JP2020520925A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020520925A5 JP2020520925A5 JP2019563609A JP2019563609A JP2020520925A5 JP 2020520925 A5 JP2020520925 A5 JP 2020520925A5 JP 2019563609 A JP2019563609 A JP 2019563609A JP 2019563609 A JP2019563609 A JP 2019563609A JP 2020520925 A5 JP2020520925 A5 JP 2020520925A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- diazepine
- compound according
- hexahydropyrazolo
- heterocyclyl
- 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
- LAODNOQGDMJAOS-UHFFFAOYSA-N 5-(6,6-dimethyl-5-oxo-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-3-yl)pyridine-3-carbonitrile Chemical compound CC1(C)CCCN2CCC(N2C1=O)c1cncc(c1)C#N LAODNOQGDMJAOS-UHFFFAOYSA-N 0.000 claims description 3
- QSPGMCGSCMXMNL-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-6,6-dimethyl-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-5-one Chemical compound CC1(C)CCCN2CCC(N2C1=O)c1ccc(F)c(F)c1 QSPGMCGSCMXMNL-UHFFFAOYSA-N 0.000 claims description 2
- STCDRGVTQJNRGW-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-6,6-dimethyl-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-5-one Chemical compound CC1(C)CCCN2CCC(N2C1=O)c1cc(F)cc(F)c1 STCDRGVTQJNRGW-UHFFFAOYSA-N 0.000 claims description 2
- QVEMDBXTQXHHAB-UHFFFAOYSA-N 3-(3-fluorophenyl)-6,6-dimethyl-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-5-one Chemical compound CC1(C)CCCN2CCC(N2C1=O)c1cccc(F)c1 QVEMDBXTQXHHAB-UHFFFAOYSA-N 0.000 claims description 2
- AGCGZWOZRAZHMZ-UHFFFAOYSA-N 3-(5-fluoropyridin-3-yl)-6,6-dimethyl-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-5-one Chemical compound CC1(C)CCCN2CCC(N2C1=O)c1cncc(F)c1 AGCGZWOZRAZHMZ-UHFFFAOYSA-N 0.000 claims description 2
- TTWMEHAWZMMXLK-UHFFFAOYSA-N 3-(5-fluoropyridin-3-yl)spiro[1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepine-6,1'-cyclopropane]-5-one Chemical compound FC1=CC(C2N3N(CC2)CCCC2(C3=O)CC2)=CN=C1 TTWMEHAWZMMXLK-UHFFFAOYSA-N 0.000 claims description 2
- MOFBCWRMOAILLK-UHFFFAOYSA-N 3-(6,6-dimethyl-5-oxo-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-3-yl)-5-fluorobenzonitrile Chemical compound CC1(C)CCCN2CCC(N2C1=O)c1cc(F)cc(c1)C#N MOFBCWRMOAILLK-UHFFFAOYSA-N 0.000 claims description 2
- NYPLMFCBARDUKW-UHFFFAOYSA-N 4-(6,6-dimethyl-5-oxo-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-3-yl)benzonitrile Chemical compound CC1(C)CCCN2CCC(N2C1=O)c1ccc(cc1)C#N NYPLMFCBARDUKW-UHFFFAOYSA-N 0.000 claims description 2
- UCYWTJSYPAWQBD-UHFFFAOYSA-N 5-[6-(difluoromethyl)-6-methyl-5-oxo-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-3-yl]pyridine-3-carbonitrile Chemical compound CC1(CCCN2CCC(N2C1=O)c1cncc(c1)C#N)C(F)F UCYWTJSYPAWQBD-UHFFFAOYSA-N 0.000 claims description 2
- WSAHDARCBJLIGV-UHFFFAOYSA-N 6,6-dimethyl-3-(5-methylpyrazin-2-yl)-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-5-one Chemical compound Cc1cnc(cn1)C1CCN2CCCC(C)(C)C(=O)N12 WSAHDARCBJLIGV-UHFFFAOYSA-N 0.000 claims description 2
- WTNUKYCIXBOCNF-UHFFFAOYSA-N 6-(difluoromethyl)-3-(5-fluoropyridin-3-yl)-6-methyl-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-5-one Chemical compound CC1(CCCN2CCC(N2C1=O)c1cncc(F)c1)C(F)F WTNUKYCIXBOCNF-UHFFFAOYSA-N 0.000 claims description 2
- PHTCEKYUIRGSET-UHFFFAOYSA-N 6-(difluoromethyl)-6-methyl-3-(5-methylpyrazin-2-yl)-1,2,3,7,8,9-hexahydropyrazolo[1,2-a]diazepin-5-one Chemical compound Cc1cnc(cn1)C1CCN2CCCC(C)(C(F)F)C(=O)N12 PHTCEKYUIRGSET-UHFFFAOYSA-N 0.000 claims description 2
- SFFOQVMDVZWHBQ-UHFFFAOYSA-N 7,7-difluoro-3-(5-fluoropyridin-3-yl)-6,6-dimethyl-2,3,8,9-tetrahydro-1H-pyrazolo[1,2-a]diazepin-5-one Chemical compound C1=C(C=C(C=N1)C1N2N(CC1)CCC(C(C2=O)(C)C)(F)F)F SFFOQVMDVZWHBQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 20
- -1 5-cyano-pyrid-3-yl Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrug Drugs 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- NBJDSMIOWPVWRW-UHFFFAOYSA-N 2h-oxazepin-5-one Chemical compound O=C1C=CNOC=C1 NBJDSMIOWPVWRW-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 101001113278 Arabidopsis thaliana Probable serine/threonine-protein kinase PBL9 Proteins 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 1
- 230000010799 Receptor Interactions Effects 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- ZGLDQGIONSGJCN-UHFFFAOYSA-N diazepin-5-one Chemical compound O=C1C=CN=NC=C1 ZGLDQGIONSGJCN-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- LAODNOQGDMJAOS-AWEZNQCLSA-N CC(C)(CCCN(CC1)N2[C@@H]1c1cncc(C#N)c1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c1cncc(C#N)c1)C2=O LAODNOQGDMJAOS-AWEZNQCLSA-N 0.000 description 2
- LAODNOQGDMJAOS-CQSZACIVSA-N CC(C)(CCCN(CC1)N2[C@H]1c1cc(C#N)cnc1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c1cc(C#N)cnc1)C2=O LAODNOQGDMJAOS-CQSZACIVSA-N 0.000 description 2
- DXFSFXLDGYOUKI-UHFFFAOYSA-N CC(CC#N)(CCCN(CC1)N2C1c1ncc(C)nc1)C2=O Chemical compound CC(CC#N)(CCCN(CC1)N2C1c1ncc(C)nc1)C2=O DXFSFXLDGYOUKI-UHFFFAOYSA-N 0.000 description 2
- 0 *C(CC*1***C2(*)*)N1C2=O Chemical compound *C(CC*1***C2(*)*)N1C2=O 0.000 description 1
- SFFOQVMDVZWHBQ-LBPRGKRZSA-N CC(C)(C(CCN(CC1)N2[C@@H]1c1cc(F)cnc1)(F)F)C2=O Chemical compound CC(C)(C(CCN(CC1)N2[C@@H]1c1cc(F)cnc1)(F)F)C2=O SFFOQVMDVZWHBQ-LBPRGKRZSA-N 0.000 description 1
- SFFOQVMDVZWHBQ-GFCCVEGCSA-N CC(C)(C(CCN(CC1)N2[C@H]1c1cc(F)cnc1)(F)F)C2=O Chemical compound CC(C)(C(CCN(CC1)N2[C@H]1c1cc(F)cnc1)(F)F)C2=O SFFOQVMDVZWHBQ-GFCCVEGCSA-N 0.000 description 1
- QSPGMCGSCMXMNL-AWEZNQCLSA-N CC(C)(CCCN(CC1)N2[C@@H]1c(cc1)cc(F)c1F)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c(cc1)cc(F)c1F)C2=O QSPGMCGSCMXMNL-AWEZNQCLSA-N 0.000 description 1
- NYPLMFCBARDUKW-HNNXBMFYSA-N CC(C)(CCCN(CC1)N2[C@@H]1c(cc1)ccc1C#N)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c(cc1)ccc1C#N)C2=O NYPLMFCBARDUKW-HNNXBMFYSA-N 0.000 description 1
- MOFBCWRMOAILLK-HNNXBMFYSA-N CC(C)(CCCN(CC1)N2[C@@H]1c1cc(C#N)cc(F)c1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c1cc(C#N)cc(F)c1)C2=O MOFBCWRMOAILLK-HNNXBMFYSA-N 0.000 description 1
- STCDRGVTQJNRGW-AWEZNQCLSA-N CC(C)(CCCN(CC1)N2[C@@H]1c1cc(F)cc(F)c1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c1cc(F)cc(F)c1)C2=O STCDRGVTQJNRGW-AWEZNQCLSA-N 0.000 description 1
- QVEMDBXTQXHHAB-AWEZNQCLSA-N CC(C)(CCCN(CC1)N2[C@@H]1c1cc(F)ccc1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c1cc(F)ccc1)C2=O QVEMDBXTQXHHAB-AWEZNQCLSA-N 0.000 description 1
- AGCGZWOZRAZHMZ-ZDUSSCGKSA-N CC(C)(CCCN(CC1)N2[C@@H]1c1cncc(F)c1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c1cncc(F)c1)C2=O AGCGZWOZRAZHMZ-ZDUSSCGKSA-N 0.000 description 1
- WSAHDARCBJLIGV-ZDUSSCGKSA-N CC(C)(CCCN(CC1)N2[C@@H]1c1ncc(C)nc1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@@H]1c1ncc(C)nc1)C2=O WSAHDARCBJLIGV-ZDUSSCGKSA-N 0.000 description 1
- QSPGMCGSCMXMNL-CQSZACIVSA-N CC(C)(CCCN(CC1)N2[C@H]1c(cc1)cc(F)c1F)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c(cc1)cc(F)c1F)C2=O QSPGMCGSCMXMNL-CQSZACIVSA-N 0.000 description 1
- NYPLMFCBARDUKW-OAHLLOKOSA-N CC(C)(CCCN(CC1)N2[C@H]1c(cc1)ccc1C#N)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c(cc1)ccc1C#N)C2=O NYPLMFCBARDUKW-OAHLLOKOSA-N 0.000 description 1
- MOFBCWRMOAILLK-OAHLLOKOSA-N CC(C)(CCCN(CC1)N2[C@H]1c1cc(C#N)cc(F)c1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c1cc(C#N)cc(F)c1)C2=O MOFBCWRMOAILLK-OAHLLOKOSA-N 0.000 description 1
- STCDRGVTQJNRGW-CQSZACIVSA-N CC(C)(CCCN(CC1)N2[C@H]1c1cc(F)cc(F)c1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c1cc(F)cc(F)c1)C2=O STCDRGVTQJNRGW-CQSZACIVSA-N 0.000 description 1
- QVEMDBXTQXHHAB-CQSZACIVSA-N CC(C)(CCCN(CC1)N2[C@H]1c1cc(F)ccc1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c1cc(F)ccc1)C2=O QVEMDBXTQXHHAB-CQSZACIVSA-N 0.000 description 1
- AGCGZWOZRAZHMZ-CYBMUJFWSA-N CC(C)(CCCN(CC1)N2[C@H]1c1cc(F)cnc1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c1cc(F)cnc1)C2=O AGCGZWOZRAZHMZ-CYBMUJFWSA-N 0.000 description 1
- WSAHDARCBJLIGV-CYBMUJFWSA-N CC(C)(CCCN(CC1)N2[C@H]1c1ncc(C)nc1)C2=O Chemical compound CC(C)(CCCN(CC1)N2[C@H]1c1ncc(C)nc1)C2=O WSAHDARCBJLIGV-CYBMUJFWSA-N 0.000 description 1
- SNPHPCKNSGKBHO-UHFFFAOYSA-N CC(CC#N)(CCCN(CC1)N2C1c1cncc(F)c1)C2=O Chemical compound CC(CC#N)(CCCN(CC1)N2C1c1cncc(F)c1)C2=O SNPHPCKNSGKBHO-UHFFFAOYSA-N 0.000 description 1
- SNPHPCKNSGKBHO-LBAUFKAWSA-N CC(CC#N)(CCCN(CC1)N2[C@@H]1c1cc(F)cnc1)C2=O Chemical compound CC(CC#N)(CCCN(CC1)N2[C@@H]1c1cc(F)cnc1)C2=O SNPHPCKNSGKBHO-LBAUFKAWSA-N 0.000 description 1
- DXFSFXLDGYOUKI-LBAUFKAWSA-N CC(CC#N)(CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)C2=O Chemical compound CC(CC#N)(CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)C2=O DXFSFXLDGYOUKI-LBAUFKAWSA-N 0.000 description 1
- SNPHPCKNSGKBHO-IURRXHLWSA-N CC(CC#N)(CCCN(CC1)N2[C@H]1c1cncc(F)c1)C2=O Chemical compound CC(CC#N)(CCCN(CC1)N2[C@H]1c1cncc(F)c1)C2=O SNPHPCKNSGKBHO-IURRXHLWSA-N 0.000 description 1
- YCZGFTOSQSFYQI-UHFFFAOYSA-N CC(CCCC(CC1)N2C1c1cncc(C#N)c1)(C(F)F)C2=O Chemical compound CC(CCCC(CC1)N2C1c1cncc(C#N)c1)(C(F)F)C2=O YCZGFTOSQSFYQI-UHFFFAOYSA-N 0.000 description 1
- UCYWTJSYPAWQBD-KNVGNIICSA-N CC(CCCN(CC1)N2[C@@H]1c1cc(C#N)cnc1)(C(F)F)C2=O Chemical compound CC(CCCN(CC1)N2[C@@H]1c1cc(C#N)cnc1)(C(F)F)C2=O UCYWTJSYPAWQBD-KNVGNIICSA-N 0.000 description 1
- WTNUKYCIXBOCNF-SFVWDYPZSA-N CC(CCCN(CC1)N2[C@@H]1c1cc(F)cnc1)(C(F)F)C2=O Chemical compound CC(CCCN(CC1)N2[C@@H]1c1cc(F)cnc1)(C(F)F)C2=O WTNUKYCIXBOCNF-SFVWDYPZSA-N 0.000 description 1
- PHTCEKYUIRGSET-SFVWDYPZSA-N CC(CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)(C(F)F)C2=O Chemical compound CC(CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)(C(F)F)C2=O PHTCEKYUIRGSET-SFVWDYPZSA-N 0.000 description 1
- WTNUKYCIXBOCNF-KEKZHRQWSA-N CC(CCCN(CC1)N2[C@H]1c1cc(F)cnc1)(C(F)F)C2=O Chemical compound CC(CCCN(CC1)N2[C@H]1c1cc(F)cnc1)(C(F)F)C2=O WTNUKYCIXBOCNF-KEKZHRQWSA-N 0.000 description 1
- PHTCEKYUIRGSET-KEKZHRQWSA-N CC(CCCN(CC1)N2[C@H]1c1cnc(C)cn1)(C(F)F)C2=O Chemical compound CC(CCCN(CC1)N2[C@H]1c1cnc(C)cn1)(C(F)F)C2=O PHTCEKYUIRGSET-KEKZHRQWSA-N 0.000 description 1
- UCYWTJSYPAWQBD-JBZHPUCOSA-N CC(CCCN(CC1)N2[C@H]1c1cncc(C#N)c1)(C(F)F)C2=O Chemical compound CC(CCCN(CC1)N2[C@H]1c1cncc(C#N)c1)(C(F)F)C2=O UCYWTJSYPAWQBD-JBZHPUCOSA-N 0.000 description 1
- YCZGFTOSQSFYQI-CBVZESEGSA-N CC(CCC[C@@H](CC1)N2[C@@H]1c1cc(C#N)cnc1)(C(F)F)C2=O Chemical compound CC(CCC[C@@H](CC1)N2[C@@H]1c1cc(C#N)cnc1)(C(F)F)C2=O YCZGFTOSQSFYQI-CBVZESEGSA-N 0.000 description 1
- YCZGFTOSQSFYQI-RFOFMGPBSA-N CC(CCC[C@@H](CC1)N2[C@H]1c1cc(C#N)cnc1)(C(F)F)C2=O Chemical compound CC(CCC[C@@H](CC1)N2[C@H]1c1cc(C#N)cnc1)(C(F)F)C2=O YCZGFTOSQSFYQI-RFOFMGPBSA-N 0.000 description 1
- YCZGFTOSQSFYQI-LICQEQMYSA-N CC(CCC[C@H](CC1)N2[C@@H]1c1cc(C#N)cnc1)(C(F)F)C2=O Chemical compound CC(CCC[C@H](CC1)N2[C@@H]1c1cc(C#N)cnc1)(C(F)F)C2=O YCZGFTOSQSFYQI-LICQEQMYSA-N 0.000 description 1
- YCZGFTOSQSFYQI-LJNCCCJHSA-N CC(CCC[C@H](CC1)N2[C@H]1c1cncc(C#N)c1)(C(F)F)C2=O Chemical compound CC(CCC[C@H](CC1)N2[C@H]1c1cncc(C#N)c1)(C(F)F)C2=O YCZGFTOSQSFYQI-LJNCCCJHSA-N 0.000 description 1
- SLVBMCAJFZEVPG-UHFFFAOYSA-N CC1(C)OCCN(CCC2c3cc(F)cnc3)N2C1=O Chemical compound CC1(C)OCCN(CCC2c3cc(F)cnc3)N2C1=O SLVBMCAJFZEVPG-UHFFFAOYSA-N 0.000 description 1
- SLVBMCAJFZEVPG-GFCCVEGCSA-N CC1(C)OCCN(CC[C@@H]2c3cncc(F)c3)N2C1=O Chemical compound CC1(C)OCCN(CC[C@@H]2c3cncc(F)c3)N2C1=O SLVBMCAJFZEVPG-GFCCVEGCSA-N 0.000 description 1
- SLVBMCAJFZEVPG-LBPRGKRZSA-N CC1(C)OCCN(CC[C@H]2c3cncc(F)c3)N2C1=O Chemical compound CC1(C)OCCN(CC[C@H]2c3cncc(F)c3)N2C1=O SLVBMCAJFZEVPG-LBPRGKRZSA-N 0.000 description 1
- HOQNVOWDNPNTOE-UHFFFAOYSA-N CCC(C)(COCC(CC1)N2C1c1cc(F)ccc1)C2=O Chemical compound CCC(C)(COCC(CC1)N2C1c1cc(F)ccc1)C2=O HOQNVOWDNPNTOE-UHFFFAOYSA-N 0.000 description 1
- HOQNVOWDNPNTOE-CKDQBVIESA-N CCC(C)(COC[C@@H](CC1)N2[C@@H]1c1cc(F)ccc1)C2=O Chemical compound CCC(C)(COC[C@@H](CC1)N2[C@@H]1c1cc(F)ccc1)C2=O HOQNVOWDNPNTOE-CKDQBVIESA-N 0.000 description 1
- HOQNVOWDNPNTOE-BLBXNVQISA-N CCC(C)(COC[C@@H](CC1)N2[C@H]1c1cc(F)ccc1)C2=O Chemical compound CCC(C)(COC[C@@H](CC1)N2[C@H]1c1cc(F)ccc1)C2=O HOQNVOWDNPNTOE-BLBXNVQISA-N 0.000 description 1
- HOQNVOWDNPNTOE-GIIGEWEBSA-N CCC(C)(COC[C@H](CC1)N2[C@@H]1c1cccc(F)c1)C2=O Chemical compound CCC(C)(COC[C@H](CC1)N2[C@@H]1c1cccc(F)c1)C2=O HOQNVOWDNPNTOE-GIIGEWEBSA-N 0.000 description 1
- HOQNVOWDNPNTOE-BTPDTDQASA-N CCC(C)(COC[C@H](CC1)N2[C@H]1c1cccc(F)c1)C2=O Chemical compound CCC(C)(COC[C@H](CC1)N2[C@H]1c1cccc(F)c1)C2=O HOQNVOWDNPNTOE-BTPDTDQASA-N 0.000 description 1
- WVAFSAZVQMSFNA-UHFFFAOYSA-N CCC(CCCN(CC1)N2C1c1cnc(C)cn1)(C(F)F)C2=O Chemical compound CCC(CCCN(CC1)N2C1c1cnc(C)cn1)(C(F)F)C2=O WVAFSAZVQMSFNA-UHFFFAOYSA-N 0.000 description 1
- WVAFSAZVQMSFNA-KNVGNIICSA-N CCC(CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)(C(F)F)C2=O Chemical compound CCC(CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)(C(F)F)C2=O WVAFSAZVQMSFNA-KNVGNIICSA-N 0.000 description 1
- WVAFSAZVQMSFNA-JBZHPUCOSA-N CCC(CCCN(CC1)N2[C@H]1c1cnc(C)cn1)(C(F)F)C2=O Chemical compound CCC(CCCN(CC1)N2[C@H]1c1cnc(C)cn1)(C(F)F)C2=O WVAFSAZVQMSFNA-JBZHPUCOSA-N 0.000 description 1
- WVAFSAZVQMSFNA-XJKSGUPXSA-N CC[C@@](CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)(C(F)F)C2=O Chemical compound CC[C@@](CCCN(CC1)N2[C@@H]1c1cnc(C)cn1)(C(F)F)C2=O WVAFSAZVQMSFNA-XJKSGUPXSA-N 0.000 description 1
- WVAFSAZVQMSFNA-CZUORRHYSA-N CC[C@@](CCCN(CC1)N2[C@H]1c1cnc(C)cn1)(C(F)F)C2=O Chemical compound CC[C@@](CCCN(CC1)N2[C@H]1c1cnc(C)cn1)(C(F)F)C2=O WVAFSAZVQMSFNA-CZUORRHYSA-N 0.000 description 1
- TTWMEHAWZMMXLK-ZDUSSCGKSA-N O=C1N([C@@H](CC2)c3cc(F)cnc3)N2CCCC11CC1 Chemical compound O=C1N([C@@H](CC2)c3cc(F)cnc3)N2CCCC11CC1 TTWMEHAWZMMXLK-ZDUSSCGKSA-N 0.000 description 1
- TTWMEHAWZMMXLK-CYBMUJFWSA-N O=C1N([C@H](CC2)c3cc(F)cnc3)N2CCCC11CC1 Chemical compound O=C1N([C@H](CC2)c3cc(F)cnc3)N2CCCC11CC1 TTWMEHAWZMMXLK-CYBMUJFWSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022141824A JP2022174180A (ja) | 2017-05-17 | 2022-09-07 | 化合物、組成物および方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762507682P | 2017-05-17 | 2017-05-17 | |
| US62/507,682 | 2017-05-17 | ||
| PCT/US2018/033269 WO2018213634A1 (en) | 2017-05-17 | 2018-05-17 | Compounds, compositions and methods |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022141824A Division JP2022174180A (ja) | 2017-05-17 | 2022-09-07 | 化合物、組成物および方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020520925A JP2020520925A (ja) | 2020-07-16 |
| JP2020520925A5 true JP2020520925A5 (https=) | 2021-07-26 |
| JP7140781B2 JP7140781B2 (ja) | 2022-09-21 |
Family
ID=64274734
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019563609A Active JP7140781B2 (ja) | 2017-05-17 | 2018-05-17 | 化合物、組成物および方法 |
| JP2022141824A Withdrawn JP2022174180A (ja) | 2017-05-17 | 2022-09-07 | 化合物、組成物および方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022141824A Withdrawn JP2022174180A (ja) | 2017-05-17 | 2022-09-07 | 化合物、組成物および方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US11174262B2 (https=) |
| EP (1) | EP3625234B1 (https=) |
| JP (2) | JP7140781B2 (https=) |
| KR (1) | KR102637541B1 (https=) |
| CN (1) | CN110914275A (https=) |
| AU (2) | AU2018269745C1 (https=) |
| BR (1) | BR112019023979A2 (https=) |
| CA (1) | CA3063938A1 (https=) |
| IL (1) | IL270505B2 (https=) |
| MX (1) | MX2019013642A (https=) |
| WO (1) | WO2018213634A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7208137B2 (ja) | 2016-12-09 | 2023-01-18 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| JP7140781B2 (ja) * | 2017-05-17 | 2022-09-21 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| US20220023266A1 (en) | 2018-12-07 | 2022-01-27 | Neurocrine Biosciences, Inc. | Crf1 receptor antagonist, pharmaceutical formulations and solid forms thereof for the treatment of congenital adrenal hyperplasia |
| US20240024330A1 (en) * | 2020-08-26 | 2024-01-25 | Neurocrine Biosciences, Inc. | Crf receptor antagonists and methods of use |
| EP4422621A4 (en) * | 2021-10-27 | 2025-08-27 | Merck Sharp & Dohme Llc | SPIROTRICYCLIC RIPK1 INHIBITORS AND METHODS OF USE THEREOF |
| WO2025045281A2 (zh) * | 2023-08-31 | 2025-03-06 | 杭州百诚医药科技股份有限公司 | 苯并氮杂䓬酮类化合物及其用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4290952A (en) * | 1980-06-23 | 1981-09-22 | American Home Products Corporation | Aryl-1-mercaptoalkanoylproline and homoproline derivatives |
| US4320057A (en) * | 1980-06-23 | 1982-03-16 | American Home Products Corporation | Aryl--pyrrolo--thiazepin--diones and aryl--piperidino--thiazepin--diones |
| BRPI0506883A (pt) | 2004-01-16 | 2007-05-29 | Univ Michigan | miméticos de smac conformacionalmente comprimidos e seus usos |
| CA2573644A1 (en) | 2004-07-12 | 2006-02-16 | Idun Pharmaceuticals, Inc. | Tetrapeptide analogs |
| US7989441B2 (en) | 2005-06-08 | 2011-08-02 | Novartis Ag | Organic compounds |
| TWI370130B (en) | 2005-11-24 | 2012-08-11 | Eisai R&D Man Co Ltd | Two cyclic cinnamide compound |
| MX2009000824A (es) * | 2006-07-24 | 2009-02-04 | Tetralogic Pharmaceuticals Cor | Antagonistas dimericos de las proteinas inhibidoras de la apoptosis. |
| CN108440571B (zh) | 2012-10-22 | 2022-11-04 | 希望之城 | Etp衍生物 |
| US20150023913A1 (en) | 2013-07-02 | 2015-01-22 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| SG11201704764PA (en) * | 2014-12-11 | 2017-07-28 | Harvard College | Inhibitors of cellular necrosis and related methods |
| EP3224245B1 (en) * | 2014-12-24 | 2018-09-12 | National Institute Of Biological Sciences, Beijing | Necrosis inhibitors |
| JP7140781B2 (ja) * | 2017-05-17 | 2022-09-21 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
-
2018
- 2018-05-17 JP JP2019563609A patent/JP7140781B2/ja active Active
- 2018-05-17 CN CN201880047315.8A patent/CN110914275A/zh active Pending
- 2018-05-17 EP EP18803112.4A patent/EP3625234B1/en active Active
- 2018-05-17 KR KR1020197036801A patent/KR102637541B1/ko active Active
- 2018-05-17 IL IL270505A patent/IL270505B2/en unknown
- 2018-05-17 AU AU2018269745A patent/AU2018269745C1/en not_active Ceased
- 2018-05-17 MX MX2019013642A patent/MX2019013642A/es unknown
- 2018-05-17 BR BR112019023979A patent/BR112019023979A2/pt active Search and Examination
- 2018-05-17 WO PCT/US2018/033269 patent/WO2018213634A1/en not_active Ceased
- 2018-05-17 CA CA3063938A patent/CA3063938A1/en active Pending
-
2019
- 2019-11-14 US US16/683,970 patent/US11174262B2/en active Active
-
2021
- 2021-10-05 US US17/494,336 patent/US11851433B2/en active Active
-
2022
- 2022-04-14 AU AU2022202524A patent/AU2022202524B2/en not_active Ceased
- 2022-09-07 JP JP2022141824A patent/JP2022174180A/ja not_active Withdrawn