-12-21 2011-12-21
US61/578,869 2011-12-21
PCT/US2012/071341 WO2013096820A1 (en) 2011-12-21 2012-12-21 Anti-cancer compounds targeting ral gtpases and methods of using the same

Publications (2)

Publication Number Publication Date
CA2859985A1 CA2859985A1 (en) 2013-06-27
CA2859985C true CA2859985C (en) 2020-11-03

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CA2859985A Active CA2859985C (en) 2011-12-21 2012-12-21 Anti-cancer compounds targeting ral gtpases and methods of using the same

Country Status (8)

Country Link
US (3) US9353121B2 (https=)
EP (1) EP2793881B1 (https=)
JP (1) JP6473330B2 (https=)
KR (1) KR102097343B1 (https=)
CN (1) CN104271132B (https=)
AU (1) AU2012358317B2 (https=)
CA (1) CA2859985C (https=)
WO (1) WO2013096820A1 (https=)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2859985C (en) 2011-12-21 2020-11-03 The Regents Of The University Of Colorado Anti-cancer compounds targeting ral gtpases and methods of using the same
US10202397B2 (en) * 2014-07-10 2019-02-12 The Regents Of The University Of Colorado, A Body Corporate Anti-cancer compounds targeting Ral GTPases and methods of using the same
ES2768694T3 (es) 2014-09-19 2020-06-23 Forma Therapeutics Inc Composiciones de quinolinona pirimidinas como inhibidores de isocitrato dehidrogenasa mutante
WO2016044789A1 (en) 2014-09-19 2016-03-24 Forma Therapeutics, Inc. Pyridin-2(1h)-one quinolinone derivatives as mutant-isocitrate dehydrogenase inhibitors
WO2016049500A1 (en) 2014-09-25 2016-03-31 Duke University Kinase inhibitors and related methods of use
WO2016145252A1 (en) * 2015-03-10 2016-09-15 The Trustees Of Princeton University Shmt inhibitors
US20180170942A1 (en) * 2015-06-16 2018-06-21 Nantbio, Inc. Polycyclic derivatives targeting ral gtpases and their therapeutical applications
MX385384B (es) 2016-06-22 2025-03-18 Univ Vanderbilt Moduladores alostericos positivos del receptor muscarinico de acetilcolina m4
US10077273B2 (en) 2016-09-14 2018-09-18 The Trustees Of Princeton University SHMT inhibitors
WO2018080216A1 (en) * 2016-10-28 2018-05-03 Daewoong Pharmaceutical Co., Ltd. Phenyl phthalazine derivative, method for the preparation thereof, and pharmaceutical composition comprising the same
US10961253B2 (en) 2016-11-07 2021-03-30 Vanderbilt University Positive allosteric modulators of the muscarinic acetylcholine receptor M4
WO2018085813A1 (en) 2016-11-07 2018-05-11 Vanderbilt University Positive allosteric modulators of the muscarinic acetylcholine receptor m4
WO2018085803A1 (en) 2016-11-07 2018-05-11 Vanderbilt University Positive allosteric modulators of the muscarinic acetylcholine receptor m4
CN110024421B (zh) 2016-11-23 2020-12-25 瑞典爱立信有限公司 用于自适应控制去相关滤波器的方法和装置
TW201930311A (zh) 2017-12-05 2019-08-01 泛德比爾特大學 蕈毒鹼型乙醯膽鹼受體m4之正向別構調節劑
JP2021505581A (ja) 2017-12-05 2021-02-18 ヴァンダービルト ユニヴァーシティ ムスカリン性アセチルコリンレセプターm4のポジティブアロステリック調節因子
WO2019142192A1 (en) 2018-01-17 2019-07-25 Gavish-Galilee Bio Applications Ltd. New methionine metabolic pathway inhibitors
BR112020014561A2 (pt) * 2018-01-17 2020-12-08 Migal - Galilee Research Institute Ltd. Nibidores inovadores da via metabólica da metionina
WO2019222553A1 (en) 2018-05-16 2019-11-21 Forma Therapeutics, Inc. Inhibiting mutant idh-1
US10532047B2 (en) 2018-05-16 2020-01-14 Forma Therapeutics, Inc. Solid forms of ((S)-5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile
US11013734B2 (en) 2018-05-16 2021-05-25 Forma Therapeutics, Inc. Treating patients harboring an isocitrate dehydrogenase-1 (IDH-1) mutation
US11311527B2 (en) 2018-05-16 2022-04-26 Forma Therapeutics, Inc. Inhibiting mutant isocitrate dehydrogenase 1 (mIDH-1)
US11013733B2 (en) 2018-05-16 2021-05-25 Forma Therapeutics, Inc. Inhibiting mutant isocitrate dehydrogenase 1 (mlDH-1)
CN109305972B (zh) * 2018-09-27 2021-07-09 广州医科大学 一种二氢吡喃并吡唑类化合物及其制备方法和应用
CN109734676B (zh) * 2019-01-16 2021-01-29 四川大学 苯并二氮杂卓类衍生物及其制备方法和应用
EP4076416A4 (en) * 2019-12-19 2024-04-10 The Trustees of Indiana University Small-molecule covalent inhibition of ral gtpases
CN111406752B (zh) * 2020-04-23 2021-07-23 中国农业科学院植物保护研究所 二氢吡咯并吡唑酮类衍生物作为几丁质酶抑制剂或杀线虫剂的应用
WO2022040005A1 (en) * 2020-08-17 2022-02-24 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Profilin1:actin inhibitor an anti-angiogenic compound
BR112023009420A2 (pt) * 2020-11-18 2023-10-03 Univ Texas Tech System Terapias para o câncer usando moléculas pequenas que se ligam e inibem proteínas de interação ral
US20240325374A1 (en) * 2021-07-23 2024-10-03 The Research Institute At Nationwide Children's Hospital Inhibiting intracellular pathogens
US20250134888A1 (en) * 2022-02-07 2025-05-01 Cornell University Inhibitors of malic enzyme 1
CN120168481B (zh) * 2025-05-14 2025-08-19 天津医科大学 一种抑制REXO4消解R-loop酶活性的小分子及其在制备肿瘤药物中的应用

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US361185A (en) * 1887-04-12 Poueths to john h
US362503A (en) * 1887-05-10 Sectional boat
US4555396A (en) 1982-12-22 1985-11-26 Eastman Kodak Company Use of pyrylium and thiapyrylium compounds as biological stains
US5750550A (en) * 1995-09-15 1998-05-12 Sanofi 2-(pyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3 (2H)-One 1, 1-dioxides and compositions and method of use thereof
JPH10279480A (ja) * 1997-04-07 1998-10-20 Mitsubishi Chem Corp 皮膚組織障害の予防・治療剤
US6143471A (en) * 1998-03-10 2000-11-07 Mitsubishi Paper Mills Limited Positive type photosensitive composition
AU1853600A (en) 1999-01-06 2000-07-24 Choong-Chin Liew Method for the detection of gene transcripts in blood and uses thereof
US20070105105A1 (en) 2003-05-23 2007-05-10 Mount Sinai School Of Medicine Of New York University Surrogate cell gene expression signatures for evaluating the physical state of a subject
CA2533803A1 (en) 2003-07-29 2005-02-10 Bristol-Myers Squibb Company Biomarkers of cyclin-dependent kinase modulation
KR20080015123A (ko) * 2005-05-25 2008-02-18 다나베 미츠비시 세이야꾸 가부시키가이샤 피라졸론 유도체를 포함하는 의약
WO2007016539A2 (en) * 2005-07-29 2007-02-08 Children's Hospital Medical Center Gtpase inhibitors and methods of use and crystal structure of rac-1 gtpase
AU2006286441A1 (en) * 2005-09-02 2007-03-08 Janssen R&D Ireland Benzodiazepines as HCV inhibitors
US20090221568A1 (en) 2005-11-04 2009-09-03 Jared Shaw Synthesis of Inhibitors of FtsZ
WO2007081966A2 (en) 2006-01-09 2007-07-19 University Of Southern California Small molecules for treating cancer and abnormal cell proliferation disorders
WO2008143894A2 (en) * 2007-05-14 2008-11-27 Dana-Farber Cancer Institute, Inc. Phosphorylated rala
CA2709784A1 (en) * 2007-12-21 2009-07-09 University Of Rochester Method for altering the lifespan of eukaryotic organisms
WO2011010715A1 (ja) 2009-07-24 2011-01-27 国立大学法人 東京大学 Pr-Set7阻害剤
WO2011035143A2 (en) 2009-09-17 2011-03-24 The Regents Of The University Of Michigan Methods and compositions for inhibiting rho-mediated diseases and conditions
US8673913B2 (en) 2009-11-13 2014-03-18 Case Western Reserve University SHP-2 phosphatase inhibitor
WO2012078902A2 (en) 2010-12-08 2012-06-14 Proteostasis Therapeutics, Inc. Proteostasis regulators
US20150011411A1 (en) 2011-12-21 2015-01-08 THE REGENTS OF THE UNIVERSITY OF COLORADO a body corporation Biomarkers of cancer
CA2859985C (en) 2011-12-21 2020-11-03 The Regents Of The University Of Colorado Anti-cancer compounds targeting ral gtpases and methods of using the same
WO2013152313A1 (en) * 2012-04-05 2013-10-10 The Regents Of The University Of California Compositions and methods for treating cancer and diseases and conditions responsive to growth factor inhibition
EP2858981A1 (en) * 2012-06-06 2015-04-15 Basf Se Pyrazolopyrans having herbicidal and pharmaceutical properties
CN103910737B (zh) 2014-03-25 2016-08-17 浙江师范大学 手性的1,4-二氢吡喃(2,3-c)吡唑衍生物及其合成方法和应用

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Publication number Publication date
JP6473330B2 (ja) 2019-02-20
AU2012358317A1 (en) 2014-07-17
EP2793881A1 (en) 2014-10-29
US20200270263A1 (en) 2020-08-27
CA2859985A1 (en) 2013-06-27
US20140315894A1 (en) 2014-10-23
WO2013096820A1 (en) 2013-06-27
EP2793881B1 (en) 2018-10-31
CN104271132A (zh) 2015-01-07
US10689392B2 (en) 2020-06-23
US9353121B2 (en) 2016-05-31
KR20150010696A (ko) 2015-01-28
JP2015503507A (ja) 2015-02-02
CN104271132B (zh) 2018-01-12
US11964985B2 (en) 2024-04-23
EP2793881A4 (en) 2015-05-20
AU2012358317B2 (en) 2017-12-14
US20160280715A1 (en) 2016-09-29
KR102097343B1 (ko) 2020-04-07

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