EA037162B1 - 6-гидрокси-4-оксо-1,4-дигидропиримидин-5-карбоксамиды в качестве агонистов apj - Google Patents

Info

Publication number

EA037162B1

EA037162B1 EA201892123A EA201892123A EA037162B1 EA 037162 B1 EA037162 B1 EA 037162B1 EA 201892123 A EA201892123 A EA 201892123A EA 201892123 A EA201892123 A EA 201892123A EA 037162 B1 EA037162 B1 EA 037162B1

Authority

EA

Eurasian Patent Office

Prior art keywords

carbonyl

hydroxy

dihydropyrimidin

dimethoxyphenyl

pyrrolidine

Prior art date

2016-03-24

Links

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• 239000000556 agonist Substances 0.000 title abstract description 12
• RVVVQQNYGKCVMV-UHFFFAOYSA-N 4-hydroxy-6-oxo-1h-pyrimidine-5-carboxamide Chemical class NC(=O)C1=C(O)N=CNC1=O RVVVQQNYGKCVMV-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 184
• 239000000203 mixture Substances 0.000 claims abstract description 43
• -1 -O (CH2) 1_3OCH3 Chemical group 0.000 claims description 388
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 236
• KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 164
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 155
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 124
• 125000000217 alkyl group Chemical group 0.000 claims description 103
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 90
• 229910052801 chlorine Inorganic materials 0.000 claims description 85
• 229910052731 fluorine Inorganic materials 0.000 claims description 85
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 62
• 238000000034 method Methods 0.000 claims description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 57
• 229910052794 bromium Inorganic materials 0.000 claims description 47
• 229910052799 carbon Inorganic materials 0.000 claims description 47
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 229910052760 oxygen Inorganic materials 0.000 claims description 38
• 206010019280 Heart failures Diseases 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 238000011282 treatment Methods 0.000 claims description 36
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 28
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 26
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 239000003937 drug carrier Substances 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 14
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 10
• 208000029078 coronary artery disease Diseases 0.000 claims description 10
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 208000010125 myocardial infarction Diseases 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 7
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
• 208000006011 Stroke Diseases 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• OVTSAJGGBMKROF-YANBTOMASA-N 2-butyl-5-[3-(3-fluorophenyl)pyrrolidine-1-carbonyl]-6-hydroxy-3-[(1S)-1-phenylpropyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](CC)C1=CC=CC=C1)=O)C(=O)N1CC(CC1)C1=CC(=CC=C1)F)O OVTSAJGGBMKROF-YANBTOMASA-N 0.000 claims description 6
• KQIHNPUEKPNRRI-UHFFFAOYSA-N C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC Chemical compound C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC KQIHNPUEKPNRRI-UHFFFAOYSA-N 0.000 claims description 6
• UYALXHDMGGCLAX-UHFFFAOYSA-N C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=NC=C1)O)C1=C(C=CC=C1OC)OC Chemical compound C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=NC=C1)O)C1=C(C=CC=C1OC)OC UYALXHDMGGCLAX-UHFFFAOYSA-N 0.000 claims description 6
• BDLQPIGUKDQSBV-UHFFFAOYSA-N C1(CC1)CCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=NC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC Chemical compound C1(CC1)CCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=NC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC BDLQPIGUKDQSBV-UHFFFAOYSA-N 0.000 claims description 6
• CWBDSGSQIOIWAS-UHFFFAOYSA-N C1(CC1)CCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=NC=CC=C1F)O)C1=C(C=CC=C1OC)OC Chemical compound C1(CC1)CCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=NC=CC=C1F)O)C1=C(C=CC=C1OC)OC CWBDSGSQIOIWAS-UHFFFAOYSA-N 0.000 claims description 6
• XOAHEBDFWJSDLN-UHFFFAOYSA-N C1(CC1)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC Chemical compound C1(CC1)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC XOAHEBDFWJSDLN-UHFFFAOYSA-N 0.000 claims description 6
• DBZJTTWTZXIXEU-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)=O)COCC Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)=O)COCC DBZJTTWTZXIXEU-UHFFFAOYSA-N 0.000 claims description 6
• OFVBATVGQKJOLU-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=CC=C1)=O)COCC Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=CC=C1)=O)COCC OFVBATVGQKJOLU-UHFFFAOYSA-N 0.000 claims description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• GWOISGGMOJDLOR-AKRCKQFNSA-N 2-butyl-5-[3-(2-fluorophenyl)pyrrolidine-1-carbonyl]-6-hydroxy-3-[(1S)-1-phenylpropyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](CC)C1=CC=CC=C1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O GWOISGGMOJDLOR-AKRCKQFNSA-N 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• ATBDLSRTTBGEPS-UHFFFAOYSA-N C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=NC=CC=C1)O)C1=C(C=CC=C1OC)OC Chemical compound C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=NC=CC=C1)O)C1=C(C=CC=C1OC)OC ATBDLSRTTBGEPS-UHFFFAOYSA-N 0.000 claims description 5
• DZWWONYTHLSMAF-UHFFFAOYSA-N C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C=1C=NC=CC=1)O)C1=C(C=CC=C1OC)OC Chemical compound C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C=1C=NC=CC=1)O)C1=C(C=CC=C1OC)OC DZWWONYTHLSMAF-UHFFFAOYSA-N 0.000 claims description 5
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• YTEOJTOREOIWOW-FQEVSTJZSA-N 2-but-3-enyl-6-hydroxy-3-(2-methoxy-6-methylphenyl)-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CC=C)C1=NC(=C(C(N1C1=C(C=CC=C1C)OC)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O YTEOJTOREOIWOW-FQEVSTJZSA-N 0.000 claims description 4
• NQJTYSNXVAXUEU-ZYZRXSCRSA-N 2-butyl-5-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-6-hydroxy-3-[(1S)-1-phenylpropyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](CC)C1=CC=CC=C1)=O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)O NQJTYSNXVAXUEU-ZYZRXSCRSA-N 0.000 claims description 4
• IWDWCKWANCTNRN-ZYZRXSCRSA-N 2-butyl-5-[3-(5-chloro-3-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-6-hydroxy-3-[(1S)-1-phenylpropyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](CC)C1=CC=CC=C1)=O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)Cl)O IWDWCKWANCTNRN-ZYZRXSCRSA-N 0.000 claims description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• PUALTDQVGGYXCD-UHFFFAOYSA-N C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C#N)C=CC=C1)O)C1=C(C=CC=C1OC)OC Chemical compound C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C#N)C=CC=C1)O)C1=C(C=CC=C1OC)OC PUALTDQVGGYXCD-UHFFFAOYSA-N 0.000 claims description 4
• MHLWFUDLXMXXBP-UHFFFAOYSA-N C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC Chemical compound C(CCC)C=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC MHLWFUDLXMXXBP-UHFFFAOYSA-N 0.000 claims description 4
• WLVNHWHICLVJSF-UHFFFAOYSA-N C1(CC1)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC Chemical compound C1(CC1)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC WLVNHWHICLVJSF-UHFFFAOYSA-N 0.000 claims description 4
• BKCCKSROPMYQRA-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=C(C#N)C=CC=C1)=O)COCC Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=C(C#N)C=CC=C1)=O)COCC BKCCKSROPMYQRA-UHFFFAOYSA-N 0.000 claims description 4
• JYVZRPUTTMMSQK-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=CC(=CC=C1)F)=O)COCC Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=CC(=CC=C1)F)=O)COCC JYVZRPUTTMMSQK-UHFFFAOYSA-N 0.000 claims description 4
• OOPHWTDKOCYMNM-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=CC=C(C#N)C=C1)=O)COC(C)C Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=CC=C(C#N)C=C1)=O)COC(C)C OOPHWTDKOCYMNM-UHFFFAOYSA-N 0.000 claims description 4
• FYHZMIIVKFRVRF-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C=1C=NC=CC=1)=O)COCC Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C=1C=NC=CC=1)=O)COCC FYHZMIIVKFRVRF-UHFFFAOYSA-N 0.000 claims description 4
• NRWVKVRNEGKFTC-UHFFFAOYSA-N ClC=1C=C(C(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1CC)CC)C=1SC=C(N=1)C)=O)F Chemical compound ClC=1C=C(C(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1CC)CC)C=1SC=C(N=1)C)=O)F NRWVKVRNEGKFTC-UHFFFAOYSA-N 0.000 claims description 4
• DFQYXZSSMVLBSJ-UHFFFAOYSA-N ClC=1C=CC(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)CCC1CC1)=O Chemical compound ClC=1C=CC(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)CCC1CC1)=O DFQYXZSSMVLBSJ-UHFFFAOYSA-N 0.000 claims description 4
• YXKAFEVCHZPZFL-CEISFSOZSA-N ClC=1C=CC(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)[C@@H](CC)C1=CC(=CC(=C1)F)F)C=1C=NN(C=1)C)=O Chemical compound ClC=1C=CC(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)[C@@H](CC)C1=CC(=CC(=C1)F)F)C=1C=NN(C=1)C)=O YXKAFEVCHZPZFL-CEISFSOZSA-N 0.000 claims description 4
• YWQZEEMZOHTLDE-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O Chemical compound FC1=C(C=CC(=C1)F)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O YWQZEEMZOHTLDE-UHFFFAOYSA-N 0.000 claims description 4
• 125000003367 polycyclic group Chemical group 0.000 claims description 4
• 238000007634 remodeling Methods 0.000 claims description 4
• OVGUUSBHAPPKQU-UHFFFAOYSA-N 2-butyl-3-(2,6-diethylphenyl)-5-[3-(4-fluorophenyl)pyrrolidine-1-carbonyl]-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1CC)CC)=O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)O OVGUUSBHAPPKQU-UHFFFAOYSA-N 0.000 claims description 3
• GDXIQEVIBIVXGF-QHCPKHFHSA-N 2-butyl-3-(2,6-diethylphenyl)-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1CC)CC)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O GDXIQEVIBIVXGF-QHCPKHFHSA-N 0.000 claims description 3
• LLUVESSPUREZHP-UHFFFAOYSA-N 2-butyl-5-[3-(3-chlorophenyl)azetidine-1-carbonyl]-3-(2,6-dimethoxyphenyl)-6-hydroxypyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)C(=O)N1CC(C1)C1=CC(=CC=C1)Cl)O LLUVESSPUREZHP-UHFFFAOYSA-N 0.000 claims description 3
• SBJALXICERGMIS-ZYZRXSCRSA-N 2-butyl-5-[3-(5-chloro-3-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-6-hydroxy-3-[(1R)-2-methoxy-1-phenylethyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](COC)C1=CC=CC=C1)=O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)Cl)O SBJALXICERGMIS-ZYZRXSCRSA-N 0.000 claims description 3
• BTZZLEWEPNHEHR-GEPVFLLWSA-N 2-butyl-6-hydroxy-3-(2-methyl-1-phenylpropyl)-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C(C(C)C)C1=CC=CC=C1)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O BTZZLEWEPNHEHR-GEPVFLLWSA-N 0.000 claims description 3
• OPTCGNNKTWEHIE-GOTSBHOMSA-N 2-butyl-6-hydroxy-3-[(1S)-1-phenylpropyl]-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](CC)C1=CC=CC=C1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O OPTCGNNKTWEHIE-GOTSBHOMSA-N 0.000 claims description 3
• QYPVCSZUHUCCMH-BDPMCISCSA-N 2-butyl-6-hydroxy-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]-3-(1-pyridin-3-ylethyl)pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C(C)C=1C=NC=CC=1)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O QYPVCSZUHUCCMH-BDPMCISCSA-N 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
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• IFDAJTGDMJSTBG-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=C(C#N)C=CC=C1)=O)COC(C)C Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=C(C#N)C=CC=C1)=O)COC(C)C IFDAJTGDMJSTBG-UHFFFAOYSA-N 0.000 claims 2
• KMXXWKVCCAKXDY-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=C(C=CC=C1)C(F)(F)F)=O)COC(C)C Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=C(C=CC=C1)C(F)(F)F)=O)COC(C)C KMXXWKVCCAKXDY-UHFFFAOYSA-N 0.000 claims 2
• BFXUALMCVABIFZ-UHFFFAOYSA-N ClC=1C=C(C(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1CC)CC)C1=NN(C=C1)C)=O)F Chemical compound ClC=1C=C(C(=NC=1)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1CC)CC)C1=NN(C=C1)C)=O)F BFXUALMCVABIFZ-UHFFFAOYSA-N 0.000 claims 2
• OLFRBQZIFXWSAI-UHFFFAOYSA-N FC1=C(C(=CC=C1)F)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O Chemical compound FC1=C(C(=CC=C1)F)C1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O OLFRBQZIFXWSAI-UHFFFAOYSA-N 0.000 claims 2
• YTKDBAOFVPEASY-CEISFSOZSA-N FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1)F)=O)C1=NN(C=C1)C Chemical compound FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1)F)=O)C1=NN(C=C1)C YTKDBAOFVPEASY-CEISFSOZSA-N 0.000 claims 2
• SDCDGWXARNMVNN-CEISFSOZSA-N FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)=O)C1=NN(C=C1)CC Chemical compound FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)=O)C1=NN(C=C1)CC SDCDGWXARNMVNN-CEISFSOZSA-N 0.000 claims 2
• FRASOWUACCDYTP-FXMQYSIJSA-N FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=CC=C1F)=O)C1=NN(C=C1)C Chemical compound FC=1C=C(C=C(C=1)F)[C@H](CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=CC=C1F)=O)C1=NN(C=C1)C FRASOWUACCDYTP-FXMQYSIJSA-N 0.000 claims 2
• 230000002107 myocardial effect Effects 0.000 claims 2
• MFJBSCLACUMXCV-IBGZPJMESA-N 2-(cyclobutyloxymethyl)-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C1(CCC1)OCC1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O MFJBSCLACUMXCV-IBGZPJMESA-N 0.000 claims 1
• AVOKSOPYZNSZEI-IBGZPJMESA-N 2-(cyclopropylmethyl)-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C1(CC1)CC1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O AVOKSOPYZNSZEI-IBGZPJMESA-N 0.000 claims 1
• AVOKSOPYZNSZEI-LJQANCHMSA-N 2-(cyclopropylmethyl)-3-(2,6-dimethoxyphenyl)-6-hydroxy-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C1(CC1)CC1=NC(=C(C(N1C1=C(C=CC=C1OC)OC)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O AVOKSOPYZNSZEI-LJQANCHMSA-N 0.000 claims 1
• ZZDVWNBKRXZMTP-KRWDZBQOSA-N 2-butyl-3-(4,6-dimethoxypyrimidin-5-yl)-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C=1C(=NC=NC=1OC)OC)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O ZZDVWNBKRXZMTP-KRWDZBQOSA-N 0.000 claims 1
• UNIPHJZGDABKIO-RXVVDRJESA-N 2-butyl-3-[(1S)-1-(4-fluorophenyl)ethyl]-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](C)C1=CC=C(C=C1)F)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O UNIPHJZGDABKIO-RXVVDRJESA-N 0.000 claims 1
• LXVZLHUZAMFUCO-QFBILLFUSA-N 2-butyl-3-[(1S)-1-cyclopropylethyl]-6-hydroxy-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](C)C1CC1)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O LXVZLHUZAMFUCO-QFBILLFUSA-N 0.000 claims 1
• XZKLWCYQVWSPHV-YSYXNDDBSA-N 2-butyl-5-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-6-hydroxy-3-[(1S)-1-(3-methoxyphenyl)propyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](CC)C1=CC(=CC=C1)OC)=O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)O XZKLWCYQVWSPHV-YSYXNDDBSA-N 0.000 claims 1
• JFWKQRKFFSUZPV-KNQAVFIVSA-N 2-butyl-6-hydroxy-3-[(1R)-1-phenylethyl]-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@H](C)C1=CC=CC=C1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O JFWKQRKFFSUZPV-KNQAVFIVSA-N 0.000 claims 1
• OPTCGNNKTWEHIE-DHIUTWEWSA-N 2-butyl-6-hydroxy-3-[(1R)-1-phenylpropyl]-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@H](CC)C1=CC=CC=C1)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O OPTCGNNKTWEHIE-DHIUTWEWSA-N 0.000 claims 1
• JBMUARNSQGXMNO-GOTSBHOMSA-N 2-butyl-6-hydroxy-3-[(1R)-2-methoxy-1-phenylethyl]-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](COC)C1=CC=CC=C1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O JBMUARNSQGXMNO-GOTSBHOMSA-N 0.000 claims 1
• JBMUARNSQGXMNO-PKTZIBPZSA-N 2-butyl-6-hydroxy-3-[(1R)-2-methoxy-1-phenylethyl]-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](COC)C1=CC=CC=C1)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O JBMUARNSQGXMNO-PKTZIBPZSA-N 0.000 claims 1
• SJSFFCXZHPUWDH-FPOVZHCZSA-N 2-butyl-6-hydroxy-3-[(1S)-1-(2-methoxyphenyl)ethyl]-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](C)C1=C(C=CC=C1)OC)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O SJSFFCXZHPUWDH-FPOVZHCZSA-N 0.000 claims 1
• SJSFFCXZHPUWDH-PZJWPPBQSA-N 2-butyl-6-hydroxy-3-[(1S)-1-(2-methoxyphenyl)ethyl]-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](C)C1=C(C=CC=C1)OC)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O SJSFFCXZHPUWDH-PZJWPPBQSA-N 0.000 claims 1
• MPNYDTBILOXJOW-UGKGYDQZSA-N 2-butyl-6-hydroxy-3-[(1S)-1-(3-methoxyphenyl)ethyl]-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](C)C1=CC(=CC=C1)OC)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O MPNYDTBILOXJOW-UGKGYDQZSA-N 0.000 claims 1
• MPNYDTBILOXJOW-SIKLNZKXSA-N 2-butyl-6-hydroxy-3-[(1S)-1-(3-methoxyphenyl)ethyl]-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](C)C1=CC(=CC=C1)OC)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O MPNYDTBILOXJOW-SIKLNZKXSA-N 0.000 claims 1
• OAFNZMIDPBYGLZ-ZEQRLZLVSA-N 2-butyl-6-hydroxy-3-[(1S)-1-phenylbutyl]-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@@H](CCC)C1=CC=CC=C1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O OAFNZMIDPBYGLZ-ZEQRLZLVSA-N 0.000 claims 1
• JBMUARNSQGXMNO-XZOQPEGZSA-N 2-butyl-6-hydroxy-3-[(1S)-2-methoxy-1-phenylethyl]-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@H](COC)C1=CC=CC=C1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O JBMUARNSQGXMNO-XZOQPEGZSA-N 0.000 claims 1
• JBMUARNSQGXMNO-DHIUTWEWSA-N 2-butyl-6-hydroxy-3-[(1S)-2-methoxy-1-phenylethyl]-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1[C@H](COC)C1=CC=CC=C1)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)O JBMUARNSQGXMNO-DHIUTWEWSA-N 0.000 claims 1
• QYPVCSZUHUCCMH-ZYZRXSCRSA-N 2-butyl-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]-3-(1-pyridin-3-ylethyl)pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C(C)C=1C=NC=CC=1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O QYPVCSZUHUCCMH-ZYZRXSCRSA-N 0.000 claims 1
• NXINJULQQULGIQ-ZYZRXSCRSA-N 2-butyl-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]-3-(1-pyridin-4-ylethyl)pyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C(C)C1=CC=NC=C1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O NXINJULQQULGIQ-ZYZRXSCRSA-N 0.000 claims 1
• GZPLRKKFTSWWLM-KRWDZBQOSA-N 2-butyl-6-hydroxy-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]-3-propan-2-ylpyrimidin-4-one Chemical compound C(CCC)C1=NC(=C(C(N1C(C)C)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O GZPLRKKFTSWWLM-KRWDZBQOSA-N 0.000 claims 1
• UBRYGZKVZFHKJT-CVDCTZTESA-N 3-[(1S)-1-[2-butyl-4-hydroxy-6-oxo-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-1-yl]ethyl]benzonitrile Chemical compound C(CCC)C=1N(C(C(=C(N=1)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)=O)[C@@H](C)C=1C=C(C#N)C=CC=1 UBRYGZKVZFHKJT-CVDCTZTESA-N 0.000 claims 1
• BFXZLIVXBQLLHA-ZEQRLZLVSA-N 3-[(1S)-1-[2-butyl-4-hydroxy-6-oxo-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-1-yl]propyl]benzonitrile Chemical compound C(CCC)C=1N(C(C(=C(N=1)O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)=O)[C@@H](CC)C=1C=C(C#N)C=CC=1 BFXZLIVXBQLLHA-ZEQRLZLVSA-N 0.000 claims 1
• UBRYGZKVZFHKJT-WMZHIEFXSA-N 3-[(1S)-1-[2-butyl-4-hydroxy-6-oxo-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]pyrimidin-1-yl]ethyl]benzonitrile Chemical compound C(CCC)C=1N(C(C(=C(N=1)O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)=O)[C@@H](C)C=1C=C(C#N)C=CC=1 UBRYGZKVZFHKJT-WMZHIEFXSA-N 0.000 claims 1
• INPKGHONUSXLHG-BPARTEKVSA-N 3-[(1S)-1-[2-butyl-5-[3-(5-chloro-3-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-6-oxopyrimidin-1-yl]propyl]benzonitrile Chemical compound C(CCC)C=1N(C(C(=C(N=1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)Cl)=O)[C@@H](CC)C=1C=C(C#N)C=CC=1 INPKGHONUSXLHG-BPARTEKVSA-N 0.000 claims 1
• RFTYGENCWMDDIN-AKRCKQFNSA-N 3-[(1S)-1-[2-butyl-5-[3-(5-fluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-6-oxopyrimidin-1-yl]propyl]benzonitrile Chemical compound C(CCC)C=1N(C(C(=C(N=1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1)F)=O)[C@@H](CC)C=1C=C(C#N)C=CC=1 RFTYGENCWMDDIN-AKRCKQFNSA-N 0.000 claims 1
• QQFJGMNZUQQFEW-ZEQRLZLVSA-N 3-[(1S)-1-[4-hydroxy-6-oxo-5-[(3R)-3-phenylpyrrolidine-1-carbonyl]-2-(propan-2-yloxymethyl)pyrimidin-1-yl]propyl]benzonitrile Chemical compound OC=1N=C(N(C(C=1C(=O)N1C[C@H](CC1)C1=CC=CC=C1)=O)[C@@H](CC)C=1C=C(C#N)C=CC=1)COC(C)C QQFJGMNZUQQFEW-ZEQRLZLVSA-N 0.000 claims 1
• DBFWYSZWFRMJCO-GHZUAHJPSA-N 3-[(S)-[2-butyl-5-[3-(3,5-difluoropyridin-2-yl)pyrrolidine-1-carbonyl]-4-hydroxy-6-oxopyrimidin-1-yl]-cyclopropylmethyl]benzonitrile Chemical compound C(CCC)C=1N(C(C(=C(N=1)O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)=O)[C@H](C=1C=C(C#N)C=CC=1)C1CC1 DBFWYSZWFRMJCO-GHZUAHJPSA-N 0.000 claims 1
• JMRVEVDLWJYYSN-YADHBBJMSA-N 6-hydroxy-3-[(1R)-2-methoxy-1-phenylethyl]-5-[(3S)-3-phenylpyrrolidine-1-carbonyl]-2-propylpyrimidin-4-one Chemical compound OC1=C(C(N(C(=N1)CCC)[C@@H](COC)C1=CC=CC=C1)=O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1 JMRVEVDLWJYYSN-YADHBBJMSA-N 0.000 claims 1
• KJZKRYJVMIRYDN-UHFFFAOYSA-N C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC Chemical compound C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC KJZKRYJVMIRYDN-UHFFFAOYSA-N 0.000 claims 1
• UKLITGJJJKCNSY-UHFFFAOYSA-N C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC Chemical compound C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=C(C=CC=C1)F)O)C1=C(C=CC=C1OC)OC UKLITGJJJKCNSY-UHFFFAOYSA-N 0.000 claims 1
• PQLKHUNPNPCJBW-UHFFFAOYSA-N C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC Chemical compound C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1CC(CC1)C1=CC=C(C=C1)F)O)C1=C(C=CC=C1OC)OC PQLKHUNPNPCJBW-UHFFFAOYSA-N 0.000 claims 1
• CNCRLSNNLWARSD-IBGZPJMESA-N C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC Chemical compound C(C)(C)(C)OCC=1N(C(=C(C(N=1)=O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)O)C1=C(C=CC=C1OC)OC CNCRLSNNLWARSD-IBGZPJMESA-N 0.000 claims 1
• BSPLYSIFAXULPE-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)=O)C=1N=C(SC=1)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)=O)C=1N=C(SC=1)C BSPLYSIFAXULPE-UHFFFAOYSA-N 0.000 claims 1
• WOXQKXJSKOSTQG-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)=O)C=1N=C(SC=1)C(C)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1CC(CC1)C1=NC=C(C=C1F)F)=O)C=1N=C(SC=1)C(C)C WOXQKXJSKOSTQG-UHFFFAOYSA-N 0.000 claims 1
• CGRQPAGRUVAZHS-XMMPIXPASA-N C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)=O)C1=NN(C=C1)C(C)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)=O)C1=NN(C=C1)C(C)C CGRQPAGRUVAZHS-XMMPIXPASA-N 0.000 claims 1
• VLGPQFGIQORLQX-JOCHJYFZSA-N C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)=O)C=1N=C(SC=1)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1C[C@@H](CC1)C1=CC=CC=C1)=O)C=1N=C(SC=1)C VLGPQFGIQORLQX-JOCHJYFZSA-N 0.000 claims 1
• VLGPQFGIQORLQX-QFIPXVFZSA-N C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)=O)C=1N=C(SC=1)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1C(=NC(C(=C1O)C(=O)N1C[C@H](CC1)C1=CC=CC=C1)=O)C=1N=C(SC=1)C VLGPQFGIQORLQX-QFIPXVFZSA-N 0.000 claims 1
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• QDFRVKBPUJQSAM-IBGZPJMESA-N C(C1=CC=CC=C1)O[C@@H]1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O Chemical compound C(C1=CC=CC=C1)O[C@@H]1CN(CC1)C(=O)C=1C(N=C(N(C=1O)C1=C(C=CC=C1OC)OC)COCC)=O QDFRVKBPUJQSAM-IBGZPJMESA-N 0.000 claims 1
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