JP2018530591A5 - - Google Patents
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- 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
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- 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
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| EP3468956B1 (en) | 2016-06-14 | 2021-03-03 | Bristol-Myers Squibb Company | 6-hydroxy-5-(phenyl/heteroarylsulfonyl)pyrimidin-4(1h)-ones as apj agonists |
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-
2016
- 2016-10-13 TW TW105133123A patent/TW201720796A/zh unknown
- 2016-10-13 KR KR1020187013119A patent/KR102707502B1/ko active Active
- 2016-10-13 CA CA3001974A patent/CA3001974A1/en not_active Abandoned
- 2016-10-13 ES ES16784732T patent/ES2774945T3/es active Active
- 2016-10-13 BR BR112018007395A patent/BR112018007395A2/pt not_active IP Right Cessation
- 2016-10-13 PE PE2018000536A patent/PE20181197A1/es unknown
- 2016-10-13 SG SG10201908839Q patent/SG10201908839QA/en unknown
- 2016-10-13 EP EP16784732.6A patent/EP3362442B1/en active Active
- 2016-10-13 EA EA201890858A patent/EA034857B1/ru not_active IP Right Cessation
- 2016-10-13 AU AU2016340264A patent/AU2016340264B2/en not_active Ceased
- 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 UY UY0001036949A patent/UY36949A/es unknown
- 2016-10-13 WO PCT/US2016/056769 patent/WO2017066402A1/en not_active Ceased
- 2016-10-13 US US15/767,364 patent/US10392347B2/en active Active
- 2016-10-13 CN CN201680072835.5A patent/CN108368087B/zh active Active
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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
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