BR112020014516A2 - Aminopirrolotriazinas como inibidores de quinase - Google Patents
Aminopirrolotriazinas como inibidores de quinase Download PDFInfo
- Publication number
- BR112020014516A2 BR112020014516A2 BR112020014516-5A BR112020014516A BR112020014516A2 BR 112020014516 A2 BR112020014516 A2 BR 112020014516A2 BR 112020014516 A BR112020014516 A BR 112020014516A BR 112020014516 A2 BR112020014516 A2 BR 112020014516A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- phenyl
- halo
- haloalkyl
- alkoxy
- Prior art date
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- VPTRWECDZZUXIF-UHFFFAOYSA-N N1=NNC2=CC=NC2=C1N Chemical class N1=NNC2=CC=NC2=C1N VPTRWECDZZUXIF-UHFFFAOYSA-N 0.000 title description 4
- 229940043355 kinase inhibitor Drugs 0.000 title description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 211
- 125000005843 halogen group Chemical group 0.000 claims description 135
- 125000000217 alkyl group Chemical group 0.000 claims description 133
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 111
- -1 or C1-3dialkylamino Chemical group 0.000 claims description 110
- 150000003839 salts Chemical class 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 87
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 85
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 78
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 64
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
- 150000002431 hydrogen Chemical group 0.000 claims description 60
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 32
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 21
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 18
- 125000000335 thiazolyl group Chemical group 0.000 claims description 17
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- 208000011231 Crohn disease Diseases 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 8
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003566 oxetanyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000000532 dioxanyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical compound C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims description 3
- 125000005495 pyridazyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 102000005403 Casein Kinases Human genes 0.000 claims 2
- 108010031425 Casein Kinases Proteins 0.000 claims 2
- 102100022501 Receptor-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims 2
- 235000008375 Decussocarpus nagi Nutrition 0.000 claims 1
- 244000309456 Decussocarpus nagi Species 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 312
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 171
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
- 239000000203 mixture Substances 0.000 description 132
- 239000012071 phase Substances 0.000 description 103
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 101
- 210000004027 cell Anatomy 0.000 description 93
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 79
- 230000027455 binding Effects 0.000 description 79
- 239000011541 reaction mixture Substances 0.000 description 76
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
- 239000002585 base Substances 0.000 description 69
- 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 69
- 239000007787 solid Substances 0.000 description 69
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 66
- 239000005695 Ammonium acetate Substances 0.000 description 66
- 235000019257 ammonium acetate Nutrition 0.000 description 66
- 229940043376 ammonium acetate Drugs 0.000 description 66
- 239000000243 solution Substances 0.000 description 65
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 63
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 26
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- 125000003118 aryl group Chemical group 0.000 description 18
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Classifications
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- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic 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 |
|---|---|---|---|
| US201862622415P | 2018-01-26 | 2018-01-26 | |
| US62/622,415 | 2018-01-26 | ||
| PCT/US2019/014918 WO2019147782A1 (en) | 2018-01-26 | 2019-01-24 | Aminopyrrolotriazines as kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR112020014516A2 true BR112020014516A2 (pt) | 2020-12-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112020014516-5A BR112020014516A2 (pt) | 2018-01-26 | 2019-01-24 | Aminopirrolotriazinas como inibidores de quinase |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US11618753B2 (https=) |
| EP (1) | EP3743430B1 (https=) |
| JP (1) | JP7307734B2 (https=) |
| KR (1) | KR102759231B1 (https=) |
| CN (1) | CN112262139B (https=) |
| AR (1) | AR114186A1 (https=) |
| AU (1) | AU2019211382B2 (https=) |
| BR (1) | BR112020014516A2 (https=) |
| CA (1) | CA3088548A1 (https=) |
| EA (1) | EA202091777A1 (https=) |
| ES (1) | ES2959399T3 (https=) |
| IL (1) | IL276269A (https=) |
| MX (1) | MX2020007531A (https=) |
| SG (1) | SG11202007035YA (https=) |
| TW (1) | TW201940485A (https=) |
| WO (1) | WO2019147782A1 (https=) |
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|---|---|---|---|---|
| EP3580220B1 (en) | 2017-02-13 | 2021-11-17 | Bristol-Myers Squibb Company | Aminotriazolopyridines as kinase inhibitors |
| DK3704118T3 (da) | 2017-10-30 | 2022-03-14 | Bristol Myers Squibb Co | Aminoimidazopyrazin som kinasehæmmere |
| EP3849969B1 (en) | 2018-09-13 | 2023-04-19 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| EP3849968B1 (en) | 2018-09-13 | 2022-12-21 | Bristol-Myers Squibb Company | 1h-indazole carboxamides as receptor-interacting protein kinase 1 inhibitors (ripk1) |
| WO2021067654A1 (en) | 2019-10-03 | 2021-04-08 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| KR20220139947A (ko) * | 2020-02-07 | 2022-10-17 | 샌트랄 글래스 컴퍼니 리미티드 | 경화성 조성물, 경화물, 전자 디바이스, 표시 장치, 광학 부재, 중합체, 감광성 조성물, 패턴 및 화합물 |
| WO2022007921A1 (zh) * | 2020-07-10 | 2022-01-13 | 北京范恩柯尔生物科技有限公司 | 三嗪类化合物及其组合物和用途 |
| CN111925345B (zh) * | 2020-08-21 | 2023-09-29 | 上海科利生物医药有限公司 | 一种手性2-氨甲基四氢呋喃的制备方法 |
| AR123793A1 (es) | 2020-10-19 | 2023-01-11 | Bristol Myers Squibb Co | Compuestos de triazolopiridinilo como inhibidores de quinasas |
| CN116745361A (zh) * | 2021-02-10 | 2023-09-12 | 中央硝子株式会社 | 树脂组合物、树脂膜、基材、聚合物以及聚合性单体 |
| CN113563214B (zh) * | 2021-07-06 | 2024-02-02 | 山东鲁泰控股集团有限公司石墨烯高分子复合材料研发中心 | 一种氨基乙酸的合成方法 |
| CN113527220A (zh) * | 2021-07-26 | 2021-10-22 | 京博农化科技有限公司 | 一种脱硫丙硫菌唑异构体的合成方法 |
| CN114989079B (zh) * | 2022-06-21 | 2023-06-23 | 中国药科大学 | Ripk1激酶靶点抑制剂及其医药用途 |
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| ES2365869T3 (es) * | 2005-11-17 | 2011-10-11 | OSI Pharmaceuticals, LLC | COMPUESTOS BICÍCLICOS FUSIONADOS INHIBIDORES DE LA mTOR. |
| PE20070855A1 (es) | 2005-12-02 | 2007-10-14 | Bayer Pharmaceuticals Corp | Derivados de 4-amino-pirrolotriazina sustituida como inhibidores de quinasas |
| WO2007064931A2 (en) | 2005-12-02 | 2007-06-07 | Bayer Healthcare Llc | Substituted 4-amino-pyrrolotriazine derivatives useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
| GB2467670B (en) * | 2007-10-04 | 2012-08-01 | Intellikine Inc | Chemical entities and therapeutic uses thereof |
| US8765754B2 (en) | 2009-04-29 | 2014-07-01 | Locus Pharmaceuticals, Inc. | Pyrrolotriazine compounds |
| TW201107329A (en) * | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| IL266563B (en) | 2009-10-06 | 2022-09-01 | Millennium Pharm Inc | Heterocyclic compounds useful as pdk1 inhibitors |
| WO2011123493A1 (en) * | 2010-03-31 | 2011-10-06 | Bristol-Myers Squibb Company | Substituted pyrrolotriazines as protein kinase inhibitors |
| US9783573B2 (en) | 2012-09-18 | 2017-10-10 | Bristol-Myers Squibb Company | IAP antagonists |
| EP3054955B1 (en) | 2013-10-11 | 2018-05-30 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| EP3209665B1 (en) | 2014-10-22 | 2019-08-14 | Bristol-Myers Squibb Company | Substituted pyrrolotriazine amine compounds as pi3k inhibitors |
| ES2807785T3 (es) | 2014-10-22 | 2021-02-24 | Bristol Myers Squibb Co | Compuestos de heteroarilamina bicíclicos como inhibidores de pi3k |
| KR102483020B1 (ko) | 2016-03-28 | 2023-01-04 | 인사이트 코포레이션 | Tam 저해제로서의 피롤로트리아진 화합물 |
| WO2018017435A1 (en) | 2016-07-22 | 2018-01-25 | Accro Bioscience Inc. | Heteroaryl compounds as inhibitors of necrosis, composition and application thereof |
| EP3580220B1 (en) | 2017-02-13 | 2021-11-17 | Bristol-Myers Squibb Company | Aminotriazolopyridines as kinase inhibitors |
| DK3704118T3 (da) | 2017-10-30 | 2022-03-14 | Bristol Myers Squibb Co | Aminoimidazopyrazin som kinasehæmmere |
| EP3849968B1 (en) | 2018-09-13 | 2022-12-21 | Bristol-Myers Squibb Company | 1h-indazole carboxamides as receptor-interacting protein kinase 1 inhibitors (ripk1) |
| EP3849969B1 (en) | 2018-09-13 | 2023-04-19 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
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| CN112262139A (zh) | 2021-01-22 |
| AU2019211382A1 (en) | 2020-09-17 |
| JP2021511363A (ja) | 2021-05-06 |
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