RU2011107227A - Бензоимидазольные производные и ингибиторы гликоген-синтаза-киназы-3 бета, содержащие такие производные - Google Patents
Бензоимидазольные производные и ингибиторы гликоген-синтаза-киназы-3 бета, содержащие такие производные Download PDFInfo
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- RU2011107227A RU2011107227A RU2011107227/13A RU2011107227A RU2011107227A RU 2011107227 A RU2011107227 A RU 2011107227A RU 2011107227/13 A RU2011107227/13 A RU 2011107227/13A RU 2011107227 A RU2011107227 A RU 2011107227A RU 2011107227 A RU2011107227 A RU 2011107227A
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- RU
- Russia
- Prior art keywords
- hydroxy
- benzo
- imidazole
- carboxamide
- thiophen
- Prior art date
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- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 title claims 2
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract 23
- -1 p-toluenesulfonylamino Chemical group 0.000 claims abstract 19
- 125000001424 substituent group Chemical group 0.000 claims abstract 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 6
- 150000001408 amides Chemical class 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 4
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 3
- 150000002367 halogens Chemical group 0.000 claims abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- GOPDFXUMARJJEA-UHFFFAOYSA-N amino(nitro)azanide Chemical compound N[N-][N+]([O-])=O GOPDFXUMARJJEA-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 8
- 150000001412 amines Chemical class 0.000 claims 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- PEELIBUMTXGKIM-UHFFFAOYSA-N 7-hydroxy-n-[2-(3-methoxyphenyl)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound COC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3C(O)=CC=2)C=2SC=CC=2)=C1 PEELIBUMTXGKIM-UHFFFAOYSA-N 0.000 claims 2
- 150000001448 anilines Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ZUVFATUZMPMHOH-NSHDSACASA-N (2s)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=2N=C(NC=2C(O)=CC=1)C=1SC=CC=1)C1=CN=CN1 ZUVFATUZMPMHOH-NSHDSACASA-N 0.000 claims 1
- MUVKYWUUGPEPCZ-INIZCTEOSA-N (2s)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(C=1N=2)=CC=C(O)C=1NC=2C1=CC=CS1 MUVKYWUUGPEPCZ-INIZCTEOSA-N 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- UVKHHBRUBXLKTP-QPJJXVBHSA-N (e)-3-(1h-imidazol-5-yl)-n-(7-methoxy-2-thiophen-2-yl-1h-benzimidazol-4-yl)prop-2-enamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(OC)=CC=C1NC(=O)\C=C\C1=CN=CN1 UVKHHBRUBXLKTP-QPJJXVBHSA-N 0.000 claims 1
- MZHSZYCOVLPFLX-UHFFFAOYSA-N 1-(2-cyclopropyl-7-hydroxy-1h-benzimidazol-4-yl)-3-(4-hydroxyphenyl)urea Chemical compound C1=CC(O)=CC=C1NC(=O)NC1=CC=C(O)C2=C1N=C(C1CC1)N2 MZHSZYCOVLPFLX-UHFFFAOYSA-N 0.000 claims 1
- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 claims 1
- WEPGUFPFXZWBCK-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-(1,3-thiazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NC1=NC=CS1 WEPGUFPFXZWBCK-UHFFFAOYSA-N 0.000 claims 1
- SBZNOMSJFLVNDA-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-(2-phenylethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=CC=CC=C1 SBZNOMSJFLVNDA-UHFFFAOYSA-N 0.000 claims 1
- JIMLNOXLFHMJAE-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-[2-(1-methylpyrrol-2-yl)ethyl]-1h-benzimidazole-4-carboxamide Chemical compound CN1C=CC=C1CCNC(=O)C1=CC=C(O)C2=C1N=C(C=1OC=CC=1)N2 JIMLNOXLFHMJAE-UHFFFAOYSA-N 0.000 claims 1
- ODQBWZNQIHEVET-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-[2-[[5-[(4-methylphenyl)sulfonylamino]pyridin-2-yl]amino]ethyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=N1)=CC=C1NCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1OC=CC=1)N2 ODQBWZNQIHEVET-UHFFFAOYSA-N 0.000 claims 1
- SKWUVECPMONQGU-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-phenyl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NC1=CC=CC=C1 SKWUVECPMONQGU-UHFFFAOYSA-N 0.000 claims 1
- CUPJXQFPTJBZOZ-UHFFFAOYSA-N 2-cyclopentyl-7-hydroxy-n-[2-(4-hydroxyphenyl)ethyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C1CCCC1)=N2 CUPJXQFPTJBZOZ-UHFFFAOYSA-N 0.000 claims 1
- MXQIXJJYQFBVJN-UHFFFAOYSA-N 2-cyclopropyl-n-(2,3-dihydroxypropyl)-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound N1C=2C(C(=O)NCC(O)CO)=CC=C(O)C=2N=C1C1CC1 MXQIXJJYQFBVJN-UHFFFAOYSA-N 0.000 claims 1
- SWMCGIYDIXUCLO-UHFFFAOYSA-N 2-cyclopropyl-n-(4-hydroxyphenyl)-7-methoxy-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(OC)=CC=C1C(=O)NC1=CC=C(O)C=C1 SWMCGIYDIXUCLO-UHFFFAOYSA-N 0.000 claims 1
- MWOFSHRVMPYTGX-UHFFFAOYSA-N 2-cyclopropyl-n-[2-(dimethylamino)ethyl]-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound N1C=2C(C(=O)NCCN(C)C)=CC=C(O)C=2N=C1C1CC1 MWOFSHRVMPYTGX-UHFFFAOYSA-N 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- KSMCYMNDVNDOEW-UHFFFAOYSA-N 7-fluoro-n-[2-(1h-imidazol-5-yl)ethyl]-2-thiophen-2-yl-3h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(F)=CC=C1C(=O)NCCC1=CN=CN1 KSMCYMNDVNDOEW-UHFFFAOYSA-N 0.000 claims 1
- VLBUEFFYBHGVQX-UHFFFAOYSA-N 7-hydroxy-2-phenyl-n-(2-phenylethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C=3C=CC=CC=3)=NC=2C(O)=CC=C1C(=O)NCCC1=CC=CC=C1 VLBUEFFYBHGVQX-UHFFFAOYSA-N 0.000 claims 1
- ATHLCHSPHOTZSW-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-1H-benzimidazole-4-carboxamide Chemical compound OC1=CC=C(C2=C1NC(=N2)C=1SC=CC=1)C(=O)N ATHLCHSPHOTZSW-UHFFFAOYSA-N 0.000 claims 1
- KMTNZCAGMPTVOX-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxylic acid Chemical compound N1C=2C(C(=O)O)=CC=C(O)C=2N=C1C1=CC=CS1 KMTNZCAGMPTVOX-UHFFFAOYSA-N 0.000 claims 1
- NZBRUYFITVWYNU-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-n-(2-thiophen-2-ylethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=CC=CS1 NZBRUYFITVWYNU-UHFFFAOYSA-N 0.000 claims 1
- VDTJTBXXNGFVFO-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-n-[2-[5-(trifluoromethyl)pyridin-2-yl]oxyethyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCOC1=CC=C(C(F)(F)F)C=N1 VDTJTBXXNGFVFO-UHFFFAOYSA-N 0.000 claims 1
- BMDGRFFORKPVDW-UHFFFAOYSA-N 7-hydroxy-n-(1,3-thiazol-2-yl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NC1=NC=CS1 BMDGRFFORKPVDW-UHFFFAOYSA-N 0.000 claims 1
- RQWPXWYHCDTLCQ-UHFFFAOYSA-N 7-hydroxy-n-(3-imidazol-1-ylpropyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCCN1C=CN=C1 RQWPXWYHCDTLCQ-UHFFFAOYSA-N 0.000 claims 1
- XUYLZESPGHLNED-LLVKDONJSA-N 7-hydroxy-n-[(2r)-1-hydroxy-3-(1h-imidazol-5-yl)propan-2-yl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C([C@H](CO)NC(=O)C=1C=2N=C(NC=2C(O)=CC=1)C=1SC=CC=1)C1=CNC=N1 XUYLZESPGHLNED-LLVKDONJSA-N 0.000 claims 1
- AOUOLQCMFOELTQ-CYBMUJFWSA-N 7-hydroxy-n-[(2s)-1-hydroxy-3,3-dimethylbutan-2-yl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)N[C@H](CO)C(C)(C)C)=CC=C(O)C=2NC=1C1=CC=CS1 AOUOLQCMFOELTQ-CYBMUJFWSA-N 0.000 claims 1
- ZQTVQAUSCZFRGE-AWEZNQCLSA-N 7-hydroxy-n-[(2s)-1-hydroxy-3-phenylpropan-2-yl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C([C@@H](CO)NC(=O)C=1C=2N=C(NC=2C(O)=CC=1)C=1SC=CC=1)C1=CC=CC=C1 ZQTVQAUSCZFRGE-AWEZNQCLSA-N 0.000 claims 1
- KPMGOOQJFZUQKN-UHFFFAOYSA-N 7-hydroxy-n-[(4-sulfamoylphenyl)methyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 KPMGOOQJFZUQKN-UHFFFAOYSA-N 0.000 claims 1
- BTRMVOSUMNXHFE-UHFFFAOYSA-N 7-hydroxy-n-[2-(1h-imidazol-2-yl)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=NC=CN1 BTRMVOSUMNXHFE-UHFFFAOYSA-N 0.000 claims 1
- KIBQEHLLMWSGFX-UHFFFAOYSA-N 7-hydroxy-n-[2-(1h-imidazol-5-yl)ethyl]-1h-indole-3-carboxamide Chemical compound C=1NC=2C(O)=CC=CC=2C=1C(=O)NCCC1=CN=CN1 KIBQEHLLMWSGFX-UHFFFAOYSA-N 0.000 claims 1
- UHNVSGAVJLZCOT-UHFFFAOYSA-N 7-hydroxy-n-[2-(1h-imidazol-5-yl)ethyl]-2-thiophen-2-yl-3h-benzimidazole-5-carboxamide Chemical compound N1C=2C(O)=CC(C(=O)NCCC=3NC=NC=3)=CC=2N=C1C1=CC=CS1 UHNVSGAVJLZCOT-UHFFFAOYSA-N 0.000 claims 1
- YBFGBABPODCQNN-UHFFFAOYSA-N 7-hydroxy-n-[2-(3-methylimidazol-4-yl)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound CN1C=NC=C1CCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 YBFGBABPODCQNN-UHFFFAOYSA-N 0.000 claims 1
- MROBEFRBDYTTSK-UHFFFAOYSA-N 7-hydroxy-n-[2-(4-hydroxyphenyl)ethyl]-2-phenyl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C=1C=CC=CC=1)=N2 MROBEFRBDYTTSK-UHFFFAOYSA-N 0.000 claims 1
- PMQBYSMSFGQXEX-UHFFFAOYSA-N 7-hydroxy-n-[2-(4-hydroxyphenyl)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 PMQBYSMSFGQXEX-UHFFFAOYSA-N 0.000 claims 1
- BBIVHOWFUCOWKO-UHFFFAOYSA-N 7-hydroxy-n-[2-(4-nitrophenoxy)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCOC1=CC=C([N+]([O-])=O)C=C1 BBIVHOWFUCOWKO-UHFFFAOYSA-N 0.000 claims 1
- FLPCFXRGUFUVHJ-UHFFFAOYSA-N 7-hydroxy-n-[2-(4-sulfamoylphenyl)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 FLPCFXRGUFUVHJ-UHFFFAOYSA-N 0.000 claims 1
- BSGKOICCPIZSNX-UHFFFAOYSA-N 7-hydroxy-n-[2-(pyridin-2-ylamino)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNC1=CC=CC=N1 BSGKOICCPIZSNX-UHFFFAOYSA-N 0.000 claims 1
- FUGLJOSMSYGJAU-UHFFFAOYSA-N 7-hydroxy-n-[2-(pyridin-4-ylsulfonylamino)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNS(=O)(=O)C1=CC=NC=C1 FUGLJOSMSYGJAU-UHFFFAOYSA-N 0.000 claims 1
- YDRDTJACXJKVCD-UHFFFAOYSA-N 7-hydroxy-n-[2-[(4-methylbenzoyl)amino]ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C(=O)NCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 YDRDTJACXJKVCD-UHFFFAOYSA-N 0.000 claims 1
- CTAQQUCNSORLGC-UHFFFAOYSA-N 7-hydroxy-n-[2-[4-[(4-methylphenyl)sulfonylamino]phenoxy]ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1OCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 CTAQQUCNSORLGC-UHFFFAOYSA-N 0.000 claims 1
- LOVNJIKQQJSSDK-UHFFFAOYSA-N 7-hydroxy-n-[3-(2-hydroxyethylamino)propyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCCNCCO)=CC=C(O)C=2NC=1C1=CC=CS1 LOVNJIKQQJSSDK-UHFFFAOYSA-N 0.000 claims 1
- PZYYLNDOXCOICP-UHFFFAOYSA-N 7-hydroxy-n-[3-(5-oxo-1,4-dihydropyrazol-4-yl)propyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCCC1C=NNC1=O PZYYLNDOXCOICP-UHFFFAOYSA-N 0.000 claims 1
- QJHCQFHTMOZFOW-UHFFFAOYSA-N 7-hydroxy-n-[3-(propan-2-ylamino)propyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCCNC(C)C)=CC=C(O)C=2NC=1C1=CC=CS1 QJHCQFHTMOZFOW-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UQBQUPKEQYLNEP-KRWDZBQOSA-N methyl (2s)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]-3-(1h-indol-3-yl)propanoate Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)OC)C(=O)C(C=1N=2)=CC=C(O)C=1NC=2C1=CC=CS1 UQBQUPKEQYLNEP-KRWDZBQOSA-N 0.000 claims 1
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 1
- SIPPUXPIJXLNKR-UHFFFAOYSA-N methyl 3-(4-hydroxyphenyl)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]propanoate Chemical compound C=1C=C(O)C=2NC(C=3SC=CC=3)=NC=2C=1C(=O)NC(C(=O)OC)CC1=CC=C(O)C=C1 SIPPUXPIJXLNKR-UHFFFAOYSA-N 0.000 claims 1
- NCFOCOFBHNWJDC-UHFFFAOYSA-N methyl 3-hydroxy-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]propanoate Chemical compound N=1C=2C(C(=O)NC(CO)C(=O)OC)=CC=C(O)C=2NC=1C1=CC=CS1 NCFOCOFBHNWJDC-UHFFFAOYSA-N 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- HZQOAXBFUCEICD-UHFFFAOYSA-N n-(2-acetamidoethyl)-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCNC(=O)C)=CC=C(O)C=2NC=1C1=CC=CS1 HZQOAXBFUCEICD-UHFFFAOYSA-N 0.000 claims 1
- COKWCLRPCPQRHW-UHFFFAOYSA-N n-(2-cyclopropyl-7-hydroxy-1h-benzimidazol-4-yl)-2-(4-hydroxyphenyl)acetamide Chemical compound C1=CC(O)=CC=C1CC(=O)NC1=CC=C(O)C2=C1N=C(C1CC1)N2 COKWCLRPCPQRHW-UHFFFAOYSA-N 0.000 claims 1
- MVIYVSVLUFCKPM-UHFFFAOYSA-N n-(7-hydroxy-2-thiophen-2-yl-1h-benzimidazol-4-yl)-3-(1h-imidazol-5-yl)propanamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1NC(=O)CCC1=CN=CN1 MVIYVSVLUFCKPM-UHFFFAOYSA-N 0.000 claims 1
- KAXYSAVZDDUQAY-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCC1=CC=C(F)C=C1F KAXYSAVZDDUQAY-UHFFFAOYSA-N 0.000 claims 1
- IOOARBMSXOAWLS-UHFFFAOYSA-N n-[(3,4-dihydroxyphenyl)methyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=C(O)C(O)=CC=C1CNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 IOOARBMSXOAWLS-UHFFFAOYSA-N 0.000 claims 1
- NBKMAQQGBPQUAH-UHFFFAOYSA-N n-[2-(3,4-dihydroxyphenyl)ethyl]-2-(furan-2-yl)-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1=C(O)C(O)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1N=C(C=1OC=CC=1)N2 NBKMAQQGBPQUAH-UHFFFAOYSA-N 0.000 claims 1
- PAPUOZOKUQXUCV-UHFFFAOYSA-N n-[2-(3,5-dimethyl-1,2-oxazol-4-yl)ethyl]-2-(furan-2-yl)-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound CC1=NOC(C)=C1CCNC(=O)C1=CC=C(O)C2=C1N=C(C=1OC=CC=1)N2 PAPUOZOKUQXUCV-UHFFFAOYSA-N 0.000 claims 1
- QSMNQEMSVXJRQS-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-7-hydroxy-2-phenyl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C=1C=CC=CC=1)=N2 QSMNQEMSVXJRQS-UHFFFAOYSA-N 0.000 claims 1
- VDMPWEXEHQWQKM-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=CC=C(F)C=C1 VDMPWEXEHQWQKM-UHFFFAOYSA-N 0.000 claims 1
- BDRBZSPAJPBMKA-UHFFFAOYSA-N n-[2-(5-carbamoylpyridin-2-yl)oxyethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1OCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 BDRBZSPAJPBMKA-UHFFFAOYSA-N 0.000 claims 1
- PNYYRFDFEXVEPN-UHFFFAOYSA-N n-[2-(benzenesulfonamido)ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNS(=O)(=O)C1=CC=CC=C1 PNYYRFDFEXVEPN-UHFFFAOYSA-N 0.000 claims 1
- VSWOMRSVSRDHTQ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCN(C)C)=CC=C(O)C=2NC=1C1=CC=CS1 VSWOMRSVSRDHTQ-UHFFFAOYSA-N 0.000 claims 1
- JOHGYBMIJBITFP-UHFFFAOYSA-N n-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNS(=O)(=O)C1=CC=C(Cl)C=C1 JOHGYBMIJBITFP-UHFFFAOYSA-N 0.000 claims 1
- NGQAEUFCTRTCCT-UHFFFAOYSA-N n-[2-[(5-acetamidopyridin-2-yl)amino]ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N1=CC(NC(=O)C)=CC=C1NCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 NGQAEUFCTRTCCT-UHFFFAOYSA-N 0.000 claims 1
- DWOUPRLHBBTUHD-UHFFFAOYSA-N n-[2-hydroxy-5-[2-(1h-imidazol-5-yl)ethylcarbamoyl]phenyl]thiophene-2-carboxamide Chemical compound OC1=CC=C(C(=O)NCCC=2NC=NC=2)C=C1NC(=O)C1=CC=CS1 DWOUPRLHBBTUHD-UHFFFAOYSA-N 0.000 claims 1
- HCDYZIZXEZAMPG-UHFFFAOYSA-N n-[5-hydroxy-2-(piperidin-3-ylcarbamoyl)phenyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NC1=CC(O)=CC=C1C(=O)NC1CCCNC1 HCDYZIZXEZAMPG-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8477008P | 2008-07-30 | 2008-07-30 | |
| US61/084,770 | 2008-07-30 |
Publications (1)
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|---|---|
| RU2011107227A true RU2011107227A (ru) | 2012-09-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011107227/13A RU2011107227A (ru) | 2008-07-30 | 2009-07-30 | Бензоимидазольные производные и ингибиторы гликоген-синтаза-киназы-3 бета, содержащие такие производные |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20110190351A1 (https=) |
| EP (1) | EP2309855A4 (https=) |
| JP (1) | JP2011529903A (https=) |
| KR (1) | KR20110040958A (https=) |
| CN (1) | CN102170785A (https=) |
| AU (1) | AU2009276548A1 (https=) |
| BR (1) | BRPI0916726A2 (https=) |
| CA (1) | CA2732280A1 (https=) |
| CO (1) | CO6351688A2 (https=) |
| IL (1) | IL210863A0 (https=) |
| MX (1) | MX2011001170A (https=) |
| RU (1) | RU2011107227A (https=) |
| WO (1) | WO2010014794A1 (https=) |
| ZA (1) | ZA201101160B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009158118A2 (en) | 2008-05-30 | 2009-12-30 | University Of Notre Dame Du Lac | Anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria |
| CN101619058A (zh) * | 2009-01-08 | 2010-01-06 | 上海交通大学 | 一种苯并咪唑-4-酰胺型衍生物 |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| PE20161064A1 (es) * | 2013-12-12 | 2016-10-28 | Univ Tsukuba | Derivado de sulfonamida o sales de adicion de acido farmaceuticamente aceptables del mismo |
| CN105461722B (zh) * | 2014-09-04 | 2019-05-10 | 欣凯医药化工中间体（上海）有限公司 | 一种脱氮嘌呤类化合物及其衍生物及其制备方法和应用 |
| WO2016133160A1 (ja) * | 2015-02-19 | 2016-08-25 | 国立大学法人筑波大学 | スルホンアミド誘導体またはその薬学的に許容される酸付加塩 |
| AU2021359129A1 (en) * | 2020-10-16 | 2023-06-01 | Proxygen Gmbh | Heterocyclic cullin ring ubiquitin ligase compounds and uses thereof |
| WO2024014851A1 (ko) * | 2022-07-12 | 2024-01-18 | 주식회사 넥스트젠바이오사이언스 | Hif-1 단백질 억제제로서의 신규한 퓨린 유도체 화합물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0178413A1 (en) * | 1984-08-17 | 1986-04-23 | Beecham Group Plc | Benzimidazoles |
| FR2699816B1 (fr) * | 1992-12-30 | 1995-03-03 | Oreal | Compositions tinctoriales pour fibres kératiniques à base de paraphénylènediamines, de métaphénylènediamines et de dérivés du benzimidazole, et procédé de teinture les mettant en Óoeuvre. |
| US7064215B2 (en) * | 2001-07-03 | 2006-06-20 | Chiron Corporation | Indazole benzimidazole compounds |
| WO2003066629A2 (en) * | 2002-02-06 | 2003-08-14 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds useful as inhibitors of gsk-3 |
| KR100791252B1 (ko) * | 2003-01-23 | 2008-01-03 | 크리스탈지노믹스(주) | 글리코겐 합성효소 키나아제 3β 활성 억제제, 이의제조방법 및 이를 유효성분으로 함유하는 약학 조성물 |
| BRPI0919977A2 (pt) * | 2008-10-30 | 2015-08-25 | Oncotherapy Science Inc | Derivados de 7-hidróxi-benzoimidazol-4-il-metanona e inibidores de pbk contendo os mesmos |
| JP2012509249A (ja) * | 2008-11-20 | 2012-04-19 | オンコセラピー・サイエンス株式会社 | ７−ヒドロキシ−ベンゾイミダゾール−４−イル−メタノン誘導体を含むグリコーゲン合成酵素キナーゼ−３ベータ阻害剤 |
-
2009
- 2009-07-30 AU AU2009276548A patent/AU2009276548A1/en not_active Withdrawn
- 2009-07-30 WO PCT/US2009/052225 patent/WO2010014794A1/en not_active Ceased
- 2009-07-30 CN CN2009801387112A patent/CN102170785A/zh not_active Withdrawn
- 2009-07-30 BR BRPI0916726A patent/BRPI0916726A2/pt not_active IP Right Cessation
- 2009-07-30 JP JP2011521313A patent/JP2011529903A/ja not_active Withdrawn
- 2009-07-30 MX MX2011001170A patent/MX2011001170A/es unknown
- 2009-07-30 CA CA2732280A patent/CA2732280A1/en not_active Abandoned
- 2009-07-30 EP EP09803582A patent/EP2309855A4/en active Pending
- 2009-07-30 KR KR1020117004602A patent/KR20110040958A/ko not_active Withdrawn
- 2009-07-30 US US13/056,591 patent/US20110190351A1/en not_active Abandoned
- 2009-07-30 RU RU2011107227/13A patent/RU2011107227A/ru not_active Application Discontinuation
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2011
- 2011-01-25 IL IL210863A patent/IL210863A0/en unknown
- 2011-02-08 CO CO11014386A patent/CO6351688A2/es not_active Application Discontinuation
- 2011-02-14 ZA ZA2011/01160A patent/ZA201101160B/en unknown
Also Published As
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|---|---|
| JP2011529903A (ja) | 2011-12-15 |
| ZA201101160B (en) | 2011-10-26 |
| CN102170785A (zh) | 2011-08-31 |
| MX2011001170A (es) | 2011-04-05 |
| US20110190351A1 (en) | 2011-08-04 |
| IL210863A0 (en) | 2011-04-28 |
| KR20110040958A (ko) | 2011-04-20 |
| CO6351688A2 (es) | 2011-12-20 |
| EP2309855A4 (en) | 2012-06-27 |
| EP2309855A1 (en) | 2011-04-20 |
| WO2010014794A1 (en) | 2010-02-04 |
| BRPI0916726A2 (pt) | 2017-07-04 |
| CA2732280A1 (en) | 2010-02-04 |
| AU2009276548A1 (en) | 2010-02-04 |
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