BRPI0710908A2 - compostos inibidores de fosfoinositìdeo 3-cinase e composições farmacêuticas contendo-os - Google Patents

Info

Publication number

BRPI0710908A2

BRPI0710908A2 BRPI0710908-3A BRPI0710908A BRPI0710908A2 BR PI0710908 A2 BRPI0710908 A2 BR PI0710908A2 BR PI0710908 A BRPI0710908 A BR PI0710908A BR PI0710908 A2 BRPI0710908 A2 BR PI0710908A2

Authority

BR

Brazil

Prior art keywords

indazol

morpholinothieno

pyrimidin

pyrimidine

methyl

Prior art date

2006-04-26

Links

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• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 title claims description 55
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 title claims description 39
• 238000000034 method Methods 0.000 claims abstract description 186
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• 150000003839 salts Chemical class 0.000 claims abstract description 36
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• 238000011282 treatment Methods 0.000 claims abstract description 27
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• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 18
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• 239000012453 solvate Substances 0.000 claims abstract description 17
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• -1 C3-C12 carbocyclyl Chemical group 0.000 claims description 281
• 239000000203 mixture Substances 0.000 claims description 163
• 125000000623 heterocyclic group Chemical group 0.000 claims description 62
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 50
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 43
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
• 229910052757 nitrogen Inorganic materials 0.000 claims description 38
• 208000035475 disorder Diseases 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
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• 229910052760 oxygen Inorganic materials 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 23
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• 239000003814 drug Substances 0.000 claims description 22
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 22
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 21
• 125000002619 bicyclic group Chemical group 0.000 claims description 21
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 230000027455 binding Effects 0.000 claims description 19
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 229910052740 iodine Inorganic materials 0.000 claims description 17
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 16
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• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 13
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
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• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
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• 125000006413 ring segment Chemical group 0.000 claims description 8
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• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
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• 150000003456 sulfonamides Chemical class 0.000 claims description 6
• ZZAKLGGGMWORRT-UHFFFAOYSA-N 1-methylsulfonylpiperazine Chemical compound CS(=O)(=O)N1CCNCC1 ZZAKLGGGMWORRT-UHFFFAOYSA-N 0.000 claims description 5
• XNCSTYGCHDBACY-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N1=C(C=2C=3C=NNC=3C=CC=2)N=C2SC(C(=O)O)=CC2=C1N1CCOCC1 XNCSTYGCHDBACY-UHFFFAOYSA-N 0.000 claims description 5
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• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
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• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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• 230000003612 virological effect Effects 0.000 claims description 4
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
• FDDMBVCMOPBZFJ-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-6-(3-methylsulfonylphenyl)-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound CS(=O)(=O)C1=CC=CC(C=2OC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)=C1 FDDMBVCMOPBZFJ-UHFFFAOYSA-N 0.000 claims 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 claims description 3
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• 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 description 3
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• VIOPFQOZMDFRIZ-LLVKDONJSA-N (1r)-1-[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]ethanol Chemical compound C=12SC([C@H](O)C)=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 VIOPFQOZMDFRIZ-LLVKDONJSA-N 0.000 claims description 2
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