JP2018511627A5 - - Google Patents
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- Publication number
- JP2018511627A5 JP2018511627A5 JP2017553877A JP2017553877A JP2018511627A5 JP 2018511627 A5 JP2018511627 A5 JP 2018511627A5 JP 2017553877 A JP2017553877 A JP 2017553877A JP 2017553877 A JP2017553877 A JP 2017553877A JP 2018511627 A5 JP2018511627 A5 JP 2018511627A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrido
- oxo
- trifluoromethyl
- pyrazol
- 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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- 150000001875 compounds Chemical class 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- -1 3-chloro-5- (trifluoromethyl) pyrazol-1-yl Chemical group 0.000 claims 4
- 206010010904 Convulsion Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 2
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 2
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- CMWBJBAILPBLIB-WCBMZHEXSA-N (1R,2R)-2-[2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-7-fluoro-4-oxopyrido[1,2-a]pyrimidin-6-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)F)[C@H]1[C@@H](C1)C#N)C(F)(F)F CMWBJBAILPBLIB-WCBMZHEXSA-N 0.000 claims 1
- CANODGNUGMXXDV-GXSJLCMTSA-N (1R,2R)-2-[2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-7-methoxy-4-oxopyrido[1,2-a]pyrimidin-6-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)OC)[C@H]1[C@@H](C1)C#N)C(F)(F)F CANODGNUGMXXDV-GXSJLCMTSA-N 0.000 claims 1
- PXLJMGCNGCDJTO-CMPLNLGQSA-N (1R,2R)-2-[2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-7-methyl-4-oxopyrido[1,2-a]pyrimidin-6-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)[C@H]1[C@@H](C1)C#N)C(F)(F)F PXLJMGCNGCDJTO-CMPLNLGQSA-N 0.000 claims 1
- XSISCWOKUQLCCR-CMPLNLGQSA-N (1R,2R)-2-[2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-8-methyl-4-oxopyrido[1,2-a]pyrimidin-6-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CC(=C2)C)[C@H]1[C@@H](C1)C#N)C(F)(F)F XSISCWOKUQLCCR-CMPLNLGQSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- GIQLLIHHXCSFFX-UHFFFAOYSA-N 2-[(3-chloro-2-fluorophenyl)methyl]-3-fluoro-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound ClC=1C(=C(C=CC=1)CC=1N=C2N(C(C=1F)=O)C(=C(C=C2)C)C(=O)NC)F GIQLLIHHXCSFFX-UHFFFAOYSA-N 0.000 claims 1
- YVDINJMRPDBYBO-UHFFFAOYSA-N 2-[(3-chloro-2-fluorophenyl)methyl]-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound ClC=1C(=C(C=CC=1)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NC)F YVDINJMRPDBYBO-UHFFFAOYSA-N 0.000 claims 1
- YWGSSNMKHUMLIP-UHFFFAOYSA-N 2-[(3-cyano-2-fluorophenyl)methyl]-3-fluoro-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C(#N)C=1C(=C(C=CC=1)CC=1N=C2N(C(C=1F)=O)C(=C(C=C2)C)C(=O)NC)F YWGSSNMKHUMLIP-UHFFFAOYSA-N 0.000 claims 1
- STKYLRPMWSTXMJ-UHFFFAOYSA-N 2-[(3-cyano-2-fluorophenyl)methyl]-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C(#N)C=1C(=C(C=CC=1)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NC)F STKYLRPMWSTXMJ-UHFFFAOYSA-N 0.000 claims 1
- NRDLZVPGNJRUOL-UHFFFAOYSA-N 2-[(3-cyano-2-fluorophenyl)methyl]-N-ethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C(#N)C=1C(=C(C=CC=1)CC=1N=C2N(C(C=1)=O)C(=CC=C2)C(=O)NCC)F NRDLZVPGNJRUOL-UHFFFAOYSA-N 0.000 claims 1
- YHUHKPPRXXNFCO-UHFFFAOYSA-N 2-[(3-cyano-2-fluorophenyl)methyl]-N-ethyl-7-methyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C(#N)C=1C(=C(C=CC=1)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NCC)F YHUHKPPRXXNFCO-UHFFFAOYSA-N 0.000 claims 1
- AASFYRNWSHXWIV-UHFFFAOYSA-N 2-[(3-cyclopropyl-2-fluorophenyl)methyl]-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C1(CC1)C=1C(=C(C=CC=1)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NC)F AASFYRNWSHXWIV-UHFFFAOYSA-N 0.000 claims 1
- CIGNVKNVEPJEIV-UHFFFAOYSA-N 2-[(5-chloro-3-methylpyrazol-1-yl)methyl]-7-methoxy-6-(2-methylcyclopropyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound COC1=C(C2CC2C)N2C(=O)C=C(CN3N=C(C)C=C3Cl)N=C2C=C1 CIGNVKNVEPJEIV-UHFFFAOYSA-N 0.000 claims 1
- ZLJBQEHZSARYSF-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-4-oxopyrido[1,2-a]pyrimidine-6-carbonitrile Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=CC=C2)C#N ZLJBQEHZSARYSF-UHFFFAOYSA-N 0.000 claims 1
- ISEBYYVBBPZCKS-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-6-(furan-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=CC=C2)C=1OC=CC=1 ISEBYYVBBPZCKS-UHFFFAOYSA-N 0.000 claims 1
- UNZMBGODSMYNAC-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-6-methoxy-7-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)OC UNZMBGODSMYNAC-UHFFFAOYSA-N 0.000 claims 1
- BKAKLMTUIIEBQN-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-6-methoxypyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=CC=C2)OC BKAKLMTUIIEBQN-UHFFFAOYSA-N 0.000 claims 1
- YLRNIDSUDPFNPF-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-6-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=CC=C2)C YLRNIDSUDPFNPF-UHFFFAOYSA-N 0.000 claims 1
- PHQKAKFTYMJGCJ-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-6-pyrimidin-5-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=CC=C2)C=1C=NC=NC=1 PHQKAKFTYMJGCJ-UHFFFAOYSA-N 0.000 claims 1
- RNWMPZDONLVVMQ-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-7-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C=C(C=C2)C RNWMPZDONLVVMQ-UHFFFAOYSA-N 0.000 claims 1
- VMUKPRRMMBFZCX-UHFFFAOYSA-N 2-[(N-ethyl-4-fluoroanilino)methyl]-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C(C)N(C1=CC=C(C=C1)F)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NC VMUKPRRMMBFZCX-UHFFFAOYSA-N 0.000 claims 1
- OLPHYKMWWHKMQS-UHFFFAOYSA-N 2-[(n-ethylanilino)methyl]-7-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C(=O)N2C=C(C)C=CC2=NC=1CN(CC)C1=CC=CC=C1 OLPHYKMWWHKMQS-UHFFFAOYSA-N 0.000 claims 1
- VZDHZXIHFSANFG-UHFFFAOYSA-N 2-[2-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-7-fluoro-4-oxopyrido[1,2-a]pyrimidin-6-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)F)C1C(C1)C#N VZDHZXIHFSANFG-UHFFFAOYSA-N 0.000 claims 1
- ULUNRUNZUDWLFA-UHFFFAOYSA-N 2-[2-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-7-methyl-4-oxopyrido[1,2-a]pyrimidin-6-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C1C(C1)C#N ULUNRUNZUDWLFA-UHFFFAOYSA-N 0.000 claims 1
- HVBJXKGBBYZTEF-UHFFFAOYSA-N 2-[2-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-8-methyl-4-oxopyrido[1,2-a]pyrimidin-6-yl]cyclopropane-1-carbonitrile Chemical compound ClC1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=CC(=C2)C)C1C(C1)C#N HVBJXKGBBYZTEF-UHFFFAOYSA-N 0.000 claims 1
- CUVYQEMREGRGID-UHFFFAOYSA-N 2-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound FC1=C(C=CC=C1C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NC CUVYQEMREGRGID-UHFFFAOYSA-N 0.000 claims 1
- OYOFREMAXAPKEG-UHFFFAOYSA-N 2-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C1(CC1)C1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NC OYOFREMAXAPKEG-UHFFFAOYSA-N 0.000 claims 1
- HHUOPRJFKHUDCY-UHFFFAOYSA-N 2-[[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-7-methyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C1(CC1)C1=NN(C(=C1)C(F)(F)F)CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NCC HHUOPRJFKHUDCY-UHFFFAOYSA-N 0.000 claims 1
- QXIFDJHYBCLIKQ-UHFFFAOYSA-N 2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C=CC=C2)C(F)(F)F QXIFDJHYBCLIKQ-UHFFFAOYSA-N 0.000 claims 1
- GWRFUZNYFIIXBN-UHFFFAOYSA-N 2-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N,7-dimethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NC)C(F)(F)F GWRFUZNYFIIXBN-UHFFFAOYSA-N 0.000 claims 1
- DOOUMSLVIZLSHU-UHFFFAOYSA-N 2-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CC=C2)C(=O)NCC)C(F)(F)F DOOUMSLVIZLSHU-UHFFFAOYSA-N 0.000 claims 1
- KJEBDDULKDJINE-UHFFFAOYSA-N 2-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-7-methyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)C(=O)NCC)C(F)(F)F KJEBDDULKDJINE-UHFFFAOYSA-N 0.000 claims 1
- LLPFYDIOVSDPQX-UHFFFAOYSA-N 2-[[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-N-ethyl-8-methyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C1(CC1)C1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CC(=C2)C)C(=O)NCC)C(F)(F)F LLPFYDIOVSDPQX-UHFFFAOYSA-N 0.000 claims 1
- SVYFCSMXVAIKBD-UHFFFAOYSA-N 6-acetyl-2-[[3-chloro-5-(trifluoromethyl)pyrazol-1-yl]methyl]-7-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)(=O)C1=C(C=CC=2N1C(C=C(N=2)CN1N=C(C=C1C(F)(F)F)Cl)=O)C SVYFCSMXVAIKBD-UHFFFAOYSA-N 0.000 claims 1
- CVNZOKKGYMPHLM-UHFFFAOYSA-N 6-acetyl-2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-7-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)(=O)C1=C(C=CC=2N1C(C=C(N=2)CN1N=C(C=C1Cl)C(F)(F)F)=O)C CVNZOKKGYMPHLM-UHFFFAOYSA-N 0.000 claims 1
- DLJUZBHJTMNLHY-UHFFFAOYSA-N 6-acetyl-2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)(=O)C1=CC=CC=2N1C(C=C(N=2)CN1N=C(C=C1Cl)C(F)(F)F)=O DLJUZBHJTMNLHY-UHFFFAOYSA-N 0.000 claims 1
- RMLZDOOSPFUMBW-UHFFFAOYSA-N 6-bromo-2-[(N-ethyl-4-fluoroanilino)methyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound BrC1=CC=CC=2N1C(C=C(N=2)CN(C1=CC=C(C=C1)F)CC)=O RMLZDOOSPFUMBW-UHFFFAOYSA-N 0.000 claims 1
- CAZZSJVYBYNVAH-UHFFFAOYSA-N 6-chloro-2-[[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]methyl]-8-(trifluoromethyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound ClC1=CC(=CC=2N1C(C=C(N=2)CN1N=C(C=C1Cl)C(F)(F)F)=O)C(F)(F)F CAZZSJVYBYNVAH-UHFFFAOYSA-N 0.000 claims 1
- BVFJRDSRDWIVBV-UHFFFAOYSA-N 6-ethoxy-2-[(N-ethyl-4-fluoroanilino)methyl]-7-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)OC1=C(C=CC=2N1C(C=C(N=2)CN(C1=CC=C(C=C1)F)CC)=O)C BVFJRDSRDWIVBV-UHFFFAOYSA-N 0.000 claims 1
- MWYSJIYXSXMVPH-UHFFFAOYSA-N 6-ethoxy-2-[(N-ethyl-4-fluoroanilino)methyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)OC1=CC=CC=2N1C(C=C(N=2)CN(C1=CC=C(C=C1)F)CC)=O MWYSJIYXSXMVPH-UHFFFAOYSA-N 0.000 claims 1
- JIQNNJMGUPDLAN-UHFFFAOYSA-N 6-ethyl-2-[(N-ethyl-4-fluoroanilino)methyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)C1=CC=CC=2N1C(C=C(N=2)CN(C1=CC=C(C=C1)F)CC)=O JIQNNJMGUPDLAN-UHFFFAOYSA-N 0.000 claims 1
- XIULPRIKVVTTOE-UHFFFAOYSA-N 6-ethyl-2-[(N-ethylanilino)methyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C(C)C1=CC=CC=2N1C(C=C(N=2)CN(C1=CC=CC=C1)CC)=O XIULPRIKVVTTOE-UHFFFAOYSA-N 0.000 claims 1
- ZBURIMVPAULINH-UHFFFAOYSA-N 7-methyl-2-[(n-methylanilino)methyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C(=O)N2C=C(C)C=CC2=NC=1CN(C)C1=CC=CC=C1 ZBURIMVPAULINH-UHFFFAOYSA-N 0.000 claims 1
- MDIPIFAXDQKSGJ-CMPLNLGQSA-N CC(F)(F)C1=NN(CC2=CC(=O)N3C(C=CC=C3[C@@H]3C[C@H]3C#N)=N2)C(Cl)=C1 Chemical compound CC(F)(F)C1=NN(CC2=CC(=O)N3C(C=CC=C3[C@@H]3C[C@H]3C#N)=N2)C(Cl)=C1 MDIPIFAXDQKSGJ-CMPLNLGQSA-N 0.000 claims 1
- ZIQAAZNDFSSJJV-PWSUYJOCSA-N ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)[C@@H]1[C@H](C1)CO)C(F)(F)F Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)[C@@H]1[C@H](C1)CO)C(F)(F)F ZIQAAZNDFSSJJV-PWSUYJOCSA-N 0.000 claims 1
- ZIQAAZNDFSSJJV-CMPLNLGQSA-N ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)[C@H]1[C@@H](C1)CO)C(F)(F)F Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)C)[C@H]1[C@@H](C1)CO)C(F)(F)F ZIQAAZNDFSSJJV-CMPLNLGQSA-N 0.000 claims 1
- CMWBJBAILPBLIB-SCZZXKLOSA-N ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)F)[C@@H]1[C@H](C1)C#N)C(F)(F)F Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)F)[C@@H]1[C@H](C1)C#N)C(F)(F)F CMWBJBAILPBLIB-SCZZXKLOSA-N 0.000 claims 1
- CANODGNUGMXXDV-KOLCDFICSA-N ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)OC)[C@@H]1[C@H](C1)C#N)C(F)(F)F Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=C(C=C2)OC)[C@@H]1[C@H](C1)C#N)C(F)(F)F CANODGNUGMXXDV-KOLCDFICSA-N 0.000 claims 1
- XSISCWOKUQLCCR-PWSUYJOCSA-N ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CC(=C2)C)[C@@H]1[C@H](C1)C#N)C(F)(F)F Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CC(=C2)C)[C@@H]1[C@H](C1)C#N)C(F)(F)F XSISCWOKUQLCCR-PWSUYJOCSA-N 0.000 claims 1
- DOWVTWKIXIRDDR-KOLCDFICSA-N ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CC=C2)[C@@H]1[C@H](C1)C#N)C(F)(F)F Chemical compound ClC1=CC(=NN1CC=1N=C2N(C(C=1)=O)C(=CC=C2)[C@@H]1[C@H](C1)C#N)C(F)(F)F DOWVTWKIXIRDDR-KOLCDFICSA-N 0.000 claims 1
- GPMGDUIAVSFGGH-SCZZXKLOSA-N ClC=1C=CC=2N(C(C=C(N=2)CN2N=C(C=C2Cl)C(F)(F)F)=O)C=1[C@@H]1[C@H](C1)C#N Chemical compound ClC=1C=CC=2N(C(C=C(N=2)CN2N=C(C=C2Cl)C(F)(F)F)=O)C=1[C@@H]1[C@H](C1)C#N GPMGDUIAVSFGGH-SCZZXKLOSA-N 0.000 claims 1
- SLYSEOQRBVATEA-UHFFFAOYSA-N N-ethyl-2-[(4-fluorophenoxy)methyl]-7-methyl-4-oxopyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C(C)NC(=O)C1=C(C=CC=2N1C(C=C(N=2)COC1=CC=C(C=C1)F)=O)C SLYSEOQRBVATEA-UHFFFAOYSA-N 0.000 claims 1
- IUHQWCRWYUQNIU-UHFFFAOYSA-N N-ethyl-7-methyl-4-oxo-2-[[3-(trifluoromethyl)pyrazol-1-yl]methyl]pyrido[1,2-a]pyrimidine-6-carboxamide Chemical compound C(C)NC(=O)C1=C(C=CC=2N1C(C=C(N=2)CN1N=C(C=C1)C(F)(F)F)=O)C IUHQWCRWYUQNIU-UHFFFAOYSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
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| PT3055315T (pt) | 2013-10-11 | 2018-10-25 | Hoffmann La Roche | Tiazolopirimidonas enquanto moduladores da atividade do recetor nmda |
| PE20180316A1 (es) | 2015-04-15 | 2018-02-09 | Hoffmann La Roche | Compuestos piridopirimidinona y su uso como moduladores del receptor de nmda |
| ES2821010T3 (es) | 2015-12-09 | 2021-04-23 | Cadent Therapeutics Inc | Moduladores heteroaromáticos del receptor NMDA y usos de los mismos |
| AU2017382339B2 (en) | 2016-12-22 | 2024-02-15 | Novartis Ag | NMDA receptor modulators and uses thereof |
| PT3830092T (pt) | 2018-08-03 | 2023-07-25 | Novartis Ag | Moduladores do recetor nmda heteroaromáticos e suas utilizações |
| CN116322696A (zh) | 2020-05-04 | 2023-06-23 | 安进公司 | 作为髓样细胞上表达的触发受体2激动剂的杂环化合物和使用方法 |
| TW202208355A (zh) | 2020-05-04 | 2022-03-01 | 美商安進公司 | 作為骨髓細胞觸發受體2促效劑之雜環化合物及使用方法 |
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| US6951875B2 (en) * | 2001-10-29 | 2005-10-04 | Hoffmann-La Roche Inc. | Conjugated aromatic compounds with a pyridine substituent |
| US7148226B2 (en) | 2003-02-21 | 2006-12-12 | Agouron Pharmaceuticals, Inc. | Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same |
| ES2339862T3 (es) * | 2003-06-20 | 2010-05-26 | Novartis Vaccines And Diagnostics, Inc. | Compuestos de piridino 1,2-a-pirimidin-4-ona como agentes anticancerosos. |
| NL2000397C2 (nl) | 2006-01-05 | 2007-10-30 | Pfizer Prod Inc | Bicyclische heteroarylverbindingen als PDE10 inhibitoren. |
| CA2677493A1 (en) * | 2007-02-05 | 2008-08-14 | Xenon Pharmaceuticals Inc. | Pyridopyrimidinone compounds useful in treating sodium channel-mediated diseases or conditions |
| KR101811549B1 (ko) * | 2013-06-19 | 2017-12-26 | 에프. 호프만-라 로슈 아게 | 인돌린-2-온 또는 피롤로-피리딘/피리미딘-2-온 유도체 |
| PT3055315T (pt) * | 2013-10-11 | 2018-10-25 | Hoffmann La Roche | Tiazolopirimidonas enquanto moduladores da atividade do recetor nmda |
| PE20180316A1 (es) | 2015-04-15 | 2018-02-09 | Hoffmann La Roche | Compuestos piridopirimidinona y su uso como moduladores del receptor de nmda |
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2020
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