GB2609879B - Antagonists of the adenosine A2a receptor - Google Patents

Antagonists of the adenosine A2a receptor Download PDF

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Publication number
GB2609879B
GB2609879B GB2217519.4A GB202217519A GB2609879B GB 2609879 B GB2609879 B GB 2609879B GB 202217519 A GB202217519 A GB 202217519A GB 2609879 B GB2609879 B GB 2609879B
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GB
United Kingdom
Prior art keywords
adenosine
antagonists
receptor
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
GB2217519.4A
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English (en)
Other versions
GB2609879A (en
GB202217519D0 (en
Inventor
Mccarthy Clive
Moulton Benjamin
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.)
AdoRx Therapeutics Ltd
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AdoRx Therapeutics Ltd
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 GBGB2006823.5A external-priority patent/GB202006823D0/en
Priority claimed from GBGB2019922.0A external-priority patent/GB202019922D0/en
Application filed by AdoRx Therapeutics Ltd filed Critical AdoRx Therapeutics Ltd
Publication of GB202217519D0 publication Critical patent/GB202217519D0/en
Publication of GB2609879A publication Critical patent/GB2609879A/en
Application granted granted Critical
Publication of GB2609879B publication Critical patent/GB2609879B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5386—1,4-Oxazines, e.g. morpholine spiro-condensed or forming part of bridged ring 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/541—Non-condensed thiazines 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
GB2217519.4A 2020-05-07 2021-05-06 Antagonists of the adenosine A2a receptor Active GB2609879B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB2006823.5A GB202006823D0 (en) 2020-05-07 2020-05-07 Antagonist compounds
GBGB2019922.0A GB202019922D0 (en) 2020-12-16 2020-12-16 Antagonist compounds
PCT/GB2021/051106 WO2021224636A1 (en) 2020-05-07 2021-05-06 Antagonists of the adenosine a2a receptor

Publications (3)

Publication Number Publication Date
GB202217519D0 GB202217519D0 (en) 2023-01-04
GB2609879A GB2609879A (en) 2023-02-15
GB2609879B true GB2609879B (en) 2023-08-16

Family

ID=75977772

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2217519.4A Active GB2609879B (en) 2020-05-07 2021-05-06 Antagonists of the adenosine A2a receptor

Country Status (16)

Country Link
EP (1) EP4146654A1 (https=)
JP (2) JP7724239B2 (https=)
KR (1) KR20230035236A (https=)
CN (1) CN115996929B (https=)
AU (1) AU2021266433A1 (https=)
BR (1) BR112022022437A2 (https=)
CA (1) CA3181354A1 (https=)
CL (1) CL2022003055A1 (https=)
CO (1) CO2022017618A2 (https=)
EC (1) ECSP22091613A (https=)
GB (1) GB2609879B (https=)
IL (2) IL297963A (https=)
MX (1) MX2022013946A (https=)
PE (1) PE20230769A1 (https=)
PH (1) PH12022552987A1 (https=)
WO (1) WO2021224636A1 (https=)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4447971A4 (en) * 2021-12-17 2025-12-10 Merck Sharp & Dohme Llc PYRAZOLOPYRIMIDINE DERIVATIVES AND THEIR METHODS OF USE FOR THE TREATMENT OF HERPESVIRUS
CN116283994B (zh) * 2021-12-20 2025-01-07 艾立康药业股份有限公司 作为mat2a抑制剂的杂环化合物
CN117247386B (zh) * 2022-01-18 2025-10-24 江苏亚尧生物科技有限公司 新型吡唑并嘧啶化合物及其组合物、制备方法和用途
JP2025512384A (ja) * 2022-04-13 2025-04-17 ギリアード サイエンシーズ， インコーポレイテッド Ｔｒｏｐ－２発現がんを治療するための併用療法
WO2025094087A1 (en) 2023-10-30 2025-05-08 Johnson & Johnson Enterprise Innovation Inc. Safe administration of a2a rector antagonist
WO2025123251A1 (en) 2023-12-13 2025-06-19 Johnson & Johnson Enterprise Innovation Inc. Crystalline forms of a2a receptor antagonist, preparation methods, and uses thereof
WO2025123253A1 (en) 2023-12-13 2025-06-19 Johnson & Johnson Enterprise Innovation Inc. Pharmaceutical compositions of an a2a receptor antagonist
WO2025137640A1 (en) 2023-12-22 2025-06-26 Gilead Sciences, Inc. Azaspiro wrn inhibitors
WO2025202955A1 (en) 2024-03-28 2025-10-02 Pi Industries Ltd. Fused bicyclic compounds and their use as pest control agents
CN120093763A (zh) * 2025-03-25 2025-06-06 上海天龙生物科技有限公司 治疗前列腺疾病和腺体类散结节的药物组合物及其应用

Citations (4)

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EP1505068A1 (en) * 2002-04-23 2005-02-09 Shionogi & Co., Ltd. PYRAZOLO (1,5-a) PYRIMIDINE DERIVATIVE AND NAD(P)H OXIDASE INHIBITOR CONTAINING THE SAME
EP2402345A1 (en) * 2010-06-29 2012-01-04 Basf Se Pyrazole fused bicyclic compounds
EP2402337A1 (en) * 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
EP2402344A1 (en) * 2010-06-29 2012-01-04 Basf Se Pyrazole fused bicyclic compounds

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US3910907A (en) * 1973-07-09 1975-10-07 Icn Pharmaceuticals Pyrazolo(1,5-a)-1,3,5-triazines
US5356897A (en) * 1991-09-09 1994-10-18 Fujisawa Pharmaceutical Co., Ltd. 3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines
US8178533B2 (en) * 2005-06-01 2012-05-15 Ucb Pharma, S.A. 2-oxo-1-pyrrolidine derivatives, processes for preparing them and their uses
CN101686989B (zh) * 2007-06-21 2016-10-19 卡拉治疗学股份有限公司 取代的咪唑并杂环
US20100029657A1 (en) 2008-02-29 2010-02-04 Wyeth Bridged, Bicyclic Heterocyclic or Spiro Bicyclic Heterocyclic Derivatives of Pyrazolo[1, 5-A]Pyrimidines, Methods for Preparation and Uses Thereof
EP2402343A1 (en) * 2010-06-29 2012-01-04 Basf Se Pyrazole-fused bicyclic compounds
WO2012100342A1 (en) * 2011-01-27 2012-08-02 Université de Montréal Pyrazolopyridine and pyrazolopyrimidine derivatives as melanocortin-4 receptor modulators
ES2728932T3 (es) * 2014-01-09 2019-10-29 Intra Cellular Therapies Inc Compuestos orgánicos
CA2969265A1 (en) * 2014-12-02 2016-06-09 Bayer Pharma Aktiengesellschaft Substituted pyrazolo[1,5-a]pyridines and imidazo[1,2-a]pyrazines and their use
PE20181326A1 (es) 2015-11-03 2018-08-20 Janssen Biotech Inc Anticuerpos que se unen especificamente a pd-1 y sus usos
WO2017178844A1 (en) * 2016-04-15 2017-10-19 Cancer Research Technology Limited Heterocyclic compounds as ret kinase inhibitors
US11608334B2 (en) * 2017-02-08 2023-03-21 The National Institutes of Pharmaceutical R&D Co., Ltd. Pyrrolo-aromatic heterocyclic compound, preparation method therefor, and medical use thereof
US12398209B2 (en) 2018-01-22 2025-08-26 Janssen Biotech, Inc. Methods of treating cancers with antagonistic anti-PD-1 antibodies

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EP1505068A1 (en) * 2002-04-23 2005-02-09 Shionogi & Co., Ltd. PYRAZOLO (1,5-a) PYRIMIDINE DERIVATIVE AND NAD(P)H OXIDASE INHIBITOR CONTAINING THE SAME
EP2402345A1 (en) * 2010-06-29 2012-01-04 Basf Se Pyrazole fused bicyclic compounds
EP2402337A1 (en) * 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
EP2402344A1 (en) * 2010-06-29 2012-01-04 Basf Se Pyrazole fused bicyclic compounds

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Title
DATABASE REGISTRY [Online] , CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US, (20150617), Anonymous :"Benzonitrile, 3-pyrazolo[1,5-a]pyrimidin-2-yl-", Database accession no. 1782806-38-5, Abstract *
DATABASE REGISTRY [Online] , CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US, Anonymous "Methanone, (5-ethyl-2-hydroxyphenyl)[2-(2-furanyl)pyrazolo[1,5- a]pyrimidin-5-yl]-", (20070306), Database accession no. 924984-28-1, 924984-25-8, 924984-19-0, 924984-16-7, abstract *
DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US.(20131216), "Pyrazolo[1,5-a]pyrimidine-3-methanamine, 2-(2-furanyl)-" Database accession no. 1496345-00-6, 1496301-75-7, 1495849-63-2, * abstract *
DATABASE REGISTRY [Online], CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US, Anonymous "Pyrazolo[1,5-a]pyrimidine-3-acetonitrile, 2-(5-bromo-2-furanyl)-", (20120415), Database accession no. 1368113-54-5, 1368112-99-5, abstract *
DATABASE REGISTRY[Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US,Anonymous,"Pyrazolo[1,5-a]pyrimidine-3-carbonitrile, 2-(2-pyridinyl)-"(20120413), Database accession no.1367863-71-5, 1367833-85-9, 1367824-67-6, Abstract.Further database acession no's 1367817-15-9, 1367753-06-7 *
DE LERA RUIZ ET AL., "Adenosine A 2A Receptor as a Drug Discovery Target", J. MED. CHEM.(20131115), vol. 57, no. 9, pages 3623 - 3650 doi:10.1021/jm4011669. The whole doc. For instance: page 362, figure 2 and page 3630, fig 5: ZM241385; page 3634, fig 8: bicyclic core; page 3635, fig 9: compound 32 *
NEUSTADT ET AL., "Potent and selective adenosine A"2"A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines", BIORG. MED. CHEM. LETT., vol. 19, no. 3, (20090201) pages 967 - 971 doi:10.1016/J.BMCL.2008.11.075 [retrieved 24.11.2008], Title; abstract; page 968, table 1;page 970, table 3. *
NORMAN ET AL."N,N-Dialkyl-N'-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine...", AUSTRALIAN JRNL OF CHEM, (20151015), vol. 69, no.1, pp.61-75, p.65, scheme 11 and table 3: compound 5 with R=H *

Also Published As

Publication number Publication date
KR20230035236A (ko) 2023-03-13
CO2022017618A2 (es) 2023-02-16
EP4146654A1 (en) 2023-03-15
MX2022013946A (es) 2023-02-01
ECSP22091613A (es) 2023-03-31
GB2609879A (en) 2023-02-15
GB202217519D0 (en) 2023-01-04
WO2021224636A1 (en) 2021-11-11
IL297963A (en) 2023-01-01
PE20230769A1 (es) 2023-05-09
AU2021266433A1 (en) 2022-12-15
CN115996929A (zh) 2023-04-21
JP7724239B2 (ja) 2025-08-15
IL324071A (en) 2025-12-01
PH12022552987A1 (en) 2024-02-26
CL2022003055A1 (es) 2023-07-07
JP2023525762A (ja) 2023-06-19
BR112022022437A2 (pt) 2023-01-03
US20230203041A1 (en) 2023-06-29
CN115996929B (zh) 2026-01-13
CA3181354A1 (en) 2021-11-11
JP2025183201A (ja) 2025-12-16

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