NO327008B1 - Substituerte benzimidazolforbindelser og deres anvendelse for fremstilling av medikamenter for behandling av cancer - Google Patents

Info

Publication number

NO327008B1

NO327008B1 NO20041214A NO20041214A NO327008B1 NO 327008 B1 NO327008 B1 NO 327008B1 NO 20041214 A NO20041214 A NO 20041214A NO 20041214 A NO20041214 A NO 20041214A NO 327008 B1 NO327008 B1 NO 327008B1

Authority

NO

Norway

Prior art keywords

ester

benzoimidazol

benzenesulfonic acid

amino

ureido

Prior art date

2001-09-26

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• 206010028980 Neoplasm Diseases 0.000 title claims description 10
• 201000011510 cancer Diseases 0.000 title claims description 8
• 239000003814 drug Substances 0.000 title claims description 8
• 229940079593 drug Drugs 0.000 title description 7
• 238000004519 manufacturing process Methods 0.000 title description 3
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 121
• -1 acyl derivative halogen Chemical class 0.000 claims description 90
• 238000002360 preparation method Methods 0.000 claims description 66
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 125000002252 acyl group Chemical group 0.000 claims description 16
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• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
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• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
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• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 13
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• 150000001412 amines Chemical class 0.000 description 13
• 238000006243 chemical reaction Methods 0.000 description 13
• 150000002148 esters Chemical class 0.000 description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
• 239000000284 extract Substances 0.000 description 12
• 239000000203 mixture Substances 0.000 description 12
• 238000000746 purification Methods 0.000 description 12
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
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• XPPKIQZLYLUAAY-UHFFFAOYSA-N C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)OC(C=C1)=CC=C1C1=NC=CN1 Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)OC(C=C1)=CC=C1C1=NC=CN1 XPPKIQZLYLUAAY-UHFFFAOYSA-N 0.000 description 9
• 108091007914 CDKs Proteins 0.000 description 9
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• XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 8
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
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• CLDVDAKGGKTXBY-UHFFFAOYSA-N [2-(cyclobutylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2NC=1NC(=O)NC1CCC1 CLDVDAKGGKTXBY-UHFFFAOYSA-N 0.000 description 1
• YXFXMBWOTKBZDE-UHFFFAOYSA-N [2-(cyclobutylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CCC1 YXFXMBWOTKBZDE-UHFFFAOYSA-N 0.000 description 1
• GFCLORKUTLQHSZ-UHFFFAOYSA-N [2-(cyclohexylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2NC=1NC(=O)NC1CCCCC1 GFCLORKUTLQHSZ-UHFFFAOYSA-N 0.000 description 1
• YUZLMGPKRSRJPV-UHFFFAOYSA-N [2-(cyclohexylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CCCCC1 YUZLMGPKRSRJPV-UHFFFAOYSA-N 0.000 description 1
• YDJOGUCSJKOCJV-UHFFFAOYSA-N [2-(cyclopentylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CCCC1 YDJOGUCSJKOCJV-UHFFFAOYSA-N 0.000 description 1
• FFJQHPRACFEMSA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1,3-dihydroxypropan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(CO)CO)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 FFJQHPRACFEMSA-UHFFFAOYSA-N 0.000 description 1
• XDWHKQHHYFHSGB-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1-hydroxypentan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(CO)CCC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 XDWHKQHHYFHSGB-UHFFFAOYSA-N 0.000 description 1
• UDBZMJNUEXYSPY-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1-methoxypropan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(C)COC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 UDBZMJNUEXYSPY-UHFFFAOYSA-N 0.000 description 1
• PLDMGTKGLSCYSN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1-phenoxypropan-2-ylamino)benzenesulfonate Chemical compound C=1C=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=CC=1NC(C)COC1=CC=CC=C1 PLDMGTKGLSCYSN-UHFFFAOYSA-N 0.000 description 1
• VRNAWQALSVDBIS-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(1h-indol-5-ylamino)benzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(NC=4C=C5C=CNC5=CC=4)=CC=3)=CC=C2NC=1NC(=O)C1CC1 VRNAWQALSVDBIS-UHFFFAOYSA-N 0.000 description 1
• FJYDVJAWVPGZBN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2,6-dimethylmorpholin-4-yl)benzenesulfonate Chemical compound C1C(C)OC(C)CN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 FJYDVJAWVPGZBN-UHFFFAOYSA-N 0.000 description 1
• PFJRCSJKCZGTJD-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2-pyridin-3-ylpyrrolidin-1-yl)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1CCCC1C1=CC=CN=C1 PFJRCSJKCZGTJD-UHFFFAOYSA-N 0.000 description 1
• VAPSQUPVXFWSLT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrol-1-ylethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCN1C=CC=C1 VAPSQUPVXFWSLT-UHFFFAOYSA-N 0.000 description 1
• QZUULHZMVYXUAW-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrolidin-1-ylethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCN1CCCC1 QZUULHZMVYXUAW-UHFFFAOYSA-N 0.000 description 1
• YEBLKPKXNZLGPC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3,3-dimethylpiperidin-1-yl)benzenesulfonate Chemical compound C1C(C)(C)CCCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 YEBLKPKXNZLGPC-UHFFFAOYSA-N 0.000 description 1
• ZROBQSRBKZCBQY-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-hydroxypropylamino)benzenesulfonate Chemical compound C1=CC(NCCCO)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 ZROBQSRBKZCBQY-UHFFFAOYSA-N 0.000 description 1
• VYMWAUHDDMRDTN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-hydroxypyrrolidin-1-yl)benzenesulfonate Chemical compound C1C(O)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 VYMWAUHDDMRDTN-UHFFFAOYSA-N 0.000 description 1
• MBLDNXCADDCXQC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-imidazol-1-ylpropylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCN1C=CN=C1 MBLDNXCADDCXQC-UHFFFAOYSA-N 0.000 description 1
• WDZGXSLAMMBCCD-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(3-methoxypropylamino)benzenesulfonate Chemical compound C1=CC(NCCCOC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 WDZGXSLAMMBCCD-UHFFFAOYSA-N 0.000 description 1
• NLUJSSCPUCKCMT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-carbamoylpiperidin-1-yl)benzenesulfonate Chemical compound C1CC(C(=O)N)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 NLUJSSCPUCKCMT-UHFFFAOYSA-N 0.000 description 1
• AHINQIQMTISVIY-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-ethoxyanilino)benzenesulfonate Chemical compound C1=CC(OCC)=CC=C1NC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 AHINQIQMTISVIY-UHFFFAOYSA-N 0.000 description 1
• QIVWHSUAWZALKQ-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-hydroxypiperidin-1-yl)benzenesulfonate Chemical compound C1CC(O)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 QIVWHSUAWZALKQ-UHFFFAOYSA-N 0.000 description 1
• NFEQLQOSJOTIJR-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-methyl-1,4-diazepan-1-yl)benzenesulfonate Chemical compound C1CN(C)CCCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 NFEQLQOSJOTIJR-UHFFFAOYSA-N 0.000 description 1
• QWQLYXRARLJHOA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-pyridin-2-ylpiperazin-1-yl)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N(CC1)CCN1C1=CC=CC=N1 QWQLYXRARLJHOA-UHFFFAOYSA-N 0.000 description 1
• JGCLLRZTMZRDTO-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(4-pyrrolidin-1-ylbutylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCCN1CCCC1 JGCLLRZTMZRDTO-UHFFFAOYSA-N 0.000 description 1
• OPKNSCUJIMHDNI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 OPKNSCUJIMHDNI-UHFFFAOYSA-N 0.000 description 1
• VHJWBIRJHNLFOU-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(cyclopropylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NC1CC1 VHJWBIRJHNLFOU-UHFFFAOYSA-N 0.000 description 1
• HUMKESGNAGZKOJ-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(ethylamino)benzenesulfonate Chemical compound C1=CC(NCC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 HUMKESGNAGZKOJ-UHFFFAOYSA-N 0.000 description 1
• YOBXDGKEIPGGFA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(piperidin-4-ylmethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCC1CCNCC1 YOBXDGKEIPGGFA-UHFFFAOYSA-N 0.000 description 1
• JDXZNWOXUYIPFE-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(propylamino)benzenesulfonate Chemical compound C1=CC(NCCC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 JDXZNWOXUYIPFE-UHFFFAOYSA-N 0.000 description 1
• MYVXFGSVDLZEIT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-(pyridin-2-ylmethylamino)benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCC1=CC=CC=N1 MYVXFGSVDLZEIT-UHFFFAOYSA-N 0.000 description 1
• FCESKQRBABHKAQ-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(1-hydroxy-2-methylpropan-2-yl)amino]benzenesulfonate Chemical compound C1=CC(NC(C)(CO)C)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 FCESKQRBABHKAQ-UHFFFAOYSA-N 0.000 description 1
• KKMXZQHBPCIYKM-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(2-hydroxycyclohexyl)amino]benzenesulfonate Chemical compound OC1CCCCC1NC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 KKMXZQHBPCIYKM-UHFFFAOYSA-N 0.000 description 1
• SWYGEDQXYMNJGV-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(2-oxo-1h-pyrimidin-6-yl)amino]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N=C1C=CNC(=O)N1 SWYGEDQXYMNJGV-UHFFFAOYSA-N 0.000 description 1
• ORIULQHLBJENIA-LJQANCHMSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(2r)-2-carbamoylpyrrolidin-1-yl]benzenesulfonate Chemical compound NC(=O)[C@H]1CCCN1C1=CC=C(S(=O)(=O)OC=2C=C3NC(NC(=O)C4CC4)=NC3=CC=2)C=C1 ORIULQHLBJENIA-LJQANCHMSA-N 0.000 description 1
• RATTYHJTCBOZTI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(3-methoxyphenyl)methylamino]benzenesulfonate Chemical compound COC1=CC=CC(CNC=2C=CC(=CC=2)S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)=C1 RATTYHJTCBOZTI-UHFFFAOYSA-N 0.000 description 1
• RINJVWDFIQVUHG-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(3-methyl-5-oxo-4h-imidazol-2-yl)amino]benzenesulfonate Chemical compound CN1CC(=O)NC1=NC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 RINJVWDFIQVUHG-UHFFFAOYSA-N 0.000 description 1
• OTXDRISAQBMHCA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(4-acetamidophenyl)methylamino]benzenesulfonate Chemical compound C1=CC(NC(=O)C)=CC=C1CNC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 OTXDRISAQBMHCA-UHFFFAOYSA-N 0.000 description 1
• GXYJIMAKKNVOGI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[(4-aminophenyl)methylamino]benzenesulfonate Chemical compound C1=CC(N)=CC=C1CNC1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 GXYJIMAKKNVOGI-UHFFFAOYSA-N 0.000 description 1
• FFQYILYIFSJMTP-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[1-(dimethylamino)propan-2-ylamino]benzenesulfonate Chemical compound C1=CC(NC(CN(C)C)C)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 FFQYILYIFSJMTP-UHFFFAOYSA-N 0.000 description 1
• AFNKUONEDBNDTC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[2-(2-hydroxyethyl)piperidin-1-yl]benzenesulfonate Chemical compound OCCC1CCCCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 AFNKUONEDBNDTC-UHFFFAOYSA-N 0.000 description 1
• FIWOANRBCSZVGA-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[2-(n-ethyl-3-methylanilino)ethylamino]benzenesulfonate Chemical compound C=1C=CC(C)=CC=1N(CC)CCNC(C=C1)=CC=C1S(=O)(=O)OC(C=C1N=2)=CC=C1NC=2NC(=O)C1CC1 FIWOANRBCSZVGA-UHFFFAOYSA-N 0.000 description 1
• DCGHGPXJVGUPAH-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[2-(propan-2-ylamino)ethylamino]benzenesulfonate Chemical compound C1=CC(NCCNC(C)C)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 DCGHGPXJVGUPAH-UHFFFAOYSA-N 0.000 description 1
• NEPMGWPVRJSHTI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[3-(2-hydroxyethylamino)propylamino]benzenesulfonate Chemical compound C1=CC(NCCCNCCO)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 NEPMGWPVRJSHTI-UHFFFAOYSA-N 0.000 description 1
• NKLQUZQUQJWQMU-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[3-(2-oxopyrrolidin-1-yl)propylamino]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCN1CCCC1=O NKLQUZQUQJWQMU-UHFFFAOYSA-N 0.000 description 1
• APXZULWAKQCVOC-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[3-(cyclohexylamino)propylamino]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NCCCNC1CCCCC1 APXZULWAKQCVOC-UHFFFAOYSA-N 0.000 description 1
• GJNAJVVYAYRDSK-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(2-hydroxyethyl)piperidin-1-yl]benzenesulfonate Chemical compound C1CC(CCO)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 GJNAJVVYAYRDSK-UHFFFAOYSA-N 0.000 description 1
• AWNKJFMDDPMKNR-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(2-methoxyethyl)piperazin-1-yl]benzenesulfonate Chemical compound C1CN(CCOC)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 AWNKJFMDDPMKNR-UHFFFAOYSA-N 0.000 description 1
• NLIPFPSNKGUAPD-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(3-pyrrolidin-1-ylpropyl)-1,4-diazepan-1-yl]benzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N(CC1)CCCN1CCCN1CCCC1 NLIPFPSNKGUAPD-UHFFFAOYSA-N 0.000 description 1
• IZGOPDFWYLNFQN-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-(4-methoxyphenyl)piperazin-1-yl]benzenesulfonate Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(=CC=2)S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)CC1 IZGOPDFWYLNFQN-UHFFFAOYSA-N 0.000 description 1
• BXIHCMSBVOKFOT-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]benzenesulfonate Chemical compound C1CN(CCOCCO)CCN1C1=CC=C(S(=O)(=O)OC=2C=C3N=C(NC(=O)C4CC4)NC3=CC=2)C=C1 BXIHCMSBVOKFOT-UHFFFAOYSA-N 0.000 description 1
• LTYYWVKVQOGCKI-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-[ethyl(2-hydroxyethyl)amino]benzenesulfonate Chemical compound C1=CC(N(CCO)CC)=CC=C1S(=O)(=O)OC1=CC=C(NC(NC(=O)C2CC2)=N2)C2=C1 LTYYWVKVQOGCKI-UHFFFAOYSA-N 0.000 description 1
• UPBREWNUGOONGM-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-piperidin-1-ylbenzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1CCCCC1 UPBREWNUGOONGM-UHFFFAOYSA-N 0.000 description 1
• RFNWBOWIQVSXIH-UHFFFAOYSA-N [2-(cyclopropanecarbonylamino)-3h-benzimidazol-5-yl] 4-pyrrolidin-1-ylbenzenesulfonate Chemical compound C1CC1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1CCCC1 RFNWBOWIQVSXIH-UHFFFAOYSA-N 0.000 description 1
• STUIVRBECMQFAW-UHFFFAOYSA-N [2-(cyclopropylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NC1CC1 STUIVRBECMQFAW-UHFFFAOYSA-N 0.000 description 1
• XEYKORZTJNMMHL-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(1-hydroxypropan-2-ylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC)=NC2=CC=1OS(=O)(=O)C1=CC=C(NC(C)CO)C=C1 XEYKORZTJNMMHL-UHFFFAOYSA-N 0.000 description 1
• KUZDGERFXOLCLO-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-hydroxypropylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)NCC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCC(C)O)C=C1 KUZDGERFXOLCLO-UHFFFAOYSA-N 0.000 description 1
• MNBOIFLEHYOHJQ-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrolidin-1-ylethylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)NCC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NCCN1CCCC1 MNBOIFLEHYOHJQ-UHFFFAOYSA-N 0.000 description 1
• YRZAVZWEETYTOV-UHFFFAOYSA-N [2-(ethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 YRZAVZWEETYTOV-UHFFFAOYSA-N 0.000 description 1
• KXADNXKCXRMIGA-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 2-(trifluoromethoxy)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC=C1OC(F)(F)F KXADNXKCXRMIGA-UHFFFAOYSA-N 0.000 description 1
• PICHWOYICTXINJ-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 2-cyanobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC=C1C#N PICHWOYICTXINJ-UHFFFAOYSA-N 0.000 description 1
• JORKTWPMXGCOBT-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3,4-dimethoxybenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=C(OC)C(OC)=C1 JORKTWPMXGCOBT-UHFFFAOYSA-N 0.000 description 1
• RUAGAOSXCZWMPM-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-(trifluoromethyl)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 RUAGAOSXCZWMPM-UHFFFAOYSA-N 0.000 description 1
• NHGCIPXCUDYTRT-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-fluorobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC(F)=C1 NHGCIPXCUDYTRT-UHFFFAOYSA-N 0.000 description 1
• FNBMBWQKCICZRF-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-methoxybenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC(OC)=C1 FNBMBWQKCICZRF-UHFFFAOYSA-N 0.000 description 1
• ZMPMOWZUCZBODC-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-nitrobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ZMPMOWZUCZBODC-UHFFFAOYSA-N 0.000 description 1
• XITQHVNEMZLDBH-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(1-hydroxybutan-2-ylamino)benzenesulfonate Chemical compound C1=CC(NC(CO)CC)=CC=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)OC)N2)C2=C1 XITQHVNEMZLDBH-UHFFFAOYSA-N 0.000 description 1
• OIAKSBJHPHNWRB-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-hydroxypropylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCC(C)O)C=C1 OIAKSBJHPHNWRB-UHFFFAOYSA-N 0.000 description 1
• XPPCCEIOFXUHFO-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-morpholin-4-ylethylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NCCN1CCOCC1 XPPCCEIOFXUHFO-UHFFFAOYSA-N 0.000 description 1
• OGKUOEQBZWVSFP-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-phenylethylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NCCC1=CC=CC=C1 OGKUOEQBZWVSFP-UHFFFAOYSA-N 0.000 description 1
• WPCAVSDTMWHNFX-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(2-piperidin-1-ylethoxy)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1OCCN1CCCCC1 WPCAVSDTMWHNFX-UHFFFAOYSA-N 0.000 description 1
• AKZQLUZWOLDHLS-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(3-methoxypropylamino)benzenesulfonate Chemical compound C1=CC(NCCCOC)=CC=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)OC)N2)C2=C1 AKZQLUZWOLDHLS-UHFFFAOYSA-N 0.000 description 1
• CHOKDGKAHJVMFA-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(4-hydroxybutylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCCCCO)C=C1 CHOKDGKAHJVMFA-UHFFFAOYSA-N 0.000 description 1
• DOGUOCQFHURBER-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(benzylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NCC1=CC=CC=C1 DOGUOCQFHURBER-UHFFFAOYSA-N 0.000 description 1
• XFOBPVWHPPELOM-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-(oxolan-2-ylmethylamino)benzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1NCC1CCCO1 XFOBPVWHPPELOM-UHFFFAOYSA-N 0.000 description 1
• AQQNMQKAEUNTIJ-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-cyanobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=C(C#N)C=C1 AQQNMQKAEUNTIJ-UHFFFAOYSA-N 0.000 description 1
• MIKOSCZYCTZEPX-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 MIKOSCZYCTZEPX-UHFFFAOYSA-N 0.000 description 1
• SVJQZCKFEYSCAJ-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] thiophene-2-sulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CS1 SVJQZCKFEYSCAJ-UHFFFAOYSA-N 0.000 description 1
• JDEZNSQNUBFQJV-UHFFFAOYSA-N [2-(methylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(oxolan-2-ylmethylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NCC1CCCO1 JDEZNSQNUBFQJV-UHFFFAOYSA-N 0.000 description 1
• RCSNVQISJVFESH-UHFFFAOYSA-N [2-(phenylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=CC=CC=1NC(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 RCSNVQISJVFESH-UHFFFAOYSA-N 0.000 description 1
• WOLFLKNNESBXNR-UHFFFAOYSA-N [2-(phenylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=CC=CC=1NC(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 WOLFLKNNESBXNR-UHFFFAOYSA-N 0.000 description 1
• HFWZMMIGTZWZMR-UHFFFAOYSA-N [2-(piperidin-4-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NCC1CCNCC1 HFWZMMIGTZWZMR-UHFFFAOYSA-N 0.000 description 1
• BCUMMTAPWHKYMM-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 2,6-difluorobenzenesulfonate Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)NCC=2N=CC=CC=2)N2)C2=C1 BCUMMTAPWHKYMM-UHFFFAOYSA-N 0.000 description 1
• VQCSIYWETLDDDZ-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-fluoroethylamino)benzenesulfonate Chemical compound C1=CC(NCCF)=CC=C1S(=O)(=O)OC1=CC=C(N=C(NC(=O)NCC=2N=CC=CC=2)N2)C2=C1 VQCSIYWETLDDDZ-UHFFFAOYSA-N 0.000 description 1
• UYTPJBJVOQCTPM-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-piperidin-1-ylethylamino)benzenesulfonate Chemical compound N=1C2=CC=C(OS(=O)(=O)C=3C=CC(NCCN4CCCCC4)=CC=3)C=C2NC=1NC(=O)NCC1=CC=CC=N1 UYTPJBJVOQCTPM-UHFFFAOYSA-N 0.000 description 1
• MMOCLWWJYHCLKA-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(2-pyrrolidin-1-ylethylamino)benzenesulfonate Chemical compound N=1C2=CC=C(OS(=O)(=O)C=3C=CC(NCCN4CCCC4)=CC=3)C=C2NC=1NC(=O)NCC1=CC=CC=N1 MMOCLWWJYHCLKA-UHFFFAOYSA-N 0.000 description 1
• GTGQZEWTEUEKRZ-UHFFFAOYSA-N [2-(pyridin-2-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(oxan-4-ylmethylamino)benzenesulfonate Chemical compound N=1C2=CC=C(OS(=O)(=O)C=3C=CC(NCC4CCOCC4)=CC=3)C=C2NC=1NC(=O)NCC1=CC=CC=N1 GTGQZEWTEUEKRZ-UHFFFAOYSA-N 0.000 description 1
• QAEBPKXYINYPFY-UHFFFAOYSA-N [2-(pyridin-3-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2NC=1NC(=O)NCC1=CC=CN=C1 QAEBPKXYINYPFY-UHFFFAOYSA-N 0.000 description 1
• FGSPAWAQTBEOJK-UHFFFAOYSA-N [2-(pyridin-4-ylmethylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)NCC1=CC=NC=C1 FGSPAWAQTBEOJK-UHFFFAOYSA-N 0.000 description 1
• FVBTZBHFBFXTKY-UHFFFAOYSA-N [2-(pyridine-3-carbonylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=CN=CC=1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 FVBTZBHFBFXTKY-UHFFFAOYSA-N 0.000 description 1
• KLBVSXUIDPHJIJ-UHFFFAOYSA-N [2-(pyridine-4-carbonylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=NC=CC=1C(=O)NC(NC1=CC=2)=NC1=CC=2OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 KLBVSXUIDPHJIJ-UHFFFAOYSA-N 0.000 description 1
• UZLOXFZSPPZGDQ-UHFFFAOYSA-N [2-(tert-butylcarbamoylamino)-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NC(C)(C)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 UZLOXFZSPPZGDQ-UHFFFAOYSA-N 0.000 description 1
• ZVKHOJLXXXZLLL-UHFFFAOYSA-N [2-[(1-ethylpyrrolidin-2-yl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound CCN1CCCC1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 ZVKHOJLXXXZLLL-UHFFFAOYSA-N 0.000 description 1
• KTBKCKBKTOMTHO-UHFFFAOYSA-N [2-[(2-amino-2-methylpropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(C)(N)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 KTBKCKBKTOMTHO-UHFFFAOYSA-N 0.000 description 1
• CURQUJRZCPOZFJ-UHFFFAOYSA-N [2-[(2-amino-2-methylpropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(C)(N)C)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 CURQUJRZCPOZFJ-UHFFFAOYSA-N 0.000 description 1
• JKWZUAQAEIRFJQ-UHFFFAOYSA-N [2-[(2-amino-2-oxoethyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(=O)N)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1NC1CCCC1 JKWZUAQAEIRFJQ-UHFFFAOYSA-N 0.000 description 1
• JWHJLEQIKVTBGS-UHFFFAOYSA-N [2-[(2-amino-2-oxoethyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCC(=O)N)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 JWHJLEQIKVTBGS-UHFFFAOYSA-N 0.000 description 1
• BNTSLIRAIBLSJI-UHFFFAOYSA-N [2-[(2-carbamoylpyrrolidine-1-carbonyl)amino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound NC(=O)C1CCCN1C(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 BNTSLIRAIBLSJI-UHFFFAOYSA-N 0.000 description 1
• ZUYQYEOPSORCJV-UHFFFAOYSA-N [2-[(2-chlorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound ClC1=CC=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 ZUYQYEOPSORCJV-UHFFFAOYSA-N 0.000 description 1
• LMEIEPYJQANBPG-UHFFFAOYSA-N [2-[(2-chlorophenyl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound ClC1=CC=CC=C1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 LMEIEPYJQANBPG-UHFFFAOYSA-N 0.000 description 1
• GUCBYNQPGYTQJI-UHFFFAOYSA-N [2-[(2-cyclopropylacetyl)amino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound N=1C2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2NC=1NC(=O)CC1CC1 GUCBYNQPGYTQJI-UHFFFAOYSA-N 0.000 description 1
• LCHPLQNHFQFOBP-UHFFFAOYSA-N [2-[(2-fluorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound FC1=CC=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 LCHPLQNHFQFOBP-UHFFFAOYSA-N 0.000 description 1
• JIYPJMZKYWWWME-UHFFFAOYSA-N [2-[(2-fluorophenyl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound FC1=CC=CC=C1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 JIYPJMZKYWWWME-UHFFFAOYSA-N 0.000 description 1
• WWRZMRYZQCLDJM-UHFFFAOYSA-N [2-[(2-fluorophenyl)methylcarbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound FC1=CC=CC=C1CNC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 WWRZMRYZQCLDJM-UHFFFAOYSA-N 0.000 description 1
• IJQBJGPSDZRYMS-UHFFFAOYSA-N [2-[(2-hydroxy-3-methoxypropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-[(2-hydroxy-3-methoxypropyl)amino]benzenesulfonate Chemical compound C1=C2NC(NC(=O)NCC(O)COC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(NCC(O)COC)C=C1 IJQBJGPSDZRYMS-UHFFFAOYSA-N 0.000 description 1
• QVTXENWSYPIFGG-UHFFFAOYSA-N [2-[(2-methoxyacetyl)amino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)COC)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 QVTXENWSYPIFGG-UHFFFAOYSA-N 0.000 description 1
• GHEJSFJEXSTJIP-UHFFFAOYSA-N [2-[(2-methoxyphenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound COC1=CC=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 GHEJSFJEXSTJIP-UHFFFAOYSA-N 0.000 description 1
• YWZNHXZZKGSPEZ-UHFFFAOYSA-N [2-[(3-amino-3-oxopropyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)NCCC(=O)N)=NC2=CC=1OS(=O)(=O)C(C=C1)=CC=C1N1C=CN=C1 YWZNHXZZKGSPEZ-UHFFFAOYSA-N 0.000 description 1
• DVBNJSIAUOVIOO-UHFFFAOYSA-N [2-[(3-chlorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound ClC1=CC=CC(NC(=O)NC=2NC3=CC=C(OS(=O)(=O)C=4C=CC(=CC=4)N4C=NC=C4)C=C3N=2)=C1 DVBNJSIAUOVIOO-UHFFFAOYSA-N 0.000 description 1
• MMJWXKSDMOGPMT-UHFFFAOYSA-N [2-[(3-methoxyphenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound COC1=CC=CC(NC(=O)NC=2NC3=CC=C(OS(=O)(=O)C=4C=CC(NC5CCCC5)=CC=4)C=C3N=2)=C1 MMJWXKSDMOGPMT-UHFFFAOYSA-N 0.000 description 1
• KRCCVHHGDDGWAK-UHFFFAOYSA-N [2-[(3-methoxyphenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound COC1=CC=CC(NC(=O)NC=2NC3=CC=C(OS(=O)(=O)C=4C=CC(=CC=4)N4C=NC=C4)C=C3N=2)=C1 KRCCVHHGDDGWAK-UHFFFAOYSA-N 0.000 description 1
• CABWYZQIWNRHFD-UHFFFAOYSA-N [2-[(4-chlorophenyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 CABWYZQIWNRHFD-UHFFFAOYSA-N 0.000 description 1
• OBRQSYVTNVRMJP-UHFFFAOYSA-N [2-[(4-hydroxycyclohexyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-(cyclopentylamino)benzenesulfonate Chemical compound C1CC(O)CCC1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(NC4CCCC4)=CC=3)=CC=C2N1 OBRQSYVTNVRMJP-UHFFFAOYSA-N 0.000 description 1
• HXCZFNQCMVSHKP-UHFFFAOYSA-N [2-[(4-hydroxycyclohexyl)carbamoylamino]-3h-benzimidazol-5-yl] 4-imidazol-1-ylbenzenesulfonate Chemical compound C1CC(O)CCC1NC(=O)NC1=NC2=CC(OS(=O)(=O)C=3C=CC(=CC=3)N3C=NC=C3)=CC=C2N1 HXCZFNQCMVSHKP-UHFFFAOYSA-N 0.000 description 1
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