CA2894636C - Quinolone derivatives - Google Patents
Quinolone derivatives Download PDFInfo
- Publication number
- CA2894636C CA2894636C CA2894636A CA2894636A CA2894636C CA 2894636 C CA2894636 C CA 2894636C CA 2894636 A CA2894636 A CA 2894636A CA 2894636 A CA2894636 A CA 2894636A CA 2894636 C CA2894636 C CA 2894636C
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- hydroxy
- carboxamido
- group
- acetic acid
- 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.)
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- 150000007660 quinolones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- -1 cycloalkanylalkyl Chemical group 0.000 claims description 71
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 19
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 208000007502 anemia Diseases 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 7
- 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 8
- 229910020008 S(O) Inorganic materials 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 138
- 238000000034 method Methods 0.000 abstract description 58
- 150000003839 salts Chemical class 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 389
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 202
- 238000005481 NMR spectroscopy Methods 0.000 description 46
- 239000000047 product Substances 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- 150000003254 radicals Chemical class 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 102000003951 Erythropoietin Human genes 0.000 description 20
- 108090000394 Erythropoietin Proteins 0.000 description 20
- 229940105423 erythropoietin Drugs 0.000 description 20
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 20
- 239000012043 crude product Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- 206010021143 Hypoxia Diseases 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 102000004079 Prolyl Hydroxylases Human genes 0.000 description 8
- 108010043005 Prolyl Hydroxylases Proteins 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000007954 hypoxia Effects 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 102000001554 Hemoglobins Human genes 0.000 description 5
- 108010054147 Hemoglobins Proteins 0.000 description 5
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 5
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
- 125000005518 carboxamido group Chemical group 0.000 description 5
- 210000003743 erythrocyte Anatomy 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003305 oral gavage Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 208000028867 ischemia Diseases 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- BNGKGGYBRUBUFE-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-1-phenylmethoxyquinoline-3-carbonyl)amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C2=CC=CC=C2N1OCC1=CC=CC=C1 BNGKGGYBRUBUFE-UHFFFAOYSA-N 0.000 description 3
- IKRKQQLJYBAPQT-UHFFFAOYSA-N 2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C2=CC=CC=C2N1OCC1CC1 IKRKQQLJYBAPQT-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 3
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 3
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
- 125000005336 allyloxy group Chemical group 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 208000020832 chronic kidney disease Diseases 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- ZWGLDZCXDAKIFM-UHFFFAOYSA-N ethyl 2-(hydroxyamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NO ZWGLDZCXDAKIFM-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000033444 hydroxylation Effects 0.000 description 3
- 238000005805 hydroxylation reaction Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- PFZBHKPWMNTOLD-SFHVURJKSA-N (2s)-2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]-2-phenylacetic acid Chemical compound N([C@H](C(=O)O)C=1C=CC=CC=1)C(=O)C(C1=O)=C(O)C2=CC=CC=C2N1OCC1CC1 PFZBHKPWMNTOLD-SFHVURJKSA-N 0.000 description 2
- PQUGTBHEJZVTPM-HNNXBMFYSA-N (2s)-2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]-3-methylbutanoic acid Chemical compound O=C1C(C(=O)N[C@@H](C(C)C)C(O)=O)=C(O)C2=CC=CC=C2N1OCC1CC1 PQUGTBHEJZVTPM-HNNXBMFYSA-N 0.000 description 2
- JCSCDPOJLDEXLM-AWEZNQCLSA-N (2s)-2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]-4-methylpentanoic acid Chemical compound O=C1C(C(=O)N[C@@H](CC(C)C)C(O)=O)=C(O)C2=CC=CC=C2N1OCC1CC1 JCSCDPOJLDEXLM-AWEZNQCLSA-N 0.000 description 2
- NFLDLYYKSTYHBV-ZDUSSCGKSA-N (2s)-4-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]-2-hydroxybutanoic acid Chemical compound O=C1C(C(=O)NCC[C@H](O)C(O)=O)=C(O)C2=CC=CC=C2N1OCC1CC1 NFLDLYYKSTYHBV-ZDUSSCGKSA-N 0.000 description 2
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 2
- AAXUPKIFSSDXLZ-UHFFFAOYSA-N 2-[(1,4-dihydroxy-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2N(O)C(=O)C(C(=O)NCC(=O)O)=C(O)C2=C1 AAXUPKIFSSDXLZ-UHFFFAOYSA-N 0.000 description 2
- APYIJHRTLIKJFB-UHFFFAOYSA-N 2-[(1-but-2-ynoxy-4-hydroxy-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OCC#CC)C2=C1 APYIJHRTLIKJFB-UHFFFAOYSA-N 0.000 description 2
- WRTIQJTZFYQPMD-UHFFFAOYSA-N 2-[(1-heptoxy-4-hydroxy-2-oxoquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OCCCCCCC)C2=C1 WRTIQJTZFYQPMD-UHFFFAOYSA-N 0.000 description 2
- NUOBVOHOFNWDNI-UHFFFAOYSA-N 2-[(4,6-dihydroxy-2-oxo-1-propoxyquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=C(O)C=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OCCC)C2=C1 NUOBVOHOFNWDNI-UHFFFAOYSA-N 0.000 description 2
- ZZFPJKYVGFOSSL-UHFFFAOYSA-N 2-[(4-hydroxy-1-methoxy-2-oxo-1,5-naphthyridine-3-carbonyl)amino]acetic acid Chemical compound C1=CN=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OC)C2=C1 ZZFPJKYVGFOSSL-UHFFFAOYSA-N 0.000 description 2
- OLMKVNAYDVXHGU-UHFFFAOYSA-N 2-[(4-hydroxy-1-methoxy-2-oxo-5,7-dihydrothieno[3,4-b]pyridine-3-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(OC)C2=C1CSC2 OLMKVNAYDVXHGU-UHFFFAOYSA-N 0.000 description 2
- LAKDWDBVTNMSQP-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-1-pentan-3-yloxyquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OC(CC)CC)C2=C1 LAKDWDBVTNMSQP-UHFFFAOYSA-N 0.000 description 2
- XIRJRLBBDMEUAS-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-1-phenylmethoxy-6-phenylsulfanylquinoline-3-carbonyl)amino]acetic acid Chemical compound C=1C=C2N(OCC=3C=CC=CC=3)C(=O)C(C(=O)NCC(=O)O)=C(O)C2=CC=1SC1=CC=CC=C1 XIRJRLBBDMEUAS-UHFFFAOYSA-N 0.000 description 2
- LTIOGLVHBZZXPA-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-1-phenylmethoxyquinoline-3-carbonyl)amino]-2-methylpropanoic acid Chemical compound O=C1C(C(=O)NC(C)(C)C(O)=O)=C(O)C2=CC=CC=C2N1OCC1=CC=CC=C1 LTIOGLVHBZZXPA-UHFFFAOYSA-N 0.000 description 2
- DPCILLNGCDNKGF-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-1-propan-2-yloxyquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OC(C)C)C2=C1 DPCILLNGCDNKGF-UHFFFAOYSA-N 0.000 description 2
- GCUWPVMBNAJYEE-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-1-propoxy-5,6,7,8-tetrahydroquinoline-3-carbonyl)amino]acetic acid Chemical compound C1CCCC2=C1N(OCCC)C(=O)C(C(=O)NCC(O)=O)=C2O GCUWPVMBNAJYEE-UHFFFAOYSA-N 0.000 description 2
- BIWBUVZCTAFBIW-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-1-propoxyquinoline-3-carbonyl)amino]acetic acid Chemical compound C1=CC=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OCCC)C2=C1 BIWBUVZCTAFBIW-UHFFFAOYSA-N 0.000 description 2
- UZDVTRISPQJECU-UHFFFAOYSA-N 2-[(7-ethoxy-4-hydroxy-6-oxothieno[2,3-b]pyridine-5-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(OCC)C2=C1C=CS2 UZDVTRISPQJECU-UHFFFAOYSA-N 0.000 description 2
- CNUPSAPQVLBKDE-UHFFFAOYSA-N 2-[(7-hydroxy-4-methoxy-5-oxo-[1,3]oxazolo[4,5-b]pyridine-6-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(OC)C2=C1OC=N2 CNUPSAPQVLBKDE-UHFFFAOYSA-N 0.000 description 2
- CPUVSZBNGSFLKM-UHFFFAOYSA-N 2-[(7-hydroxy-4-methoxy-5-oxo-[1,3]thiazolo[4,5-b]pyridine-6-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(OC)C2=C1SC=N2 CPUVSZBNGSFLKM-UHFFFAOYSA-N 0.000 description 2
- USFGXCUQCQVPLQ-UHFFFAOYSA-N 2-[(7-hydroxy-4-methoxy-5-oxothieno[3,2-b]pyridine-6-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(OC)C2=C1SC=C2 USFGXCUQCQVPLQ-UHFFFAOYSA-N 0.000 description 2
- YTSWNOGDRHBYAI-UHFFFAOYSA-N 2-[(7-hydroxy-5-oxo-4-propoxy-[1,3]oxazolo[4,5-b]pyridine-6-carbonyl)amino]acetic acid Chemical compound OC1=C(C(=O)NCC(O)=O)C(=O)N(OCCC)C2=C1OC=N2 YTSWNOGDRHBYAI-UHFFFAOYSA-N 0.000 description 2
- BUXMOWVEJDOEAW-UHFFFAOYSA-N 2-[(8-hydroxy-5-methoxy-6-oxopyrido[2,3-b]pyrazine-7-carbonyl)amino]acetic acid Chemical compound C1=CN=C2C(O)=C(C(=O)NCC(O)=O)C(=O)N(OC)C2=N1 BUXMOWVEJDOEAW-UHFFFAOYSA-N 0.000 description 2
- XIWXUFVJQSWXOP-UHFFFAOYSA-N 2-[[1-(1,3-benzothiazol-2-ylmethoxy)-6-chloro-4-hydroxy-2-oxoquinoline-3-carbonyl]amino]acetic acid Chemical compound C1=CC=C2SC(CON3C4=CC=C(Cl)C=C4C(O)=C(C3=O)C(=O)NCC(=O)O)=NC2=C1 XIWXUFVJQSWXOP-UHFFFAOYSA-N 0.000 description 2
- CJNSJEUACHLVFR-UHFFFAOYSA-N 2-[[1-(cyclopropylmethoxy)-4-hydroxy-2-oxo-6-phenoxyquinoline-3-carbonyl]amino]acetic acid Chemical compound C=1C=C2N(OCC3CC3)C(=O)C(C(=O)NCC(=O)O)=C(O)C2=CC=1OC1=CC=CC=C1 CJNSJEUACHLVFR-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Cardiology (AREA)
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- Vascular Medicine (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epidemiology (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| PCT/IN2013/000796 WO2014102818A1 (en) | 2012-12-24 | 2013-12-23 | Novel quinolone derivatives |
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| WO2016045125A1 (en) | 2014-09-28 | 2016-03-31 | Merck Sharp & Dohme Corp. | Inhibitors of hif prolyl hydroxylase |
| CL2015003047A1 (es) * | 2015-10-15 | 2016-06-17 | Univ Chile | Método ex vivo para detectar precozmente injuria renal aguda en pacientes críticos, que comprende la mediciom en una muestra de tres proteinas como biomarcadores, factor de crecimiento fibroblástico 23, klotho y eritropoyetina |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| CN108069957B (zh) * | 2016-11-09 | 2022-11-04 | 广东东阳光药业有限公司 | 脯氨酰羟化酶抑制剂及其用途 |
| CN108484598B (zh) * | 2017-05-09 | 2021-03-02 | 杭州安道药业有限公司 | 吲哚嗪衍生物及其在医药上的应用 |
| KR102526964B1 (ko) | 2018-02-26 | 2023-04-28 | 길리애드 사이언시즈, 인코포레이티드 | Hbv 복제 억제제로서의 치환된 피롤리진 화합물 |
| TW202200547A (zh) * | 2020-03-13 | 2022-01-01 | 印度商卡地拉保健有限公司 | 喹啉酮化合物的新穎鹽類 |
| EP4121009A4 (en) * | 2020-03-17 | 2024-04-17 | Zydus Lifesciences Limited | Formulation comprising hif prolyl hydroxylase inhibitors |
| TW202200134A (zh) | 2020-04-20 | 2022-01-01 | 美商阿克比治療有限公司 | 治療病毒感染、器官損傷及相關症狀之方法 |
| WO2021240454A1 (en) * | 2020-05-29 | 2021-12-02 | Cadila Healthcare Limited | Treatment for psoriasis and skin inflammatory diseases |
| EP4157220A1 (en) * | 2020-06-01 | 2023-04-05 | Zydus Lifesciences Limited | Treatment for the inflammatory bowel disease |
| WO2022150623A1 (en) | 2021-01-08 | 2022-07-14 | Akebia Therapeutics, Inc. | Compounds and composition for the treatment of anemia |
| MX2023010998A (es) * | 2021-03-19 | 2023-09-28 | Zydus Lifesciences Ltd | Un compuesto de quinolona en formas solidas y procesos para su preparacion. |
| BR112023018949A2 (pt) * | 2021-03-19 | 2023-10-17 | Zydus Lifesciences Ltd | Composto, uso do mesmo para tratar anemia falciforme e composição farmacêutica compreendendo o referido composto |
| WO2022238745A1 (en) * | 2021-05-14 | 2022-11-17 | Zydus Lifesciences Limited | Topical pharmaceutical composition of hif prolyl hydroxylase inhibitors |
| TW202313072A (zh) | 2021-05-27 | 2023-04-01 | 美商凱立克斯生物製藥股份有限公司 | 檸檬酸鐵之兒科調配物 |
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| EP2357175A1 (en) | 2003-06-06 | 2011-08-17 | Fibrogen, Inc. | isoquinoline derivatives AND THEIR USE IN INCREASING ENDOGENEOUS ERYTHROPOIETIN |
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| US7728130B2 (en) * | 2005-12-09 | 2010-06-01 | Amgen Inc. | Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity |
| TW200808793A (en) * | 2006-03-07 | 2008-02-16 | Smithkline Beecham Corp | Prolyl hydroxylase inhibitors |
| BRPI0710527B8 (pt) * | 2006-04-04 | 2021-05-25 | Fibrogen Inc | compostos de pirrolo- e tiazolo-piridina e composição farmacêutica que os compreende |
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| WO2008010964A1 (en) * | 2006-07-17 | 2008-01-24 | Merck & Co., Inc. | 1-hydroxy naphthyridine compounds as anti-hiv agents |
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| CA2683956C (en) * | 2007-04-18 | 2012-12-18 | Amgen Inc. | Quinolones and azaquinolones that inhibit prolyl hydroxylase |
| CA2683758A1 (en) * | 2007-04-18 | 2008-10-30 | Merck & Co., Inc. | Novel 1,8-naphthyridine compounds |
| AU2008248234B2 (en) * | 2007-05-04 | 2011-02-03 | Amgen Inc. | Thienopyridine and thiazolopyridine derivatives that inhibit prolyl hydroxylase activity |
| US8097620B2 (en) * | 2007-05-04 | 2012-01-17 | Amgen Inc. | Diazaquinolones that inhibit prolyl hydroxylase activity |
| AU2008251031B2 (en) | 2007-05-16 | 2013-12-19 | Norman Terry Cowper | System and method for maximising solids concentration of slurry pumped through a pipeline |
| AU2008329746A1 (en) * | 2007-11-30 | 2009-06-04 | Glaxosmithkline Llc | Prolyl hydroxylase inhibitors |
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| JP2011513222A (ja) * | 2008-02-25 | 2011-04-28 | メルク・シャープ・エンド・ドーム・コーポレイション | テトラヒドロチエノピリジン |
| CA2716798A1 (en) * | 2008-02-25 | 2009-09-03 | Merck Sharp & Dohme Corp. | Tetrahydrofuropyridones |
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| PT2455381E (pt) | 2009-07-17 | 2014-06-24 | Japan Tobacco Inc | Composto de triazolopiridina e sua acção como inibidor da prolil-hidroxilase e indutor da produção de eritropoietina |
| TW201109324A (en) * | 2009-08-20 | 2011-03-16 | Vifor Int Ag | Novel quinoline hepcidine antagonists |
| CN103608346B (zh) | 2011-02-02 | 2016-06-15 | 菲布罗根有限公司 | 作为缺氧诱导因子(hif)羟化酶抑制剂的萘啶衍生物 |
| WO2013043621A1 (en) | 2011-09-23 | 2013-03-28 | Merck Sharp & Dohme Corp. | Substituted pyrimidines |
| CA2863279A1 (en) * | 2012-01-31 | 2013-08-08 | Toyama Chemical Co., Ltd. | Heterocyclic compound having anti-hiv activity |
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