BRPI0616672A2 - composto, formulação farmacêutica, uso de um composto, e, processo para preparar um composto - Google Patents

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Publication number

BRPI0616672A2

BRPI0616672A2 BRPI0616672-5A BRPI0616672A BRPI0616672A2 BR PI0616672 A2 BRPI0616672 A2 BR PI0616672A2 BR PI0616672 A BRPI0616672 A BR PI0616672A BR PI0616672 A2 BRPI0616672 A2 BR PI0616672A2

Authority

BR

Brazil

Prior art keywords

alkyl

imidazo

phenyl

haloalkyl

optionally substituted

Prior art date

2005-10-03

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 327
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
• 150000003839 salts Chemical class 0.000 claims abstract description 60
• 239000012453 solvate Substances 0.000 claims abstract description 49
• 238000000034 method Methods 0.000 claims abstract description 36
• 239000012458 free base Substances 0.000 claims abstract description 25
• 230000008569 process Effects 0.000 claims abstract description 11
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 152
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims description 110
• 239000001257 hydrogen Substances 0.000 claims description 109
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 104
• -1 NRdRe Chemical group 0.000 claims description 100
• 125000005843 halogen group Chemical group 0.000 claims description 98
• 150000002431 hydrogen Chemical group 0.000 claims description 93
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 87
• 125000000217 alkyl group Chemical group 0.000 claims description 84
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 67
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 53
• 125000005842 heteroatom Chemical group 0.000 claims description 49
• 125000004429 atom Chemical group 0.000 claims description 46
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 43
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 41
• 125000003118 aryl group Chemical group 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• 229910052760 oxygen Inorganic materials 0.000 claims description 37
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 36
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 35
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 35
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 229910052717 sulfur Inorganic materials 0.000 claims description 33
• 125000001188 haloalkyl group Chemical group 0.000 claims description 31
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 25
• 206010012289 Dementia Diseases 0.000 claims description 24
• 238000006243 chemical reaction Methods 0.000 claims description 24
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• 208000010877 cognitive disease Diseases 0.000 claims description 18
• MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 17
• 150000002367 halogens Chemical group 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 230000002265 prevention Effects 0.000 claims description 16
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims description 14
• 238000001816 cooling Methods 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 13
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 239000005711 Benzoic acid Substances 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• FXHZWSCNTVBMJZ-UHFFFAOYSA-N [4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(Cl)=C3N=2)C=C1 FXHZWSCNTVBMJZ-UHFFFAOYSA-N 0.000 claims description 12
• 235000010233 benzoic acid Nutrition 0.000 claims description 12
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 12
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• IJXJGIWROCZHKS-UHFFFAOYSA-N 4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(O)=O)N2 IJXJGIWROCZHKS-UHFFFAOYSA-N 0.000 claims description 10
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 10
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• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• XNQXCKZRTQGHQV-UHFFFAOYSA-N 7-chloro-2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=CC(Cl)=C3N=2)C=C1 XNQXCKZRTQGHQV-UHFFFAOYSA-N 0.000 claims description 7
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• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
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• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 230000009467 reduction Effects 0.000 claims description 6
• HMLRBRPZIQSPBV-UHFFFAOYSA-N 3-[7-(4-carbamoylphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=NC2=C1N=C(C=1C=C(C=CC=1)C(O)=O)N2 HMLRBRPZIQSPBV-UHFFFAOYSA-N 0.000 claims description 5
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• WGFCHNWKFQLGTG-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-nitro-2-phenylmethoxypyridine Chemical compound C1=CC(OC)=CC=C1C1=CC=NC(OCC=2C=CC=CC=2)=C1[N+]([O-])=O WGFCHNWKFQLGTG-UHFFFAOYSA-N 0.000 claims description 4
• JGUVOZHBKZAPNL-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-nitropyridin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=CC=NC(N)=C1[N+]([O-])=O JGUVOZHBKZAPNL-UHFFFAOYSA-N 0.000 claims description 4
• XGBAZKBVSNNKJF-UHFFFAOYSA-N 4-(7-iodo-1h-imidazo[4,5-b]pyridin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=C(I)C=CN=C2N1 XGBAZKBVSNNKJF-UHFFFAOYSA-N 0.000 claims description 4
• DRJFKMUKYAQPQR-UHFFFAOYSA-N 4-[2-[4-(4-methylpiperazine-1-carbonyl)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]benzonitrile;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(=C3N=2)C=2C=CC(=CC=2)C#N)C=C1 DRJFKMUKYAQPQR-UHFFFAOYSA-N 0.000 claims description 4
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• YOOOBTGZFFDDAN-UHFFFAOYSA-N [4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)N1CCOCC1)N2 YOOOBTGZFFDDAN-UHFFFAOYSA-N 0.000 claims description 4
• NHECRIZPDJYOLQ-UHFFFAOYSA-N [4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)N1CCCCC1)N2 NHECRIZPDJYOLQ-UHFFFAOYSA-N 0.000 claims description 4
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• XCLZKTYDTPVQIK-UHFFFAOYSA-N methyl 4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC(C=2NC3=NC=CC(=C3N=2)C=2C=CC(OC)=CC=2)=C1 XCLZKTYDTPVQIK-UHFFFAOYSA-N 0.000 claims description 4
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• MIORAZJRJQHQHZ-UHFFFAOYSA-N 2-(furan-2-ylmethyl)-7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(CC=1OC=CC=1)N2 MIORAZJRJQHQHZ-UHFFFAOYSA-N 0.000 claims description 3
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