KR102457933B1 - Rock의 억제제로서의 트리아졸론 및 테트라졸론 - Google Patents

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Publication number

KR102457933B1

KR102457933B1 KR1020187037221A KR20187037221A KR102457933B1 KR 102457933 B1 KR102457933 B1 KR 102457933B1 KR 1020187037221 A KR1020187037221 A KR 1020187037221A KR 20187037221 A KR20187037221 A KR 20187037221A KR 102457933 B1 KR102457933 B1 KR 102457933B1

Authority

KR

South Korea

Prior art keywords

substituted

phenyl

pyrazol

alkyl

triazol

Prior art date

2016-05-27

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.)

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• 239000011435 rock Substances 0.000 title abstract description 39
• 239000003112 inhibitor Substances 0.000 title abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 147
• 150000003839 salts Chemical class 0.000 claims abstract description 52
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 125000000217 alkyl group Chemical group 0.000 claims description 315
• 229910052739 hydrogen Inorganic materials 0.000 claims description 201
• 229910052799 carbon Inorganic materials 0.000 claims description 177
• 125000000623 heterocyclic group Chemical group 0.000 claims description 124
• 229910052801 chlorine Inorganic materials 0.000 claims description 108
• 229910052731 fluorine Inorganic materials 0.000 claims description 108
• 229910052794 bromium Inorganic materials 0.000 claims description 102
• -1 substituted Chemical class 0.000 claims description 78
• 229910052757 nitrogen Inorganic materials 0.000 claims description 76
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 60
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 45
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 31
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 12
• 206010020772 Hypertension Diseases 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 11
• 208000006011 Stroke Diseases 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• CNLAYXDKLHCQMA-UHFFFAOYSA-N 2-[4-(2-aminopyridin-4-yl)phenyl]-4-[(3-methoxyphenyl)methyl]-5-methyl-1,2,4-triazol-3-one Chemical compound NC1=NC=CC(=C1)C1=CC=C(C=C1)N1N=C(N(C1=O)CC1=CC(=CC=C1)OC)C CNLAYXDKLHCQMA-UHFFFAOYSA-N 0.000 claims description 5
• NZPUJHVXZQBLFP-UHFFFAOYSA-N 2-benzyl-5-methyl-4-[4-(1H-pyrazol-4-yl)phenyl]-1,2,4-triazol-3-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1C(=NN(C1=O)CC1=CC=CC=C1)C NZPUJHVXZQBLFP-UHFFFAOYSA-N 0.000 claims description 5
• CHUAJBPDNHOOAT-UHFFFAOYSA-N 4-benzyl-2-[4-(1H-pyrazol-4-yl)phenyl]-1,2,4-triazol-3-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=CN(C1=O)CC1=CC=CC=C1 CHUAJBPDNHOOAT-UHFFFAOYSA-N 0.000 claims description 5
• KQVZWUDGYVEWPK-UHFFFAOYSA-N 5-(hydroxymethyl)-4-[(3-methoxyphenyl)methyl]-2-[4-(1H-pyrazol-4-yl)phenyl]-1,2,4-triazol-3-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=C(N(C1=O)CC1=CC(=CC=C1)OC)CO KQVZWUDGYVEWPK-UHFFFAOYSA-N 0.000 claims description 5
• 206010019280 Heart failures Diseases 0.000 claims description 5
• HCOWWJVVBRBXBF-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-4-[4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=NN(C1=O)CC1=CC(=CC=C1)OC HCOWWJVVBRBXBF-UHFFFAOYSA-N 0.000 claims description 4
• DFSURLYNFCXQOM-UHFFFAOYSA-N 2-[(2,5-difluorophenyl)methyl]-4-[2-methoxy-4-(1H-pyrazol-4-yl)phenyl]-1,2,4-triazol-3-one Chemical compound FC1=C(CN2N=CN(C2=O)C2=C(C=C(C=C2)C=2C=NNC=2)OC)C=C(C=C1)F DFSURLYNFCXQOM-UHFFFAOYSA-N 0.000 claims description 4
• WJEJXTSVSCSNIW-UHFFFAOYSA-N 4-benzyl-5-methyl-2-[4-(1H-pyrazol-4-yl)phenyl]-1,2,4-triazol-3-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=C(N(C1=O)CC1=CC=CC=C1)C WJEJXTSVSCSNIW-UHFFFAOYSA-N 0.000 claims description 4
• 206010002383 Angina Pectoris Diseases 0.000 claims description 4
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• WIOWHADKSXUKEZ-UHFFFAOYSA-N dicyclohexyl-[3-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC(P(C2CCCCC2)C2CCCCC2)=C1 WIOWHADKSXUKEZ-UHFFFAOYSA-N 0.000 claims description 4
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 4
• 208000029078 coronary artery disease Diseases 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• SBXZSRBIFZQTFW-UHFFFAOYSA-N 1-(1-phenylethyl)-4-[4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=NN(C1=O)C(C)C1=CC=CC=C1 SBXZSRBIFZQTFW-UHFFFAOYSA-N 0.000 claims description 2
• MZHVBGWMFTZTIN-UHFFFAOYSA-N 1-[(2,5-difluorophenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound FC1=C(CN2N=NN(C2=O)C2=CC(=C(C=C2)C=2C=NNC=2)OC)C=C(C=C1)F MZHVBGWMFTZTIN-UHFFFAOYSA-N 0.000 claims description 2
• KWULMTIIAPDEDB-UHFFFAOYSA-N 1-[(2,5-difluorophenyl)methyl]-4-[4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=NN(C1=O)CC1=C(C=CC(=C1)F)F KWULMTIIAPDEDB-UHFFFAOYSA-N 0.000 claims description 2
• WRYSVXYAJBVPFV-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound FC1=C(CN2N=NN(C2=O)C2=CC(=C(C=C2)C=2C=NNC=2)OC)C(=CC=C1)F WRYSVXYAJBVPFV-UHFFFAOYSA-N 0.000 claims description 2
• HGWQMEPVCKVODS-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-4-[4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=NN(C1=O)CC1=C(C=CC=C1)Cl HGWQMEPVCKVODS-UHFFFAOYSA-N 0.000 claims description 2
• VYCJFSPNVUUXKJ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound FC1=C(CN2N=NN(C2=O)C2=CC(=C(C=C2)C=2C=NNC=2)OC)C=CC=C1 VYCJFSPNVUUXKJ-UHFFFAOYSA-N 0.000 claims description 2
• FDFIDSBCANZIPW-UHFFFAOYSA-N 1-[(3-fluoro-5-methoxyphenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound FC=1C=C(CN2N=NN(C2=O)C2=CC(=C(C=C2)C=2C=NNC=2)OC)C=C(C=1)OC FDFIDSBCANZIPW-UHFFFAOYSA-N 0.000 claims description 2
• AGOHQYODEKRYLB-UHFFFAOYSA-N 1-[(3-fluoro-5-methoxyphenyl)methyl]-4-[4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=NN(C1=O)CC1=CC(=CC(=C1)OC)F AGOHQYODEKRYLB-UHFFFAOYSA-N 0.000 claims description 2
• WBBFQRUOAIEACE-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound FC=1C=C(CN2N=NN(C2=O)C2=CC(=C(C=C2)C=2C=NNC=2)OC)C=CC=1 WBBFQRUOAIEACE-UHFFFAOYSA-N 0.000 claims description 2
• HXZNRIGBNUJHRG-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-4-[4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=NN(C1=O)CC1=CC(=CC=C1)F HXZNRIGBNUJHRG-UHFFFAOYSA-N 0.000 claims description 2
• AMOIAMLLRYOOID-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound COC=1C=C(C=CC=1C=1C=NNC=1)N1N=NN(C1=O)CC1=CC(=CC=C1)OC AMOIAMLLRYOOID-UHFFFAOYSA-N 0.000 claims description 2
• KJKGFOYVLLMZFK-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound FC1=CC=C(CN2N=NN(C2=O)C2=CC(=C(C=C2)C=2C=NNC=2)OC)C=C1 KJKGFOYVLLMZFK-UHFFFAOYSA-N 0.000 claims description 2
• MFKSHWINVZRZCI-UHFFFAOYSA-N 1-benzyl-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound C(C1=CC=CC=C1)N1N=NN(C1=O)C1=CC(=C(C=C1)C=1C=NNC=1)OC MFKSHWINVZRZCI-UHFFFAOYSA-N 0.000 claims description 2
• MKKCGQSCZYGFDF-UHFFFAOYSA-N 1-benzyl-4-[4-(1H-pyrazol-4-yl)phenyl]tetrazol-5-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1N=NN(C1=O)CC1=CC=CC=C1 MKKCGQSCZYGFDF-UHFFFAOYSA-N 0.000 claims description 2
• OPECBLKLSAMAJC-UHFFFAOYSA-N 2-(1-phenylethyl)-4-(4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound CC(C1=CC=CC=C1)N2C(=O)N(C=N2)C3=CC=C(C=C3)C4CNNC4 OPECBLKLSAMAJC-UHFFFAOYSA-N 0.000 claims description 2
• WIJFUYFJFZKXGF-UHFFFAOYSA-N 2-(3-ethyl-4-pyrazolidin-4-ylphenyl)-4-(1-phenylethyl)-1,2,4-triazol-3-one Chemical compound CCC1=C(C=CC(=C1)N2C(=O)N(C=N2)C(C)C3=CC=CC=C3)C4CNNC4 WIJFUYFJFZKXGF-UHFFFAOYSA-N 0.000 claims description 2
• QTBSWLFVOJJIAZ-UHFFFAOYSA-N 2-(3-ethyl-4-pyrazolidin-4-ylphenyl)-4-[(2-fluorophenyl)methyl]-1,2,4-triazol-3-one Chemical compound CCC1=C(C=CC(=C1)N2C(=O)N(C=N2)CC3=CC=CC=C3F)C4CNNC4 QTBSWLFVOJJIAZ-UHFFFAOYSA-N 0.000 claims description 2
• XTFMYZACZRBBDX-UHFFFAOYSA-N 2-(3-ethyl-4-pyrazolidin-4-ylphenyl)-4-[(3-fluoro-5-methoxyphenyl)methyl]-5-methyl-1,2,4-triazol-3-one Chemical compound CCC1=C(C=CC(=C1)N2C(=O)N(C(=N2)C)CC3=CC(=CC(=C3)F)OC)C4CNNC4 XTFMYZACZRBBDX-UHFFFAOYSA-N 0.000 claims description 2
• PDAZITHKSFDQJY-UHFFFAOYSA-N 2-(3-ethyl-4-pyrazolidin-4-ylphenyl)-4-[(3-methoxyphenyl)methyl]-1,2,4-triazol-3-one Chemical compound CCC1=C(C=CC(=C1)N2C(=O)N(C=N2)CC3=CC(=CC=C3)OC)C4CNNC4 PDAZITHKSFDQJY-UHFFFAOYSA-N 0.000 claims description 2
• RKMZFMAGJQZXES-UHFFFAOYSA-N 2-(3-ethyl-4-pyrazolidin-4-ylphenyl)-4-[(4-fluorophenyl)methyl]-1,2,4-triazol-3-one Chemical compound CCC1=C(C=CC(=C1)N2C(=O)N(C=N2)CC3=CC=C(C=C3)F)C4CNNC4 RKMZFMAGJQZXES-UHFFFAOYSA-N 0.000 claims description 2
• MZYOVWYDUCVRCD-UHFFFAOYSA-N 2-(3-ethyl-4-pyrazolidin-4-ylphenyl)-5-methyl-4-(2-phenylethyl)-1,2,4-triazol-3-one Chemical compound CCC1=C(C=CC(=C1)N2C(=O)N(C(=N2)C)CCC3=CC=CC=C3)C4CNNC4 MZYOVWYDUCVRCD-UHFFFAOYSA-N 0.000 claims description 2
• OIGFVWHLBMBSRW-UHFFFAOYSA-N 2-(3-methoxy-4-pyrazolidin-4-ylphenyl)-4-(1-phenylethyl)-1,2,4-triazol-3-one Chemical compound CC(C1=CC=CC=C1)N2C=NN(C2=O)C3=CC(=C(C=C3)C4CNNC4)OC OIGFVWHLBMBSRW-UHFFFAOYSA-N 0.000 claims description 2
• CXWZLKDMZLNMAL-UHFFFAOYSA-N 2-(3-methoxy-4-pyrazolidin-4-ylphenyl)-5-methyl-4-(2-phenylethyl)-1,2,4-triazol-3-one Chemical compound CC1=NN(C(=O)N1CCC2=CC=CC=C2)C3=CC(=C(C=C3)C4CNNC4)OC CXWZLKDMZLNMAL-UHFFFAOYSA-N 0.000 claims description 2
• KFLMMLCFQYWZKX-UHFFFAOYSA-N 2-[(2,5-difluorophenyl)methyl]-4-(4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound C1C(CNN1)C2=CC=C(C=C2)N3C=NN(C3=O)CC4=C(C=CC(=C4)F)F KFLMMLCFQYWZKX-UHFFFAOYSA-N 0.000 claims description 2
• RNTOFBAWHVQMQH-UHFFFAOYSA-N 2-[(2,5-difluorophenyl)methyl]-4-[2-methoxy-4-(1H-pyrazol-4-yl)phenyl]-5-methyl-1,2,4-triazol-3-one Chemical compound FC1=C(CN2N=C(N(C2=O)C2=C(C=C(C=C2)C=2C=NNC=2)OC)C)C=C(C=C1)F RNTOFBAWHVQMQH-UHFFFAOYSA-N 0.000 claims description 2
• VGIAKXLGIUYUOR-UHFFFAOYSA-N 2-[(2,5-difluorophenyl)methyl]-4-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]-5-methyl-1,2,4-triazol-3-one Chemical compound FC1=C(CN2N=C(N(C2=O)C2=CC(=C(C=C2)C=2C=NNC=2)OC)C)C=C(C=C1)F VGIAKXLGIUYUOR-UHFFFAOYSA-N 0.000 claims description 2
• XNHANSPQBOLLNM-UHFFFAOYSA-N 2-[(2,5-difluorophenyl)methyl]-5-methyl-4-[4-(1H-pyrazol-4-yl)phenyl]-1,2,4-triazol-3-one Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)N1C(=NN(C1=O)CC1=C(C=CC(=C1)F)F)C XNHANSPQBOLLNM-UHFFFAOYSA-N 0.000 claims description 2
• NRRNGRPAVIPNGT-UHFFFAOYSA-N 2-[(3-fluoro-5-methoxyphenyl)methyl]-4-(2-methoxy-4-pyrazolidin-4-ylphenyl)-5-methyl-1,2,4-triazol-3-one Chemical compound CC1=NN(C(=O)N1C2=C(C=C(C=C2)C3CNNC3)OC)CC4=CC(=CC(=C4)F)OC NRRNGRPAVIPNGT-UHFFFAOYSA-N 0.000 claims description 2
• DTDMGKPJTKVHSR-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]-4-(2-methoxy-4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound COC1=C(C=CC(=C1)C2CNNC2)N3C=NN(C3=O)CC4=CC(=CC=C4)F DTDMGKPJTKVHSR-UHFFFAOYSA-N 0.000 claims description 2
• YTKKNFVKRRWYLT-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]-4-(3-methoxy-4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound COC1=C(C=CC(=C1)N2C=NN(C2=O)CC3=CC(=CC=C3)F)C4CNNC4 YTKKNFVKRRWYLT-UHFFFAOYSA-N 0.000 claims description 2
• DJJWSUFSUWAUCA-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]-5-methyl-4-(4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound CC1=NN(C(=O)N1C2=CC=C(C=C2)C3CNNC3)CC4=CC(=CC=C4)F DJJWSUFSUWAUCA-UHFFFAOYSA-N 0.000 claims description 2
• NDRZUYBYPGHWKV-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-4-(2-methoxy-4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound COC1=CC=CC(=C1)CN2C(=O)N(C=N2)C3=C(C=C(C=C3)C4CNNC4)OC NDRZUYBYPGHWKV-UHFFFAOYSA-N 0.000 claims description 2
• NPRKWFHCLZRFSI-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-4-(3-methoxy-4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound COC1=CC=CC(=C1)CN2C(=O)N(C=N2)C3=CC(=C(C=C3)C4CNNC4)OC NPRKWFHCLZRFSI-UHFFFAOYSA-N 0.000 claims description 2
• NCHRAXLRAXBEDY-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-4-(4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound COC1=CC=CC(=C1)CN2C(=O)N(C=N2)C3=CC=C(C=C3)C4CNNC4 NCHRAXLRAXBEDY-UHFFFAOYSA-N 0.000 claims description 2
• QQAKPIHKYKICEI-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-5-methyl-4-(4-pyrazolidin-4-ylphenyl)-1,2,4-triazol-3-one Chemical compound CC1=NN(C(=O)N1C2=CC=C(C=C2)C3CNNC3)CC4=CC(=CC=C4)OC QQAKPIHKYKICEI-UHFFFAOYSA-N 0.000 claims description 2
• KJYOBVNCWRJBRH-UHFFFAOYSA-N 2-[3-ethyl-4-(1H-pyrazol-4-yl)phenyl]-4-[(2-fluorophenyl)methyl]-5-methyl-1,2,4-triazol-3-one Chemical compound C(C)C=1C=C(C=CC=1C=1C=NNC=1)N1N=C(N(C1=O)CC1=C(C=CC=C1)F)C KJYOBVNCWRJBRH-UHFFFAOYSA-N 0.000 claims description 2
• SRIVMOCNGJGBHT-UHFFFAOYSA-N 2-[3-ethyl-4-(1H-pyrazol-4-yl)phenyl]-4-[(3-fluorophenyl)methyl]-5-methyl-1,2,4-triazol-3-one Chemical compound C(C)C=1C=C(C=CC=1C=1C=NNC=1)N1N=C(N(C1=O)CC1=CC(=CC=C1)F)C SRIVMOCNGJGBHT-UHFFFAOYSA-N 0.000 claims description 2
• UDKJDEYKOOCLNI-UHFFFAOYSA-N 2-[3-ethyl-4-(1H-pyrazol-4-yl)phenyl]-4-[(3-methoxyphenyl)methyl]-5-methyl-1,2,4-triazol-3-one Chemical compound C(C)C=1C=C(C=CC=1C=1C=NNC=1)N1N=C(N(C1=O)CC1=CC(=CC=C1)OC)C UDKJDEYKOOCLNI-UHFFFAOYSA-N 0.000 claims description 2
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• GEJUGUSFDRPPRN-UHFFFAOYSA-N 2-[3-ethyl-4-(1H-pyrazol-4-yl)phenyl]-5-methyl-4-(1-phenylethyl)-1,2,4-triazol-3-one Chemical compound C(C)C=1C=C(C=CC=1C=1C=NNC=1)N1N=C(N(C1=O)C(C)C1=CC=CC=C1)C GEJUGUSFDRPPRN-UHFFFAOYSA-N 0.000 claims description 2
• CSAYDZRHVZGJIZ-UHFFFAOYSA-N 2-[3-methoxy-4-(1H-pyrazol-4-yl)phenyl]-5-methyl-4-(1-phenylethyl)-1,2,4-triazol-3-one Chemical compound COC=1C=C(C=CC=1C=1C=NNC=1)N1N=C(N(C1=O)C(C)C1=CC=CC=C1)C CSAYDZRHVZGJIZ-UHFFFAOYSA-N 0.000 claims description 2
• SRPKQFCVYVRFEW-UHFFFAOYSA-N 2-[4-(2-aminopyridin-4-yl)phenyl]-4-[(3-methoxyphenyl)methyl]-1,2,4-triazol-3-one Chemical compound NC1=NC=CC(=C1)C1=CC=C(C=C1)N1N=CN(C1=O)CC1=CC(=CC=C1)OC SRPKQFCVYVRFEW-UHFFFAOYSA-N 0.000 claims description 2
• ZKTDPAIJEHULQD-UHFFFAOYSA-N 2-[4-(2-aminopyrimidin-4-yl)phenyl]-4-[(3-methoxyphenyl)methyl]-1,2,4-triazol-3-one Chemical compound NC1=NC=CC(=N1)C1=CC=C(C=C1)N1N=CN(C1=O)CC1=CC(=CC=C1)OC ZKTDPAIJEHULQD-UHFFFAOYSA-N 0.000 claims description 2
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