JP2013505949A5 - - Google Patents
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- 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
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- -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
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- 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
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- 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
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- 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
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- 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
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
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- 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
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- 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
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- 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
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Applications Claiming Priority (3)
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| 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)
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| JP2013505949A JP2013505949A (ja) | 2013-02-21 |
| JP2013505949A5 true JP2013505949A5 (https=) | 2013-11-07 |
| JP5775519B2 JP5775519B2 (ja) | 2015-09-09 |
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| JP (1) | JP5775519B2 (https=) |
| WO (1) | WO2011038204A1 (https=) |
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| WO2011038204A1 (en) | 2009-09-25 | 2011-03-31 | N30 Pharmaceuticals, Llc | Novel dihydropyrimidin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors |
| ES2550939T3 (es) | 2010-07-16 | 2015-11-13 | Nivalis Therapeutics, Inc. | Nuevos compuestos de dihidropiridin-2-(1H)-ona como inhibidores de la S-nitrosoglutatión reductasa y antagonistas del receptor de la neurocinina-3 |
| EP2618666A4 (en) * | 2010-09-24 | 2014-04-16 | N30 Pharmaceuticals Inc | NEW DIHYDROPYRIMIDIN-2 (1H) -ON 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 |
| 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 |
| WO2018054711A1 (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 |
| CN121293102A (zh) * | 2025-12-10 | 2026-01-09 | 寿光富康制药有限公司 | 一种高纯度2-溴-6-硝基苯甲醛的合成方法 |
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| 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 |
| KR19990014671A (ko) | 1995-05-10 | 1999-02-25 | 윌리암스로저에이. | 고리형 아미딘으로부터 유도된 산화질소 신타제 저해제 |
| 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 |
| US7317014B2 (en) | 2002-07-22 | 2008-01-08 | Orchid Research Laboratories, Ltd. | Bio-active pyrimidine molecules |
| GB0220961D0 (en) * | 2002-09-10 | 2002-10-23 | Bayer Ag | Heterocyclic derivatives |
| US7566723B2 (en) | 2002-09-10 | 2009-07-28 | Bayer Healthcare Ag | 1-phenyl1-3,4-dihydropyrimidin-2(1H)-one derivatives and their use |
| CA2524882A1 (en) | 2003-05-06 | 2004-11-25 | 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 |
| US8034822B2 (en) | 2006-03-08 | 2011-10-11 | Takeda San Diego, Inc. | Glucokinase activators |
| RU2329260C1 (ru) | 2007-02-20 | 2008-07-20 | Юрий Иосифович Копырин | Способ получения 2-анилинопиримидинов или их солей (варианты) |
| AU2008232354B9 (en) | 2007-03-27 | 2012-07-26 | Synta Pharmaceuticals Corp. | Triazinone and diazinone derivatives useful as Hsp90 inhibitors |
| 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 |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| WO2009150668A1 (en) | 2008-06-13 | 2009-12-17 | 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 |
| WO2011038204A1 (en) | 2009-09-25 | 2011-03-31 | N30 Pharmaceuticals, Llc | Novel dihydropyrimidin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors |
| ES2550939T3 (es) | 2010-07-16 | 2015-11-13 | Nivalis Therapeutics, Inc. | Nuevos compuestos de dihidropiridin-2-(1H)-ona como inhibidores de la S-nitrosoglutatión reductasa y antagonistas del receptor de la neurocinina-3 |
| EP2618666A4 (en) * | 2010-09-24 | 2014-04-16 | N30 Pharmaceuticals Inc | NEW DIHYDROPYRIMIDIN-2 (1H) -ON COMPOUNDS AS NEUROKININ-3 RECEPTOR ANTAGONISTS |
-
2010
- 2010-09-24 WO PCT/US2010/050164 patent/WO2011038204A1/en not_active Ceased
- 2010-09-24 US US13/496,799 patent/US8741915B2/en not_active Expired - Fee Related
- 2010-09-24 EP EP10819517A patent/EP2480086A4/en not_active Withdrawn
- 2010-09-24 JP JP2012531061A patent/JP5775519B2/ja not_active Expired - Fee Related
-
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
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