CA2967944C - Aminopyrazine compounds with a2a antagonist properties - Google Patents
Aminopyrazine compounds with a2a antagonist properties Download PDFInfo
- 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
- Authority
- 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
Links
Classifications
-
- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic 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
- C07D241/14—Heterocyclic 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/02—Heterocyclic 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
- C07D401/12—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/14—Heterocyclic 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
-
- 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
-
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic 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
- C07D413/04—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic 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
- C07D417/14—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic 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
- C07D471/02—Heterocyclic 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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic 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
- C07D513/02—Heterocyclic 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
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (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)
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) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CR20190063A (es) * | 2016-07-12 | 2019-05-27 | Revolution Medicines Inc | 3-metil pirazinas 2,5-disustituídas y 3-metil pirazinas 2,5,6-trisustituídas como inhibidores alostéricos de shp2 |
| 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 |
| BR112019015075A2 (pt) | 2017-01-23 | 2020-03-10 | Revolution Medicines, Inc. | Compostos bicíclicos como inibidores de shp2 alostéricos |
| EP3594216B1 (en) * | 2017-03-07 | 2022-04-06 | Guangzhou Maxinovel Pharmaceuticals Co., Ltd. | Aminopyrimidine five-membered heterocyclic compound, and intermediate, preparation method, pharmaceutical composition and application thereof |
| KR20200040764A (ko) | 2017-07-18 | 2020-04-20 | 누베이션 바이오 인크. | 1,8-나프티리디논 화합물 및 그의 용도 |
| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| CN111629728A (zh) | 2017-08-31 | 2020-09-04 | 科尔沃斯制药股份有限公司 | 用于调节腺苷a2b受体和腺苷a2a受体的化合物和方法 |
| JP2020536881A (ja) | 2017-10-12 | 2020-12-17 | 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阻害剤としてのピリジン、ピラジンおよびトリアジン化合物 |
| EP3723754A4 (en) | 2017-12-13 | 2021-05-19 | Merck Sharp & Dohme Corp. | IMIDAZO [1,2-C] QUINAZOLINE-5-AMINE COMPOUNDS WITH PROPERTIES OF A2A ANTAGONIST |
| CA3084058A1 (en) | 2017-12-15 | 2019-06-20 | Revolution Medicines, Inc. | Polycyclic compounds as allosteric shp2 inhibitors |
| WO2020037094A1 (en) | 2018-08-16 | 2020-02-20 | Innate Tumor Immunity, Inc. | Substitued 4-amino-1h-imidazo[4,5-c]quinoline compounds and improved methods for their preparation |
| US20200079793A1 (en) * | 2018-08-31 | 2020-03-12 | Corvus Pharmaceuticals, Inc. | Compounds and methods for modulating adenosine a2b receptor and adenosine a2a receptor |
| CA3119774A1 (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 |
| US12414952B2 (en) | 2018-11-20 | 2025-09-16 | Merck Sharp & Dohme Llc | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| AU2019388872A1 (en) | 2018-11-30 | 2021-05-27 | Merck Sharp & Dohme Llc | 7-, 8-, and 10-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| 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 |
| BR112021012685A2 (pt) | 2019-01-11 | 2021-12-28 | Omeros Corp | Métodos para tratar câncer, para aumentar o nível de citocinas th1 nas células mononucleares de sangue periférico humanas, para realçar uma resposta imune antitumoral e para estimular e/ou amplificar uma resposta imune em um sujeito mamífero sofrendo de ou em risco de desenvolver câncer ou metástase de câncer, e, composição farmacêutica |
| AU2020207951A1 (en) | 2019-01-18 | 2021-08-26 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| KR20210116550A (ko) | 2019-01-18 | 2021-09-27 | 누베이션 바이오 인크. | 아데노신 길항제로서의 헤테로시클릭 화합물 |
| 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 |
| CA3243098A1 (en) | 2022-01-28 | 2023-08-03 | BioAge Labs, Inc. | NLRP3 Inflammasome N-Oxide Inhibitors |
| KR20250004779A (ko) | 2022-04-13 | 2025-01-08 | 길리애드 사이언시즈, 인코포레이티드 | Trop-2 발현 암을 치료하기 위한 병용 요법 |
| US12516018B2 (en) * | 2023-03-30 | 2026-01-06 | Brandeis University | Solid-solid phase change aromatic azo compounds, method of manufacture, and use for thermal energy storage and release |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| US12509459B2 (en) | 2024-03-26 | 2025-12-30 | BioAge Labs, Inc. | Inhibitors of NLRP3 inflammasome |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1264901B1 (it) | 1993-06-29 | 1996-10-17 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina |
| CA2144330A1 (en) | 1993-07-27 | 1995-02-09 | Fumio Suzuki | A therapeutic agent for parkinson's disease |
| IT1277392B1 (it) | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
| IT1291372B1 (it) | 1997-05-21 | 1999-01-07 | Schering Plough S P A | Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie |
| KR100520907B1 (ko) | 2000-05-26 | 2005-10-11 | 쉐링 코포레이션 | 아데노신 Ａ2ａ수용체 길항제 |
| SE0203754D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| CA2527033A1 (en) | 2003-06-18 | 2004-12-23 | Astrazeneca Ab | 2-substitued 5,6-diaryl-pyrazine derivatives as cb1 modulators |
| RU2006118325A (ru) * | 2003-10-27 | 2007-12-10 | Астеллас Фарма Инк. (Jp) | Производные пиразина и их фармацевтическое применение |
| US20060199828A1 (en) * | 2005-03-04 | 2006-09-07 | Georg Jaeschke | Pyrazine-2-carboxyamide derivatives |
| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| US20120065205A1 (en) * | 2009-06-01 | 2012-03-15 | Mercer Swati P | Pyrazine carboxamide orexin receptor antagonists |
-
2015
- 2015-11-13 CA CA2967944A patent/CA2967944C/en not_active Expired - Fee Related
- 2015-11-13 WO PCT/US2015/060509 patent/WO2016081290A1/en not_active Ceased
- 2015-11-13 BR BR112017010261-7A patent/BR112017010261A2/pt not_active IP Right Cessation
- 2015-11-13 CN CN201580073488.3A patent/CN107106558A/zh active Pending
- 2015-11-13 MX MX2017006483A patent/MX381180B/es unknown
- 2015-11-13 EP EP15861650.8A patent/EP3220910B1/en active Active
- 2015-11-13 US US15/525,788 patent/US10472347B2/en active Active
- 2015-11-13 AU AU2015350315A patent/AU2015350315B2/en not_active Ceased
- 2015-11-13 RU RU2017120853A patent/RU2727805C2/ru active
- 2015-11-13 JP JP2017526527A patent/JP6779204B2/ja not_active Expired - Fee Related
- 2015-11-13 KR KR1020177016281A patent/KR20170083136A/ko not_active Withdrawn
-
2020
- 2020-08-19 JP JP2020138418A patent/JP2020193211A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP3220910A1 (en) | 2017-09-27 |
| MX2017006483A (es) | 2017-09-12 |
| US10472347B2 (en) | 2019-11-12 |
| JP2017533946A (ja) | 2017-11-16 |
| JP2020193211A (ja) | 2020-12-03 |
| RU2727805C2 (ru) | 2020-07-24 |
| KR20170083136A (ko) | 2017-07-17 |
| MX381180B (es) | 2025-03-12 |
| CN107106558A (zh) | 2017-08-29 |
| WO2016081290A1 (en) | 2016-05-26 |
| AU2015350315A1 (en) | 2017-05-18 |
| JP6779204B2 (ja) | 2020-11-04 |
| RU2017120853A3 (enExample) | 2019-06-17 |
| AU2015350315B2 (en) | 2020-06-25 |
| EP3220910A4 (en) | 2018-04-25 |
| US20180327385A1 (en) | 2018-11-15 |
| BR112017010261A2 (pt) | 2018-02-06 |
| EP3220910B1 (en) | 2020-01-15 |
| RU2017120853A (ru) | 2018-12-19 |
| CA2967944A1 (en) | 2016-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20181030 |
|
| MKLA | Lapsed |
Effective date: 20211115 |