BRPI0714045A2 - composto, processo para preparação do mesmo, composição farmacêutica, processo para preparação da mesma, uso de um composto, e, métodos para tratamento de cáncer, e para modulação de atividade de quinase tipo pólo - Google Patents

Info

Publication number

BRPI0714045A2

BRPI0714045A2 BRPI0714045-2A BRPI0714045A BRPI0714045A2 BR PI0714045 A2 BRPI0714045 A2 BR PI0714045A2 BR PI0714045 A BRPI0714045 A BR PI0714045A BR PI0714045 A2 BRPI0714045 A2 BR PI0714045A2

Authority

BR

Brazil

Prior art keywords

optionally substituted

group

alkyl

optionally

hydrogen

Prior art date

2006-07-06

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 313
• 238000000034 method Methods 0.000 title claims abstract description 60
• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 19
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
• 201000011510 cancer Diseases 0.000 title claims abstract description 14
• 230000000694 effects Effects 0.000 title claims abstract description 10
• 108091000080 Phosphotransferase Proteins 0.000 title claims abstract description 8
• 102000020233 phosphotransferase Human genes 0.000 title claims abstract description 8
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 9
• -1 substituted Chemical class 0.000 claims description 222
• 229910052739 hydrogen Inorganic materials 0.000 claims description 181
• 239000001257 hydrogen Substances 0.000 claims description 181
• 125000005842 heteroatom Chemical group 0.000 claims description 148
• 125000000217 alkyl group Chemical group 0.000 claims description 132
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 93
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 83
• 229920006395 saturated elastomer Polymers 0.000 claims description 83
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 80
• 229910052757 nitrogen Inorganic materials 0.000 claims description 73
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 125000003545 alkoxy group Chemical group 0.000 claims description 69
• 125000001424 substituent group Chemical group 0.000 claims description 69
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 49
• 229910052799 carbon Inorganic materials 0.000 claims description 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 44
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 238000006243 chemical reaction Methods 0.000 claims description 37
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 36
• 125000004432 carbon atom Chemical group C* 0.000 claims description 36
• 229910052731 fluorine Inorganic materials 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 34
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 33
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 33
• 239000011230 binding agent Substances 0.000 claims description 33
• 239000011737 fluorine Substances 0.000 claims description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
• 150000001412 amines Chemical class 0.000 claims description 27
• 125000003386 piperidinyl group Chemical group 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 26
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 24
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims description 23
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
• 239000001301 oxygen Substances 0.000 claims description 22
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
• 125000004076 pyridyl group Chemical group 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 21
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 125000005592 polycycloalkyl group Polymers 0.000 claims description 21
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
• 125000004414 alkyl thio group Chemical group 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 20
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000004193 piperazinyl group Chemical group 0.000 claims description 18
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
• 239000011593 sulfur Substances 0.000 claims description 18
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
• 239000005977 Ethylene Substances 0.000 claims description 17
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• NSHIYIMHYBAIEY-UHFFFAOYSA-N ethyl hypochlorite Chemical compound CCOCl NSHIYIMHYBAIEY-UHFFFAOYSA-N 0.000 claims description 16
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 16
• 125000002757 morpholinyl group Chemical group 0.000 claims description 16
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 13
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 11
• 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 10
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 9
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 7
• 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
• 229910003827 NRaRb Inorganic materials 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
• 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 5
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 3
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 3
• 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 3
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
• ODWVFJUVKLPMDM-UHFFFAOYSA-N 9-methyl-9-azabicyclo[3.3.1]nonane Chemical class C1CCC2CCCC1N2C ODWVFJUVKLPMDM-UHFFFAOYSA-N 0.000 claims description 2
• PIYDNEWDZZFKKO-ILVMPNSOSA-N n-[(1s)-3-[7-(2-methylbenzimidazol-1-yl)-3-oxa-9-azabicyclo[3.3.1]nonan-9-yl]-1-phenylpropyl]cyclobutanecarboxamide Chemical class N([C@@H](CCN1C2COCC1CC(C2)N1C2=CC=CC=C2N=C1C)C=1C=CC=CC=1)C(=O)C1CCC1 PIYDNEWDZZFKKO-ILVMPNSOSA-N 0.000 claims description 2
• NRVBZYVECHGLAM-UHFFFAOYSA-N prop-2-ynyl hypochlorite Chemical compound ClOCC#C NRVBZYVECHGLAM-UHFFFAOYSA-N 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 45
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 3
• 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 2
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
• 229910003204 NH2 Inorganic materials 0.000 claims 1
• 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
• 230000008569 process Effects 0.000 abstract description 44
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 804
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 313
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 181
• 238000001819 mass spectrum Methods 0.000 description 173
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 164
• 238000005160 1H NMR spectroscopy Methods 0.000 description 161
• 239000000543 intermediate Substances 0.000 description 147
• 239000007787 solid Substances 0.000 description 120
• 239000000047 product Substances 0.000 description 111
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 95
• 229910021529 ammonia Inorganic materials 0.000 description 84
• 239000000203 mixture Substances 0.000 description 82
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 73
• 239000000243 solution Substances 0.000 description 66
• 238000004007 reversed phase HPLC Methods 0.000 description 63
• 239000011541 reaction mixture Substances 0.000 description 59
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 54
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 53
• 239000000463 material Substances 0.000 description 48
• WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 44
• 239000002904 solvent Substances 0.000 description 41
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 38
• 229960005419 nitrogen Drugs 0.000 description 38
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
• 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 30
• 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 30
• 230000014759 maintenance of location Effects 0.000 description 29
• 239000012043 crude product Substances 0.000 description 28
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
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• 239000007821 HATU Substances 0.000 description 24
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 24
• 150000001721 carbon Chemical group 0.000 description 23
• 239000002253 acid Substances 0.000 description 21
• 239000000377 silicon dioxide Substances 0.000 description 20
• 229960001124 trientine Drugs 0.000 description 20
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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• 239000003112 inhibitor Substances 0.000 description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
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• 150000001448 anilines Chemical class 0.000 description 16
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
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• 238000002360 preparation method Methods 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
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• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
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• 239000006260 foam Substances 0.000 description 12
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 12
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• 229910000024 caesium carbonate Inorganic materials 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 9
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• 238000001704 evaporation Methods 0.000 description 9
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• SXIGGRXSMJJARA-UHFFFAOYSA-N 2-chloro-9-phenyl-7,8-dihydro-5h-pyrimido[4,5-b][1,4]diazepin-6-one Chemical compound C12=NC(Cl)=NC=C2NC(=O)CCN1C1=CC=CC=C1 SXIGGRXSMJJARA-UHFFFAOYSA-N 0.000 description 5
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• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
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• 230000001028 anti-proliverative effect Effects 0.000 description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 5
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