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
- QTOLSKNUFLJUEO-UHFFFAOYSA-N n-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-1-methyl-2-[[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino]benzimidazole-5-carboxamide Chemical compound C=1C=C2N(C)C(NC=3SC4=CC(OC(F)(F)F)=CC=C4N=3)=NC2=CC=1C(=O)NCC(=O)N1CCC(O)CC1 QTOLSKNUFLJUEO-UHFFFAOYSA-N 0.000 claims 1
- 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
- QCGGTVVSGLTYJW-UHFFFAOYSA-N n-[2-(dimethylamino)-2-oxoethyl]-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)NCC(=O)N(C)C)=NC2=C1 QCGGTVVSGLTYJW-UHFFFAOYSA-N 0.000 claims 1
- KZNLWKXCYRNUEJ-UHFFFAOYSA-N n-[2-(dimethylamino)-2-oxoethyl]-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)NCC(=O)N(C)C)=NC2=C1 KZNLWKXCYRNUEJ-UHFFFAOYSA-N 0.000 claims 1
- CPTVWSKOUUBYGU-OAHLLOKOSA-N n-[2-[(3r)-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-OAHLLOKOSA-N 0.000 claims 1
- 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
- DBOFDRVFFQCCEL-CQSZACIVSA-N n-[2-[(3r)-3-hydroxypyrrolidin-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)N1CC[C@@H](O)C1 DBOFDRVFFQCCEL-CQSZACIVSA-N 0.000 claims 1
- 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
- WQYAOGYRBPSHQR-UHFFFAOYSA-N n-[3-(dimethylamino)-3-oxopropyl]-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)NCCC(=O)N(C)C)=NC2=C1 WQYAOGYRBPSHQR-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 |
| MX2021008071A (es) * | 2019-01-18 | 2021-09-08 | Vtv Therapeutics Llc | Derivados de imidazol fusionado sustituido y métodos de tratamiento de la anemia de células falciformes y complicaciones relacionadas. |
| IL287183B2 (en) | 2019-04-12 | 2025-01-01 | Mitobridge Inc | Inductors 1 HMOX |
| CA3170063A1 (en) | 2020-02-05 | 2021-08-12 | Vtv Therapeutics Llc | Substituted fused imidazole derivatives and methods of treating refractive ocular disorders |
| 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 |
Family Cites Families (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166452A (en) | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
| US4356108A (en) | 1979-12-20 | 1982-10-26 | The Mead Corporation | Encapsulation process |
| US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
| US4973666A (en) | 1987-11-06 | 1990-11-27 | Washington Research Foundation | Peptide fragments containing HP and LP cross-links |
| US5320970A (en) | 1987-11-06 | 1994-06-14 | Washington Research Foundation | Detection of collagen degradation in vivo |
| US5300434A (en) | 1987-11-06 | 1994-04-05 | Washington Research Foundation | Hybridoma cell line producing an antibody to type-I collagen amino-terminal telopeptide |
| US5561134A (en) | 1990-09-25 | 1996-10-01 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
| EP0639573A1 (de) | 1993-08-03 | 1995-02-22 | Hoechst Aktiengesellschaft | Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament |
| FR2716192B1 (fr) | 1994-02-17 | 1996-04-12 | Rhone Poulenc Agrochimie | Dérivés de 2-imidazoline-5-ones fongicides. |
| CA2132690A1 (en) * | 1994-09-22 | 1996-03-23 | Dean Willis | Control and modulation of inflammatory response in humans in need of such control and modulation |
| US6562854B2 (en) | 1994-12-14 | 2003-05-13 | Axys Pharmaceuticals, Inc. | Compositions comprising a substituted benzimidazole useful for treating immunomediated inflammatory disorders |
| JP2001519806A (ja) | 1997-04-07 | 2001-10-23 | アクシス ファーマシューティカルズ，インコーポレイティド | セリンプロテアーゼ活性、特にトリプターゼ活性に関連する疾病を処理するための化合物及び組成物 |
| WO1999026932A1 (en) | 1997-11-26 | 1999-06-03 | Axys Pharmaceuticals, Inc. | By amidino group substituted heterocyclic derivatives and their use as anticoagulants |
| JP2000038387A (ja) | 1998-05-19 | 2000-02-08 | Sankyo Co Ltd | 三環性カルバペネム化合物 |
| JP2002521375A (ja) | 1998-07-23 | 2002-07-16 | アストラゼネカ アクチエボラーク | 化合物 |
| DE19853487A1 (de) | 1998-11-19 | 2000-05-25 | Fumapharm Ag Muri | Verwendung von Dialkylfumaraten |
| DK1194425T3 (da) | 1999-06-23 | 2005-11-21 | Aventis Pharma Gmbh | Substituerede benzimidazoler |
| US8639009B2 (en) | 2000-10-11 | 2014-01-28 | Imatx, Inc. | Methods and devices for evaluating and treating a bone condition based on x-ray image analysis |
| JP2004517080A (ja) | 2000-11-29 | 2004-06-10 | グラクソ グループ リミテッド | Ｔｉｅ−２および／またはｖｅｇｆｒ−２の阻害剤として有用なベンゾイミダゾール誘導体 |
| SE0101387D0 (sv) | 2001-04-20 | 2001-04-20 | Astrazeneca Ab | Novel compounds |
| US7030150B2 (en) | 2001-05-11 | 2006-04-18 | Trimeris, Inc. | Benzimidazole compounds and antiviral uses thereof |
| JP2003344971A (ja) | 2002-05-24 | 2003-12-03 | Konica Minolta Holdings Inc | ハロゲン化銀写真感光材料 |
| CN1674942A (zh) * | 2002-06-21 | 2005-09-28 | 联邦高等教育系统匹兹堡大学 | 氧化氮、血红素加氧酶－1和血红素降解产物的药学用途 |
| AU2003243921B2 (en) | 2002-06-27 | 2009-05-07 | Novo Nordisk A/S | Aryl carbonyl derivatives as therapeutic agents |
| SE0203070D0 (en) | 2002-10-16 | 2002-10-16 | Astrazeneca Ab | Novel compounds |
| FR2851563B1 (fr) | 2003-02-26 | 2005-04-22 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et d'imidazo-pyridine et leur utilisation en tant que medicament |
| US7531553B2 (en) | 2003-03-21 | 2009-05-12 | Amgen Inc. | Heterocyclic compounds and methods of use |
| WO2005103716A2 (en) | 2004-04-27 | 2005-11-03 | Galapagos N.V. | Methods, agents, and compound screening assays for inducing differentiation of undifferentiated mammalian cells into osteoblasts |
| GB0412467D0 (en) | 2004-06-04 | 2004-07-07 | Astrazeneca Ab | Chemical compounds |
| EP1838690A2 (en) | 2004-12-21 | 2007-10-03 | Devgen N.V. | Compounds with kv4 ion channel activity |
| US7429608B2 (en) | 2005-01-20 | 2008-09-30 | Amgen Inc. | Benzo[d]imidazol analogs as vanilloid receptor ligands and their use in treatments |
| DE102005003362A1 (de) | 2005-01-25 | 2006-07-27 | Wella Aktiengesellschaft | Kationische Azacyanin-Farbstoffe enthaltende Färbemittel |
| AU2006202040A1 (en) | 2005-05-20 | 2006-12-07 | Reto Brun | Novel biochalcophenes and their prodrugs as antiprotozoal agents |
| US20100249175A1 (en) | 2005-12-02 | 2010-09-30 | Wilson W David | Dicationic compounds which selectively recognize G-quadruplex DNA |
| CN101379060B (zh) * | 2006-02-10 | 2012-05-23 | 转化技术制药公司 | 作为Aurora激酶抑制剂的苯并唑系衍生物、组合物和使用方法 |
| AU2007216531A1 (en) | 2006-02-14 | 2007-08-23 | Neurosearch A/S | Novel diazabicycloalkane derivatives and their medical use |
| EP1996567B1 (en) | 2006-02-15 | 2013-09-18 | AbbVie Inc. | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| EP2680010A1 (en) | 2007-02-08 | 2014-01-01 | Biogen Idec MA Inc. | Nrf2 screening assays and related methods and compositions |
| WO2008113255A1 (fr) | 2007-03-16 | 2008-09-25 | The Institute Of Radiation Medicine, Academy Of Military Medical Sciences, Pla | Dérivés de benzamide avec activité antiproliférative, leurs préparations pharmaceutiques |
| WO2008153701A1 (en) | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| CA2727528A1 (en) * | 2007-06-14 | 2008-12-18 | Osta Biotechnologies | Heme-oxygenase inhibitors and use of the same in the treatment of cancer and diseases of the central nervous system |
| US20100249030A1 (en) | 2007-07-31 | 2010-09-30 | Schering Corporation | Anti-mitotic agent and aurora kinase inhibitor combination as anti-cancer treatment |
| US8088824B2 (en) | 2007-08-15 | 2012-01-03 | Reata Pharmaceuticals Inc. | Forms of CDDO methyl ester |
| WO2009051796A2 (en) | 2007-10-17 | 2009-04-23 | The University Of North Carolina At Chapel Hill | 2,5-diaryl selenophene compounds, aza 2,5-diaryl thiophene compounds, and their prodrugs as antiprotozoal agents |
| UA103013C2 (uk) | 2007-12-06 | 2013-09-10 | Тиботек Фармасьютикелз | Амідні сполуки як активатори противірусних препаратів |
| JP2009149589A (ja) | 2007-12-24 | 2009-07-09 | Dnp Fine Chemicals Co Ltd | 非対称モノアザメチンシアニンの製造方法 |
| BRPI0907423A2 (pt) | 2008-01-11 | 2020-10-27 | Reata Pharmaceuticals, Inc. | composto triterpenoide sintético para uso em um método de melhoria da função renal em um indivíduo, e uso do referido composto |
| WO2009116074A2 (en) | 2008-02-13 | 2009-09-24 | Cadila Healthcare Limited | Substituted benzimidazoles as cannabinoid modulator |
| CA2721060A1 (en) | 2008-04-09 | 2009-10-15 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| WO2009126635A1 (en) | 2008-04-09 | 2009-10-15 | Abbott Laboratories | 2-amino-benzothiazole derivates useful as inhibitors of rock kinases |
| KR101713140B1 (ko) | 2008-04-18 | 2017-03-08 | 리타 파마슈티컬스 잉크. | Ｃ-환에서 포화된 산화방지성 염증 조절제 올레아놀산 유도체 |
| US20110039895A1 (en) | 2008-04-30 | 2011-02-17 | Glaxo Smith Kline LLC., a corporation | Prolyl hydroxylase inhibitors |
| AR071523A1 (es) | 2008-04-30 | 2010-06-23 | Merck Serono Sa | Compuestos biciclicos fusionados, un proceso para su preparacion, el compuesto para ser utilizado como medicamento en el tratamiento y profilaxis de enfermedades, una composicion farmaceutica y un conjunto que comprende paquetes separados del compuesto y de un ingrediente activo del medicamento |
| GB0810981D0 (en) | 2008-06-16 | 2008-07-23 | Univ Leuven Kath | Novel compounds |
| FR2933982A1 (fr) | 2008-07-18 | 2010-01-22 | Sanofi Aventis | Nouveaux derives imidazo°1,2-a!pyrimidine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
| JP2011528337A (ja) | 2008-07-18 | 2011-11-17 | サノフイ−アベンテイス | 新規トリアゾロ［４，３−ａ］ピリジン誘導体、これらの調製方法、医薬としてのこれらの使用、医薬組成物および、特にｍｅｔ阻害剤としての、新規使用 |
| CN102159559A (zh) | 2008-07-18 | 2011-08-17 | 赛诺菲-安万特 | 新型咪唑并[1,2-a]吡啶衍生物、其制备方法、其作为药物的用途、其药物组合物和新型用途特别是作为MET抑制剂的新型用途 |
| US8394969B2 (en) | 2008-09-26 | 2013-03-12 | Merck Sharp & Dohme Corp. | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010065674A1 (en) | 2008-12-03 | 2010-06-10 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| WO2010135014A1 (en) | 2009-02-27 | 2010-11-25 | Vertex Pharmaceuticals Incorporated | Tri-cyclic pyrazolopyridine kinase inhibitors |
| US8759535B2 (en) | 2010-02-18 | 2014-06-24 | High Point Pharmaceuticals, Llc | Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof |
| DK2536285T3 (en) | 2010-02-18 | 2018-07-16 | Vtv Therapeutics Llc | Substituted fused imidazole derivatives, pharmaceutical compositions and methods for their use |
| WO2012094580A2 (en) | 2011-01-07 | 2012-07-12 | High Point Pharmaceuticals, Llc | Compounds that modulate oxidative stress |
| US9655905B2 (en) | 2011-09-14 | 2017-05-23 | King Abdullah University Of Science And Technology | Treatment of sickle cell disease |
| US20130158077A1 (en) | 2011-12-19 | 2013-06-20 | Ares Trading S.A. | Pharmaceutical compositions |
| US20140171504A1 (en) | 2012-12-14 | 2014-06-19 | Georgia Regents Research Institute, Inc. | Methods of Treating Sickle Cell Disease and Related Disorders Using Fumaric Acid Esters |
| US9944669B2 (en) | 2014-03-21 | 2018-04-17 | Universite Paris Est Creteil Val De Marne | Fumarate-CO-releasing molecule hybrids, their use in the treatment of inflammatory or cardiovascular diseases and their process of preparation |
| US10039513B2 (en) | 2014-07-21 | 2018-08-07 | Zebra Medical Vision Ltd. | Systems and methods for emulating DEXA scores based on CT images |
| 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 |
| MX2021008071A (es) | 2019-01-18 | 2021-09-08 | Vtv Therapeutics Llc | Derivados de imidazol fusionado sustituido y métodos de tratamiento de la anemia de células falciformes y complicaciones relacionadas. |
| IL287183B2 (en) | 2019-04-12 | 2025-01-01 | Mitobridge Inc | Inductors 1 HMOX |
| CA3170063A1 (en) | 2020-02-05 | 2021-08-12 | Vtv Therapeutics Llc | Substituted fused imidazole derivatives and methods of treating refractive ocular disorders |
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2011
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2023
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