JP2021501179A5 - - Google Patents
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- Publication number
- JP2021501179A5 JP2021501179A5 JP2020524156A JP2020524156A JP2021501179A5 JP 2021501179 A5 JP2021501179 A5 JP 2021501179A5 JP 2020524156 A JP2020524156 A JP 2020524156A JP 2020524156 A JP2020524156 A JP 2020524156A JP 2021501179 A5 JP2021501179 A5 JP 2021501179A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridazine
- methyl
- carboxamide
- phenyl
- imidazole
- 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.)
- Granted
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 480
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 268
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 221
- -1 2-cyclopropyl- Chemical group 0.000 claims 165
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 107
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 94
- 235000005152 nicotinamide Nutrition 0.000 claims 81
- 239000011570 nicotinamide Substances 0.000 claims 81
- 125000000217 alkyl group Chemical group 0.000 claims 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 61
- 150000002460 imidazoles Chemical class 0.000 claims 57
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 45
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 229910052799 carbon Inorganic materials 0.000 claims 28
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 26
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 150000003857 carboxamides Chemical class 0.000 claims 18
- YNJXVWIPWJKJJD-UHFFFAOYSA-N 2-methoxypyridine-3-carboxamide Chemical compound COC1=NC=CC=C1C(N)=O YNJXVWIPWJKJJD-UHFFFAOYSA-N 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 15
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 claims 14
- GAWNOZOKPKBYKC-UHFFFAOYSA-N 2-methoxy-6-methylpyridine-3-carboxamide Chemical compound COC1=NC(C)=CC=C1C(N)=O GAWNOZOKPKBYKC-UHFFFAOYSA-N 0.000 claims 13
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 11
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000005345 deuteroalkyl group Chemical group 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- IQCHZCYHDCDSFI-UHFFFAOYSA-N 2-cyano-2-methylpropanamide Chemical compound N#CC(C)(C)C(N)=O IQCHZCYHDCDSFI-UHFFFAOYSA-N 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- MTEZLAATISORQK-UHFFFAOYSA-N 2-methoxyacetamide Chemical compound COCC(N)=O MTEZLAATISORQK-UHFFFAOYSA-N 0.000 claims 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- VRZZMRYGHFNKEN-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)acetamide Chemical compound CN1CCN(CC(N)=O)CC1 VRZZMRYGHFNKEN-UHFFFAOYSA-N 0.000 claims 2
- CBBFWSMELCDMPZ-UHFFFAOYSA-N 2-(methylamino)acetamide Chemical compound CNCC(N)=O CBBFWSMELCDMPZ-UHFFFAOYSA-N 0.000 claims 2
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- RPLWYOLCHGTNSX-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CN1C=NC=C1 RPLWYOLCHGTNSX-UHFFFAOYSA-N 0.000 claims 1
- LOHJXVMUYVDWOW-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]imidazole Chemical compound C1=CC(F)=CC=C1CN1C=NC=C1 LOHJXVMUYVDWOW-UHFFFAOYSA-N 0.000 claims 1
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 claims 1
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
- LBTUTDYXOOUODJ-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetamide Chemical compound NC(=O)CN1CCCC1 LBTUTDYXOOUODJ-UHFFFAOYSA-N 0.000 claims 1
- 102000005403 Casein Kinases Human genes 0.000 claims 1
- 108010031425 Casein Kinases Proteins 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 102100022501 Receptor-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- DMYLUKNFEYWGCH-UHFFFAOYSA-N pyridazine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=N1 DMYLUKNFEYWGCH-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 0 CC(*)(*)C(Nc(nc1cc2)c(*)[n]1nc2C1=C(*)C(I**)=C(*)**1)=O Chemical compound CC(*)(*)C(Nc(nc1cc2)c(*)[n]1nc2C1=C(*)C(I**)=C(*)**1)=O 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762578607P | 2017-10-30 | 2017-10-30 | |
| US62/578,607 | 2017-10-30 | ||
| US201862626853P | 2018-02-06 | 2018-02-06 | |
| US62/626,853 | 2018-02-06 | ||
| PCT/US2018/057968 WO2019089442A1 (en) | 2017-10-30 | 2018-10-29 | Aminoimidazopyridines as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021501179A JP2021501179A (ja) | 2021-01-14 |
| JP2021501179A5 true JP2021501179A5 (https=) | 2021-12-09 |
| JP7228586B2 JP7228586B2 (ja) | 2023-02-24 |
Family
ID=64332173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020524156A Active JP7228586B2 (ja) | 2017-10-30 | 2018-10-29 | キナーゼ阻害剤としてのアミノイミダゾピリダジン |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US11440913B2 (https=) |
| EP (1) | EP3704118B1 (https=) |
| JP (1) | JP7228586B2 (https=) |
| KR (1) | KR102662197B1 (https=) |
| CN (1) | CN111566103B (https=) |
| AU (1) | AU2018361249B2 (https=) |
| BR (1) | BR112020007557A2 (https=) |
| CA (1) | CA3080402A1 (https=) |
| CY (1) | CY1124984T1 (https=) |
| DK (1) | DK3704118T3 (https=) |
| ES (1) | ES2905948T3 (https=) |
| HR (1) | HRP20220297T1 (https=) |
| HU (1) | HUE058292T2 (https=) |
| IL (1) | IL274207B2 (https=) |
| LT (1) | LT3704118T (https=) |
| MX (1) | MX2020003706A (https=) |
| PL (1) | PL3704118T3 (https=) |
| PT (1) | PT3704118T (https=) |
| RS (1) | RS62974B1 (https=) |
| SG (1) | SG11202003824PA (https=) |
| SI (1) | SI3704118T1 (https=) |
| SM (1) | SMT202200087T1 (https=) |
| WO (1) | WO2019089442A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3580220B1 (en) | 2017-02-13 | 2021-11-17 | Bristol-Myers Squibb Company | Aminotriazolopyridines as kinase inhibitors |
| SG11202007035YA (en) | 2018-01-26 | 2020-08-28 | Bristol Myers Squibb Co | Aminopyrrolotriazines 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) |
| EP3849969B1 (en) | 2018-09-13 | 2023-04-19 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| GB201905721D0 (en) | 2019-04-24 | 2019-06-05 | Univ Dundee | Compounds |
| WO2021067654A1 (en) * | 2019-10-03 | 2021-04-08 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| WO2021168521A1 (en) * | 2020-02-27 | 2021-09-02 | Anaxis Pharma Pty Ltd | Inhibitors of necroptosis |
| CN114262322B (zh) * | 2020-09-16 | 2026-01-06 | 中国科学院上海有机化学研究所 | 一类细胞程序性坏死抑制剂及其制备方法和用途 |
| AU2021362678A1 (en) * | 2020-10-13 | 2023-05-04 | The Johns Hopkins University | SUBSTITUTED 4-([1,2,4]TRIAZOLO[1,5-a]PYRIDIN-6-YL)THIOPHENE-2-CARBOXAMIDE DERIVATIVES AND USE THEREOF |
| AR123793A1 (es) * | 2020-10-19 | 2023-01-11 | Bristol Myers Squibb Co | Compuestos de triazolopiridinilo como inhibidores de quinasas |
| CN120530112A (zh) * | 2022-12-30 | 2025-08-22 | 广州市联瑞制药有限公司 | 双环类化合物及其制备方法和应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20070978A1 (es) * | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
| AU2008343813B2 (en) * | 2007-12-19 | 2012-04-12 | Amgen Inc. | Inhibitors of PI3 kinase |
| CA2750517A1 (en) * | 2009-02-04 | 2010-08-12 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2865671B1 (en) | 2012-06-22 | 2017-11-01 | Sumitomo Chemical Company, Ltd | Fused heterocyclic compound |
| US9783573B2 (en) | 2012-09-18 | 2017-10-10 | Bristol-Myers Squibb Company | IAP antagonists |
| ES2749467T3 (es) | 2012-11-20 | 2020-03-20 | Biogen Ma Inc | Agentes moduladores de S1p y/o ATX |
| WO2014144455A1 (en) | 2013-03-15 | 2014-09-18 | Epizyme, Inc. | 1 -phenoxy-3-(alkylamino)-propan-2-ol derivatives as carm1 inhibitors and uses thereof |
| HK1219737A1 (zh) | 2013-06-10 | 2017-04-13 | Bayer Pharma Aktiengesellschaft | 用於治疗癌症的新化合物 |
| CN106573006A (zh) | 2014-08-21 | 2017-04-19 | 葛兰素史密斯克莱知识产权发展有限公司 | 作为药物的rip1激酶抑制剂杂环酰胺 |
| KR102530515B1 (ko) | 2016-05-05 | 2023-05-09 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 치환된 이미다조[1,2-b]피리다진, 치환된 이미다조[1,5-b]피리다진, 관련 화합물, 및 의학적 장애의 치료에서의 그의 용도 |
| 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 |
| SG11202007035YA (en) | 2018-01-26 | 2020-08-28 | Bristol Myers Squibb Co | Aminopyrrolotriazines 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) |
| EP3849969B1 (en) | 2018-09-13 | 2023-04-19 | Bristol-Myers Squibb Company | Indazole carboxamides as kinase inhibitors |
| EP3877371A4 (en) * | 2018-11-07 | 2022-07-27 | Dana-Farber Cancer Institute, Inc. | IMIDAZOPYRIDINE DERIVATIVES AND AZA-IMIDAZOPYRIDINE DERIVATIVES AS JANUS KINASE 2 INHIBITORS AND USES THEREOF |
-
2018
- 2018-10-29 DK DK18804177.6T patent/DK3704118T3/da active
- 2018-10-29 SG SG11202003824PA patent/SG11202003824PA/en unknown
- 2018-10-29 AU AU2018361249A patent/AU2018361249B2/en not_active Ceased
- 2018-10-29 ES ES18804177T patent/ES2905948T3/es active Active
- 2018-10-29 MX MX2020003706A patent/MX2020003706A/es unknown
- 2018-10-29 HR HRP20220297TT patent/HRP20220297T1/hr unknown
- 2018-10-29 JP JP2020524156A patent/JP7228586B2/ja active Active
- 2018-10-29 SI SI201830556T patent/SI3704118T1/sl unknown
- 2018-10-29 EP EP18804177.6A patent/EP3704118B1/en active Active
- 2018-10-29 BR BR112020007557-4A patent/BR112020007557A2/pt not_active IP Right Cessation
- 2018-10-29 CA CA3080402A patent/CA3080402A1/en active Pending
- 2018-10-29 PL PL18804177T patent/PL3704118T3/pl unknown
- 2018-10-29 HU HUE18804177A patent/HUE058292T2/hu unknown
- 2018-10-29 WO PCT/US2018/057968 patent/WO2019089442A1/en not_active Ceased
- 2018-10-29 PT PT188041776T patent/PT3704118T/pt unknown
- 2018-10-29 RS RS20220215A patent/RS62974B1/sr unknown
- 2018-10-29 CN CN201880084047.7A patent/CN111566103B/zh active Active
- 2018-10-29 SM SM20220087T patent/SMT202200087T1/it unknown
- 2018-10-29 KR KR1020207015195A patent/KR102662197B1/ko active Active
- 2018-10-29 US US16/758,892 patent/US11440913B2/en active Active
- 2018-10-29 LT LTEPPCT/US2018/057968T patent/LT3704118T/lt unknown
-
2020
- 2020-04-24 IL IL274207A patent/IL274207B2/en unknown
-
2022
- 2022-03-08 CY CY20221100117T patent/CY1124984T1/el unknown
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