HRP20120174T1 - Derivat policikličnog cinamida - Google Patents
Derivat policikličnog cinamida Download PDFInfo
- Publication number
- HRP20120174T1 HRP20120174T1 HR20120174T HRP20120174T HRP20120174T1 HR P20120174 T1 HRP20120174 T1 HR P20120174T1 HR 20120174 T HR20120174 T HR 20120174T HR P20120174 T HRP20120174 T HR P20120174T HR P20120174 T1 HRP20120174 T1 HR P20120174T1
- Authority
- HR
- Croatia
- Prior art keywords
- group
- methyl
- phenyl
- methoxy
- vinyl
- Prior art date
Links
- -1 Polycyclic cinnamide derivative Chemical class 0.000 title claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 100
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 75
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 23
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract 18
- 125000005843 halogen group Chemical group 0.000 claims abstract 18
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 150000003839 salts Chemical class 0.000 claims abstract 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 13
- 125000003118 aryl group Chemical group 0.000 claims abstract 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 10
- 125000003277 amino group Chemical group 0.000 claims abstract 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 4
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims abstract 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims abstract 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
- 229920002554 vinyl polymer Polymers 0.000 claims 72
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 69
- AQWOIRBQLOOZGX-UHFFFAOYSA-N triazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=NN21 AQWOIRBQLOOZGX-UHFFFAOYSA-N 0.000 claims 13
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 4
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- JONHOTQRQYAIBY-FNORWQNLSA-N 2-[(e)-2-[3-fluoro-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=NC(C)=CN1C(C(=C1)F)=CC=C1\C=C\C1=NN2CCCC(C=3C=C(F)C(F)=C(F)C=3)C2=N1 JONHOTQRQYAIBY-FNORWQNLSA-N 0.000 claims 2
- YDESGKZGVHWNFJ-SOFGYWHQSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(2,4,6-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=C(F)C=C(F)C=C1F YDESGKZGVHWNFJ-SOFGYWHQSA-N 0.000 claims 2
- BIPXGTARIHCGIF-GQCTYLIASA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(2,4,6-trifluorophenyl)-6,8-dihydro-5h-[1,2,4]triazolo[5,1-c][1,4]oxazine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCO2)N=C1C2C1=C(F)C=C(F)C=C1F BIPXGTARIHCGIF-GQCTYLIASA-N 0.000 claims 2
- PUSRVRWCIBTGIV-SOFGYWHQSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC(F)=C(F)C(F)=C1 PUSRVRWCIBTGIV-SOFGYWHQSA-N 0.000 claims 2
- ICHANYDVCWFHTG-GQCTYLIASA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(3,4,5-trifluorophenyl)-6,8-dihydro-5h-[1,2,4]triazolo[5,1-c][1,4]oxazine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCO2)N=C1C2C1=CC(F)=C(F)C(F)=C1 ICHANYDVCWFHTG-GQCTYLIASA-N 0.000 claims 2
- NHGUPYCBODUGTD-WUXMJOGZSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(4-methoxyphenyl)-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound C1=CC(OC)=CC=C1C1(O)C2=NC(\C=C\C=3C=C(OC)C(=CC=3)N3C=C(C)N=C3)=NN2CCC1 NHGUPYCBODUGTD-WUXMJOGZSA-N 0.000 claims 2
- MBVUBIYEGJZNOP-WUXMJOGZSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-[4-(trifluoromethoxy)phenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC=C(OC(F)(F)F)C=C1 MBVUBIYEGJZNOP-WUXMJOGZSA-N 0.000 claims 2
- JNATWVFWZQZUQW-ONNFQVAWSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-[4-(trifluoromethoxy)phenyl]-6,8-dihydro-5h-[1,2,4]triazolo[5,1-c][1,4]oxazine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCO2)N=C1C2C1=CC=C(OC(F)(F)F)C=C1 JNATWVFWZQZUQW-ONNFQVAWSA-N 0.000 claims 2
- UIVXXXWJGLQGHY-WYMLVPIESA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-naphthalen-1-yl-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound COC1=CC(\C=C\C2=NN3C(C(CCC3)(O)C=3C4=CC=CC=C4C=CC=3)=N2)=CC=C1N1C=NC(C)=C1 UIVXXXWJGLQGHY-WYMLVPIESA-N 0.000 claims 2
- XRGGUPKWDJNMOH-NDENLUEZSA-N 2-[(z)-1-fluoro-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(4-fluorophenyl)-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C(/F)C(=N1)N=C2N1CCCC2(O)C1=CC=C(F)C=C1 XRGGUPKWDJNMOH-NDENLUEZSA-N 0.000 claims 2
- ONJOJETYYKOPEL-SOFGYWHQSA-N 3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1CCC2)=NN=C1C2C1=CC(F)=C(F)C(F)=C1 ONJOJETYYKOPEL-SOFGYWHQSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- CRJMPGQRVVAATK-VZUCSPMQSA-N 5-[1-(4-fluorophenyl)ethyl]-3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1h-1,2,4-triazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1)=NN=C1C(C)C1=CC=C(F)C=C1 CRJMPGQRVVAATK-VZUCSPMQSA-N 0.000 claims 2
- OXIXYQXOIBERHD-ZRDIBKRKSA-N 8-(2-bromophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC=CC=C1Br OXIXYQXOIBERHD-ZRDIBKRKSA-N 0.000 claims 2
- HOAFPHQBDYDYGC-ONNFQVAWSA-N 8-(4-bromophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,8-dihydro-5h-[1,2,4]triazolo[5,1-c][1,4]oxazine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCO2)N=C1C2C1=CC=C(Br)C=C1 HOAFPHQBDYDYGC-ONNFQVAWSA-N 0.000 claims 2
- SXOHBPKLSIFMIQ-WUXMJOGZSA-N 8-(4-chlorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC=C(Cl)C=C1 SXOHBPKLSIFMIQ-WUXMJOGZSA-N 0.000 claims 2
- RGMAZZSGAUHFKY-VZUCSPMQSA-N 8-(4-chlorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(O)C1=CC=C(Cl)C=C1 RGMAZZSGAUHFKY-VZUCSPMQSA-N 0.000 claims 2
- AMNONJZOSVUDGL-WUXMJOGZSA-N 8-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-methyl-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(C)C1=CC=C(F)C=C1 AMNONJZOSVUDGL-WUXMJOGZSA-N 0.000 claims 2
- LLDMVSBMTOLQLK-VZUCSPMQSA-N 8-fluoro-8-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(F)C1=CC=C(F)C=C1 LLDMVSBMTOLQLK-VZUCSPMQSA-N 0.000 claims 2
- OONLZXCNCKIBQF-SOFGYWHQSA-N 8-methoxy-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(3,4,5-trifluorophenyl)-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(OC)C1=CC(F)=C(F)C(F)=C1 OONLZXCNCKIBQF-SOFGYWHQSA-N 0.000 claims 2
- HHZBYCZWQLBOCA-NTUHNPAUSA-N 8-methoxy-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(4-methoxyphenyl)-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC(OC)=CC=C1C1(OC)C2=NC(\C=C\C=3C=C(OC)C(=CC=3)N3C=C(C)N=C3)=NN2CCC1 HHZBYCZWQLBOCA-NTUHNPAUSA-N 0.000 claims 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 206010002022 amyloidosis Diseases 0.000 claims 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- FIHZRPHAOVYWEH-UDWIEESQSA-N (8e)-2-[(4-fluorophenyl)methyl]-8-[[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]methylidene]-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C(C1=N2)/CCCN1N=C2CC1=CC=C(F)C=C1 FIHZRPHAOVYWEH-UDWIEESQSA-N 0.000 claims 1
- YHFGELPHHDMZHO-YICVCXCLSA-N (8r)-8-(4-chlorophenyl)-3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C1([C@@H]2C3=NN=C(N3CCC2)/C=C/C=2C=C(C(=CC=2)N2C=C(C)N=C2)OC)=CC=C(Cl)C=C1 YHFGELPHHDMZHO-YICVCXCLSA-N 0.000 claims 1
- YHFGELPHHDMZHO-BOQJPMNSSA-N (8s)-8-(4-chlorophenyl)-3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C1([C@H]2C3=NN=C(N3CCC2)/C=C/C=2C=C(C(=CC=2)N2C=C(C)N=C2)OC)=CC=C(Cl)C=C1 YHFGELPHHDMZHO-BOQJPMNSSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- NTSFRWOCQNZBPE-ONNFQVAWSA-N 1-(4-fluorophenyl)-3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,7-dihydro-5h-imidazo[1,5-a]pyrazin-8-one Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1CCNC(=O)C1=1)=NC=1C1=CC=C(F)C=C1 NTSFRWOCQNZBPE-ONNFQVAWSA-N 0.000 claims 1
- MKOUANAAYOBUQS-ONNFQVAWSA-N 1-(4-fluorophenyl)-3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,8-dihydro-5h-imidazo[5,1-c][1,4]oxazine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1CCOCC1=1)=NC=1C1=CC=C(F)C=C1 MKOUANAAYOBUQS-ONNFQVAWSA-N 0.000 claims 1
- RMMNVBJKJSXECZ-XYOKQWHBSA-N 1-[(4-fluorophenyl)methyl]-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-4,5-dimethylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C1=NC(C)=C(C)N1CC1=CC=C(F)C=C1 RMMNVBJKJSXECZ-XYOKQWHBSA-N 0.000 claims 1
- RCLLKUOOBHJCTE-PKNBQFBNSA-N 1-[2-methoxy-4-[(e)-2-(5-phenyl-1h-imidazol-2-yl)ethenyl]phenyl]-4-methylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(NC=1)=NC=1C1=CC=CC=C1 RCLLKUOOBHJCTE-PKNBQFBNSA-N 0.000 claims 1
- FAEGAULHOWGHCT-PKNBQFBNSA-N 1-[2-methoxy-4-[(e)-2-[5-(2-methoxyphenyl)-1h-imidazol-2-yl]ethenyl]phenyl]-4-methylimidazole Chemical compound COC1=CC=CC=C1C1=CNC(\C=C\C=2C=C(OC)C(=CC=2)N2C=C(C)N=C2)=N1 FAEGAULHOWGHCT-PKNBQFBNSA-N 0.000 claims 1
- DMMLTKBRQGWGBC-CSKARUKUSA-N 1-[2-methoxy-4-[(e)-2-[5-(3-methoxyphenyl)-1h-imidazol-2-yl]ethenyl]phenyl]-4-methylimidazole Chemical compound COC1=CC=CC(C=2N=C(\C=C\C=3C=C(OC)C(=CC=3)N3C=C(C)N=C3)NC=2)=C1 DMMLTKBRQGWGBC-CSKARUKUSA-N 0.000 claims 1
- UMWLWXCNEOMVEM-VZUCSPMQSA-N 1-[2-methoxy-4-[(e)-2-[5-(4-methoxyphenyl)-1h-imidazol-2-yl]ethenyl]phenyl]-4-methylimidazole Chemical compound C1=CC(OC)=CC=C1C1=CNC(\C=C\C=2C=C(OC)C(=CC=2)N2C=C(C)N=C2)=N1 UMWLWXCNEOMVEM-VZUCSPMQSA-N 0.000 claims 1
- QKKCRIRBDWMEJO-GQCTYLIASA-N 1-[4-[(e)-2-(5-chloro-1h-imidazol-2-yl)ethenyl]-2-methoxyphenyl]-4-methylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C1=NC(Cl)=CN1 QKKCRIRBDWMEJO-GQCTYLIASA-N 0.000 claims 1
- JMIMRKFFYGMRAA-ONNFQVAWSA-N 1-[4-[(e)-2-[5-(4-chlorophenyl)-1h-imidazol-2-yl]ethenyl]-2-methoxyphenyl]-4-methylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(NC=1)=NC=1C1=CC=C(Cl)C=C1 JMIMRKFFYGMRAA-ONNFQVAWSA-N 0.000 claims 1
- JTFWKEFCHFOGHE-ONNFQVAWSA-N 1-[4-[(e)-2-[5-(4-fluorophenyl)-1h-imidazol-2-yl]ethenyl]-2-methoxyphenyl]-4-methylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(NC=1)=NC=1C1=CC=C(F)C=C1 JTFWKEFCHFOGHE-ONNFQVAWSA-N 0.000 claims 1
- HEPATOAZXTVVDH-UXBLZVDNSA-N 1-[4-[(e)-2-[5-[(4-fluorophenyl)methyl]-1h-imidazol-2-yl]ethenyl]-2-methoxyphenyl]-4-methylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(NC=1)=NC=1CC1=CC=C(F)C=C1 HEPATOAZXTVVDH-UXBLZVDNSA-N 0.000 claims 1
- GTBMIVYKTVKBQE-UHFFFAOYSA-N 1h-triazolo[1,5-a]azepine Chemical compound C1=CC=CN2NN=CC2=C1 GTBMIVYKTVKBQE-UHFFFAOYSA-N 0.000 claims 1
- GQCSLAPDYCEANX-AATRIKPKSA-N 2-[(e)-2-[2-fluoro-5-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC(F)=C(F)C(F)=C1 GQCSLAPDYCEANX-AATRIKPKSA-N 0.000 claims 1
- FRSBIDGXMBDIFI-JXMROGBWSA-N 2-[(e)-2-[2-fluoro-5-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC=C(F)C=C1 FRSBIDGXMBDIFI-JXMROGBWSA-N 0.000 claims 1
- DSOHYMJIFPTMDI-RUDMXATFSA-N 2-[(e)-2-[2-fluoro-5-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(4-fluorophenyl)-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound FC=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(O)C1=CC=C(F)C=C1 DSOHYMJIFPTMDI-RUDMXATFSA-N 0.000 claims 1
- WGVNUPKENODMAA-ZRDIBKRKSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1-methyl-4-phenylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N(C=1)C)=NC=1C1=CC=CC=C1 WGVNUPKENODMAA-ZRDIBKRKSA-N 0.000 claims 1
- HBYWSYHJIUYQDC-ZRDIBKRKSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1-methyl-5-phenylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1C)=NC=C1C1=CC=CC=C1 HBYWSYHJIUYQDC-ZRDIBKRKSA-N 0.000 claims 1
- ORKJTDDBXWRNFY-GQCTYLIASA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-7-(3,4,5-trifluorophenyl)-6,7-dihydro-5h-pyrrolo[1,2-b][1,2,4]triazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CC2)N=C1C2C1=CC(F)=C(F)C(F)=C1 ORKJTDDBXWRNFY-GQCTYLIASA-N 0.000 claims 1
- OZAUYOSBLXLUTO-ACCUITESSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(2-methoxyphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC=CC=C1C1C2=NC(\C=C\C=3C=C(OC)C(=CC=3)N3C=C(C)N=C3)=NN2CCC1 OZAUYOSBLXLUTO-ACCUITESSA-N 0.000 claims 1
- MLDLRNATTWHWBE-FNORWQNLSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(3,4,5-trifluorophenyl)-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(O)C1=CC(F)=C(F)C(F)=C1 MLDLRNATTWHWBE-FNORWQNLSA-N 0.000 claims 1
- GNQGMJWSSMNPIR-YRNVUSSQSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-(4-methylphenyl)-6,8-dihydro-5h-[1,2,4]triazolo[5,1-c][1,4]oxazine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCO2)N=C1C2C1=CC=C(C)C=C1 GNQGMJWSSMNPIR-YRNVUSSQSA-N 0.000 claims 1
- TXYJGXVJRDEGPF-FYWRMAATSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-naphthalen-1-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC(\C=C\C2=NN3CCCC(C3=N2)C=2C3=CC=CC=C3C=CC=2)=CC=C1N1C=NC(C)=C1 TXYJGXVJRDEGPF-FYWRMAATSA-N 0.000 claims 1
- WGEOZEVVAFYXTQ-ZRDIBKRKSA-N 2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-8-phenyl-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridine-8-carbonitrile Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(C#N)C1=CC=CC=C1 WGEOZEVVAFYXTQ-ZRDIBKRKSA-N 0.000 claims 1
- DHLFNYGRJWGLJB-AATRIKPKSA-N 2-[(e)-2-[5-methoxy-6-(4-methylimidazol-1-yl)pyridin-3-yl]ethenyl]-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1N=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC(F)=C(F)C(F)=C1 DHLFNYGRJWGLJB-AATRIKPKSA-N 0.000 claims 1
- HCSNRLMIMJJKHQ-SNAWJCMRSA-N 2-[(e)-2-[5-methoxy-6-(4-methylimidazol-1-yl)pyridin-3-yl]ethenyl]-8-(3,4,5-trifluorophenyl)-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound C=1N=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(O)C1=CC(F)=C(F)C(F)=C1 HCSNRLMIMJJKHQ-SNAWJCMRSA-N 0.000 claims 1
- YLYQTLPNUAEHJU-VZUCSPMQSA-N 2-[4-(4-fluorophenyl)-5-(methoxymethyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]imidazol-1-yl]ethanol Chemical compound OCCN1C(COC)=C(C=2C=CC(F)=CC=2)N=C1\C=C\C(C=C1OC)=CC=C1N1C=NC(C)=C1 YLYQTLPNUAEHJU-VZUCSPMQSA-N 0.000 claims 1
- NEQSYUAQGMCWJD-ACCUITESSA-N 3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1-methyl-5-(1-phenylethyl)-1,2,4-triazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1C)N=C1C(C)C1=CC=CC=C1 NEQSYUAQGMCWJD-ACCUITESSA-N 0.000 claims 1
- OSOKWONGWUVJJK-WYMLVPIESA-N 3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1CCCCC1=1)=NC=1C1=CC=CC=C1 OSOKWONGWUVJJK-WYMLVPIESA-N 0.000 claims 1
- AJICJFMNJWNYHY-ZRDIBKRKSA-N 3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5-(1-phenylethyl)-1h-1,2,4-triazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1)=NN=C1C(C)C1=CC=CC=C1 AJICJFMNJWNYHY-ZRDIBKRKSA-N 0.000 claims 1
- AJICJFMNJWNYHY-DPCFLFMUSA-N 3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5-[(1r)-1-phenylethyl]-1h-1,2,4-triazole Chemical compound C1([C@@H](C)C2=NN=C(N2)/C=C/C=2C=C(C(=CC=2)N2C=C(C)N=C2)OC)=CC=CC=C1 AJICJFMNJWNYHY-DPCFLFMUSA-N 0.000 claims 1
- AJICJFMNJWNYHY-JICACKBISA-N 3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5-[(1s)-1-phenylethyl]-1h-1,2,4-triazole Chemical compound C1([C@H](C)C2=NN=C(N2)/C=C/C=2C=C(C(=CC=2)N2C=C(C)N=C2)OC)=CC=CC=C1 AJICJFMNJWNYHY-JICACKBISA-N 0.000 claims 1
- UYSGVEBSVPGEBR-GQCTYLIASA-N 3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-7-(3,4,5-trifluorophenyl)-6,7-dihydro-5h-pyrrolo[2,1-c][1,2,4]triazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1CC2)=NN=C1C2C1=CC(F)=C(F)C(F)=C1 UYSGVEBSVPGEBR-GQCTYLIASA-N 0.000 claims 1
- PWVHPGTXAKBAQE-VZUCSPMQSA-N 4-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1-methylimidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N(C=1)C)=NC=1C1=CC=C(F)C=C1 PWVHPGTXAKBAQE-VZUCSPMQSA-N 0.000 claims 1
- ZSTZSTATBPOYBI-ONNFQVAWSA-N 4-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1h-imidazole-5-carboxylic acid Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1)=NC(C(O)=O)=C1C1=CC=C(F)C=C1 ZSTZSTATBPOYBI-ONNFQVAWSA-N 0.000 claims 1
- BPVUOEALSVTFFU-VZUCSPMQSA-N 4-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5-methyl-1h-imidazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1)=NC(C)=C1C1=CC=C(F)C=C1 BPVUOEALSVTFFU-VZUCSPMQSA-N 0.000 claims 1
- OCSVRGARPGLGPU-RIYZIHGNSA-N 4-[2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-yl]-n,n-dimethylaniline Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC=C(N(C)C)C=C1 OCSVRGARPGLGPU-RIYZIHGNSA-N 0.000 claims 1
- TVIKCEPHNNHTTN-XYOKQWHBSA-N 4-[2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-yl]benzonitrile Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC=C(C#N)C=C1 TVIKCEPHNNHTTN-XYOKQWHBSA-N 0.000 claims 1
- DYFPUKWFZBWNMO-UXBLZVDNSA-N 4-[2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,8-dihydro-5h-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-yl]benzonitrile Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCO2)N=C1C2C1=CC=C(C#N)C=C1 DYFPUKWFZBWNMO-UXBLZVDNSA-N 0.000 claims 1
- BWDBBDXCHPPZNB-SOFGYWHQSA-N 4-[3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1h-1,2,4-triazol-5-yl]-4-(3,4,5-trifluorophenyl)butan-1-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1)=NN=C1C(CCCO)C1=CC(F)=C(F)C(F)=C1 BWDBBDXCHPPZNB-SOFGYWHQSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- WTBXBULIQGJHNQ-ACCUITESSA-N 5-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1-methyl-3-(1-phenylethyl)-1,2,4-triazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N(N=1)C)=NC=1C(C)C1=CC=CC=C1 WTBXBULIQGJHNQ-ACCUITESSA-N 0.000 claims 1
- SSNFDOZTFDCJFS-WUXMJOGZSA-N 5-[methoxy-(4-methoxyphenyl)methyl]-3-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1h-1,2,4-triazole Chemical compound C=1C=C(OC)C=CC=1C(OC)C(NN=1)=NC=1\C=C\C(C=C1OC)=CC=C1N1C=NC(C)=C1 SSNFDOZTFDCJFS-WUXMJOGZSA-N 0.000 claims 1
- YJCYLFYNGBSXQJ-VZUCSPMQSA-N 7-(4-fluorophenyl)-7-methoxy-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6-dihydropyrrolo[1,2-b][1,2,4]triazole Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCC2(OC)C1=CC=C(F)C=C1 YJCYLFYNGBSXQJ-VZUCSPMQSA-N 0.000 claims 1
- LVLVBMKGPNNHNM-UXBLZVDNSA-N 8-(3,4-difluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC2)N=C1C2C1=CC=C(F)C(F)=C1 LVLVBMKGPNNHNM-UXBLZVDNSA-N 0.000 claims 1
- KACXLOORNWFOCL-WUXMJOGZSA-N 8-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCC=2)N=C1C=2C1=CC=C(F)C=C1 KACXLOORNWFOCL-WUXMJOGZSA-N 0.000 claims 1
- AGCGZSWEZREMJY-VZUCSPMQSA-N 8-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridin-8-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(O)C1=CC=C(F)C=C1 AGCGZSWEZREMJY-VZUCSPMQSA-N 0.000 claims 1
- HBVBZAZTCCELNB-WUXMJOGZSA-N 8-(4-fluorophenyl)-8-methoxy-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,7-dihydro-5h-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=N1)N=C2N1CCCC2(OC)C1=CC=C(F)C=C1 HBVBZAZTCCELNB-WUXMJOGZSA-N 0.000 claims 1
- SRZMIJBELJDWFT-XBXARRHUSA-N 8-(6-chloropyridin-3-yl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-6,8-dihydro-5h-[1,2,4]triazolo[5,1-c][1,4]oxazine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(=NN1CCO2)N=C1C2C1=CC=C(Cl)N=C1 SRZMIJBELJDWFT-XBXARRHUSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- ZXCOIUJZPVNJFO-VZUCSPMQSA-N methyl 4-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1h-imidazole-5-carboxylate Chemical compound N1C(C=2C=CC(F)=CC=2)=C(C(=O)OC)N=C1\C=C\C(C=C1OC)=CC=C1N1C=NC(C)=C1 ZXCOIUJZPVNJFO-VZUCSPMQSA-N 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 1
- DEONRSKBUDATDN-ONNFQVAWSA-N n-(2-chloroethyl)-4-(4-fluorophenyl)-2-[(e)-2-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]ethenyl]-1h-imidazole-5-carboxamide Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C\C(N1)=NC(C(=O)NCCCl)=C1C1=CC=C(F)C=C1 DEONRSKBUDATDN-ONNFQVAWSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 claims 1
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims 1
- 125000000837 carbohydrate group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78051706P | 2006-03-09 | 2006-03-09 | |
| JP2006063562 | 2006-03-09 | ||
| US86170206P | 2006-11-30 | 2006-11-30 | |
| JP2006322728 | 2006-11-30 | ||
| PCT/JP2007/054532 WO2007102580A1 (ja) | 2006-03-09 | 2007-03-08 | 多環式シンナミド誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120174T1 true HRP20120174T1 (hr) | 2012-03-31 |
Family
ID=38474999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20120174T HRP20120174T1 (hr) | 2006-03-09 | 2012-02-22 | Derivat policikličnog cinamida |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1992618B1 (ru) |
| KR (1) | KR101464651B1 (ru) |
| AR (1) | AR059955A1 (ru) |
| AU (1) | AU2007223158B2 (ru) |
| CA (1) | CA2643796A1 (ru) |
| CY (1) | CY1112767T1 (ru) |
| EA (1) | EA016464B1 (ru) |
| GE (1) | GEP20115139B (ru) |
| HK (2) | HK1122027A1 (ru) |
| HN (1) | HN2008001374A (ru) |
| HR (1) | HRP20120174T1 (ru) |
| IL (1) | IL193770A (ru) |
| MA (1) | MA30268B1 (ru) |
| MX (1) | MX2008011221A (ru) |
| PL (1) | PL1992618T3 (ru) |
| WO (1) | WO2007102580A1 (ru) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1757591A4 (en) | 2004-05-26 | 2010-05-05 | Eisai R&D Man Co Ltd | ZIMTSÄUREAMIDVERBINDUNG |
| JPWO2006046575A1 (ja) | 2004-10-26 | 2008-05-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | シンナミド化合物の非晶質体 |
| TWI370130B (en) | 2005-11-24 | 2012-08-11 | Eisai R&D Man Co Ltd | Two cyclic cinnamide compound |
| NZ568050A (en) | 2005-11-24 | 2010-09-30 | Eisai R&D Man Co Ltd | Morpholine type cinnamide compound |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| SA07280403B1 (ar) | 2006-07-28 | 2010-12-01 | إيساي أر أند دي منجمنت كو. ليمتد | ملح رباعي لمركب سيناميد |
| AU2008214372A1 (en) * | 2007-02-08 | 2008-08-14 | Merck Sharp & Dohme Corp. | Therapeutic agents |
| TW200848054A (en) | 2007-02-28 | 2008-12-16 | Eisai R&D Man Co Ltd | Two cyclic oxomorpholine derivatives |
| BRPI0811993A2 (pt) | 2007-05-11 | 2014-11-18 | Hoffmann La Roche | " hetarilanilinas como moduladores para beta-amiloide ". |
| EP2152695A2 (en) * | 2007-06-01 | 2010-02-17 | Schering Corporation | Gamma secretase modulators |
| US7935815B2 (en) * | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| AU2008292390B2 (en) | 2007-08-31 | 2013-04-04 | Eisai R & D Management Co., Ltd. | Polycyclic compound |
| US8487099B2 (en) | 2007-11-05 | 2013-07-16 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
| JP2011506460A (ja) * | 2007-12-11 | 2011-03-03 | シェーリング コーポレイション | γ−セクレターゼモジュレーター |
| US8217064B2 (en) | 2007-12-20 | 2012-07-10 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| AU2008340421B2 (en) | 2007-12-21 | 2013-12-19 | F. Hoffmann-La Roche Ag | Heteroaryl derivatives as orexin receptor antagonists |
| US7923450B2 (en) | 2008-01-11 | 2011-04-12 | Hoffmann-La Roche Inc. | Modulators for amyloid beta |
| CN101952275B (zh) | 2008-02-22 | 2014-06-18 | 弗·哈夫曼-拉罗切有限公司 | β-淀粉样蛋白的调节剂 |
| WO2010025197A1 (en) * | 2008-08-27 | 2010-03-04 | Eisai R&D Management Co., Ltd. | Process for preparing certain cinnamide compounds |
| CA2736924C (en) | 2008-10-09 | 2016-06-28 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| AU2009313524A1 (en) * | 2008-11-06 | 2010-05-14 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
| EP2356115A1 (en) * | 2008-11-06 | 2011-08-17 | Schering Corporation | Gamma secretase modulators |
| KR101293421B1 (ko) | 2008-11-10 | 2013-08-05 | 에프. 호프만-라 로슈 아게 | 헤테로사이클릭 감마 분비효소 조절제 |
| EP2365973A1 (en) | 2008-11-13 | 2011-09-21 | Schering Corporation | Gamma secretase modulators |
| CA2747744A1 (en) | 2008-12-22 | 2010-07-01 | Theodros Asberom | Gamma secretase modulators |
| TW201030002A (en) | 2009-01-16 | 2010-08-16 | Bristol Myers Squibb Co | Bicyclic compounds for the reduction of beta-amyloid production |
| JP2012121809A (ja) * | 2009-02-26 | 2012-06-28 | Eisai R & D Management Co Ltd | 多環式化合物の製造法およびその中間体 |
| NZ594776A (en) | 2009-02-26 | 2013-05-31 | Eisai R&D Man Co Ltd | Nitrogen-containing fused heterocyclic compounds and their use as beta amyloid production inhibitors |
| JP2012051805A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | テトラヒドロトリアゾロピリジン誘導体の製造方法 |
| CA2749702A1 (en) | 2009-02-26 | 2010-09-02 | Eisai R&D Management Co., Ltd. | Salt of tetrahydrotriazolopyridine derivative and crystal thereof |
| JP2012051807A (ja) * | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | アリールイミダゾール化合物 |
| JPWO2011007756A1 (ja) * | 2009-07-13 | 2012-12-27 | 武田薬品工業株式会社 | 複素環化合物及びその用途 |
| US8871760B2 (en) * | 2009-09-21 | 2014-10-28 | Roche Palo Alto Llc | [1,2,4]triazolo[3,4-C][1,4]oxazines as P2X7 modulators |
| BR112012017442A2 (pt) * | 2010-01-15 | 2016-04-19 | Janssen Pharmaceuticals Inc | derivados de triazol bicíclicos substituídos como moduladores de gamma secretase |
| US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| CA2791914C (en) | 2010-03-05 | 2019-01-15 | Karyopharm Therapeutics, Inc. | Nuclear transport modulators and uses thereof |
| MX2013002511A (es) * | 2010-09-02 | 2013-07-29 | Takeda Pharmaceutical | Triazoles fusionados para el tratamiento o profilaxis de daño cognitivo moderado. |
| JP2014012641A (ja) * | 2010-10-29 | 2014-01-23 | Dainippon Sumitomo Pharma Co Ltd | 新規ピリジン誘導体 |
| WO2012099807A1 (en) * | 2011-01-17 | 2012-07-26 | Karyopharm Therapeutics, Inc. | Olefin containing nuclear transport modulators and uses thereof |
| EA201490406A1 (ru) | 2011-07-29 | 2014-07-30 | Кариофарм Терапевтикс, Инк. | Модуляторы ядерного транспорта и их применение |
| PL2736887T3 (pl) | 2011-07-29 | 2018-03-30 | Karyopharm Therapeutics, Inc. | Modulatory transportu jądrowego zawierające ugrupowanie hydrazydu i ich zastosowania |
| US9708276B2 (en) | 2011-10-12 | 2017-07-18 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecules targeting androgen receptor nuclear localization and/or level in prostate cancer |
| LT3404027T (lt) | 2012-05-09 | 2020-07-10 | Biogen Ma Inc. | Branduolių transporto moduliatoriai ir jų panaudojimas |
| BR112014028395B1 (pt) | 2012-05-16 | 2022-02-01 | Janssen Pharmaceuticals, Inc. | Derivados 3,4-di-hidro-2h-pirido[1,2-a]pirazina-1,6-diona substituídos úteis para o tratamento de (inter alia) doença de alzheimer e composição farmacêutica que os compreende |
| EP2687528A1 (en) * | 2012-07-17 | 2014-01-22 | Ares Trading S.A. | Fused triazole derivatives as gamma secretase modulators |
| AU2013366668B2 (en) | 2012-12-20 | 2017-07-20 | Janssen Pharmaceutica Nv | Novel tricyclic 3,4-dihydro-2H-pyrido[1,2-alpha]pyrazine -1,6-dione derivatives as gamma secretase modulators |
| KR102171710B1 (ko) | 2013-01-17 | 2020-10-30 | 얀센 파마슈티카 엔.브이. | 감마 세크레타제 조절 인자로서의 신규 치환 피리도-피페라지논 유도체 |
| US10202366B2 (en) | 2013-03-15 | 2019-02-12 | Karyopharm Therapeutics Inc. | Methods of promoting wound healing using CRM1 inhibitors |
| SG11201510036TA (en) | 2013-06-21 | 2016-01-28 | Karyopharm Therapeutics Inc | Nuclear transport modulators and uses thereof |
| US20160257657A1 (en) | 2013-09-20 | 2016-09-08 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Small molecule inhibitors of the nuclear translocation of androgen receptor for the treatment of castration-resistant prostate cancer |
| CA2924527C (en) | 2013-09-20 | 2022-07-12 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Compounds for treating prostate cancer |
| 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 |
| WO2016025904A1 (en) | 2014-08-15 | 2016-02-18 | Karyopharm Therapeutics Inc. | Polymorphs of selinexor |
| US10709706B2 (en) | 2015-12-31 | 2020-07-14 | Karopharm Therapeutics Inc. | Nuclear transport modulators and uses thereof |
| WO2017117529A1 (en) | 2015-12-31 | 2017-07-06 | Karyopharm Therapeutics Inc. | Nuclear transport modulators and uses thereof |
| US10980806B2 (en) | 2016-03-24 | 2021-04-20 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecule inhibitors of the nuclear translocation of androgen receptor for the treatment of castration-resistant prostate cancer |
| US11602530B2 (en) | 2016-11-28 | 2023-03-14 | Biogen Ma Inc. | CRM1 inhibitors for treating epilepsy |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2956702A (en) * | 2000-12-04 | 2002-06-18 | Hoffmann La Roche | Phenylethenyl or phenylethinyl derivatives as glutamate receptor antagonists |
| EP1594847A2 (en) * | 2003-02-12 | 2005-11-16 | Transtech Pharma, Inc. | Substituted azole derivatives as therapeutic agents |
| EP1730118A1 (en) * | 2004-02-12 | 2006-12-13 | Transtech Pharma, Inc. | Substituted azole derivatives, compositions, and methods of use |
| EP1757591A4 (en) * | 2004-05-26 | 2010-05-05 | Eisai R&D Man Co Ltd | ZIMTSÄUREAMIDVERBINDUNG |
-
2007
- 2007-03-08 CA CA002643796A patent/CA2643796A1/en not_active Abandoned
- 2007-03-08 KR KR1020087023309A patent/KR101464651B1/ko not_active IP Right Cessation
- 2007-03-08 EP EP07738023A patent/EP1992618B1/en active Active
- 2007-03-08 GE GEAP200710893A patent/GEP20115139B/en unknown
- 2007-03-08 AR ARP070100958A patent/AR059955A1/es not_active Application Discontinuation
- 2007-03-08 EA EA200870336A patent/EA016464B1/ru not_active IP Right Cessation
- 2007-03-08 WO PCT/JP2007/054532 patent/WO2007102580A1/ja active Application Filing
- 2007-03-08 AU AU2007223158A patent/AU2007223158B2/en not_active Ceased
- 2007-03-08 MX MX2008011221A patent/MX2008011221A/es active IP Right Grant
- 2007-03-08 PL PL07738023T patent/PL1992618T3/pl unknown
-
2008
- 2008-08-28 IL IL193770A patent/IL193770A/en not_active IP Right Cessation
- 2008-09-05 HN HN2008001374A patent/HN2008001374A/es unknown
- 2008-09-08 MA MA31220A patent/MA30268B1/fr unknown
-
2009
- 2009-03-11 HK HK09102339.7A patent/HK1122027A1/xx not_active IP Right Cessation
- 2009-06-19 HK HK09105547.8A patent/HK1128085A1/xx not_active IP Right Cessation
-
2012
- 2012-02-16 CY CY20121100165T patent/CY1112767T1/el unknown
- 2012-02-22 HR HR20120174T patent/HRP20120174T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1122027A1 (en) | 2009-05-08 |
| HN2008001374A (es) | 2011-03-15 |
| IL193770A0 (en) | 2009-05-04 |
| KR101464651B1 (ko) | 2014-11-24 |
| MA30268B1 (fr) | 2009-03-02 |
| EP1992618A4 (en) | 2010-11-10 |
| AR059955A1 (es) | 2008-05-14 |
| EP1992618A1 (en) | 2008-11-19 |
| KR20080108481A (ko) | 2008-12-15 |
| MX2008011221A (es) | 2008-09-11 |
| PL1992618T3 (pl) | 2012-06-29 |
| EA016464B1 (ru) | 2012-05-30 |
| EA200870336A1 (ru) | 2009-02-27 |
| AU2007223158B2 (en) | 2012-04-12 |
| GEP20115139B (en) | 2011-01-10 |
| HK1128085A1 (en) | 2009-10-16 |
| EP1992618B1 (en) | 2012-01-18 |
| AU2007223158A1 (en) | 2007-09-13 |
| CA2643796A1 (en) | 2007-09-13 |
| IL193770A (en) | 2012-10-31 |
| WO2007102580A1 (ja) | 2007-09-13 |
| CY1112767T1 (el) | 2016-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20120174T1 (hr) | Derivat policikličnog cinamida | |
| AU2019203444B2 (en) | Bicyclic lactams and methods of use thereof | |
| JP7418395B2 (ja) | Ｓｈｐ２ホスファターゼ阻害剤およびこれらの使用方法 | |
| JP6382867B2 (ja) | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 | |
| AU2011240808B2 (en) | 5, 7-substituted-imidazo [1, 2-c] pyrimidines as inhibitors of JAK kinases | |
| JP6785384B2 (ja) | 新規なヘテロ環化合物、その製造方法およびこれを含む薬学的組成物 | |
| JP2019504821A (ja) | ユビキチン特異的プロテアーゼ１阻害剤としてのプリノン | |
| JP2018522046A5 (ru) | ||
| ES2271221T3 (es) | Derivados imidazo-pirimidina como ligandos para receptores gaba. | |
| JP2011516512A5 (ja) | 新規な置換スピロ[シクロアルキル−１,３'−インドール]−２'(１'Ｈ)−オン誘導体およびｐ３８マイトジェン活性化タンパク質キナーゼ阻害剤としてのそれらの使用 | |
| CA2694401A1 (en) | Polycyclic compound | |
| HUE032770T2 (en) | New NK-3 receptor selective antagonist compounds, pharmaceutical compositions and methods for use in NK-3 receptor mediated disorders | |
| BG107899A (bg) | Б...нзимидазолови и пиридилимидазолови производни ка'о лиганди на gaba р...-...п'ори | |
| EP3356345A1 (en) | Heteroaryl derivatives as sepiapterin reductase inhibitors | |
| HRP20160649T1 (hr) | Novi derivati tienopirimidina, postupci za njihovo pripremanje i njihova terapeutska uporaba | |
| CA2521929A1 (en) | Condensed n-heterocyclic compounds and their use as crf receptor antagonists | |
| RU2005117383A (ru) | Производные фенилаланина в качестве ингибиторов дипептидилпептидазы для лечения или профилактики диабета | |
| JP2016520116A (ja) | イミダゾピロリジノン誘導体および疾患の処置におけるその使用 | |
| WO2008072779A1 (ja) | キノキサリン誘導体 | |
| EP1478357A2 (en) | Tricyclic pyrazole derivatives, process for their preparation and their use as antitumor agents | |
| JP2001525802A (ja) | ＧＡＢＡα５リガンドとしての置換１，２，４−トリアゾロ［３，４−ａ］フタラジン誘導体 | |
| JP2004538316A5 (ru) | ||
| ES2550201T3 (es) | Moduladores de la PDE10 | |
| TW202136270A (zh) | 環狀化合物及其使用方法 | |
| JP2024512740A (ja) | 例えばがんの処置のためのＳＨＰ２阻害剤としての（Ｓ）－１－（５－（（ピリジン－３－イル）チオ）ピラジン－２－イル）－４’Ｈ，６’Ｈ－スピロ［ピペリジン－４，５’－ピロロ［１，２－ｂ］ピラゾール］－４’－アミン誘導体及び同様の化合物 |