CA3088548A1 - Aminopyrrolotriazines as kinase inhibitors - Google Patents
Aminopyrrolotriazines as kinase inhibitors Download PDFInfo
- Publication number
- CA3088548A1 CA3088548A1 CA3088548A CA3088548A CA3088548A1 CA 3088548 A1 CA3088548 A1 CA 3088548A1 CA 3088548 A CA3088548 A CA 3088548A CA 3088548 A CA3088548 A CA 3088548A CA 3088548 A1 CA3088548 A1 CA 3088548A1
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- CA
- Canada
- Prior art keywords
- alkyl
- phenyl
- halo
- alkoxy
- haloalkyl
- 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.)
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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 abstract description 210
- 238000000034 method Methods 0.000 claims abstract description 65
- 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims abstract description 52
- 102100022501 Receptor-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims abstract description 51
- 125000005843 halogen group Chemical group 0.000 claims description 134
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 118
- 150000003839 salts Chemical class 0.000 claims description 101
- -1 -C(R5a)2- Chemical group 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 96
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 89
- 239000001257 hydrogen Substances 0.000 claims description 88
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 84
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 78
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 64
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 62
- 150000002431 hydrogen Chemical group 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 37
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000000335 thiazolyl group Chemical group 0.000 claims description 17
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 16
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 8
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 208000011231 Crohn disease Diseases 0.000 claims description 7
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 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
- 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
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- 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
- KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical compound C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino 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
- 239000008194 pharmaceutical composition Substances 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
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 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
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 206010019280 Heart failures Diseases 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000005495 pyridazyl group Chemical group 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 102000005403 Casein Kinases Human genes 0.000 claims 1
- 108010031425 Casein Kinases Proteins 0.000 claims 1
- 101100355584 Mus musculus Rad51 gene Proteins 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 26
- 230000017074 necrotic cell death Effects 0.000 abstract description 8
- 206010061218 Inflammation Diseases 0.000 abstract description 5
- 108091000080 Phosphotransferase Proteins 0.000 abstract description 5
- 230000004054 inflammatory process Effects 0.000 abstract description 5
- 102000020233 phosphotransferase Human genes 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 309
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 160
- 238000003556 assay Methods 0.000 description 111
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- 239000000203 mixture Substances 0.000 description 98
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 97
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 80
- 239000002585 base Substances 0.000 description 76
- 239000011541 reaction mixture Substances 0.000 description 76
- 210000004027 cell Anatomy 0.000 description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 64
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
- 239000000047 product Substances 0.000 description 55
- 230000027455 binding Effects 0.000 description 54
- 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 54
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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 41
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 28
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Classifications
-
- 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
-
- 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]
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (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 |
|---|---|
| CA3088548A1 true CA3088548A1 (en) | 2019-08-01 |
Family
ID=65363405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3088548A Pending CA3088548A1 (en) | 2018-01-26 | 2019-01-24 | Aminopyrrolotriazines as kinase inhibitors |
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=) |
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Families Citing this family (13)
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| MA47460A (fr) | 2017-02-13 | 2019-12-18 | Bristol Myers Squibb Co | Aminotriazolopyridines utilisées en tant qu'inhibiteurs de kinase |
| HUE058292T2 (hu) | 2017-10-30 | 2022-07-28 | Bristol Myers Squibb Co | Aminoimidazopiridazinok mint kináz inhibitorok |
| AU2019339355A1 (en) | 2018-09-13 | 2021-05-13 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| KR102906523B1 (ko) | 2018-09-13 | 2025-12-30 | 브리스톨-마이어스 스큅 컴퍼니 | 수용체-상호작용 단백질 키나제 1 (ripk1) 억제제로서의 1h-인다졸 카르복스아미드 |
| ES2969756T3 (es) | 2019-10-03 | 2024-05-22 | Bristol Myers Squibb Co | Indazol carboxamidas como inhibidores de cinasas |
| JPWO2021157596A1 (https=) * | 2020-02-07 | 2021-08-12 | ||
| 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 |
| JPWO2022172889A1 (https=) * | 2021-02-10 | 2022-08-18 | ||
| 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 |
| CN116574053B (zh) * | 2022-06-21 | 2026-04-14 | 中国药科大学 | Ripk1激酶靶点抑制剂及其医药用途 |
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| CA2627839C (en) | 2005-11-02 | 2014-08-19 | Bayer Healthcare Ag | Pyrrolo[2,1-f] [1,2,4] triazin-4-ylamines igf-1r kinase inhibitors for the treatment of cancer and other hyperproliferative diseases |
| EP2385053B1 (en) * | 2005-11-17 | 2013-10-02 | OSI Pharmaceuticals, Inc. | Intermediates for the preparation of fused bicyclic mTOR inhibitors |
| KR101461680B1 (ko) | 2005-12-02 | 2014-11-19 | 바이엘 헬스케어 엘엘씨 | 과다-증식성 장애 및 맥관형성과 관련된 질환의 치료에유용한 치환된 4-아미노-피롤로트리아진 유도체 |
| PE20070855A1 (es) | 2005-12-02 | 2007-10-14 | Bayer Pharmaceuticals Corp | Derivados de 4-amino-pirrolotriazina sustituida como inhibidores de quinasas |
| GB2467670B (en) * | 2007-10-04 | 2012-08-01 | Intellikine Inc | Chemical entities and therapeutic uses thereof |
| EP2424368B1 (en) | 2009-04-29 | 2014-12-31 | Locus Pharmaceuticals, Inc. | Pyrrolotriazine compounds |
| TW201107329A (en) | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| HRP20160967T1 (hr) | 2009-10-06 | 2016-10-07 | Millennium Pharmaceuticals, Inc. | Heterociklički spojevi korisni kao pdk1 inhibitori |
| CN102918045A (zh) | 2010-03-31 | 2013-02-06 | 百时美施贵宝公司 | 作为蛋白激酶抑制剂的取代的吡咯并三嗪 |
| WO2014047024A1 (en) | 2012-09-18 | 2014-03-27 | Bristol-Myers Squibb Company | Iap antagonists |
| WO2015054358A1 (en) | 2013-10-11 | 2015-04-16 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US10023576B2 (en) * | 2014-10-22 | 2018-07-17 | Bristol-Myers Squibb Company | Heteroaryl substituted pyrrolotriazine amine compounds as PI3K inhibitors |
| US10214537B2 (en) * | 2014-10-22 | 2019-02-26 | Bristol-Myers Squibb Company | Bicyclic heteroaryl amine compounds |
| MD3436461T2 (ro) | 2016-03-28 | 2024-05-31 | Incyte Corp | Compuși pirolotriazină ca inhibitori TAM |
| WO2018017435A1 (en) | 2016-07-22 | 2018-01-25 | Accro Bioscience Inc. | Heteroaryl compounds as inhibitors of necrosis, composition and application thereof |
| MA47460A (fr) | 2017-02-13 | 2019-12-18 | Bristol Myers Squibb Co | Aminotriazolopyridines utilisées en tant qu'inhibiteurs de kinase |
| HUE058292T2 (hu) | 2017-10-30 | 2022-07-28 | Bristol Myers Squibb Co | Aminoimidazopiridazinok mint kináz inhibitorok |
| AU2019339355A1 (en) | 2018-09-13 | 2021-05-13 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| KR102906523B1 (ko) | 2018-09-13 | 2025-12-30 | 브리스톨-마이어스 스큅 컴퍼니 | 수용체-상호작용 단백질 키나제 1 (ripk1) 억제제로서의 1h-인다졸 카르복스아미드 |
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2019
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- 2019-01-24 EA EA202091777A patent/EA202091777A1/ru unknown
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- 2019-01-24 AR ARP190100156A patent/AR114186A1/es unknown
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- 2019-01-24 SG SG11202007035YA patent/SG11202007035YA/en unknown
- 2019-01-24 WO PCT/US2019/014918 patent/WO2019147782A1/en not_active Ceased
- 2019-01-24 MX MX2020007531A patent/MX2020007531A/es unknown
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- 2019-01-25 TW TW108102873A patent/TW201940485A/zh unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| IL276269A (en) | 2020-09-30 |
| CN112262139A (zh) | 2021-01-22 |
| EA202091777A1 (ru) | 2020-10-14 |
| BR112020014516A2 (pt) | 2020-12-08 |
| AU2019211382B2 (en) | 2022-06-16 |
| KR20200115550A (ko) | 2020-10-07 |
| EP3743430A1 (en) | 2020-12-02 |
| AR114186A1 (es) | 2020-07-29 |
| MX2020007531A (es) | 2020-09-09 |
| CN112262139B (zh) | 2023-07-25 |
| EP3743430B1 (en) | 2023-08-02 |
| TW201940485A (zh) | 2019-10-16 |
| WO2019147782A1 (en) | 2019-08-01 |
| SG11202007035YA (en) | 2020-08-28 |
| JP7307734B2 (ja) | 2023-07-12 |
| JP2021511363A (ja) | 2021-05-06 |
| US20200347071A1 (en) | 2020-11-05 |
| KR102759231B1 (ko) | 2025-01-22 |
| AU2019211382A1 (en) | 2020-09-17 |
| US11618753B2 (en) | 2023-04-04 |
| ES2959399T3 (es) | 2024-02-26 |
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