JP2013505949A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013505949A5 JP2013505949A5 JP2012531061A JP2012531061A JP2013505949A5 JP 2013505949 A5 JP2013505949 A5 JP 2013505949A5 JP 2012531061 A JP2012531061 A JP 2012531061A JP 2012531061 A JP2012531061 A JP 2012531061A JP 2013505949 A5 JP2013505949 A5 JP 2013505949A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- ethoxy
- phenyl
- nitrophenyl
- dihydropyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 nitro, cyano, carboxy, carbamoyl Chemical group 0.000 claims 73
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 2
- IIDWQHVTAQYFRQ-OAQYLSRUSA-N (4r)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-pyridin-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC([C@@H]2C(=C(NC(=O)N2)C=2C=NC=CC=2)C=2C=CC=CC=2)=C1 IIDWQHVTAQYFRQ-OAQYLSRUSA-N 0.000 claims 1
- LBMFXSVJMHVNBN-QFIPXVFZSA-N (4s)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC([C@H]2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LBMFXSVJMHVNBN-QFIPXVFZSA-N 0.000 claims 1
- IIDWQHVTAQYFRQ-NRFANRHFSA-N (4s)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-pyridin-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC([C@H]2C(=C(NC(=O)N2)C=2C=NC=CC=2)C=2C=CC=CC=2)=C1 IIDWQHVTAQYFRQ-NRFANRHFSA-N 0.000 claims 1
- DONZBYIZBMQWPQ-KRWDZBQOSA-N (4s)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(1-methylpyrazol-3-yl)-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC([C@H]2C(=C(C3=NN(C)C=C3)NC(=O)N2)C2=CSC=C2)=C1 DONZBYIZBMQWPQ-KRWDZBQOSA-N 0.000 claims 1
- CKYLUTWAKNOUEY-FQEVSTJZSA-N (4s)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC([C@H]2C(=C(NC(=O)N2)C=2C=CC=CC=2)C2=CSC=C2)=C1 CKYLUTWAKNOUEY-FQEVSTJZSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- UNAILACUVRPXJI-UHFFFAOYSA-N 2-[4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-6-phenyl-3,4-dihydro-1h-pyrimidin-5-yl]benzonitrile Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C(=CC=CC=2)C#N)=C1 UNAILACUVRPXJI-UHFFFAOYSA-N 0.000 claims 1
- YRGSUCYPTVRYJT-UHFFFAOYSA-N 2-chloro-6-hydroxy-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=C(O)C=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 YRGSUCYPTVRYJT-UHFFFAOYSA-N 0.000 claims 1
- GLAKVSSGNZVRJS-UHFFFAOYSA-N 2-ethoxy-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GLAKVSSGNZVRJS-UHFFFAOYSA-N 0.000 claims 1
- QULVCPYPVCJDOS-UHFFFAOYSA-N 2-ethoxy-4-[2-(methylamino)-5,6-diphenyl-1,4-dihydropyrimidin-4-yl]-6-nitrophenol Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(/N2)=N\C)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QULVCPYPVCJDOS-UHFFFAOYSA-N 0.000 claims 1
- JVGGKERFRZDUNO-UHFFFAOYSA-N 2-ethoxy-6-hydroxy-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound OC1=C(C(O)=O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JVGGKERFRZDUNO-UHFFFAOYSA-N 0.000 claims 1
- DQMQJXWTTDXFGD-UHFFFAOYSA-N 2-ethoxy-6-nitro-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound [O-][N+](=O)C1=C(C(O)=O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DQMQJXWTTDXFGD-UHFFFAOYSA-N 0.000 claims 1
- RDTDBQOESGKXLX-UHFFFAOYSA-N 2-fluoro-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 RDTDBQOESGKXLX-UHFFFAOYSA-N 0.000 claims 1
- YGUFBVGTCSVOPX-UHFFFAOYSA-N 2-fluoro-6-hydroxy-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C(F)C(C(=O)O)=C(O)C=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 YGUFBVGTCSVOPX-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- OHXJYTLTJXOSGB-UHFFFAOYSA-N 2-hydroxy-3-nitro-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzonitrile Chemical compound C1=C([N+]([O-])=O)C(O)=C(C#N)C=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 OHXJYTLTJXOSGB-UHFFFAOYSA-N 0.000 claims 1
- SODASIPXVDIVMN-UHFFFAOYSA-N 2-hydroxy-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 SODASIPXVDIVMN-UHFFFAOYSA-N 0.000 claims 1
- LJGIEQCHNBEDQK-UHFFFAOYSA-N 2-hydroxy-4-(2-oxo-5-phenyl-6-pyridin-3-yl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=NC=CC=2)NC(=O)N1 LJGIEQCHNBEDQK-UHFFFAOYSA-N 0.000 claims 1
- FEQGUTDKPWMUBH-INIZCTEOSA-N 2-hydroxy-4-[(4s)-6-(1-methylpyrazol-4-yl)-2-oxo-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=C(C2=CSC=C2)[C@H](C=2C=C(O)C(C(O)=O)=CC=2)NC(=O)N1 FEQGUTDKPWMUBH-INIZCTEOSA-N 0.000 claims 1
- XGQDFSGMLZLAQZ-UHFFFAOYSA-N 2-hydroxy-4-[6-(1-methylpyrazol-4-yl)-2-oxo-5-phenyl-3,4-dihydro-1h-pyrimidin-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=C(C=2C=CC=CC=2)C(C=2C=C(O)C(C(O)=O)=CC=2)NC(=O)N1 XGQDFSGMLZLAQZ-UHFFFAOYSA-N 0.000 claims 1
- BHJLZKUAMFJFKY-UHFFFAOYSA-N 2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 BHJLZKUAMFJFKY-UHFFFAOYSA-N 0.000 claims 1
- OHZHNFJQLIKACZ-UHFFFAOYSA-N 2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 OHZHNFJQLIKACZ-UHFFFAOYSA-N 0.000 claims 1
- HDLLNMUTNSWJKK-UHFFFAOYSA-N 2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzonitrile Chemical compound C1=C(C#N)C(O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 HDLLNMUTNSWJKK-UHFFFAOYSA-N 0.000 claims 1
- VGRYOIHYIGGOKZ-UHFFFAOYSA-N 2-hydroxy-6-methoxy-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound OC1=C(C(O)=O)C(OC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 VGRYOIHYIGGOKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- KDAPTJGFAZTMIA-UHFFFAOYSA-N 2-nitro-4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 KDAPTJGFAZTMIA-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- ZWTWFSARKULCHJ-UHFFFAOYSA-N 3-[4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-5-phenyl-3,4-dihydro-1h-pyrimidin-6-yl]benzonitrile Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(C=CC=2)C#N)C=2C=CC=CC=2)=C1 ZWTWFSARKULCHJ-UHFFFAOYSA-N 0.000 claims 1
- FFUXGBFHKSSFTL-UHFFFAOYSA-N 3-[4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-6-phenyl-3,4-dihydro-1h-pyrimidin-5-yl]benzonitrile Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(C=CC=2)C#N)=C1 FFUXGBFHKSSFTL-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- BXDDPPIGMTUWQI-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzamide Chemical compound NC(=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BXDDPPIGMTUWQI-UHFFFAOYSA-N 0.000 claims 1
- CRGFPJUSFSACHE-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound OC(=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 CRGFPJUSFSACHE-UHFFFAOYSA-N 0.000 claims 1
- NBBJJCDXXKTGDU-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzonitrile Chemical compound N#CC1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NBBJJCDXXKTGDU-UHFFFAOYSA-N 0.000 claims 1
- LCQKPHPMNIMILY-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-(2-oxo-6-phenyl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-4-yl)benzonitrile Chemical compound N#CC1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C2=CSC=C2)=C1 LCQKPHPMNIMILY-UHFFFAOYSA-N 0.000 claims 1
- RPBCIEUBMRQRMA-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-(2-oxo-6-pyridin-3-yl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound OC(=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=NC=CC=2)C2=CSC=C2)=C1 RPBCIEUBMRQRMA-UHFFFAOYSA-N 0.000 claims 1
- WWDBLNJVAXEVJG-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-(2-oxo-6-pyridin-3-yl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-4-yl)benzonitrile Chemical compound N#CC1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=NC=CC=2)C2=CSC=C2)=C1 WWDBLNJVAXEVJG-UHFFFAOYSA-N 0.000 claims 1
- RPBCIEUBMRQRMA-IBGZPJMESA-N 3-ethoxy-2-hydroxy-5-[(4s)-2-oxo-6-pyridin-3-yl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-4-yl]benzoic acid Chemical compound OC(=O)C1=C(O)C(OCC)=CC([C@H]2C(=C(NC(=O)N2)C=2C=NC=CC=2)C2=CSC=C2)=C1 RPBCIEUBMRQRMA-IBGZPJMESA-N 0.000 claims 1
- WWWZLPDDCZIDGJ-KRWDZBQOSA-N 3-ethoxy-2-hydroxy-5-[(4s)-6-(1-methylpyrazol-4-yl)-2-oxo-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-4-yl]benzoic acid Chemical compound OC(=O)C1=C(O)C(OCC)=CC([C@H]2C(=C(C3=CN(C)N=C3)NC(=O)N2)C2=CSC=C2)=C1 WWWZLPDDCZIDGJ-KRWDZBQOSA-N 0.000 claims 1
- PCXRAXPZYKTVMJ-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-[5-(3-methoxyphenyl)-2-oxo-6-pyridin-3-yl-3,4-dihydro-1h-pyrimidin-4-yl]benzoic acid Chemical compound OC(=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=NC=CC=2)C=2C=C(OC)C=CC=2)=C1 PCXRAXPZYKTVMJ-UHFFFAOYSA-N 0.000 claims 1
- WWWZLPDDCZIDGJ-UHFFFAOYSA-N 3-ethoxy-2-hydroxy-5-[6-(1-methylpyrazol-4-yl)-2-oxo-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-4-yl]benzoic acid Chemical compound OC(=O)C1=C(O)C(OCC)=CC(C2C(=C(C3=CN(C)N=C3)NC(=O)N2)C2=CSC=C2)=C1 WWWZLPDDCZIDGJ-UHFFFAOYSA-N 0.000 claims 1
- WFCYBGKFAJGXTF-UHFFFAOYSA-N 3-fluoro-2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound FC1=C(O)C(C(=O)O)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 WFCYBGKFAJGXTF-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- IMNKYNRSKQYEHI-UHFFFAOYSA-N 4-(2-amino-5,6-diphenyl-1,4-dihydropyrimidin-4-yl)-2-ethoxy-6-nitrophenol Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=N)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 IMNKYNRSKQYEHI-UHFFFAOYSA-N 0.000 claims 1
- GZETZCUPPWOTPK-UHFFFAOYSA-N 4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)-2-(trifluoromethyl)benzoic acid Chemical compound C1=C(C(F)(F)F)C(C(=O)O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 GZETZCUPPWOTPK-UHFFFAOYSA-N 0.000 claims 1
- KTPAJIOUJCTILD-UHFFFAOYSA-N 4-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 KTPAJIOUJCTILD-UHFFFAOYSA-N 0.000 claims 1
- CVGCBASBATWEBQ-UHFFFAOYSA-N 4-(3,4-dihydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 CVGCBASBATWEBQ-UHFFFAOYSA-N 0.000 claims 1
- JNFQASIEUHQHCL-UHFFFAOYSA-N 4-(3-bromo-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound BrC1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JNFQASIEUHQHCL-UHFFFAOYSA-N 0.000 claims 1
- RHIPXEUPEZJABW-UHFFFAOYSA-N 4-(3-chloro-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound C1=C([N+]([O-])=O)C(O)=C(Cl)C=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 RHIPXEUPEZJABW-UHFFFAOYSA-N 0.000 claims 1
- XPNGYVLFWPGZFS-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-methylsulfinylphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound CS(=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 XPNGYVLFWPGZFS-UHFFFAOYSA-N 0.000 claims 1
- MEVOEGXCFUTSAY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-methylsulfonylphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound CS(=O)(=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MEVOEGXCFUTSAY-UHFFFAOYSA-N 0.000 claims 1
- ZNCUJLHGVJXMSY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-1,3-dimethyl-5,6-diphenyl-4h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(N(C)C(=O)N2C)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 ZNCUJLHGVJXMSY-UHFFFAOYSA-N 0.000 claims 1
- SKQWINVTPRSQQT-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-3-methyl-5,6-diphenyl-1,4-dihydropyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2C)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SKQWINVTPRSQQT-UHFFFAOYSA-N 0.000 claims 1
- LBMFXSVJMHVNBN-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LBMFXSVJMHVNBN-UHFFFAOYSA-N 0.000 claims 1
- CPJQPKVDXPNPAE-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidine-2-thione Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=S)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 CPJQPKVDXPNPAE-UHFFFAOYSA-N 0.000 claims 1
- DDNXQDYEJUSHAV-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(2-fluorophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C(=CC=CC=2)F)=C1 DDNXQDYEJUSHAV-UHFFFAOYSA-N 0.000 claims 1
- NGXCZXHVFWVACY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(2-methylphenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C(=CC=CC=2)C)=C1 NGXCZXHVFWVACY-UHFFFAOYSA-N 0.000 claims 1
- DBCFFASQPNPIKW-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(3-ethylphenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(CC)C=CC=2)=C1 DBCFFASQPNPIKW-UHFFFAOYSA-N 0.000 claims 1
- PIEAAOPVFLCUSE-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(3-fluorophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(F)C=CC=2)=C1 PIEAAOPVFLCUSE-UHFFFAOYSA-N 0.000 claims 1
- KCGSZISUSVFBPQ-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(3-methoxyphenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(OC)C=CC=2)=C1 KCGSZISUSVFBPQ-UHFFFAOYSA-N 0.000 claims 1
- MNYYFLRLTXWGTB-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(3-methoxyphenyl)-6-pyridin-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=NC=CC=2)C=2C=C(OC)C=CC=2)=C1 MNYYFLRLTXWGTB-UHFFFAOYSA-N 0.000 claims 1
- PLQPSZNYOMHDEU-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(3-methylphenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 PLQPSZNYOMHDEU-UHFFFAOYSA-N 0.000 claims 1
- URIWEFJXBFBKNB-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(4-methoxyphenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC(OC)=CC=2)=C1 URIWEFJXBFBKNB-UHFFFAOYSA-N 0.000 claims 1
- UJCFGXRABIEBQG-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-(4-methylphenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC(C)=CC=2)=C1 UJCFGXRABIEBQG-UHFFFAOYSA-N 0.000 claims 1
- OZDLUGFFZWXIHU-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(1h-pyrrol-3-yl)-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3=CNC=C3)NC(=O)N2)C=2C=CC=CC=2)=C1 OZDLUGFFZWXIHU-UHFFFAOYSA-N 0.000 claims 1
- QRKRWADUAMVJKN-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(4-phenylphenyl)-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QRKRWADUAMVJKN-UHFFFAOYSA-N 0.000 claims 1
- CVNKUHFGMRWKAD-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(=CC=2)C(F)(F)F)C=2C=CC=CC=2)=C1 CVNKUHFGMRWKAD-UHFFFAOYSA-N 0.000 claims 1
- HNVJYUPEBXXFJM-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-pyridin-2-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2N=CC=CC=2)C=2C=CC=CC=2)=C1 HNVJYUPEBXXFJM-UHFFFAOYSA-N 0.000 claims 1
- IIDWQHVTAQYFRQ-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-pyridin-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=NC=CC=2)C=2C=CC=CC=2)=C1 IIDWQHVTAQYFRQ-UHFFFAOYSA-N 0.000 claims 1
- SYYVYMXUNMEKPW-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-pyridin-4-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CN=CC=2)C=2C=CC=CC=2)=C1 SYYVYMXUNMEKPW-UHFFFAOYSA-N 0.000 claims 1
- BNCSWXXJQORABF-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-quinolin-6-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C3C=CC=NC3=CC=2)C=2C=CC=CC=2)=C1 BNCSWXXJQORABF-UHFFFAOYSA-N 0.000 claims 1
- JKDAQGSILSLNGR-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-thiophen-2-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C=3SC=CC=3)NC(=O)N2)C=2C=CC=CC=2)=C1 JKDAQGSILSLNGR-UHFFFAOYSA-N 0.000 claims 1
- UOCKFKMTSUMOIS-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3=CSC=C3)NC(=O)N2)C=2C=CC=CC=2)=C1 UOCKFKMTSUMOIS-UHFFFAOYSA-N 0.000 claims 1
- OYVZKNYVPWDTKK-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(1-methylimidazol-4-yl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C=3N=CN(C)C=3)NC(=O)N2)C=2C=CC=CC=2)=C1 OYVZKNYVPWDTKK-UHFFFAOYSA-N 0.000 claims 1
- DONZBYIZBMQWPQ-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(1-methylpyrazol-3-yl)-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3=NN(C)C=C3)NC(=O)N2)C2=CSC=C2)=C1 DONZBYIZBMQWPQ-UHFFFAOYSA-N 0.000 claims 1
- AMAUOCUJWIIANA-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(1-methylpyrazol-4-yl)-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3=CN(C)N=C3)NC(=O)N2)C2=CSC=C2)=C1 AMAUOCUJWIIANA-UHFFFAOYSA-N 0.000 claims 1
- PNDTXXPDVJUPPD-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(2-fluorophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C(=CC=CC=2)F)C=2C=CC=CC=2)=C1 PNDTXXPDVJUPPD-UHFFFAOYSA-N 0.000 claims 1
- FHWRDZIZURLLBE-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(2-methylphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C(=CC=CC=2)C)C=2C=CC=CC=2)=C1 FHWRDZIZURLLBE-UHFFFAOYSA-N 0.000 claims 1
- SBLRYPJYLFHSFD-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(2-methylpyrazol-3-yl)-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C=3N(N=CC=3)C)NC(=O)N2)C2=CSC=C2)=C1 SBLRYPJYLFHSFD-UHFFFAOYSA-N 0.000 claims 1
- HUHSQZVMBPNHOO-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(3-fluoro-4-methoxyphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(F)C(OC)=CC=2)C=2C=CC=CC=2)=C1 HUHSQZVMBPNHOO-UHFFFAOYSA-N 0.000 claims 1
- MZLWSIOQOYFMIP-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(3-fluorophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(F)C=CC=2)C=2C=CC=CC=2)=C1 MZLWSIOQOYFMIP-UHFFFAOYSA-N 0.000 claims 1
- WUKYYXXMFJKTPS-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(3-hydroxyphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(O)C=CC=2)C=2C=CC=CC=2)=C1 WUKYYXXMFJKTPS-UHFFFAOYSA-N 0.000 claims 1
- WGDKFHABJACHTO-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(3-methoxyphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(OC)C=CC=2)C=2C=CC=CC=2)=C1 WGDKFHABJACHTO-UHFFFAOYSA-N 0.000 claims 1
- JYMBPSLBSLCQJV-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-fluorophenyl)-5-(3-methoxyphenyl)-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(F)=CC=2)C=2C=C(OC)C=CC=2)=C1 JYMBPSLBSLCQJV-UHFFFAOYSA-N 0.000 claims 1
- YIOZKEDYRJIXLE-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-fluorophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(F)=CC=2)C=2C=CC=CC=2)=C1 YIOZKEDYRJIXLE-UHFFFAOYSA-N 0.000 claims 1
- WYDGNSXVKZTXOY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-fluorophenyl)-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(F)=CC=2)C2=CSC=C2)=C1 WYDGNSXVKZTXOY-UHFFFAOYSA-N 0.000 claims 1
- UDLHYTQUXNYTEV-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-hydroxyphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(O)=CC=2)C=2C=CC=CC=2)=C1 UDLHYTQUXNYTEV-UHFFFAOYSA-N 0.000 claims 1
- BGAMKKUFJRMCRH-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(OC)=CC=2)C=2C=CC=CC=2)=C1 BGAMKKUFJRMCRH-UHFFFAOYSA-N 0.000 claims 1
- HDIUSHKUHXYOSY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-methylphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(C)=CC=2)C=2C=CC=CC=2)=C1 HDIUSHKUHXYOSY-UHFFFAOYSA-N 0.000 claims 1
- RPLQAQYDNDOROV-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-morpholin-4-ylphenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(=CC=2)N2CCOCC2)C=2C=CC=CC=2)=C1 RPLQAQYDNDOROV-UHFFFAOYSA-N 0.000 claims 1
- VUVIXYZLLDATJH-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(furan-2-yl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C=3OC=CC=3)NC(=O)N2)C=2C=CC=CC=2)=C1 VUVIXYZLLDATJH-UHFFFAOYSA-N 0.000 claims 1
- QNVLEFUVFCTHRY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(furan-3-yl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3=COC=C3)NC(=O)N2)C=2C=CC=CC=2)=C1 QNVLEFUVFCTHRY-UHFFFAOYSA-N 0.000 claims 1
- CKYUFFDRFRFNSD-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(oxolan-2-yl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3OCCC3)NC(=O)N2)C=2C=CC=CC=2)=C1 CKYUFFDRFRFNSD-UHFFFAOYSA-N 0.000 claims 1
- VGRFQUBADZVKSA-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(oxolan-3-yl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3COCC3)NC(=O)N2)C=2C=CC=CC=2)=C1 VGRFQUBADZVKSA-UHFFFAOYSA-N 0.000 claims 1
- CKYUFFDRFRFNSD-VTBWFHPJSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-[(2r)-oxolan-2-yl]-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C([C@@H]3OCCC3)NC(=O)N2)C=2C=CC=CC=2)=C1 CKYUFFDRFRFNSD-VTBWFHPJSA-N 0.000 claims 1
- CKYUFFDRFRFNSD-UCFFOFKASA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-[(2s)-oxolan-2-yl]-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C([C@H]3OCCC3)NC(=O)N2)C=2C=CC=CC=2)=C1 CKYUFFDRFRFNSD-UCFFOFKASA-N 0.000 claims 1
- PPLXRRSNEJKLSG-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-isoquinolin-6-yl-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C3C=CN=CC3=CC=2)C=2C=CC=CC=2)=C1 PPLXRRSNEJKLSG-UHFFFAOYSA-N 0.000 claims 1
- UYHWTFKSRCHPES-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-naphthalen-1-yl-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C3=CC=CC=C3C=CC=2)C=2C=CC=CC=2)=C1 UYHWTFKSRCHPES-UHFFFAOYSA-N 0.000 claims 1
- XRWOUBIVEXYPLS-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-naphthalen-2-yl-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC=CC=2)=C1 XRWOUBIVEXYPLS-UHFFFAOYSA-N 0.000 claims 1
- HWKCIKOTQZUZMC-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-(1,3-thiazol-2-yl)-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2SC=CN=2)=C1 HWKCIKOTQZUZMC-UHFFFAOYSA-N 0.000 claims 1
- UJVCDDWRJSIAFS-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-(3-phenylphenyl)-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 UJVCDDWRJSIAFS-UHFFFAOYSA-N 0.000 claims 1
- ZKLITGSURLNKET-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-(4-phenylphenyl)-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 ZKLITGSURLNKET-UHFFFAOYSA-N 0.000 claims 1
- XQOODDLZQCTOSY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-pyrazin-2-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2N=CC=NC=2)=C1 XQOODDLZQCTOSY-UHFFFAOYSA-N 0.000 claims 1
- FUJJURAATWKWFH-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-pyridin-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=NC=CC=2)=C1 FUJJURAATWKWFH-UHFFFAOYSA-N 0.000 claims 1
- MZQSSLOXBLNJPE-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-pyridin-4-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CN=CC=2)=C1 MZQSSLOXBLNJPE-UHFFFAOYSA-N 0.000 claims 1
- SMPUUNISELUJKG-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-thiophen-2-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2SC=CC=2)=C1 SMPUUNISELUJKG-UHFFFAOYSA-N 0.000 claims 1
- CKYLUTWAKNOUEY-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C2=CSC=C2)=C1 CKYLUTWAKNOUEY-UHFFFAOYSA-N 0.000 claims 1
- DNBYCAYCOVLSSS-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-pyrazin-2-yl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2N=CC=NC=2)C2=CSC=C2)=C1 DNBYCAYCOVLSSS-UHFFFAOYSA-N 0.000 claims 1
- OOLWDJTWVWHETJ-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-pyridin-3-yl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=NC=CC=2)C2=CSC=C2)=C1 OOLWDJTWVWHETJ-UHFFFAOYSA-N 0.000 claims 1
- QWWXQAVPZCMLRN-UHFFFAOYSA-N 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-pyridin-4-yl-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CN=CC=2)C2=CSC=C2)=C1 QWWXQAVPZCMLRN-UHFFFAOYSA-N 0.000 claims 1
- GZSIAFDAQJPMDR-UHFFFAOYSA-N 4-(3-ethoxy-5-fluoro-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound FC1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GZSIAFDAQJPMDR-UHFFFAOYSA-N 0.000 claims 1
- VMUUIPUQSWPCIB-UHFFFAOYSA-N 4-(3-fluoro-4-hydroxy-5-methoxyphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound FC1=C(O)C(OC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 VMUUIPUQSWPCIB-UHFFFAOYSA-N 0.000 claims 1
- KIDJBTTUMYHFFB-UHFFFAOYSA-N 4-(3-fluoro-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound C1=C([N+]([O-])=O)C(O)=C(F)C=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 KIDJBTTUMYHFFB-UHFFFAOYSA-N 0.000 claims 1
- BJDFBWOOHQSOFW-UHFFFAOYSA-N 4-(4-hydroxy-3-methoxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BJDFBWOOHQSOFW-UHFFFAOYSA-N 0.000 claims 1
- GTRJAAOTGVGBGJ-UHFFFAOYSA-N 4-(4-hydroxy-3-methoxyphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound C1=C(O)C(OC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GTRJAAOTGVGBGJ-UHFFFAOYSA-N 0.000 claims 1
- BWWPCCXCTMYJAC-UHFFFAOYSA-N 4-(4-hydroxy-3-nitro-5-propan-2-yloxyphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OC(C)C)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BWWPCCXCTMYJAC-UHFFFAOYSA-N 0.000 claims 1
- JLAVWNZEUWFJRP-UHFFFAOYSA-N 4-(4-hydroxy-3-nitro-5-propoxyphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JLAVWNZEUWFJRP-UHFFFAOYSA-N 0.000 claims 1
- NVSNLDXGBNBHQP-UHFFFAOYSA-N 4-(4-hydroxy-3-nitro-5-propylphenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(CCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NVSNLDXGBNBHQP-UHFFFAOYSA-N 0.000 claims 1
- CVMPVCHAOIZFLQ-UHFFFAOYSA-N 4-(4-hydroxy-3-nitrophenyl)-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 CVMPVCHAOIZFLQ-UHFFFAOYSA-N 0.000 claims 1
- CCOYXHVCUIYRQZ-UHFFFAOYSA-N 4-[3-[2-(dimethylamino)ethoxy]-4-hydroxy-5-nitrophenyl]-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCCN(C)C)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 CCOYXHVCUIYRQZ-UHFFFAOYSA-N 0.000 claims 1
- ZXZOSPPAYBCTEQ-UHFFFAOYSA-N 4-[4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-5-phenyl-3,4-dihydro-1h-pyrimidin-6-yl]benzonitrile Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(=CC=2)C#N)C=2C=CC=CC=2)=C1 ZXZOSPPAYBCTEQ-UHFFFAOYSA-N 0.000 claims 1
- MKQLTVSYAWMKIO-UHFFFAOYSA-N 4-[4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-6-phenyl-3,4-dihydro-1h-pyrimidin-5-yl]benzonitrile Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C#N)=C1 MKQLTVSYAWMKIO-UHFFFAOYSA-N 0.000 claims 1
- DNGFDGUWTUIIRU-UHFFFAOYSA-N 4-[4-hydroxy-3-(2-hydroxyethoxy)-5-nitrophenyl]-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCCO)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DNGFDGUWTUIIRU-UHFFFAOYSA-N 0.000 claims 1
- HQVRQTGMBSAKJA-UHFFFAOYSA-N 4-[4-hydroxy-3-(2-methoxyethoxy)-5-nitrophenyl]-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCCOC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HQVRQTGMBSAKJA-UHFFFAOYSA-N 0.000 claims 1
- YYPAVOLBBFMCAE-UHFFFAOYSA-N 4-[4-hydroxy-3-nitro-5-(trifluoromethyl)phenyl]-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound C1=C(C(F)(F)F)C(O)=C([N+]([O-])=O)C=C1C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NC(=O)N1 YYPAVOLBBFMCAE-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- BGCSYKUVFLQDEG-UHFFFAOYSA-N 5,6-diphenyl-4-[4-(2h-tetrazol-5-yl)phenyl]-3,4-dihydro-1h-pyrimidin-2-one Chemical compound N1C(=O)NC(C=2C=CC(=CC=2)C2=NNN=N2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BGCSYKUVFLQDEG-UHFFFAOYSA-N 0.000 claims 1
- VAXYFWJXYNVTPQ-UHFFFAOYSA-N 5-(2-chlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)=C1 VAXYFWJXYNVTPQ-UHFFFAOYSA-N 0.000 claims 1
- GUFDJFBFWRYDGH-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)=C1 GUFDJFBFWRYDGH-UHFFFAOYSA-N 0.000 claims 1
- RMEYEQFAYKGIBA-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(F)C(F)=CC=2)=C1 RMEYEQFAYKGIBA-UHFFFAOYSA-N 0.000 claims 1
- SZRBOIRUDMRZNO-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(OC)C(OC)=CC=2)=C1 SZRBOIRUDMRZNO-UHFFFAOYSA-N 0.000 claims 1
- JDWIVWPYBUKUAO-UHFFFAOYSA-N 5-(3-chlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=C(Cl)C=CC=2)=C1 JDWIVWPYBUKUAO-UHFFFAOYSA-N 0.000 claims 1
- SRPKLZWJUVLLQU-UHFFFAOYSA-N 5-(4-bromophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC(Br)=CC=2)=C1 SRPKLZWJUVLLQU-UHFFFAOYSA-N 0.000 claims 1
- FNBPOFRGBHNSCL-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 FNBPOFRGBHNSCL-UHFFFAOYSA-N 0.000 claims 1
- NTUUSMYMEAQJJY-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C)C)=C1 NTUUSMYMEAQJJY-UHFFFAOYSA-N 0.000 claims 1
- ZEEAXYVKGQZERN-UHFFFAOYSA-N 5-cyclohexyl-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C2CCCCC2)=C1 ZEEAXYVKGQZERN-UHFFFAOYSA-N 0.000 claims 1
- JFNNQYBYEMVMRY-UHFFFAOYSA-N 5-phenyl-6-pyridin-3-yl-4-[4-(2h-tetrazol-5-yl)phenyl]-3,4-dihydro-1h-pyrimidin-2-one Chemical compound N1C(=O)NC(C=2C=CC(=CC=2)C2=NNN=N2)C(C=2C=CC=CC=2)=C1C1=CC=CN=C1 JFNNQYBYEMVMRY-UHFFFAOYSA-N 0.000 claims 1
- UFAFTOIUMYYYKZ-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C3OCOC3=CC=2)C=2C=CC=CC=2)=C1 UFAFTOIUMYYYKZ-UHFFFAOYSA-N 0.000 claims 1
- HCEMBIIHGFQSKR-UHFFFAOYSA-N 6-(2,4-difluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C(=CC(F)=CC=2)F)C=2C=CC=CC=2)=C1 HCEMBIIHGFQSKR-UHFFFAOYSA-N 0.000 claims 1
- UVINVQDVOQVSKF-UHFFFAOYSA-N 6-(2-chlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C(=CC=CC=2)Cl)C=2C=CC=CC=2)=C1 UVINVQDVOQVSKF-UHFFFAOYSA-N 0.000 claims 1
- ZWQHGPPRMFAGGS-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(Cl)C(Cl)=CC=2)C=2C=CC=CC=2)=C1 ZWQHGPPRMFAGGS-UHFFFAOYSA-N 0.000 claims 1
- VJZJZKYUPAWTIH-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(F)C(F)=CC=2)C=2C=CC=CC=2)=C1 VJZJZKYUPAWTIH-UHFFFAOYSA-N 0.000 claims 1
- FSEJYIZGBFPMNS-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(OC)C(OC)=CC=2)C=2C=CC=CC=2)=C1 FSEJYIZGBFPMNS-UHFFFAOYSA-N 0.000 claims 1
- UYCZPDJRPDOSKW-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(Cl)C=C(Cl)C=2)C=2C=CC=CC=2)=C1 UYCZPDJRPDOSKW-UHFFFAOYSA-N 0.000 claims 1
- KITXYOMQXUQYSA-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(F)C=C(F)C=2)C=2C=CC=CC=2)=C1 KITXYOMQXUQYSA-UHFFFAOYSA-N 0.000 claims 1
- OCLXPVPYOPGHIF-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(Cl)C(F)=CC=2)C=2C=CC=CC=2)=C1 OCLXPVPYOPGHIF-UHFFFAOYSA-N 0.000 claims 1
- YQSCMNHPJXFQFM-UHFFFAOYSA-N 6-(3-chloro-5-fluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(Cl)C=C(F)C=2)C=2C=CC=CC=2)=C1 YQSCMNHPJXFQFM-UHFFFAOYSA-N 0.000 claims 1
- SSAQPZWTUYQCKM-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(Cl)C=CC=2)C=2C=CC=CC=2)=C1 SSAQPZWTUYQCKM-UHFFFAOYSA-N 0.000 claims 1
- RZTFSHOYQXMJSG-UHFFFAOYSA-N 6-(3-ethoxy-4-hydroxy-5-nitrophenyl)-3-methyl-4,5-diphenyl-1,6-dihydropyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(N(C)C(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 RZTFSHOYQXMJSG-UHFFFAOYSA-N 0.000 claims 1
- FZAUSYBZZHAHGL-UHFFFAOYSA-N 6-(4-aminophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(N)=CC=2)C=2C=CC=CC=2)=C1 FZAUSYBZZHAHGL-UHFFFAOYSA-N 0.000 claims 1
- JQNYOAVPHQEKJF-UHFFFAOYSA-N 6-(4-bromophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(Br)=CC=2)C=2C=CC=CC=2)=C1 JQNYOAVPHQEKJF-UHFFFAOYSA-N 0.000 claims 1
- SCCOVQBDEVVKNJ-UHFFFAOYSA-N 6-(4-chloro-3-fluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=C(F)C(Cl)=CC=2)C=2C=CC=CC=2)=C1 SCCOVQBDEVVKNJ-UHFFFAOYSA-N 0.000 claims 1
- VIEZSJLOGURZKV-UHFFFAOYSA-N 6-[1-(benzenesulfonyl)pyrrol-3-yl]-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3=CN(C=C3)S(=O)(=O)C=3C=CC=CC=3)NC(=O)N2)C=2C=CC=CC=2)=C1 VIEZSJLOGURZKV-UHFFFAOYSA-N 0.000 claims 1
- BXJUADYJRFWOPM-UHFFFAOYSA-N 6-[4-(dimethylamino)phenyl]-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(=CC=2)N(C)C)C=2C=CC=CC=2)=C1 BXJUADYJRFWOPM-UHFFFAOYSA-N 0.000 claims 1
- KVAWAFHRBUZPJF-UHFFFAOYSA-N 6-cyclohexyl-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3CCCCC3)NC(=O)N2)C2=CSC=C2)=C1 KVAWAFHRBUZPJF-UHFFFAOYSA-N 0.000 claims 1
- NDBRFODDAONGIK-UHFFFAOYSA-N 6-cyclopentyl-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(C3CCCC3)NC(=O)N2)C=2C=CC=CC=2)=C1 NDBRFODDAONGIK-UHFFFAOYSA-N 0.000 claims 1
- RKVDELKBNAQTPW-UHFFFAOYSA-N 6-pyridin-3-yl-4-[4-(2h-tetrazol-5-yl)phenyl]-5-thiophen-3-yl-3,4-dihydro-1h-pyrimidin-2-one Chemical compound C=1C=CN=CC=1C=1NC(=O)NC(C=2C=CC(=CC=2)C2=NNN=N2)C=1C=1C=CSC=1 RKVDELKBNAQTPW-UHFFFAOYSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- HHQNRQVLECLQKR-UHFFFAOYSA-N CCOC(C=C(C=C1[N+]([O-])=O)N(C=C(CN2)C3=CC=CC=C3)C2=O)=C1O Chemical compound CCOC(C=C(C=C1[N+]([O-])=O)N(C=C(CN2)C3=CC=CC=C3)C2=O)=C1O HHQNRQVLECLQKR-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 241000193163 Clostridioides difficile Species 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000025962 Crush injury Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- 206010067125 Liver injury Diseases 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000029549 Muscle injury Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010021888 Nervous system infections Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 230000036528 appetite Effects 0.000 claims 1
- 235000019789 appetite Nutrition 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 231100000753 hepatic injury Toxicity 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- SECWGMAGKLHBLW-UHFFFAOYSA-N methyl n-[4-[4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-2-oxo-5-phenyl-3,4-dihydro-1h-pyrimidin-6-yl]phenyl]carbamate Chemical compound [O-][N+](=O)C1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC(NC(=O)OC)=CC=2)C=2C=CC=CC=2)=C1 SECWGMAGKLHBLW-UHFFFAOYSA-N 0.000 claims 1
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 claims 1
- FHLHDWVEZSTJQT-UHFFFAOYSA-N n-[2-hydroxy-3-methoxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=C(O)C(OC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 FHLHDWVEZSTJQT-UHFFFAOYSA-N 0.000 claims 1
- GFOOFFCOPJGROJ-UHFFFAOYSA-N n-[3-ethoxy-2-hydroxy-5-(2-oxo-5,6-diphenyl-3,4-dihydro-1h-pyrimidin-4-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=C(O)C(OCC)=CC(C2C(=C(NC(=O)N2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GFOOFFCOPJGROJ-UHFFFAOYSA-N 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 239000002840 nitric oxide donor Substances 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
- 230000004044 response Effects 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 206010040872 skin infection Diseases 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 230000016160 smooth muscle contraction Effects 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 230000000472 traumatic effect Effects 0.000 claims 1
- 201000008827 tuberculosis Diseases 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24585909P | 2009-09-25 | 2009-09-25 | |
| US61/245,859 | 2009-09-25 | ||
| PCT/US2010/050164 WO2011038204A1 (en) | 2009-09-25 | 2010-09-24 | Novel dihydropyrimidin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013505949A JP2013505949A (ja) | 2013-02-21 |
| JP2013505949A5 true JP2013505949A5 (enExample) | 2013-11-07 |
| JP5775519B2 JP5775519B2 (ja) | 2015-09-09 |
Family
ID=43796219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012531061A Expired - Fee Related JP5775519B2 (ja) | 2009-09-25 | 2010-09-24 | Ｓ−ニトロソグルタチオンレダクターゼ阻害薬としての新規ジヒドロピリミジン−２（１ｈ）−オン化合物 |
Country Status (4)
| Country | Link |
|---|---|
| US (3) | US8741915B2 (enExample) |
| EP (1) | EP2480086A4 (enExample) |
| JP (1) | JP5775519B2 (enExample) |
| WO (1) | WO2011038204A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8741915B2 (en) | 2009-09-25 | 2014-06-03 | N30 Pharmaceuticals, Inc. | Dihydropyrimidin-2(1H)-one compounds as S-nitrosoglutathione reductase inhibitors |
| EP2592934B1 (en) | 2010-07-16 | 2015-08-26 | Nivalis Therapeutics, Inc. | Novel dihydropyridin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors and neurokinin-3 receptor antagonists |
| US8906933B2 (en) | 2010-09-24 | 2014-12-09 | N30 Pharmaceuticals, Inc. | Dihydropyrimidin-2(1H)-one compounds as neurokinin-3 receptor antagonists |
| CN104418718B (zh) * | 2013-08-28 | 2018-04-13 | 山东新时代药业有限公司 | 一种环丙基‑2‑溴‑2‑（2‑氟苯基）乙酮的制备方法 |
| WO2016055947A1 (en) * | 2014-10-07 | 2016-04-14 | Glenmark Pharmaceuticals S.A. | Alkyne compounds as s-nitrosoglutathione reductase inhibitors |
| CN104803954B (zh) * | 2015-04-30 | 2018-01-26 | 上海应用技术学院 | 一种福沙那韦中间体的制备方法 |
| WO2018011376A1 (en) * | 2016-07-13 | 2018-01-18 | Centre National De La Recherche Scientifique - Cnrs - | Pyrimidinone derivatives and uses thereof to neutralize the biological activity of chemokines |
| WO2018054711A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
| WO2018054721A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
| WO2018054723A1 (en) | 2016-09-26 | 2018-03-29 | Basf Se | Pyridine compounds for controlling phytopathogenic harmful fungi |
| WO2018065182A1 (en) | 2016-10-04 | 2018-04-12 | Basf Se | Reduced quinoline compounds as antifuni agents |
| WO2018073110A1 (en) | 2016-10-20 | 2018-04-26 | Basf Se | Quinoline compounds as fungicides |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| US6268369B1 (en) | 1994-11-16 | 2001-07-31 | Synaptic Pharmaceutical Corporation | 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines |
| CA2218360A1 (en) | 1995-05-10 | 1996-11-14 | G.D. Searle & Co. | Nitric oxide synthase inhibitors derived from cyclic amidines |
| US6057367A (en) | 1996-08-30 | 2000-05-02 | Duke University | Manipulating nitrosative stress to kill pathologic microbes, pathologic helminths and pathologically proliferating cells or to upregulate nitrosative stress defenses |
| GB9813271D0 (en) | 1998-06-19 | 1998-08-19 | Zeneca Ltd | Composition and use |
| US7049308B2 (en) | 2000-10-26 | 2006-05-23 | Duke University | C-nitroso compounds and use thereof |
| US6359182B1 (en) | 2000-10-26 | 2002-03-19 | Duke University | C-nitroso compounds and use thereof |
| US7179791B2 (en) | 2001-01-11 | 2007-02-20 | Duke University | Inhibiting GS-FDH to modulate NO bioactivity |
| CA2492342C (en) | 2002-07-22 | 2011-03-22 | Orchid Chemicals & Pharmaceuticals Ltd. | Novel bio-active pyrimidine derivatives |
| AU2003255492A1 (en) * | 2002-09-10 | 2004-04-30 | Bayer Healthcare Ag | Heterocyclic derivatives |
| GB0220961D0 (en) * | 2002-09-10 | 2002-10-23 | Bayer Ag | Heterocyclic derivatives |
| US7504382B2 (en) | 2003-05-06 | 2009-03-17 | Cytovia, Inc. | Protease inhibitors for coronaviruses and SARS-CoV and the use thereof |
| WO2005000229A2 (en) | 2003-06-04 | 2005-01-06 | Duke University | Compositions and methods for modulating s-nitrosoglutathione reductase |
| WO2005054239A1 (en) * | 2003-12-05 | 2005-06-16 | Bayer Healthcare Ag | 2-aminopyrimidine derivatives |
| FR2883284A1 (fr) | 2005-03-15 | 2006-09-22 | Commissariat Energie Atomique | Nouveaux derives dihydropyrimidines et leur utilisation comme agents anti-cancereux |
| EP1731911A1 (fr) | 2005-06-07 | 2006-12-13 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Procédé utile pour la détection d'encéphalopathies |
| JP4488963B2 (ja) | 2005-06-23 | 2010-06-23 | 株式会社Adeka | 光学記録材料 |
| WO2007101213A2 (en) * | 2006-02-28 | 2007-09-07 | Kalypsys, Inc. | Novel 2-oxo-1,2,3,4-tetrahydropyrimidines, bicyclic pyrimidine diones and imidazolidine-2,4-diones useful as inducible nitric oxide synthase inhibitors |
| JP5302012B2 (ja) | 2006-03-08 | 2013-10-02 | タケダ カリフォルニア インコーポレイテッド | グルコキナーゼ活性剤 |
| RU2329260C1 (ru) | 2007-02-20 | 2008-07-20 | Юрий Иосифович Копырин | Способ получения 2-анилинопиримидинов или их солей (варианты) |
| ES2395114T3 (es) | 2007-03-27 | 2013-02-08 | Synta Pharmaceuticals Corporation | Derivados de triazinona y de diazinona útiles como inhibidores de Hsp90 |
| WO2009019800A1 (ja) | 2007-08-06 | 2009-02-12 | Nagoya Industrial Science Research Institute | 濾過装置及び濾過方法 |
| WO2009076665A1 (en) * | 2007-12-13 | 2009-06-18 | Indiana University Research And Technology Corporation | Materials and methods for inhibiting mammalian s-nitrosoglutathione reductase |
| AU2008345225A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| US20110201634A1 (en) | 2008-06-13 | 2011-08-18 | Delhi University | Dihydropyridimidinone compounds for the treatment of cardiovascular diseases and process for preparing the same |
| DK2318007T3 (da) * | 2008-08-15 | 2013-03-25 | N30 Pharmaceuticals Inc | Nye pyrrol-inhibitorer af s-nitrosoglutathion-reduktase som terapeutiske midler |
| WO2010046780A2 (en) * | 2008-10-22 | 2010-04-29 | Institut Pasteur Korea | Anti viral compounds |
| WO2010107476A1 (en) | 2009-03-19 | 2010-09-23 | Duke University | Inhibiting gsnor |
| US8741915B2 (en) | 2009-09-25 | 2014-06-03 | N30 Pharmaceuticals, Inc. | Dihydropyrimidin-2(1H)-one compounds as S-nitrosoglutathione reductase inhibitors |
| EP2592934B1 (en) * | 2010-07-16 | 2015-08-26 | Nivalis Therapeutics, Inc. | Novel dihydropyridin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors and neurokinin-3 receptor antagonists |
| US8906933B2 (en) * | 2010-09-24 | 2014-12-09 | N30 Pharmaceuticals, Inc. | Dihydropyrimidin-2(1H)-one compounds as neurokinin-3 receptor antagonists |
-
2010
- 2010-09-24 US US13/496,799 patent/US8741915B2/en not_active Expired - Fee Related
- 2010-09-24 JP JP2012531061A patent/JP5775519B2/ja not_active Expired - Fee Related
- 2010-09-24 EP EP10819517A patent/EP2480086A4/en not_active Withdrawn
- 2010-09-24 WO PCT/US2010/050164 patent/WO2011038204A1/en not_active Ceased
-
2014
- 2014-04-28 US US14/262,915 patent/US9067893B2/en not_active Expired - Fee Related
-
2015
- 2015-04-24 US US14/695,245 patent/US9283229B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013505949A5 (enExample) | ||
| JP6862033B2 (ja) | Ｇｐｒ１２０アゴニストとしてのビアリール誘導体 | |
| RU2454405C2 (ru) | Производные 3-пиридинкарбоксамида и 2-пиразинкарбоксамида в качестве агентов, повышающих уровень лвп-холестерина | |
| EP0733033B1 (en) | Pharmaceutically active substituted aromatic compounds | |
| RU2487713C2 (ru) | Фармацевтическая композиция и способ лечения или профилактики физиологических и/или патофизиологических состояний, ассоциированных с ингибированием киназ pi3k, у млекопитающих | |
| US20080058356A1 (en) | 2,6 Bisheteroaryl-4-Aminopyrimidines as Adenosine Receptor Antagonists | |
| JP2010539187A5 (enExample) | ||
| JP2013542937A5 (enExample) | ||
| JP5494482B2 (ja) | トリアゾール誘導体またはその塩 | |
| CN110642741A (zh) | 作为抗hbv感染的抗病毒剂的官能化苯甲酰胺衍生物 | |
| JP5552539B2 (ja) | Ｃｎｓ障害の処置のためのオキサゾリン誘導体 | |
| JP2010540462A5 (enExample) | ||
| HRP20151201T1 (hr) | Supstituirani derivati benzamida | |
| JP2006509748A5 (enExample) | ||
| JP2007514003A6 (ja) | アデノシン受容体アンタゴニストとしての２，６−ビスヘテロアリール−４−アミノピリミジン | |
| US20160024004A1 (en) | Novel antiviral agents against hbv infection | |
| WO2009107391A1 (ja) | ６員芳香環含有化合物 | |
| RU2008136553A (ru) | Производные бензотиазола в качестве агонистов бета2 адренорецептора | |
| JP2005523901A (ja) | Ｎｐｙアンタゴニストとしてのキノリン誘導体 | |
| JP2006503081A5 (enExample) | ||
| JP2013519724A5 (enExample) | ||
| HRP20160359T1 (hr) | Derivati kinazolindiona, njihovo dobivanje i njihove terapijske primjene | |
| JP2008516902A5 (enExample) | ||
| JP2020526547A5 (enExample) | ||
| JP2017529346A5 (enExample) |