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)
- 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)
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 (OSRAM) |
| EP (1) | EP3220910B1 (OSRAM) |
| JP (2) | JP6779204B2 (OSRAM) |
| KR (1) | KR20170083136A (OSRAM) |
| CN (1) | CN107106558A (OSRAM) |
| AU (1) | AU2015350315B2 (OSRAM) |
| BR (1) | BR112017010261A2 (OSRAM) |
| CA (1) | CA2967944C (OSRAM) |
| MX (1) | MX381180B (OSRAM) |
| RU (1) | RU2727805C2 (OSRAM) |
| WO (1) | WO2016081290A1 (OSRAM) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018013597A1 (en) * | 2016-07-12 | 2018-01-18 | Revolution Medicines, Inc. | 2,5-disubstituted 3-methyl pyrazines and 2,5,6-trisubstituted 3-methyl pyrazines as allosteric shp2 inhibitors |
| BR112019014527A2 (pt) | 2017-01-23 | 2020-02-27 | Revolution Medicines, Inc. | Compostos de piridina como inibidores de shp2 alostéricos |
| AR110740A1 (es) | 2017-01-23 | 2019-05-02 | Revolution Medicines Inc | Compuestos bicíclicos como inhibidores alostéricos de shp2 |
| CN108570054B (zh) * | 2017-03-07 | 2021-07-16 | 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 |
| MX2020000690A (es) | 2017-07-18 | 2020-07-29 | Nuvation Bio Inc | Compuestos heterociclicos como antagonistas de adenosina. |
| BR112020000962A2 (pt) | 2017-07-18 | 2020-07-14 | Nuvation Bio Inc. | compostos de 1,8-naftiridinona e usos dos mesmos |
| WO2019046784A1 (en) | 2017-08-31 | 2019-03-07 | Corvus Pharmaceuticals, Inc. | COMPOUNDS AND METHODS FOR MODULATION OF A2B RECEPTOR OF ADENOSINE AND A2A RECEPTOR OF ADENOSINE |
| CN111212834B (zh) | 2017-10-12 | 2024-01-19 | 锐新医药公司 | 作为变构shp2抑制剂的吡啶、吡嗪和三嗪化合物 |
| US11498923B2 (en) | 2017-12-13 | 2022-11-15 | Merck Sharp & Dohme Llc | Substituted imidazo[1,2-c]quinazolines as A2A antagonists |
| BR112020009757A2 (pt) | 2017-12-15 | 2020-11-03 | Revolution Medicines, Inc. | compostos policíclicos como inibidores alostéricos de shp2 |
| MX2021001581A (es) | 2018-08-16 | 2021-04-19 | Innate Tumor Immunity Inc | Compuestos de 4-amino-1h-imidazo[4,5-c]quinolina sustituidos y metodos mejorados para su preparacion. |
| EP3616753A1 (en) * | 2018-08-31 | 2020-03-04 | Corvus Pharmaceuticals, Inc. | Compounds for modulating adenosine a2b receptor and adenosine a2a receptor |
| EP3883576B1 (en) | 2018-11-20 | 2025-12-17 | Merck Sharp & Dohme LLC | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| MA55142A (fr) | 2018-11-20 | 2022-02-23 | Merck Sharp & Dohme | Amino-triazolopyrimidine et amino-triazolopyrazine substitués antagoniste du récepteur de l'adénosine, compositions pharmaceutiques et leur utilisation |
| US11312719B2 (en) | 2018-11-30 | 2022-04-26 | Merck Sharp & Dohme Corp. | 9-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| BR112021010273A2 (pt) | 2018-11-30 | 2021-08-17 | Merck Sharp & Dohme Corp. | derivados de amino triazolo quinazolina substituídos em 7, 8 e 10 como antagonistas do receptor de adenosina, composições farmacêuticas e seu uso |
| CN113727999A (zh) | 2019-01-11 | 2021-11-30 | 奥默罗斯公司 | 用于治疗癌症的方法和组合物 |
| CA3126931A1 (en) | 2019-01-18 | 2020-07-23 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| EP3911323A4 (en) | 2019-01-18 | 2022-11-16 | 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 |
| WO2023201267A1 (en) | 2022-04-13 | 2023-10-19 | Gilead Sciences, Inc. | Combination therapy for treating trop-2 expressing cancers |
| 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 |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
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 |
| AU7237294A (en) | 1993-07-27 | 1995-02-28 | Kyowa Hakko Kogyo Co. Ltd. | Remedy 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 |
| MXPA02011625A (es) | 2000-05-26 | 2003-03-27 | Schering Corp | Antagonistas receptores de adenosina a2a. |
| SE0203754D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| US20060135523A1 (en) * | 2003-06-18 | 2006-06-22 | Astrazeneca Ab | 2-substituted 5,6-diaryl-pyrazine derivatives as cb1 modulator |
| EP1678160A1 (en) | 2003-10-27 | 2006-07-12 | Astellas Pharma Inc. | Pyrazine derivatives and pharmaceutical use thereof |
| 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. |
| WO2010141275A1 (en) * | 2009-06-01 | 2010-12-09 | Merck Sharp & Dohme Corp. | Pyrazine carboxamide orexin receptor antagonists |
-
2015
- 2015-11-13 CN CN201580073488.3A patent/CN107106558A/zh active Pending
- 2015-11-13 MX MX2017006483A patent/MX381180B/es unknown
- 2015-11-13 KR KR1020177016281A patent/KR20170083136A/ko not_active Withdrawn
- 2015-11-13 CA CA2967944A patent/CA2967944C/en not_active Expired - Fee Related
- 2015-11-13 US US15/525,788 patent/US10472347B2/en active Active
- 2015-11-13 BR BR112017010261-7A patent/BR112017010261A2/pt not_active IP Right Cessation
- 2015-11-13 JP JP2017526527A patent/JP6779204B2/ja not_active Expired - Fee Related
- 2015-11-13 RU RU2017120853A patent/RU2727805C2/ru active
- 2015-11-13 EP EP15861650.8A patent/EP3220910B1/en active Active
- 2015-11-13 WO PCT/US2015/060509 patent/WO2016081290A1/en not_active Ceased
- 2015-11-13 AU AU2015350315A patent/AU2015350315B2/en not_active Ceased
-
2020
- 2020-08-19 JP JP2020138418A patent/JP2020193211A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP3220910A4 (en) | 2018-04-25 |
| US10472347B2 (en) | 2019-11-12 |
| CA2967944A1 (en) | 2016-05-26 |
| CN107106558A (zh) | 2017-08-29 |
| JP2020193211A (ja) | 2020-12-03 |
| US20180327385A1 (en) | 2018-11-15 |
| AU2015350315B2 (en) | 2020-06-25 |
| WO2016081290A1 (en) | 2016-05-26 |
| RU2727805C2 (ru) | 2020-07-24 |
| RU2017120853A3 (OSRAM) | 2019-06-17 |
| MX381180B (es) | 2025-03-12 |
| MX2017006483A (es) | 2017-09-12 |
| AU2015350315A1 (en) | 2017-05-18 |
| RU2017120853A (ru) | 2018-12-19 |
| JP2017533946A (ja) | 2017-11-16 |
| BR112017010261A2 (pt) | 2018-02-06 |
| EP3220910A1 (en) | 2017-09-27 |
| JP6779204B2 (ja) | 2020-11-04 |
| EP3220910B1 (en) | 2020-01-15 |
| KR20170083136A (ko) | 2017-07-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20181030 |
|
| MKLA | Lapsed |
Effective date: 20211115 |