CA2967944C - Aminopyrazine compounds with a2a antagonist properties - Google Patents

Aminopyrazine compounds with a2a antagonist properties Download PDF

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Publication number
CA2967944C
CA2967944C CA2967944A CA2967944A CA2967944C CA 2967944 C CA2967944 C CA 2967944C CA 2967944 A CA2967944 A CA 2967944A CA 2967944 A CA2967944 A CA 2967944A CA 2967944 C CA2967944 C CA 2967944C
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CA
Canada
Prior art keywords
methyl
amino
pyrazine
carboxamide
oxazol
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.)
Expired - Fee Related
Application number
CA2967944A
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English (en)
French (fr)
Other versions
CA2967944A1 (en
Inventor
Rongze Kuang
Pauline Ting
Amjad Ali
Heping Wu
Michael Berlin
Andrew Stamford
Hongwu Wang
Gang Zhou
David Kim
Qiaolin Deng
Yeon-Hee Lim
Younong Yu
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Merck Sharp and Dohme LLC
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Merck Sharp and Dohme LLC
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Publication of CA2967944A1 publication Critical patent/CA2967944A1/en
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Publication of CA2967944C publication Critical patent/CA2967944C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • A61K31/395Heterocyclic 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
    • A61K31/4965Non-condensed pyrazines
    • A61K31/497Non-condensed pyrazines containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • 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
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D241/26Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D513/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA2967944A 2014-11-18 2015-11-13 Aminopyrazine compounds with a2a antagonist properties Expired - Fee Related CA2967944C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201462081262P 2014-11-18 2014-11-18
US62/081,262 2014-11-18
PCT/US2015/060509 WO2016081290A1 (en) 2014-11-18 2015-11-13 Aminopyrazine compounds with a2a antagonist properties

Publications (2)

Publication Number Publication Date
CA2967944A1 CA2967944A1 (en) 2016-05-26
CA2967944C true CA2967944C (en) 2020-11-17

Family

ID=56014406

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2967944A Expired - Fee Related CA2967944C (en) 2014-11-18 2015-11-13 Aminopyrazine compounds with a2a antagonist properties

Country Status (11)

Country Link
US (1) US10472347B2 (enExample)
EP (1) EP3220910B1 (enExample)
JP (2) JP6779204B2 (enExample)
KR (1) KR20170083136A (enExample)
CN (1) CN107106558A (enExample)
AU (1) AU2015350315B2 (enExample)
BR (1) BR112017010261A2 (enExample)
CA (1) CA2967944C (enExample)
MX (1) MX381180B (enExample)
RU (1) RU2727805C2 (enExample)
WO (1) WO2016081290A1 (enExample)

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JP7240319B2 (ja) 2017-01-23 2023-03-15 レヴォリューション・メディスンズ,インコーポレイテッド アロステリックshp2阻害剤としての二環式化合物
CN110431134A (zh) 2017-01-23 2019-11-08 锐新医药公司 作为变构shp2抑制剂的吡啶化合物
WO2018161910A1 (zh) * 2017-03-07 2018-09-13 广州再极医药科技有限公司 氨基嘧啶并五元杂环化合物、其中间体、制备方法、药物组合物及应用
BR112020000962A2 (pt) 2017-07-18 2020-07-14 Nuvation Bio Inc. compostos de 1,8-naftiridinona e usos dos mesmos
JP2020527588A (ja) * 2017-07-18 2020-09-10 ニューベイション・バイオ・インコーポレイテッドNuvation Bio Inc. アデノシンアンタゴニストとしてのヘテロ環式化合物
EP3675856A4 (en) 2017-08-31 2021-04-14 Corvus Pharmaceuticals, Inc. COMPOUNDS AND METHODS FOR MODULATING THE A2B ADENOSINE RECEPTOR AND A2A ADENOSINE RECEPTOR
EP3694848A1 (en) 2017-10-12 2020-08-19 Revolution Medicines, Inc. Pyridine, pyrazine, and triazine compounds as allosteric shp2 inhibitors
US11498923B2 (en) 2017-12-13 2022-11-15 Merck Sharp & Dohme Llc Substituted imidazo[1,2-c]quinazolines as A2A antagonists
TW201927791A (zh) 2017-12-15 2019-07-16 美商銳新醫藥公司 作為變構shp2抑制劑的多環化合物
JP2021534180A (ja) 2018-08-16 2021-12-09 イネイト・テューマー・イミュニティ・インコーポレイテッドInnate Tumor Immunity, Inc. 置換4−アミノ−1H−イミダゾ[4,5−c]キノリン化合物およびその製造の改良法
EP3616753A1 (en) * 2018-08-31 2020-03-04 Corvus Pharmaceuticals, Inc. Compounds for modulating adenosine a2b receptor and adenosine a2a receptor
WO2020106560A1 (en) 2018-11-20 2020-05-28 Merck Sharp & Dohme Corp. Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use
CN113015530A (zh) 2018-11-20 2021-06-22 默沙东公司 取代的氨基三唑并嘧啶和氨基三唑并吡嗪腺苷受体拮抗剂、药物组合物及其用途
JOP20210117A1 (ar) 2018-11-30 2023-01-30 Merck Sharp & Dohme مشتقات أمينو ترايازولو كوينازولين بها استبدال في الموضع-9 كمضادات مستقبل أدينوزين، تركيبات صيدلانية واستخدامها
KR20210097152A (ko) 2018-11-30 2021-08-06 머크 샤프 앤드 돔 코포레이션 아데노신 수용체 길항제로서의 7-, 8- 및 10-치환된 아미노 트리아졸로 퀴나졸린 유도체, 제약 조성물 및 그의 용도
WO2020146795A1 (en) 2019-01-11 2020-07-16 Omeros Corporation Methods and compositions for treating cancer
CA3126931A1 (en) 2019-01-18 2020-07-23 Nuvation Bio Inc. 1,8-naphthyridinone compounds and uses thereof
AU2020208644A1 (en) 2019-01-18 2021-08-26 Nuvation Bio Inc. Heterocyclic compounds as adenosine antagonists
TW202128650A (zh) * 2019-10-11 2021-08-01 德商拜耳動物保健有限公司 作為殺蟲劑之新穎的雜芳基取代之吡𠯤衍生物
CN111285798A (zh) * 2020-04-09 2020-06-16 阿里生物新材料(常州)有限公司 一种(3-环丙基吡啶-2-基)甲胺盐酸盐的合成方法
CN111423364A (zh) * 2020-05-19 2020-07-17 阿里生物新材料(常州)有限公司 一种(3-环丙基吡啶-2-基)甲胺的合成方法
EP3929189A1 (en) * 2020-06-25 2021-12-29 Bayer Animal Health GmbH Novel heteroaryl-substituted pyrazine derivatives as pesticides
TW202304865A (zh) 2021-03-23 2023-02-01 美商百愛及生物醫藥公司 Nlrp3發炎體之抑制劑
EP4469460A1 (en) 2022-01-28 2024-12-04 Bioage Labs, Inc. N-oxide inhibitors of nlrp3 inflammasome
KR20250004779A (ko) 2022-04-13 2025-01-08 길리애드 사이언시즈, 인코포레이티드 Trop-2 발현 암을 치료하기 위한 병용 요법
US20250074870A1 (en) * 2023-03-30 2025-03-06 Brandeis University Solid-solid phase change aromatic azo compounds, method of manufacture, and use for thermal energy storage and release
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Also Published As

Publication number Publication date
EP3220910A4 (en) 2018-04-25
US20180327385A1 (en) 2018-11-15
RU2727805C2 (ru) 2020-07-24
RU2017120853A3 (enExample) 2019-06-17
MX381180B (es) 2025-03-12
CA2967944A1 (en) 2016-05-26
EP3220910A1 (en) 2017-09-27
BR112017010261A2 (pt) 2018-02-06
AU2015350315B2 (en) 2020-06-25
KR20170083136A (ko) 2017-07-17
WO2016081290A1 (en) 2016-05-26
RU2017120853A (ru) 2018-12-19
JP6779204B2 (ja) 2020-11-04
JP2020193211A (ja) 2020-12-03
EP3220910B1 (en) 2020-01-15
US10472347B2 (en) 2019-11-12
JP2017533946A (ja) 2017-11-16
MX2017006483A (es) 2017-09-12
AU2015350315A1 (en) 2017-05-18
CN107106558A (zh) 2017-08-29

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