JP2020516672A5 - - Google Patents

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Publication number

JP2020516672A5

JP2020516672A5 JP2019556274A JP2019556274A JP2020516672A5 JP 2020516672 A5 JP2020516672 A5 JP 2020516672A5 JP 2019556274 A JP2019556274 A JP 2019556274A JP 2019556274 A JP2019556274 A JP 2019556274A JP 2020516672 A5 JP2020516672 A5 JP 2020516672A5

Authority

JP

Japan

Prior art keywords

pyrazole

methyl

oxo

benzonitrile

dihydropyridine

Prior art date

2018-04-18

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 pyrazoridinyl Chemical group 0.000 claims 62
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 53
• 150000001875 compounds Chemical class 0.000 claims 30
• 125000000217 alkyl group Chemical group 0.000 claims 26
• 125000001072 heteroaryl group Chemical group 0.000 claims 25
• 125000003118 aryl group Chemical group 0.000 claims 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims 17
• 125000000623 heterocyclic group Chemical group 0.000 claims 17
• 229910052739 hydrogen Inorganic materials 0.000 claims 16
• 239000001257 hydrogen Substances 0.000 claims 16
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims 15
• 125000003710 aryl alkyl group Chemical group 0.000 claims 14
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 14
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 14
• 150000002431 hydrogen Chemical class 0.000 claims 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims 11
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
• 125000003545 alkoxy group Chemical group 0.000 claims 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
• 229910052736 halogen Inorganic materials 0.000 claims 8
• 150000002367 halogens Chemical class 0.000 claims 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
• 125000001424 substituent group Chemical group 0.000 claims 5
• OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims 4
• 239000002253 acid Substances 0.000 claims 4
• 125000004122 cyclic group Chemical group 0.000 claims 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
• 150000004820 halides Chemical class 0.000 claims 3
• IHPHPGLJYCDONF-UHFFFAOYSA-N n-propylacetamide Chemical compound CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 claims 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims 3
• QJUKVLYAIWBKTK-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]pyrrole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C=C(C=C1)C(=O)N QJUKVLYAIWBKTK-UHFFFAOYSA-N 0.000 claims 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
• PFGWLUNKVJVTPJ-UHFFFAOYSA-N N-[[1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]pyrrolidin-3-yl]methyl]acetamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1CC(CC1)CNC(C)=O PFGWLUNKVJVTPJ-UHFFFAOYSA-N 0.000 claims 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
• 230000000694 effects Effects 0.000 claims 2
• 125000001188 haloalkyl group Chemical group 0.000 claims 2
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
• 125000002757 morpholinyl group Chemical group 0.000 claims 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
• 125000004076 pyridyl group Chemical group 0.000 claims 2
• 150000003839 salts Chemical class 0.000 claims 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
• ATCXRIPIGMFVBD-MRXNPFEDSA-N (3R)-1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]pyrrolidine-3-carboxylic acid Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C[C@@H](CC1)C(=O)O ATCXRIPIGMFVBD-MRXNPFEDSA-N 0.000 claims 1
• ATCXRIPIGMFVBD-INIZCTEOSA-N (3S)-1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]pyrrolidine-3-carboxylic acid Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C[C@H](CC1)C(=O)O ATCXRIPIGMFVBD-INIZCTEOSA-N 0.000 claims 1
• CJBIOEKIFDRINV-UHFFFAOYSA-N 1,3,4-trimethyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C(=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)C)=O CJBIOEKIFDRINV-UHFFFAOYSA-N 0.000 claims 1
• RGGCGLCKTILNRR-UHFFFAOYSA-N 1,3-dimethyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C(=CC(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O RGGCGLCKTILNRR-UHFFFAOYSA-N 0.000 claims 1
• QVWGIJIAGXMSIF-UHFFFAOYSA-N 1,3-dimethyl-5-[5-methyl-1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C(=CC(=C1)C=1C=NN(C=1C)C(C)C1=CC=CC=C1)C)=O QVWGIJIAGXMSIF-UHFFFAOYSA-N 0.000 claims 1
• OVBCUERDJPUNBJ-UHFFFAOYSA-N 1-(1h-pyrazol-5-yl)piperidine Chemical class C1CCCCN1C1=NNC=C1 OVBCUERDJPUNBJ-UHFFFAOYSA-N 0.000 claims 1
• YLXXXHVJQNFPBI-UHFFFAOYSA-N 1-[1-methyl-5-(1-methylpyrazol-4-yl)-2-oxopyridin-4-yl]pyrrole-3-carboxylic acid Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C)N1C=C(C=C1)C(=O)O)=O YLXXXHVJQNFPBI-UHFFFAOYSA-N 0.000 claims 1
• NGCFPHAEVPYKKM-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]-N,N-dimethylpyrrole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C=C(C=C1)C(=O)N(C)C NGCFPHAEVPYKKM-UHFFFAOYSA-N 0.000 claims 1
• VMDXOJQKQUTVRU-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]-N-ethylpyrrole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C=C(C=C1)C(=O)NCC VMDXOJQKQUTVRU-UHFFFAOYSA-N 0.000 claims 1
• QYKSFXYKYDPLCS-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]-N-methylpyrrolidine-3-carboxamide Chemical compound CNC(=O)C1CN(CC1)C1=CC(N(C=C1C=1C=NN(C=1)CC1=CC=CC=C1)C)=O QYKSFXYKYDPLCS-UHFFFAOYSA-N 0.000 claims 1
• HYEBJPKHSMSVLG-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]-N-methylpyrrolidine-3-sulfonamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1CC(CC1)S(=O)(=O)NC HYEBJPKHSMSVLG-UHFFFAOYSA-N 0.000 claims 1
• XRLGXLSNLQPNQF-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]-N-propan-2-ylpyrrole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C=C(C=C1)C(=O)NC(C)C XRLGXLSNLQPNQF-UHFFFAOYSA-N 0.000 claims 1
• GDSGNNQGIZZZSC-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]pyrrole-3-carbonitrile Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C=C(C=C1)C#N GDSGNNQGIZZZSC-UHFFFAOYSA-N 0.000 claims 1
• VOOQQGVQGVTNHW-UHFFFAOYSA-N 1-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]pyrrole-3-carboxylic acid Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C=C(C=C1)C(=O)O VOOQQGVQGVTNHW-UHFFFAOYSA-N 0.000 claims 1
• PBYGOIASWZDADD-UHFFFAOYSA-N 1-[5-[1-(cyclopropylmethyl)pyrazol-4-yl]-1-methyl-2-oxopyridin-4-yl]pyrrole-3-carboxylic acid Chemical compound C1(CC1)CN1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)N1C=C(C=C1)C(=O)O PBYGOIASWZDADD-UHFFFAOYSA-N 0.000 claims 1
• IXYZKXYBKXQHHP-UHFFFAOYSA-N 1-methyl-4-(1-methyl-2-oxopyridin-4-yl)-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C1=CC(N(C=C1)C)=O)=O IXYZKXYBKXQHHP-UHFFFAOYSA-N 0.000 claims 1
• HLNHRZGPOFFSFI-UHFFFAOYSA-N 1-methyl-4-(1-methylpyrazol-4-yl)-5-[1-[2-(2H-tetrazol-5-yl)phenyl]pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C1=C(C=CC=C1)C1=NN=NN1)C=1C=NN(C=1)C)=O HLNHRZGPOFFSFI-UHFFFAOYSA-N 0.000 claims 1
• ZGWLCPANXXSIMG-UHFFFAOYSA-N 1-methyl-4-(2-methylpropoxy)-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C(C(C)C)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O ZGWLCPANXXSIMG-UHFFFAOYSA-N 0.000 claims 1
• AGIOEMMQSOYBBE-UHFFFAOYSA-N 1-methyl-4-(3-methylazetidin-1-yl)-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)N1CC(C1)C)=O AGIOEMMQSOYBBE-UHFFFAOYSA-N 0.000 claims 1
• GHWLJJPYHDRPCS-UHFFFAOYSA-N 1-methyl-4-(methylamino)-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)NC)=O GHWLJJPYHDRPCS-UHFFFAOYSA-N 0.000 claims 1
• VBWVVCSGFRFGIJ-UHFFFAOYSA-N 1-methyl-4-[(1-methylpyrazol-3-yl)methoxy]-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)OCC1=NN(C=C1)C)=O VBWVVCSGFRFGIJ-UHFFFAOYSA-N 0.000 claims 1
• AOSNBJHXSUNBQH-UHFFFAOYSA-N 1-methyl-4-[2-(methylamino)pyrimidin-5-yl]-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C=1C=NC(=NC=1)NC)=O AOSNBJHXSUNBQH-UHFFFAOYSA-N 0.000 claims 1
• CXRSFLCEAGUDNZ-UHFFFAOYSA-N 1-methyl-4-morpholin-4-yl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)N1CCOCC1)=O CXRSFLCEAGUDNZ-UHFFFAOYSA-N 0.000 claims 1
• GFWWMJFTODFKGN-UHFFFAOYSA-N 1-methyl-4-phenoxy-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)OC1=CC=CC=C1)=O GFWWMJFTODFKGN-UHFFFAOYSA-N 0.000 claims 1
• KGUKKERQFZFWEO-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(1,3,5-trimethylpyrazol-4-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C(=NN(C=1C)C)C)C1=CC=CC=C1)=O KGUKKERQFZFWEO-UHFFFAOYSA-N 0.000 claims 1
• AJGADVRXPVDAHX-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(1-phenylpyrazol-4-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C1=CC=CC=C1)C1=CC=CC=C1)=O AJGADVRXPVDAHX-UHFFFAOYSA-N 0.000 claims 1
• OVUYDSQXBSXEKO-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(1-propan-2-ylpyrazol-4-yl)pyridin-2-one Chemical compound C(C)(C)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=CC=C1 OVUYDSQXBSXEKO-UHFFFAOYSA-N 0.000 claims 1
• RUANSQZGQITTMQ-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(1-propylpyrazol-4-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)CCC)C1=CC=CC=C1)=O RUANSQZGQITTMQ-UHFFFAOYSA-N 0.000 claims 1
• RNGHGTWCHYKQMI-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(1H-pyrazol-4-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NNC=1)C1=CC=CC=C1)=O RNGHGTWCHYKQMI-UHFFFAOYSA-N 0.000 claims 1
• MPHMMKMEFMUCPY-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(2-phenyl-1,3-oxazol-4-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1N=C(OC=1)C1=CC=CC=C1)C1=CC=CC=C1)=O MPHMMKMEFMUCPY-UHFFFAOYSA-N 0.000 claims 1
• YBTINYLTXXXTAF-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(2-phenyl-1,3-oxazol-5-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C1=CN=C(O1)C1=CC=CC=C1)C1=CC=CC=C1)=O YBTINYLTXXXTAF-UHFFFAOYSA-N 0.000 claims 1
• FVYKDNOAEDISTK-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(5-phenyl-1,3-oxazol-2-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1OC(=CN=1)C1=CC=CC=C1)C1=CC=CC=C1)=O FVYKDNOAEDISTK-UHFFFAOYSA-N 0.000 claims 1
• OWXIJBYONQTCFZ-UHFFFAOYSA-N 1-methyl-5-(1-methyl-5-phenylpyrazol-3-yl)-4-phenylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C1=NN(C(=C1)C1=CC=CC=C1)C)C1=CC=CC=C1)=O OWXIJBYONQTCFZ-UHFFFAOYSA-N 0.000 claims 1
• LRIXCPUZXKEYAS-UHFFFAOYSA-N 1-methyl-5-(1-methylpyrazol-4-yl)-4-phenylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C)C1=CC=CC=C1)=O LRIXCPUZXKEYAS-UHFFFAOYSA-N 0.000 claims 1
• APPRPBPCJDGZRL-UHFFFAOYSA-N 1-methyl-5-[1-(1-methylsulfonylpiperidin-4-yl)pyrazol-4-yl]-4-phenylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C1CCN(CC1)S(=O)(=O)C)C1=CC=CC=C1)=O APPRPBPCJDGZRL-UHFFFAOYSA-N 0.000 claims 1
• XEKGESHSCFHZRB-UHFFFAOYSA-N 1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]-4-phenylmethoxypyridin-2-one Chemical compound C(C1=CC=CC=C1)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O XEKGESHSCFHZRB-UHFFFAOYSA-N 0.000 claims 1
• UXAYTFVXOIDWOP-UHFFFAOYSA-N 1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]-4-propan-2-yloxypyridin-2-one Chemical compound C(C)(C)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O UXAYTFVXOIDWOP-UHFFFAOYSA-N 0.000 claims 1
• AVTRHNKCJKDGPZ-UHFFFAOYSA-N 1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]-4-pyrazol-1-ylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)N1N=CC=C1)=O AVTRHNKCJKDGPZ-UHFFFAOYSA-N 0.000 claims 1
• VLBHAFKKGCSTGF-UHFFFAOYSA-N 1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]-4-pyrrolidin-1-ylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)N1CCCC1)=O VLBHAFKKGCSTGF-UHFFFAOYSA-N 0.000 claims 1
• MHECQGJNIIBSGM-UHFFFAOYSA-N 1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=CC(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)=O MHECQGJNIIBSGM-UHFFFAOYSA-N 0.000 claims 1
• NQWHXBGRWRCCCV-UHFFFAOYSA-N 1-methyl-5-[1-(1-pyridin-3-ylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=CC(=C1)C=1C=NN(C=1)C(C)C=1C=NC=CC=1)=O NQWHXBGRWRCCCV-UHFFFAOYSA-N 0.000 claims 1
• NSECVCZJTZRSIU-UHFFFAOYSA-N 1-methyl-5-[1-(1-pyridin-4-ylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C=CC(=C1)C=1C=NN(C=1)C(C)C1=CC=NC=C1)=O NSECVCZJTZRSIU-UHFFFAOYSA-N 0.000 claims 1
• LORKLVCLTOMUMC-UHFFFAOYSA-N 1-methyl-5-[1-(2-methylpropyl)pyrazol-4-yl]-4-phenylpyridin-2-one Chemical compound C(C(C)C)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=CC=C1 LORKLVCLTOMUMC-UHFFFAOYSA-N 0.000 claims 1
• LNTYCWKWSFEVMT-UHFFFAOYSA-N 1-methyl-5-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-4-phenylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)CCN1CCOCC1)C1=CC=CC=C1)=O LNTYCWKWSFEVMT-UHFFFAOYSA-N 0.000 claims 1
• ANMPNNXLZNXGSC-UHFFFAOYSA-N 1-methyl-5-[1-(methylsulfonylmethyl)pyrazol-4-yl]-4-phenylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)CS(=O)(=O)C)C1=CC=CC=C1)=O ANMPNNXLZNXGSC-UHFFFAOYSA-N 0.000 claims 1
• IYKSOEJUUCDMFK-UHFFFAOYSA-N 1-methyl-5-[1-(oxan-4-yl)pyrazol-4-yl]-4-phenylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C1CCOCC1)C1=CC=CC=C1)=O IYKSOEJUUCDMFK-UHFFFAOYSA-N 0.000 claims 1
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• QYGRPFFEZAEKDO-UHFFFAOYSA-N 2-[4-[4-(4-chlorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-N-cyanobenzamide Chemical compound ClC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C(=O)NC#N)C=CC=C1 QYGRPFFEZAEKDO-UHFFFAOYSA-N 0.000 claims 1
• NTRZAYWEOIPNCI-UHFFFAOYSA-N 2-[4-[4-(4-chlorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzoic acid Chemical compound ClC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C(=O)O)C=CC=C1 NTRZAYWEOIPNCI-UHFFFAOYSA-N 0.000 claims 1
• OXRQKWBVSUZGRL-UHFFFAOYSA-N 2-[4-[4-(4-chlorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC=C1 OXRQKWBVSUZGRL-UHFFFAOYSA-N 0.000 claims 1
• ANLFZCCZUKEVAA-UHFFFAOYSA-N 2-[4-[4-(4-fluorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-4-methoxybenzoic acid Chemical compound FC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C(=O)O)C=CC(=C1)OC ANLFZCCZUKEVAA-UHFFFAOYSA-N 0.000 claims 1
• ZYHWXJKZIKRRFT-UHFFFAOYSA-N 2-[4-[4-(4-fluorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-4-methoxybenzonitrile Chemical compound FC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC(=C1)OC ZYHWXJKZIKRRFT-UHFFFAOYSA-N 0.000 claims 1
• WPJUZQCYFGOQLV-UHFFFAOYSA-N 2-[4-[4-(4-fluorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzoic acid Chemical compound FC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C(=O)O)C=CC=C1 WPJUZQCYFGOQLV-UHFFFAOYSA-N 0.000 claims 1
• FNKFNHSEVMYKOM-UHFFFAOYSA-N 2-[4-[4-(4-fluorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC=C1 FNKFNHSEVMYKOM-UHFFFAOYSA-N 0.000 claims 1
• WVFWDRVBCHKBQZ-UHFFFAOYSA-N 2-[4-[4-(4-methoxyphenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzoic acid Chemical compound COC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C(=O)O)C=CC=C1 WVFWDRVBCHKBQZ-UHFFFAOYSA-N 0.000 claims 1
• SJEWUPYDAMZCJN-UHFFFAOYSA-N 2-[4-[4-(4-methoxyphenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound COC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC=C1 SJEWUPYDAMZCJN-UHFFFAOYSA-N 0.000 claims 1
• MIHIPPGUGJCMKI-UHFFFAOYSA-N 2-[4-[4-(5-fluoro-6-oxo-1H-pyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=CC(=CNC1=O)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC=C1 MIHIPPGUGJCMKI-UHFFFAOYSA-N 0.000 claims 1
• FYOJKILXNLIBKA-UHFFFAOYSA-N 2-[4-[4-(6-cyclopentyloxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound C1(CCCC1)OC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F FYOJKILXNLIBKA-UHFFFAOYSA-N 0.000 claims 1
• CLYWQZHEWZWWMX-UHFFFAOYSA-N 2-[4-[4-(6-cyclopropyloxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound C1(CC1)OC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F CLYWQZHEWZWWMX-UHFFFAOYSA-N 0.000 claims 1
• CJXAMGQZFYJEGD-UHFFFAOYSA-N 2-[4-[4-(6-cyclopropylpyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound C1(CC1)C1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F CJXAMGQZFYJEGD-UHFFFAOYSA-N 0.000 claims 1
• NPFXNMLZUGYMOO-UHFFFAOYSA-N 2-[4-[4-(6-ethoxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-4-methoxybenzoic acid Chemical compound C(C)OC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C(=O)O)C=CC(=C1)OC NPFXNMLZUGYMOO-UHFFFAOYSA-N 0.000 claims 1
• KSPAZGZBZAGORM-UHFFFAOYSA-N 2-[4-[4-(6-ethoxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-4-methoxybenzonitrile Chemical compound C(C)OC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC(=C1)OC KSPAZGZBZAGORM-UHFFFAOYSA-N 0.000 claims 1
• YASYDEIFHPAKSO-UHFFFAOYSA-N 2-[4-[4-(6-ethoxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzoic acid Chemical compound C(C)OC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C(=O)O)C=CC=C1 YASYDEIFHPAKSO-UHFFFAOYSA-N 0.000 claims 1
• GUTAAVLCESSEQT-UHFFFAOYSA-N 2-[4-[4-(6-ethoxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C(C)OC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC=C1 GUTAAVLCESSEQT-UHFFFAOYSA-N 0.000 claims 1
• RINPLWZWUDGPGU-UHFFFAOYSA-N 2-[4-[4-[2-(2-methoxyethylamino)pyrimidin-5-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound COCCNC1=NC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC=C1 RINPLWZWUDGPGU-UHFFFAOYSA-N 0.000 claims 1
• LRGADKFKDSBTAM-UHFFFAOYSA-N 2-[4-[4-[2-(ethylamino)pyrimidin-5-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C(C)NC1=NC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C=CC=C1 LRGADKFKDSBTAM-UHFFFAOYSA-N 0.000 claims 1
• JKMNFSLYTMFKFP-UHFFFAOYSA-N 2-[4-[4-[6-(cyclopentylamino)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound C1(CCCC1)NC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F JKMNFSLYTMFKFP-UHFFFAOYSA-N 0.000 claims 1
• ZCYMIVMSGILCCD-UHFFFAOYSA-N 2-[4-[4-[6-(cyclopropylmethylamino)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound C1(CC1)CNC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F ZCYMIVMSGILCCD-UHFFFAOYSA-N 0.000 claims 1
• VBSYPAHQYIPCHS-UHFFFAOYSA-N 2-[4-[4-[6-(difluoromethoxy)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound FC(OC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F)F VBSYPAHQYIPCHS-UHFFFAOYSA-N 0.000 claims 1
• LQVNBOXLLLITNV-UHFFFAOYSA-N 2-[4-[4-[6-(dimethylamino)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound CN(C1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F)C LQVNBOXLLLITNV-UHFFFAOYSA-N 0.000 claims 1
• VFNLAXZQXFTOFS-UHFFFAOYSA-N 2-[4-[4-[6-(ethylamino)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-6-fluorobenzonitrile Chemical compound C(C)NC1=CC=C(C=N1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F VFNLAXZQXFTOFS-UHFFFAOYSA-N 0.000 claims 1
• MKVRSIJHUXLOLF-UHFFFAOYSA-N 2-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]oxyacetonitrile Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)OCC#N MKVRSIJHUXLOLF-UHFFFAOYSA-N 0.000 claims 1
• SDSKDUYQDNVDAW-UHFFFAOYSA-N 2-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]sulfanylacetic acid Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)SCC(=O)O SDSKDUYQDNVDAW-UHFFFAOYSA-N 0.000 claims 1
• WEBQGNRWPQEGEL-UHFFFAOYSA-N 2-[[4-(1-methyl-6-oxopyridin-3-yl)pyrazol-1-yl]methyl]benzonitrile Chemical compound CN1C=C(C=CC1=O)C=1C=NN(C=1)CC1=C(C#N)C=CC=C1 WEBQGNRWPQEGEL-UHFFFAOYSA-N 0.000 claims 1
• RSHAARUZZSBOEO-UHFFFAOYSA-N 2-chloro-6-[4-(4-ethoxy-1-methyl-6-oxopyridin-3-yl)pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1OCC)=O)C RSHAARUZZSBOEO-UHFFFAOYSA-N 0.000 claims 1
• DAWYEIUKGAWGOH-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-4-(1-methyl-2-oxopyridin-4-yl)-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C1=CC(N(C=C1)C)=O)=O)C DAWYEIUKGAWGOH-UHFFFAOYSA-N 0.000 claims 1
• WQAOKTLAMXTRBM-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-4-(2-morpholin-4-ylpyrimidin-5-yl)-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=NC=1)N1CCOCC1)=O)C WQAOKTLAMXTRBM-UHFFFAOYSA-N 0.000 claims 1
• NBQPWOJODLVTFL-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-4-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=NC=1)N1CCN(CC1)C)=O)C NBQPWOJODLVTFL-UHFFFAOYSA-N 0.000 claims 1
• AFGKFFSNVWAXDV-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-4-[6-(methylamino)pyridin-3-yl]-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)NC)=O)C AFGKFFSNVWAXDV-UHFFFAOYSA-N 0.000 claims 1
• JOTYWDBOKWNPRP-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-6-oxo-4-(2-piperidin-1-ylpyrimidin-5-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=NC=1)N1CCCCC1)=O)C JOTYWDBOKWNPRP-UHFFFAOYSA-N 0.000 claims 1
• DPLFLMJLSMMYIO-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-6-oxo-4-(2-pyrrolidin-1-ylpyrimidin-5-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=NC=1)N1CCCC1)=O)C DPLFLMJLSMMYIO-UHFFFAOYSA-N 0.000 claims 1
• BAABYMPGLFUCSV-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-6-oxo-4-(6-propan-2-yloxypyridin-3-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OC(C)C)=O)C BAABYMPGLFUCSV-UHFFFAOYSA-N 0.000 claims 1
• HTENJBGQECUQAI-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-6-oxo-4-(6-propan-2-ylpyridin-3-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)C(C)C)=O)C HTENJBGQECUQAI-UHFFFAOYSA-N 0.000 claims 1
• NMHZRNWYVZAGLC-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-6-oxo-4-[6-(propan-2-ylamino)pyridin-3-yl]pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)NC(C)C)=O)C NMHZRNWYVZAGLC-UHFFFAOYSA-N 0.000 claims 1
• CWDSXRCRIDNQHY-UHFFFAOYSA-N 2-chloro-6-[4-[1-methyl-6-oxo-4-[6-(trifluoromethyl)pyridin-3-yl]pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)C(F)(F)F)=O)C CWDSXRCRIDNQHY-UHFFFAOYSA-N 0.000 claims 1
• FILPTCKFIANJKL-UHFFFAOYSA-N 2-chloro-6-[4-[4-(2-ethylpyrimidin-5-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=NC=1)CC)=O)C FILPTCKFIANJKL-UHFFFAOYSA-N 0.000 claims 1
• QRLZGHHFMRXNRS-UHFFFAOYSA-N 2-chloro-6-[4-[4-(6-cyclopentyloxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OC1CCCC1)=O)C QRLZGHHFMRXNRS-UHFFFAOYSA-N 0.000 claims 1
• ZGRSPNZGQSLCIR-UHFFFAOYSA-N 2-chloro-6-[4-[4-(6-cyclopentylpyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)C1CCCC1)=O)C ZGRSPNZGQSLCIR-UHFFFAOYSA-N 0.000 claims 1
• RFCVZUGBPXSRBH-UHFFFAOYSA-N 2-chloro-6-[4-[4-(6-cyclopropyloxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OC1CC1)=O)C RFCVZUGBPXSRBH-UHFFFAOYSA-N 0.000 claims 1
• WWPVKCSUKBBDDS-UHFFFAOYSA-N 2-chloro-6-[4-[4-(6-cyclopropylpyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)C1CC1)=O)C WWPVKCSUKBBDDS-UHFFFAOYSA-N 0.000 claims 1
• NATZYGXIDSQDEQ-UHFFFAOYSA-N 2-chloro-6-[4-[4-(6-ethoxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OCC)=O)C NATZYGXIDSQDEQ-UHFFFAOYSA-N 0.000 claims 1
• DEWQGAQNABGJKV-UHFFFAOYSA-N 2-chloro-6-[4-[4-(6-ethylpyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)CC)=O)C DEWQGAQNABGJKV-UHFFFAOYSA-N 0.000 claims 1
• AQUBZNJENHAPCR-UHFFFAOYSA-N 2-chloro-6-[4-[4-[2-(2-methoxyethylamino)pyrimidin-5-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=NC=1)NCCOC)=O)C AQUBZNJENHAPCR-UHFFFAOYSA-N 0.000 claims 1
• BYOCWONXXIJAPO-UHFFFAOYSA-N 2-chloro-6-[4-[4-[6-(cyclopentylamino)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)NC1CCCC1)=O)C BYOCWONXXIJAPO-UHFFFAOYSA-N 0.000 claims 1
• GTDGTGOYLYDVED-UHFFFAOYSA-N 2-chloro-6-[4-[4-[6-(cyclopropylmethoxy)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OCC1CC1)=O)C GTDGTGOYLYDVED-UHFFFAOYSA-N 0.000 claims 1
• XGHBZEAWMCZEMS-UHFFFAOYSA-N 2-chloro-6-[4-[4-[6-(dimethylamino)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)N(C)C)=O)C XGHBZEAWMCZEMS-UHFFFAOYSA-N 0.000 claims 1
• ZRGFIIZXQBSLAH-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[1-methyl-4-(1-methyl-2-oxopyridin-4-yl)-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C1=CC(N(C=C1)C)=O)=O)C ZRGFIIZXQBSLAH-UHFFFAOYSA-N 0.000 claims 1
• WPWRCNQOQBJYRY-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[1-methyl-6-oxo-4-(2-oxo-1-propylpyridin-4-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C1=CC(N(C=C1)CCC)=O)=O)C WPWRCNQOQBJYRY-UHFFFAOYSA-N 0.000 claims 1
• UKMKWGZCYZJTIS-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[4-(1-ethyl-2-oxopyridin-4-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C1=CC(N(C=C1)CC)=O)=O)C UKMKWGZCYZJTIS-UHFFFAOYSA-N 0.000 claims 1
• FNZMRDNVSLJQEQ-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[4-(6-ethoxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OCC)=O)C FNZMRDNVSLJQEQ-UHFFFAOYSA-N 0.000 claims 1
• NMMUVOFNAMMIPQ-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[4-(6-methoxypyridin-3-yl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OC)=O)C NMMUVOFNAMMIPQ-UHFFFAOYSA-N 0.000 claims 1
• VUVLGZLCRRDDSJ-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[4-[1-(cyclopropylmethyl)-2-oxopyridin-4-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C1=CC(N(C=C1)CC1CC1)=O)=O)C VUVLGZLCRRDDSJ-UHFFFAOYSA-N 0.000 claims 1
• UCEJTNHZEPDTDT-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[4-[6-(cyclopropylmethoxy)pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OCC1CC1)=O)C UCEJTNHZEPDTDT-UHFFFAOYSA-N 0.000 claims 1
• LQSVJLWKMOSGOU-UHFFFAOYSA-N 2-cyclopropyl-6-[4-[4-[6-[3-(dimethylamino)propoxy]pyridin-3-yl]-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)C1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OCCCN(C)C)=O)C LQSVJLWKMOSGOU-UHFFFAOYSA-N 0.000 claims 1
• VUFQCOXQRPBVAE-UHFFFAOYSA-N 2-fluoro-6-[4-[1-methyl-4-(1-methyl-2-oxopyridin-4-yl)-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound CN1C=C(C(=CC1=O)C1=CC(N(C=C1)C)=O)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F VUFQCOXQRPBVAE-UHFFFAOYSA-N 0.000 claims 1
• UXSZQFWQBIZLLP-UHFFFAOYSA-N 2-fluoro-6-[4-[1-methyl-4-(6-methylpyridin-3-yl)-6-oxopyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound CN1C=C(C(=CC1=O)C=1C=NC(=CC=1)C)C=1C=NN(C=1)C1=C(C#N)C(=CC=C1)F UXSZQFWQBIZLLP-UHFFFAOYSA-N 0.000 claims 1
• POIXCJGOIHKSFM-UHFFFAOYSA-N 2-fluoro-6-[4-[1-methyl-6-oxo-4-(2-pyrrolidin-1-ylpyrimidin-5-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=NC=1)N1CCCC1)=O)C POIXCJGOIHKSFM-UHFFFAOYSA-N 0.000 claims 1
• VVGNAAUBXUSZBE-UHFFFAOYSA-N 2-fluoro-6-[4-[1-methyl-6-oxo-4-(6-propan-2-yloxypyridin-3-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)OC(C)C)=O)C VVGNAAUBXUSZBE-UHFFFAOYSA-N 0.000 claims 1
• FYKUZMCSLKOQCF-UHFFFAOYSA-N 2-fluoro-6-[4-[1-methyl-6-oxo-4-(6-propan-2-ylpyridin-3-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)C(C)C)=O)C FYKUZMCSLKOQCF-UHFFFAOYSA-N 0.000 claims 1
• QCFBXFJSAUTGBX-UHFFFAOYSA-N 2-fluoro-6-[4-[1-methyl-6-oxo-4-(6-pyrrolidin-1-ylpyridin-3-yl)pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)N1CCCC1)=O)C QCFBXFJSAUTGBX-UHFFFAOYSA-N 0.000 claims 1
• UHGOIJAVNHHCNN-UHFFFAOYSA-N 2-fluoro-6-[4-[1-methyl-6-oxo-4-[6-(trifluoromethyl)pyridin-3-yl]pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=C(C#N)C(=CC=C1)N1N=CC(=C1)C1=CN(C(C=C1C=1C=NC(=CC=1)C(F)(F)F)=O)C UHGOIJAVNHHCNN-UHFFFAOYSA-N 0.000 claims 1
• MNYBCXOBUOYSLQ-UHFFFAOYSA-N 2-methyl-4-[1-(1-phenylethyl)pyrazol-4-yl]-6,7-dihydro-5H-cyclopenta[c]pyridin-1-one Chemical compound CN1C(C2=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)CCC2)=O MNYBCXOBUOYSLQ-UHFFFAOYSA-N 0.000 claims 1
• HXYOLZKAEKSSDS-UHFFFAOYSA-N 3-(dimethylamino)-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN(C=1C(N(C=C(C=1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O)C HXYOLZKAEKSSDS-UHFFFAOYSA-N 0.000 claims 1
• OEAAAARRDHHNPZ-UHFFFAOYSA-N 3-[1-[4-(1-methyl-6-oxopyridin-3-yl)pyrazol-1-yl]ethyl]benzonitrile Chemical compound CN1C=C(C=CC1=O)C=1C=NN(C=1)C(C)C=1C=C(C#N)C=CC=1 OEAAAARRDHHNPZ-UHFFFAOYSA-N 0.000 claims 1
• OTBNZNLRCFOCSM-UHFFFAOYSA-N 3-[4-(4-ethoxy-1-methyl-6-oxopyridin-3-yl)pyrazol-1-yl]benzonitrile Chemical compound C(C)OC=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C=1C=C(C#N)C=CC=1 OTBNZNLRCFOCSM-UHFFFAOYSA-N 0.000 claims 1
• GWBVHJMEEZKTIF-UHFFFAOYSA-N 3-[4-[4-(4-chlorophenyl)-1-methyl-6-oxopyridin-3-yl]pyrazol-1-yl]-4-methoxybenzonitrile Chemical compound ClC1=CC=C(C=C1)C=1C(=CN(C(C=1)=O)C)C=1C=NN(C=1)C=1C=C(C#N)C=CC=1OC GWBVHJMEEZKTIF-UHFFFAOYSA-N 0.000 claims 1
• PTUAKYUPEGWKQA-UHFFFAOYSA-N 3-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]oxypropanoic acid Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)OCCC(=O)O PTUAKYUPEGWKQA-UHFFFAOYSA-N 0.000 claims 1
• ANRUXZIMGMJPDS-UHFFFAOYSA-N 3-[[4-(1-methyl-6-oxopyridin-3-yl)pyrazol-1-yl]methyl]benzonitrile Chemical compound CN1C=C(C=CC1=O)C=1C=NN(C=1)CC=1C=C(C#N)C=CC=1 ANRUXZIMGMJPDS-UHFFFAOYSA-N 0.000 claims 1
• PEINRKPDDQWDRM-UHFFFAOYSA-N 3-[[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]amino]propanoic acid Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)NCCC(=O)O PEINRKPDDQWDRM-UHFFFAOYSA-N 0.000 claims 1
• LMSPINBPGAWAOJ-UHFFFAOYSA-N 3-chloro-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound ClC=1C(N(C=C(C=1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O LMSPINBPGAWAOJ-UHFFFAOYSA-N 0.000 claims 1
• UGCNMJAMBOSYGK-UHFFFAOYSA-N 3-cyclopropyl-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C1(CC1)C=1C(N(C=C(C=1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O UGCNMJAMBOSYGK-UHFFFAOYSA-N 0.000 claims 1
• XIVYKATVKVWQLB-UHFFFAOYSA-N 3-fluoro-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound FC=1C(N(C=C(C=1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O XIVYKATVKVWQLB-UHFFFAOYSA-N 0.000 claims 1
• ASXXLNGYDCPOQR-UHFFFAOYSA-N 3-methoxy-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound COC=1C(N(C=C(C=1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O ASXXLNGYDCPOQR-UHFFFAOYSA-N 0.000 claims 1
• YTEIHWVCQJZNEN-UHFFFAOYSA-N 3-pyridin-4-ylpyridine Chemical compound C1=CN=CC(C=2C=CN=CC=2)=C1 YTEIHWVCQJZNEN-UHFFFAOYSA-N 0.000 claims 1
• YPDMSNLWSYMBBC-UHFFFAOYSA-N 4-(1-acetylazetidin-3-yl)oxy-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C(C)(=O)N1CC(C1)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O YPDMSNLWSYMBBC-UHFFFAOYSA-N 0.000 claims 1
• CQDISTYJHAUKNN-UHFFFAOYSA-N 4-(1-benzylpyrazol-4-yl)-2-methylisoquinolin-1-one Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C1=CN(C(C2=CC=CC=C12)=O)C CQDISTYJHAUKNN-UHFFFAOYSA-N 0.000 claims 1
• QPKFFDPETIUGHC-UHFFFAOYSA-N 4-(3-methoxyazetidin-1-yl)-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound COC1CN(C1)C1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O QPKFFDPETIUGHC-UHFFFAOYSA-N 0.000 claims 1
• GNWGEXFCZAIQLR-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-methyl-5-[1-(2-methylsulfonylphenyl)pyrazol-4-yl]pyridin-2-one Chemical compound ClC1=CC=C(C=C1)C1=CC(N(C=C1C=1C=NN(C=1)C1=C(C=CC=C1)S(=O)(=O)C)C)=O GNWGEXFCZAIQLR-UHFFFAOYSA-N 0.000 claims 1
• BISKCBBDIBKLKN-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-methyl-5-[1-[2-(2H-tetrazol-5-yl)phenyl]pyrazol-4-yl]pyridin-2-one Chemical compound N1N=NN=C1C1=C(C=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C=C1)Cl BISKCBBDIBKLKN-UHFFFAOYSA-N 0.000 claims 1
• WOJURGXCDHQZCV-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[1-(cyclopropylmethyl)pyrazol-4-yl]-1-methylpyridin-2-one Chemical compound ClC1=CC=C(C=C1)C1=CC(N(C=C1C=1C=NN(C=1)CC1CC1)C)=O WOJURGXCDHQZCV-UHFFFAOYSA-N 0.000 claims 1
• SLJKVPQYTQLMOK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-methyl-5-[1-[2-(2H-tetrazol-5-yl)phenyl]pyrazol-4-yl]pyridin-2-one Chemical compound FC1=CC=C(C=C1)C1=CC(N(C=C1C=1C=NN(C=1)C1=C(C=CC=C1)C1=NN=NN1)C)=O SLJKVPQYTQLMOK-UHFFFAOYSA-N 0.000 claims 1
• KEGQJUMXRVTPLW-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1-methyl-5-[1-[2-(2H-tetrazol-5-yl)phenyl]pyrazol-4-yl]pyridin-2-one Chemical compound COC1=CC=C(C=C1)C1=CC(N(C=C1C=1C=NN(C=1)C1=C(C=CC=C1)C1=NN=NN1)C)=O KEGQJUMXRVTPLW-UHFFFAOYSA-N 0.000 claims 1
• JWXPNSOGEYDHMF-UHFFFAOYSA-N 4-(6-methoxypyridin-3-yl)-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound COC1=CC=C(C=N1)C1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O JWXPNSOGEYDHMF-UHFFFAOYSA-N 0.000 claims 1
• GHFWFOVPTYLWBX-UHFFFAOYSA-N 4-(azetidin-1-yl)-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound N1(CCC1)C1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O GHFWFOVPTYLWBX-UHFFFAOYSA-N 0.000 claims 1
• BULSNLQMQJIDIO-UHFFFAOYSA-N 4-[1-[4-(1-methyl-6-oxopyridin-3-yl)pyrazol-1-yl]ethyl]benzonitrile Chemical compound CN1C=C(C=CC1=O)C=1C=NN(C=1)C(C)C1=CC=C(C#N)C=C1 BULSNLQMQJIDIO-UHFFFAOYSA-N 0.000 claims 1
• CTUYRFAIQJTOAJ-UHFFFAOYSA-N 4-[2-(ethylamino)pyrimidin-5-yl]-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C(C)NC1=NC=C(C=N1)C1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O CTUYRFAIQJTOAJ-UHFFFAOYSA-N 0.000 claims 1
• VNIDHPOABZFVMM-UHFFFAOYSA-N 4-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]benzoic acid Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C(=O)O)C=C1 VNIDHPOABZFVMM-UHFFFAOYSA-N 0.000 claims 1
• DTKVOVOUCUQOQA-UHFFFAOYSA-N 4-[5-(1-benzylpyrazol-4-yl)-1-methyl-2-oxopyridin-4-yl]benzonitrile Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C#N)C=C1 DTKVOVOUCUQOQA-UHFFFAOYSA-N 0.000 claims 1
• UUOZEMXSORQCFS-UHFFFAOYSA-N 4-[5-[1-(2-cyanophenyl)pyrazol-4-yl]-1-methyl-2-oxopyridin-4-yl]-N-methylbenzamide Chemical compound C(#N)C1=C(C=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C(=O)NC)C=C1 UUOZEMXSORQCFS-UHFFFAOYSA-N 0.000 claims 1
• JBOBZZJUHOJYAJ-UHFFFAOYSA-N 4-[5-[1-(2-cyanophenyl)pyrazol-4-yl]-1-methyl-2-oxopyridin-4-yl]benzamide Chemical compound C(#N)C1=C(C=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C(=O)N)C=C1 JBOBZZJUHOJYAJ-UHFFFAOYSA-N 0.000 claims 1
• YMLYTVOMNKLLEY-UHFFFAOYSA-N 4-[5-[1-(2-cyanophenyl)pyrazol-4-yl]-1-methyl-2-oxopyridin-4-yl]benzoic acid Chemical compound C(#N)C1=C(C=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C(=O)O)C=C1 YMLYTVOMNKLLEY-UHFFFAOYSA-N 0.000 claims 1
• ZMLUYPLCIMZVPH-UHFFFAOYSA-N 4-[5-[1-(cyclopropylmethyl)pyrazol-4-yl]-1-methyl-2-oxopyridin-4-yl]-N-methylbenzamide Chemical compound C1(CC1)CN1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C(=O)NC)C=C1 ZMLUYPLCIMZVPH-UHFFFAOYSA-N 0.000 claims 1
• MENSFUIYULEWCN-UHFFFAOYSA-N 4-[5-[1-(cyclopropylmethyl)pyrazol-4-yl]-1-methyl-2-oxopyridin-4-yl]benzoic acid Chemical compound C1(CC1)CN1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C(=O)O)C=C1 MENSFUIYULEWCN-UHFFFAOYSA-N 0.000 claims 1
• UBRVWAKLGVVUNM-UHFFFAOYSA-N 4-[5-[1-(cyclopropylmethyl)pyrazol-4-yl]-1-methyl-2-oxopyridin-4-yl]benzonitrile Chemical compound C1(CC1)CN1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC=C(C#N)C=C1 UBRVWAKLGVVUNM-UHFFFAOYSA-N 0.000 claims 1
• PEVYMWIDKRAPNV-UHFFFAOYSA-N 4-[6-[3-(dimethylamino)propoxy]pyridin-3-yl]-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN(CCCOC1=CC=C(C=N1)C1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O)C PEVYMWIDKRAPNV-UHFFFAOYSA-N 0.000 claims 1
• RTXPXKRDNYOUPQ-UHFFFAOYSA-N 4-amino-5-(1-benzylpyrazol-4-yl)-1-methylpyridin-2-one Chemical compound NC1=CC(N(C=C1C=1C=NN(C=1)CC1=CC=CC=C1)C)=O RTXPXKRDNYOUPQ-UHFFFAOYSA-N 0.000 claims 1
• CBUYISHIFQEYJS-UHFFFAOYSA-N 4-chloro-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound ClC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O CBUYISHIFQEYJS-UHFFFAOYSA-N 0.000 claims 1
• RCBAQDREMNGMIP-UHFFFAOYSA-N 4-cyclobutyloxy-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C1(CCC1)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O RCBAQDREMNGMIP-UHFFFAOYSA-N 0.000 claims 1
• AOBZXALFRMAZPZ-UHFFFAOYSA-N 4-cyclohexyl-1-methyl-5-(1-methylpyrazol-4-yl)pyridin-2-one Chemical compound C1(CCCCC1)C1=CC(N(C=C1C=1C=NN(C=1)C)C)=O AOBZXALFRMAZPZ-UHFFFAOYSA-N 0.000 claims 1
• QESLLXFWXSJNKB-UHFFFAOYSA-N 4-cyclohexyloxy-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C1(CCCCC1)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O QESLLXFWXSJNKB-UHFFFAOYSA-N 0.000 claims 1
• GGZNMNKSJCNWCT-UHFFFAOYSA-N 4-cyclopentyl-1-methyl-5-(1-methylpyrazol-4-yl)pyridin-2-one Chemical compound C1(CCCC1)C1=CC(N(C=C1C=1C=NN(C=1)C)C)=O GGZNMNKSJCNWCT-UHFFFAOYSA-N 0.000 claims 1
• CGCFIUWKFNSLAP-UHFFFAOYSA-N 4-cyclopentyloxy-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C1(CCCC1)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O CGCFIUWKFNSLAP-UHFFFAOYSA-N 0.000 claims 1
• RKAPMMHVIIIODM-UHFFFAOYSA-N 4-cyclopropyl-1-methyl-5-(1-methylpyrazol-4-yl)pyridin-2-one Chemical compound C1(CC1)C1=CC(N(C=C1C=1C=NN(C=1)C)C)=O RKAPMMHVIIIODM-UHFFFAOYSA-N 0.000 claims 1
• VJPGAPVHTICUKL-UHFFFAOYSA-N 4-cyclopropyl-1-methyl-5-[1-[2-(2H-tetrazol-5-yl)phenyl]pyrazol-4-yl]pyridin-2-one Chemical compound C1(CC1)C1=CC(N(C=C1C=1C=NN(C=1)C1=C(C=CC=C1)C1=NN=NN1)C)=O VJPGAPVHTICUKL-UHFFFAOYSA-N 0.000 claims 1
• FMFQNDVKDMENKX-UHFFFAOYSA-N 4-cyclopropyloxy-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound C1(CC1)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O FMFQNDVKDMENKX-UHFFFAOYSA-N 0.000 claims 1
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• PIMIMIZDTGPIHP-UHFFFAOYSA-N 4-cyclopropyloxy-2-[4-(4-ethoxy-1-methyl-6-oxopyridin-3-yl)pyrazol-1-yl]benzonitrile Chemical compound C1(CC1)OC1=CC(=C(C#N)C=C1)N1N=CC(=C1)C1=CN(C(C=C1OCC)=O)C PIMIMIZDTGPIHP-UHFFFAOYSA-N 0.000 claims 1
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