JP2011529903A5 - - Google Patents
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- JP2011529903A5 JP2011529903A5 JP2011521313A JP2011521313A JP2011529903A5 JP 2011529903 A5 JP2011529903 A5 JP 2011529903A5 JP 2011521313 A JP2011521313 A JP 2011521313A JP 2011521313 A JP2011521313 A JP 2011521313A JP 2011529903 A5 JP2011529903 A5 JP 2011529903A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- benzo
- carboxamide
- imidazole
- thiophen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 40
- -1 nitro, amino Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 0.000 claims description 13
- 238000005859 coupling reaction Methods 0.000 claims description 13
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 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 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 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 description 4
- 150000001448 anilines Chemical class 0.000 claims description 4
- 150000001556 benzimidazoles Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 4
- HIZFNUNLIFFTSQ-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-[3-(5-oxo-1,4-dihydropyrazol-4-yl)propyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NCCCC1C=NNC1=O HIZFNUNLIFFTSQ-UHFFFAOYSA-N 0.000 claims description 3
- SUGCCDILQLTMOW-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-(4-hydroxyphenyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=C(O)C2=C1NC(C1CC1)=N2 SUGCCDILQLTMOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- HVIMPUISPMUNPS-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-[2-(4-sulfamoylphenyl)ethyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C1CC1)=N2 HVIMPUISPMUNPS-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- HHGDSAWNMROJTC-UHFFFAOYSA-N 2-cyclopropyl-n-[2-(4-fluorophenyl)ethyl]-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NCCC1=CC=C(F)C=C1 HHGDSAWNMROJTC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- JPQBWJWUGVSDBA-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC(O)=C2NC=1C1=CC=CS1 JPQBWJWUGVSDBA-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- TTYFZHGTFLFGDI-UHFFFAOYSA-N 7-hydroxy-n-[2-[[5-(methanesulfonamido)pyridin-2-yl]amino]ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N1=CC(NS(=O)(=O)C)=CC=C1NCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 TTYFZHGTFLFGDI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims description 2
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 206010026749 Mania Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
- 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 description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- CYEZNUPYHKNUEM-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2-cyclopentyl-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C1CCCC1)=N2 CYEZNUPYHKNUEM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 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 description 2
- 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 description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- QCQAZAFKSFCSIP-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-1h-benzimidazole-4-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=C(O)C=2NC=1C1=CC=CO1 QCQAZAFKSFCSIP-UHFFFAOYSA-N 0.000 description 2
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- 239000007821 HATU Substances 0.000 description 2
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 1
- QIEMOKUVCNROKE-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-[2-[(5-nitropyridin-2-yl)amino]ethyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNC1=CC=C([N+]([O-])=O)C=N1 QIEMOKUVCNROKE-UHFFFAOYSA-N 0.000 description 1
- ANXCBFTZWJXBSY-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-1h-benzimidazole-4-carboxylic acid Chemical compound N1C=2C(C(=O)O)=CC=C(O)C=2N=C1C1CC1 ANXCBFTZWJXBSY-UHFFFAOYSA-N 0.000 description 1
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- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 1
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- 0 C*(C)ICc1ccc(*)c2c1nc(*)[n]2 Chemical compound C*(C)ICc1ccc(*)c2c1nc(*)[n]2 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 238000005342 ion exchange Methods 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
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| PCT/US2009/052225 WO2010014794A1 (en) | 2008-07-30 | 2009-07-30 | Benzoimidazole derivatives and glycogen synthase kinase-3 beta inhibitors containing the same |
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| US8362268B2 (en) | 2008-05-30 | 2013-01-29 | 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 |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| 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 |
| US9815787B2 (en) * | 2013-12-12 | 2017-11-14 | University Of Tsukuba | Sulfonamide derivative or pharmaceutically acceptable acid addition salt thereof |
| 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 |
| US20240132485A1 (en) * | 2020-10-16 | 2024-04-25 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Heterocyclic cullin ring ubiquitin ligase compounds and uses thereof |
| KR20240008807A (ko) * | 2022-07-12 | 2024-01-19 | 주식회사 넥스트젠바이오사이언스 | Hif-1 단백질 억제제로서의 신규한 퓨린 유도체 화합물 |
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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 |
| RU2004126671A (ru) * | 2002-02-06 | 2005-04-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Гетероарилсоединения, полезные в качестве ингибиторов gsk-3 |
| JP2006515013A (ja) * | 2003-01-23 | 2006-05-18 | クリスタルジェノミクス、インコーポレイテッド | グリコーゲン合成酵素キナーゼ３β活性抑制剤、組成物及びその製造方法 |
| AU2009310310A1 (en) * | 2008-10-30 | 2010-05-06 | Oncotherapy Science, Inc. | 7-Hydroxy-benzoimidazole-4-yl-methanone Derivatives and PBK inhibitors containing the same |
| EP2358365A4 (en) * | 2008-11-20 | 2012-05-30 | Oncotherapy Science Inc | GLYCOGEN SYNTHASE KINASE 3 BETA HEMMER WITH 7-HYDROXY BENZOIMIDAZOLE-4-YL METHANONE DERIVATIVES |
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- 2009-07-30 MX MX2011001170A patent/MX2011001170A/es unknown
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- 2009-07-30 EP EP09803582A patent/EP2309855A4/en active Pending
- 2009-07-30 US US13/056,591 patent/US20110190351A1/en not_active Abandoned
- 2009-07-30 WO PCT/US2009/052225 patent/WO2010014794A1/en not_active Ceased
- 2009-07-30 CA CA2732280A patent/CA2732280A1/en not_active Abandoned
- 2009-07-30 BR BRPI0916726A patent/BRPI0916726A2/pt not_active IP Right Cessation
- 2009-07-30 AU AU2009276548A patent/AU2009276548A1/en not_active Withdrawn
- 2009-07-30 CN CN2009801387112A patent/CN102170785A/zh not_active Withdrawn
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2011
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- 2011-02-08 CO CO11014386A patent/CO6351688A2/es not_active Application Discontinuation
- 2011-02-14 ZA ZA2011/01160A patent/ZA201101160B/en unknown
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