CA3098189C - N-PHENYL-N'-(4-{[6-(1H-IMIDAZOL-1YL)-4-PYRIMIDINYL]AMINO}PHENYL) UREA DERIVATIVES USED AS MCT4 INHIBITORS FOR CANCER TREATMENT - Google Patents

N-PHENYL-N'-(4-{[6-(1H-IMIDAZOL-1YL)-4-PYRIMIDINYL]AMINO}PHENYL) UREA DERIVATIVES USED AS MCT4 INHIBITORS FOR CANCER TREATMENT

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Publication number
CA3098189C
CA3098189C CA3098189A CA3098189A CA3098189C CA 3098189 C CA3098189 C CA 3098189C CA 3098189 A CA3098189 A CA 3098189A CA 3098189 A CA3098189 A CA 3098189A CA 3098189 C CA3098189 C CA 3098189C
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CA
Canada
Prior art keywords
mct4
cancer
compound
subject
pharmaceutical composition
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
CA3098189A
Other languages
English (en)
French (fr)
Other versions
CA3098189A1 (en
Inventor
Yong Wu
Jay VADGAMA
Zhimin HUANG
Ke Wu
Original Assignee
CHARLES R DREW UNIVERSITY OF MEDICINE AND SCIENCE
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.)
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Publication of CA3098189A1 publication Critical patent/CA3098189A1/en
Application granted granted Critical
Publication of CA3098189C publication Critical patent/CA3098189C/en
Active legal-status Critical Current
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Classifications

    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA3098189A 2018-04-25 2019-04-25 N-PHENYL-N'-(4-{[6-(1H-IMIDAZOL-1YL)-4-PYRIMIDINYL]AMINO}PHENYL) UREA DERIVATIVES USED AS MCT4 INHIBITORS FOR CANCER TREATMENT Active CA3098189C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201862662637P 2018-04-25 2018-04-25
US62/662,637 2018-04-25
PCT/US2019/029192 WO2020033019A2 (en) 2018-04-25 2019-04-25 Novel mct4 inhibitors and uses thereof

Publications (2)

Publication Number Publication Date
CA3098189A1 CA3098189A1 (en) 2020-02-13
CA3098189C true CA3098189C (en) 2025-05-13

Family

ID=68532786

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3098189A Active CA3098189C (en) 2018-04-25 2019-04-25 N-PHENYL-N'-(4-{[6-(1H-IMIDAZOL-1YL)-4-PYRIMIDINYL]AMINO}PHENYL) UREA DERIVATIVES USED AS MCT4 INHIBITORS FOR CANCER TREATMENT

Country Status (7)

Country Link
US (1) US10919878B2 (OSRAM)
EP (1) EP3784650B1 (OSRAM)
JP (1) JP7115671B2 (OSRAM)
CN (1) CN112888673B (OSRAM)
AU (1) AU2019317518B2 (OSRAM)
CA (1) CA3098189C (OSRAM)
WO (1) WO2020033019A2 (OSRAM)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12544375B2 (en) * 2019-09-05 2026-02-10 The Board Of Trustees Of The Leland Junior University Small molecule therapeutic for parkinson's disease paired with a biomarker of therapeutic activity
WO2021249969A1 (en) * 2020-06-10 2021-12-16 Merck Patent Gmbh Combination product for the treatment of cancer diseases
US20240270749A1 (en) 2021-05-21 2024-08-15 Cemm - Forschungszentrum Für Molekulare Medizin Gmbh 1,2,4-triazolo[1,5-a]pyrimidine-based slc16a3 inhibitors and their therapeutic use
WO2022243574A1 (en) 2021-05-21 2022-11-24 Cemm - Forschungszentrum Für Molekulare Medizin Gmbh 3-(phthalazin-1-yl)benzenesulfonamide-based slc16a3 inhibitors and their therapeutic use

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1226438A (OSRAM) 1968-12-03 1971-03-31
GB0327734D0 (en) * 2003-11-28 2003-12-31 Novartis Ag Organic compounds
TW200804349A (en) * 2005-12-23 2008-01-16 Kalypsys Inc Novel substituted pyrimidinyloxy ureas as inhibitors of protein kinases
WO2010089580A1 (en) * 2009-02-06 2010-08-12 Astrazeneca Ab Use of a mct1 inhibitor in the treatment of cancers expressing mct1 over mct4
CN102731413A (zh) * 2011-04-15 2012-10-17 上海医药工业研究院 一种脲类化合物、其制备方法、其中间体及其应用
WO2014189152A1 (en) 2013-05-24 2014-11-27 Otsuka Pharmaceutical Co., Ltd. Pharmaceutical combination comprising metformin and dihydroquercetin and its use for the treatment of cancer
JP2017538689A (ja) 2014-11-17 2017-12-28 ニーロジョン セラピューティクス インコーポレイテッドＮｉｒｏｇｙｏｎｅ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． モノカルボン酸輸送修飾薬およびその使用
WO2016118822A1 (en) * 2015-01-22 2016-07-28 The Scripps Research Institute Chromenone inhibitors of monocarboxylate transporters
WO2016118823A1 (en) 2015-01-22 2016-07-28 The Scripps Research Institute Pteridine dione monocarboxylate transporter inhibitors
AU2016277126A1 (en) * 2015-06-12 2017-12-14 Vettore, LLC MCT4 inhibitors for treating disease
AU2017444054B2 (en) * 2017-12-21 2021-10-07 Hefei Institutes Of Physical Science, Chinese Academy Of Sciences Class of pyrimidine derivative kinase inhibitors

Also Published As

Publication number Publication date
AU2019317518A1 (en) 2020-12-17
CA3098189A1 (en) 2020-02-13
AU2019317518B2 (en) 2023-05-25
EP3784650A4 (en) 2022-01-26
EP3784650B1 (en) 2023-09-06
WO2020033019A2 (en) 2020-02-13
CN112888673A (zh) 2021-06-01
CN112888673B (zh) 2022-07-29
US20190352282A1 (en) 2019-11-21
WO2020033019A3 (en) 2020-04-02
US10919878B2 (en) 2021-02-16
JP7115671B2 (ja) 2022-08-09
EP3784650C0 (en) 2023-09-06
JP2021522345A (ja) 2021-08-30
EP3784650A2 (en) 2021-03-03

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