KR102165113B1 - Ａ2ａ 길항제 성질을 갖는 헤테로비시클로-치환된-[1,2,4]트리아졸로[1,5-ｃ]퀴나졸린-5-아민 화합물 - Google Patents
Ａ2ａ 길항제 성질을 갖는 헤테로비시클로-치환된-[1,2,4]트리아졸로[1,5-ｃ]퀴나졸린-5-아민 화합물 Download PDFInfo
- Publication number
- KR102165113B1 KR102165113B1 KR1020157020147A KR20157020147A KR102165113B1 KR 102165113 B1 KR102165113 B1 KR 102165113B1 KR 1020157020147 A KR1020157020147 A KR 1020157020147A KR 20157020147 A KR20157020147 A KR 20157020147A KR 102165113 B1 KR102165113 B1 KR 102165113B1
- Authority
- KR
- South Korea
- Prior art keywords
- triazolo
- amine
- methoxy
- quinazolin
- ethyl
- 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
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- 0 C=*1SC1c1cnc[o]1 Chemical compound C=*1SC1c1cnc[o]1 0.000 description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N O=C1NC=CC=C1 Chemical compound O=C1NC=CC=C1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SJMNQXLXIIXDDS-UHFFFAOYSA-N C1NCc2c1cccn2 Chemical compound C1NCc2c1cccn2 SJMNQXLXIIXDDS-UHFFFAOYSA-N 0.000 description 1
- KKBXSSJOMUKAON-UHFFFAOYSA-N CCOC(CC(NNc(c1ccc2)nc(N)nc1c2OC)=O)=O Chemical compound CCOC(CC(NNc(c1ccc2)nc(N)nc1c2OC)=O)=O KKBXSSJOMUKAON-UHFFFAOYSA-N 0.000 description 1
- CFOHRCNONSEVOJ-MRVPVSSYSA-N CC[C@@H]1CC=CCC1 Chemical compound CC[C@@H]1CC=CCC1 CFOHRCNONSEVOJ-MRVPVSSYSA-N 0.000 description 1
- RTMAFJOMBKRXCH-SECBINFHSA-N CC[C@]1(C)CC=CCC1 Chemical compound CC[C@]1(C)CC=CCC1 RTMAFJOMBKRXCH-SECBINFHSA-N 0.000 description 1
- DKTFRTHXQMXJFX-UHFFFAOYSA-N COCc1c2nc(N)[n]3nc(CN(C4)Cc5c4cccn5)nc3c2ccc1 Chemical compound COCc1c2nc(N)[n]3nc(CN(C4)Cc5c4cccn5)nc3c2ccc1 DKTFRTHXQMXJFX-UHFFFAOYSA-N 0.000 description 1
- YZGRUUWJCIUCAO-UHFFFAOYSA-N COCc1cccc2c1nc(N)[n]1nc(CCl)nc21 Chemical compound COCc1cccc2c1nc(N)[n]1nc(CCl)nc21 YZGRUUWJCIUCAO-UHFFFAOYSA-N 0.000 description 1
- XNDHOWKKQLGUGN-UHFFFAOYSA-N COc1c2nc(N)[n]3nc(CC(N4Cc5ncccc5C4)=O)nc3c2ccc1 Chemical compound COc1c2nc(N)[n]3nc(CC(N4Cc5ncccc5C4)=O)nc3c2ccc1 XNDHOWKKQLGUGN-UHFFFAOYSA-N 0.000 description 1
- FPRXKWBZQHJDPC-UHFFFAOYSA-N COc1c2nc(N)[n]3nc(CC(O)=O)nc3c2ccc1 Chemical compound COc1c2nc(N)[n]3nc(CC(O)=O)nc3c2ccc1 FPRXKWBZQHJDPC-UHFFFAOYSA-N 0.000 description 1
- ZJQDAQQPAJWURN-UHFFFAOYSA-N COc1c2nc(N)[n]3nc(CN4Cc5ncccc5CC4)nc3c2ccc1 Chemical compound COc1c2nc(N)[n]3nc(CN4Cc5ncccc5CC4)nc3c2ccc1 ZJQDAQQPAJWURN-UHFFFAOYSA-N 0.000 description 1
- DZNPOCHJCGTGCP-UHFFFAOYSA-N COc1cccc(c(Cl)n2)c1nc2Cl Chemical compound COc1cccc(c(Cl)n2)c1nc2Cl DZNPOCHJCGTGCP-UHFFFAOYSA-N 0.000 description 1
- DLFIXPTUMHDGCB-UHFFFAOYSA-N CS(OCCF)(=O)=O Chemical compound CS(OCCF)(=O)=O DLFIXPTUMHDGCB-UHFFFAOYSA-N 0.000 description 1
- WTZFMKSUEPBREG-UHFFFAOYSA-N Cc(c1n2)cccc1c(NNC(CO)=O)nc2Cl Chemical compound Cc(c1n2)cccc1c(NNC(CO)=O)nc2Cl WTZFMKSUEPBREG-UHFFFAOYSA-N 0.000 description 1
- VCPJOOVRGLLBPO-UHFFFAOYSA-N Cc(cccc12)c1nc(NCc(ccc(OC)c1)c1OC)nc2NNC(CO)=O Chemical compound Cc(cccc12)c1nc(NCc(ccc(OC)c1)c1OC)nc2NNC(CO)=O VCPJOOVRGLLBPO-UHFFFAOYSA-N 0.000 description 1
- XCIWNFKPROTKHB-UHFFFAOYSA-N Cc(cccc1c(Cl)n2)c1nc2Cl Chemical compound Cc(cccc1c(Cl)n2)c1nc2Cl XCIWNFKPROTKHB-UHFFFAOYSA-N 0.000 description 1
- IMFJPXDDHSOHKV-UHFFFAOYSA-N Cc1c2nc(N)[n]3nc(CN4Cc5ncccc5C4)nc3c2ccc1 Chemical compound Cc1c2nc(N)[n]3nc(CN4Cc5ncccc5C4)nc3c2ccc1 IMFJPXDDHSOHKV-UHFFFAOYSA-N 0.000 description 1
- HRRBZXKLAVTZHN-UHFFFAOYSA-N Cc1c2nc(NCc(ccc(OC)c3)c3OC)[n]3nc(CCl)nc3c2ccc1 Chemical compound Cc1c2nc(NCc(ccc(OC)c3)c3OC)[n]3nc(CCl)nc3c2ccc1 HRRBZXKLAVTZHN-UHFFFAOYSA-N 0.000 description 1
- URLJCVGMSXAGAX-UHFFFAOYSA-N Nc([n]1nc(CN2Cc3ncccc3CC2)nc1c1ccc2)nc1c2OCCF Chemical compound Nc([n]1nc(CN2Cc3ncccc3CC2)nc1c1ccc2)nc1c2OCCF URLJCVGMSXAGAX-UHFFFAOYSA-N 0.000 description 1
- RQOCQLWOWIEFHU-UHFFFAOYSA-N Nc1nc(c(O)ccc2)c2c2nc(CN3Cc4ncccc4CC3)n[n]12 Chemical compound Nc1nc(c(O)ccc2)c2c2nc(CN3Cc4ncccc4CC3)n[n]12 RQOCQLWOWIEFHU-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
- A61K31/4985—Pyrazines or piperazines 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
- A61K31/495—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
- 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
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2012/087865 | 2012-12-28 | ||
| PCT/CN2012/087865 WO2014101120A1 (en) | 2012-12-28 | 2012-12-28 | Heterobicyclo-substituted-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties |
| PCT/CN2013/076853 WO2014101373A1 (en) | 2012-12-28 | 2013-06-06 | Heterobicyclo-substituted-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds for treatment of central nervous system disorder |
| CNPCT/CN2013/076853 | 2013-06-06 | ||
| PCT/US2013/076781 WO2014105666A1 (en) | 2012-12-28 | 2013-12-20 | Heterobicyclo-substituted-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150100879A KR20150100879A (ko) | 2015-09-02 |
| KR102165113B1 true KR102165113B1 (ko) | 2020-10-13 |
Family
ID=51019745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157020147A Expired - Fee Related KR102165113B1 (ko) | 2012-12-28 | 2013-12-20 | Ａ2ａ 길항제 성질을 갖는 헤테로비시클로-치환된-[1,2,4]트리아졸로[1,5-ｃ]퀴나졸린-5-아민 화합물 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US9708347B2 (enExample) |
| EP (1) | EP2945632B1 (enExample) |
| JP (1) | JP6306049B2 (enExample) |
| KR (1) | KR102165113B1 (enExample) |
| AU (1) | AU2013370977B2 (enExample) |
| BR (1) | BR112015015468B8 (enExample) |
| CA (1) | CA2896056C (enExample) |
| CY (1) | CY1120258T1 (enExample) |
| DK (1) | DK2945632T3 (enExample) |
| ES (1) | ES2667477T3 (enExample) |
| HR (1) | HRP20180678T1 (enExample) |
| HU (1) | HUE037950T2 (enExample) |
| LT (1) | LT2945632T (enExample) |
| ME (1) | ME03034B (enExample) |
| MX (1) | MX370017B (enExample) |
| NO (1) | NO2945632T3 (enExample) |
| PL (1) | PL2945632T3 (enExample) |
| PT (1) | PT2945632T (enExample) |
| RS (1) | RS57162B1 (enExample) |
| RU (2) | RU2018136104A (enExample) |
| SI (1) | SI2945632T1 (enExample) |
| WO (3) | WO2014101120A1 (enExample) |
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| US10688082B2 (en) | 2015-06-11 | 2020-06-23 | Merck Sharp & Dohme Corp. | Aminopyrazine compounds with A2A antagonist properties |
| WO2017008205A1 (en) | 2015-07-10 | 2017-01-19 | Merck Sharp & Dohme Corp. | Substituted aminoquinazoline compounds as a2a antagonist |
| US10568882B2 (en) | 2015-08-21 | 2020-02-25 | Srx Cardio, Llc | Phenylpiperazine proprotein convertase subtilisin/kexin type 9 (PCSK9) modulators and their use |
| WO2017034994A1 (en) | 2015-08-21 | 2017-03-02 | Portola Pharmaceuticals, Inc. | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate pcsk9 protein activity |
| US10865185B2 (en) | 2015-08-21 | 2020-12-15 | Srx Cardio, Llc | Composition and methods of use of tetrahydroisoquinoline small molecules to bind and modulate PCSK9 protein activity |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| US10329289B2 (en) | 2015-12-23 | 2019-06-25 | Merck Sharp & Dohme Corp. | 6,7-dihydro-5H-pyrrolo[3,4-B]pyridin-5-one allosteric modulators of the M4 muscarinic acetylcholine receptor |
| WO2017107087A1 (en) * | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 6, 7-dihydro-5h-pyrrolo [3, 4-b] pyridin-5-oneallosteric modulators of the m4 muscarinic acetylcholine receptor |
| US20190119236A1 (en) | 2016-02-23 | 2019-04-25 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| JP2020506885A (ja) | 2017-01-13 | 2020-03-05 | 江蘇恒瑞医薬股▲ふん▼有限公司 | １，２，４−トリアジン−３−アミン誘導体、その製造方法、および医薬におけるその使用 |
| US11365196B2 (en) | 2017-02-27 | 2022-06-21 | Betta Pharmaceuticals Co., Ltd. | FGFR inhibitor and application thereof |
| BR112019017108A2 (pt) | 2017-03-16 | 2020-04-07 | Jiangsu Hengrui Medicine Co | derivados de heteroaril[4,3-c]pirimidina-5-amina, método de preparação dos mesmos, e usos médicos dos mesmos |
| CA3077267C (en) | 2017-09-28 | 2021-02-16 | Cstone Pharmaceuticals (Suzhou) Co., Ltd. | Fused heteroaryl ring derivatives useful as a2a receptor inhibitor |
| 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 |
| US20210032253A1 (en) | 2018-02-06 | 2021-02-04 | Jiangsu Hengrui Medicine Co., Ltd. | Pyrazolo[1,5-a][1,3,5]triazine-2-amine derivative, preparation method therefor and medical use thereof |
| 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 |
| 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 |
| 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 |
| AU2019385905B2 (en) | 2018-11-30 | 2023-01-12 | Merck Sharp & Dohme Llc | 9-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| AU2020205753B2 (en) | 2019-01-11 | 2025-05-29 | Omeros Corporation | Methods and compositions for treating cancer |
| AR117844A1 (es) | 2019-01-22 | 2021-09-01 | Merck Patent Gmbh | Derivados de tiazolopiridina como antagonistas del receptor de adenosina |
| JP7066913B2 (ja) | 2019-03-26 | 2022-05-13 | ノベルファーマ株式会社 | 持続型脂肪酸結合ＧｎＲＨ誘導体及びこれを含む薬剤学的組成物 |
| CN119874775A (zh) | 2020-02-07 | 2025-04-25 | 加舒布鲁姆生物公司 | 杂环glp-1激动剂 |
| WO2022020550A1 (en) * | 2020-07-24 | 2022-01-27 | Merck Sharp & Dohme Corp. | Adenosine a2a and a2b receptor dual antagonists for immuno-oncology |
| WO2022020552A1 (en) * | 2020-07-24 | 2022-01-27 | Merck Sharp & Dohme Corp. | Adenosine a2a and a2b receptor dual antagonists for immuno-oncology |
| CN112159411A (zh) * | 2020-10-15 | 2021-01-01 | 南京工业大学 | 一种三氟甲基取代嘧啶并[1,3]二氮杂*化合物及其制备方法 |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| KR20250004779A (ko) | 2022-04-13 | 2025-01-08 | 길리애드 사이언시즈, 인코포레이티드 | Trop-2 발현 암을 치료하기 위한 병용 요법 |
| KR20250168210A (ko) | 2023-02-16 | 2025-12-02 | 가셔브룸 바이오, 인크. | 헤테로시클릭 glp-1 효능제 |
| US20250230168A1 (en) | 2023-12-22 | 2025-07-17 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
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