JP2018520201A5 - - Google Patents
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- Publication number
- JP2018520201A5 JP2018520201A5 JP2018503142A JP2018503142A JP2018520201A5 JP 2018520201 A5 JP2018520201 A5 JP 2018520201A5 JP 2018503142 A JP2018503142 A JP 2018503142A JP 2018503142 A JP2018503142 A JP 2018503142A JP 2018520201 A5 JP2018520201 A5 JP 2018520201A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrrolo
- amino
- triazin
- amine
- 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.)
- Pending
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- -1 3-Fluoropyridin-4-yl Chemical group 0.000 claims 69
- 239000001257 hydrogen Substances 0.000 claims 67
- 229910052739 hydrogen Inorganic materials 0.000 claims 67
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 50
- 150000002431 hydrogen Chemical class 0.000 claims 42
- 235000005152 nicotinamide Nutrition 0.000 claims 40
- 239000011570 nicotinamide Substances 0.000 claims 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 19
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 15
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000011780 sodium chloride Substances 0.000 claims 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
- 125000003277 amino group Chemical compound 0.000 claims 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- RLNCTIUJEJXMBZ-UHFFFAOYSA-N pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound C1=NC=NN2C=C(C(=O)N)C=C21 RLNCTIUJEJXMBZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- CZUNBUWXQDQTQD-UHFFFAOYSA-N CCC1=CN2N=C(N=C(NC3=C(F)C=NC=C3)C2=C1)C1=NC(OC)=CC=C1 Chemical compound CCC1=CN2N=C(N=C(NC3=C(F)C=NC=C3)C2=C1)C1=NC(OC)=CC=C1 CZUNBUWXQDQTQD-UHFFFAOYSA-N 0.000 claims 2
- NXFOACUBQWRDMW-UHFFFAOYSA-N FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)F)=C(C=C2)CN1CCN(CC1)C)F Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)F)=C(C=C2)CN1CCN(CC1)C)F NXFOACUBQWRDMW-UHFFFAOYSA-N 0.000 claims 2
- QROKOTBWFZITJZ-UHFFFAOYSA-N N-pyridin-2-ylacetamide Chemical compound CC(=O)NC1=CC=CC=N1 QROKOTBWFZITJZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 230000003042 antagnostic Effects 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 125000005418 aryl aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 102000017186 transforming growth factor beta-activated receptor activity proteins Human genes 0.000 claims 2
- 108040009415 transforming growth factor beta-activated receptor activity proteins Proteins 0.000 claims 2
- SZBIFEUGEPUYLA-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-pyridin-3-ylmethanone Chemical compound C1CC(O)CCN1C(=O)C1=CC=CN=C1 SZBIFEUGEPUYLA-UHFFFAOYSA-N 0.000 claims 1
- MRYASQNSJAHEQV-UHFFFAOYSA-N 1$l^{2}-azolidin-2-one Chemical group O=C1CCC[N]1 MRYASQNSJAHEQV-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical compound [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 206010000880 Acute myeloid leukaemia Diseases 0.000 claims 1
- VIDIIZZGUMUDPL-UHFFFAOYSA-N C(C)(=O)NC1=NC=CC(=C1)NC1=NC(=NN2C1=C(C=C2)CN1CCN(CC1)CCO)C1=NC=CC=C1 Chemical compound C(C)(=O)NC1=NC=CC(=C1)NC1=NC(=NN2C1=C(C=C2)CN1CCN(CC1)CCO)C1=NC=CC=C1 VIDIIZZGUMUDPL-UHFFFAOYSA-N 0.000 claims 1
- NKELNVUWSOAPIZ-UHFFFAOYSA-N C(C)(=O)NC1=NC=CC(=C1)NC1=NC(=NN2C1=C(C=C2)CNCC(C)(C)O)C1=NC(=CC=C1)C(F)(F)F Chemical compound C(C)(=O)NC1=NC=CC(=C1)NC1=NC(=NN2C1=C(C=C2)CNCC(C)(C)O)C1=NC(=CC=C1)C(F)(F)F NKELNVUWSOAPIZ-UHFFFAOYSA-N 0.000 claims 1
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| EP4331679A3 (en) | 2017-06-21 | 2024-04-03 | Shy Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| US10653682B2 (en) * | 2017-10-26 | 2020-05-19 | Southern Research Institute | Oxadiazoles and thiadiazoles as TGF-β inhibitors |
| KR20210110316A (ko) | 2018-12-27 | 2021-09-07 | 넥시스 테라퓨틱스 인코포레이티드 | 암의 치료를 위한 tgf-베타 r1(alk5) 억제제로서의(피리딘-2-일)아민 유도체 |
| CN111825675B (zh) * | 2019-04-15 | 2023-08-01 | 武汉朗来科技发展有限公司 | Rock抑制剂及其制备方法和用途 |
| CN112694477B (zh) * | 2019-10-22 | 2024-02-06 | 四川科伦博泰生物医药股份有限公司 | 吡唑并环类化合物，包含其的药物组合物，其制备方法及其用途 |
| WO2021147699A1 (zh) * | 2020-01-21 | 2021-07-29 | 四川科伦博泰生物医药股份有限公司 | 吡啶并杂环类化合物、其制备方法及用途 |
| CN113620956B (zh) * | 2020-05-06 | 2023-06-13 | 赛诺哈勃药业（成都）有限公司 | 转化生长因子受体拮抗剂、其制备方法和应用 |
| WO2023196975A1 (en) * | 2022-04-08 | 2023-10-12 | Shy Therapeutics, Llc | Compounds that interact with ras superfamily proteins for treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| WO2024015497A1 (en) * | 2022-07-14 | 2024-01-18 | Biogen Ma Inc. | Tyrosine kinase 2 inhibitors and uses thereof |
| WO2024155842A1 (en) * | 2023-01-19 | 2024-07-25 | Skyhawk Therapeutics, Inc. | Compositions useful for modulating splicing |
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| JP2006521398A (ja) * | 2003-03-28 | 2006-09-21 | サイオス・インコーポレーテツド | ＴＧＦβの二−環式ピリミジン阻害剤 |
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