WO2020128036A1 - Modulateurs du récepteur a2a de l'adénosine - Google Patents

Modulateurs du récepteur a2a de l'adénosine Download PDF

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Publication number
WO2020128036A1
WO2020128036A1 PCT/EP2019/086786 EP2019086786W WO2020128036A1 WO 2020128036 A1 WO2020128036 A1 WO 2020128036A1 EP 2019086786 W EP2019086786 W EP 2019086786W WO 2020128036 A1 WO2020128036 A1 WO 2020128036A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
fluorophenyl
alkyl
pyrazine
imidazo
Prior art date
Application number
PCT/EP2019/086786
Other languages
English (en)
Inventor
Aneta BOBOWSKA
Michal GALEZOWSKI
Joanna SZEREMETA-SPISAK
Marcin NOWOGRODZKI
Alicja OBARA
Iwona LOZINSKA-RAJ
Marcelina DUDEK
Anita JANIGA
Jacek REUS
Marek WRONOWSKI
Magdalena ZASTAWNA
Charles-Henry Fabritius
Anna RAJDA
Roderick Alan Porter
Przemyslaw Wyrebek
Mateusz SWIRSKI
Luigi Stasi
Original Assignee
Ryvu Therapeutics S.A.
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 Ryvu Therapeutics S.A. filed Critical Ryvu Therapeutics S.A.
Publication of WO2020128036A1 publication Critical patent/WO2020128036A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne les composés de formule (I) et des sels, stéréoisomères, tautomères, isotopologues ou N-oxydes de ceux-ci. La présente invention concerne en outre l'utilisation de tels composés ou sels, stéréo-isomères, tautomères, isotopologues ou N-oxydes de ceux-ci en tant que modulateurs du récepteur A2A de l'adénosine dans le traitement du cancer et une composition pharmaceutique comprenant lesdits composés.
PCT/EP2019/086786 2018-12-21 2019-12-20 Modulateurs du récepteur a2a de l'adénosine WO2020128036A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP18460085 2018-12-21
EP18460085.6 2018-12-21
EP19460042.5 2019-08-02
EP19460042 2019-08-02

Publications (1)

Publication Number Publication Date
WO2020128036A1 true WO2020128036A1 (fr) 2020-06-25

Family

ID=69143571

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2019/086786 WO2020128036A1 (fr) 2018-12-21 2019-12-20 Modulateurs du récepteur a2a de l'adénosine

Country Status (1)

Country Link
WO (1) WO2020128036A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001058241A2 (fr) 2000-02-10 2001-08-16 New York University Antagonistes des recepteurs d'adenosine a2a pour le traitement et la prevention de la cirrhose hepatique et de la steatose hepatique
WO2003048164A2 (fr) * 2001-11-30 2003-06-12 Schering Corporation Antagonistes du recepteur a2a de l'adenosine
WO2006009698A2 (fr) 2004-06-17 2006-01-26 The Regents Of The University Of California Antagonisation d'un recepteur d'adenosine a2a pour ameliorer une ou plusieurs composantes du comportement addictif
US20070037033A1 (en) 2003-09-22 2007-02-15 Nissan Motor Co., Ltd. Separator for fuel cell, fuel cell stack, method for manufacturing separator for fuel cell, and fuel cell vehicle
WO2017098421A1 (fr) 2015-12-08 2017-06-15 Glaxosmithkline Intellectual Property Development Limited Composés benzothiadiazine
WO2018166493A1 (fr) * 2017-03-16 2018-09-20 江苏恒瑞医药股份有限公司 Dérivé d'hétéroaryl[4,3-c]pyrimidine-5-amine, son procédé de préparation et ses utilisations médicales
WO2019002606A1 (fr) * 2017-06-30 2019-01-03 Selvita S.A. Modulateurs de 5,6-bicyclo-imidazo[1,2-a]pyrazine du récepteur a2a de l'adénosine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001058241A2 (fr) 2000-02-10 2001-08-16 New York University Antagonistes des recepteurs d'adenosine a2a pour le traitement et la prevention de la cirrhose hepatique et de la steatose hepatique
WO2003048164A2 (fr) * 2001-11-30 2003-06-12 Schering Corporation Antagonistes du recepteur a2a de l'adenosine
US20070037033A1 (en) 2003-09-22 2007-02-15 Nissan Motor Co., Ltd. Separator for fuel cell, fuel cell stack, method for manufacturing separator for fuel cell, and fuel cell vehicle
WO2006009698A2 (fr) 2004-06-17 2006-01-26 The Regents Of The University Of California Antagonisation d'un recepteur d'adenosine a2a pour ameliorer une ou plusieurs composantes du comportement addictif
WO2017098421A1 (fr) 2015-12-08 2017-06-15 Glaxosmithkline Intellectual Property Development Limited Composés benzothiadiazine
WO2018166493A1 (fr) * 2017-03-16 2018-09-20 江苏恒瑞医药股份有限公司 Dérivé d'hétéroaryl[4,3-c]pyrimidine-5-amine, son procédé de préparation et ses utilisations médicales
WO2019002606A1 (fr) * 2017-06-30 2019-01-03 Selvita S.A. Modulateurs de 5,6-bicyclo-imidazo[1,2-a]pyrazine du récepteur a2a de l'adénosine

Non-Patent Citations (35)

* Cited by examiner, † Cited by third party
Title
"Cancer Principles and Practice of Oncology", 15 February 2001, LIPPINCOTT WILLIAMS & WILKINS PUBLISHERS
ALLARD ET AL., CURR OPIN PHARMACOL., vol. 29, August 2016 (2016-08-01), pages 7 - 16
ALLARD ET AL., IMMUNOL CELL BIOL, vol. 95, no. 4, April 2017 (2017-04-01), pages 333 - 339
BOREA PA ET AL., PHYSIOL REV., vol. 98, no. 3, 2018, pages 1591 - 1625
BOREA PA ET AL., TRENDS PHARMACOL SCI., vol. 37, no. 6, 2016, pages 419 - 434
BRUCE N., CRONSTEIN F1000 BIOL REPORTS, vol. 3, 2011, pages 21
CANCER IMMUNOL RES., vol. 3, no. 5, May 2015 (2015-05-01), pages 506 - 17
CEKIC CLINDEN J, NAT REV IMMUNOL., vol. 16, no. 3, 2016, pages 177 - 92
CHAN ET AL., ARTHRITIS & RHEUMATISM, vol. 54, no. 8, 2006, pages 2632 - 2642
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 35920-39-9
COOPER ET AL.: "An endogenous A2B adenosine receptor coupled to cyclic AMP generation in human embryonic kidney (HEK-293) cei/sT", BRIT. J. PHARMACOL., vol. 122, pages 546
DALL'LGNA ET AL., EXPERIMENTAL NEUROLOGY, 2007, pages 241 - 245
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 23 January 2019 (2019-01-23), retrieved from stn Database accession no. 2260684-06-6 *
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 23 January 2019 (2019-01-23), retrieved from stn Database accession no. 2260684-07-7 *
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 23 January 2019 (2019-01-23), retrieved from stn Database accession no. 2260684-08-8 *
DUNWIDDIE TV ET AL., ANN. REV. NEUROSCI., vol. 24, 2001, pages 31 - 55
FREDHOLM ET AL., PROG NEUROBIOL, vol. 83, 2007, pages 263 - 76
GAO ET AL.: "Novel short-acting A2A adenosine receptor agonists for coronary vasodilation: inverse relationship between affinity and duration of action of A21A agonists", J. PHARMACOL. EXP. THER., vol. 298, pages 209
GAO ET AL.: "Novel short-acting A2A adenosine receptor agonists for coronary vasodilation: inverse relationship between affinity and duration of action ofA21A agonists", J. PHARMACOL. EXP. THER., vol. 298, pages 209
GRENZ ET AL., ANTIOXID REDOX SIGNAL, vol. 15, 2011, pages 2221 - 34,23
H KARMOUTY-QUINTANA, ARTHRITIS & REUMATOLOGY, vol. 70, no. 10, 2018, pages 1673 - 1684
J PHARMACOL EXP THER., vol. 308, no. 1, 2004, pages 358 - 66
J. CLIN. INVEST., vol. 116, 2006, pages 2173 - 2182
JENNER P., J NEUROL., vol. 247, no. 2, 2000, pages 1 143 - 50
KASAMA H ET AL., BMC CANCER, vol. 15, 2015, pages 563
KUROKOWA ET AL.: "Program No. 714.4/B101. 2009 Neuroscience Meeting Planner", 2009, SOCIETY FOR NEUROSCIENCE
LANNONE, AM J CANCER RES., vol. 4, no. 2, 1 March 2014 (2014-03-01), pages 172 - 81
MORRELLO ET AL., ONCOIMMUNOLOGY, vol. 5, no. 3, March 2016 (2016-03-01), pages e1108515
POPOLI P. ET AL., J NEUROSCI., vol. 22, 2002, pages 1967 - 75
SITKOVSKY, TRENDS IMMUNOL, vol. 30, 2009, pages 102 - 8
STONE TW. ET AL., DRAG. DEV. RES., vol. 52, 2001, pages 323 - 330
TEITA ASANOMITSUKO TAKENAGA, J CLIN MED., vol. 6, no. 11, 2017, pages 104
TUITE P ET AL., J. EXPERT OPIN. INVESTIG. DRUGS, vol. 12, 2003, pages 1335 - 52
ZHAN-GUO GAO ET AL., INT J MOL SCI., vol. 20, no. 20, 2019, pages 5139
ZHOU Y ET AL., ONCOTARGET, vol. 8, no. 30, 2017, pages 48755 - 48768

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