JPWO2019238633A5 - - Google Patents
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- Publication number
- JPWO2019238633A5 JPWO2019238633A5 JP2020569188A JP2020569188A JPWO2019238633A5 JP WO2019238633 A5 JPWO2019238633 A5 JP WO2019238633A5 JP 2020569188 A JP2020569188 A JP 2020569188A JP 2020569188 A JP2020569188 A JP 2020569188A JP WO2019238633 A5 JPWO2019238633 A5 JP WO2019238633A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridazine
- isoxazole
- methylpyridine
- oxa
- 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
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- -1 5-oxa-2-azaspiro [3.5] nonanyl Chemical group 0.000 claims 172
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 108
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 56
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- AFZIEAKWXPVRDU-UHFFFAOYSA-N 5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazole Chemical compound CC1=CC(=NO1)C=1N=NC(=CC=1)C AFZIEAKWXPVRDU-UHFFFAOYSA-N 0.000 claims 2
- UKQDILUIPHDWAA-UHFFFAOYSA-N 5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazole Chemical compound O1C(C)=CC(C=2C=NC(C)=CC=2)=N1 UKQDILUIPHDWAA-UHFFFAOYSA-N 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 1
- QXALUNHYJJONQH-UHFFFAOYSA-N 1,1,1-trifluoro-2-methylpropane Chemical compound CC(C)C(F)(F)F QXALUNHYJJONQH-UHFFFAOYSA-N 0.000 claims 1
- AKOBGSHVAABXAU-UHFFFAOYSA-N 1-[1-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]-6-oxopyridazin-4-yl]azetidine-3-carbonitrile Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC(C1)C#N AKOBGSHVAABXAU-UHFFFAOYSA-N 0.000 claims 1
- HDONZAILTKEKCT-UHFFFAOYSA-N 1-[1-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]-6-oxopyridazin-4-yl]piperidine-4-carbonitrile Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CCC(CC1)C#N HDONZAILTKEKCT-UHFFFAOYSA-N 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- RZDHHDURUVIWSS-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazin-6-one Chemical compound O=C1NCCN=C1 RZDHHDURUVIWSS-UHFFFAOYSA-N 0.000 claims 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 claims 1
- IOCJETXFHMHPAP-UHFFFAOYSA-N 2-[1-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]-6-oxopyridazin-4-yl]-1,3,4,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-6-one Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC2N(CC1)C(CC2)=O IOCJETXFHMHPAP-UHFFFAOYSA-N 0.000 claims 1
- ZYHHYHJSNMCNEQ-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(3-ethoxyazetidin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=C1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(C1)OCC)C ZYHHYHJSNMCNEQ-UHFFFAOYSA-N 0.000 claims 1
- NSWXPFQYOZEJGH-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(3-methoxyazetidin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=C1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(C1)OC)C NSWXPFQYOZEJGH-UHFFFAOYSA-N 0.000 claims 1
- VYFZJCPKFQLRRS-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-morpholin-4-ylpyridazin-3-one Chemical compound FC1=CC=C(C=C1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CCOCC1)C VYFZJCPKFQLRRS-UHFFFAOYSA-N 0.000 claims 1
- STZOJUQGZISWED-TXEJJXNPSA-N 2-[[3-(5-chloro-3-fluoropyridin-2-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyridazin-3-one Chemical compound ClC=1C=C(C(=NC=1)C1=NOC(=C1CN1N=CC(=CC1=O)N1C[C@@H](O[C@@H](C1)C)C)C)F STZOJUQGZISWED-TXEJJXNPSA-N 0.000 claims 1
- AUZPUCVKVSZECV-OKILXGFUSA-N 2-[[3-(5-chloropyridin-2-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methyl]-5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyridazin-3-one Chemical compound ClC=1C=CC(=NC=1)C1=NOC(=C1CN1N=CC(=CC1=O)N1C[C@@H](O[C@@H](C1)C)C)C1CC1 AUZPUCVKVSZECV-OKILXGFUSA-N 0.000 claims 1
- WUUUJRMSSOQQFI-UHFFFAOYSA-N 2-[[3-(5-chloropyridin-2-yl)-5-cyclopropyl-1,2-oxazol-4-yl]methyl]-5-[4-(cyclopropanecarbonyl)piperazin-1-yl]pyridazin-3-one Chemical compound ClC=1C=CC(=NC=1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CCN(CC1)C(=O)C1CC1)C1CC1 WUUUJRMSSOQQFI-UHFFFAOYSA-N 0.000 claims 1
- AIZNCMLONWNSEE-BETUJISGSA-N 2-[[3-(5-chloropyridin-2-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyridazin-3-one Chemical compound ClC=1C=CC(=NC=1)C1=NOC(=C1CN1N=CC(=CC1=O)N1C[C@@H](O[C@@H](C1)C)C)C AIZNCMLONWNSEE-BETUJISGSA-N 0.000 claims 1
- UAAFHYLNNPCCBL-UHFFFAOYSA-N 2-[[3-(5-chloropyridin-2-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[3-(cyclopropylmethoxy)azetidin-1-yl]pyridazin-3-one Chemical compound ClC=1C=CC(=NC=1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(C1)OCC1CC1)C UAAFHYLNNPCCBL-UHFFFAOYSA-N 0.000 claims 1
- QKYCXCHTHJFZER-UHFFFAOYSA-N 2-[[3-(5-chloropyridin-2-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[4-(1-methylcyclopropanecarbonyl)piperazin-1-yl]pyridazin-3-one Chemical compound ClC=1C=CC(=NC=1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CCN(CC1)C(=O)C1(CC1)C)C QKYCXCHTHJFZER-UHFFFAOYSA-N 0.000 claims 1
- ROJCAKDYTWGZAM-UHFFFAOYSA-N 2-[[3-(5-fluoro-6-methylpyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(2-methoxypyridin-4-yl)pyridazin-3-one Chemical compound FC=1C=C(C=NC=1C)C1=NOC(=C1CN1N=CC(=CC1=O)C1=CC(=NC=C1)OC)C ROJCAKDYTWGZAM-UHFFFAOYSA-N 0.000 claims 1
- NFLWKFUORSVWJK-UHFFFAOYSA-N 2-[[3-(5-fluoro-6-methylpyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(5-oxa-2-azaspiro[3.4]octan-2-yl)pyridazin-3-one Chemical compound FC=1C=C(C=NC=1C)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC2(C1)OCCC2)C NFLWKFUORSVWJK-UHFFFAOYSA-N 0.000 claims 1
- ZHVYVKARDIPYAY-UHFFFAOYSA-N 2-[[3-(6-chloropyridazin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(3-methoxyazetidin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(N=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(C1)OC)C ZHVYVKARDIPYAY-UHFFFAOYSA-N 0.000 claims 1
- FUZZRFANHBIKSZ-UHFFFAOYSA-N 2-[[3-(6-chloropyridazin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(7,7-difluoro-5-oxa-2-azaspiro[3.4]octan-2-yl)pyridazin-3-one Chemical compound ClC1=CC=C(N=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC2(C1)OCC(C2)(F)F)C FUZZRFANHBIKSZ-UHFFFAOYSA-N 0.000 claims 1
- UMXCNZKXXNJUOF-UHFFFAOYSA-N 2-[[3-(6-chloropyridazin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[3-[(2-methylpropan-2-yl)oxy]azetidin-1-yl]pyridazin-3-one Chemical compound C(C)(C)(C)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)Cl)=O UMXCNZKXXNJUOF-UHFFFAOYSA-N 0.000 claims 1
- BPBZTXVSAJJJKN-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(1-cyclopropylpyrazol-4-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)C=1C=NN(C=1)C1CC1)C BPBZTXVSAJJJKN-UHFFFAOYSA-N 0.000 claims 1
- NNEADJDAVFHMRT-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(2,6-dimethylmorpholin-4-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(OC(C1)C)C)C NNEADJDAVFHMRT-UHFFFAOYSA-N 0.000 claims 1
- FSVSNTFVJLNPDL-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(2-methoxypyridin-4-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)C1=CC(=NC=C1)OC)C FSVSNTFVJLNPDL-UHFFFAOYSA-N 0.000 claims 1
- NFUCQCHYVRDHJR-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(3-ethoxyazetidin-1-yl)pyridazin-3-one Chemical compound N1(CC(OCC)C1)C=1C=NN(C(=O)C=1)CC=1C(C2=CC=C(N=C2)Cl)=NOC=1C NFUCQCHYVRDHJR-UHFFFAOYSA-N 0.000 claims 1
- OOKVOVZGAXQLND-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(3-methoxyazetidin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(C1)OC)C OOKVOVZGAXQLND-UHFFFAOYSA-N 0.000 claims 1
- QBSVBZPNEICKCL-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(4-methoxy-4-methylpiperidin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CCC(CC1)(C)OC)C QBSVBZPNEICKCL-UHFFFAOYSA-N 0.000 claims 1
- VQEQXPGAVGZSAT-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(4-pyridazin-4-ylpiperazin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CCN(CC1)C1=CN=NC=C1)C VQEQXPGAVGZSAT-UHFFFAOYSA-N 0.000 claims 1
- BOQOCQLPKFSOBD-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(4-pyridin-3-ylpiperazin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CCN(CC1)C=1C=NC=CC=1)C BOQOCQLPKFSOBD-UHFFFAOYSA-N 0.000 claims 1
- JJKJLHMJKAKDII-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(4-pyrimidin-5-ylpiperazin-1-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CCN(CC1)C=1C=NC=NC=1)C JJKJLHMJKAKDII-UHFFFAOYSA-N 0.000 claims 1
- PTYDFZOZJHQMNR-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-(7,7-difluoro-5-oxa-2-azaspiro[3.4]octan-2-yl)pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC2(C1)OCC(C2)(F)F)C PTYDFZOZJHQMNR-UHFFFAOYSA-N 0.000 claims 1
- YTQQFFKSOBATSM-LBPRGKRZSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[(2S)-2-methylmorpholin-4-yl]pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1C[C@@H](OCC1)C)C YTQQFFKSOBATSM-LBPRGKRZSA-N 0.000 claims 1
- IRXAIGNMLXHJKG-OAHLLOKOSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[(7R)-7-(trifluoromethyl)-5-oxa-2-azaspiro[3.5]nonan-2-yl]pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC2(C1)OC[C@@H](CC2)C(F)(F)F)C IRXAIGNMLXHJKG-OAHLLOKOSA-N 0.000 claims 1
- RMOFAJLDWQJUAC-CQSZACIVSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[(7R)-7-methyl-5-oxa-2-azaspiro[3.5]nonan-2-yl]pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC2(C1)OC[C@@H](CC2)C)C RMOFAJLDWQJUAC-CQSZACIVSA-N 0.000 claims 1
- RMOFAJLDWQJUAC-AWEZNQCLSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[(7S)-7-methyl-5-oxa-2-azaspiro[3.5]nonan-2-yl]pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC2(C1)OC[C@H](CC2)C)C RMOFAJLDWQJUAC-AWEZNQCLSA-N 0.000 claims 1
- JKCSJVSZZYKSJC-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[3-(2,2-difluoroethoxy)azetidin-1-yl]pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(C1)OCC(F)F)C JKCSJVSZZYKSJC-UHFFFAOYSA-N 0.000 claims 1
- KJLYNEJZNISSEY-UHFFFAOYSA-N 2-[[3-(6-chloropyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]-5-[3-(trifluoromethoxy)azetidin-1-yl]pyridazin-3-one Chemical compound ClC1=CC=C(C=N1)C1=NOC(=C1CN1N=CC(=CC1=O)N1CC(C1)OC(F)(F)F)C KJLYNEJZNISSEY-UHFFFAOYSA-N 0.000 claims 1
- JQUDNMMKVRAWKC-OKILXGFUSA-N 2-[[5-(difluoromethyl)-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]-5-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridazin-3-one Chemical compound FC(C1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)N1C[C@@H](O[C@@H](C1)C)C)F JQUDNMMKVRAWKC-OKILXGFUSA-N 0.000 claims 1
- YPRHKIYNPMCSEA-UHFFFAOYSA-N 2-[[5-ethyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-(5-oxa-2-azaspiro[3.5]nonan-2-yl)pyridazin-3-one Chemical compound C(C)C1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC2(C1)OCCCC2 YPRHKIYNPMCSEA-UHFFFAOYSA-N 0.000 claims 1
- JBPJLWGCPKNUNX-OAHLLOKOSA-N 2-[[5-ethyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-[(7R)-7-fluoro-5-oxa-2-azaspiro[3.5]nonan-2-yl]pyridazin-3-one Chemical compound C(C)C1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC2(C1)OC[C@@H](CC2)F JBPJLWGCPKNUNX-OAHLLOKOSA-N 0.000 claims 1
- QKGWLFKPWBRIBD-UHFFFAOYSA-N 2-[[5-methyl-3-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazol-4-yl]methyl]-5-(5-oxa-2-azaspiro[3.4]octan-2-yl)pyridazin-3-one Chemical compound CC1=C(C(=NO1)C1=NOC(=C1)C)CN1N=CC(=CC1=O)N1CC2(C1)OCCC2 QKGWLFKPWBRIBD-UHFFFAOYSA-N 0.000 claims 1
- GBYJKWIKIITXLA-UHFFFAOYSA-N 2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-(1-oxa-9-azaspiro[5.5]undecan-9-yl)pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CCC2(CCCCO2)CC1 GBYJKWIKIITXLA-UHFFFAOYSA-N 0.000 claims 1
- PGZDDYDSURVPGB-UHFFFAOYSA-N 2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-(3-oxa-9-azaspiro[5.5]undecan-9-yl)pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CCC2(CCOCC2)CC1 PGZDDYDSURVPGB-UHFFFAOYSA-N 0.000 claims 1
- GEUJCIVKCFLWNC-UHFFFAOYSA-N 2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-(5-oxa-2-azaspiro[3.4]octan-2-yl)pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC2(C1)OCCC2 GEUJCIVKCFLWNC-UHFFFAOYSA-N 0.000 claims 1
- QYKLVMLNXMQKCM-UHFFFAOYSA-N 2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-(5-oxa-2-azaspiro[3.5]nonan-2-yl)pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC2(C1)OCCCC2 QYKLVMLNXMQKCM-UHFFFAOYSA-N 0.000 claims 1
- QCRLHRUUXJKVFE-UHFFFAOYSA-N 2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-(5-oxa-2-azaspiro[3.6]decan-2-yl)pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC2(C1)OCCCCC2 QCRLHRUUXJKVFE-UHFFFAOYSA-N 0.000 claims 1
- RDVDJSDTFAQBSD-QGZVFWFLSA-N 2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]-5-[(3R)-3-[(2-methylpropan-2-yl)oxy]pyrrolidin-1-yl]pyridazin-3-one Chemical compound C(C)(C)(C)O[C@H]1CN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)C)=O RDVDJSDTFAQBSD-QGZVFWFLSA-N 0.000 claims 1
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- GBFJQDXVEQRJQJ-UHFFFAOYSA-N 5-(2-methoxyphenyl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1=C(C=CC=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O GBFJQDXVEQRJQJ-UHFFFAOYSA-N 0.000 claims 1
- OSQFOOYFUSZITH-UHFFFAOYSA-N 5-(2-methoxypyridin-4-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1=NC=CC(=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O OSQFOOYFUSZITH-UHFFFAOYSA-N 0.000 claims 1
- MZRPLZUPOFTDAL-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC=1C=C(C=CC=1OC)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O MZRPLZUPOFTDAL-UHFFFAOYSA-N 0.000 claims 1
- MOSXMOQUJJJSDZ-UHFFFAOYSA-N 5-(3-cyclobutyloxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CCC1)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)C)=O MOSXMOQUJJJSDZ-UHFFFAOYSA-N 0.000 claims 1
- RDLQNLITRCIUAS-UHFFFAOYSA-N 5-(3-cyclopropyloxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)C)=O RDLQNLITRCIUAS-UHFFFAOYSA-N 0.000 claims 1
- ODWSOPHFXUPLQI-UHFFFAOYSA-N 5-(3-cyclopropyloxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O ODWSOPHFXUPLQI-UHFFFAOYSA-N 0.000 claims 1
- CAYGUZJNQDHAMJ-UHFFFAOYSA-N 5-(3-cyclopropyloxyazetidin-1-yl)-2-[[5-methyl-3-[5-(trifluoromethyl)pyrimidin-2-yl]-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C1=NC=C(C=N1)C(F)(F)F)=O CAYGUZJNQDHAMJ-UHFFFAOYSA-N 0.000 claims 1
- LMCKQBUBQKEKLA-UHFFFAOYSA-N 5-(3-ethoxyazetidin-1-yl)-2-[[3-(5-fluoro-6-methylpyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C(C)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=C(C=1)F)C)=O LMCKQBUBQKEKLA-UHFFFAOYSA-N 0.000 claims 1
- AAHNOFRMJIDVQB-UHFFFAOYSA-N 5-(3-ethoxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C(C)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)C)=O AAHNOFRMJIDVQB-UHFFFAOYSA-N 0.000 claims 1
- ZDTYWHJVZJNBOV-UHFFFAOYSA-N 5-(3-ethoxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C(C)OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O ZDTYWHJVZJNBOV-UHFFFAOYSA-N 0.000 claims 1
- JKKXNOPIPWZBOG-UHFFFAOYSA-N 5-(3-fluoroazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O JKKXNOPIPWZBOG-UHFFFAOYSA-N 0.000 claims 1
- YHDJMBCVKQDACA-UHFFFAOYSA-N 5-(3-hydroxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O YHDJMBCVKQDACA-UHFFFAOYSA-N 0.000 claims 1
- IRDQKOYFAMCTNV-UHFFFAOYSA-N 5-(3-methoxyazetidin-1-yl)-2-[[5-methyl-3-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CC1=C(C(=NO1)C1=NOC(=C1)C)CN1N=CC(=CC1=O)N1CC(C1)OC IRDQKOYFAMCTNV-UHFFFAOYSA-N 0.000 claims 1
- JPAMTPDXYCCUFO-UHFFFAOYSA-N 5-(3-methoxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)C)=O JPAMTPDXYCCUFO-UHFFFAOYSA-N 0.000 claims 1
- QJWAMJXONIVPIA-UHFFFAOYSA-N 5-(3-methoxyazetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O QJWAMJXONIVPIA-UHFFFAOYSA-N 0.000 claims 1
- LFAVHSBNVVNLCL-UHFFFAOYSA-N 5-(4,7-diazaspiro[2.5]octan-7-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CCNC2(CC2)C1 LFAVHSBNVVNLCL-UHFFFAOYSA-N 0.000 claims 1
- PQTJVJOYKWGHHO-UHFFFAOYSA-N 5-(4-cyclopropylpiperazin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)N1CCN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O PQTJVJOYKWGHHO-UHFFFAOYSA-N 0.000 claims 1
- QQZSHVDDOGFKBS-UHFFFAOYSA-N 5-(4-ethoxyphenyl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C(C)OC1=CC=C(C=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O QQZSHVDDOGFKBS-UHFFFAOYSA-N 0.000 claims 1
- GGTJEFVMAMTNQU-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC1=CC=C(C=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O GGTJEFVMAMTNQU-UHFFFAOYSA-N 0.000 claims 1
- UXOOWFGBBLLOJG-UHFFFAOYSA-N 5-(4-hydroxypiperidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound OC1CCN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O UXOOWFGBBLLOJG-UHFFFAOYSA-N 0.000 claims 1
- YNPVBIBAZJFZDD-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1=CC=C(C=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O YNPVBIBAZJFZDD-UHFFFAOYSA-N 0.000 claims 1
- UFTUYERRFQSCDJ-UHFFFAOYSA-N 5-(4-methoxypiperidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1CCN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O UFTUYERRFQSCDJ-UHFFFAOYSA-N 0.000 claims 1
- QGKGROFTSKMUTA-UHFFFAOYSA-N 5-(5,6-dimethoxypyridin-3-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC=1C=C(C=NC=1OC)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O QGKGROFTSKMUTA-UHFFFAOYSA-N 0.000 claims 1
- MCHSTISNKRAPOL-UHFFFAOYSA-N 5-(5-chloro-6-methoxypyridin-3-yl)-2-[[3-(6-chloropyridazin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound ClC=1C=C(C=NC=1OC)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)Cl)=O MCHSTISNKRAPOL-UHFFFAOYSA-N 0.000 claims 1
- FDMPOOLRFQKJLS-UHFFFAOYSA-N 5-(5-chloropyridin-3-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound ClC=1C=C(C=NC=1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O FDMPOOLRFQKJLS-UHFFFAOYSA-N 0.000 claims 1
- XYQSRVPMPHEJQR-UHFFFAOYSA-N 5-(5-methoxypyridin-2-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC=1C=CC(=NC=1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O XYQSRVPMPHEJQR-UHFFFAOYSA-N 0.000 claims 1
- GKHCHNRQAHTFIS-UHFFFAOYSA-N 5-(6-cyclopropylpyridin-3-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)C1=CC=C(C=N1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O GKHCHNRQAHTFIS-UHFFFAOYSA-N 0.000 claims 1
- BRLIURGZBPQVLK-UHFFFAOYSA-N 5-(6-ethoxypyridin-3-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C(C)OC1=CC=C(C=N1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O BRLIURGZBPQVLK-UHFFFAOYSA-N 0.000 claims 1
- MCALIWGDRXPWCR-UHFFFAOYSA-N 5-(6-methoxypyridin-2-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1=CC=CC(=N1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O MCALIWGDRXPWCR-UHFFFAOYSA-N 0.000 claims 1
- ITQPMOBFYVDJDP-UHFFFAOYSA-N 5-(6-methoxypyridin-3-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1=CC=C(C=N1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O ITQPMOBFYVDJDP-UHFFFAOYSA-N 0.000 claims 1
- AKADLUFDTIIXOV-UHFFFAOYSA-N 5-(azetidin-1-yl)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound N1(CCC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O AKADLUFDTIIXOV-UHFFFAOYSA-N 0.000 claims 1
- ZVZQCPLRQMBNLY-UHFFFAOYSA-N 5-(dimethylamino)-2-[[3-(5-fluoro-6-methylpyridin-3-yl)-5-methyl-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CN(C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=C(C=1)F)C)=O)C ZVZQCPLRQMBNLY-UHFFFAOYSA-N 0.000 claims 1
- ZVWXMLNRHIFFFT-UHFFFAOYSA-N 5-(dimethylamino)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CN(C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C ZVWXMLNRHIFFFT-UHFFFAOYSA-N 0.000 claims 1
- NOXODAIJBKNFAY-UHFFFAOYSA-N 5-(methylamino)-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)NC NOXODAIJBKNFAY-UHFFFAOYSA-N 0.000 claims 1
- CPCHRGFQWZMVNX-UHFFFAOYSA-N 5-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CN=CN=C1 CPCHRGFQWZMVNX-UHFFFAOYSA-N 0.000 claims 1
- OPIFLKRMHIBLGA-UHFFFAOYSA-N 5-[(1-cyclopropylazetidin-3-yl)-methylamino]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)N1CC(C1)N(C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C OPIFLKRMHIBLGA-UHFFFAOYSA-N 0.000 claims 1
- XMPUPLZCHBVIIG-UHFFFAOYSA-N 5-[(2-hydroxy-2-methylpropyl)-methylamino]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound OC(CN(C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C)(C)C XMPUPLZCHBVIIG-UHFFFAOYSA-N 0.000 claims 1
- XUOBJBMRYSIJMB-CQSZACIVSA-N 5-[(2R)-2-methylmorpholin-4-yl]-2-[[3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C[C@H]1OCCN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1)C=1C=NC(=CC=1)C)=O XUOBJBMRYSIJMB-CQSZACIVSA-N 0.000 claims 1
- XUOBJBMRYSIJMB-AWEZNQCLSA-N 5-[(2S)-2-methylmorpholin-4-yl]-2-[[3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C[C@@H]1OCCN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1)C=1C=NC(=CC=1)C)=O XUOBJBMRYSIJMB-AWEZNQCLSA-N 0.000 claims 1
- POJPNUCTJGZXDY-BETUJISGSA-N 5-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-[[3-(3-fluoropyridin-4-yl)-5-methyl-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C[C@@H]1O[C@@H](CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C1=C(C=NC=C1)F)=O)C POJPNUCTJGZXDY-BETUJISGSA-N 0.000 claims 1
- BUDXDIBVDYOASZ-OKILXGFUSA-N 5-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C[C@@H]1O[C@@H](CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C1=CC=C(C=C1)F)=O)C BUDXDIBVDYOASZ-OKILXGFUSA-N 0.000 claims 1
- ZCOQSITXECTXKY-GASCZTMLSA-N 5-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-[[3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C[C@@H]1CN(C[C@@H](O1)C)C1=CC(N(N=C1)CC=1C(=NOC=1)C=1C=NC(=CC=1)C)=O ZCOQSITXECTXKY-GASCZTMLSA-N 0.000 claims 1
- ZWJYZRGIUJXECL-BETUJISGSA-N 5-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-[[3-[6-(trifluoromethyl)pyridin-3-yl]-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C[C@@H]1O[C@@H](CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1)C=1C=NC(=CC=1)C(F)(F)F)=O)C ZWJYZRGIUJXECL-BETUJISGSA-N 0.000 claims 1
- XRKALCYEKHUUGH-BETUJISGSA-N 5-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-[[5-methyl-3-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CC1=C(C(=NO1)C1=NOC(=C1)C)CN1N=CC(=CC1=O)N1C[C@@H](O[C@@H](C1)C)C XRKALCYEKHUUGH-BETUJISGSA-N 0.000 claims 1
- JIGCMFBIUHCXHY-MRXNPFEDSA-N 5-[(3R)-3-hydroxypyrrolidin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound O[C@H]1CN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O JIGCMFBIUHCXHY-MRXNPFEDSA-N 0.000 claims 1
- LRIWZRKYTQBJBA-MRXNPFEDSA-N 5-[(3R)-4-cyclopropyl-3-methylpiperazin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)N1[C@@H](CN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C LRIWZRKYTQBJBA-MRXNPFEDSA-N 0.000 claims 1
- VXPPNXASGNUUOW-GASCZTMLSA-N 5-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C[C@H]1CN(C[C@H](N1)C)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O VXPPNXASGNUUOW-GASCZTMLSA-N 0.000 claims 1
- MYDOONMCNWJBTJ-KRWDZBQOSA-N 5-[(3S)-3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound OC(C)(C)[C@@H]1CN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O MYDOONMCNWJBTJ-KRWDZBQOSA-N 0.000 claims 1
- JIGCMFBIUHCXHY-INIZCTEOSA-N 5-[(3S)-3-hydroxypyrrolidin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound O[C@@H]1CN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O JIGCMFBIUHCXHY-INIZCTEOSA-N 0.000 claims 1
- LRIWZRKYTQBJBA-INIZCTEOSA-N 5-[(3S)-4-cyclopropyl-3-methylpiperazin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)N1[C@H](CN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C LRIWZRKYTQBJBA-INIZCTEOSA-N 0.000 claims 1
- UQMRXCPGSLSLND-UHFFFAOYSA-N 5-[1-(cyclopropylmethyl)pyrazol-4-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)CN1N=CC(=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O UQMRXCPGSLSLND-UHFFFAOYSA-N 0.000 claims 1
- YZXUCIAMTXXWJB-UHFFFAOYSA-N 5-[1-(difluoromethyl)pyrazol-4-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC(N1N=CC(=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)F YZXUCIAMTXXWJB-UHFFFAOYSA-N 0.000 claims 1
- DRYLSTFCCZFNSX-UHFFFAOYSA-N 5-[2-(azetidin-1-yl)pyridin-4-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound N1(CCC1)C1=NC=CC(=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O DRYLSTFCCZFNSX-UHFFFAOYSA-N 0.000 claims 1
- RQYTYJIJIVQAOG-UHFFFAOYSA-N 5-[2-(difluoromethoxy)pyridin-4-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC(OC1=NC=CC(=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)F RQYTYJIJIVQAOG-UHFFFAOYSA-N 0.000 claims 1
- DZYUNPFHAALEOI-UHFFFAOYSA-N 5-[2-(dimethylamino)pyridin-4-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CN(C1=NC=CC(=C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C DZYUNPFHAALEOI-UHFFFAOYSA-N 0.000 claims 1
- JWCTZKQODBHCFE-UHFFFAOYSA-N 5-[2-(methylamino)pyridin-4-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)C1=CC(=NC=C1)NC JWCTZKQODBHCFE-UHFFFAOYSA-N 0.000 claims 1
- HNEYQBLKELCTND-UHFFFAOYSA-N 5-[3-(1-methylcyclopropyl)oxyazetidin-1-yl]-2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1N=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC(C1)OC1(CC1)C HNEYQBLKELCTND-UHFFFAOYSA-N 0.000 claims 1
- NKQGTJIYXIVVBU-UHFFFAOYSA-N 5-[3-(2,2-difluoroethoxy)azetidin-1-yl]-2-[[5-methyl-3-(6-methylpyridazin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC(COC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1N=NC(=CC=1)C)=O)F NKQGTJIYXIVVBU-UHFFFAOYSA-N 0.000 claims 1
- BKFFSXUFUXGWCN-UHFFFAOYSA-N 5-[3-(2,2-difluoroethoxy)azetidin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC(COC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)F BKFFSXUFUXGWCN-UHFFFAOYSA-N 0.000 claims 1
- AMUYFVFPDBXPOF-UHFFFAOYSA-N 5-[3-(difluoromethoxy)azetidin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC(OC1CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)F AMUYFVFPDBXPOF-UHFFFAOYSA-N 0.000 claims 1
- XZHAOTACJSROPE-UHFFFAOYSA-N 5-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound OC1(CN(C1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C(F)(F)F XZHAOTACJSROPE-UHFFFAOYSA-N 0.000 claims 1
- FVIYVMPYSMHOSK-UHFFFAOYSA-N 5-[4-(1-methylcyclopropanecarbonyl)piperazin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CCN(CC1)C(=O)C1(CC1)C FVIYVMPYSMHOSK-UHFFFAOYSA-N 0.000 claims 1
- XAVXCROJQVKPEX-UHFFFAOYSA-N 5-[4-(2-methoxypyridin-3-yl)piperazin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1=NC=CC=C1N1CCN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O XAVXCROJQVKPEX-UHFFFAOYSA-N 0.000 claims 1
- ZGUTZLMBNKSOQF-UHFFFAOYSA-N 5-[4-(3-methoxypyridazin-4-yl)piperazin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC=1N=NC=CC=1N1CCN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O ZGUTZLMBNKSOQF-UHFFFAOYSA-N 0.000 claims 1
- JIYMKFAMVZFEHH-UHFFFAOYSA-N 5-[4-(4-methoxypyrimidin-5-yl)piperazin-1-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound COC1=NC=NC=C1N1CCN(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O JIYMKFAMVZFEHH-UHFFFAOYSA-N 0.000 claims 1
- PECYWBVSTGUYOO-UHFFFAOYSA-N 5-[6-(difluoromethoxy)pyridin-3-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound FC(OC1=CC=C(C=N1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)F PECYWBVSTGUYOO-UHFFFAOYSA-N 0.000 claims 1
- IMAFHEWVTKZSMH-UHFFFAOYSA-N 5-[6-(dimethylamino)pyridin-3-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CN(C1=CC=C(C=N1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C IMAFHEWVTKZSMH-UHFFFAOYSA-N 0.000 claims 1
- ZAERDKVKISJYIG-UHFFFAOYSA-N 5-[6-(methylamino)pyridin-3-yl]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound CNC1=CC=C(C=N1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O ZAERDKVKISJYIG-UHFFFAOYSA-N 0.000 claims 1
- MDFIOJLBOWRQPI-UHFFFAOYSA-N 5-[cyclopropyl(methyl)amino]-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)N(C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O)C MDFIOJLBOWRQPI-UHFFFAOYSA-N 0.000 claims 1
- LDXWIYFTPGYFQX-UHFFFAOYSA-N 5-cyclopropyl-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C1(CC1)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O LDXWIYFTPGYFQX-UHFFFAOYSA-N 0.000 claims 1
- CLGJPHGRCFNNGO-UHFFFAOYSA-N 5-ethyl-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C(C)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O CLGJPHGRCFNNGO-UHFFFAOYSA-N 0.000 claims 1
- HDCVTQAPAIPEOQ-UHFFFAOYSA-N 5-tert-butyl-2-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]pyridazin-3-one Chemical compound C(C)(C)(C)C1=CC(N(N=C1)CC=1C(=NOC=1C)C=1C=NC(=CC=1)C)=O HDCVTQAPAIPEOQ-UHFFFAOYSA-N 0.000 claims 1
- BICJQDPKHYJDNW-UHFFFAOYSA-N 6-[1-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]-6-oxopyridazin-4-yl]pyridine-2-carbonitrile Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)C1=CC=CC(=N1)C#N BICJQDPKHYJDNW-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- LWEFWEAPBIDBPT-UHFFFAOYSA-N 7-[1-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]-6-oxopyridazin-4-yl]-5,6,8,8a-tetrahydro-1H-[1,3]oxazolo[3,4-a]pyrazin-3-one Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)N1CC2N(CC1)C(OC2)=O LWEFWEAPBIDBPT-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000009575 Angelman syndrome Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- RPFANHNSSZHSFZ-UHFFFAOYSA-N CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)C=1C=NN(C=1)C1=CC=CC=C1 Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)C=1C=NN(C=1)C1=CC=CC=C1 RPFANHNSSZHSFZ-UHFFFAOYSA-N 0.000 claims 1
- UZERIGHZQQSBPU-UHFFFAOYSA-N FCC1=CC(=NO1)C=1C=NC(=CC1)C Chemical compound FCC1=CC(=NO1)C=1C=NC(=CC1)C UZERIGHZQQSBPU-UHFFFAOYSA-N 0.000 claims 1
- 208000009668 Neurobehavioral Manifestations Diseases 0.000 claims 1
- 201000010769 Prader-Willi syndrome Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000007000 age related cognitive decline Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
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- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 230000003387 muscular Effects 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl 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
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- WNZACTNRXSATJB-UHFFFAOYSA-N tert-butyl 4-[1-[[5-methyl-3-(6-methylpyridin-3-yl)-1,2-oxazol-4-yl]methyl]-6-oxopyridazin-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound CC1=C(C(=NO1)C=1C=NC(=CC=1)C)CN1N=CC(=CC1=O)C1=CCN(CC1)C(=O)OC(C)(C)C WNZACTNRXSATJB-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| EP18177825 | 2018-06-14 | ||
| EP18177825.9 | 2018-06-14 | ||
| PCT/EP2019/065129 WO2019238633A1 (en) | 2018-06-13 | 2019-06-11 | New isoxazolyl ether derivatives as gaba a alpha5 pam |
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| JP2021527099A JP2021527099A (ja) | 2021-10-11 |
| JPWO2019238633A5 true JPWO2019238633A5 (https=) | 2022-06-13 |
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| JP (1) | JP7478676B2 (https=) |
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| TWI901650B (zh) | 2020-03-26 | 2025-10-21 | 匈牙利商羅特格登公司 | 啶及吡啶并〔３，４－ｃ〕嗒衍生物 |
| EP4149933B1 (en) * | 2020-05-13 | 2024-06-12 | F. Hoffmann-La Roche AG | New triazolyl derivatives as gaba a alpha5 pam |
| HU231691B1 (hu) | 2021-09-29 | 2025-10-28 | Richter Gedeon Nyrt | GABAA ALFA5 receptor modulátor hatású biciklusos aminszármazékok |
| WO2026009854A1 (ja) * | 2024-07-01 | 2026-01-08 | 日本たばこ産業株式会社 | ピリダジノン化合物及びその医薬用途 |
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| CA2682301A1 (en) * | 2007-04-18 | 2008-10-30 | Astrazeneca Ab | Xanthine compounds having a positive allosteric gabab receptor modulator effect |
| KR101237576B1 (ko) | 2007-12-04 | 2013-03-04 | 에프. 호프만-라 로슈 아게 | 아이속사졸로-피리딘 유도체 |
| US7943619B2 (en) * | 2007-12-04 | 2011-05-17 | Hoffmann-La Roche Inc. | Isoxazolo-pyridazine derivatives |
| CA2724842A1 (en) * | 2008-05-19 | 2009-11-26 | Sunovion Pharmaceuticals Inc. | Imidazo[1,2-a]pyridine compounds |
| JP5460858B2 (ja) * | 2009-05-05 | 2014-04-02 | エフ．ホフマン−ラ ロシュ アーゲー | イソオキサゾール−ピラゾール誘導体 |
| US8604062B2 (en) | 2011-10-20 | 2013-12-10 | Hoffman-La Roche Inc. | Process for the preparation of isoxazolyl-methoxy nicotinic acids |
| US8785435B2 (en) | 2011-10-20 | 2014-07-22 | Hoffmann-La Roche Inc. | Solid forms |
| BR112019006571A2 (pt) | 2016-12-08 | 2019-07-02 | F. Hoffmann-La Roche Ag | derivados de éter de isoxazolila como gaba a alfa5 pam |
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2020
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