BR112012008330B1 - Compostos quinazolinas, suas composições farmacêuticas e seus usos - Google Patents
Compostos quinazolinas, suas composições farmacêuticas e seus usos Download PDFInfo
- Publication number
- BR112012008330B1 BR112012008330B1 BR112012008330-9A BR112012008330A BR112012008330B1 BR 112012008330 B1 BR112012008330 B1 BR 112012008330B1 BR 112012008330 A BR112012008330 A BR 112012008330A BR 112012008330 B1 BR112012008330 B1 BR 112012008330B1
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- heteroaryl
- heterocyclyl
- cycloalkyl
- aryl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 239000003112 inhibitor Substances 0.000 claims abstract description 15
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 6
- 230000006793 arrhythmia Effects 0.000 claims abstract description 6
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 896
- 125000001072 heteroaryl group Chemical group 0.000 claims description 856
- 125000000217 alkyl group Chemical group 0.000 claims description 595
- 125000003342 alkenyl group Chemical group 0.000 claims description 486
- 229910052757 nitrogen Inorganic materials 0.000 claims description 318
- 125000005842 heteroatom Chemical group 0.000 claims description 317
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 314
- 229910052760 oxygen Inorganic materials 0.000 claims description 307
- 229910052717 sulfur Inorganic materials 0.000 claims description 307
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 301
- 125000004432 carbon atom Chemical group C* 0.000 claims description 298
- 229910052740 iodine Inorganic materials 0.000 claims description 291
- 229910052794 bromium Inorganic materials 0.000 claims description 288
- 229910052801 chlorine Inorganic materials 0.000 claims description 282
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 281
- 125000003118 aryl group Chemical group 0.000 claims description 264
- 229910052731 fluorine Inorganic materials 0.000 claims description 263
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 255
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 242
- 125000003545 alkoxy group Chemical group 0.000 claims description 242
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 44
- -1 -CO2R25 Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
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- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 229940123208 Biguanide Drugs 0.000 claims description 6
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 6
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 claims description 6
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- NVXFXLSOGLFXKQ-JMSVASOKSA-N (2s)-1-[(2r,4r)-5-ethoxy-2,4-dimethyl-5-oxopentanoyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)[C@H](C)C[C@@H](C)C(=O)OCC)[C@H](C(O)=O)CC2=C1 NVXFXLSOGLFXKQ-JMSVASOKSA-N 0.000 claims description 3
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 claims description 3
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 3
- OFJRNBWSFXEHSA-UHFFFAOYSA-N 2-(3-amino-1,2-benzoxazol-5-yl)-n-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide Chemical compound CN(C)CC1=NC=CN1C(C=C1F)=CC=C1NC(=O)C1=CC(C(F)(F)F)=NN1C1=CC=C(ON=C2N)C2=C1 OFJRNBWSFXEHSA-UHFFFAOYSA-N 0.000 claims description 3
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- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims description 3
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- LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 claims description 3
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