JP2008533151A5 - - Google Patents
Download PDFInfo
- 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
- AVBAIVJQGVVFMH-UHFFFAOYSA-N n-[4-(1h-imidazol-2-ylcarbamoyl)-6-(3-methylbutanoylamino)-1h-benzimidazol-2-yl]isoquinoline-3-carboxamide Chemical compound C=12N=C(NC(=O)C=3N=CC4=CC=CC=C4C=3)NC2=CC(NC(=O)CC(C)C)=CC=1C(=O)NC1=NC=CN1 AVBAIVJQGVVFMH-UHFFFAOYSA-N 0.000 claims 1
- BMZUPQXUWTYOGL-UHFFFAOYSA-N n-[4-(1h-imidazol-2-ylcarbamoyl)-6-[(2-phenylacetyl)amino]-1h-benzimidazol-2-yl]isoquinoline-3-carboxamide Chemical compound C=1C(C(=O)NC=2NC=CN=2)=C2NC(NC(=O)C=3N=CC4=CC=CC=C4C=3)=NC2=CC=1NC(=O)CC1=CC=CC=C1 BMZUPQXUWTYOGL-UHFFFAOYSA-N 0.000 claims 1
- DHLGALGXGWELNN-UHFFFAOYSA-N n-[6-(1h-benzimidazol-2-ylcarbamoyl)-1h-benzimidazol-2-yl]isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(=O)NC=3NC4=CC=C(C=C4N=3)C(NC=3NC4=CC=CC=C4N=3)=O)=CC2=C1 DHLGALGXGWELNN-UHFFFAOYSA-N 0.000 claims 1
- MDXUDGLOFAJZRO-UHFFFAOYSA-N n-[6-benzamido-4-(1h-imidazol-2-ylcarbamoyl)-1h-benzimidazol-2-yl]isoquinoline-3-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=C1NC(NC(=O)C=2N=CC3=CC=CC=C3C=2)=NC1=1)=CC=1C(=O)NC1=NC=CN1 MDXUDGLOFAJZRO-UHFFFAOYSA-N 0.000 claims 1
- JWMDMOYMTPPOQC-UHFFFAOYSA-N n-benzyl-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)NCC1=CC=CC=C1 JWMDMOYMTPPOQC-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 229960002009 naproxen Drugs 0.000 claims 1
- 210000002682 neurofibrillary tangle Anatomy 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 239000002469 receptor inverse agonist Substances 0.000 claims 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 1
- 229960001225 rifampicin Drugs 0.000 claims 1
- 229960004136 rivastigmine Drugs 0.000 claims 1
- 229960001685 tacrine Drugs 0.000 claims 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
- 229940046009 vitamin E Drugs 0.000 claims 1
- 235000019165 vitamin E Nutrition 0.000 claims 1
- 239000011709 vitamin E Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66134905P | 2005-03-14 | 2005-03-14 | |
| US60/661,349 | 2005-03-14 | ||
| PCT/US2006/009049 WO2006099379A2 (en) | 2005-03-14 | 2006-03-14 | Benzazole derivatives, compositions, and methods of use as b-secretase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011256487A Division JP2012046541A (ja) | 2005-03-14 | 2011-11-24 | ベンズアゾール誘導体、組成物及びβ−セクレターゼ阻害剤としての使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008533151A JP2008533151A (ja) | 2008-08-21 |
| JP2008533151A5 true JP2008533151A5 (enExample) | 2011-02-03 |
| JP5066514B2 JP5066514B2 (ja) | 2012-11-07 |
Family
ID=36694148
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008501948A Expired - Fee Related JP5066514B2 (ja) | 2005-03-14 | 2006-03-14 | ベンズアゾール誘導体、組成物及びβ−セクレターゼ阻害剤としての使用方法 |
| JP2011256487A Ceased JP2012046541A (ja) | 2005-03-14 | 2011-11-24 | ベンズアゾール誘導体、組成物及びβ−セクレターゼ阻害剤としての使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011256487A Ceased JP2012046541A (ja) | 2005-03-14 | 2011-11-24 | ベンズアゾール誘導体、組成物及びβ−セクレターゼ阻害剤としての使用方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US20060223849A1 (enExample) |
| EP (2) | EP1863771B1 (enExample) |
| JP (2) | JP5066514B2 (enExample) |
| CN (1) | CN101142194B (enExample) |
| AU (1) | AU2006223070B2 (enExample) |
| BR (1) | BRPI0608581A2 (enExample) |
| CA (1) | CA2600570C (enExample) |
| ES (1) | ES2400287T3 (enExample) |
| IL (2) | IL185541A (enExample) |
| MX (1) | MX2007011234A (enExample) |
| NZ (1) | NZ561029A (enExample) |
| WO (1) | WO2006099379A2 (enExample) |
| ZA (2) | ZA200707896B (enExample) |
Families Citing this family (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006099379A2 (en) * | 2005-03-14 | 2006-09-21 | Transtech Pharma, Inc. | Benzazole derivatives, compositions, and methods of use as b-secretase inhibitors |
| TWI370820B (en) | 2005-04-27 | 2012-08-21 | Takeda Pharmaceutical | Fused heterocyclic compounds |
| EP2612854B1 (en) | 2005-10-25 | 2015-04-29 | Shionogi&Co., Ltd. | Aminothiazolidine and aminotetrahydrothiazepine derivatives as BACE 1 inhibitors |
| PL1986633T3 (pl) | 2006-02-10 | 2015-01-30 | Summit Oxford Ltd | Leczenie dystrofii mięśniowej Duchenne'a |
| CN102633783A (zh) * | 2006-02-10 | 2012-08-15 | 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 |
| ES2596532T3 (es) | 2006-03-16 | 2017-01-10 | Second Genome, Inc. | Compuestos de bicicloheteroarilo como moduladores de P2X7 y usos de los mismos |
| ES2487967T3 (es) * | 2006-04-20 | 2014-08-25 | Pfizer Products Inc. | Compuestos amido heterocíclicos condensados con fenilo para la prevención y el tratamiento de enfermedades mediadas por la glucoquinasa |
| TW200815349A (en) | 2006-06-22 | 2008-04-01 | Astrazeneca Ab | New compounds |
| PE20080888A1 (es) * | 2006-10-18 | 2008-08-26 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE LA ACIL-TRANSFERASA DE ACIL-CoA-DIACIL-GLICEROL 1 (DGAT1) |
| JP2010507664A (ja) * | 2006-10-25 | 2010-03-11 | 武田薬品工業株式会社 | ベンズイミダゾール化合物 |
| WO2008082003A1 (en) | 2006-12-29 | 2008-07-10 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds having crf antagonistic activity |
| JP5383483B2 (ja) | 2007-04-24 | 2014-01-08 | 塩野義製薬株式会社 | アルツハイマー症治療用医薬組成物 |
| CA2683887A1 (en) | 2007-04-24 | 2008-11-06 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivatives substituted with a cyclic group having inhibitory activity against production of amyloid beta protein |
| TWI362930B (en) | 2007-04-27 | 2012-05-01 | Purdue Pharma Lp | Trpv1 antagonists and uses thereof |
| TW200902499A (en) | 2007-05-15 | 2009-01-16 | Astrazeneca Ab | New compounds |
| JP2010535708A (ja) * | 2007-08-03 | 2010-11-25 | ビオマリン アイジーエー リミテッド | デュシェンヌ型筋ジストロフィーの治療のための薬物併用 |
| GB0715937D0 (en) * | 2007-08-15 | 2007-09-26 | Vastox Plc | Method of treatment og duchenne muscular dystrophy |
| CA2705947C (en) | 2007-11-16 | 2016-08-09 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| JP5650540B2 (ja) | 2007-12-12 | 2015-01-07 | ライジェル ファーマシューティカルズ， インコーポレイテッド | 代謝障害のためのカルボキサミド、スルホンアミド、およびアミン化合物 |
| TWI498115B (zh) * | 2007-12-27 | 2015-09-01 | Daiichi Sankyo Co Ltd | 咪唑羰基化合物 |
| WO2009083553A1 (en) * | 2007-12-31 | 2009-07-09 | Rheoscience A/S | Azine compounds as glucokinase activators |
| FR2925904B1 (fr) * | 2008-01-02 | 2010-01-01 | Sanofi Aventis | DERIVES DE N-HETEROCYCLIQUE-6-HETEROCYCLIQUE-IMIDAZO°1,2-a! PYRIDINE-2-CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| NZ588652A (en) | 2008-04-23 | 2012-09-28 | Rigel Pharmaceuticals Inc | Carboxamide compounds for the treatment of metabolic disorders |
| DE102008022221A1 (de) | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
| JP5490692B2 (ja) | 2008-06-13 | 2014-05-14 | 塩野義製薬株式会社 | βセクレターゼ阻害作用を有する含硫黄複素環誘導体 |
| JP2011524894A (ja) | 2008-06-18 | 2011-09-08 | ファイザー・リミテッド | ニコチンアミド誘導体 |
| CN102143957B (zh) | 2008-07-03 | 2014-08-20 | 西特里斯药业公司 | 作为沉默调节蛋白调节剂的苯并咪唑类和相关的类似物 |
| RU2523448C2 (ru) * | 2008-08-04 | 2014-07-20 | СиЭйчДиАй ФАУНДЕЙШН, Инк, | Ингибиторы кинуренин-3-монооксигеназы |
| US8193363B2 (en) * | 2008-08-29 | 2012-06-05 | Astrazeneca Ab | Compounds suitable as precursors to compounds that are useful for imaging amyloid deposits |
| UY32138A (es) * | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| EP3924343A1 (en) | 2008-09-26 | 2021-12-22 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010047372A1 (ja) | 2008-10-22 | 2010-04-29 | 塩野義製薬株式会社 | Ｂａｃｅ１阻害活性を有する２－アミノピリミジン－４－オンおよび２－アミノピリジン誘導体 |
| AU2009309007A1 (en) | 2008-10-29 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010051206A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| TW201020244A (en) | 2008-11-14 | 2010-06-01 | Astrazeneca Ab | New compounds |
| CN101619058A (zh) * | 2009-01-08 | 2010-01-06 | 上海交通大学 | 一种苯并咪唑-4-酰胺型衍生物 |
| US20100278835A1 (en) * | 2009-03-10 | 2010-11-04 | Astrazeneca Uk Limited | Novel compounds 660 |
| WO2010112124A1 (en) | 2009-04-02 | 2010-10-07 | Merck Patent Gmbh | Autotaxin inhibitors |
| AU2010241929A1 (en) * | 2009-04-27 | 2011-10-06 | High Point Pharmaceuticals, Llc | Substituted imidazo[1,2-a]pyridine derivatives, pharmaceutical compositions, and methods of use as beta-secretase inhibitors |
| JP2012525389A (ja) * | 2009-04-27 | 2012-10-22 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 置換イソキノリン誘導体、医薬組成物、及びβ−セクレターゼ阻害剤としての使用方法 |
| EP2594557B1 (en) * | 2009-05-28 | 2016-08-10 | Novartis AG | Substituted aminopropionic derivatives as neprilysin inhibitors |
| EP2281824A1 (en) | 2009-08-07 | 2011-02-09 | Noscira, S.A. | Furan-imidazolone derivatives, for the treatment of cognitive, neurodegenerative or neuronal diseases or disorders |
| JP5663482B2 (ja) * | 2009-08-31 | 2015-02-04 | イハラケミカル工業株式会社 | ピリミジニルアセトニトリル誘導体の製造方法及びその合成中間体 |
| US9340555B2 (en) | 2009-09-03 | 2016-05-17 | Allergan, Inc. | Compounds as tyrosine kinase modulators |
| EP2473513B1 (en) | 2009-09-03 | 2019-06-05 | Allergan, Inc. | Compounds as tyrosine kinase modulators |
| US8541404B2 (en) | 2009-11-09 | 2013-09-24 | Elexopharm Gmbh | Inhibitors of the human aldosterone synthase CYP11B2 |
| JPWO2011071135A1 (ja) | 2009-12-11 | 2013-04-22 | 塩野義製薬株式会社 | オキサジン誘導体 |
| MX2012006994A (es) | 2009-12-18 | 2012-07-03 | Mitsubishi Tanabe Pharma Corp | Agente antiplaquetas novedoso. |
| JP2013517246A (ja) | 2010-01-15 | 2013-05-16 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | γセクレターゼ調節物質としての新規置換二環トリアゾール誘導体 |
| JP2013518046A (ja) | 2010-01-25 | 2013-05-20 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | 特定のキヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 |
| CA2786314A1 (en) | 2010-02-25 | 2011-09-01 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| EP2549874A4 (en) * | 2010-03-23 | 2013-10-02 | High Point Pharmaceuticals Llc | SUBSTITUTED IMIDAZOLE [1,2-B] PYRIDAZINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE AS BETA-SECRETASE INHIBITORS |
| MX2013001313A (es) | 2010-08-05 | 2013-06-13 | Amgen Inc | Compuestos de bencimidazol y azabencimidazol que inhiben la cinasa del linfoma anaplasico. |
| JP5766198B2 (ja) | 2010-10-29 | 2015-08-19 | 塩野義製薬株式会社 | 縮合アミノジヒドロピリミジン誘導体 |
| CA2816285A1 (en) | 2010-10-29 | 2012-05-03 | Shionogi & Co., Ltd. | Naphthyridine derivative |
| JP2013542973A (ja) | 2010-11-22 | 2013-11-28 | ノスシラ、ソシエダッド、アノニマ | 神経変性疾患または神経変性状態を治療するためのビピリジンスルホンアミド誘導体 |
| WO2012147763A1 (ja) | 2011-04-26 | 2012-11-01 | 塩野義製薬株式会社 | オキサジン誘導体およびそれを含有するｂａｃｅ１阻害剤 |
| SI2723732T1 (sl) | 2011-06-22 | 2017-05-31 | Purdue Pharma Lp One Stamford Forum | Antagonisti trpv1, vključno z dihidroksi substituentom, in njihova uporaba |
| EA023045B1 (ru) | 2011-07-15 | 2016-04-29 | Янссен Фармасьютикалз, Инк. | Новые замещенные производные индола в качестве модуляторов гамма-секретазы |
| PL2746265T3 (pl) * | 2011-08-18 | 2016-04-29 | Nippon Shinyaku Co Ltd | POCHODNA HETEROCYKLICZNA JAKO INHIBITOR MIKROSOMALNEJ SYNTAZY PROSTAGLANDYNY E (mPGEs) |
| HRP20170928T1 (hr) | 2011-08-30 | 2017-09-22 | Chdi Foundation, Inc. | Inhibitori kinurenin-3-monooksigenaze, farmaceutski pripravci, i postupci za njihovu upotrebu |
| MX2014002459A (es) | 2011-08-30 | 2014-04-10 | Chdi Foundation Inc | Inhibidores de quinurenina-3-monooxigenasa, composiciones farmaceuticas y metodos de uso de los mismos. |
| CN104254330A (zh) * | 2012-01-09 | 2014-12-31 | X-Rx公司 | 具有激酶抑制活性的tryptoline衍生物及其用途 |
| WO2013104577A1 (en) | 2012-01-11 | 2013-07-18 | Acesion Pharma Aps | Benzimidazolyl-acetamide derivatives useful as potassium channel modulators |
| US9056874B2 (en) | 2012-05-04 | 2015-06-16 | Novartis Ag | Complement pathway modulators and uses thereof |
| NZ702611A (en) | 2012-05-16 | 2016-10-28 | Cellzome Ltd | Substituted 3, 4 - dihydro - 2h - pyrido [1, 2 -a] pyrazine - 1, 6 - dione derivatives useful for the treatment of (inter alia) alzheimer’s disease |
| CN103772376B (zh) * | 2012-10-24 | 2017-01-11 | 中国医学科学院医药生物技术研究所 | 取代的苯并-1,3-杂唑类化合物、其制备方法及用途 |
| US9540359B2 (en) | 2012-10-24 | 2017-01-10 | Shionogi & Co., Ltd. | Dihydrooxazine or oxazepine derivatives having BACE1 inhibitory activity |
| JP6275161B2 (ja) | 2012-12-20 | 2018-02-07 | ヤンセン ファーマシューティカ エヌ．ベー． | γセクレターゼ調節剤としての新規な三環式３，４−ジヒドロ−２Ｈ−ピリド［１，２−ａ］ピラジン−１，６−ジオン誘導体 |
| HK1212346A1 (en) | 2013-01-17 | 2016-06-10 | Janssen Pharmaceutica Nv | Novel substituted pyrido-piperazinone derivatives as gamma secretase modulators |
| JP6387391B2 (ja) | 2013-03-14 | 2018-09-05 | ノバルティス アーゲー | 眼科疾患の処置に有用な補体因子Ｂ阻害剤としての２−（１Ｈ−インドール−４−イルメチル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン−６−カルボニトリル誘導体 |
| CA2915622C (en) * | 2013-06-21 | 2020-08-18 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| SG11201510409QA (en) | 2013-06-21 | 2016-01-28 | Zenith Epigenetics Corp | Novel bicyclic bromodomain inhibitors |
| US9855271B2 (en) | 2013-07-31 | 2018-01-02 | Zenith Epigenetics Ltd. | Quinazolinones as bromodomain inhibitors |
| JP2016535042A (ja) | 2013-10-30 | 2016-11-10 | ノバルティス アーゲー | ２−ベンジル−ベンゾイミダゾール補体因子ｂ阻害剤およびその使用 |
| US9844542B2 (en) | 2013-11-19 | 2017-12-19 | Vanderbilt University | Substituted imidazopyridine and triazolopyridine compounds as negative allosteric modulators of mGluR5 |
| US10562897B2 (en) | 2014-01-16 | 2020-02-18 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| CA2939021C (en) | 2014-02-11 | 2022-07-12 | Bayer Pharma Aktiengesellschaft | Benzimidazol-2-amines as midh1 inhibitors |
| CN106573897B (zh) | 2014-02-11 | 2019-09-24 | 拜耳制药股份公司 | 作为mIDH1抑制剂的苯并咪唑-2-胺 |
| CR20170061A (es) | 2014-07-17 | 2017-07-17 | Chdi Foundation Inc | Métodos y composiciones para el tratamiento de trastornos relacionados con vih |
| GB201415569D0 (en) * | 2014-09-03 | 2014-10-15 | C4X Discovery Ltd | Therapeutic Compounds |
| CN107108554B (zh) | 2014-10-23 | 2020-11-06 | 德国癌症研究中心 | 作为midh1抑制剂用于治疗肿瘤的1-环己基-2-苯基氨基苯并咪唑 |
| EP3209646B1 (en) | 2014-10-23 | 2020-07-22 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Benzimidazol-2-amines as midh1 inhibitors |
| EP3227281A4 (en) | 2014-12-01 | 2018-05-30 | Zenith Epigenetics Ltd. | Substituted pyridinones as bromodomain inhibitors |
| HK1245248B (en) | 2014-12-11 | 2020-05-15 | 恒翼生物医药(上海)股份有限公司 | Substituted heterocycles as bromodomain inhibitors |
| HK1245247A1 (zh) | 2014-12-17 | 2018-08-24 | 恒翼生物医药科技(上海)有限公司 | 溴结构域的抑制剂 |
| CN107810176B (zh) | 2015-06-08 | 2020-10-16 | 德国癌症研究公共权益基金会 | 作为mIDH1抑制剂的N-薄荷基苯并咪唑类化合物 |
| CA2992364A1 (en) | 2015-07-16 | 2017-01-19 | Bayer Pharma Aktiengesellschaft | 5-hydroxyalkylbenzimidazoles as midh1 inhibitors |
| AU2016323612B2 (en) * | 2015-09-18 | 2021-04-08 | Merck Patent Gmbh | Heteroaryl compounds as IRAK inhibitors and uses thereof |
| MX386726B (es) | 2015-09-18 | 2025-03-19 | Merck Patent Gmbh | Compuestos de heteroarilo como inhibidores de cinasas asociadas al receptor de interleucina 1 (irak) y sus usos. |
| CN108884053B (zh) * | 2015-12-15 | 2022-01-04 | 斯坦福大学托管董事会 | 预防和/或治疗与衰老有关的认知障碍和神经炎症的方法 |
| WO2017102091A1 (en) | 2015-12-18 | 2017-06-22 | Bayer Pharma Aktiengesellschaft | Heteroarylbenzimidazole compounds |
| GB201601703D0 (en) | 2016-01-29 | 2016-03-16 | C4X Discovery Ltd | Therapeutic compounds |
| WO2017207534A1 (en) | 2016-06-03 | 2017-12-07 | Bayer Pharma Aktiengesellschaft | Substituted heteroarylbenzimidazole compounds |
| GB201619694D0 (en) * | 2016-11-22 | 2017-01-04 | Entpr Therapeutics Ltd | Compounds |
| CN106986809B (zh) * | 2016-12-02 | 2020-03-24 | 广东省微生物研究所（广东省微生物分析检测中心） | 一种5-溴-6-氯-3-吲哚辛酯的合成方法 |
| SG11202001337XA (en) * | 2017-08-21 | 2020-03-30 | Merck Patent Gmbh | Bezimidazole derivatives as adenosine receptor antagonists |
| WO2019162323A1 (en) * | 2018-02-21 | 2019-08-29 | Boehringer Ingelheim International Gmbh | New benzimidazole compounds and derivatives as egfr inhibitors |
| CN109400528B (zh) * | 2018-12-18 | 2022-03-15 | 深圳科兴药业有限公司 | 一种可博美的合成方法 |
| JP2022540200A (ja) | 2019-07-11 | 2022-09-14 | エスケイプ・バイオ・インコーポレイテッド | Ｌｒｒｋ２阻害剤としてのインダゾールおよびアザインダゾール |
| AU2021342783A1 (en) * | 2020-09-17 | 2023-05-18 | Novartis Ag | Compounds and compositions as sppl2a inhibitors |
| US12227475B2 (en) * | 2021-04-27 | 2025-02-18 | X-Biotix Therapeutics, Inc. | Aza-heterocyclyl carboxamide and related compounds and their use in treating medical conditions |
| TN2023000286A1 (en) | 2021-06-14 | 2025-07-02 | Scorpion Therapeutics Inc | Urea derivatives which can be used to treat cancer |
| CN113387959B (zh) * | 2021-06-24 | 2023-05-05 | 烟台理工学院 | 一种噻吩并[3,2-c]吡啶-6-羧酸甲酯的合成方法 |
| WO2024211834A1 (en) * | 2023-04-05 | 2024-10-10 | Moma Therapeutics, Inc. | Biaryl derivatives and related uses |
Family Cites Families (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3401173A (en) * | 1966-04-05 | 1968-09-10 | Smith Kline French Lab | Heterocyclic acylaminobenzimidazoles |
| GB1122957A (en) | 1965-06-07 | 1968-08-07 | Smith Kline French Lab | Substituted benzimidazoles and anthelmintic compositions containing them |
| US3336191A (en) * | 1966-03-11 | 1967-08-15 | Smith Kline French Lab | Anthelmintic 2-amidobenzimidazoles |
| US5552426A (en) * | 1994-04-29 | 1996-09-03 | Eli Lilly And Company | Methods for treating a physiological disorder associated with β-amyloid peptide |
| US5942400A (en) * | 1995-06-07 | 1999-08-24 | Elan Pharmaceuticals, Inc. | Assays for detecting β-secretase |
| US6329163B1 (en) * | 1995-06-07 | 2001-12-11 | Elan Pharmaceuticals, Inc. | Assays for detecting β-secretase inhibition |
| US5744346A (en) * | 1995-06-07 | 1998-04-28 | Athena Neurosciences, Inc. | β-secretase |
| GB9600142D0 (en) * | 1996-01-05 | 1996-03-06 | Wellcome Found | Chemical compounds |
| CA2258728C (en) * | 1996-06-19 | 2011-09-27 | Rhone Poulenc Rorer Limited | Substituted azabicylic compounds and their use as inhibitors of the production of tnf and cyclic amp phosphodiesterase |
| HUP0000189A3 (en) * | 1996-11-15 | 2002-01-28 | Darwin Discovery Ltd Milton Ro | Bicyclic aryl carboxamides pharmaceutical compositions containing them and their therapeutic use |
| AUPO395396A0 (en) * | 1996-12-02 | 1997-01-02 | Fujisawa Pharmaceutical Co., Ltd. | Benzamide derivatives |
| DE69833224T2 (de) * | 1997-11-10 | 2006-09-28 | Bristol-Myers Squibb Co. | Benzothiazole als protein tyrosin-kinase inhibitoren |
| US6699671B1 (en) * | 1998-09-24 | 2004-03-02 | Pharmacia & Upjohn Company | Alzheimer's disease secretase, APP substrates therefor, and uses therefor |
| US20040234976A1 (en) * | 1998-09-24 | 2004-11-25 | Gurney Mark E. | Alzheimer's disease secretase, app substrates therefor, and uses therefor |
| DK1115874T3 (da) * | 1998-09-24 | 2009-04-20 | Pharmacia & Upjohn Co Llc | Alzheimer's sygdom-sekretase |
| US6245884B1 (en) * | 1998-10-16 | 2001-06-12 | Vivian Y. H. Hook | Secretases related to alzheimer's dementia |
| DK1133477T3 (da) * | 1998-11-27 | 2004-06-21 | Abbott Gmbh & Co Kg | Substituerede benzimidazoler og deres anvendelse som parpinhibitorer |
| AU4000900A (en) * | 1999-02-10 | 2000-08-29 | Elan Pharmaceuticals, Inc. | Beta-secretase enzyme compositions and methods |
| DE19920936A1 (de) * | 1999-05-07 | 2000-11-09 | Basf Ag | Heterozyklisch substituierte Benzimidazole, deren Herstellung und Anwendung |
| SK286857B6 (sk) * | 1999-06-23 | 2009-06-05 | Sanofi-Aventis Deutschland Gmbh | Substituované benzimidazoly, spôsob ich prípravy, ich použitie a liečivo, ktoré ich obsahuje |
| DE60013836T2 (de) | 1999-06-28 | 2006-01-19 | Janssen Pharmaceutica N.V. | Replikationsinhibitoren des respiratorischen synzytialvirus |
| WO2001000663A2 (en) * | 1999-06-28 | 2001-01-04 | Oklahoma Medical Research Foundation | Catalytically active recombinant memapsin and methods of use thereof |
| AU7314200A (en) * | 1999-09-17 | 2001-04-24 | Yamanouchi Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| US6506769B2 (en) * | 1999-10-06 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic compounds useful as inhibitors of tyrosine kinases |
| MXPA02003364A (es) | 1999-10-06 | 2002-08-23 | Boehringer Ingelheim Pharma | Compuestos heterociclicos utiles como inhibidores de las cinasas de tirosina. |
| US20030143708A1 (en) * | 1999-12-29 | 2003-07-31 | Blatt La Wrence | Method and reagent for the treatment of alzheimer's disease |
| US20030092003A1 (en) * | 1999-12-29 | 2003-05-15 | Ribozyme Pharmaceuticals, Inc. | Method and reagent for the treatment of Alzheimer's disease |
| EP1265849B1 (en) * | 2000-03-23 | 2006-10-25 | Elan Pharmaceuticals, Inc. | Compounds and methods to treat alzheimer's disease |
| CN1251671C (zh) * | 2000-05-19 | 2006-04-19 | 武田药品工业株式会社 | β分泌酶抑制剂 |
| US7087632B2 (en) | 2001-03-05 | 2006-08-08 | Transtech Pharma, Inc. | Benzimidazole derivatives as therapeutic agents |
| US6713276B2 (en) * | 2000-06-28 | 2004-03-30 | Scios, Inc. | Modulation of Aβ levels by β-secretase BACE2 |
| US6846813B2 (en) * | 2000-06-30 | 2005-01-25 | Pharmacia & Upjohn Company | Compounds to treat alzheimer's disease |
| PE20020276A1 (es) * | 2000-06-30 | 2002-04-06 | Elan Pharm Inc | COMPUESTOS DE AMINA SUSTITUIDA COMO INHIBIDORES DE ß-SECRETASA PARA EL TRATAMIENTO DE ALZHEIMER |
| ATE397077T1 (de) * | 2000-07-19 | 2008-06-15 | Pharmacia & Upjohn Co Llc | Substraten und nachweise zur wirksamkeit von beta-secretase |
| CA2417635C (en) * | 2000-08-11 | 2008-02-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic compounds useful as inhibitors of tyrosine kinases |
| US7630838B2 (en) * | 2000-09-22 | 2009-12-08 | American Home Products Corporation | Method for identifying agents that interact with beta-site APP cleaving enzyme (BACE) |
| AU2002243391A1 (en) * | 2000-10-27 | 2002-06-24 | The Johns Hopkins University School Of Medicine | Beta-secretase transgenic organisms, anti-beta-secretase antibodies, and methods of use thereof |
| ATE330950T1 (de) * | 2000-12-13 | 2006-07-15 | Wyeth Corp | Heterocyclische sulfonamide als inhibitoren der beta-amyloid-produktion |
| GB0101313D0 (en) * | 2001-01-18 | 2001-02-28 | Glaxo Group Ltd | Assay |
| HUP0304047A2 (hu) * | 2001-02-02 | 2004-04-28 | Pharmacopeia, Inc. | 3,4-Diszubsztituált ciklobutén-1,2-dionok mint CXC kemokin receptor antagonisták és ezeket tartalmazó gyógyszerkészítmények |
| EP1233021A3 (en) * | 2001-02-20 | 2002-11-20 | Pfizer Products Inc. | An inhibitor of Beta amyloid cleavage enzyme |
| US7309811B2 (en) * | 2001-02-23 | 2007-12-18 | Elan Pharmaceuticals, Inc | Transgenic mice knockouts of BACE-1 |
| JP2004532826A (ja) * | 2001-03-19 | 2004-10-28 | スローン−ケッタリング インスティトゥート フォー カンサー リサーチ | （ｓ，ｒ，ｒ）−（−）−アクチノニンおよびそのアナログの不斉合成、ならびにそれらの使用 |
| US20040097547A1 (en) * | 2001-04-16 | 2004-05-20 | Taveras Arthur G. | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| WO2002088101A2 (en) * | 2001-04-27 | 2002-11-07 | Vertex Pharmaceuticals Incorporated | Inhibitors of bace |
| FR2824825B1 (fr) * | 2001-05-15 | 2005-05-06 | Servier Lab | Nouveaux derives d'alpha-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6562783B2 (en) * | 2001-05-30 | 2003-05-13 | Neurologic, Inc. | Phosphinylmethyl and phosphorylmethyl succinic and glutauric acid analogs as β-secretase inhibitors |
| BR0210683A (pt) * | 2001-06-25 | 2004-07-20 | Elan Pharm Inc | Métodos para tratar ou prevenir mal de alzheimer e uma doença distinguida por depósitos de beta-amilóide sobre ou no cérebro, para tratar um paciente que tem, ou para evitar que o paciente adquira uma doença ou condição, para inibir a atividade de beta-secretase, a clivagem de um isotipo de proteìna de precursor de amilóide e a produção de peptìdeo beta-amilóide em uma célula e de uma placa de beta-amilóide em um animal e para produzir um complexo de beta-secretase, uso de um composto e composição |
| US20030093356A1 (en) * | 2001-07-06 | 2003-05-15 | Assetsight, Inc. | Method for issuing a derivative contract |
| EP1404328A1 (en) * | 2001-07-10 | 2004-04-07 | Elan Pharmaceuticals, Inc. | Alpha-hydroxyamide statine derivatives for the treatment of alzheimer's disease |
| US20030109559A1 (en) * | 2001-07-11 | 2003-06-12 | Andrea Gailunas | N-(3-amino-2-hydroxy-propyl)substituted alkylamide compounds |
| JP2005506979A (ja) * | 2001-08-28 | 2005-03-10 | ファルマシア アンド アップジョン カンパニー リミティド ライアビリティー カンパニー | オキソ置換及びヒドロキシ置換炭化水素のキナルドイル−アミン誘導体を使用するアルツハイマー病の治療方法 |
| GB0123379D0 (en) * | 2001-09-28 | 2001-11-21 | Lorantis Ltd | Modulators |
| ATE511840T1 (de) * | 2001-10-09 | 2011-06-15 | Amgen Inc | Imidazolderivate als entzündungshemmende mittel |
| WO2003032984A1 (en) | 2001-10-19 | 2003-04-24 | Ortho-Mcneil Pharmaceutical,Inc. | 2-phenyl benzimidazoles and imidazo-[4,5]-pyridines as cdsi/chk2-inhibitors and adjuvants to chemotherapy or radiation therapy in the treatment of cancer |
| EP1440072A4 (en) * | 2001-10-30 | 2005-02-02 | Conforma Therapeutic Corp | PURINE ANALOGS HAVING HSP90 INHIBITORY ACTIVITY |
| HRP20040518A2 (hr) * | 2001-11-08 | 2007-08-31 | Elan Pharmaceuticals | Derivati n,n-supstituiranog-1,3-diamino-2-hidroksipropana |
| JP2005509003A (ja) * | 2001-11-09 | 2005-04-07 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | タンパク質キナーゼインヒビターとして有用なベンゾイミダゾール化合物 |
| US6620811B2 (en) * | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
| CH698246B1 (de) * | 2001-12-20 | 2009-06-30 | Hoffmann La Roche | Test zur Identifizierung von Inhibitoren von Beta-Sekretasen. |
| FR2833948B1 (fr) * | 2001-12-21 | 2004-02-06 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et leur utilisation en tant que medicament |
| WO2003072733A2 (en) * | 2002-02-21 | 2003-09-04 | Pharmacia & Upjohn Company | Modified bace |
| DE60325519D1 (de) * | 2002-03-01 | 2009-02-12 | Hoffmann La Roche | Doppel-transgenisches, nicht-humanes Säugertiermodell für die Alzheimer Krankheit |
| JP4481011B2 (ja) * | 2002-03-05 | 2010-06-16 | トランス テック ファーマ，インコーポレイテッド | リガンドのｒａｇｅとの相互作用を阻害する単環式および二環式アゾール誘導体 |
| US20040014194A1 (en) * | 2002-03-27 | 2004-01-22 | Schering Corporation | Beta-secretase crystals and methods for preparing and using the same |
| EP1502916A4 (en) | 2002-04-16 | 2006-05-31 | Teijin Ltd | Piperidin derivatives with CCR3-antagonism |
| JP2005289816A (ja) * | 2002-05-14 | 2005-10-20 | Banyu Pharmaceut Co Ltd | ベンズイミダゾール誘導体 |
| US7049333B2 (en) * | 2002-06-04 | 2006-05-23 | Sanofi-Aventis Deutschland Gmbh | Substituted thiophenes: compositions, processes of making, and uses in disease treatment and diagnosis |
| WO2003103598A2 (en) * | 2002-06-07 | 2003-12-18 | University Of North Carolina At Chapel Hill | Amidine derivatives for treating amyloidosis |
| ES2277088T3 (es) | 2002-06-13 | 2007-07-01 | Vertex Pharmaceuticals Incorporated | Derivados del acido 2-ureido-6-heteroaril-3h-benzoimidazol-4-carboxilico y compuestos relacionados como inhibidores de girasa y/o topoisomerasa iv para el tratamiento de infecciones bacterianas. |
| US20040034078A1 (en) * | 2002-06-14 | 2004-02-19 | Agouron Pharmaceuticals, Inc. | Benzimidazole inhibitors of poly(ADP-ribosyl) polymerase |
| US7115652B2 (en) * | 2002-06-17 | 2006-10-03 | Sunesis Pharmaceuticals, Inc. | Aspartyl protease inhibitors |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| EP1388341A1 (en) * | 2002-08-07 | 2004-02-11 | Aventis Pharma Deutschland GmbH | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| KR20050037585A (ko) * | 2002-08-23 | 2005-04-22 | 카이론 코포레이션 | 벤지미다졸 퀴놀리논 및 그들의 사용 |
| US7294642B2 (en) * | 2002-09-06 | 2007-11-13 | Elan Pharmaceuticals, Inc. | 1,3-Diamino-2-hydroxypropane pro-drug derivatives |
| UY27967A1 (es) * | 2002-09-10 | 2004-05-31 | Pfizer | Acetil 2-hindroxi-1,3-diaminoalcanos |
| WO2004026264A2 (en) * | 2002-09-20 | 2004-04-01 | Genelabs Technologies, Inc. | Novel aromatic compounds possessing antifungal or antibacterial activity |
| JP2006508166A (ja) * | 2002-11-27 | 2006-03-09 | イーラン ファーマスーティカルズ、インコーポレイテッド | 置換尿素及びカルバメート |
| WO2004084830A2 (en) * | 2003-03-21 | 2004-10-07 | Buck Institute | Method for treating alzheimer’s dementia |
| US20050176792A1 (en) * | 2004-01-14 | 2005-08-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Ketone substituted benzimidazole compounds |
| US7470712B2 (en) * | 2004-01-21 | 2008-12-30 | Bristol-Myers Squibb Company | Amino-benzazoles as P2Y1 receptor inhibitors |
| WO2006099379A2 (en) * | 2005-03-14 | 2006-09-21 | Transtech Pharma, Inc. | Benzazole derivatives, compositions, and methods of use as b-secretase inhibitors |
| CN102633783A (zh) * | 2006-02-10 | 2012-08-15 | 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 |
-
2006
- 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 CN CN2006800084176A patent/CN101142194B/zh not_active Expired - Fee Related
- 2006-03-14 EP EP06738139A patent/EP1863771B1/en active Active
- 2006-03-14 CA CA2600570A patent/CA2600570C/en not_active Expired - Fee Related
- 2006-03-14 US US11/374,723 patent/US20060223849A1/en not_active Abandoned
- 2006-03-14 ZA ZA200707896A patent/ZA200707896B/xx unknown
- 2006-03-14 ES ES06738139T patent/ES2400287T3/es active Active
- 2006-03-14 EP EP12150487A patent/EP2457901A1/en not_active Withdrawn
- 2006-03-14 NZ NZ561029A patent/NZ561029A/en not_active IP Right Cessation
- 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 JP JP2008501948A patent/JP5066514B2/ja not_active Expired - Fee Related
- 2006-03-14 US US11/885,096 patent/US7893267B2/en not_active Expired - Fee Related
-
2007
- 2007-08-27 IL IL185541A patent/IL185541A/en not_active IP Right Cessation
-
2009
- 2009-05-13 ZA ZA2009/03300A patent/ZA200903300B/en unknown
-
2010
- 2010-11-19 US US12/950,718 patent/US8598353B2/en not_active Expired - Fee Related
-
2011
- 2011-11-24 JP JP2011256487A patent/JP2012046541A/ja not_active Ceased
-
2012
- 2012-10-25 IL IL222698A patent/IL222698A0/en unknown
-
2013
- 2013-10-28 US US14/064,737 patent/US8946259B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008533151A5 (enExample) | ||
| CN105492439B (zh) | 作为溴结构域抑制剂的取代的双环化合物 | |
| CA2600570A1 (en) | Benzazole derivatives, compositions, and methods of use as .beta.-secretase inhibitors | |
| JP6436205B2 (ja) | キノリン誘導体 | |
| JP6708130B2 (ja) | キノリン誘導体 | |
| RU2375046C2 (ru) | Твердый состав с улучшенными растворимостью и стабильностью и способ его получения | |
| JP2008524246A5 (enExample) | ||
| JP2009521399A5 (enExample) | ||
| ZA200302918B (en) | Combination use of acetylcholinesterase inhibitors and gabaa inverse agonists for the treatment of cognitive disorders. | |
| HRP20161116T1 (hr) | NOVI DERIVATI CIKLOHEKSILAMINA KOJI DJELUJU KAO AGONISTI β2 ADRENERGIČKOG RECEPTORA I ANTAGONISTI MUSKARINSKOG ACETILKOLINSKOG RECEPTORA M3 | |
| JP2007513915A5 (enExample) | ||
| JP2011500638A5 (enExample) | ||
| AU2007329480A1 (en) | Indazole compounds | |
| JP2013523792A (ja) | Ｐｄｅ４阻害剤及びｅｐ４受容体アンタゴニストを含有する医薬の組み合わせ | |
| HRP20140593T1 (hr) | Derivati 1,3-disupstituiranih imidazolidin-2-ona kao cyp 17-inhibitori | |
| HUP0303460A2 (hu) | IgE-Módosító és sejtburjánzásgátló hatású benzimidazolok és ezeket tartalmazó gyógyszerkészítmények | |
| KR20140117684A (ko) | 단백질 키나제 억제제로서의 헤테로아릴 화합물 및 조성물 | |
| JP2020531454A5 (enExample) | ||
| TW201900637A (zh) | N-取代吲哚衍生物 | |
| CN104023715A (zh) | 激酶抑制剂的副作用降低剂 | |
| RU2005136383A (ru) | Применение дипиридамола или мопидамола для лечения и предупреждения тромбоэмболических заболеваний и нарушений, вызываемыхизбыточным образованием и/или повышенным уровнем экспрессии тромбиновых рецепторов | |
| CN111727044A (zh) | 用于治疗癌症或炎性疾病的杂二环羧酸 | |
| JP2025519119A (ja) | Ｍｅｋ阻害剤及びその使用 | |
| PT1487424E (pt) | 4-(4-metilpiperazin-1-ilmetil)-n-[4-metil-3-(4-piridin-3-il)pirimidin-2-il-amino)fenil]-benzamida para o tratamento doenças mediadas por ang ii | |
| CA2730225A1 (en) | Use of pyrimidylaminobenzamide derivatives for the treatment of fibrosis |