JP2008533151A5 - - Google Patents
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- Publication number
- JP2008533151A5 JP2008533151A5 JP2008501948A JP2008501948A JP2008533151A5 JP 2008533151 A5 JP2008533151 A5 JP 2008533151A5 JP 2008501948 A JP2008501948 A JP 2008501948A JP 2008501948 A JP2008501948 A JP 2008501948A JP 2008533151 A5 JP2008533151 A5 JP 2008533151A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- amide
- benzimidazole
- imidazol
- benzimidazol
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 26
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 18
- 208000024827 Alzheimer disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 230000003993 interaction Effects 0.000 claims 4
- 239000003446 ligand Substances 0.000 claims 4
- -1 {4- [2- (1H- benzimidazol-2-yl) - ethylcarbamoyl]-1H-benzimidazol-2-yl} - amide Chemical compound 0.000 claims 4
- 102100021257 Beta-secretase 1 Human genes 0.000 claims 3
- 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 2
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims 2
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims 2
- 206010012239 Delusion Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 206010002022 amyloidosis Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 231100000868 delusion Toxicity 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 230000007406 plaque accumulation Effects 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- REDRQHKMLWLDKF-UHFFFAOYSA-N 2-(isoquinolin-3-ylamino)-n-(4-methoxyphenyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC2=C1NC(NC=1N=CC3=CC=CC=C3C=1)=N2 REDRQHKMLWLDKF-UHFFFAOYSA-N 0.000 claims 1
- DPZXAHOQZNGFFO-UHFFFAOYSA-N 2-(isoquinolin-3-ylamino)-n-phenyl-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC=2N=C(NC=3N=CC4=CC=CC=C4C=3)NC=2C=1C(=O)NC1=CC=CC=C1 DPZXAHOQZNGFFO-UHFFFAOYSA-N 0.000 claims 1
- BXQYWBDHNSYVRY-UHFFFAOYSA-N 2-[(1,5-dimethylindole-2-carbonyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C=1C2=CC(C)=CC=C2N(C)C=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 BXQYWBDHNSYVRY-UHFFFAOYSA-N 0.000 claims 1
- UFJMFVZQYLOJFB-UHFFFAOYSA-N 2-[(1-benzylindole-2-carbonyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C=1C2=CC=CC=C2N(CC=2C=CC=CC=2)C=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 UFJMFVZQYLOJFB-UHFFFAOYSA-N 0.000 claims 1
- BTFKPFGRLMNQNW-UHFFFAOYSA-N 2-[(2-chlorobenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound ClC1=CC=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 BTFKPFGRLMNQNW-UHFFFAOYSA-N 0.000 claims 1
- XNXBQZHJNSDVQM-UHFFFAOYSA-N 2-[(2-fluorobenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound FC1=CC=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 XNXBQZHJNSDVQM-UHFFFAOYSA-N 0.000 claims 1
- PUFIGMFPXPZODO-UHFFFAOYSA-N 2-[(3,4-dimethoxybenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 PUFIGMFPXPZODO-UHFFFAOYSA-N 0.000 claims 1
- YYCWDBDINNAQTH-UHFFFAOYSA-N 2-[(3,5-difluorobenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound FC1=CC(F)=CC(C(=O)NC=2NC3=C(C(=O)NC=4NC=CN=4)C=CC=C3N=2)=C1 YYCWDBDINNAQTH-UHFFFAOYSA-N 0.000 claims 1
- YQZGCJOCTVTNGB-UHFFFAOYSA-N 2-[(3-fluorobenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound FC1=CC=CC(C(=O)NC=2NC3=C(C(=O)NC=4NC=CN=4)C=CC=C3N=2)=C1 YQZGCJOCTVTNGB-UHFFFAOYSA-N 0.000 claims 1
- QBRTUDWKEZRWNB-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=NC2=C(C(=O)NC=3NC=CN=3)C=CC=C2N1 QBRTUDWKEZRWNB-UHFFFAOYSA-N 0.000 claims 1
- UEGPDKFYZHJHSK-UHFFFAOYSA-N 2-[(4-fluoro-3-methoxybenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=C(F)C(OC)=CC(C(=O)NC=2NC3=C(C(=O)NC=4NC=CN=4)C=CC=C3N=2)=C1 UEGPDKFYZHJHSK-UHFFFAOYSA-N 0.000 claims 1
- NRBIGPPBQPOAIW-UHFFFAOYSA-N 2-[(4-fluorobenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 NRBIGPPBQPOAIW-UHFFFAOYSA-N 0.000 claims 1
- MKUUBNAKDGUWGG-UHFFFAOYSA-N 2-[(4-tert-butylbenzoyl)amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 MKUUBNAKDGUWGG-UHFFFAOYSA-N 0.000 claims 1
- BONUWFJMAMKJBS-UHFFFAOYSA-N 2-[[2-(4-fluorophenyl)acetyl]amino]-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 BONUWFJMAMKJBS-UHFFFAOYSA-N 0.000 claims 1
- FLXAMFSUBWKOGC-UHFFFAOYSA-N 2-amino-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C=12NC(N)=NC2=CC=CC=1C(=O)NC1=NC=CN1 FLXAMFSUBWKOGC-UHFFFAOYSA-N 0.000 claims 1
- SIOYHWABOSESEJ-UHFFFAOYSA-N 2-benzamido-n-(1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 SIOYHWABOSESEJ-UHFFFAOYSA-N 0.000 claims 1
- RJBYQNGSOBFWIL-UHFFFAOYSA-N 2-isoquinolin-3-yl-n-(5-phenyl-1h-imidazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC=2NC(C=3N=CC4=CC=CC=C4C=3)=NC=2C=1C(=O)NC(NC=1)=NC=1C1=CC=CC=C1 RJBYQNGSOBFWIL-UHFFFAOYSA-N 0.000 claims 1
- MIPKQHRPGRGBIU-UHFFFAOYSA-N 6,7-dimethoxyisoquinoline-3-carboxylic acid Chemical compound N1=C(C(O)=O)C=C2C=C(OC)C(OC)=CC2=C1 MIPKQHRPGRGBIU-UHFFFAOYSA-N 0.000 claims 1
- 229940124810 Alzheimer's drug Drugs 0.000 claims 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims 1
- 229930003427 Vitamin E Natural products 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005275 alkylenearyl group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 230000007131 anti Alzheimer effect Effects 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 1
- 229960001259 diclofenac Drugs 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229960003530 donepezil Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 claims 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000004558 lewy body Anatomy 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- AOOXGPCQXPZOMB-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(1h-indole-2-carbonylamino)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC=C2NC(C(NC=3NC4=CC=CC(=C4N=3)C(=O)NC=3NC4=CC=CC=C4N=3)=O)=CC2=C1 AOOXGPCQXPZOMB-UHFFFAOYSA-N 0.000 claims 1
- KMDDVYGNFWMWCX-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(pyridin-2-ylamino)-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC=CC=C2NC=1NC(=O)C(C=C1N2)=CC=C1N=C2NC1=CC=CC=N1 KMDDVYGNFWMWCX-UHFFFAOYSA-N 0.000 claims 1
- KNAXPDGBZIEBTP-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-naphthalen-2-yl-3h-benzimidazole-5-carboxamide Chemical compound C1=CC=CC2=CC(C=3NC4=CC=C(C=C4N=3)C(NC=3NC4=CC=CC=C4N=3)=O)=CC=C21 KNAXPDGBZIEBTP-UHFFFAOYSA-N 0.000 claims 1
- UKVNFJNGGMOKPQ-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-pyridin-2-yl-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC=CC=C2NC=1NC(=O)C(C=C1N=2)=CC=C1NC=2C1=CC=CC=N1 UKVNFJNGGMOKPQ-UHFFFAOYSA-N 0.000 claims 1
- UTXQATYHCDTLPU-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-(1h-indole-2-carbonylamino)-1h-benzimidazole-4-carboxamide Chemical compound C=1C2=CC=CC=C2NC=1C(=O)NC(NC1=CC=C2)=NC1=C2C(=O)NC1=NC=CN1 UTXQATYHCDTLPU-UHFFFAOYSA-N 0.000 claims 1
- BCQWSULEBBKAMJ-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-(isoquinolin-3-ylamino)-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC=2N=C(NC=3N=CC4=CC=CC=C4C=3)NC=2C=1C(=O)NC1=NC=CN1 BCQWSULEBBKAMJ-UHFFFAOYSA-N 0.000 claims 1
- GDDDHZOHBVARSC-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-(isoquinolin-3-ylamino)-3h-benzimidazole-5-carboxamide Chemical compound C=1C=C2N=C(NC=3N=CC4=CC=CC=C4C=3)NC2=CC=1C(=O)NC1=NC=CN1 GDDDHZOHBVARSC-UHFFFAOYSA-N 0.000 claims 1
- ADHBNWAYMZEQSF-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-(naphthalene-2-carbonylamino)-1h-benzimidazole-4-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC(NC1=CC=C2)=NC1=C2C(=O)NC1=NC=CN1 ADHBNWAYMZEQSF-UHFFFAOYSA-N 0.000 claims 1
- LLEMLFSSJSZFOR-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-(pyridin-2-ylamino)-3h-benzimidazole-5-carboxamide Chemical compound C=1C=C2N=C(NC=3N=CC=CC=3)NC2=CC=1C(=O)NC1=NC=CN1 LLEMLFSSJSZFOR-UHFFFAOYSA-N 0.000 claims 1
- IROXPLUVFLJDGO-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(1-methylindole-2-carbonyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1C2=CC=CC=C2N(C)C=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 IROXPLUVFLJDGO-UHFFFAOYSA-N 0.000 claims 1
- HWFCVPBQVAHWNK-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(1-propylindole-2-carbonyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1C2=CC=CC=C2N(CCC)C=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 HWFCVPBQVAHWNK-UHFFFAOYSA-N 0.000 claims 1
- FDISPZPLEREWPS-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(4-methoxybenzoyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 FDISPZPLEREWPS-UHFFFAOYSA-N 0.000 claims 1
- FKWFBUSCPMWNPI-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(4-nitrobenzoyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 FKWFBUSCPMWNPI-UHFFFAOYSA-N 0.000 claims 1
- BZAYJTGSTUVJPM-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(4-phenoxybenzoyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)NC(NC1=CC=C2)=NC1=C2C(=O)NC1=NC=CN1 BZAYJTGSTUVJPM-UHFFFAOYSA-N 0.000 claims 1
- NQFWEZBPLUCTPE-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(4-phenylbenzoyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)NC(NC1=CC=C2)=NC1=C2C(=O)NC1=NC=CN1 NQFWEZBPLUCTPE-UHFFFAOYSA-N 0.000 claims 1
- NCUWSQJNQBFGQM-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(4-propan-2-ylbenzoyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1C(=O)NC1=NC2=CC=CC(C(=O)NC=3NC=CN=3)=C2N1 NCUWSQJNQBFGQM-UHFFFAOYSA-N 0.000 claims 1
- RPUAYSHJAPTPRI-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(5-methyl-1h-indole-2-carbonyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1C2=CC(C)=CC=C2NC=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 RPUAYSHJAPTPRI-UHFFFAOYSA-N 0.000 claims 1
- YPUOEDZEMODXLR-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[(6-phenoxypyridine-2-carbonyl)amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC(OC=2C=CC=CC=2)=NC=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 YPUOEDZEMODXLR-UHFFFAOYSA-N 0.000 claims 1
- HFHWSAODUBTRNO-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[[4-(trifluoromethyl)benzoyl]amino]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC1=NC2=C(C(=O)NC=3NC=CN=3)C=CC=C2N1 HFHWSAODUBTRNO-UHFFFAOYSA-N 0.000 claims 1
- UYKBRBDEUIHXGH-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[[5-(2-phenylethynyl)pyridine-3-carbonyl]amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1N=CC(C#CC=2C=CC=CC=2)=CC=1C(=O)NC(NC1=CC=C2)=NC1=C2C(=O)NC1=NC=CN1 UYKBRBDEUIHXGH-UHFFFAOYSA-N 0.000 claims 1
- BNCARJAWLUNMPH-UHFFFAOYSA-N n-(1h-imidazol-2-yl)-2-[[6-(2-phenylethynyl)pyridine-2-carbonyl]amino]-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC(C#CC=2C=CC=CC=2)=NC=1C(=O)NC(NC1=CC=C2)=NC1=C2C(=O)NC1=NC=CN1 BNCARJAWLUNMPH-UHFFFAOYSA-N 0.000 claims 1
- VCMBSXHBEUBPMZ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(isoquinolin-3-ylamino)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CC2=C1NC(NC=1N=CC3=CC=CC=C3C=1)=N2 VCMBSXHBEUBPMZ-UHFFFAOYSA-N 0.000 claims 1
- YEGCIUAOIVAIKE-UHFFFAOYSA-N n-(4-fluorophenyl)-2-(isoquinolin-3-ylamino)-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC2=C1NC(NC=1N=CC3=CC=CC=C3C=1)=N2 YEGCIUAOIVAIKE-UHFFFAOYSA-N 0.000 claims 1
- OIEBPWKAVOFYAU-UHFFFAOYSA-N n-[4-(1h-benzimidazol-2-ylcarbamoyl)-1h-benzimidazol-2-yl]isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(NC=3NC4=C(C(=O)NC=5NC6=CC=CC=C6N=5)C=CC=C4N=3)=O)=CC2=C1 OIEBPWKAVOFYAU-UHFFFAOYSA-N 0.000 claims 1
- YTIHWBQYPRIIBE-UHFFFAOYSA-N n-[4-(1h-imidazol-2-ylcarbamoyl)-1h-benzimidazol-2-yl]isoquinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2C=NC=1C(=O)NC(NC1=2)=NC1=CC=CC=2C(=O)NC1=NC=CN1 YTIHWBQYPRIIBE-UHFFFAOYSA-N 0.000 claims 1
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-
2006
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- 2006-03-14 CN CN2006800084176A patent/CN101142194B/zh not_active Expired - Fee Related
- 2006-03-14 JP JP2008501948A patent/JP5066514B2/ja not_active Expired - Fee Related
- 2006-03-14 CA CA2600570A patent/CA2600570C/en not_active Expired - Fee Related
- 2006-03-14 US US11/885,096 patent/US7893267B2/en not_active Expired - Fee Related
- 2006-03-14 BR BRPI0608581-4A patent/BRPI0608581A2/pt not_active IP Right Cessation
- 2006-03-14 MX MX2007011234A patent/MX2007011234A/es active IP Right Grant
- 2006-03-14 NZ NZ561029A patent/NZ561029A/en not_active IP Right Cessation
- 2006-03-14 ES ES06738139T patent/ES2400287T3/es active Active
- 2006-03-14 US US11/374,723 patent/US20060223849A1/en not_active Abandoned
- 2006-03-14 WO PCT/US2006/009049 patent/WO2006099379A2/en not_active Ceased
- 2006-03-14 AU AU2006223070A patent/AU2006223070B2/en not_active Ceased
- 2006-03-14 EP EP12150487A patent/EP2457901A1/en not_active Withdrawn
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2007
- 2007-08-27 IL IL185541A patent/IL185541A/en not_active IP Right Cessation
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2009
- 2009-05-13 ZA ZA2009/03300A patent/ZA200903300B/en unknown
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- 2010-11-19 US US12/950,718 patent/US8598353B2/en not_active Expired - Fee Related
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2011
- 2011-11-24 JP JP2011256487A patent/JP2012046541A/ja not_active Ceased
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2012
- 2012-10-25 IL IL222698A patent/IL222698A0/en unknown
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- 2013-10-28 US US14/064,737 patent/US8946259B2/en not_active Expired - Fee Related
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