ES2446416T3 - Compuestos basados en quinolona que presentan actividad inhibidora de prolil hidroxilasa, composiciones y usos de los mismos - Google Patents

Info

Publication number

ES2446416T3

ES2446416T3 ES06844992.5T ES06844992T ES2446416T3 ES 2446416 T3 ES2446416 T3 ES 2446416T3 ES 06844992 T ES06844992 T ES 06844992T ES 2446416 T3 ES2446416 T3 ES 2446416T3

Authority

ES

Spain

Prior art keywords

methyl

dihydroquinolin

hydroxy

oxo

carboxamido

Prior art date

2005-12-09

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 89
• 230000002401 inhibitory effect Effects 0.000 title claims description 7
• 239000000203 mixture Substances 0.000 title description 51
• 102000004079 Prolyl Hydroxylases Human genes 0.000 title description 17
• 108010043005 Prolyl Hydroxylases Proteins 0.000 title description 17
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title description 5
• -1 methoxy, ethoxy, propoxy, butoxy Chemical group 0.000 claims abstract description 67
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
• 150000003839 salts Chemical class 0.000 claims abstract description 11
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
• 239000012453 solvate Substances 0.000 claims abstract description 8
• 150000002367 halogens Chemical class 0.000 claims abstract description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 6
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 6
• 125000001544 thienyl group Chemical class 0.000 claims abstract description 6
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims abstract description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 3
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
• 125000005843 halogen group Chemical group 0.000 claims abstract description 3
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 3
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
• 125000001424 substituent group Chemical group 0.000 claims abstract description 3
• 150000003557 thiazoles Chemical class 0.000 claims abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 68
• 239000002253 acid Substances 0.000 claims description 62
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
• 125000005518 carboxamido group Chemical group 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
• 201000010099 disease Diseases 0.000 claims description 27
• 208000035475 disorder Diseases 0.000 claims description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 230000033444 hydroxylation Effects 0.000 claims description 8
• 238000005805 hydroxylation reaction Methods 0.000 claims description 8
• 208000028867 ischemia Diseases 0.000 claims description 8
• 206010021143 Hypoxia Diseases 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• 208000007502 anemia Diseases 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 208000002903 Thalassemia Diseases 0.000 claims description 5
• 208000037849 arterial hypertension Diseases 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 230000009885 systemic effect Effects 0.000 claims description 5
• 230000029663 wound healing Effects 0.000 claims description 5
• 238000002689 xenotransplantation Methods 0.000 claims description 5
• 230000007954 hypoxia Effects 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• 108091005880 Hemoglobin F Proteins 0.000 claims description 3
• 230000033115 angiogenesis Effects 0.000 claims description 3
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• RQBZCUYDLKPTLI-ZETCQYMHSA-N (2s)-2-[(4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound CN1C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1C=CC=C2OC RQBZCUYDLKPTLI-ZETCQYMHSA-N 0.000 claims description 2
• PDSBXCAGPDHXJW-ZETCQYMHSA-N (2s)-2-[(4-hydroxy-6-methoxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound CN1C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=CC(OC)=CC=C21 PDSBXCAGPDHXJW-ZETCQYMHSA-N 0.000 claims description 2
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• VXTIXHBJPXETFK-LURJTMIESA-N (2s)-2-[(5-fluoro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1F VXTIXHBJPXETFK-LURJTMIESA-N 0.000 claims description 2
• GFAXJGZPBAPTEP-LURJTMIESA-N (2s)-2-[(7-bromo-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=C(Br)C=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 GFAXJGZPBAPTEP-LURJTMIESA-N 0.000 claims description 2
• ISDXBEXXVXZCTD-LURJTMIESA-N (2s)-2-[(7-fluoro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=C(F)C=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 ISDXBEXXVXZCTD-LURJTMIESA-N 0.000 claims description 2
• GJARJBFKTNAVOM-UHFFFAOYSA-N 2-[(1-ethyl-4-hydroxy-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(CC)C2=C1 GJARJBFKTNAVOM-UHFFFAOYSA-N 0.000 claims description 2
• BKTGJRHYWQCAAF-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-quinolin-5-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(C3=CC=C4N(C(C(C(=O)NCC(O)=O)=C(O)C4=C3)=O)C)=CC=CC2=N1 BKTGJRHYWQCAAF-UHFFFAOYSA-N 0.000 claims description 2
• ZXEBQZLMZHGLKH-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-7-piperidin-1-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1N1CCCCC1 ZXEBQZLMZHGLKH-UHFFFAOYSA-N 0.000 claims description 2
• CJNOOVPHDXMSKW-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-6-naphthalen-1-yl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(C3=CC=C4N(C(C(C(=O)NCC(O)=O)=C(O)C4=C3)=O)C)=CC=CC2=C1 CJNOOVPHDXMSKW-UHFFFAOYSA-N 0.000 claims description 2
• IRBZJXLHUVEVRV-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-6-naphthalen-2-yl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=CC2=CC(C3=CC=C4N(C(C(C(=O)NCC(O)=O)=C(O)C4=C3)=O)C)=CC=C21 IRBZJXLHUVEVRV-UHFFFAOYSA-N 0.000 claims description 2
• WIDLPHCZZIYDLI-UHFFFAOYSA-N 2-[(4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C2=C1C=CC=C2OC WIDLPHCZZIYDLI-UHFFFAOYSA-N 0.000 claims description 2
• LNNUHMLJMSPTKU-UHFFFAOYSA-N 2-[(4-hydroxy-6-methoxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C2=CC(OC)=CC=C21 LNNUHMLJMSPTKU-UHFFFAOYSA-N 0.000 claims description 2
• XDZPUSDZXBWOFY-UHFFFAOYSA-N 2-[(4-hydroxy-8-methoxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1C=CC=C2OC XDZPUSDZXBWOFY-UHFFFAOYSA-N 0.000 claims description 2
• DPJVIFGBDKAJDQ-UHFFFAOYSA-N 2-[(5-chloro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC(Cl)=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 DPJVIFGBDKAJDQ-UHFFFAOYSA-N 0.000 claims description 2
• HRDFJJPDFDMWEY-UHFFFAOYSA-N 2-[(5-fluoro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC(F)=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 HRDFJJPDFDMWEY-UHFFFAOYSA-N 0.000 claims description 2
• GMRWBXRYKVSCBX-UHFFFAOYSA-N 2-[(6-bromo-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(Br)C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 GMRWBXRYKVSCBX-UHFFFAOYSA-N 0.000 claims description 2
• YNLOPXZRGDOVFA-UHFFFAOYSA-N 2-[(6-cyano-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(C#N)C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 YNLOPXZRGDOVFA-UHFFFAOYSA-N 0.000 claims description 2
• TVDMHSMWQLPNKU-UHFFFAOYSA-N 2-[(7-ethyl-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC(CC)=CC=C21 TVDMHSMWQLPNKU-UHFFFAOYSA-N 0.000 claims description 2
• KDTRRLPFOLSPLL-UHFFFAOYSA-N 2-[(7-ethynyl-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C#CC1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 KDTRRLPFOLSPLL-UHFFFAOYSA-N 0.000 claims description 2
• XOANHYHRCYFHML-UHFFFAOYSA-N 2-[(7-fluoro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound FC1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 XOANHYHRCYFHML-UHFFFAOYSA-N 0.000 claims description 2
• RVQVBSPIIGFLSV-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-2-oxo-6-(3-propan-2-ylphenyl)quinoline-3-carbonyl]amino]acetic acid Chemical compound CC(C)C1=CC=CC(C=2C=C3C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C3=CC=2)=C1 RVQVBSPIIGFLSV-UHFFFAOYSA-N 0.000 claims description 2
• BEIVZPXLBHRSPK-UHFFFAOYSA-N 2-[[4-hydroxy-6-(1h-indol-5-yl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2NC=CC2=CC(C2=CC=C3N(C(C(C(=O)NCC(O)=O)=C(O)C3=C2)=O)C)=C1 BEIVZPXLBHRSPK-UHFFFAOYSA-N 0.000 claims description 2
• QQRAQHVFIBXTJX-UHFFFAOYSA-N 2-[[4-hydroxy-6-(2-methoxyphenyl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC=C1C1=CC=C(N(C)C(=O)C(C(=O)NCC(O)=O)=C2O)C2=C1 QQRAQHVFIBXTJX-UHFFFAOYSA-N 0.000 claims description 2
• SDFOIOCUHPEWPX-UHFFFAOYSA-N 2-[[4-hydroxy-6-(3-hydroxyphenyl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC(O)=C1 SDFOIOCUHPEWPX-UHFFFAOYSA-N 0.000 claims description 2
• MBYNMHVPDBIWLW-UHFFFAOYSA-N 2-[[4-hydroxy-6-(3-methoxyphenyl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC(C=2C=C3C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C3=CC=2)=C1 MBYNMHVPDBIWLW-UHFFFAOYSA-N 0.000 claims description 2
• VWLAGDXVNAQMTK-UHFFFAOYSA-N 2-[[4-hydroxy-6-(4-methoxyphenyl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C)C(=O)C(C(=O)NCC(O)=O)=C2O)C2=C1 VWLAGDXVNAQMTK-UHFFFAOYSA-N 0.000 claims description 2
• AZEYCUJNIMJHAQ-UHFFFAOYSA-N 2-[[4-hydroxy-7-(3-methoxyphenyl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC(C=2C=C3N(C)C(=O)C(C(=O)NCC(O)=O)=C(O)C3=CC=2)=C1 AZEYCUJNIMJHAQ-UHFFFAOYSA-N 0.000 claims description 2
• SDGJRLZWULLZMN-UHFFFAOYSA-N 2-[[4-hydroxy-7-(4-methoxyphenyl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(O)=C(C(=O)NCC(O)=O)C(=O)N2C)C2=C1 SDGJRLZWULLZMN-UHFFFAOYSA-N 0.000 claims description 2
• ZVQCQWFLCBLVOJ-UHFFFAOYSA-N 2-[[6-(3-chlorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC(Cl)=C1 ZVQCQWFLCBLVOJ-UHFFFAOYSA-N 0.000 claims description 2
• SRCSZNBJRWKWDX-UHFFFAOYSA-N 2-[[7-(3-chlorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CC(Cl)=C1 SRCSZNBJRWKWDX-UHFFFAOYSA-N 0.000 claims description 2
• IKKFMIIGCCGGDU-UHFFFAOYSA-N 2-[[7-(3-cyanophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CC(C#N)=C1 IKKFMIIGCCGGDU-UHFFFAOYSA-N 0.000 claims description 2
• HDEFCEUMWRQXMC-UHFFFAOYSA-N 2-[[7-(4-chlorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=C(Cl)C=C1 HDEFCEUMWRQXMC-UHFFFAOYSA-N 0.000 claims description 2
• 238000011316 allogeneic transplantation Methods 0.000 claims description 2
• DIPSWLHNGLUACG-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(N)=O)C(=O)N(C)C2=C1 DIPSWLHNGLUACG-UHFFFAOYSA-N 0.000 claims description 2
• WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 2
• 238000002054 transplantation Methods 0.000 claims 7
• HJRSTWRGACBMNH-LURJTMIESA-N (2s)-2-[[4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)quinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=C(C(F)(F)F)C=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 HJRSTWRGACBMNH-LURJTMIESA-N 0.000 claims 2
• YYZUXHYOMIAURD-GFCCVEGCSA-N (2r)-2-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@H](C(C)C)C(O)=O)=C(O)C2=C1 YYZUXHYOMIAURD-GFCCVEGCSA-N 0.000 claims 1
• DHRMXCZYTHDBIP-SSDOTTSWSA-N (2r)-2-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@H](C)C(O)=O)=C(O)C2=C1 DHRMXCZYTHDBIP-SSDOTTSWSA-N 0.000 claims 1
• HWYYYJVHNKRVCP-QMMMGPOBSA-N (2s)-2-[(4-hydroxy-1,5-dimethyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1C HWYYYJVHNKRVCP-QMMMGPOBSA-N 0.000 claims 1
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• QQYJVAIJQSEXRU-QMMMGPOBSA-N (2s)-2-[(4-hydroxy-1,7-dimethyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=C(C)C=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 QQYJVAIJQSEXRU-QMMMGPOBSA-N 0.000 claims 1
• NHXTVFKTKSKDRE-QMMMGPOBSA-N (2s)-2-[(4-hydroxy-1,8-dimethyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC(C)=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 NHXTVFKTKSKDRE-QMMMGPOBSA-N 0.000 claims 1
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• YYZUXHYOMIAURD-LBPRGKRZSA-N (2s)-2-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]-3-methylbutanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C(C)C)C(O)=O)=C(O)C2=C1 YYZUXHYOMIAURD-LBPRGKRZSA-N 0.000 claims 1
• GNDOMVYVGPMTKV-VIFPVBQESA-N (2s)-2-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]butanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](CC)C(O)=O)=C(O)C2=C1 GNDOMVYVGPMTKV-VIFPVBQESA-N 0.000 claims 1
• DHRMXCZYTHDBIP-ZETCQYMHSA-N (2s)-2-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 DHRMXCZYTHDBIP-ZETCQYMHSA-N 0.000 claims 1
• IVUOWPDHABXFMB-LURJTMIESA-N (2s)-2-[(4-hydroxy-6-iodo-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound IC1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 IVUOWPDHABXFMB-LURJTMIESA-N 0.000 claims 1
• LWQLUUAZKKESRI-LURJTMIESA-N (2s)-2-[(6-bromo-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound BrC1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 LWQLUUAZKKESRI-LURJTMIESA-N 0.000 claims 1
• FBJAIKDPOGBTPU-LURJTMIESA-N (2s)-2-[(6-fluoro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]propanoic acid Chemical compound FC1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1 FBJAIKDPOGBTPU-LURJTMIESA-N 0.000 claims 1
• BGRDLIKDCZYUEO-LURJTMIESA-N (2s)-2-[[4-hydroxy-1-methyl-2-oxo-5-(trifluoromethyl)quinoline-3-carbonyl]amino]propanoic acid Chemical compound C1=CC=C2N(C)C(=O)C(C(=O)N[C@@H](C)C(O)=O)=C(O)C2=C1C(F)(F)F BGRDLIKDCZYUEO-LURJTMIESA-N 0.000 claims 1
• PNDLNSZTPRSEOJ-UHFFFAOYSA-N 2-[(4-hydroxy-1,5-dimethyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C2=C1C=CC=C2C PNDLNSZTPRSEOJ-UHFFFAOYSA-N 0.000 claims 1
• LOMMFBDBEIBPER-UHFFFAOYSA-N 2-[(4-hydroxy-1,6-dimethyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C2=CC(C)=CC=C21 LOMMFBDBEIBPER-UHFFFAOYSA-N 0.000 claims 1
• OIDAJIOHKIGKKC-UHFFFAOYSA-N 2-[(4-hydroxy-1,7-dimethyl-2-oxo-6-phenylquinoline-3-carbonyl)amino]acetic acid Chemical compound CC1=CC=2N(C)C(=O)C(C(=O)NCC(O)=O)=C(O)C=2C=C1C1=CC=CC=C1 OIDAJIOHKIGKKC-UHFFFAOYSA-N 0.000 claims 1
• BDXVRSYBYNXEAK-UHFFFAOYSA-N 2-[(4-hydroxy-1,7-dimethyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC(C)=CC=C21 BDXVRSYBYNXEAK-UHFFFAOYSA-N 0.000 claims 1
• JTKWPGHFKHVGHP-UHFFFAOYSA-N 2-[(4-hydroxy-1,8-dimethyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1C=CC=C2C JTKWPGHFKHVGHP-UHFFFAOYSA-N 0.000 claims 1
• QWJDZLMCFCZUAH-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-phenylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1 QWJDZLMCFCZUAH-UHFFFAOYSA-N 0.000 claims 1
• UAYVCEKLKCHCBI-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-piperidin-1-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1N1CCCCC1 UAYVCEKLKCHCBI-UHFFFAOYSA-N 0.000 claims 1
• IDFUVRPDGRDPCU-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-pyridin-2-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=N1 IDFUVRPDGRDPCU-UHFFFAOYSA-N 0.000 claims 1
• ODZRGPDHXJIJLC-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-pyridin-3-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CN=C1 ODZRGPDHXJIJLC-UHFFFAOYSA-N 0.000 claims 1
• RMKIREXGAHDSMJ-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-pyridin-4-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=NC=C1 RMKIREXGAHDSMJ-UHFFFAOYSA-N 0.000 claims 1
• UBKHZSZEYCFPPJ-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-pyrimidin-2-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=NC=CC=N1 UBKHZSZEYCFPPJ-UHFFFAOYSA-N 0.000 claims 1
• NMCWQJKAAVEEND-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-6-thiophen-2-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CS1 NMCWQJKAAVEEND-UHFFFAOYSA-N 0.000 claims 1
• AQMAUVGFMSXBIA-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-7-phenylquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CC=C1 AQMAUVGFMSXBIA-UHFFFAOYSA-N 0.000 claims 1
• CIEYHXMRPLAFGQ-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-7-thiophen-2-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CS1 CIEYHXMRPLAFGQ-UHFFFAOYSA-N 0.000 claims 1
• IOVWVVJXNYAZHE-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxo-7-thiophen-3-ylquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C=1C=CSC=1 IOVWVVJXNYAZHE-UHFFFAOYSA-N 0.000 claims 1
• IREGYLCBLKVNQE-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]-2-methylpropanoic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NC(C)(C)C(O)=O)C(=O)N(C)C2=C1 IREGYLCBLKVNQE-UHFFFAOYSA-N 0.000 claims 1
• UMQOTZCXVAMZNY-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 UMQOTZCXVAMZNY-UHFFFAOYSA-N 0.000 claims 1
• BLFWXXSWDRFNQD-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-6-morpholin-4-yl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1N1CCOCC1 BLFWXXSWDRFNQD-UHFFFAOYSA-N 0.000 claims 1
• XRABXEQPBLOUCZ-UHFFFAOYSA-N 2-[(4-hydroxy-1-methyl-7-nitro-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound [O-][N+](=O)C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 XRABXEQPBLOUCZ-UHFFFAOYSA-N 0.000 claims 1
• YSQFBTLKRBQMFS-UHFFFAOYSA-N 2-[(4-hydroxy-6-iodo-1,7-dimethyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound CN1C(=O)C(C(=O)NCC(O)=O)=C(O)C2=C1C=C(C)C(I)=C2 YSQFBTLKRBQMFS-UHFFFAOYSA-N 0.000 claims 1
• UIZQPFBGDWCNSA-UHFFFAOYSA-N 2-[(4-hydroxy-6-iodo-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(I)C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 UIZQPFBGDWCNSA-UHFFFAOYSA-N 0.000 claims 1
• MSLMWNFYCYYSDQ-UHFFFAOYSA-N 2-[(6-chloro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(Cl)C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 MSLMWNFYCYYSDQ-UHFFFAOYSA-N 0.000 claims 1
• CNIHRYJVPKDRNB-UHFFFAOYSA-N 2-[(6-fluoro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(F)C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 CNIHRYJVPKDRNB-UHFFFAOYSA-N 0.000 claims 1
• HGAGTLBOGDXJGA-UHFFFAOYSA-N 2-[(7-bromo-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound BrC1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 HGAGTLBOGDXJGA-UHFFFAOYSA-N 0.000 claims 1
• GQOBYAODONUIGR-UHFFFAOYSA-N 2-[(7-chloro-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound ClC1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 GQOBYAODONUIGR-UHFFFAOYSA-N 0.000 claims 1
• ZQIWQINXKHEJDK-UHFFFAOYSA-N 2-[(7-cyano-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound N#CC1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 ZQIWQINXKHEJDK-UHFFFAOYSA-N 0.000 claims 1
• ROORRYYCMXQXFU-HQVZTVAUSA-N 2-[[(3s)-3,4-dihydroxy-1-methyl-2-oxo-4h-quinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC=C2N(C)C(=O)[C@@](O)(C(=O)NCC(O)=O)C(O)C2=C1 ROORRYYCMXQXFU-HQVZTVAUSA-N 0.000 claims 1
• LEJVQFYNLWFGEW-UHFFFAOYSA-N 2-[[4-hydroxy-1,7-dimethyl-6-(2-methylpyridin-3-yl)-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CC=2N(C)C(=O)C(C(=O)NCC(O)=O)=C(O)C=2C=C1C1=CC=CN=C1C LEJVQFYNLWFGEW-UHFFFAOYSA-N 0.000 claims 1
• ACPDGXXICBKLAU-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-2-oxo-5-(trifluoromethyl)quinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(C(F)(F)F)=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 ACPDGXXICBKLAU-UHFFFAOYSA-N 0.000 claims 1
• FNDGTZCZXKTKFW-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-2-oxo-6-(4-phenoxyphenyl)quinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 FNDGTZCZXKTKFW-UHFFFAOYSA-N 0.000 claims 1
• OQIVEXVBRAKKFL-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-2-oxo-7-(1h-pyrazol-4-yl)quinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C=1C=NNC=1 OQIVEXVBRAKKFL-UHFFFAOYSA-N 0.000 claims 1
• INBJVINUXPKYEX-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)quinoline-3-carbonyl]amino]acetic acid Chemical compound FC(F)(F)C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=C1 INBJVINUXPKYEX-UHFFFAOYSA-N 0.000 claims 1
• MRJKHROJRDQJAT-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-6-(2-methylpyridin-3-yl)-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=NC=CC=C1C1=CC=C(N(C)C(=O)C(C(=O)NCC(O)=O)=C2O)C2=C1 MRJKHROJRDQJAT-UHFFFAOYSA-N 0.000 claims 1
• XXNCNRUMPIAIDB-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-6-(3-methylthiophen-2-yl)-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CSC(C=2C=C3C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C3=CC=2)=C1C XXNCNRUMPIAIDB-UHFFFAOYSA-N 0.000 claims 1
• DRONGOLLFNMGEL-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-6-(6-methylpyridazin-3-yl)-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound N1=NC(C)=CC=C1C1=CC=C(N(C)C(=O)C(C(=O)NCC(O)=O)=C2O)C2=C1 DRONGOLLFNMGEL-UHFFFAOYSA-N 0.000 claims 1
• ODXYDUCLSFKDJF-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-7-(2-methylphenyl)-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=C(C(=O)NCC(O)=O)C(=O)N2C)C2=C1 ODXYDUCLSFKDJF-UHFFFAOYSA-N 0.000 claims 1
• JZZCVHSPQVDAIL-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-7-(3-methylthiophen-2-yl)-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CSC(C=2C=C3N(C)C(=O)C(C(=O)NCC(O)=O)=C(O)C3=CC=2)=C1C JZZCVHSPQVDAIL-UHFFFAOYSA-N 0.000 claims 1
• NJJNQUZQGGHGCI-UHFFFAOYSA-N 2-[[4-hydroxy-1-methyl-7-(4-methylphenyl)-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(O)=C(C(=O)NCC(O)=O)C(=O)N2C)C2=C1 NJJNQUZQGGHGCI-UHFFFAOYSA-N 0.000 claims 1
• BXEYEZLAUQJRBN-UHFFFAOYSA-N 2-[[4-hydroxy-7-(2-methoxyphenyl)-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(O)=C(C(=O)NCC(O)=O)C(=O)N2C)C2=C1 BXEYEZLAUQJRBN-UHFFFAOYSA-N 0.000 claims 1
• PVAUXUZCDUECDQ-UHFFFAOYSA-N 2-[[6-(1-benzofuran-2-yl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC=C2OC(C3=CC=C4N(C(C(C(=O)NCC(O)=O)=C(O)C4=C3)=O)C)=CC2=C1 PVAUXUZCDUECDQ-UHFFFAOYSA-N 0.000 claims 1
• FDHSKTGRIFCKQH-UHFFFAOYSA-N 2-[[6-(1-benzothiophen-2-yl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC=C2SC(C3=CC=C4N(C(C(C(=O)NCC(O)=O)=C(O)C4=C3)=O)C)=CC2=C1 FDHSKTGRIFCKQH-UHFFFAOYSA-N 0.000 claims 1
• DVBXIMJHGBENQY-UHFFFAOYSA-N 2-[[6-(2,4-dimethyl-1,3-thiazol-5-yl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound S1C(C)=NC(C)=C1C1=CC=C(N(C)C(=O)C(C(=O)NCC(O)=O)=C2O)C2=C1 DVBXIMJHGBENQY-UHFFFAOYSA-N 0.000 claims 1
• AOKCFRPADXZDRT-UHFFFAOYSA-N 2-[[6-(2-bromophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1Br AOKCFRPADXZDRT-UHFFFAOYSA-N 0.000 claims 1
• GQGFROMYHNFYQB-UHFFFAOYSA-N 2-[[6-(2-chloro-5-methylpyrimidin-4-yl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=CN=C(Cl)N=C1C1=CC=C(N(C)C(=O)C(C(=O)NCC(O)=O)=C2O)C2=C1 GQGFROMYHNFYQB-UHFFFAOYSA-N 0.000 claims 1
• IHAYYPODDQNBMT-UHFFFAOYSA-N 2-[[6-(2-chlorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1Cl IHAYYPODDQNBMT-UHFFFAOYSA-N 0.000 claims 1
• VHTNKZDLZCJIOV-UHFFFAOYSA-N 2-[[6-(2-cyclohexylphenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1C1CCCCC1 VHTNKZDLZCJIOV-UHFFFAOYSA-N 0.000 claims 1
• KWKXKGIRAOUYIX-UHFFFAOYSA-N 2-[[6-(2-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1F KWKXKGIRAOUYIX-UHFFFAOYSA-N 0.000 claims 1
• JRVYFAPRRLVJJS-UHFFFAOYSA-N 2-[[6-(2-formylphenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC=C1C=O JRVYFAPRRLVJJS-UHFFFAOYSA-N 0.000 claims 1
• FIJFYTZGRHQOAW-UHFFFAOYSA-N 2-[[6-(3-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC(F)=C1 FIJFYTZGRHQOAW-UHFFFAOYSA-N 0.000 claims 1
• JISFVAIEVSTGIG-UHFFFAOYSA-N 2-[[6-(3-formylphenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=CC(C=O)=C1 JISFVAIEVSTGIG-UHFFFAOYSA-N 0.000 claims 1
• ZXMBQUAZTPNOIT-UHFFFAOYSA-N 2-[[6-(4-chlorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=C(Cl)C=C1 ZXMBQUAZTPNOIT-UHFFFAOYSA-N 0.000 claims 1
• CJQHZSFISSJCAZ-UHFFFAOYSA-N 2-[[6-(4-fluorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=C(F)C=C1 CJQHZSFISSJCAZ-UHFFFAOYSA-N 0.000 claims 1
• RIYFOIJFRMVPIG-UHFFFAOYSA-N 2-[[6-(4-tert-butylphenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=C(C(C)(C)C)C=C1 RIYFOIJFRMVPIG-UHFFFAOYSA-N 0.000 claims 1
• FQEIBXUATSWBKS-UHFFFAOYSA-N 2-[[6-(6-chloropyridin-3-yl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC=C(Cl)N=C1 FQEIBXUATSWBKS-UHFFFAOYSA-N 0.000 claims 1
• QNDQYSVMBBNUIT-UHFFFAOYSA-N 2-[[6-(6-chloropyrimidin-4-yl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=C1C1=CC(Cl)=NC=N1 QNDQYSVMBBNUIT-UHFFFAOYSA-N 0.000 claims 1
• DNRVJXMSJXGOHL-UHFFFAOYSA-N 2-[[7-(2-chlorophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(C)C2=CC=1C1=CC=CC=C1Cl DNRVJXMSJXGOHL-UHFFFAOYSA-N 0.000 claims 1
• GVIHCWNMKWDFMY-UHFFFAOYSA-N 2-[[7-(3,5-dimethyl-1,2-oxazol-4-yl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound CC1=NOC(C)=C1C1=CC=C(C(O)=C(C(=O)NCC(O)=O)C(=O)N2C)C2=C1 GVIHCWNMKWDFMY-UHFFFAOYSA-N 0.000 claims 1
• BCNXXNDZSWLACE-UHFFFAOYSA-N 2-[[7-(3-chloro-4-methoxyphenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=C(Cl)C(OC)=CC=C1C1=CC=C(C(O)=C(C(=O)NCC(O)=O)C(=O)N2C)C2=C1 BCNXXNDZSWLACE-UHFFFAOYSA-N 0.000 claims 1
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