KR20110040958A - 벤조이미다졸 유도체 및 이를 유효성분으로 함유하는 글라이코겐 합성 카이네이즈-3 베타 저해제 - Google Patents

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Publication number

KR20110040958A

KR20110040958A KR1020117004602A KR20117004602A KR20110040958A KR 20110040958 A KR20110040958 A KR 20110040958A KR 1020117004602 A KR1020117004602 A KR 1020117004602A KR 20117004602 A KR20117004602 A KR 20117004602A KR 20110040958 A KR20110040958 A KR 20110040958A

Authority

KR

South Korea

Prior art keywords

benzo

hydroxy

imidazole

thiophen

carboxamide

Prior art date

2008-07-30

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Withdrawn

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• 239000003112 inhibitor Substances 0.000 title claims abstract description 10
• 229920002527 Glycogen Polymers 0.000 title claims abstract description 6
• 229940096919 glycogen Drugs 0.000 title claims abstract description 6
• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims 2
• 238000003786 synthesis reaction Methods 0.000 title abstract description 27
• 230000015572 biosynthetic process Effects 0.000 title abstract description 24
• 239000004480 active ingredient Substances 0.000 title description 6
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 256
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 136
• 125000003118 aryl group Chemical group 0.000 claims description 91
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 69
• 125000000623 heterocyclic group Chemical group 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 37
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• 238000002360 preparation method Methods 0.000 claims description 30
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 28
• 150000001408 amides Chemical group 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical class NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 claims description 17
• 150000004677 hydrates Chemical class 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 150000001412 amines Chemical class 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000000203 mixture Substances 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 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 12
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 10
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical group [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 10
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 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 description 9
• GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 claims description 8
• 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 7
• 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 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• UVKHHBRUBXLKTP-QPJJXVBHSA-N (e)-3-(1h-imidazol-5-yl)-n-(7-methoxy-2-thiophen-2-yl-1h-benzimidazol-4-yl)prop-2-enamide Chemical class C1=2N=C(C=3SC=CC=3)NC=2C(OC)=CC=C1NC(=O)\C=C\C1=CN=CN1 UVKHHBRUBXLKTP-QPJJXVBHSA-N 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• GVOUFPWUYJWQSK-UHFFFAOYSA-N Cyclofenil Chemical group C1=CC(OC(=O)C)=CC=C1C(C=1C=CC(OC(C)=O)=CC=1)=C1CCCCC1 GVOUFPWUYJWQSK-UHFFFAOYSA-N 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 229960002944 cyclofenil Drugs 0.000 claims description 5
• ZCKYOWGFRHAZIQ-UHFFFAOYSA-N dihydrourocanic acid Chemical compound OC(=O)CCC1=CNC=N1 ZCKYOWGFRHAZIQ-UHFFFAOYSA-N 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000004043 oxo group Chemical group O=* 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
• 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 4
• 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 description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 208000019695 Migraine disease Diseases 0.000 claims description 4
• 150000001409 amidines Chemical class 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 208000002173 dizziness Diseases 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 description 4
• 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 4
• 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 4
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
• 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 3
• WNVIEMRKZPPPOJ-UHFFFAOYSA-N 2-(1H-Indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C(C(O)=O)C)=CNC2=C1 WNVIEMRKZPPPOJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• GOPDFXUMARJJEA-UHFFFAOYSA-N amino(nitro)azanide Chemical compound N[N-][N+]([O-])=O GOPDFXUMARJJEA-UHFFFAOYSA-N 0.000 claims description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
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