JP2019518041A5 - - Google Patents
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- JP2019518041A5 JP2019518041A5 JP2018565337A JP2018565337A JP2019518041A5 JP 2019518041 A5 JP2019518041 A5 JP 2019518041A5 JP 2018565337 A JP2018565337 A JP 2018565337A JP 2018565337 A JP2018565337 A JP 2018565337A JP 2019518041 A5 JP2019518041 A5 JP 2019518041A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- independently
- alkyl
- heterocyclyl
- dimethoxyphenyl
- 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 88
- 125000000623 heterocyclic group Chemical group 0.000 claims 54
- 229910052801 chlorine Inorganic materials 0.000 claims 48
- 229910052731 fluorine Inorganic materials 0.000 claims 48
- 229910052739 hydrogen Inorganic materials 0.000 claims 36
- 229910052794 bromium Inorganic materials 0.000 claims 35
- 125000004452 carbocyclyl group Chemical group 0.000 claims 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 15
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 206010019280 Heart failures Diseases 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 206010049694 Left Ventricular Dysfunction Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 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
- 238000007634 remodeling Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- RHKWGLBBPGYJMB-UHFFFAOYSA-N 3-(2-bromophenyl)sulfonyl-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound BrC1=C(C=CC=C1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)=O RHKWGLBBPGYJMB-UHFFFAOYSA-N 0.000 claims 1
- KOMVDOOSGHBVJK-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonyl-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N1)S(=O)(=O)C1=CC=C(N)C=C1)C1=C(OC)C=CC=C1OC KOMVDOOSGHBVJK-UHFFFAOYSA-N 0.000 claims 1
- SEZFZPXQDUZSAX-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound BrC1=CC=C(C=C1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O SEZFZPXQDUZSAX-UHFFFAOYSA-N 0.000 claims 1
- VGSUVWWPJAMMJY-UHFFFAOYSA-N 3-(4-cyclopropylphenyl)sulfonyl-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C1(CC1)C1=CC=C(C=C1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O VGSUVWWPJAMMJY-UHFFFAOYSA-N 0.000 claims 1
- YRQOKVFEWYCLSW-UHFFFAOYSA-N 3-(5-bromopyridin-2-yl)sulfonyl-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound BrC=1C=CC(=NC=1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)=O YRQOKVFEWYCLSW-UHFFFAOYSA-N 0.000 claims 1
- RDQVGRZONDVMSX-UHFFFAOYSA-N 3-(benzenesulfonyl)-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC RDQVGRZONDVMSX-UHFFFAOYSA-N 0.000 claims 1
- QPGNLXLJDOVGHI-UHFFFAOYSA-N 3-[4-(3,5-dichloro-2-oxopyridin-1-yl)phenyl]sulfonyl-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound ClC=1C(N(C=C(C=1)Cl)C1=CC=C(C=C1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O)=O QPGNLXLJDOVGHI-UHFFFAOYSA-N 0.000 claims 1
- DFJHNNVTOWIDFA-UHFFFAOYSA-N 3-[4-(5-chloro-2-oxopyridin-1-yl)phenyl]sulfonyl-5-(2,6-dimethoxyphenyl)-6-(4-fluorophenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound ClC=1C=CC(N(C=1)C1=CC=C(C=C1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)C1=CC=C(C=C1)F)=O)=O DFJHNNVTOWIDFA-UHFFFAOYSA-N 0.000 claims 1
- VXQZMVJEQSMALN-UHFFFAOYSA-N 3-[4-(5-chloro-2-oxopyridin-1-yl)phenyl]sulfonyl-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound ClC=1C=CC(N(C=1)C1=CC=C(C=C1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O)=O VXQZMVJEQSMALN-UHFFFAOYSA-N 0.000 claims 1
- YJAXSCCOLRKICA-UHFFFAOYSA-N 4-[6-[[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]sulfonyl]pyridin-3-yl]-N-cyclopropylbenzamide Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=N1)C1=CC=C(C(=O)NC2CC2)C=C1)O)C1=C(C=CC=C1OC)OC YJAXSCCOLRKICA-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- AXXOMXAVPGXZEP-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-3-[4-(2-fluoro-3-methylpyridin-4-yl)phenyl]sulfonyl-6-(4-fluorophenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(NC=1C1=CC=C(C=C1)F)=O)S(=O)(=O)C1=CC=C(C=C1)C1=C(C(=NC=C1)F)C)O AXXOMXAVPGXZEP-UHFFFAOYSA-N 0.000 claims 1
- IYMDZTURWKTUFU-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-3-[4-(6-fluoro-2-methylpyridin-3-yl)phenyl]sulfonyl-6-(4-fluorophenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(NC=1C1=CC=C(C=C1)F)=O)S(=O)(=O)C1=CC=C(C=C1)C=1C(=NC(=CC=1)F)C)O IYMDZTURWKTUFU-UHFFFAOYSA-N 0.000 claims 1
- ATRPZPMAMHVALG-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[4-(6-fluoropyridin-3-yl)phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(NC=1COCC)=O)S(=O)(=O)C1=CC=C(C=C1)C=1C=NC(=CC=1)F)O ATRPZPMAMHVALG-UHFFFAOYSA-N 0.000 claims 1
- QBPNVJMNHFAIJS-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-3-[4-(5-methyl-2-oxopyridin-1-yl)phenyl]sulfonyl-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(NC=1COCC)=O)S(=O)(=O)C1=CC=C(C=C1)N1C(C=CC(=C1)C)=O)O QBPNVJMNHFAIJS-UHFFFAOYSA-N 0.000 claims 1
- FFVKNNGWLRNHGW-UHFFFAOYSA-N 6-butyl-3-(4-cyclopropylphenyl)sulfonyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C1CC1)O)C1=C(C=CC=C1OC)OC FFVKNNGWLRNHGW-UHFFFAOYSA-N 0.000 claims 1
- JCGRIDPLZFGJGU-UHFFFAOYSA-N 6-butyl-3-(5-cyclopropylpyridin-2-yl)sulfonyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N1)S(=O)(=O)C1=NC=C(C=C1)C1CC1)C1=C(OC)C=CC=C1OC JCGRIDPLZFGJGU-UHFFFAOYSA-N 0.000 claims 1
- NSUYFGWGSNRTKY-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(2-fluoro-3-methylpyridin-4-yl)phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C1=C(C(=NC=C1)F)C)O)C1=C(C=CC=C1OC)OC NSUYFGWGSNRTKY-UHFFFAOYSA-N 0.000 claims 1
- MTYJKZOPCQSJIV-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(4-fluoroanilino)phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)NC1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC MTYJKZOPCQSJIV-UHFFFAOYSA-N 0.000 claims 1
- SKKNZYMYHBMECJ-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(4-fluorophenyl)phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC SKKNZYMYHBMECJ-UHFFFAOYSA-N 0.000 claims 1
- UZPVVVHSEGAOBX-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(5-fluoropyridin-3-yl)phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C=1C=NC=C(C=1)F)O)C1=C(C=CC=C1OC)OC UZPVVVHSEGAOBX-UHFFFAOYSA-N 0.000 claims 1
- CKDBIEKHTGMQPF-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(6-fluoro-2-methylpyridin-3-yl)phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C=1C(=NC(=CC=1)F)C)O)C1=C(C=CC=C1OC)OC CKDBIEKHTGMQPF-UHFFFAOYSA-N 0.000 claims 1
- ZDEDUWSKYFVRND-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(6-fluoropyridin-3-yl)phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C=1C=NC(=CC=1)F)O)C1=C(C=CC=C1OC)OC ZDEDUWSKYFVRND-UHFFFAOYSA-N 0.000 claims 1
- VXQLNZPIYSNNGG-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-[(6-fluoropyridin-3-yl)amino]phenyl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound CCCCc1[nH]c(=O)c(c(O)c1-c1c(OC)cccc1OC)S(=O)(=O)c1ccc(Nc2ccc(F)nc2)cc1 VXQLNZPIYSNNGG-UHFFFAOYSA-N 0.000 claims 1
- ANZNWCLKXLYALA-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(2-fluoro-3-methylpyridin-4-yl)pyridin-2-yl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=N1)C1=C(C(=NC=C1)F)C)O)C1=C(C=CC=C1OC)OC ANZNWCLKXLYALA-UHFFFAOYSA-N 0.000 claims 1
- WBUSJEHRMXMVOC-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(3-fluoro-2-methylphenyl)pyridin-2-yl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C1=C(C(=CC=C1)F)C)O)C1=C(C=CC=C1OC)OC WBUSJEHRMXMVOC-UHFFFAOYSA-N 0.000 claims 1
- YQLUZSXIVGPUCN-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(3-fluoro-2-morpholin-4-ylpyridin-4-yl)pyridin-2-yl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=N1)C1=C(C(=NC=C1)N1CCOCC1)F)O)C1=C(C=CC=C1OC)OC YQLUZSXIVGPUCN-UHFFFAOYSA-N 0.000 claims 1
- GTTMRBPLZUUSPF-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(4-fluoro-2-methylphenyl)pyridin-2-yl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C1=C(C=C(C=C1)F)C)O)C1=C(C=CC=C1OC)OC GTTMRBPLZUUSPF-UHFFFAOYSA-N 0.000 claims 1
- UHQRIAHTRNOZSX-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(4-fluorophenyl)pyridin-2-yl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC UHQRIAHTRNOZSX-UHFFFAOYSA-N 0.000 claims 1
- SFXPJDSYBLMNPP-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(6-fluoro-2-methylpyridin-3-yl)pyridin-2-yl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=N1)C=1C(=NC(=CC=1)F)C)O)C1=C(C=CC=C1OC)OC SFXPJDSYBLMNPP-UHFFFAOYSA-N 0.000 claims 1
- WOYZFIJYXPXJSW-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(6-fluoropyridin-3-yl)pyridin-2-yl]sulfonyl-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=N1)C=1C=NC(=CC=1)F)O)C1=C(C=CC=C1OC)OC WOYZFIJYXPXJSW-UHFFFAOYSA-N 0.000 claims 1
- DALCSZZVWMABKI-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(1H-1,2,4-triazol-5-ylsulfonyl)-1H-pyridin-2-one Chemical compound N=1N=C(NC=1)S(=O)(=O)C=1C(NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)=O DALCSZZVWMABKI-UHFFFAOYSA-N 0.000 claims 1
- SFSQVDPNMDBBGT-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(5-methylpyridin-2-yl)sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C)O)C1=C(C=CC=C1OC)OC SFSQVDPNMDBBGT-UHFFFAOYSA-N 0.000 claims 1
- ZIDCRESPVGRKFO-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(5-prop-1-en-2-ylpyridin-2-yl)sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C(=C)C)O)C1=C(C=CC=C1OC)OC ZIDCRESPVGRKFO-UHFFFAOYSA-N 0.000 claims 1
- FOERRAJLRUTVGO-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(5-propan-2-ylpyridin-2-yl)sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C(C)C)O)C1=C(C=CC=C1OC)OC FOERRAJLRUTVGO-UHFFFAOYSA-N 0.000 claims 1
- YVAQLZOVQXLZTG-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(2-methoxypyridin-3-yl)phenyl]sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C=1C(=NC=CC=1)OC)O)C1=C(C=CC=C1OC)OC YVAQLZOVQXLZTG-UHFFFAOYSA-N 0.000 claims 1
- UQVNEUPKHBEUDA-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(2-oxopyridin-1-yl)phenyl]sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)N1C(C=CC=C1)=O)O)C1=C(C=CC=C1OC)OC UQVNEUPKHBEUDA-UHFFFAOYSA-N 0.000 claims 1
- QPOOGLDKJWMVCE-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(3-methylpyridin-4-yl)phenyl]sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=C1)C1=C(C=NC=C1)C)O)C1=C(C=CC=C1OC)OC QPOOGLDKJWMVCE-UHFFFAOYSA-N 0.000 claims 1
- DVIUBNNUBNQQML-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[5-(2-methoxypyridin-4-yl)pyridin-2-yl]sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=N1)C1=CC(=NC=C1)OC)O)C1=C(C=CC=C1OC)OC DVIUBNNUBNQQML-UHFFFAOYSA-N 0.000 claims 1
- ZAJQVIUYVQZSJV-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[5-(2-methylphenyl)pyridin-2-yl]sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C1=C(C=CC=C1)C)O)C1=C(C=CC=C1OC)OC ZAJQVIUYVQZSJV-UHFFFAOYSA-N 0.000 claims 1
- KMOQDFGDKDCVMH-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[5-(3-methylpyridin-4-yl)pyridin-2-yl]sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=CC=C(C=N1)C1=C(C=NC=C1)C)O)C1=C(C=CC=C1OC)OC KMOQDFGDKDCVMH-UHFFFAOYSA-N 0.000 claims 1
- DGAUGMBXOISKQI-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]sulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=C(C=C1)C1=CC=C(C=C1)OC(F)(F)F)O)C1=C(C=CC=C1OC)OC DGAUGMBXOISKQI-UHFFFAOYSA-N 0.000 claims 1
- URFUOQAXZULVEB-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-pyridin-2-ylsulfonyl-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)S(=O)(=O)C1=NC=CC=C1)O)C1=C(C=CC=C1OC)OC URFUOQAXZULVEB-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
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- URMPVRWGQZRTAL-UHFFFAOYSA-N N-[4-[[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]sulfonyl]phenyl]-4-fluorobenzamide Chemical compound CCCCC1=C(C(O)=C(C(=O)N1)S(=O)(=O)C1=CC=C(NC(=O)C2=CC=C(F)C=C2)C=C1)C1=C(OC)C=CC=C1OC URMPVRWGQZRTAL-UHFFFAOYSA-N 0.000 claims 1
- 208000008253 Systolic Heart Failure Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
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- -1 tert-Butyl (4-((6-butyl-5- (2,6-dimethoxyphenyl) -4-hydroxy-2-oxo-1,2-dihydropyridine-3-yl) sulfonyl) phenyl) carbamate Chemical compound 0.000 claims 1
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| 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 |
| EP3452466B1 (en) | 2016-05-03 | 2020-08-12 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| WO2017218633A1 (en) | 2016-06-14 | 2017-12-21 | Bristol-Myers Squibb Company | 6-hydroxy-5-(phenyl/heteroarylsulfonyl)pyrimidin-4(1h)-one as apj agonists |
| KR102521956B1 (ko) | 2016-10-14 | 2023-04-14 | 브리스톨-마이어스 스큅 컴퍼니 | 3-술포닐-5-아미노피리딘-2,4-디올 apj 효능제 |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| US10906890B2 (en) | 2016-11-16 | 2021-02-02 | Amgen Inc. | Triazole phenyl compounds as agonists of the APJ receptor |
| WO2018093577A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the apj receptor |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| EP3541802B1 (en) | 2016-11-16 | 2025-01-01 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| WO2019089335A1 (en) | 2017-11-03 | 2019-05-09 | Amgen Inc. | Fused triazole agonists of the apj receptor |
| EP3788037A1 (en) | 2018-05-01 | 2021-03-10 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| CN113166081A (zh) | 2018-11-13 | 2021-07-23 | 诺华股份有限公司 | 用于治疗与nlrp活性相关的病症的化合物和组合物 |
| CN113015730A (zh) * | 2018-11-13 | 2021-06-22 | 诺华股份有限公司 | 用于治疗与nlrp活性相关的病症的化合物和组合物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3847927A (en) * | 1972-12-20 | 1974-11-12 | Dow Chemical Co | Sulfur-containing hydroxypyridones |
| EE9600044A (et) * | 1993-11-19 | 1996-10-15 | Parke, Davis & Company | Püranooni derivaadid kui proteaasi inhibiitorid ja viirusevastased toimeained |
| SK283240B6 (sk) * | 1993-11-19 | 2003-04-01 | Parke, Davis & Company | 5,6-Dihydropyrónové deriváty ako inhibítory proteázy a protivírusové činidlá a farmaceutická kompozícia obsahujúca tieto deriváty |
| ES2155134T3 (es) * | 1994-07-29 | 2001-05-01 | Suntory Ltd | Derivados de imidazolidina y su utilizacion. |
| JP3537231B2 (ja) * | 1995-07-24 | 2004-06-14 | 第一サントリーファーマ株式会社 | ヒダントイン誘導体およびその用途 |
| US10570128B2 (en) | 2014-05-28 | 2020-02-25 | Sanford Burnham Prebys Medical Discovery Institute | Agonists of the apelin receptor and methods of use thereof |
| 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 |
| 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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- 2017-06-14 US US16/309,168 patent/US10889565B2/en active Active
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- 2017-06-14 CN CN201780049629.7A patent/CN109641843B/zh active Active
- 2017-06-14 WO PCT/US2017/037370 patent/WO2017218617A1/en not_active Ceased
- 2017-06-14 JP JP2018565337A patent/JP6962941B2/ja active Active
- 2017-06-14 ES ES17731794T patent/ES2844184T3/es active Active
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