JP2013520420A5 - - Google Patents
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- Publication number
- JP2013520420A5 JP2013520420A5 JP2012553942A JP2012553942A JP2013520420A5 JP 2013520420 A5 JP2013520420 A5 JP 2013520420A5 JP 2012553942 A JP2012553942 A JP 2012553942A JP 2012553942 A JP2012553942 A JP 2012553942A JP 2013520420 A5 JP2013520420 A5 JP 2013520420A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- benzothiazol
- ylamino
- amide
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 176
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- -1 azetidino Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000002177 Cataract Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000002249 Diabetes Complications Diseases 0.000 claims description 3
- 206010051920 Glomerulonephropathy Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 208000002780 macular degeneration Diseases 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 101000588302 Homo sapiens Nuclear factor erythroid 2-related factor 2 Proteins 0.000 claims description 2
- 102100031701 Nuclear factor erythroid 2-related factor 2 Human genes 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000000729 antidote Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XSZGCGHXDKUWDX-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-yl-2-oxoethyl)-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C)C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)=NC2=CC=1C(=O)NCC(=O)N1CCOCC1 XSZGCGHXDKUWDX-UHFFFAOYSA-N 0.000 claims 1
- DAXPSZBDWZWCTP-UHFFFAOYSA-N 1-methyl-n-(2-morpholin-4-ylethyl)-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C)C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)=NC2=CC=1C(=O)NCCN1CCOCC1 DAXPSZBDWZWCTP-UHFFFAOYSA-N 0.000 claims 1
- QEMNNHCYNIZMRJ-UHFFFAOYSA-N 1-methyl-n-(3-methylsulfonylpropyl)-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound CS(=O)(=O)CCCNC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(OC(F)(F)F)=CC=C4N=3)=NC2=C1 QEMNNHCYNIZMRJ-UHFFFAOYSA-N 0.000 claims 1
- IVHSUHQPSPUUOP-UHFFFAOYSA-N 1-methyl-n-(3-morpholin-4-yl-3-oxopropyl)-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C)C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)=NC2=CC=1C(=O)NCCC(=O)N1CCOCC1 IVHSUHQPSPUUOP-UHFFFAOYSA-N 0.000 claims 1
- DBZAOKVXTMDLAO-CQSZACIVSA-N 1-methyl-n-[(2r)-1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl]-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound O=C([C@H](NC(=O)C=1C=C2N=C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)N(C)C2=CC=1)C)N1CCN(C)CC1 DBZAOKVXTMDLAO-CQSZACIVSA-N 0.000 claims 1
- LBZGTCJCYUMPON-ZDUSSCGKSA-N 1-methyl-n-[(2s)-1-morpholin-4-yl-1-oxopropan-2-yl]-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound O=C([C@@H](NC(=O)C=1C=C2N=C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)N(C)C2=CC=1)C)N1CCOCC1 LBZGTCJCYUMPON-ZDUSSCGKSA-N 0.000 claims 1
- DXSZLMINZDNCBR-UHFFFAOYSA-N 1-methyl-n-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1CN(C)CCN1C(=O)CNC(=O)C1=CC=C(N(C)C(NC=2SC3=CC(OC(F)(F)F)=CC=C3N=2)=N2)C2=C1 DXSZLMINZDNCBR-UHFFFAOYSA-N 0.000 claims 1
- KPNSYIXTHOWAAT-UHFFFAOYSA-N 1-methyl-n-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1CN(C)CCN1C(=O)CNC(=O)C1=CC=C(N(C)C(NC=2SC3=CC(=CC=C3N=2)C(F)(F)F)=N2)C2=C1 KPNSYIXTHOWAAT-UHFFFAOYSA-N 0.000 claims 1
- UFEOYPYMABXXMY-UHFFFAOYSA-N 1-methyl-n-[2-(methylamino)-2-oxoethyl]-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCC(=O)NC)=NC2=C1 UFEOYPYMABXXMY-UHFFFAOYSA-N 0.000 claims 1
- JRQPFVSXLWBXPV-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-1-ethyl-n-(2-fluoroethyl)benzimidazole-5-carboxamide Chemical compound FCCNC(=O)C1=CC=C2N(CC)C(NC=3SC4=CC(Cl)=CC=C4N=3)=NC2=C1 JRQPFVSXLWBXPV-UHFFFAOYSA-N 0.000 claims 1
- VEZQHDHGRQBASX-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-1-ethyl-n-(2-methoxyethyl)benzimidazole-5-carboxamide Chemical compound COCCNC(=O)C1=CC=C2N(CC)C(NC=3SC4=CC(Cl)=CC=C4N=3)=NC2=C1 VEZQHDHGRQBASX-UHFFFAOYSA-N 0.000 claims 1
- FRLOLVZHVLIVJC-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-1-methylbenzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(Cl)=CC=C4N=3)=NC2=C1 FRLOLVZHVLIVJC-UHFFFAOYSA-N 0.000 claims 1
- YASJQFLLRYLNJM-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-(2-ethoxyethyl)-1-methylbenzimidazole-5-carboxamide Chemical compound C1=C(Cl)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOCC)=NC2=C1 YASJQFLLRYLNJM-UHFFFAOYSA-N 0.000 claims 1
- YWRUZPBCYLGEOS-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-(2-methoxyethyl)-1-methylbenzimidazole-5-carboxamide Chemical compound C1=C(Cl)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOC)=NC2=C1 YWRUZPBCYLGEOS-UHFFFAOYSA-N 0.000 claims 1
- OWIZHCHWMJBBMJ-NSHDSACASA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-[(2s)-1-(dimethylamino)-1-oxopropan-2-yl]-1-methylbenzimidazole-5-carboxamide Chemical compound C1=C(Cl)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)N[C@@H](C)C(=O)N(C)C)=NC2=C1 OWIZHCHWMJBBMJ-NSHDSACASA-N 0.000 claims 1
- XLYPLEDFVDPBRF-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-[2-(2-hydroxyethoxy)ethyl]-1-methylbenzimidazole-5-carboxamide Chemical compound OCCOCCNC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(Cl)=CC=C4N=3)=NC2=C1 XLYPLEDFVDPBRF-UHFFFAOYSA-N 0.000 claims 1
- VWCLQSLVGVCOMO-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-[2-(dimethylamino)-2-oxoethyl]-1-methylbenzimidazole-5-carboxamide Chemical compound C1=C(Cl)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCC(=O)N(C)C)=NC2=C1 VWCLQSLVGVCOMO-UHFFFAOYSA-N 0.000 claims 1
- XUFWDFONRFQANP-OAHLLOKOSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-[2-[(3r)-3-methoxypyrrolidin-1-yl]-2-oxoethyl]-1-methylbenzimidazole-5-carboxamide Chemical compound C1[C@H](OC)CCN1C(=O)CNC(=O)C1=CC=C(N(C)C(NC=2SC3=CC(Cl)=CC=C3N=2)=N2)C2=C1 XUFWDFONRFQANP-OAHLLOKOSA-N 0.000 claims 1
- XUFWDFONRFQANP-HNNXBMFYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-[2-[(3s)-3-methoxypyrrolidin-1-yl]-2-oxoethyl]-1-methylbenzimidazole-5-carboxamide Chemical compound C1[C@@H](OC)CCN1C(=O)CNC(=O)C1=CC=C(N(C)C(NC=2SC3=CC(Cl)=CC=C3N=2)=N2)C2=C1 XUFWDFONRFQANP-HNNXBMFYSA-N 0.000 claims 1
- XXMSGTTYJKZFMD-UHFFFAOYSA-N 2-[(6-chloro-1,3-benzothiazol-2-yl)amino]-n-[3-(dimethylamino)-3-oxopropyl]-1-methylbenzimidazole-5-carboxamide Chemical compound C1=C(Cl)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCC(=O)N(C)C)=NC2=C1 XXMSGTTYJKZFMD-UHFFFAOYSA-N 0.000 claims 1
- RZOUNNWATKMVNU-UHFFFAOYSA-N 3-methyl-n-(2-morpholin-4-ylethyl)-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]imidazo[4,5-b]pyridine-6-carboxamide Chemical compound C=1N=C2N(C)C(NC=3SC4=CC(OC(F)(F)F)=CC=C4N=3)=NC2=CC=1C(=O)NCCN1CCOCC1 RZOUNNWATKMVNU-UHFFFAOYSA-N 0.000 claims 1
- VBMJBIIVNYRJNX-UHFFFAOYSA-N 6-methoxy-1-methyl-n-(2-morpholin-4-ylethyl)-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound COC1=CC=2N(C)C(NC=3SC4=CC(OC(F)(F)F)=CC=C4N=3)=NC=2C=C1C(=O)NCCN1CCOCC1 VBMJBIIVNYRJNX-UHFFFAOYSA-N 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- LFIBGEGLUNWRED-UHFFFAOYSA-N n-(2-ethoxyethyl)-1-(2-methoxyethyl)-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(CCOC)C4=CC=C(C=C4N=3)C(=O)NCCOCC)=NC2=C1 LFIBGEGLUNWRED-UHFFFAOYSA-N 0.000 claims 1
- UEHBRHKNCMOCRN-UHFFFAOYSA-N n-(2-ethoxyethyl)-1-ethyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(CC)C4=CC=C(C=C4N=3)C(=O)NCCOCC)=NC2=C1 UEHBRHKNCMOCRN-UHFFFAOYSA-N 0.000 claims 1
- NDSSJXKOTQNPKI-UHFFFAOYSA-N n-(2-ethoxyethyl)-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOCC)=NC2=C1 NDSSJXKOTQNPKI-UHFFFAOYSA-N 0.000 claims 1
- WYHLJSXAFREKKI-UHFFFAOYSA-N n-(2-ethylsulfonylethyl)-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCS(=O)(=O)CC)=NC2=C1 WYHLJSXAFREKKI-UHFFFAOYSA-N 0.000 claims 1
- RJLXBNUVBHFZMM-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound OCCNC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(OC(F)(F)F)=CC=C4N=3)=NC2=C1 RJLXBNUVBHFZMM-UHFFFAOYSA-N 0.000 claims 1
- IOSBWVOQKVEYFV-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound OCCNC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)=NC2=C1 IOSBWVOQKVEYFV-UHFFFAOYSA-N 0.000 claims 1
- BRRIUZRZJZEFRY-UHFFFAOYSA-N n-(2-methoxy-2-methylpropyl)-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCC(C)(C)OC)=NC2=C1 BRRIUZRZJZEFRY-UHFFFAOYSA-N 0.000 claims 1
- YNURDJJKPNZLMH-UHFFFAOYSA-N n-(2-methoxyethyl)-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOC)=NC2=C1 YNURDJJKPNZLMH-UHFFFAOYSA-N 0.000 claims 1
- QUIZKVBGZQKFJX-UHFFFAOYSA-N n-(2-methoxyethyl)-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOC)=NC2=C1 QUIZKVBGZQKFJX-UHFFFAOYSA-N 0.000 claims 1
- UVLWJOJJAQQXBX-UHFFFAOYSA-N n-(2-methoxyethyl)-3-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]imidazo[4,5-b]pyridine-6-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=NC=C(C=C4N=3)C(=O)NCCOC)=NC2=C1 UVLWJOJJAQQXBX-UHFFFAOYSA-N 0.000 claims 1
- XVMDKAXKEBKVPO-LLVKDONJSA-N n-[(2r)-1-(dimethylamino)-1-oxopropan-2-yl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)N[C@H](C)C(=O)N(C)C)=NC2=C1 XVMDKAXKEBKVPO-LLVKDONJSA-N 0.000 claims 1
- WZQMTCBNXVBXSL-SNVBAGLBSA-N n-[(2r)-2-hydroxypropyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NC[C@H](O)C)=NC2=C1 WZQMTCBNXVBXSL-SNVBAGLBSA-N 0.000 claims 1
- HECCFQJJEDUCOX-SNVBAGLBSA-N n-[(2r)-2-hydroxypropyl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NC[C@H](O)C)=NC2=C1 HECCFQJJEDUCOX-SNVBAGLBSA-N 0.000 claims 1
- ABKAESRNRYAHKJ-NSHDSACASA-N n-[(2s)-1-(dimethylamino)-1-oxopropan-2-yl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)N[C@@H](C)C(=O)N(C)C)=NC2=C1 ABKAESRNRYAHKJ-NSHDSACASA-N 0.000 claims 1
- XVMDKAXKEBKVPO-NSHDSACASA-N n-[(2s)-1-(dimethylamino)-1-oxopropan-2-yl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)N[C@@H](C)C(=O)N(C)C)=NC2=C1 XVMDKAXKEBKVPO-NSHDSACASA-N 0.000 claims 1
- WZQMTCBNXVBXSL-JTQLQIEISA-N n-[(2s)-2-hydroxypropyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NC[C@@H](O)C)=NC2=C1 WZQMTCBNXVBXSL-JTQLQIEISA-N 0.000 claims 1
- QOXGBCLRUXCLJD-UHFFFAOYSA-N n-[2-(2-fluoroethoxy)ethyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound FCCOCCNC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(OC(F)(F)F)=CC=C4N=3)=NC2=C1 QOXGBCLRUXCLJD-UHFFFAOYSA-N 0.000 claims 1
- LCTSITDUYKSJBX-UHFFFAOYSA-N n-[2-(2-hydroxyethoxy)ethyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound OCCOCCNC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(OC(F)(F)F)=CC=C4N=3)=NC2=C1 LCTSITDUYKSJBX-UHFFFAOYSA-N 0.000 claims 1
- BJSHVWKLYLAKTP-UHFFFAOYSA-N n-[2-(2-hydroxyethoxy)ethyl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound OCCOCCNC(=O)C1=CC=C2N(C)C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)=NC2=C1 BJSHVWKLYLAKTP-UHFFFAOYSA-N 0.000 claims 1
- AYFAKGNOPLGJHT-UHFFFAOYSA-N n-[2-(2-methoxyethoxy)ethyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOCCOC)=NC2=C1 AYFAKGNOPLGJHT-UHFFFAOYSA-N 0.000 claims 1
- JLDKODGNYQELDB-UHFFFAOYSA-N n-[2-(2-methoxyethoxy)ethyl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOCCOC)=NC2=C1 JLDKODGNYQELDB-UHFFFAOYSA-N 0.000 claims 1
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- PSCQHHIOAGGTSV-UHFFFAOYSA-N n-[2-(dimethylamino)-2-oxoethyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCC(=O)N(C)C)=NC2=C1 PSCQHHIOAGGTSV-UHFFFAOYSA-N 0.000 claims 1
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- MGFMROFNWGHLDW-OAHLLOKOSA-N n-[2-[(3r)-3-hydroxypiperidin-1-yl]-2-oxoethyl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C)C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)=NC2=CC=1C(=O)NCC(=O)N1CCC[C@@H](O)C1 MGFMROFNWGHLDW-OAHLLOKOSA-N 0.000 claims 1
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- CPTVWSKOUUBYGU-HNNXBMFYSA-N n-[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-2-oxoethyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1[C@@H](N(C)C)CCN1C(=O)CNC(=O)C1=CC=C(N(C)C(NC=2SC3=CC(OC(F)(F)F)=CC=C3N=2)=N2)C2=C1 CPTVWSKOUUBYGU-HNNXBMFYSA-N 0.000 claims 1
- MGFMROFNWGHLDW-HNNXBMFYSA-N n-[2-[(3s)-3-hydroxypiperidin-1-yl]-2-oxoethyl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C)C(NC=3SC4=CC(=CC=C4N=3)C(F)(F)F)=NC2=CC=1C(=O)NCC(=O)N1CCC[C@H](O)C1 MGFMROFNWGHLDW-HNNXBMFYSA-N 0.000 claims 1
- GNDFPFGXDPHXPE-HNNXBMFYSA-N n-[2-[(3s)-3-methoxypyrrolidin-1-yl]-2-oxoethyl]-1-methyl-2-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1[C@@H](OC)CCN1C(=O)CNC(=O)C1=CC=C(N(C)C(NC=2SC3=CC(=CC=C3N=2)C(F)(F)F)=N2)C2=C1 GNDFPFGXDPHXPE-HNNXBMFYSA-N 0.000 claims 1
- IJSFTLRXSMBLKX-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethoxy]ethyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCOCCN(C)C)=NC2=C1 IJSFTLRXSMBLKX-UHFFFAOYSA-N 0.000 claims 1
- KKZNBFOUHGSGIM-UHFFFAOYSA-N n-[3-(dimethylamino)-3-oxopropyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C=C2SC(NC=3N(C)C4=CC=C(C=C4N=3)C(=O)NCCC(=O)N(C)C)=NC2=C1 KKZNBFOUHGSGIM-UHFFFAOYSA-N 0.000 claims 1
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| US8759535B2 (en) | 2010-02-18 | 2014-06-24 | High Point Pharmaceuticals, Llc | Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof |
| WO2012094580A2 (en) * | 2011-01-07 | 2012-07-12 | High Point Pharmaceuticals, Llc | Compounds that modulate oxidative stress |
| KR102301867B1 (ko) * | 2013-12-18 | 2021-09-15 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | Nrf2 조절제 |
| WO2015175845A1 (en) * | 2014-05-15 | 2015-11-19 | Peloton Therapeutics, Inc. | Benzimidazole derivatives and uses thereof |
| WO2016089648A1 (en) | 2014-12-01 | 2016-06-09 | Vtv Therapeutics Llc | Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof |
| WO2020117886A1 (en) * | 2018-12-07 | 2020-06-11 | Vtv Therapeutics Llc | Methods of inhibiting osteoclastogenesis and osteoclast activity |
| KR20210129034A (ko) * | 2019-01-18 | 2021-10-27 | 브이티브이 테라퓨틱스 엘엘씨 | 치환된 융합 이미다졸 유도체 및 겸상 적혈구 질환과 관련 합병증을 치료하는 방법 |
| TW202104211A (zh) * | 2019-04-12 | 2021-02-01 | 美商米突倍基公司 | Hmox1誘導劑 |
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| CN117658832A (zh) * | 2022-09-08 | 2024-03-08 | 史梦婷 | 一种n，n-二甲基双氨乙基醚的制备方法 |
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| WO2020117886A1 (en) | 2018-12-07 | 2020-06-11 | Vtv Therapeutics Llc | Methods of inhibiting osteoclastogenesis and osteoclast activity |
| KR20210129034A (ko) | 2019-01-18 | 2021-10-27 | 브이티브이 테라퓨틱스 엘엘씨 | 치환된 융합 이미다졸 유도체 및 겸상 적혈구 질환과 관련 합병증을 치료하는 방법 |
| TW202104211A (zh) | 2019-04-12 | 2021-02-01 | 美商米突倍基公司 | Hmox1誘導劑 |
| US20230093476A1 (en) | 2020-02-05 | 2023-03-23 | Vtv Therapeutics Llc | Substituted fused imidazole derivatives and methods of treating refractive ocular disorders |
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2011
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- 2011-02-10 JP JP2012553942A patent/JP5814948B2/ja active Active
- 2011-02-10 AU AU2011218316A patent/AU2011218316B2/en active Active
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- 2011-02-10 MX MX2012009628A patent/MX339243B/es active IP Right Grant
- 2011-02-10 SG SG2012053732A patent/SG182629A1/en unknown
- 2011-02-10 EP EP11745064.3A patent/EP2536285B1/en active Active
- 2011-02-10 DK DK11745064.3T patent/DK2536285T3/en active
- 2011-02-10 KR KR1020127023193A patent/KR101837759B1/ko active Active
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2023
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