JP2018530591A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018530591A5 JP2018530591A5 JP2018519425A JP2018519425A JP2018530591A5 JP 2018530591 A5 JP2018530591 A5 JP 2018530591A5 JP 2018519425 A JP2018519425 A JP 2018519425A JP 2018519425 A JP2018519425 A JP 2018519425A JP 2018530591 A5 JP2018530591 A5 JP 2018530591A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- dimethoxyphenyl
- pyridine
- diol
- butyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 52
- 125000000623 heterocyclic group Chemical group 0.000 claims 38
- 229910052801 chlorine Inorganic materials 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 229910052731 fluorine Inorganic materials 0.000 claims 26
- 229910052799 carbon Inorganic materials 0.000 claims 24
- 229910052794 bromium Inorganic materials 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004452 carbocyclyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- -1 CN Inorganic materials 0.000 claims 10
- 229910004013 NO 2 Inorganic materials 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- JXXWGJDDGHLALL-UHFFFAOYSA-N 6-butyl-3-[4-(5-chloropyridin-2-yl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=NC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC JXXWGJDDGHLALL-UHFFFAOYSA-N 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- JWHIEVXUXFAQDJ-UHFFFAOYSA-N 3-[3-(2,4-difluorophenyl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound CCOCC1=C(C(O)=C(C(=O)N2CCC(C2)C2=C(F)C=C(F)C=C2)C(=O)N1)C1=C(OC)C=CC=C1OC JWHIEVXUXFAQDJ-UHFFFAOYSA-N 0.000 claims 4
- TYNFGDMXKBRIMD-UHFFFAOYSA-N 3-[3-(2,6-difluorophenyl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound CCOCC1=C(C(O)=C(C(=O)N2CCC(C2)C2=C(F)C=CC=C2F)C(=O)N1)C1=C(OC)C=CC=C1OC TYNFGDMXKBRIMD-UHFFFAOYSA-N 0.000 claims 4
- ISWHIVGTKAPCBD-UHFFFAOYSA-N 3-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-5-(3-methoxyphenyl)-6-(2-methyl-1,3-thiazol-4-yl)-1H-pyridin-2-one Chemical compound COc1cccc(c1)-c1c(O)c(C(=O)N2CCC(C2)c2ncc(F)cc2F)c(=O)[nH]c1-c1csc(C)n1 ISWHIVGTKAPCBD-UHFFFAOYSA-N 0.000 claims 4
- LSQPBZVEEYPZNT-UHFFFAOYSA-N 3-[3-(5-chloropyridin-2-yl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound ClC=1C=CC(=NC=1)C1CN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)O LSQPBZVEEYPZNT-UHFFFAOYSA-N 0.000 claims 4
- MJRQWNRBGLQROP-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[3-(2-fluorophenyl)pyrrolidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1COCC)O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O MJRQWNRBGLQROP-UHFFFAOYSA-N 0.000 claims 4
- STPCTGAXOIRZLX-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(ethylaminomethyl)-3-[3-(2-fluorophenyl)pyrrolidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1CNCC)O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O STPCTGAXOIRZLX-UHFFFAOYSA-N 0.000 claims 4
- PAHBCVGKVFBQCH-UHFFFAOYSA-N 6-butyl-3-[3-(2-chlorophenyl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=C(C=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC PAHBCVGKVFBQCH-UHFFFAOYSA-N 0.000 claims 4
- SWMRKJKGMIVBQC-UHFFFAOYSA-N 6-butyl-3-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-5-(3-methoxyphenyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)O)C1=CC(=CC=C1)OC SWMRKJKGMIVBQC-UHFFFAOYSA-N 0.000 claims 4
- KEKVIUIKJARJEV-UHFFFAOYSA-N 6-butyl-3-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-5-[3-(hydroxymethyl)phenyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)O)C1=CC(=CC=C1)CO KEKVIUIKJARJEV-UHFFFAOYSA-N 0.000 claims 4
- KNNQFRTUAOSUPW-UHFFFAOYSA-N 6-butyl-3-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)O)C1=C(C=CC=C1OC)OC KNNQFRTUAOSUPW-UHFFFAOYSA-N 0.000 claims 4
- BJRABZGGXKCRFF-UHFFFAOYSA-N 6-butyl-3-[3-(3-chlorophenyl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=CC(=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC BJRABZGGXKCRFF-UHFFFAOYSA-N 0.000 claims 4
- PQBPXJCTSKAMJZ-UHFFFAOYSA-N 6-butyl-3-[3-(5-chloro-3-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCC(C2)C2=NC=C(Cl)C=C2F)C(=O)N1)C1=C(OC)C=CC=C1OC PQBPXJCTSKAMJZ-UHFFFAOYSA-N 0.000 claims 4
- QLRHTCHILRFJSZ-UHFFFAOYSA-N 6-butyl-3-[3-(5-chloropyridin-2-yl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC QLRHTCHILRFJSZ-UHFFFAOYSA-N 0.000 claims 4
- UOHRPIGTAUTOKW-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[3-(3-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=NC=CC=C1F)O)C1=C(C=CC=C1OC)OC UOHRPIGTAUTOKW-UHFFFAOYSA-N 0.000 claims 4
- FYRCMPVHDQPOHS-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[3-(4-fluorophenyl)pyrrolidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC FYRCMPVHDQPOHS-UHFFFAOYSA-N 0.000 claims 4
- PFURAOMBNMGHKV-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[3-(5-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC PFURAOMBNMGHKV-UHFFFAOYSA-N 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000003003 spiro group Chemical group 0.000 claims 4
- GUFNVUDXTINVTO-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(3-propyl-1,2,4-oxadiazol-5-yl)piperidine-1-carbonyl]-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCC(CC2)C2=NC(CCC)=NO2)C(O)=N1)C1=C(OC)C=CC=C1OC GUFNVUDXTINVTO-UHFFFAOYSA-N 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 2
- YEWCQODMEFGLMI-UHFFFAOYSA-N 1'-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridine-3-carbonyl]spiro[1,3-dihydroquinoline-4,4'-piperidine]-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC2(CC(NC3=CC=CC=C23)=O)CC1)O)C1=C(C=CC=C1OC)OC YEWCQODMEFGLMI-UHFFFAOYSA-N 0.000 claims 2
- XYEOQMQNEUFXJB-UHFFFAOYSA-N 1'-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridine-3-carbonyl]spiro[1H-3,1-benzoxazine-4,4'-piperidine]-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC2(CC1)OC(NC1=C2C=CC=C1)=O)O)C1=C(C=CC=C1OC)OC XYEOQMQNEUFXJB-UHFFFAOYSA-N 0.000 claims 2
- FRXYVYVLLWBSEB-UHFFFAOYSA-N 2-[3-[2-butyl-5-[4-[(2,3-difluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-6-oxo-1H-pyridin-3-yl]phenyl]acetonitrile Chemical compound C(CCC)C1=NC(=C(C(=C1C=1C=C(C=CC=1)CC#N)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)F)F)O FRXYVYVLLWBSEB-UHFFFAOYSA-N 0.000 claims 2
- XEOZTKITOZQOJR-UHFFFAOYSA-N 3-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=NC=CC=1O)O XEOZTKITOZQOJR-UHFFFAOYSA-N 0.000 claims 2
- RKAQGZNSSXXHGN-UHFFFAOYSA-N 3-(4-benzhydrylpiperazine-1-carbonyl)-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC RKAQGZNSSXXHGN-UHFFFAOYSA-N 0.000 claims 2
- QBRYZFLMFWWEOG-UHFFFAOYSA-N 3-(4-benzoylpiperazine-1-carbonyl)-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(C1=CC=CC=C1)(=O)N1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O QBRYZFLMFWWEOG-UHFFFAOYSA-N 0.000 claims 2
- VGLSSGXIWVAQGC-UHFFFAOYSA-N 3-(4-benzylpiperidine-1-carbonyl)-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(C1=CC=CC=C1)C1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O VGLSSGXIWVAQGC-UHFFFAOYSA-N 0.000 claims 2
- BEKNNWPDAWWCKK-UHFFFAOYSA-N 3-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-6-(4-fluorophenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound FC=1C(=NC=C(C=1)F)C1CN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)C1=CC=C(C=C1)F)O BEKNNWPDAWWCKK-UHFFFAOYSA-N 0.000 claims 2
- HQQPPLDRRWXRLW-UHFFFAOYSA-N 3-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound FC=1C(=NC=C(C=1)F)C1CN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)O HQQPPLDRRWXRLW-UHFFFAOYSA-N 0.000 claims 2
- ZVIMEZNEMDYJPV-UHFFFAOYSA-N 3-[4-(1,2-benzothiazol-3-yl)piperazine-1-carbonyl]-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound S1N=C(C2=C1C=CC=C2)N1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O ZVIMEZNEMDYJPV-UHFFFAOYSA-N 0.000 claims 2
- QDSLOWFLSKKPFS-UHFFFAOYSA-N 3-[4-(1,3-benzothiazol-2-yl)piperazine-1-carbonyl]-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound S1C(=NC2=C1C=CC=C2)N1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O QDSLOWFLSKKPFS-UHFFFAOYSA-N 0.000 claims 2
- LEEJSVUKJKLOHX-UHFFFAOYSA-N 3-[4-(1,3-benzothiazol-2-yl)piperidine-1-carbonyl]-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound S1C(=NC2=C1C=CC=C2)C1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O LEEJSVUKJKLOHX-UHFFFAOYSA-N 0.000 claims 2
- QTMUHSVYJGYWNS-UHFFFAOYSA-N 3-[4-(1,3-benzoxazol-2-yl)piperidine-1-carbonyl]-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound O1C(=NC2=C1C=CC=C2)C1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O QTMUHSVYJGYWNS-UHFFFAOYSA-N 0.000 claims 2
- AGDFNJVHDNKBLX-UHFFFAOYSA-N 3-[4-[(2,3-dichlorophenyl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound ClC1=C(C=CC=C1Cl)CN1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)O AGDFNJVHDNKBLX-UHFFFAOYSA-N 0.000 claims 2
- WATKCBGABFQNRI-UHFFFAOYSA-N 3-[4-[(2,3-difluorophenyl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-1H-pyridin-2-one Chemical compound FC1=C(C=CC=C1F)CN1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)O WATKCBGABFQNRI-UHFFFAOYSA-N 0.000 claims 2
- DIJRZAGOFDBDGX-UHFFFAOYSA-N 3-[4-[(2-bromo-5-fluorophenyl)methyl]piperidine-1-carbonyl]-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound BrC1=C(C=C(C=C1)F)CC1CCN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O DIJRZAGOFDBDGX-UHFFFAOYSA-N 0.000 claims 2
- VRLNCNWNDNXTCM-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-3-[4-[(3-fluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-6-(2-methoxyethyl)-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1CCOC)O)C(=O)N1CCN(CC1)CC1=CC(=CC=C1)F)O VRLNCNWNDNXTCM-UHFFFAOYSA-N 0.000 claims 2
- SEXZYTNOKJFQTI-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[4-[(2-fluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1COCC)O)C(=O)N1CCN(CC1)CC1=C(C=CC=C1)F)O SEXZYTNOKJFQTI-UHFFFAOYSA-N 0.000 claims 2
- ZLRDNEZLCPNZKE-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[4-[(3-fluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1COCC)O)C(=O)N1CCN(CC1)CC1=CC(=CC=C1)F)O ZLRDNEZLCPNZKE-UHFFFAOYSA-N 0.000 claims 2
- MORAXWPILAFWAK-SFHVURJKSA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-3-[(3R)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1COCC)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O MORAXWPILAFWAK-SFHVURJKSA-N 0.000 claims 2
- ZLNULAJDQCJLOL-IBGZPJMESA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-3-[(3S)-3-phenylmethoxypyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(C1=CC=CC=C1)O[C@@H]1CN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)COCC)O ZLNULAJDQCJLOL-IBGZPJMESA-N 0.000 claims 2
- MORAXWPILAFWAK-GOSISDBHSA-N 5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-3-[(3S)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1COCC)O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O MORAXWPILAFWAK-GOSISDBHSA-N 0.000 claims 2
- IQRUQXXCIDNXLO-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(ethylaminomethyl)-3-[3-(3-fluorophenyl)pyrrolidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1CNCC)O)C(=O)N1CC(CC1)C1=CC(=CC=C1)F)O IQRUQXXCIDNXLO-UHFFFAOYSA-N 0.000 claims 2
- UAHUYSRHLWEMMI-UHFFFAOYSA-N 6-(ethoxymethyl)-3-[4-[(3-fluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-5-(2-methoxyphenyl)-1H-pyridin-2-one Chemical compound C(C)OCC1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=CC(=CC=C1)F)O)C1=C(C=CC=C1)OC UAHUYSRHLWEMMI-UHFFFAOYSA-N 0.000 claims 2
- QSHXHZFCIYLKBU-UHFFFAOYSA-N 6-butyl-3-(4-cyclohexylpiperazine-1-carbonyl)-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1CCCCC1)O)C1=C(C=CC=C1OC)OC QSHXHZFCIYLKBU-UHFFFAOYSA-N 0.000 claims 2
- DBUHEXRTLWRNBS-UHFFFAOYSA-N 6-butyl-3-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-5-(3-propan-2-ylphenyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)O)C1=CC(=CC=C1)C(C)C DBUHEXRTLWRNBS-UHFFFAOYSA-N 0.000 claims 2
- ZKJPREGZORLOPY-UHFFFAOYSA-N 6-butyl-3-[3-(3-chlorophenyl)azetidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(C1)C1=CC(=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC ZKJPREGZORLOPY-UHFFFAOYSA-N 0.000 claims 2
- VWJYLLQLCPPMLL-UHFFFAOYSA-N 6-butyl-3-[3-[(2,3-difluorophenyl)methoxy]azetidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(C1)OCC1=C(C(=CC=C1)F)F)O)C1=C(C=CC=C1OC)OC VWJYLLQLCPPMLL-UHFFFAOYSA-N 0.000 claims 2
- MYVXXFTUMSCSBA-UHFFFAOYSA-N 6-butyl-3-[3-[4-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-1,3-thiazol-2-yl]pyrrolidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCC(C2)C2=NC(=C(C)S2)C2=C(Cl)C=C(OC)C(C)=C2)C(O)=N1)C1=C(OC)C=CC=C1OC MYVXXFTUMSCSBA-UHFFFAOYSA-N 0.000 claims 2
- BYBOHPULIGDKJB-UHFFFAOYSA-N 6-butyl-3-[4-(2,3-dichlorobenzoyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C(C1=C(C(=CC=C1)Cl)Cl)=O)O)C1=C(C=CC=C1OC)OC BYBOHPULIGDKJB-UHFFFAOYSA-N 0.000 claims 2
- IDNNPXOEIGAVEZ-UHFFFAOYSA-N 6-butyl-3-[4-(2,3-difluorobenzoyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C(C1=C(C(=CC=C1)F)F)=O)O)C1=C(C=CC=C1OC)OC IDNNPXOEIGAVEZ-UHFFFAOYSA-N 0.000 claims 2
- LQCZWCZUQUOOTK-UHFFFAOYSA-N 6-butyl-3-[4-(2-chlorophenyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=C(C=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC LQCZWCZUQUOOTK-UHFFFAOYSA-N 0.000 claims 2
- GUJCGYYABOOGPH-UHFFFAOYSA-N 6-butyl-3-[4-(2-chlorophenyl)piperidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)C1=C(C=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC GUJCGYYABOOGPH-UHFFFAOYSA-N 0.000 claims 2
- UFEZPTRCDRMMHG-UHFFFAOYSA-N 6-butyl-3-[4-(3-chlorophenyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=CC(=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC UFEZPTRCDRMMHG-UHFFFAOYSA-N 0.000 claims 2
- MCQBRBORRICOPD-UHFFFAOYSA-N 6-butyl-3-[4-(3-chlorophenyl)piperidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)C1=CC(=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC MCQBRBORRICOPD-UHFFFAOYSA-N 0.000 claims 2
- TZFFAXXOWWNCHB-UHFFFAOYSA-N 6-butyl-3-[4-(4-chlorophenyl)-4-hydroxypiperidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)(O)C1=CC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC TZFFAXXOWWNCHB-UHFFFAOYSA-N 0.000 claims 2
- CJTHQTYFUMVVRG-UHFFFAOYSA-N 6-butyl-3-[4-(4-chlorophenyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=CC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC CJTHQTYFUMVVRG-UHFFFAOYSA-N 0.000 claims 2
- QAVTXIWGNKLILT-UHFFFAOYSA-N 6-butyl-3-[4-(5-chloropyridin-2-yl)oxypiperidine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)OC1=NC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC QAVTXIWGNKLILT-UHFFFAOYSA-N 0.000 claims 2
- LAFGAVGKUPAUJF-UHFFFAOYSA-N 6-butyl-3-[4-(5-chloropyridine-2-carbonyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C(=O)C1=NC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC LAFGAVGKUPAUJF-UHFFFAOYSA-N 0.000 claims 2
- SLXDSRXVIGBRNZ-UHFFFAOYSA-N 6-butyl-3-[4-(cyclohexylmethyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1CCCCC1)O)C1=C(C=CC=C1OC)OC SLXDSRXVIGBRNZ-UHFFFAOYSA-N 0.000 claims 2
- RWSAPGOQPPRPTF-UHFFFAOYSA-N 6-butyl-3-[4-(cyclopropylmethyl)piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1CC1)O)C1=C(C=CC=C1OC)OC RWSAPGOQPPRPTF-UHFFFAOYSA-N 0.000 claims 2
- UGIXRSNRUXSCID-UHFFFAOYSA-N 6-butyl-3-[4-[(2,3-dichlorophenyl)methyl]piperazine-1-carbonyl]-5-(2,3-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)Cl)Cl)O)C1=C(C(=CC=C1)OC)OC UGIXRSNRUXSCID-UHFFFAOYSA-N 0.000 claims 2
- FHZCKUYQJUXHPH-UHFFFAOYSA-N 6-butyl-3-[4-[(2,3-dichlorophenyl)methyl]piperazine-1-carbonyl]-5-(2,5-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)Cl)Cl)O)C1=C(C=CC(=C1)OC)OC FHZCKUYQJUXHPH-UHFFFAOYSA-N 0.000 claims 2
- UPWPJDUMNWHYHZ-UHFFFAOYSA-N 6-butyl-3-[4-[(2,3-dichlorophenyl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)Cl)Cl)O)C1=C(C=CC=C1OC)OC UPWPJDUMNWHYHZ-UHFFFAOYSA-N 0.000 claims 2
- FHUQYVQCIQJAHF-UHFFFAOYSA-N 6-butyl-3-[4-[(2,3-difluorophenyl)methyl]piperazine-1-carbonyl]-5-(2,3-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)F)F)O)C1=C(C(=CC=C1)OC)OC FHUQYVQCIQJAHF-UHFFFAOYSA-N 0.000 claims 2
- FFORQQRXYATGPS-UHFFFAOYSA-N 6-butyl-3-[4-[(2,3-difluorophenyl)methyl]piperazine-1-carbonyl]-5-(2,5-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)F)F)O)C1=C(C=CC(=C1)OC)OC FFORQQRXYATGPS-UHFFFAOYSA-N 0.000 claims 2
- GVUYOSRUKWPPQX-UHFFFAOYSA-N 6-butyl-3-[4-[(2,3-difluorophenyl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)F)F)O)C1=C(C=CC=C1OC)OC GVUYOSRUKWPPQX-UHFFFAOYSA-N 0.000 claims 2
- SYJZPHVLKKFXOW-UHFFFAOYSA-N 6-butyl-3-[4-[(2,4-dichlorophenyl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C=C(C=C1)Cl)Cl)O)C1=C(C=CC=C1OC)OC SYJZPHVLKKFXOW-UHFFFAOYSA-N 0.000 claims 2
- OHBYNROWBKOKQX-UHFFFAOYSA-N 6-butyl-3-[4-[(2,5-difluorophenyl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C=CC(=C1)F)F)O)C1=C(C=CC=C1OC)OC OHBYNROWBKOKQX-UHFFFAOYSA-N 0.000 claims 2
- BFAVJIZCJXSCMR-UHFFFAOYSA-N 6-butyl-3-[4-[(4-chlorophenyl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=CC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC BFAVJIZCJXSCMR-UHFFFAOYSA-N 0.000 claims 2
- QQFKIIYPEGDIRN-UHFFFAOYSA-N 6-butyl-3-[4-[(6-chloropyridin-2-yl)methyl]piperazine-1-carbonyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=NC(=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC QQFKIIYPEGDIRN-UHFFFAOYSA-N 0.000 claims 2
- RUJHNKADQHZZDS-QHCPKHFHSA-N 6-butyl-4-hydroxy-3-[(3R)-3-phenylpyrrolidine-1-carbonyl]-5-(3-propan-2-ylphenyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O)C1=CC(=CC=C1)C(C)C RUJHNKADQHZZDS-QHCPKHFHSA-N 0.000 claims 2
- KPIKYAWKTFSLOT-IBGZPJMESA-N 6-butyl-5-(2,5-dimethoxyphenyl)-4-hydroxy-3-[(3R)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O)C1=C(C=CC(=C1)OC)OC KPIKYAWKTFSLOT-IBGZPJMESA-N 0.000 claims 2
- KPIKYAWKTFSLOT-LJQANCHMSA-N 6-butyl-5-(2,5-dimethoxyphenyl)-4-hydroxy-3-[(3S)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O)C1=C(C=CC(=C1)OC)OC KPIKYAWKTFSLOT-LJQANCHMSA-N 0.000 claims 2
- IHOOFLBEFRNISQ-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[3-(3-fluoropyridin-2-yl)oxyazetidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CC(C1)OC1=NC=CC=C1F)O)C1=C(C=CC=C1OC)OC IHOOFLBEFRNISQ-UHFFFAOYSA-N 0.000 claims 2
- ARDLEWAHEZITSD-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(3-fluorobenzoyl)piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C(C1=CC(=CC=C1)F)=O)O)C1=C(C=CC=C1OC)OC ARDLEWAHEZITSD-UHFFFAOYSA-N 0.000 claims 2
- TYORUNWNAGCDHA-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-[(2-fluoro-3-methylphenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C(=CC=C1)C)F)O)C1=C(C=CC=C1OC)OC TYORUNWNAGCDHA-UHFFFAOYSA-N 0.000 claims 2
- WNKUPNMMDVIAJD-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-[(2-fluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC WNKUPNMMDVIAJD-UHFFFAOYSA-N 0.000 claims 2
- GUFPHRJNZDHUQT-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-[(3-fluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=CC(=CC=C1)F)O)C1=C(C=CC=C1OC)OC GUFPHRJNZDHUQT-UHFFFAOYSA-N 0.000 claims 2
- PQKJBACOPZUZLR-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-[(3-fluoropyridin-2-yl)methyl]piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=NC=CC=C1F)O)C1=C(C=CC=C1OC)OC PQKJBACOPZUZLR-UHFFFAOYSA-N 0.000 claims 2
- XIKCVOQQGJCBPC-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-[(4-fluorophenyl)methyl]piperazine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC XIKCVOQQGJCBPC-UHFFFAOYSA-N 0.000 claims 2
- CVSDIBBHLQRBTO-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(2-pyridin-2-ylpyrrolidine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1C(CCC1)C1=NC=CC=C1)O)C1=C(C=CC=C1OC)OC CVSDIBBHLQRBTO-UHFFFAOYSA-N 0.000 claims 2
- SYXJHTYOLFBZRR-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-hydroxy-4-phenylpiperidine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)O)C1=C(C=CC=C1OC)OC SYXJHTYOLFBZRR-UHFFFAOYSA-N 0.000 claims 2
- FOWGPJMHFKCABB-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-hydroxy-4-pyridin-3-ylpiperidine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)(C=1C=NC=CC=1)O)O)C1=C(C=CC=C1OC)OC FOWGPJMHFKCABB-UHFFFAOYSA-N 0.000 claims 2
- CIWWBPQENDKOJE-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-phenoxypiperidine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)OC1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC CIWWBPQENDKOJE-UHFFFAOYSA-N 0.000 claims 2
- PEWYHEGDTYBPSA-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-phenylpiperazine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC PEWYHEGDTYBPSA-UHFFFAOYSA-N 0.000 claims 2
- QUKFQELSHHQCEQ-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-phenylpiperidine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC QUKFQELSHHQCEQ-UHFFFAOYSA-N 0.000 claims 2
- GNWHXORETIYCQZ-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-pyridazin-3-ylpiperazine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C=1N=NC=CC=1)O)C1=C(C=CC=C1OC)OC GNWHXORETIYCQZ-UHFFFAOYSA-N 0.000 claims 2
- OPHWKTZOOCUDAI-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-pyridin-2-ylpiperazine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=NC=CC=C1)O)C1=C(C=CC=C1OC)OC OPHWKTZOOCUDAI-UHFFFAOYSA-N 0.000 claims 2
- KQRRAIWYFKBTNV-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-pyridin-4-ylpiperazine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=CC=NC=C1)O)C1=C(C=CC=C1OC)OC KQRRAIWYFKBTNV-UHFFFAOYSA-N 0.000 claims 2
- TWCXIZHJKPRIMU-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(4-pyrrolidin-1-ylpiperidine-1-carbonyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)N1CCCC1)O)C1=C(C=CC=C1OC)OC TWCXIZHJKPRIMU-UHFFFAOYSA-N 0.000 claims 2
- BCINEYMTISNZFK-IBGZPJMESA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[(3R)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC BCINEYMTISNZFK-IBGZPJMESA-N 0.000 claims 2
- ICXTZXJQTUBVHO-FQEVSTJZSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[(3S)-3-phenylmethoxypyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(C1=CC=CC=C1)O[C@@H]1CN(CC1)C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O ICXTZXJQTUBVHO-FQEVSTJZSA-N 0.000 claims 2
- BCINEYMTISNZFK-LJQANCHMSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[(3S)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC BCINEYMTISNZFK-LJQANCHMSA-N 0.000 claims 2
- OWDFUXRQUNAXRE-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(1-methylimidazol-2-yl)piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C=1N(C=CN=1)C)O)C1=C(C=CC=C1OC)OC OWDFUXRQUNAXRE-UHFFFAOYSA-N 0.000 claims 2
- KUGVUTDBIPOBKB-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(1-phenyltetrazol-5-yl)-1,4-diazepane-1-carbonyl]-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCCN(CC2)C2=NN=NN2C2=CC=CC=C2)C(O)=N1)C1=C(OC)C=CC=C1OC KUGVUTDBIPOBKB-UHFFFAOYSA-N 0.000 claims 2
- YTGFIQJVXSNSSP-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(1-phenyltetrazol-5-yl)piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCN(CC2)C2=NN=NN2C2=CC=CC=C2)C(O)=N1)C1=C(OC)C=CC=C1OC YTGFIQJVXSNSSP-UHFFFAOYSA-N 0.000 claims 2
- BAZAHPWKZBAPMC-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(1H-imidazol-5-yl)piperidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)C=1N=CNC=1)O)C1=C(C=CC=C1OC)OC BAZAHPWKZBAPMC-UHFFFAOYSA-N 0.000 claims 2
- ZWNOKHBGOOUECG-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(2-methoxyphenyl)piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=C(C=CC=C1)OC)O)C1=C(C=CC=C1OC)OC ZWNOKHBGOOUECG-UHFFFAOYSA-N 0.000 claims 2
- IMPRQMRJIGCQIP-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(2-methoxyphenyl)piperidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)C1=C(C=CC=C1)OC)O)C1=C(C=CC=C1OC)OC IMPRQMRJIGCQIP-UHFFFAOYSA-N 0.000 claims 2
- FWWZHDLTYGYTSF-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCN(CC2)C2=NC(=NS2)C2=CC=CC=C2)C(O)=N1)C1=C(OC)C=CC=C1OC FWWZHDLTYGYTSF-UHFFFAOYSA-N 0.000 claims 2
- MDMUEVODCXNPTO-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(3-phenyl-1H-pyrazol-5-yl)piperidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)C1=NNC(=C1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC MDMUEVODCXNPTO-UHFFFAOYSA-N 0.000 claims 2
- ZNJZUGNJQLLHRU-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)piperidine-1-carbonyl]-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCC(CC2)C2=NC(=NO2)C2=CC=CN=C2)C(O)=N1)C1=C(OC)C=CC=C1OC ZNJZUGNJQLLHRU-UHFFFAOYSA-N 0.000 claims 2
- HDADEMFJXRAUJB-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(4-methoxybenzoyl)piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C(C1=CC=C(C=C1)OC)=O)O)C1=C(C=CC=C1OC)OC HDADEMFJXRAUJB-UHFFFAOYSA-N 0.000 claims 2
- UNMQUACFIABFAY-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(4-methoxyphenyl)piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=CC=C(C=C1)OC)O)C1=C(C=CC=C1OC)OC UNMQUACFIABFAY-UHFFFAOYSA-N 0.000 claims 2
- WROQXFPQWUNIQF-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(5-methyl-1H-imidazol-4-yl)piperidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)C1=C(N=CN1)C)O)C1=C(C=CC=C1OC)OC WROQXFPQWUNIQF-UHFFFAOYSA-N 0.000 claims 2
- WEUGCKQKZYZKNZ-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-(pyridin-2-ylmethyl)piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=NC=CC=C1)O)C1=C(C=CC=C1OC)OC WEUGCKQKZYZKNZ-UHFFFAOYSA-N 0.000 claims 2
- QXEDHBPTCFNKCI-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-[(2-methylphenyl)methyl]piperidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCC(CC1)CC1=C(C=CC=C1)C)O)C1=C(C=CC=C1OC)OC QXEDHBPTCFNKCI-UHFFFAOYSA-N 0.000 claims 2
- XNAHSRPAEBCQHM-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=NC=CC=C1C(F)(F)F)O)C1=C(C=CC=C1OC)OC XNAHSRPAEBCQHM-UHFFFAOYSA-N 0.000 claims 2
- XAENNNIGURSVEU-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-[4-(2-methoxyethoxy)phenyl]piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=CC=C(C=C1)OCCOC)O)C1=C(C=CC=C1OC)OC XAENNNIGURSVEU-UHFFFAOYSA-N 0.000 claims 2
- XMKJTASDRFSEAG-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-[4-(trifluoromethyl)pyrimidin-2-yl]piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)C1=NC=CC(=N1)C(F)(F)F)O)C1=C(C=CC=C1OC)OC XMKJTASDRFSEAG-UHFFFAOYSA-N 0.000 claims 2
- JHFWPXHWYILCHT-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-[4-[[3-(trifluoromethyl)phenyl]methyl]piperazine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1CCN(CC1)CC1=CC(=CC=C1)C(F)(F)F)O)C1=C(C=CC=C1OC)OC JHFWPXHWYILCHT-UHFFFAOYSA-N 0.000 claims 2
- SLJMIFFMIFPMMT-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-N-[2-(2-fluorophenyl)ethyl]-4-hydroxy-2-oxo-N-propyl-1H-pyridine-3-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N(CCC)CCC1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC SLJMIFFMIFPMMT-UHFFFAOYSA-N 0.000 claims 2
- BQIZDKBOPHTRFY-UHFFFAOYSA-N 6-butyl-5-(3-ethylphenyl)-4-hydroxy-3-[5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(N1)=O)C=1OC(=NN=1)CC=1N=C(SC=1)C)O)C1=CC(=CC=C1)CC BQIZDKBOPHTRFY-UHFFFAOYSA-N 0.000 claims 2
- QIGKOQAOJOZBKU-SFHVURJKSA-N 6-butyl-5-(3-fluoro-2,6-dimethoxyphenyl)-4-hydroxy-3-[(3R)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O)C1=C(C(=CC=C1OC)F)OC QIGKOQAOJOZBKU-SFHVURJKSA-N 0.000 claims 2
- HQNPYEHFAWFXRM-UHFFFAOYSA-N 6-butyl-N-[2-(4-chlorophenyl)ethyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-N-methyl-2-oxo-1H-pyridine-3-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N(C)CCC1=CC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC HQNPYEHFAWFXRM-UHFFFAOYSA-N 0.000 claims 2
- BPQHKPVDBBZUDZ-UHFFFAOYSA-N 6-butyl-N-[2-[(5-chloro-3-fluoropyridin-2-yl)amino]ethyl]-5-(2,6-dimethoxyphenyl)-4-hydroxy-N-methyl-2-oxo-1H-pyridine-3-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C(=O)N(C)CCNC1=NC=C(C=C1F)Cl)O)C1=C(C=CC=C1OC)OC BPQHKPVDBBZUDZ-UHFFFAOYSA-N 0.000 claims 2
- JDCLSEMPWVJGEQ-UHFFFAOYSA-N 6-cyclopentyl-5-(2,6-dimethoxyphenyl)-3-[3-(3-fluorophenyl)pyrrolidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound C1(CCCC1)C1=C(C(=C(C(=N1)O)C(=O)N1CC(CC1)C1=CC(=CC=C1)F)O)C1=C(C=CC=C1OC)OC JDCLSEMPWVJGEQ-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 206010049694 Left Ventricular Dysfunction Diseases 0.000 claims 2
- UWWMFNMBWWRCKQ-UHFFFAOYSA-N N-(2-benzamidoethyl)-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-N-methyl-2-oxo-1H-pyridine-3-carboxamide Chemical compound CCCCC1=C(C(O)=C(C(=O)N(C)CCNC(=O)C2=CC=CC=C2)C(O)=N1)C1=C(OC)C=CC=C1OC UWWMFNMBWWRCKQ-UHFFFAOYSA-N 0.000 claims 2
- SNHWZOWXLJFEGD-UHFFFAOYSA-N N-[1-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridine-3-carbonyl]azetidin-3-yl]-2,3-difluorobenzenesulfonamide Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CC(C2)NS(=O)(=O)C2=C(F)C(F)=CC=C2)C(O)=N1)C1=C(OC)C=CC=C1OC SNHWZOWXLJFEGD-UHFFFAOYSA-N 0.000 claims 2
- MVBNINGALJOTCH-UHFFFAOYSA-N N-[1-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridine-3-carbonyl]azetidin-3-yl]benzamide Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CC(C2)NC(=O)C2=CC=CC=C2)C(O)=N1)C1=C(OC)C=CC=C1OC MVBNINGALJOTCH-UHFFFAOYSA-N 0.000 claims 2
- VBXHAJWRRCOBEF-UHFFFAOYSA-N N-benzyl-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-N-propyl-1H-pyridine-3-carboxamide Chemical compound C(C1=CC=CC=C1)N(C(=O)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O)CCC VBXHAJWRRCOBEF-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 150000002009 diols Chemical class 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 230000002107 myocardial effect Effects 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- INOVPKZAEASFME-UHFFFAOYSA-N n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC=C1 INOVPKZAEASFME-UHFFFAOYSA-N 0.000 claims 2
- 238000007634 remodeling Methods 0.000 claims 2
- 125000004227 1,3-benzoxazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)OC2=C1[H] 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- FFVGBTZRGSIQAL-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-6-(4-fluorophenyl)-3-[3-(2-fluorophenyl)pyrrolidine-1-carbonyl]-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)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O FFVGBTZRGSIQAL-UHFFFAOYSA-N 0.000 claims 1
- MHXSGPZETNDQSO-KRWDZBQOSA-N 6-(ethoxymethyl)-5-(4-fluoro-2,6-dimethoxyphenyl)-4-hydroxy-3-[(3R)-3-phenylpyrrolidine-1-carbonyl]-1H-pyridin-2-one Chemical compound C(C)OCC1=C(C(=C(C(=N1)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O)C1=C(C=C(C=C1OC)F)OC MHXSGPZETNDQSO-KRWDZBQOSA-N 0.000 claims 1
- NIGQZZOSLVKRFR-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidine-1-carbonyl]-4-hydroxy-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(O)=N1)C1=C(OC)C=CC=C1OC NIGQZZOSLVKRFR-UHFFFAOYSA-N 0.000 claims 1
- VGCNPNDZOILGJM-UHFFFAOYSA-N 6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-3-(spiro[1H-2-benzofuran-3,4'-piperidine]-1'-carbonyl)-1H-pyridin-2-one Chemical compound CCCCC1=C(C(O)=C(C(=O)N2CCC3(CC2)OCC2=CC=CC=C32)C(O)=N1)C1=C(OC)C=CC=C1OC VGCNPNDZOILGJM-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 208000003037 Diastolic Heart Failure Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000008253 Systolic Heart Failure Diseases 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 238000007675 cardiac surgery Methods 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 208000018578 heart valve disease Diseases 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000002459 sustained effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562241367P | 2015-10-14 | 2015-10-14 | |
| US62/241,367 | 2015-10-14 | ||
| US201562270659P | 2015-12-22 | 2015-12-22 | |
| US62/270,659 | 2015-12-22 | ||
| PCT/US2016/056769 WO2017066402A1 (en) | 2015-10-14 | 2016-10-13 | 2,4-dihydroxy-nicotinamides as apj agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018530591A JP2018530591A (ja) | 2018-10-18 |
| JP2018530591A5 true JP2018530591A5 (OSRAM) | 2019-11-21 |
| JP6837482B2 JP6837482B2 (ja) | 2021-03-03 |
Family
ID=57178558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018519425A Active JP6837482B2 (ja) | 2015-10-14 | 2016-10-13 | Ａｐｊアゴニストとしての２，４−ジヒドロキシ−ニコチンアミド |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US10392347B2 (OSRAM) |
| EP (1) | EP3362442B1 (OSRAM) |
| JP (1) | JP6837482B2 (OSRAM) |
| KR (1) | KR102707502B1 (OSRAM) |
| CN (1) | CN108368087B (OSRAM) |
| AU (1) | AU2016340264B2 (OSRAM) |
| BR (1) | BR112018007395A2 (OSRAM) |
| CA (1) | CA3001974A1 (OSRAM) |
| CL (1) | CL2018000953A1 (OSRAM) |
| CO (1) | CO2018004968A2 (OSRAM) |
| EA (1) | EA034857B1 (OSRAM) |
| ES (1) | ES2774945T3 (OSRAM) |
| IL (1) | IL258577B (OSRAM) |
| MX (1) | MX376824B (OSRAM) |
| PE (1) | PE20181197A1 (OSRAM) |
| SG (1) | SG10201908839QA (OSRAM) |
| TW (1) | TW201720796A (OSRAM) |
| UY (1) | UY36949A (OSRAM) |
| WO (1) | WO2017066402A1 (OSRAM) |
| ZA (1) | ZA201802451B (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3300500B9 (en) | 2015-05-20 | 2021-01-13 | Amgen Inc. | Triazole agonists of the apj receptor |
| EA034912B1 (ru) | 2015-06-03 | 2020-04-06 | Бристол-Маерс Сквибб Компани | 4-гидрокси-3-(гетероарил)пиридин-2-оновые агонисты apj для применения в лечении сердечно-сосудистых заболеваний |
| US11390616B2 (en) | 2015-12-04 | 2022-07-19 | Bristol-Myers Squibb Company | Apelin receptor agonists and methods of use |
| TW201725203A (zh) | 2015-12-16 | 2017-07-16 | 必治妥美雅史谷比公司 | 作為ａｐｊ受體促效劑之雜芳基羥基嘧啶酮 |
| 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 |
| CN109641843B (zh) | 2016-06-14 | 2022-07-19 | 百时美施贵宝公司 | 作为apj激动剂的4-羟基-3-磺酰基吡啶-2(1h)-酮 |
| CN109311821B (zh) | 2016-06-14 | 2022-10-14 | 百时美施贵宝公司 | 作为apj激动剂的6-羟基-5-(苯基/杂芳基磺酰基)嘧啶-4(1h)-酮 |
| 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 |
| EP3541810B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
| WO2018097944A1 (en) | 2016-11-16 | 2018-05-31 | Amgen Inc. | Triazole furan 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 |
| EP3541802B1 (en) | 2016-11-16 | 2025-01-01 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| US10689367B2 (en) | 2016-11-16 | 2020-06-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the APJ receptor |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| US11149040B2 (en) | 2017-11-03 | 2021-10-19 | Amgen Inc. | Fused triazole agonists of the APJ receptor |
| WO2019213006A1 (en) | 2018-05-01 | 2019-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| WO2025153720A1 (en) * | 2024-01-19 | 2025-07-24 | Scenic Biotech Bv | Pla2g15 inhibitors |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH602664A5 (en) | 1973-06-14 | 1978-07-31 | Sandoz Ag | 2-Tert. amino-alkylamino-pyrimidine derivs. |
| ZA835878B (en) * | 1982-08-23 | 1985-03-27 | Warner Lambert Co | Cardiotonic agents |
| GB2263639A (en) | 1992-01-28 | 1993-08-04 | Merck & Co Inc | Substituted pyrimidinones as neurotensin antagonists |
| DE4425616A1 (de) * | 1994-07-20 | 1996-01-25 | Basf Ag | Hydroxypyridoncarbonsäureamide, deren Herstellung und Verwendung |
| BR9711098B1 (pt) | 1996-07-01 | 2011-10-04 | compostos heterocìclicos, processo para sua preparação e composições farmacêuticas contendo os mesmos e seu uso no tratamento de diabetes e doenças relacionadas. | |
| JP2004504302A (ja) | 2000-07-18 | 2004-02-12 | ニューロジェン・コーポレーション | ５−置換２−アリール−４−ピリミジノン |
| TW200300349A (en) | 2001-11-19 | 2003-06-01 | Sankyo Co | A 4-oxoqinoline derivative |
| US7166595B2 (en) | 2002-05-09 | 2007-01-23 | Cytokinetics, Inc. | Compounds, methods and compositions |
| AU2003231799A1 (en) | 2002-05-23 | 2003-12-12 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP2004339159A (ja) | 2003-05-16 | 2004-12-02 | Sankyo Co Ltd | ４−オキソキノリン誘導体を含有する医薬組成物 |
| WO2005026148A1 (en) | 2003-09-08 | 2005-03-24 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| EP1682534A2 (en) | 2003-11-03 | 2006-07-26 | Cytokinetics, Inc. | Pyrimidin-4-one compounds, compositions, and methods |
| WO2005060654A2 (en) | 2003-12-19 | 2005-07-07 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US7732613B2 (en) | 2005-09-14 | 2010-06-08 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| WO2007037543A1 (ja) | 2005-09-29 | 2007-04-05 | Banyu Pharmaceutical Co., Ltd. | ビアリールアミド誘導体 |
| JP5144532B2 (ja) | 2005-11-30 | 2013-02-13 | バーテックス ファーマシューティカルズ インコーポレイテッド | ｃ−Ｍｅｔ阻害剤及び用法 |
| US8367845B2 (en) | 2006-04-21 | 2013-02-05 | The Trustees Of Boston University | Ionic viscoelastics and viscoelastic salts |
| JP2007308441A (ja) * | 2006-05-22 | 2007-11-29 | Sumitomo Chemical Co Ltd | 含複素環化合物及びその用途 |
| WO2008052863A2 (de) | 2006-10-10 | 2008-05-08 | Proionic Production Of Ionic Substances Gmbh & Co Keg | Verfahren zur umsetzung von 1,3-hetero-aromatischen 2-carboxylaten mit wasser |
| WO2008052861A2 (de) | 2006-10-10 | 2008-05-08 | Proionic Production Of Ionic Substances Gmbh & Co Keg | Verfahren zur herstellung von 1,3 -hetero-aromatischen carbonaten |
| TW200845994A (en) | 2007-01-12 | 2008-12-01 | Smithkline Beecham Corp | N-substituted glycine derivatives: prolyl hydroxylase inhibitors |
| AU2008219166B2 (en) | 2007-02-16 | 2013-05-16 | Amgen Inc. | Nitrogen-containing heterocyclyl ketones and their use as c-Met inhibitors |
| CA2722308C (en) | 2008-04-15 | 2024-02-27 | Rfs Pharma, Llc. | Nucleoside derivatives for treatment of caliciviridae infections, including norovirus infections |
| WO2010072696A2 (de) | 2008-12-22 | 2010-07-01 | Basf Se | Mischungen hydrophober und hydrophiler ionischer flüssigkeiten und ihre verwendung in flüssigkeitsringverdichtern |
| US9040538B2 (en) | 2009-05-21 | 2015-05-26 | Universite Laval | Pyrimidines as novel therapeutic agents |
| 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 |
| KR20140039242A (ko) | 2011-05-31 | 2014-04-01 | 메르크 파텐트 게엠베하 | 전해질 제형 |
| BR112013030741A2 (pt) | 2011-05-31 | 2016-12-06 | Merck Patent Gmbh | compostos contendo ânions de hidreto- triciano-borato |
| 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 |
| WO2014004676A1 (en) | 2012-06-26 | 2014-01-03 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors as neuroprotective agents in the cns |
| DK2897939T3 (en) * | 2012-09-21 | 2017-05-08 | Sanofi Sa | BENZOIMIDAZOLCARBOXYL ACID AMIDE DERIVATIVES FOR THE TREATMENT OF METABOLIC OR CARDIOVASCULAR DISEASES |
| DE102012021452A1 (de) | 2012-10-31 | 2014-04-30 | Merck Patent Gmbh | Salze mit Trihydroperfluoralkoxybutansulfonat- oder Trihydroperfluoralkoxypropansulfonat-Anion |
| JP6410790B2 (ja) | 2013-03-14 | 2018-10-24 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | ミトコンドリアアルデヒドデヒドロゲナーゼ−２調節因子およびその使用方法 |
| CA2916653C (en) | 2013-06-27 | 2017-07-18 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
| WO2014207100A1 (en) | 2013-06-27 | 2014-12-31 | Basf Se | A process for coating paper with cellulose using a solution containing cellulose |
| KR102339016B1 (ko) | 2013-11-29 | 2021-12-14 | 프로이오닉 게엠베하 | 마이크로파 조사에 의한 접착제 경화 방법 |
| WO2015184011A2 (en) | 2014-05-28 | 2015-12-03 | Sanford-Burnham Medical Research Institute | Agonists of the apelin receptor and methods of use thereof |
| WO2015188073A1 (en) * | 2014-06-06 | 2015-12-10 | Research Triangle Institute | Apelin receptor (apj) agonists and uses thereof |
| WO2016074757A1 (de) | 2014-11-11 | 2016-05-19 | Merck Patent Gmbh | Verfahren zur herstellung von mono- und bis(perfluoralkyl)fluorophosphatsalzen und deren säuren |
| PL3287443T3 (pl) | 2015-04-24 | 2022-02-21 | Shionogi & Co., Ltd | 6-członowa pochodna heterocykliczna i kompozycja farmaceutyczna ją zawierająca |
| EP3300500B9 (en) | 2015-05-20 | 2021-01-13 | Amgen Inc. | Triazole agonists of the apj receptor |
| EA034912B1 (ru) | 2015-06-03 | 2020-04-06 | Бристол-Маерс Сквибб Компани | 4-гидрокси-3-(гетероарил)пиридин-2-оновые агонисты apj для применения в лечении сердечно-сосудистых заболеваний |
| KR101711744B1 (ko) | 2015-07-16 | 2017-03-02 | 경희대학교 산학협력단 | 옥사디아졸 유도체, 이의 제조방법 및 이를 포함하는 전자수송층 |
| US10626096B2 (en) | 2015-11-24 | 2020-04-21 | Sanford Burnham Prebys Medical Discovery Institute | Azole derivatives as apelin receptor agonist |
| US11390616B2 (en) | 2015-12-04 | 2022-07-19 | Bristol-Myers Squibb Company | Apelin receptor agonists and methods of use |
| TW201725203A (zh) | 2015-12-16 | 2017-07-16 | 必治妥美雅史谷比公司 | 作為ａｐｊ受體促效劑之雜芳基羥基嘧啶酮 |
| 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 |
| CN109641843B (zh) | 2016-06-14 | 2022-07-19 | 百时美施贵宝公司 | 作为apj激动剂的4-羟基-3-磺酰基吡啶-2(1h)-酮 |
| CN109311821B (zh) | 2016-06-14 | 2022-10-14 | 百时美施贵宝公司 | 作为apj激动剂的6-羟基-5-(苯基/杂芳基磺酰基)嘧啶-4(1h)-酮 |
| 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 |
-
2016
- 2016-10-13 KR KR1020187013119A patent/KR102707502B1/ko active Active
- 2016-10-13 EP EP16784732.6A patent/EP3362442B1/en active Active
- 2016-10-13 ES ES16784732T patent/ES2774945T3/es active Active
- 2016-10-13 AU AU2016340264A patent/AU2016340264B2/en not_active Ceased
- 2016-10-13 CN CN201680072835.5A patent/CN108368087B/zh active Active
- 2016-10-13 MX MX2018004344A patent/MX376824B/es active IP Right Grant
- 2016-10-13 JP JP2018519425A patent/JP6837482B2/ja active Active
- 2016-10-13 TW TW105133123A patent/TW201720796A/zh unknown
- 2016-10-13 PE PE2018000536A patent/PE20181197A1/es unknown
- 2016-10-13 UY UY0001036949A patent/UY36949A/es unknown
- 2016-10-13 BR BR112018007395A patent/BR112018007395A2/pt not_active IP Right Cessation
- 2016-10-13 US US15/767,364 patent/US10392347B2/en active Active
- 2016-10-13 SG SG10201908839Q patent/SG10201908839QA/en unknown
- 2016-10-13 CA CA3001974A patent/CA3001974A1/en not_active Abandoned
- 2016-10-13 WO PCT/US2016/056769 patent/WO2017066402A1/en not_active Ceased
- 2016-10-13 EA EA201890858A patent/EA034857B1/ru not_active IP Right Cessation
-
2018
- 2018-04-09 IL IL258577A patent/IL258577B/en active IP Right Grant
- 2018-04-13 ZA ZA2018/02451A patent/ZA201802451B/en unknown
- 2018-04-13 CL CL2018000953A patent/CL2018000953A1/es unknown
- 2018-05-10 CO CONC2018/0004968A patent/CO2018004968A2/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018530591A5 (OSRAM) | ||
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| RU2485114C2 (ru) | Карбоксамидные соединения и их применение в качестве ингибиторов кальпаинов | |
| JP2018535999A5 (OSRAM) | ||
| JP2018118992A5 (OSRAM) | ||
| JP2019509319A5 (OSRAM) | ||
| JP2020515575A5 (OSRAM) | ||
| JP2019537571A5 (OSRAM) | ||
| JP2017500364A5 (OSRAM) | ||
| RU2009121564A (ru) | Азаадамантановые производные и способы применения | |
| JP2011503166A5 (OSRAM) | ||
| JP2013545744A5 (OSRAM) | ||
| RU2017124425A (ru) | Производные 2,4-диоксо-хиназолин-6-сульфонамида в качестве ингибиторов parg | |
| JP2018524343A5 (OSRAM) | ||
| JP2019518036A5 (OSRAM) | ||
| RU2019132212A (ru) | Селективные ингибиторы hdac6 | |
| RU2008141761A (ru) | ИНГИБИТОРЫ с-МЕТ ПРОТЕИНКИНАЗЫ | |
| RU2008126398A (ru) | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpti) | |
| JP2015528022A5 (OSRAM) | ||
| JP2014062093A5 (OSRAM) | ||
| JP2016519096A5 (OSRAM) | ||
| RU2017125520A (ru) | Соединения, ингибирующие parg | |
| RU2014139601A (ru) | Ингибиторы серин/треониновых киназ | |
| RU2012116207A (ru) | Производные индола в качестве модуляторов crac | |
| JP2014510708A5 (OSRAM) |