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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| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| DK3300500T3 (da) | 2015-05-20 | 2020-05-18 | Amgen Inc | Triazolagonister af apj-receptoren |
| WO2016196771A1 (en) | 2015-06-03 | 2016-12-08 | Bristol-Myers Squibb Company | 4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists for use in the treatment of cardiovascular disorders |
| KR102707502B1 (ko) | 2015-10-14 | 2024-09-13 | 브리스톨-마이어스 스큅 컴퍼니 | Apj 효능제로서의 2,4-디히드록시-니코틴아미드 |
| UY37005A (es) | 2015-12-04 | 2017-06-30 | Bristol-Myers Squibb Company Una Corporacion Del Estado De Delaware | Hidroxipirimidinonas sustituidas como agonistas del receptor de apelina y sus usos |
| BR112018012112A2 (pt) | 2015-12-16 | 2018-12-04 | Bristol-Myers Squibb Company | heteroaril-hidroxipirimidinonas como agonistas do receptor apj |
| TWI744301B (zh) | 2016-03-24 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 做為apj促效劑之6-羥基-4-側氧-1,4-二氫嘧啶-5-甲醯胺 |
| WO2017192485A1 (en) | 2016-05-03 | 2017-11-09 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| MX385718B (es) | 2016-06-13 | 2025-03-18 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4). |
| CA3252823A1 (en) | 2016-06-13 | 2025-02-25 | Gilead Sciences, Inc. | Substituted tert-butyl-3-(2-chloro-phenyl)-3-hydroxyazetidine-1-carboxylate compounds |
| KR102384668B1 (ko) * | 2016-06-14 | 2022-04-07 | 브리스톨-마이어스 스큅 컴퍼니 | Apj 효능제로서의 6-히드록시-5-(페닐/헤테로아릴술포닐)피리미딘-4(1h)-온 |
| JP6962941B2 (ja) | 2016-06-14 | 2021-11-05 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | Ａｐｊ受容体アゴニストとしての４−ヒドロキシ−３−スルホニルピリジン−２（１ｈ）−オン |
| JP7037558B2 (ja) | 2016-10-14 | 2022-03-16 | ブリストル－マイヤーズ スクイブ カンパニー | ３－スルホニル－５－アミノピリジン－２，４－ジオール ａｐｊアゴニスト |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| WO2018093576A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| US11020395B2 (en) | 2016-11-16 | 2021-06-01 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the APJ receptor |
| WO2018093579A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| PT3600309T (pt) | 2017-03-28 | 2022-10-03 | Gilead Sciences Inc | Combinações terapêuticas para o tratamento de doenças hepáticas |
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| WO2019169193A1 (en) | 2018-03-01 | 2019-09-06 | Annapurna Bio Inc. | Compounds and compositions for treating conditions associated with apj receptor activity |
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| JPH08325248A (ja) | 1995-05-26 | 1996-12-10 | Chugoku Kayaku Kk | テトラゾール類の新規な合成試薬及びそれを用いたテトラゾール類の製造方法 |
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| ATE286032T1 (de) | 1998-04-23 | 2005-01-15 | Reddys Lab Ltd Dr | Heterozyklische verbindungen,und deren verwendung in arzneimittel,verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen |
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| KR102707502B1 (ko) | 2015-10-14 | 2024-09-13 | 브리스톨-마이어스 스큅 컴퍼니 | Apj 효능제로서의 2,4-디히드록시-니코틴아미드 |
| UY37005A (es) | 2015-12-04 | 2017-06-30 | Bristol-Myers Squibb Company Una Corporacion Del Estado De Delaware | Hidroxipirimidinonas sustituidas como agonistas del receptor de apelina y sus usos |
| BR112018012112A2 (pt) | 2015-12-16 | 2018-12-04 | Bristol-Myers Squibb Company | heteroaril-hidroxipirimidinonas como agonistas do receptor apj |
| TWI744301B (zh) | 2016-03-24 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 做為apj促效劑之6-羥基-4-側氧-1,4-二氫嘧啶-5-甲醯胺 |
| JP6962941B2 (ja) | 2016-06-14 | 2021-11-05 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | Ａｐｊ受容体アゴニストとしての４−ヒドロキシ−３−スルホニルピリジン−２（１ｈ）−オン |
| KR102384668B1 (ko) | 2016-06-14 | 2022-04-07 | 브리스톨-마이어스 스큅 컴퍼니 | Apj 효능제로서의 6-히드록시-5-(페닐/헤테로아릴술포닐)피리미딘-4(1h)-온 |
| JP7037558B2 (ja) | 2016-10-14 | 2022-03-16 | ブリストル－マイヤーズ スクイブ カンパニー | ３－スルホニル－５－アミノピリジン－２，４－ジオール ａｐｊアゴニスト |
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- 2016-12-02 CA CA3007280A patent/CA3007280A1/en not_active Abandoned
- 2016-12-02 JP JP2018528638A patent/JP6817305B2/ja active Active
- 2016-12-02 KR KR1020187018588A patent/KR102678264B1/ko active Active
- 2016-12-02 ES ES16813199T patent/ES2858312T3/es active Active
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- 2016-12-02 WO PCT/US2016/064562 patent/WO2017096130A1/en not_active Ceased
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2022
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