BR112015014222B1 - Composto e composição farmacêutica - Google Patents

Info

Publication number

BR112015014222B1

BR112015014222B1 BR112015014222-2A BR112015014222A BR112015014222B1 BR 112015014222 B1 BR112015014222 B1 BR 112015014222B1 BR 112015014222 A BR112015014222 A BR 112015014222A BR 112015014222 B1 BR112015014222 B1 BR 112015014222B1

Authority

BR

Brazil

Prior art keywords

hydroxy

oxo

carboxamido

acetic acid

dihydroquinoline

Prior art date

2012-12-24

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 113
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
• 208000007502 anemia Diseases 0.000 claims abstract description 14
• -1 cycloalkanylalkyl Chemical group 0.000 claims description 73
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 14
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
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• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• 150000001721 carbon Chemical group 0.000 claims 2
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 1
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• 238000002360 preparation method Methods 0.000 abstract description 138
• 238000000034 method Methods 0.000 abstract description 59
• 150000003839 salts Chemical class 0.000 abstract description 9
• 239000003814 drug Substances 0.000 abstract description 3
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• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 184
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 117
• 238000005160 1H NMR spectroscopy Methods 0.000 description 114
• 239000000047 product Substances 0.000 description 50
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
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• 150000003254 radicals Chemical class 0.000 description 25
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• 108090000394 Erythropoietin Proteins 0.000 description 18
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• 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 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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• 108010074633 Mixed Function Oxygenases Proteins 0.000 description 7
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• 238000006243 chemical reaction Methods 0.000 description 7
• 230000007954 hypoxia Effects 0.000 description 7
• 239000001301 oxygen Substances 0.000 description 7
• 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
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• ZWGLDZCXDAKIFM-UHFFFAOYSA-N ethyl 2-(hydroxyamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NO ZWGLDZCXDAKIFM-UHFFFAOYSA-N 0.000 description 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
• 230000001965 increasing effect Effects 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 210000003743 erythrocyte Anatomy 0.000 description 5
• 235000019439 ethyl acetate Nutrition 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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• 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
• 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
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• KEKOBKNECTWOAJ-UHFFFAOYSA-N 2-[[4-hydroxy-2-oxo-1-[[4-(trifluoromethyl)phenyl]methoxy]-1,8-naphthyridine-3-carbonyl]amino]acetic acid Chemical compound O=C1C(C(=O)NCC(=O)O)=C(O)C2=CC=CN=C2N1OCC1=CC=C(C(F)(F)F)C=C1 KEKOBKNECTWOAJ-UHFFFAOYSA-N 0.000 description 3
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
• 102000001554 Hemoglobins Human genes 0.000 description 3
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• 101001046870 Homo sapiens Hypoxia-inducible factor 1-alpha Proteins 0.000 description 3
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• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
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• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 2
• KCIDDQXSAVBNIT-UHFFFAOYSA-N 1-(cyclopropylmethoxy)-4-hydroxy-n-[2-(methanesulfonamido)-2-oxoethyl]-2-oxoquinoline-3-carboxamide Chemical compound O=C1C(C(=O)NCC(=O)NS(=O)(=O)C)=C(O)C2=CC=CC=C2N1OCC1CC1 KCIDDQXSAVBNIT-UHFFFAOYSA-N 0.000 description 2
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