JP2018535999A5 - - Google Patents
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- JP2018535999A5 JP2018535999A5 JP2018528638A JP2018528638A JP2018535999A5 JP 2018535999 A5 JP2018535999 A5 JP 2018535999A5 JP 2018528638 A JP2018528638 A JP 2018528638A JP 2018528638 A JP2018528638 A JP 2018528638A JP 2018535999 A5 JP2018535999 A5 JP 2018535999A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxy
- dihydropyrimidin
- substituted
- phenyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 62
- -1 substituted Chemical class 0.000 claims 44
- 125000000623 heterocyclic group Chemical group 0.000 claims 37
- 229910052731 fluorine Inorganic materials 0.000 claims 32
- 229910052801 chlorine Inorganic materials 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 229910052794 bromium Inorganic materials 0.000 claims 19
- 229910052799 carbon Inorganic materials 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 229910004013 NO 2 Inorganic materials 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 125000004452 carbocyclyl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 6
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 2
- HGJWTRQTKHPHAK-UHFFFAOYSA-N 3-(2,6-dimethoxyphenyl)-6-hydroxy-2-(3-methylbutyl)-5-[[4-(2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound COC1=CC=CC(OC)=C1N1C(CCC(C)C)=NC(O)=C(CC2=CC=C(C=C2)N2C=CC=CC2=O)C1=O HGJWTRQTKHPHAK-UHFFFAOYSA-N 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- ZELONHPQJRCHNY-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)CC1=CC(=C(C=C1)C=1C(=CC(=CC=1)F)C(=O)N)F)=O)C=1SC=C(N=1)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)CC1=CC(=C(C=C1)C=1C(=CC(=CC=1)F)C(=O)N)F)=O)C=1SC=C(N=1)C ZELONHPQJRCHNY-UHFFFAOYSA-N 0.000 claims 2
- VVQBNJDFIRRQCT-VWLOTQADSA-N C(CCC)C=1N(C(=C(C(N=1)=O)CC1=CC=C(C=C1)C1CC1)O)[C@@H](CC)C=1C=C(C#N)C=CC=1 Chemical compound C(CCC)C=1N(C(=C(C(N=1)=O)CC1=CC=C(C=C1)C1CC1)O)[C@@H](CC)C=1C=C(C#N)C=CC=1 VVQBNJDFIRRQCT-VWLOTQADSA-N 0.000 claims 2
- ZHYCOWKZDNDIMS-SANMLTNESA-N CCOCC1=NC(=O)C(CC2=CC=C(C=C2)C2=C(C)C=NC=C2)=C(O)N1[C@@H](COC)C1=CC(F)=CC(F)=C1 Chemical compound CCOCC1=NC(=O)C(CC2=CC=C(C=C2)C2=C(C)C=NC=C2)=C(O)N1[C@@H](COC)C1=CC(F)=CC(F)=C1 ZHYCOWKZDNDIMS-SANMLTNESA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- AHHWJWVMYCUFCN-MHZLTWQESA-N FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)CC1=CC=C(C=C1)C1=C(C(=NC=C1)F)C)=O)C1=NN(C=C1)CC Chemical compound FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)CC1=CC=C(C=C1)C1=C(C(=NC=C1)F)C)=O)C1=NN(C=C1)CC AHHWJWVMYCUFCN-MHZLTWQESA-N 0.000 claims 2
- QGNKMEDPCXKSAA-NDEPHWFRSA-N FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)CC1=CC=C(C=C1)C1=C(C=NC=C1)C)=O)C1=NN(C=C1)CC Chemical compound FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)CC1=CC=C(C=C1)C1=C(C=NC=C1)C)=O)C1=NN(C=C1)CC QGNKMEDPCXKSAA-NDEPHWFRSA-N 0.000 claims 2
- 206010049694 Left Ventricular Dysfunction Diseases 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- 230000002107 myocardial effect Effects 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 238000007634 remodeling Methods 0.000 claims 2
- DEXJWKSVVYKYFQ-UHFFFAOYSA-N 2-(2-cyclopropylethyl)-3-(2,6-dimethoxyphenyl)-5-[[4-(5-fluoro-2-oxopyridin-1-yl)phenyl]methyl]-6-hydroxypyrimidin-4-one Chemical compound COC1=CC=CC(OC)=C1N1C(CCC2CC2)=NC(O)=C(CC2=CC=C(C=C2)N2C=C(F)C=CC2=O)C1=O DEXJWKSVVYKYFQ-UHFFFAOYSA-N 0.000 claims 1
- KYFFPIYRYJBDFZ-UHFFFAOYSA-N 2-(2-cyclopropylethyl)-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound COC1=CC=CC(OC)=C1N1C(CCC2CC2)=NC(O)=C(CC2=CC=C(C=C2)N2C=CC=CC2=O)C1=O KYFFPIYRYJBDFZ-UHFFFAOYSA-N 0.000 claims 1
- BSPYCDJNRMZTTD-UHFFFAOYSA-N 2-(2-cyclopropylethyl)-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(5-methyl-2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C1(CC1)CCC1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1C(C=CC(=C1)C)=O)O BSPYCDJNRMZTTD-UHFFFAOYSA-N 0.000 claims 1
- HGIRVSHGAIOACS-UHFFFAOYSA-N 2-(cyclobutyloxymethyl)-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C1(CCC1)OCC1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1C(C=CC=C1)=O)O HGIRVSHGAIOACS-UHFFFAOYSA-N 0.000 claims 1
- IIUNGCGMTIHKHK-UHFFFAOYSA-N 2-(cyclopropyloxymethyl)-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C1(CC1)OCC1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1C(C=CC=C1)=O)O IIUNGCGMTIHKHK-UHFFFAOYSA-N 0.000 claims 1
- JDMWHPFESDHWQY-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-5-[[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=C(C=C(C=C1)C1=NOC=N1)F)O JDMWHPFESDHWQY-UHFFFAOYSA-N 0.000 claims 1
- TUOQQEKBKGIDFY-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-5-[[3-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC(=C(C=C1)C1=NOC=N1)F)O TUOQQEKBKGIDFY-UHFFFAOYSA-N 0.000 claims 1
- GMOJSPSBHRDCDI-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-5-[[4-(5-fluoro-2-oxopyridin-1-yl)phenyl]methyl]-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1C(C=CC(=C1)F)=O)O GMOJSPSBHRDCDI-UHFFFAOYSA-N 0.000 claims 1
- JBARFQRXBFNRLN-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(4-methoxyphenyl)methyl]pyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CC=C(OC)C=C2)C(=O)N1C1=C(OC)C=CC=C1OC JBARFQRXBFNRLN-UHFFFAOYSA-N 0.000 claims 1
- QPLCKLBAVJVRQD-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(4-methylsulfonylphenyl)methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)S(=O)(=O)C)O QPLCKLBAVJVRQD-UHFFFAOYSA-N 0.000 claims 1
- AOIYMGAIOSGHMP-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(4-morpholin-4-ylphenyl)methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1CCOCC1)O AOIYMGAIOSGHMP-UHFFFAOYSA-N 0.000 claims 1
- HDDLUTRVJPJILA-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(4-phenylphenyl)methyl]pyrimidin-4-one Chemical compound C1(=CC=C(C=C1)CC=1C(N(C(=NC=1O)CCCC)C1=C(C=CC=C1OC)OC)=O)C1=CC=CC=C1 HDDLUTRVJPJILA-UHFFFAOYSA-N 0.000 claims 1
- XNWOGYXBCXSGFL-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(4-pyrazol-1-ylphenyl)methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1N=CC=C1)O XNWOGYXBCXSGFL-UHFFFAOYSA-N 0.000 claims 1
- IFGNEVPLPJPXDF-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(5-methyl-1,2-oxazol-3-yl)methyl]pyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=NOC(C)=C2)C(=O)N1C1=C(OC)C=CC=C1OC IFGNEVPLPJPXDF-UHFFFAOYSA-N 0.000 claims 1
- RUKHJDQBAQIBIN-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[1-(4-methylphenyl)pyrazol-4-yl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC=1C=NN(C=1)C1=CC=C(C=C1)C)O RUKHJDQBAQIBIN-UHFFFAOYSA-N 0.000 claims 1
- GRZBICINDMXGMW-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[2-(4-methylphenyl)-1,3-thiazol-4-yl]methyl]pyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CSC(=N2)C2=CC=C(C)C=C2)C(=O)N1C1=C(OC)C=CC=C1OC GRZBICINDMXGMW-UHFFFAOYSA-N 0.000 claims 1
- BXHRXWNZIIGGGE-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]pyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=NC(=NO2)C2=CC=C(C=C2)C(F)(F)F)C(=O)N1C1=C(OC)C=CC=C1OC BXHRXWNZIIGGGE-UHFFFAOYSA-N 0.000 claims 1
- VRZFZEBAYSGHGV-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(1,2,4-oxadiazol-3-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)C1=NOC=N1)O VRZFZEBAYSGHGV-UHFFFAOYSA-N 0.000 claims 1
- XDXYIEJZZFXBTQ-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(2-methoxypyridin-3-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)C=1C(=NC=CC=1)OC)O XDXYIEJZZFXBTQ-UHFFFAOYSA-N 0.000 claims 1
- XADIDGSFRZTKQS-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(2-oxopiperidin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1C(CCCC1)=O)O XADIDGSFRZTKQS-UHFFFAOYSA-N 0.000 claims 1
- SESDBEINZBEEAO-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1C(C=CC=C1)=O)O SESDBEINZBEEAO-UHFFFAOYSA-N 0.000 claims 1
- IUPFRCINSYZIGR-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]pyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CC=C(C=C2)C2=NC(C)=NO2)C(=O)N1C1=C(OC)C=CC=C1OC IUPFRCINSYZIGR-UHFFFAOYSA-N 0.000 claims 1
- XKLKBHFLDVDRAJ-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(4-methyl-2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CC=C(C=C2)N2C=CC(C)=CC2=O)C(=O)N1C1=C(OC)C=CC=C1OC XKLKBHFLDVDRAJ-UHFFFAOYSA-N 0.000 claims 1
- MBHXUKOKNNDSDR-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(5-methyl-2-oxopyridin-1-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)N1C(C=CC(=C1)C)=O)O MBHXUKOKNNDSDR-UHFFFAOYSA-N 0.000 claims 1
- ALLWKQWMFICPCV-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(6-methylpyridin-3-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)C=1C=NC(=CC=1)C)O ALLWKQWMFICPCV-UHFFFAOYSA-N 0.000 claims 1
- LCFDGEBETWIKBT-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(pyrazol-1-ylmethyl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)CN1N=CC=C1)O LCFDGEBETWIKBT-UHFFFAOYSA-N 0.000 claims 1
- ITXZIJLUVAQUOM-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[4-(thiadiazol-4-yl)phenyl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)C=1N=NSC=1)O ITXZIJLUVAQUOM-UHFFFAOYSA-N 0.000 claims 1
- JHPFVOOHRVMABK-UHFFFAOYSA-N 2-butyl-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[[6-(4-methoxyphenyl)pyridin-3-yl]methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC=1C=NC(=CC=1)C1=CC=C(C=C1)OC)O JHPFVOOHRVMABK-UHFFFAOYSA-N 0.000 claims 1
- JWXROJLBOHUAMT-UHFFFAOYSA-N 2-butyl-5-[[1-(4-chlorophenyl)pyrazol-3-yl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=NN(C=C2)C2=CC=C(Cl)C=C2)C(=O)N1C1=C(OC)C=CC=C1OC JWXROJLBOHUAMT-UHFFFAOYSA-N 0.000 claims 1
- BZGOXDLNTXGOBV-UHFFFAOYSA-N 2-butyl-5-[[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC=1N=C(OC=1)C1=CC=C(C=C1)Cl)O BZGOXDLNTXGOBV-UHFFFAOYSA-N 0.000 claims 1
- UNXNIAOXAOTUJE-UHFFFAOYSA-N 2-butyl-5-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CSC(=N2)C2=CC=C(Cl)C=C2)C(=O)N1C1=C(OC)C=CC=C1OC UNXNIAOXAOTUJE-UHFFFAOYSA-N 0.000 claims 1
- DHPFHDOTELNZHZ-UHFFFAOYSA-N 2-butyl-5-[[2-(4-chlorophenyl)-1,3-thiazol-5-yl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CN=C(S2)C2=CC=C(Cl)C=C2)C(=O)N1C1=C(OC)C=CC=C1OC DHPFHDOTELNZHZ-UHFFFAOYSA-N 0.000 claims 1
- JLGSETLJYWWOLR-UHFFFAOYSA-N 2-butyl-5-[[4-(4-chloro-2-oxopyridin-1-yl)phenyl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CC=C(C=C2)N2C=CC(Cl)=CC2=O)C(=O)N1C1=C(OC)C=CC=C1OC JLGSETLJYWWOLR-UHFFFAOYSA-N 0.000 claims 1
- NXRUBGAYGHJUJW-UHFFFAOYSA-N 2-butyl-5-[[4-(5-chloro-2-oxopyridin-1-yl)phenyl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound CCCCC1=NC(O)=C(CC2=CC=C(C=C2)N2C=C(Cl)C=CC2=O)C(=O)N1C1=C(OC)C=CC=C1OC NXRUBGAYGHJUJW-UHFFFAOYSA-N 0.000 claims 1
- UIBYULIMAQITBQ-UHFFFAOYSA-N 2-butyl-5-[[4-(5-chloropyridin-2-yl)phenyl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC1=CC=C(C=C1)C1=NC=C(C=C1)Cl)O UIBYULIMAQITBQ-UHFFFAOYSA-N 0.000 claims 1
- JCIQKZHZHYVHDC-UHFFFAOYSA-N 2-butyl-5-[[6-(4-chlorophenyl)pyridin-3-yl]methyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)CC=1C=NC(=CC=1)C1=CC=C(C=C1)Cl)O JCIQKZHZHYVHDC-UHFFFAOYSA-N 0.000 claims 1
- MCVTUWWMRVPWNU-UHFFFAOYSA-N 2-butyl-6-hydroxy-3-(2-methoxyphenyl)-5-[(4-methoxyphenyl)methyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1)OC)=O)CC1=CC=C(C=C1)OC)O MCVTUWWMRVPWNU-UHFFFAOYSA-N 0.000 claims 1
- QQOWSFYAETWFMT-UHFFFAOYSA-N 2-cyclopentyl-3-(2,6-dimethoxyphenyl)-5-[[4-(5-fluoro-2-oxopyridin-1-yl)phenyl]methyl]-6-hydroxypyrimidin-4-one Chemical compound COc1cccc(OC)c1-n1c(nc(O)c(Cc2ccc(cc2)-n2cc(F)ccc2=O)c1=O)C1CCCC1 QQOWSFYAETWFMT-UHFFFAOYSA-N 0.000 claims 1
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| WO2012020742A1 (ja) | 2010-08-10 | 2012-02-16 | 塩野義製薬株式会社 | 新規複素環誘導体およびそれらを含有する医薬組成物 |
| US20140005181A1 (en) | 2012-06-21 | 2014-01-02 | Sanford-Burnham Medical Research Institute | Small molecule antagonists of the apelin receptor for the treatment of disease |
| WO2014031928A2 (en) | 2012-08-24 | 2014-02-27 | Philip Jones | Heterocyclic modulators of hif activity for treatment of disease |
| LT2897939T (lt) | 2012-09-21 | 2017-05-10 | Sanofi | Benzimidazolo karboksirūgšties amido dariniai metabolinių arba širdies ir kraujagyslių ligų gydymui |
| HRP20191327T1 (hr) | 2015-06-03 | 2019-11-01 | Bristol Myers Squibb Co | 4-hidroksi-3-(heteroaril)piridin-2-on apj agonisti za primjenju u liječenju kardiovaskularnih poremećaja |
| US10392347B2 (en) | 2015-10-14 | 2019-08-27 | Bristol-Myers Squibb Company | 2,4-dihydroxy-nicotinamides as APJ agonists |
| AR106948A1 (es) | 2015-12-04 | 2018-03-07 | Bristol Myers Squibb Co | Agonistas del receptor de apelina y método de uso |
| EP3390400B1 (en) | 2015-12-16 | 2021-01-20 | Bristol-Myers Squibb Company | Heteroarylhydroxypyrimidinones as agonists of the apj receptor |
| MY189454A (en) | 2016-03-24 | 2022-02-14 | Bristol Myers Squibb Co | 6-hydroxy-4-oxo-1,4-dihydropyrimidine-5-carboxamides as apj agonists |
| WO2017218633A1 (en) | 2016-06-14 | 2017-12-21 | Bristol-Myers Squibb Company | 6-hydroxy-5-(phenyl/heteroarylsulfonyl)pyrimidin-4(1h)-one as apj agonists |
| KR102521955B1 (ko) | 2016-06-14 | 2023-04-13 | 브리스톨-마이어스 스큅 컴퍼니 | Apj 수용체 효능제로서의 4-히드록시-3-술포닐피리딘-2(1h)-온 |
| KR102521956B1 (ko) | 2016-10-14 | 2023-04-14 | 브리스톨-마이어스 스큅 컴퍼니 | 3-술포닐-5-아미노피리딘-2,4-디올 apj 효능제 |
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2016
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- 2016-12-02 PE PE2018001061A patent/PE20181269A1/es unknown
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- 2016-12-02 BR BR112018010720A patent/BR112018010720A8/pt not_active IP Right Cessation
- 2016-12-02 TW TW105140029A patent/TW201722920A/zh unknown
- 2016-12-02 CA CA3007280A patent/CA3007280A1/en not_active Abandoned
- 2016-12-02 WO PCT/US2016/064562 patent/WO2017096130A1/en not_active Ceased
- 2016-12-02 JP JP2018528638A patent/JP6817305B2/ja active Active
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- 2016-12-02 AU AU2016365340A patent/AU2016365340B2/en not_active Expired - Fee Related
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- 2016-12-02 CN CN201680070774.9A patent/CN108473466B/zh active Active
- 2016-12-02 US US15/779,194 patent/US11390616B2/en active Active
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2018
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2022
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