JP6109195B2 - キナーゼ阻害剤として有用な複素環置換されたピリジル化合物 - Google Patents
キナーゼ阻害剤として有用な複素環置換されたピリジル化合物 Download PDFInfo
- Publication number
- JP6109195B2 JP6109195B2 JP2014552311A JP2014552311A JP6109195B2 JP 6109195 B2 JP6109195 B2 JP 6109195B2 JP 2014552311 A JP2014552311 A JP 2014552311A JP 2014552311 A JP2014552311 A JP 2014552311A JP 6109195 B2 JP6109195 B2 JP 6109195B2
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- JP
- Japan
- Prior art keywords
- substituted
- solvent
- acn
- alkyl
- isopropylamino
- 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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- QQPGYGHGXMLXGQ-YGPZHTELSA-N CC(C)N[C@H](CCCl)C(CN)C=O Chemical compound CC(C)N[C@H](CCCl)C(CN)C=O QQPGYGHGXMLXGQ-YGPZHTELSA-N 0.000 description 1
- IGJNPPWOFDEPSD-UHFFFAOYSA-N CC(C)Nc(cc(Nc(cc1)ccc1C#N)nc1)c1-c1nnc(C(N2CCNCC2)=O)[s]1 Chemical compound CC(C)Nc(cc(Nc(cc1)ccc1C#N)nc1)c1-c1nnc(C(N2CCNCC2)=O)[s]1 IGJNPPWOFDEPSD-UHFFFAOYSA-N 0.000 description 1
- JSADXPHJQCCHLN-CYBMUJFWSA-N CC(C)Nc(cc(Nc1cc2n[s]nc2cc1)nc1)c1-c1nnc(C(N(CC2)C[C@@H]2O)=O)[s]1 Chemical compound CC(C)Nc(cc(Nc1cc2n[s]nc2cc1)nc1)c1-c1nnc(C(N(CC2)C[C@@H]2O)=O)[s]1 JSADXPHJQCCHLN-CYBMUJFWSA-N 0.000 description 1
- KZGYPFONPYMBIF-UHFFFAOYSA-N CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1-c1cc([nH]nc2)c2cc1 Chemical compound CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1-c1cc([nH]nc2)c2cc1 KZGYPFONPYMBIF-UHFFFAOYSA-N 0.000 description 1
- CKIAHGRDNIJUIU-UHFFFAOYSA-N CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1-c1nc(C(N)=O)c[s]1 Chemical compound CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1-c1nc(C(N)=O)c[s]1 CKIAHGRDNIJUIU-UHFFFAOYSA-N 0.000 description 1
- UNUSCOSCJACYLL-UHFFFAOYSA-N CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1-c1nnc(C(N(CC2)CC2NS(C)(=O)=O)=O)[s]1 Chemical compound CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1-c1nnc(C(N(CC2)CC2NS(C)(=O)=O)=O)[s]1 UNUSCOSCJACYLL-UHFFFAOYSA-N 0.000 description 1
- WJNWVEVSXCURNR-UHFFFAOYSA-N CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1C#N Chemical compound CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1C#N WJNWVEVSXCURNR-UHFFFAOYSA-N 0.000 description 1
- NKKINTJIRCYONP-UHFFFAOYSA-N CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1C(N)=S Chemical compound CC(C)Nc(cc(Nc1ccc2nc[s]c2c1)nc1)c1C(N)=S NKKINTJIRCYONP-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)Nc(cc(nc1)Cl)c1-c1nnc(NCCC*)[o]1 Chemical compound CC(C)Nc(cc(nc1)Cl)c1-c1nnc(NCCC*)[o]1 0.000 description 1
- SXWQJSSKXJQKRM-UHFFFAOYSA-N CC(C)Nc1cc(Cl)ncc1-c1nc(C(N)=O)n[o]1 Chemical compound CC(C)Nc1cc(Cl)ncc1-c1nc(C(N)=O)n[o]1 SXWQJSSKXJQKRM-UHFFFAOYSA-N 0.000 description 1
- KXVDSEWWEHKHAD-UHFFFAOYSA-N CC(C)Nc1cc(Cl)ncc1C(NN)=O Chemical compound CC(C)Nc1cc(Cl)ncc1C(NN)=O KXVDSEWWEHKHAD-UHFFFAOYSA-N 0.000 description 1
- MPSVVZLIWUIPOL-UHFFFAOYSA-N CCOC(/C(/N)=N/N)=O Chemical compound CCOC(/C(/N)=N/N)=O MPSVVZLIWUIPOL-UHFFFAOYSA-N 0.000 description 1
- DMUYVIYISCGQSV-GOSISDBHSA-N CNC(c(cc1)ccc1Nc1cc(Nc(cc2)cc3c2nc[s]3)ncc1-c1nnc(C(N(CC2)C[C@@H]2O)=O)[s]1)=O Chemical compound CNC(c(cc1)ccc1Nc1cc(Nc(cc2)cc3c2nc[s]3)ncc1-c1nnc(C(N(CC2)C[C@@H]2O)=O)[s]1)=O DMUYVIYISCGQSV-GOSISDBHSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- C07D471/10—Spiro-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261586155P | 2012-01-13 | 2012-01-13 | |
| US61/586,155 | 2012-01-13 | ||
| PCT/US2013/021093 WO2013106612A1 (en) | 2012-01-13 | 2013-01-11 | Heterocyclic-substituted pyridyl compounds useful as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015503620A JP2015503620A (ja) | 2015-02-02 |
| JP2015503620A5 JP2015503620A5 (enExample) | 2016-02-12 |
| JP6109195B2 true JP6109195B2 (ja) | 2017-04-05 |
Family
ID=47595097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014552311A Expired - Fee Related JP6109195B2 (ja) | 2012-01-13 | 2013-01-11 | キナーゼ阻害剤として有用な複素環置換されたピリジル化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9242975B2 (enExample) |
| EP (1) | EP2802576B1 (enExample) |
| JP (1) | JP6109195B2 (enExample) |
| CN (1) | CN104159896B (enExample) |
| ES (1) | ES2686500T3 (enExample) |
| WO (1) | WO2013106612A1 (enExample) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2903617B1 (en) * | 2012-10-08 | 2019-01-30 | Merck Sharp & Dohme Corp. | Inhibitors of irak4 activity |
| SG11201503397YA (en) | 2012-11-08 | 2015-05-28 | Bristol Myers Squibb Co | Heteroaryl substituted pyridyl compounds useful as kinase modulators |
| US9546153B2 (en) | 2012-11-08 | 2017-01-17 | Bristol-Myers Squibb Company | Bicyclic heterocycle substituted pyridyl compounds useful as kinase modulators |
| GB201311888D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201311891D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| TWI667233B (zh) | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| AR098991A1 (es) | 2014-01-03 | 2016-06-22 | Bristol Myers Squibb Co | Compuestos de nicotinamida sustituida con heteroarilo |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| EP3313844B1 (en) | 2015-06-24 | 2020-08-26 | Bristol-Myers Squibb Company | Heteroaryl substituted aminopyridine compounds |
| CN109641906B (zh) | 2015-06-24 | 2021-10-01 | 百时美施贵宝公司 | 杂芳基取代的氨基吡啶化合物 |
| TW201718571A (zh) * | 2015-06-24 | 2017-06-01 | 必治妥美雅史谷比公司 | 經雜芳基取代之胺基吡啶化合物 |
| CN115448916B (zh) * | 2016-10-14 | 2026-04-28 | 武田药品工业株式会社 | Tyk2抑制剂及其用途 |
| TWI733982B (zh) | 2017-02-16 | 2021-07-21 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒衍生物 |
| US11931400B2 (en) * | 2017-03-07 | 2024-03-19 | Psomagen, Inc. | Therapeutic and diagnostics compositions targeting toll-like receptors and methods thereof |
| RS62430B1 (sr) | 2017-05-11 | 2021-11-30 | Bristol Myers Squibb Co | Tienopiridini i benzotiofeni korisni kao irak4 inhibitori |
| WO2019060693A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES THEREOF |
| JP7366031B2 (ja) | 2017-09-22 | 2023-10-20 | カイメラ セラピューティクス， インコーポレイテッド | タンパク質分解剤およびそれらの使用 |
| US11065231B2 (en) | 2017-11-17 | 2021-07-20 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of interleukin-1 receptor- associated kinase 4 polypeptides |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| EP3728228A1 (en) | 2017-12-22 | 2020-10-28 | Ravenna Pharmaceuticals, Inc. | Aminopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| US11512080B2 (en) | 2018-01-12 | 2022-11-29 | Kymera Therapeutics, Inc. | CRBN ligands and uses thereof |
| EP3737666A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | PROTEIN DEGRADATION AGENTS AND ASSOCIATED USES |
| EP3817822A4 (en) | 2018-07-06 | 2022-07-27 | Kymera Therapeutics, Inc. | PROTEIN DEGRADANTS AND USES THEREOF |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| TWI721483B (zh) | 2018-07-13 | 2021-03-11 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒𠯤衍生物 |
| TWI727392B (zh) * | 2018-08-13 | 2021-05-11 | 美商基利科學股份有限公司 | 噻二唑irak4抑制劑 |
| KR102329235B1 (ko) | 2018-11-21 | 2021-11-22 | 한국화학연구원 | Irak4 저해제로서 신규의 삼중고리 화합물 |
| WO2020106059A1 (ko) | 2018-11-21 | 2020-05-28 | 한국화학연구원 | Irak4 저해제로서 신규의 삼중고리 화합물 |
| JP7623943B2 (ja) | 2018-11-30 | 2025-01-29 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
| BR112021026517A2 (pt) | 2019-06-28 | 2022-05-10 | Kymera Therapeutics Inc | Degradadores de irak e usos dos mesmos |
| WO2021011868A1 (en) | 2019-07-17 | 2021-01-21 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| EP3999512B1 (en) | 2019-07-18 | 2023-08-23 | Bristol-Myers Squibb Company | Pyrazolo[3,4-d]pyrrolo[1,2-b]pyridazinyl compounds useful as irak4 inhibitors |
| ES2961950T3 (es) | 2019-07-18 | 2024-03-14 | Bristol Myers Squibb Co | Compuestos heteroarílicos tricíclicos útiles como inhibidores de IRAK4 |
| JP7573596B2 (ja) | 2019-07-23 | 2024-10-25 | ブリストル－マイヤーズ スクイブ カンパニー | Ｉｒａｋ４阻害剤として有用なチエノピリジニルおよびチアゾロピリジニル化合物 |
| JP7682154B2 (ja) | 2019-08-06 | 2025-05-23 | ブリストル－マイヤーズ スクイブ カンパニー | Ｉｒａｋ４阻害剤として有用な二環ヘテロ環式化合物 |
| EP4013758B1 (en) | 2019-08-13 | 2025-12-24 | Bristol-Myers Squibb Company | Bicyclic heteroaryl compounds useful as irak4 inhibitors |
| EP4072591A4 (en) | 2019-12-10 | 2024-06-05 | Kymera Therapeutics, Inc. | IRAQ DEGRADER AND USES THEREOF |
| JP2023509366A (ja) | 2019-12-17 | 2023-03-08 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| WO2021127283A2 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| US12391702B2 (en) | 2020-02-03 | 2025-08-19 | Bristol-Myers Squibb Company | Benzo[5,6][1,4]dioxino[2,3-b]pyridine compounds useful as IRAK4 inhibitors |
| JP7682191B2 (ja) | 2020-02-03 | 2025-05-23 | ブリストル－マイヤーズ スクイブ カンパニー | Ｉｒａｋ４阻害剤として有用な三環ヘテロアリール化合物 |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| WO2022147465A1 (en) | 2020-12-30 | 2022-07-07 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| TW202245788A (zh) | 2021-02-15 | 2022-12-01 | 美商凱麥拉醫療公司 | Irak4降解劑及其用途 |
| AU2022271290A1 (en) | 2021-05-07 | 2023-11-23 | Kymera Therapeutics, Inc. | Cdk2 degraders and uses thereof |
| EP4422635A4 (en) | 2021-10-29 | 2025-11-26 | Kymera Therapeutics Inc | IRAQ4 DEGRADATION AGENTS AND THEIR SYNTHESIS |
| IL314437A (en) | 2022-01-31 | 2024-09-01 | Kymera Therapeutics Inc | IRAK joints and their uses |
| WO2026005537A1 (ko) * | 2024-06-28 | 2026-01-02 | 주식회사 대웅제약 | 신규한 화합물, 및 이를 포함하는 암 또는 자가 면역 질환의 예방 또는 치료용 약학적 조성물 |
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| DE60232510D1 (de) | 2001-06-15 | 2009-07-16 | Vertex Pharma | 5-(2-aminopyrimidin-4-yl)benzisoxazole als proteinkinasehemmer |
| AUPR688101A0 (en) | 2001-08-08 | 2001-08-30 | Luminis Pty Limited | Protein domains and their ligands |
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| WO2009046416A1 (en) | 2007-10-05 | 2009-04-09 | Targegen Inc. | Anilinopyrimidines as jak kinase inhibitors |
| GB0719644D0 (en) * | 2007-10-05 | 2007-11-14 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
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| JP2012254939A (ja) * | 2009-10-07 | 2012-12-27 | Astellas Pharma Inc | オキサゾール化合物 |
| JP5770198B2 (ja) | 2009-10-30 | 2015-08-26 | ヤンセン ファーマシューティカ エヌ．ベー． | オピオイド受容体調節因子としてのフェノキシ置換ピリミジン |
| JPWO2011093501A1 (ja) | 2010-02-01 | 2013-06-06 | 日本ケミファ株式会社 | Ｇｐｒ１１９作動薬 |
| BR112013027787A2 (pt) | 2011-04-29 | 2017-06-27 | Icahn School Med Mount Sinai | compostos, composição farmacêutica, método para tratar um distúrbio proliferativo celular, método para tratar um distúrbio neurológico, métodos para inibir uma ou mais quinases, método para inibir a proliferação celular de células cancerosas, método para induzir a morte celular de células cancerosas, método para induzir a apoptose de células cancerosas, método para induzir a apoptose em uma célula e métodos para produzir compostos |
| ES2575604T3 (es) | 2012-01-13 | 2016-06-29 | Bristol-Myers Squibb Company | Compuestos de piridilo sustituidos con tiazolilo o tiadiazolilo útiles como inhibidores cinasa |
| CN104169275B (zh) | 2012-01-13 | 2017-06-09 | 百时美施贵宝公司 | 用作激酶抑制剂的三唑取代的吡啶化合物 |
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| JP2015503620A (ja) | 2015-02-02 |
| US20150011532A1 (en) | 2015-01-08 |
| WO2013106612A1 (en) | 2013-07-18 |
| CN104159896A (zh) | 2014-11-19 |
| US9242975B2 (en) | 2016-01-26 |
| ES2686500T3 (es) | 2018-10-18 |
| CN104159896B (zh) | 2017-05-24 |
| EP2802576A1 (en) | 2014-11-19 |
| EP2802576B1 (en) | 2018-06-27 |
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