JP2009541311A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009541311A5 JP2009541311A5 JP2009516446A JP2009516446A JP2009541311A5 JP 2009541311 A5 JP2009541311 A5 JP 2009541311A5 JP 2009516446 A JP2009516446 A JP 2009516446A JP 2009516446 A JP2009516446 A JP 2009516446A JP 2009541311 A5 JP2009541311 A5 JP 2009541311A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- isoindol
- phenyl
- amine
- pyridin
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims 111
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 30
- 125000002877 alkyl aryl group Chemical group 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 12
- -1 alkenyl R 6 Chemical compound 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 7
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 6
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 208000024827 Alzheimer disease Diseases 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 230000003902 lesion Effects 0.000 claims 4
- LAQKOENYJDDTDY-UHFFFAOYSA-N 4-[3-amino-1-(4-hydroxyphenyl)isoindol-1-yl]phenol Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 LAQKOENYJDDTDY-UHFFFAOYSA-N 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- RXPHIWHATFBINA-UHFFFAOYSA-N 2-[3-amino-1-(4-hydroxyphenyl)isoindol-1-yl]phenol Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CC=CC=1)O)C1=CC=C(O)C=C1 RXPHIWHATFBINA-UHFFFAOYSA-N 0.000 claims 2
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- KTVJPEWAPJPEOK-UHFFFAOYSA-N [3-[3-amino-1-(4-fluoro-3-pyrimidin-5-ylphenyl)isoindol-1-yl]phenyl] trifluoromethanesulfonate Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C(F)=CC=1)C=1C=NC=NC=1)C1=CC=CC(OS(=O)(=O)C(F)(F)F)=C1 KTVJPEWAPJPEOK-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 1
- RSWYTHKZAKEODI-UHFFFAOYSA-N 3,3-dimethylisoindol-1-amine Chemical compound C1=CC=C2C(C)(C)N=C(N)C2=C1 RSWYTHKZAKEODI-UHFFFAOYSA-N 0.000 claims 1
- FYQHSDGQCJETLW-UHFFFAOYSA-N 3,3-diphenylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=CC=CC=1)C1=CC=CC=C1 FYQHSDGQCJETLW-UHFFFAOYSA-N 0.000 claims 1
- YFRVXHOJYFHAOP-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-(3-bromophenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C2OCOC2=CC=1)C1=CC=CC(Br)=C1 YFRVXHOJYFHAOP-UHFFFAOYSA-N 0.000 claims 1
- YSHQEJDYWRDFNV-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C2OCOC2=CC=1)C(C=1)=CC=CC=1C1=CN=CN=C1 YSHQEJDYWRDFNV-UHFFFAOYSA-N 0.000 claims 1
- PQRUSXIAEQXMOU-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C2OCOC2=CC=1)C(C=1)=CC=CC=1C1=CC=CN=C1F PQRUSXIAEQXMOU-UHFFFAOYSA-N 0.000 claims 1
- HRNPAIOJTACERQ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-[3-(3-methoxyphenyl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C3OCOC3=CC=2)=C1 HRNPAIOJTACERQ-UHFFFAOYSA-N 0.000 claims 1
- VZDJIRZZYSFVRR-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-[3-(5-methoxypyridin-3-yl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CN=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C3OCOC3=CC=2)=C1 VZDJIRZZYSFVRR-UHFFFAOYSA-N 0.000 claims 1
- KROAJEYJMROWNY-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-pyridin-3-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C2OCCOC2=CC=1)C(C=1)=CC=CC=1C1=CC=CN=C1 KROAJEYJMROWNY-UHFFFAOYSA-N 0.000 claims 1
- KEKAVQSDOJVSNU-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C2OCCOC2=CC=1)C(C=1)=CC=CC=1C1=CN=CN=C1 KEKAVQSDOJVSNU-UHFFFAOYSA-N 0.000 claims 1
- XLVJMWWGXURWKV-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C2OCCOC2=CC=1)C(C=1)=CC=CC=1C1=CC=CN=C1F XLVJMWWGXURWKV-UHFFFAOYSA-N 0.000 claims 1
- HGLAOFZAFIFUKA-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[3-(3-methoxyphenyl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C3OCCOC3=CC=2)=C1 HGLAOFZAFIFUKA-UHFFFAOYSA-N 0.000 claims 1
- MXVJZGAFZLJLQZ-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[3-(5-methoxypyridin-3-yl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CN=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C3OCCOC3=CC=2)=C1 MXVJZGAFZLJLQZ-UHFFFAOYSA-N 0.000 claims 1
- USZVXCYBGOQIKE-UHFFFAOYSA-N 3-(2-chloropyridin-4-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(Cl)N=CC=1)C(C=1)=CC=CC=1C1=CN=CN=C1 USZVXCYBGOQIKE-UHFFFAOYSA-N 0.000 claims 1
- VOFJGSZKPNRYLS-UHFFFAOYSA-N 3-(2-chloropyridin-4-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=NC(Cl)=C1 VOFJGSZKPNRYLS-UHFFFAOYSA-N 0.000 claims 1
- SRJWFQRFHSLIHN-UHFFFAOYSA-N 3-(2-ethylpyridin-4-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C1=NC(CC)=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C=CC=2)C=2C=NC=NC=2)=C1 SRJWFQRFHSLIHN-UHFFFAOYSA-N 0.000 claims 1
- QXZLSUXNFCVKSB-UHFFFAOYSA-N 3-(2-ethylpyridin-4-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C1=NC(CC)=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)=C1 QXZLSUXNFCVKSB-UHFFFAOYSA-N 0.000 claims 1
- FJKNWPNCHKXVKK-UHFFFAOYSA-N 3-(2-fluoropyridin-4-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=NC(F)=C1 FJKNWPNCHKXVKK-UHFFFAOYSA-N 0.000 claims 1
- AQWJKONBZLFXLD-UHFFFAOYSA-N 3-(2-methoxypyrimidin-5-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C1=NC(OC)=NC=C1C1(C=2C=C(C=CC=2)C=2C=NC=NC=2)C2=CC=CC=C2C(N)=N1 AQWJKONBZLFXLD-UHFFFAOYSA-N 0.000 claims 1
- BSJUWHOXOHIPGJ-UHFFFAOYSA-N 3-(2-propan-2-ylpyridin-4-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C1=NC(C(C)C)=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C=CC=2)C=2C=NC=NC=2)=C1 BSJUWHOXOHIPGJ-UHFFFAOYSA-N 0.000 claims 1
- LJUZMVAHVKHGST-UHFFFAOYSA-N 3-(3-bromophenyl)-3-(4-methoxyphenyl)isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(Br)C=CC=2)C2=CC=CC=C2C(N)=N1 LJUZMVAHVKHGST-UHFFFAOYSA-N 0.000 claims 1
- JSLVKTXNNUWZNM-UHFFFAOYSA-N 3-(3-fluoropyridin-4-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=CC=1C1=CN=CN=C1 JSLVKTXNNUWZNM-UHFFFAOYSA-N 0.000 claims 1
- PZYOMIWKDHGKSK-UHFFFAOYSA-N 3-(3-fluoropyridin-4-yl)-3-(4-fluoro-3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=C(F)C=1C1=CN=CN=C1 PZYOMIWKDHGKSK-UHFFFAOYSA-N 0.000 claims 1
- HOUJQAJPWSQDKH-UHFFFAOYSA-N 3-(3-fluoropyridin-4-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=CC=1C1=CC=CN=C1F HOUJQAJPWSQDKH-UHFFFAOYSA-N 0.000 claims 1
- SJYZHZUENNZOKO-UHFFFAOYSA-N 3-(3-fluoropyridin-4-yl)-3-[3-(5-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=CC=1C1=CN=CC(F)=C1 SJYZHZUENNZOKO-UHFFFAOYSA-N 0.000 claims 1
- LJHBNAAXZYVNAM-UHFFFAOYSA-N 3-(3-pyrimidin-5-ylphenyl)-3-[4-(trifluoromethoxy)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=C(OC(F)(F)F)C=C1 LJHBNAAXZYVNAM-UHFFFAOYSA-N 0.000 claims 1
- RRIIPJUEPHJBNE-UHFFFAOYSA-N 3-(3-pyrimidin-5-ylphenyl)-3-[4-(trifluoromethyl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=C(C(F)(F)F)C=C1 RRIIPJUEPHJBNE-UHFFFAOYSA-N 0.000 claims 1
- ZYLDGJNRPVVNPD-UHFFFAOYSA-N 3-(3-pyrimidin-5-ylphenyl)-3-[6-(trifluoromethyl)pyridin-3-yl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=C(C(F)(F)F)N=C1 ZYLDGJNRPVVNPD-UHFFFAOYSA-N 0.000 claims 1
- MSERYTUPLPTPDE-UHFFFAOYSA-N 3-(4-fluoro-3-pyrimidin-5-ylphenyl)-3-(4-methoxy-3-methylphenyl)isoindol-1-amine Chemical compound C1=C(C)C(OC)=CC=C1C1(C=2C=C(C(F)=CC=2)C=2C=NC=NC=2)C2=CC=CC=C2C(N)=N1 MSERYTUPLPTPDE-UHFFFAOYSA-N 0.000 claims 1
- GGFAIDPBYPUUNF-UHFFFAOYSA-N 3-(4-fluoro-3-pyrimidin-5-ylphenyl)-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C(F)=CC=1)C=1C=NC=NC=1)C1=CC=NC=C1 GGFAIDPBYPUUNF-UHFFFAOYSA-N 0.000 claims 1
- TXRDWFIBWSXSBA-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)-3-(3-pyridin-3-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=CC=2)C2=CC=CC=C2C(N)=N1 TXRDWFIBWSXSBA-UHFFFAOYSA-N 0.000 claims 1
- SNPJMUOGKNZXET-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=NC=2)C2=CC=CC=C2C(N)=N1 SNPJMUOGKNZXET-UHFFFAOYSA-N 0.000 claims 1
- MBCXQRNZTXKTKR-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)-3-[3-(3-methoxyphenyl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C)C(OC)=CC=2)=C1 MBCXQRNZTXKTKR-UHFFFAOYSA-N 0.000 claims 1
- LROAOFBLCCRMGM-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)-3-[3-(5-methoxypyridin-3-yl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CN=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C)C(OC)=CC=2)=C1 LROAOFBLCCRMGM-UHFFFAOYSA-N 0.000 claims 1
- MKYWJTMYZCYVJX-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-(3-pyridin-3-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=CC=2)C2=CC=CC=C2C(N)=N1 MKYWJTMYZCYVJX-UHFFFAOYSA-N 0.000 claims 1
- IOHWCZWSDVRWJX-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=NC=2)C2=CC=CC=C2C(N)=N1 IOHWCZWSDVRWJX-UHFFFAOYSA-N 0.000 claims 1
- GDOBIUCVRRCMFC-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[3-(3-methoxyphenyl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(OC)C=CC=2)C2=CC=CC=C2C(N)=N1 GDOBIUCVRRCMFC-UHFFFAOYSA-N 0.000 claims 1
- QLEQZKQBZIKYEV-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[3-(5-methoxypyridin-3-yl)phenyl]isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(OC)C=NC=2)C2=CC=CC=C2C(N)=N1 QLEQZKQBZIKYEV-UHFFFAOYSA-N 0.000 claims 1
- RMAISUWIHRUGBW-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[3-(5-methylfuran-2-yl)phenyl]isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2OC(C)=CC=2)C2=CC=CC=C2C(N)=N1 RMAISUWIHRUGBW-UHFFFAOYSA-N 0.000 claims 1
- FFJATXOBCVGDHP-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[3-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C2=CN(CC(C)C)N=C2)C2=CC=CC=C2C(N)=N1 FFJATXOBCVGDHP-UHFFFAOYSA-N 0.000 claims 1
- NBDIOATZZYXJOM-UHFFFAOYSA-N 3-(5-fluoropyridin-3-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(F)C=NC=1)C(C=1)=CC=CC=1C1=CN=CN=C1 NBDIOATZZYXJOM-UHFFFAOYSA-N 0.000 claims 1
- HYXOWQSRITZXBL-UHFFFAOYSA-N 3-(5-fluoropyridin-3-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(F)C=NC=1)C(C=1)=CC=CC=1C1=CC=CN=C1F HYXOWQSRITZXBL-UHFFFAOYSA-N 0.000 claims 1
- JEJCXMJBQASTNC-UHFFFAOYSA-N 3-[3-(2-fluoro-3-methoxyphenyl)phenyl]-3-(2-methoxypyrimidin-5-yl)isoindol-1-amine Chemical compound C1=NC(OC)=NC=C1C1(C=2C=C(C=CC=2)C=2C(=C(OC)C=CC=2)F)C2=CC=CC=C2C(N)=N1 JEJCXMJBQASTNC-UHFFFAOYSA-N 0.000 claims 1
- NHHIRTVYIYKDOS-UHFFFAOYSA-N 3-[3-(2-fluoro-3-methoxyphenyl)phenyl]-3-(3-fluoropyridin-4-yl)isoindol-1-amine Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C(=CN=CC=2)F)=C1F NHHIRTVYIYKDOS-UHFFFAOYSA-N 0.000 claims 1
- VKJAINYSPZGFJO-UHFFFAOYSA-N 3-[3-(2-fluoro-3-methoxyphenyl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1F VKJAINYSPZGFJO-UHFFFAOYSA-N 0.000 claims 1
- RETGTHQYUNWAHX-UHFFFAOYSA-N 3-[3-(2-fluoro-5-methoxyphenyl)phenyl]-3-(3-fluoropyridin-4-yl)isoindol-1-amine Chemical compound COC1=CC=C(F)C(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C(=CN=CC=2)F)=C1 RETGTHQYUNWAHX-UHFFFAOYSA-N 0.000 claims 1
- JEGZOSORVFTJMV-UHFFFAOYSA-N 3-[3-(2-fluoro-5-methoxyphenyl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound COC1=CC=C(F)C(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 JEGZOSORVFTJMV-UHFFFAOYSA-N 0.000 claims 1
- NKSILXQELSBYMB-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-(2-methoxypyridin-4-yl)isoindol-1-amine Chemical compound C1=NC(OC)=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)=C1 NKSILXQELSBYMB-UHFFFAOYSA-N 0.000 claims 1
- UUSDJWZJKUREMM-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-(2-methoxypyrimidin-5-yl)isoindol-1-amine Chemical compound C1=NC(OC)=NC=C1C1(C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)C2=CC=CC=C2C(N)=N1 UUSDJWZJKUREMM-UHFFFAOYSA-N 0.000 claims 1
- KIZUWEBHRSHYPU-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-(2-propan-2-ylpyridin-4-yl)isoindol-1-amine Chemical compound C1=NC(C(C)C)=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)=C1 KIZUWEBHRSHYPU-UHFFFAOYSA-N 0.000 claims 1
- MLHMUENEDPHQIW-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-(4-methoxy-3-methylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)C2=CC=CC=C2C(N)=N1 MLHMUENEDPHQIW-UHFFFAOYSA-N 0.000 claims 1
- YFTSKYRBVZIRDF-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-(4-methoxyphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)C2=CC=CC=C2C(N)=N1 YFTSKYRBVZIRDF-UHFFFAOYSA-N 0.000 claims 1
- HJVMFIHNKUTKTE-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=C(C(F)(F)F)C=C1 HJVMFIHNKUTKTE-UHFFFAOYSA-N 0.000 claims 1
- PTCIWKKWVHRFHW-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=NC=C1 PTCIWKKWVHRFHW-UHFFFAOYSA-N 0.000 claims 1
- CIDRLEIMPLDXQO-UHFFFAOYSA-N 3-[3-(3,5-dichlorophenyl)phenyl]-3-methylisoindol-1-amine;hydrochloride Chemical compound Cl.N1=C(N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CC(Cl)=CC(Cl)=C1 CIDRLEIMPLDXQO-UHFFFAOYSA-N 0.000 claims 1
- BFHSMQZSRLOQTI-UHFFFAOYSA-N 3-[3-(3-amino-1-pyridin-4-ylisoindol-1-yl)phenyl]thiophene-2-carbaldehyde Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C1=C(SC=C1)C=O)C1=CC=NC=C1 BFHSMQZSRLOQTI-UHFFFAOYSA-N 0.000 claims 1
- ALDNAHUWWBRHNO-UHFFFAOYSA-N 3-[3-(3-chlorophenyl)phenyl]-3-methylisoindol-1-amine Chemical compound N1C(=N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CC=CC(Cl)=C1 ALDNAHUWWBRHNO-UHFFFAOYSA-N 0.000 claims 1
- WCSKTLFQBJLKJT-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)phenyl]-3-methylisoindol-1-amine Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)C2(C)C3=CC=CC=C3C(=N)N2)=C1 WCSKTLFQBJLKJT-UHFFFAOYSA-N 0.000 claims 1
- JUKOGXLVBBEBQA-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)phenyl]-3-pyridin-4-ylisoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 JUKOGXLVBBEBQA-UHFFFAOYSA-N 0.000 claims 1
- QQJUCVADWJXCSY-UHFFFAOYSA-N 3-[3-(3-methyl-2,3-dihydro-1h-isoindol-1-yl)phenyl]benzonitrile Chemical compound C12=CC=CC=C2C(C)NC1C(C=1)=CC=CC=1C1=CC=CC(C#N)=C1 QQJUCVADWJXCSY-UHFFFAOYSA-N 0.000 claims 1
- SKGVVQXEXZIEHI-UHFFFAOYSA-N 3-[3-(5-fluoropyridin-3-yl)phenyl]-3-[4-(trifluoromethoxy)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=C(F)C=NC=1)C1=CC=C(OC(F)(F)F)C=C1 SKGVVQXEXZIEHI-UHFFFAOYSA-N 0.000 claims 1
- UFXWEQDWXOAJIW-UHFFFAOYSA-N 3-[3-(5-fluoropyridin-3-yl)phenyl]-3-[4-(trifluoromethyl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=C(F)C=NC=1)C1=CC=C(C(F)(F)F)C=C1 UFXWEQDWXOAJIW-UHFFFAOYSA-N 0.000 claims 1
- DRJVPYVKKPMDIR-UHFFFAOYSA-N 3-[3-(5-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=C(F)C=NC=1)C1=CC=NC=C1 DRJVPYVKKPMDIR-UHFFFAOYSA-N 0.000 claims 1
- QAKXQJHCDUDOQO-UHFFFAOYSA-N 3-[3-(5-methoxypyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CN=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 QAKXQJHCDUDOQO-UHFFFAOYSA-N 0.000 claims 1
- XIFDYTNQUWAWNB-UHFFFAOYSA-N 3-[3-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C1=NN(CC(C)C)C=C1C1=CC=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 XIFDYTNQUWAWNB-UHFFFAOYSA-N 0.000 claims 1
- BPXXEGHVWKYATP-UHFFFAOYSA-N 3-[3-[3-amino-1-(4-methoxyphenyl)isoindol-1-yl]phenyl]thiophene-2-carbaldehyde Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C2=C(SC=C2)C=O)C2=CC=CC=C2C(N)=N1 BPXXEGHVWKYATP-UHFFFAOYSA-N 0.000 claims 1
- QKRORMCMVMJWEP-UHFFFAOYSA-N 3-[4-fluoro-3-(2-fluoro-3-methoxyphenyl)phenyl]-3-(3-fluoropyridin-4-yl)isoindol-1-amine Chemical compound COC1=CC=CC(C=2C(=CC=C(C=2)C2(C3=CC=CC=C3C(N)=N2)C=2C(=CN=CC=2)F)F)=C1F QKRORMCMVMJWEP-UHFFFAOYSA-N 0.000 claims 1
- ATNOALNMPLKAIU-UHFFFAOYSA-N 3-[4-fluoro-3-(2-fluoropyridin-3-yl)phenyl]-3-(3-fluoropyridin-4-yl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=C(F)C=1C1=CC=CN=C1F ATNOALNMPLKAIU-UHFFFAOYSA-N 0.000 claims 1
- ZUAXXROTZBSKHM-UHFFFAOYSA-N 3-[4-fluoro-3-(2-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C(F)=CC=1)C=1C(=NC=CC=1)F)C1=CC=NC=C1 ZUAXXROTZBSKHM-UHFFFAOYSA-N 0.000 claims 1
- DZQCCINKSULBHS-UHFFFAOYSA-N 3-[4-fluoro-3-(5-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C(F)=CC=1)C=1C=C(F)C=NC=1)C1=CC=NC=C1 DZQCCINKSULBHS-UHFFFAOYSA-N 0.000 claims 1
- VXGRXODOHHHSFX-UHFFFAOYSA-N 3-amino-1-(1h-benzimidazol-2-yl)isoindole-1-carbonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C#N)C1=NC2=CC=CC=C2N1 VXGRXODOHHHSFX-UHFFFAOYSA-N 0.000 claims 1
- NYIANBGHFDKPOM-UHFFFAOYSA-N 3-amino-1-cyano-n-phenylisoindole-1-carboxamide Chemical compound C12=CC=CC=C2C(N)=NC1(C#N)C(=O)NC1=CC=CC=C1 NYIANBGHFDKPOM-UHFFFAOYSA-N 0.000 claims 1
- NQTZOXMJAFUJMD-UHFFFAOYSA-N 3-methyl-3-(3-pyridin-3-ylphenyl)isoindol-1-amine Chemical compound N1C(=N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CC=CN=C1 NQTZOXMJAFUJMD-UHFFFAOYSA-N 0.000 claims 1
- DSTFDMSWHBZXPS-UHFFFAOYSA-N 3-methyl-3-phenylisoindol-1-amine Chemical compound N1C(=N)C2=CC=CC=C2C1(C)C1=CC=CC=C1 DSTFDMSWHBZXPS-UHFFFAOYSA-N 0.000 claims 1
- ZYXCFLDAYHAAAR-UHFFFAOYSA-N 3-methyl-3h-isoindol-1-amine Chemical compound C1=CC=C2C(C)N=C(N)C2=C1 ZYXCFLDAYHAAAR-UHFFFAOYSA-N 0.000 claims 1
- YKXKGPLMYVVUDT-UHFFFAOYSA-N 3-phenyl-3h-isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1C1=CC=CC=C1 YKXKGPLMYVVUDT-UHFFFAOYSA-N 0.000 claims 1
- RZNCMYXAADNFLB-UHFFFAOYSA-N 3-pyridin-4-yl-3-(3-pyridin-3-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=CC=1)C1=CC=NC=C1 RZNCMYXAADNFLB-UHFFFAOYSA-N 0.000 claims 1
- RUJFNISIWQVPLN-UHFFFAOYSA-N 3-pyridin-4-yl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=NC=C1 RUJFNISIWQVPLN-UHFFFAOYSA-N 0.000 claims 1
- CUVALDHWVAAROZ-UHFFFAOYSA-N 4-[3-amino-1-(3-bromophenyl)isoindol-1-yl]benzonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(Br)C=CC=1)C1=CC=C(C#N)C=C1 CUVALDHWVAAROZ-UHFFFAOYSA-N 0.000 claims 1
- RKAZILWLWWIORU-UHFFFAOYSA-N 4-[3-amino-1-(3-pyrimidin-5-ylphenyl)isoindol-1-yl]benzonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=C(C#N)C=C1 RKAZILWLWWIORU-UHFFFAOYSA-N 0.000 claims 1
- JGUHEQYTTIJUJK-UHFFFAOYSA-N 4-[3-amino-1-(4-hydroxy-3,5-dimethylphenyl)isoindol-1-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C)C(O)=C(C)C=2)=C1 JGUHEQYTTIJUJK-UHFFFAOYSA-N 0.000 claims 1
- OPNSCJWHJWVYTM-UHFFFAOYSA-N 4-[3-amino-1-(4-methoxyphenyl)isoindol-1-yl]-2-(3-methoxyphenyl)phenol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C(O)=CC=2)C=2C=C(OC)C=CC=2)C2=CC=CC=C2C(N)=N1 OPNSCJWHJWVYTM-UHFFFAOYSA-N 0.000 claims 1
- DPQXPEOLJIRZGE-UHFFFAOYSA-N 4-[3-amino-1-(4-methoxyphenyl)isoindol-1-yl]-2-pyridin-3-ylphenol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C(O)=CC=2)C=2C=NC=CC=2)C2=CC=CC=C2C(N)=N1 DPQXPEOLJIRZGE-UHFFFAOYSA-N 0.000 claims 1
- JFPLXCZOHUUFBT-UHFFFAOYSA-N 4-[3-amino-1-(4-methoxyphenyl)isoindol-1-yl]-2-pyrimidin-5-ylphenol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C(O)=CC=2)C=2C=NC=NC=2)C2=CC=CC=C2C(N)=N1 JFPLXCZOHUUFBT-UHFFFAOYSA-N 0.000 claims 1
- YHGVNGZOMYDXCF-UHFFFAOYSA-N 4-[3-amino-1-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-yl]benzonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=C(C#N)C=C1 YHGVNGZOMYDXCF-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- RUVUPFARVUNSDR-UHFFFAOYSA-N 5-[3-[3-amino-1-(3-fluoropyridin-4-yl)isoindol-1-yl]phenyl]pyridine-3-carbonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=CC=1C1=CN=CC(C#N)=C1 RUVUPFARVUNSDR-UHFFFAOYSA-N 0.000 claims 1
- VQEFHCMYLLDVIB-UHFFFAOYSA-N 5-chloro-3-pyridin-4-yl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC(Cl)=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=NC=C1 VQEFHCMYLLDVIB-UHFFFAOYSA-N 0.000 claims 1
- BZDDRLVYUUKKIW-UHFFFAOYSA-N 5-fluoro-3-(4-methoxyphenyl)-3-(3-pyridin-3-ylphenyl)isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=CC=2)C2=CC(F)=CC=C2C(N)=N1 BZDDRLVYUUKKIW-UHFFFAOYSA-N 0.000 claims 1
- QZKCUZLROIGMOS-UHFFFAOYSA-N 5-fluoro-3-(4-methoxyphenyl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=NC=2)C2=CC(F)=CC=C2C(N)=N1 QZKCUZLROIGMOS-UHFFFAOYSA-N 0.000 claims 1
- AJQCLXNXTDWIPA-UHFFFAOYSA-N 5-fluoro-3-(4-methoxyphenyl)-3-[3-(3-methoxyphenyl)phenyl]isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(OC)C=CC=2)C2=CC(F)=CC=C2C(N)=N1 AJQCLXNXTDWIPA-UHFFFAOYSA-N 0.000 claims 1
- QFKSZEAFTQSJDV-UHFFFAOYSA-N 5-fluoro-3-(4-methoxyphenyl)-3-[3-(5-methoxypyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(OC)C=NC=2)C2=CC(F)=CC=C2C(N)=N1 QFKSZEAFTQSJDV-UHFFFAOYSA-N 0.000 claims 1
- ZFHOWIHCEQLHCF-UHFFFAOYSA-N 5-fluoro-3-[3-(2-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC(F)=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=NC=C1 ZFHOWIHCEQLHCF-UHFFFAOYSA-N 0.000 claims 1
- WTGLPGYDRWCHNT-UHFFFAOYSA-N 5-fluoro-3-[3-(5-methoxypyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound COC1=CN=CC(C=2C=C(C=CC=2)C2(C3=CC(F)=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 WTGLPGYDRWCHNT-UHFFFAOYSA-N 0.000 claims 1
- XTSAZQMJLSIBNL-UHFFFAOYSA-N 5-fluoro-3-pyridin-4-yl-3-(3-pyridin-3-ylphenyl)isoindol-1-amine Chemical compound C12=CC(F)=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=CC=1)C1=CC=NC=C1 XTSAZQMJLSIBNL-UHFFFAOYSA-N 0.000 claims 1
- COXOKDOOYGRMNE-UHFFFAOYSA-N 5-fluoro-3-pyridin-4-yl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC(F)=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=NC=C1 COXOKDOOYGRMNE-UHFFFAOYSA-N 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010036631 Presenile dementia Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- IDQJDESLNNQYMH-UHFFFAOYSA-N [3-[3-[3-amino-1-(1,3-benzodioxol-5-yl)isoindol-1-yl]phenyl]-5-methoxyphenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC(OS(C)(=O)=O)=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C3OCOC3=CC=2)=C1 IDQJDESLNNQYMH-UHFFFAOYSA-N 0.000 claims 1
- PLKDXPYFYAWJED-UHFFFAOYSA-N [3-[3-[3-amino-1-(4-methoxy-3-methylphenyl)isoindol-1-yl]phenyl]-5-methoxyphenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC(OS(C)(=O)=O)=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C(C)C(OC)=CC=2)=C1 PLKDXPYFYAWJED-UHFFFAOYSA-N 0.000 claims 1
- PNFVQCDSLLSMOG-UHFFFAOYSA-N [3-[3-[3-amino-1-(4-methoxyphenyl)isoindol-1-yl]phenyl]-5-methoxyphenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(OS(C)(=O)=O)C=C(OC)C=2)C2=CC=CC=C2C(N)=N1 PNFVQCDSLLSMOG-UHFFFAOYSA-N 0.000 claims 1
- ZNJSHSINBDEQKB-UHFFFAOYSA-N [4-[3-amino-1-(3-bromophenyl)isoindol-1-yl]phenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OS(=O)(=O)C)=CC=C1C1(C=2C=C(Br)C=CC=2)C2=CC=CC=C2C(N)=N1 ZNJSHSINBDEQKB-UHFFFAOYSA-N 0.000 claims 1
- HRLQVKZRSQKIBW-UHFFFAOYSA-N [4-[3-amino-1-(3-pyrimidin-5-ylphenyl)isoindol-1-yl]phenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OS(=O)(=O)C)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=NC=2)C2=CC=CC=C2C(N)=N1 HRLQVKZRSQKIBW-UHFFFAOYSA-N 0.000 claims 1
- ODBYTPFKZXXSML-UHFFFAOYSA-N [4-[3-amino-1-(4-methoxyphenyl)isoindol-1-yl]-2-(3-methoxyphenyl)phenyl] trifluoromethanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1C1(C=2C=C(C(OS(=O)(=O)C(F)(F)F)=CC=2)C=2C=C(OC)C=CC=2)C2=CC=CC=C2C(N)=N1 ODBYTPFKZXXSML-UHFFFAOYSA-N 0.000 claims 1
- RKTKGQSNQAGRTQ-UHFFFAOYSA-N [4-[3-amino-1-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-yl]phenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OS(=O)(=O)C)=CC=C1C1(C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)C2=CC=CC=C2C(N)=N1 RKTKGQSNQAGRTQ-UHFFFAOYSA-N 0.000 claims 1
- XWVDCYLXEAWZCU-UHFFFAOYSA-N [4-[3-amino-1-[3-(3-methoxy-5-methylsulfonyloxyphenyl)phenyl]isoindol-1-yl]phenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC(OS(C)(=O)=O)=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=CC(OS(C)(=O)=O)=CC=2)=C1 XWVDCYLXEAWZCU-UHFFFAOYSA-N 0.000 claims 1
- ZGMDQLGLYBMLKT-UHFFFAOYSA-N [4-[3-amino-1-[3-(3-methoxyphenyl)phenyl]isoindol-1-yl]phenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=CC(OS(C)(=O)=O)=CC=2)=C1 ZGMDQLGLYBMLKT-UHFFFAOYSA-N 0.000 claims 1
- VFJXZAFJRYDQCM-UHFFFAOYSA-N [4-[3-amino-1-[3-(5-methoxypyridin-3-yl)phenyl]isoindol-1-yl]phenyl] methanesulfonate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CN=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=CC(OS(C)(=O)=O)=CC=2)=C1 VFJXZAFJRYDQCM-UHFFFAOYSA-N 0.000 claims 1
- WHXQTTHQYJFPEH-UHFFFAOYSA-N acetic acid;2-[3-(3-amino-1-cyclopropylisoindol-1-yl)phenyl]-4-methoxybenzonitrile Chemical compound CC(O)=O.COC1=CC=C(C#N)C(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C2CC2)=C1 WHXQTTHQYJFPEH-UHFFFAOYSA-N 0.000 claims 1
- SXYVIPPBELUZSU-UHFFFAOYSA-N acetic acid;2-[3-(3-amino-1-methylisoindol-1-yl)phenyl]-4-methoxybenzonitrile Chemical compound CC(O)=O.COC1=CC=C(C#N)C(C=2C=C(C=CC=2)C2(C)C3=CC=CC=C3C(N)=N2)=C1 SXYVIPPBELUZSU-UHFFFAOYSA-N 0.000 claims 1
- RWSXLZHIIAOCND-UHFFFAOYSA-N acetic acid;3-[3-(2-fluoropyridin-3-yl)phenyl]-3-methylisoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CC=CN=C1F RWSXLZHIIAOCND-UHFFFAOYSA-N 0.000 claims 1
- YKKQOJCALFONIU-UHFFFAOYSA-N acetic acid;3-[3-(3,5-dichlorophenyl)phenyl]-3-(4-methoxyphenyl)isoindol-1-amine Chemical compound CC(O)=O.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(Cl)C=C(Cl)C=2)C2=CC=CC=C2C(N)=N1 YKKQOJCALFONIU-UHFFFAOYSA-N 0.000 claims 1
- XBKNYNDDSNNHLN-UHFFFAOYSA-N acetic acid;3-[3-(5-fluoropyridin-3-yl)phenyl]-3-methylisoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CN=CC(F)=C1 XBKNYNDDSNNHLN-UHFFFAOYSA-N 0.000 claims 1
- IJFIEUYKOPJJBV-UHFFFAOYSA-N acetic acid;3-[3-(5-methylfuran-2-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound CC(O)=O.O1C(C)=CC=C1C1=CC=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 IJFIEUYKOPJJBV-UHFFFAOYSA-N 0.000 claims 1
- HGBZLRDFRLWCEE-UHFFFAOYSA-N acetic acid;3-cyclopropyl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound CC(O)=O.C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1CC1 HGBZLRDFRLWCEE-UHFFFAOYSA-N 0.000 claims 1
- RTXLJMPVHPGCQK-UHFFFAOYSA-N acetic acid;3-methyl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CN=CN=C1 RTXLJMPVHPGCQK-UHFFFAOYSA-N 0.000 claims 1
- NHEFJNWOSSJDEH-UHFFFAOYSA-N acetic acid;3-propan-2-yl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C(C)C)C(C=1)=CC=CC=1C1=CN=CN=C1 NHEFJNWOSSJDEH-UHFFFAOYSA-N 0.000 claims 1
- MBMRYIYFZAGUFP-UHFFFAOYSA-N acetic acid;5-[3-(3-amino-1-pyridin-4-ylisoindol-1-yl)phenyl]pyridine-3-carbonitrile Chemical compound CC(O)=O.C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=C(C=NC=1)C#N)C1=CC=NC=C1 MBMRYIYFZAGUFP-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 210000004227 basal ganglia Anatomy 0.000 claims 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002068 genetic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000006984 memory degeneration Effects 0.000 claims 1
- 208000023060 memory loss Diseases 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81580006P | 2006-06-22 | 2006-06-22 | |
| US81855706P | 2006-07-05 | 2006-07-05 | |
| US89124207P | 2007-02-23 | 2007-02-23 | |
| PCT/SE2007/000601 WO2007149033A1 (en) | 2006-06-22 | 2007-06-20 | Substituted isoindoles as bace inhibitors and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009541311A JP2009541311A (ja) | 2009-11-26 |
| JP2009541311A5 true JP2009541311A5 (https=) | 2010-09-16 |
Family
ID=38833680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009516446A Pending JP2009541311A (ja) | 2006-06-22 | 2007-06-20 | Ｂａｃｅインヒビターとしての置換イソインドール類及びそれらの使用 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7855213B2 (https=) |
| EP (1) | EP2035378A4 (https=) |
| JP (1) | JP2009541311A (https=) |
| KR (1) | KR20090031585A (https=) |
| AR (1) | AR061564A1 (https=) |
| AU (1) | AU2007261749B2 (https=) |
| CA (1) | CA2656625A1 (https=) |
| CL (1) | CL2007001830A1 (https=) |
| EC (1) | ECSP088972A (https=) |
| IL (1) | IL195670A0 (https=) |
| MX (1) | MX2008015719A (https=) |
| MY (1) | MY147390A (https=) |
| NO (1) | NO20090246L (https=) |
| NZ (1) | NZ574262A (https=) |
| TW (1) | TW200815349A (https=) |
| UY (1) | UY30426A1 (https=) |
| WO (1) | WO2007149033A1 (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7592348B2 (en) | 2003-12-15 | 2009-09-22 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| US7763609B2 (en) | 2003-12-15 | 2010-07-27 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| US7700603B2 (en) | 2003-12-15 | 2010-04-20 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| DE602005007245D1 (https=) | 2004-07-28 | 2008-07-10 | Schering Corp | |
| RU2008100164A (ru) * | 2005-06-14 | 2009-07-20 | Шеринг Корпорейшн (US) | Получение и применение соединений в качестве ингибиторов протеаз |
| MX2007016180A (es) | 2005-06-14 | 2008-03-07 | Schering Corp | Inhibidores de aspartil proteasas. |
| KR20090015967A (ko) | 2006-06-12 | 2009-02-12 | 쉐링 코포레이션 | 헤테로사이클릭 아스파르틸 프로테아제 억제제 |
| TW200815349A (en) * | 2006-06-22 | 2008-04-01 | Astrazeneca Ab | New compounds |
| TW200902499A (en) | 2007-05-15 | 2009-01-16 | Astrazeneca Ab | New compounds |
| WO2009005471A1 (en) * | 2007-07-05 | 2009-01-08 | Astrazeneca Ab | Aryl and heteroaryl substituted isoindole derivatives as bace inhibitors |
| WO2009005470A1 (en) * | 2007-07-05 | 2009-01-08 | Astrazeneca Ab | Aryl and heteroaryl substituted isoindole derivatives as bace inhibitors |
| US8450331B2 (en) | 2008-04-22 | 2013-05-28 | Merck Sharp & Dohme Corp. | Thiophenyl-substituted 2-imino-3-methyl pyrrolo pyrimidinone compounds as BACE-1 inhibitors, compositions, and their use |
| CA2736130C (en) | 2008-09-11 | 2014-01-14 | Amgen Inc. | Spiro-tetracyclic ring compounds as beta-secretase modulators and methods of use |
| CA2742897A1 (en) * | 2008-11-06 | 2010-05-14 | Astrazeneca Ab | Modulators of amyloid beta. |
| TW201020244A (en) * | 2008-11-14 | 2010-06-01 | Astrazeneca Ab | New compounds |
| US20100125087A1 (en) * | 2008-11-14 | 2010-05-20 | Astrazeneca Ab | New compounds 575 |
| US20100125081A1 (en) * | 2008-11-14 | 2010-05-20 | Astrazeneca Ab | New compounds 574 |
| WO2011002409A1 (en) * | 2009-07-02 | 2011-01-06 | Astrazeneca Ab | 5h-pyrrolo[3,4-£>]pyrazin-7-amine derivatives inhibitors of beta-secretase |
| 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 |
| EP2485920B1 (en) | 2009-10-08 | 2016-04-27 | Merck Sharp & Dohme Corp. | Pentafluorosulfur imino heterocyclic compounds as bace-1 inhibitors, compositions, and their use |
| US8563543B2 (en) | 2009-10-08 | 2013-10-22 | Merck Sharp & Dohme Corp. | Iminothiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| UA108363C2 (uk) | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
| EP2485590B1 (en) | 2009-10-08 | 2015-01-07 | Merck Sharp & Dohme Corp. | Pentafluorosulfur imino heterocyclic compounds as bace-1 inhibitors, compositions, and their use |
| MX2012010657A (es) | 2010-03-15 | 2013-02-07 | Amgen Inc | Compuestos de espiro amino-dihidrooxazina y amino-dihidrotiazina como moduladores de beta-secretasa y su uso medico. |
| EP2547685A1 (en) | 2010-03-15 | 2013-01-23 | Amgen Inc. | Spiro-tetracyclic ring compounds as beta - secretase modulators |
| WO2011142716A1 (en) * | 2010-05-12 | 2011-11-17 | Astrazeneca Ab | Novel hemifumarate salt of isoindole compound acting as bace inhibitor |
| WO2012019056A1 (en) | 2010-08-05 | 2012-02-09 | Amgen Inc. | Amino-iso-indole, amino-aza-iso-indole, amino-dihydroisoquinoline and amino-benzoxazine compounds as beta-secretase modulators and methods of use |
| EP2643299B1 (en) | 2010-11-22 | 2016-06-22 | Noscira, S.A. | Bipyridine sulfonamide derivatives for the treatment of neurodegenerative diseases or conditions |
| EP2673279A1 (en) | 2011-02-07 | 2013-12-18 | Amgen Inc. | 5-amino-oxazepine and 5-amino-thiazepane compounds as beta-secretase antagonists and methods of use |
| EP2694489B1 (en) | 2011-04-07 | 2017-09-06 | Merck Sharp & Dohme Corp. | C5-c6 oxacyclic-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| RU2014111055A (ru) | 2011-08-22 | 2015-09-27 | Мерк Шарп И Доум Корп. | 2-спирозамещенные иминотиазины и их моно- и диоксиды в качестве ингибиторов bace, композиции и их применение |
| WO2013044092A1 (en) | 2011-09-21 | 2013-03-28 | Amgen Inc. | Amino-oxazines and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
| AU2013235422B2 (en) | 2012-03-19 | 2016-12-15 | Buck Institute For Research On Aging | APP specific BACE inhibitors (ASBIs) and uses thereof |
| WO2014062553A1 (en) | 2012-10-17 | 2014-04-24 | Merck Sharp & Dohme Corp. | Tricyclic substituted thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| EP2908825B1 (en) | 2012-10-17 | 2018-04-18 | Merck Sharp & Dohme Corp. | Tricyclic substituted thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| WO2014078314A1 (en) | 2012-11-15 | 2014-05-22 | Amgen Inc. | Amino-oxazine and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
| US20140371283A1 (en) | 2013-02-12 | 2014-12-18 | Buck Institute For Research On Aging | Hydantoins that modulate bace-mediated app processing |
| CN121240860A (zh) * | 2023-05-16 | 2025-12-30 | 斯普林渥克斯治疗有限公司 | 用于抑制yap/taz-tead的苯并咪唑及相关类似物 |
Family Cites Families (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4605642A (en) * | 1984-02-23 | 1986-08-12 | The Salk Institute For Biological Studies | CRF antagonists |
| US5063245A (en) * | 1990-03-28 | 1991-11-05 | Nova Pharmaceutical Corporation | Corticotropin-releasing factor antagonism compounds |
| AU702293B2 (en) * | 1993-10-27 | 1999-02-18 | Athena Neurosciences, Inc. | Transgenic animals harboring APP allele having Swedish mutation |
| US5877399A (en) * | 1994-01-27 | 1999-03-02 | Johns Hopkins University | Transgenic mice expressing APP-Swedish mutation develop progressive neurologic disease |
| DE4419849A1 (de) * | 1994-06-07 | 1995-12-14 | Hoechst Ag | Isoindolinpigmente |
| WO1995034563A1 (en) | 1994-06-16 | 1995-12-21 | Pfizer Inc. | Pyrazolo and pyrrolopyridines |
| DE19516804A1 (de) | 1995-05-08 | 1996-11-14 | Hoechst Ag | Isoindolinpigmente auf Basis von Aminochinoxalindionen |
| US5942400A (en) * | 1995-06-07 | 1999-08-24 | Elan Pharmaceuticals, Inc. | Assays for detecting β-secretase |
| US5744346A (en) * | 1995-06-07 | 1998-04-28 | Athena Neurosciences, Inc. | β-secretase |
| US6211235B1 (en) * | 1996-11-22 | 2001-04-03 | Elan Pharmaceuticals, Inc. | Compounds for inhibiting β-amyloid peptide release and/or its synthesis |
| GB9701684D0 (en) | 1997-01-28 | 1997-03-19 | Smithkline Beecham Plc | Novel compounds |
| EP1012151B1 (en) | 1997-09-02 | 2002-08-07 | Bristol-Myers Squibb Pharma Company | Heterocyclyl-substituted ring-fused pyridines and pyrimidines as corticotropin releasing hormone (crh) antagonists, useful for treating cns and stress-related disorders |
| US5981168A (en) * | 1998-05-15 | 1999-11-09 | The University Of British Columbia | Method and composition for modulating amyloidosis |
| CN1300320C (zh) | 1998-09-24 | 2007-02-14 | 法玛西雅厄普约翰美国公司 | 阿尔茨海默氏疾病分泌酶 |
| US6245884B1 (en) * | 1998-10-16 | 2001-06-12 | Vivian Y. H. Hook | Secretases related to alzheimer's dementia |
| US6313268B1 (en) * | 1998-10-16 | 2001-11-06 | Vivian Y. H. Hook | Secretases related to Alzheimer's dementia |
| CN1390232A (zh) | 1999-02-10 | 2003-01-08 | 艾兰制药公司 | 人β分泌酶、抑制剂、其组合物和用途 |
| WO2000058479A1 (en) | 1999-03-26 | 2000-10-05 | Amgen Inc. | Beta secretase genes and polypeptides |
| US6376530B1 (en) * | 1999-05-10 | 2002-04-23 | Merck & Co., Inc. | Cyclic amidines useful as NMDA NR2B antagonists |
| EP1192177A1 (en) | 1999-06-15 | 2002-04-03 | Elan Pharmaceuticals, Inc. | Statine-derived tetrapeptide inhibitors of beta-secretase |
| EP1196609A2 (en) | 1999-06-28 | 2002-04-17 | Oklahoma Medical Research Foundation | Catalytically active recombinant memapsin and methods of use thereof |
| PT1224297E (pt) | 1999-09-23 | 2009-08-17 | Pharmacia & Upjohn Co Llc | Secretase da doença de alzheimer, seus substratos app e suas utilizações |
| GB9924957D0 (en) | 1999-10-21 | 1999-12-22 | Smithkline Beecham Plc | Novel treatment |
| EP1299352B1 (en) | 2000-06-30 | 2005-12-28 | Elan Pharmaceuticals, Inc. | 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 |
| US6846813B2 (en) | 2000-06-30 | 2005-01-25 | Pharmacia & Upjohn Company | Compounds to treat alzheimer's disease |
| AU2001281250A1 (en) | 2000-08-11 | 2002-02-25 | The Brigham And Women's Hospital, Inc. | (hydroxyethyl)ureas as inhibitors of alzheimer's beta-amyloid production |
| 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) |
| JP2004149429A (ja) * | 2002-10-29 | 2004-05-27 | Takeda Chem Ind Ltd | インドール化合物およびその用途 |
| PT1699455E (pt) | 2003-12-15 | 2013-08-27 | Merck Sharp & Dohme | Inibidores de protease de aspartilo heterocíclicos |
| US7592348B2 (en) | 2003-12-15 | 2009-09-22 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| JP2007530696A (ja) | 2004-03-30 | 2007-11-01 | メルク エンド カムパニー インコーポレーテッド | アスパラギン酸プロテアーゼ阻害剤として有用な２−アミノチアゾール化合物 |
| EP1744747A4 (en) * | 2004-04-26 | 2009-12-02 | Univ Vanderbilt | INDIC ACID AND INDULECTIC ACID DERIVATIVES AS THERAPEUTIC ACTIVITIES WITH REDUCED GASTROINTESTINAL TOXICITY |
| WO2005123672A2 (en) | 2004-06-14 | 2005-12-29 | Takeda San Diego, Inc. | Kinase inhibitors |
| CA2578600A1 (en) * | 2004-06-16 | 2006-01-26 | Wyeth | Diphenylimidazopyrimidine and -imidazole amines as inhibitors of b-secretase |
| BRPI0512213A (pt) * | 2004-06-16 | 2008-02-19 | Wyeth Corp | método para tratamento, prevenção ou melhora de uma doença ou distúrbio; composição farmacêutica; processo para a preparação de um composto; e uso de um composto |
| EP1783219A1 (en) | 2004-07-09 | 2007-05-09 | Genofunction, Inc. | Method of searching for novel drug discovery targets |
| JPWO2006006527A1 (ja) | 2004-07-12 | 2008-04-24 | 大日本印刷株式会社 | 電磁波シールドフィルタ |
| CN101035772B (zh) * | 2004-08-06 | 2011-12-14 | 詹森药业有限公司 | 用作β-分泌酶(BACE)抑制剂的2-氨基喹唑啉衍生物 |
| TW200613272A (en) | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
| MX2007003336A (es) | 2004-09-21 | 2007-06-05 | Athersys Inc | Acidos aceticos de indol que muestran antagonismo de receptor crth2 y usos de los mismos. |
| EP1802587A4 (en) | 2004-10-15 | 2010-02-17 | Astrazeneca Ab | SUBSTITUTED AMINO BINDINGS AND THEIR APPLICATIONS |
| WO2006041405A1 (en) | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Substituted amino-pyrimidones and uses thereof |
| EP1831170A4 (en) | 2004-12-14 | 2009-10-14 | Astrazeneca Ab | SUBSTITUTED AMINOPYRIDINES AND THEIR USE |
| CA2593515A1 (en) | 2005-01-14 | 2006-07-20 | Wyeth | Amino-imidazolones for the inhibition of beta-secretase |
| ES2400287T3 (es) | 2005-03-14 | 2013-04-08 | High Point Pharmaceuticals, Llc | Derivados de benzazol, composiciones y procedimientos de uso como inhibidores de beta-secretasa |
| CN101198597B (zh) | 2005-06-14 | 2011-11-16 | 先灵公司 | 作为天冬氨酰基蛋白酶抑制剂的化合物的制备和用途 |
| RU2008100164A (ru) | 2005-06-14 | 2009-07-20 | Шеринг Корпорейшн (US) | Получение и применение соединений в качестве ингибиторов протеаз |
| CA2609562A1 (en) * | 2005-06-14 | 2006-12-28 | Schering Corporation | Macrocyclic heterocyclic aspartyl protease inhibitors |
| AU2006259609A1 (en) | 2005-06-14 | 2006-12-28 | Pharmacopeia, Inc. | Aspartyl protease inhibitors |
| MX2007016180A (es) | 2005-06-14 | 2008-03-07 | Schering Corp | Inhibidores de aspartil proteasas. |
| MX2007016186A (es) | 2005-06-14 | 2008-03-07 | Schering Corp | Preparacion y uso de inhibidores de proteasas. |
| WO2007005404A1 (en) * | 2005-06-30 | 2007-01-11 | Wyeth | AMINO-5-(6-MEMBERED)HETEROARYLIMIDAZOLONE COMPOUNDS AND THE USE THEREOF FOR ß-SECRETASE MODULATION |
| TW200738683A (en) * | 2005-06-30 | 2007-10-16 | Wyeth Corp | Amino-5-(5-membered)heteroarylimidazolone compounds and the use thereof for β-secretase modulation |
| US8211904B2 (en) | 2005-07-18 | 2012-07-03 | Merck, Sharp & Dohme Corp. | Spiropiperidine beta-secretase inhibitors for the treatment of alzheimer's disease |
| US7601751B2 (en) * | 2005-09-01 | 2009-10-13 | Bristol-Myers Squibb Company | Indole acetic acid acyl guanidines as β-secretase inhibitors |
| RU2416603C9 (ru) | 2005-10-25 | 2012-06-20 | Сионоги Энд Ко., Лтд. | Производные аминодигидротиазина |
| WO2007050721A2 (en) * | 2005-10-27 | 2007-05-03 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| PE20070798A1 (es) * | 2005-10-31 | 2007-08-24 | Schering Corp | Compuestos heterociclicos como inhibidores de aspartil proteasas |
| TW200804290A (en) | 2005-11-15 | 2008-01-16 | Astrazeneca Ab | Compounds and uses thereof |
| WO2007058582A1 (en) | 2005-11-15 | 2007-05-24 | Astrazeneca Ab | Novel 2-aminopyrimidinone or 2-aminopyridinone derivatives and their use |
| JP2009515950A (ja) | 2005-11-15 | 2009-04-16 | アストラゼネカ・アクチエボラーグ | 新規な２−アミノピリミジン誘導体およびその使用 |
| CN101360720A (zh) | 2005-11-15 | 2009-02-04 | 阿斯利康(瑞典)有限公司 | 新颖的2-氨基嘧啶酮衍生物及其用途 |
| TW200734311A (en) | 2005-11-21 | 2007-09-16 | Astrazeneca Ab | New compounds |
| JP2009520686A (ja) | 2005-11-21 | 2009-05-28 | アストラゼネカ・アクチエボラーグ | 新規な２−アミノ−イミダゾール−４−オン化合物並びに認知障害、アルツハイマー病、神経変性及び認知症の治療に使用する医薬の製造におけるその使用 |
| AR058381A1 (es) | 2005-12-19 | 2008-01-30 | Astrazeneca Ab | Compuestos derivados de 2-aminopiridin-4-onas y una composicion farmaceutica |
| US20090099217A1 (en) | 2006-04-05 | 2009-04-16 | Astex Therapeutics Ltd. | 2-Aminopyrimidin-4-Ones And Their Use For Treating Or Preventing Alpha Beta-Related Pathologies |
| TW200808751A (en) | 2006-04-13 | 2008-02-16 | Astrazeneca Ab | New compounds |
| KR20090015967A (ko) | 2006-06-12 | 2009-02-12 | 쉐링 코포레이션 | 헤테로사이클릭 아스파르틸 프로테아제 억제제 |
| TW200815443A (en) | 2006-06-14 | 2008-04-01 | Astrazeneca Ab | Novel compounds I |
| TW200815447A (en) | 2006-06-14 | 2008-04-01 | Astrazeneca Ab | Novel compounds IV |
| TW200815449A (en) | 2006-06-14 | 2008-04-01 | Astrazeneca Ab | Novel compounds II |
| TW200808796A (en) | 2006-06-14 | 2008-02-16 | Astrazeneca Ab | New compounds III |
| TW200815349A (en) | 2006-06-22 | 2008-04-01 | Astrazeneca Ab | New compounds |
| WO2008063114A1 (en) | 2006-11-20 | 2008-05-29 | Astrazeneca Ab | Amino- imidazolones and their use as medicament for treating cognitive impairment alzheimer disease, neurodegeneration and dementia |
| TW200831484A (en) | 2006-12-20 | 2008-08-01 | Astrazeneca Ab | New compounds |
| TW200831091A (en) | 2006-12-20 | 2008-08-01 | Astrazeneca Ab | New compounds |
| WO2008076044A1 (en) | 2006-12-20 | 2008-06-26 | Astrazeneca Ab | Novel 2-amino-5, 5-diaryl-imidazol-4-ones |
| TW200902499A (en) * | 2007-05-15 | 2009-01-16 | Astrazeneca Ab | New compounds |
| TW200902503A (en) | 2007-05-15 | 2009-01-16 | Astrazeneca Ab | New compounds |
| WO2009005470A1 (en) | 2007-07-05 | 2009-01-08 | Astrazeneca Ab | Aryl and heteroaryl substituted isoindole derivatives as bace inhibitors |
| WO2009005471A1 (en) | 2007-07-05 | 2009-01-08 | Astrazeneca Ab | Aryl and heteroaryl substituted isoindole derivatives as bace inhibitors |
| US20100125087A1 (en) * | 2008-11-14 | 2010-05-20 | Astrazeneca Ab | New compounds 575 |
| US20100125081A1 (en) * | 2008-11-14 | 2010-05-20 | Astrazeneca Ab | New compounds 574 |
| TW201020244A (en) * | 2008-11-14 | 2010-06-01 | Astrazeneca Ab | New compounds |
-
2007
- 2007-06-11 TW TW096121008A patent/TW200815349A/zh unknown
- 2007-06-13 US US11/762,487 patent/US7855213B2/en not_active Expired - Fee Related
- 2007-06-20 AU AU2007261749A patent/AU2007261749B2/en not_active Ceased
- 2007-06-20 KR KR1020097001336A patent/KR20090031585A/ko not_active Ceased
- 2007-06-20 CA CA002656625A patent/CA2656625A1/en not_active Abandoned
- 2007-06-20 WO PCT/SE2007/000601 patent/WO2007149033A1/en not_active Ceased
- 2007-06-20 EP EP07748264A patent/EP2035378A4/en not_active Withdrawn
- 2007-06-20 NZ NZ574262A patent/NZ574262A/en not_active IP Right Cessation
- 2007-06-20 JP JP2009516446A patent/JP2009541311A/ja active Pending
- 2007-06-20 MX MX2008015719A patent/MX2008015719A/es active IP Right Grant
- 2007-06-20 MY MYPI20085213A patent/MY147390A/en unknown
- 2007-06-21 CL CL200701830A patent/CL2007001830A1/es unknown
- 2007-06-21 AR ARP070102733A patent/AR061564A1/es not_active Application Discontinuation
- 2007-06-21 UY UY30426A patent/UY30426A1/es not_active Application Discontinuation
-
2008
- 2008-12-02 IL IL195670A patent/IL195670A0/en unknown
- 2008-12-12 EC EC2008008972A patent/ECSP088972A/es unknown
-
2009
- 2009-01-15 NO NO20090246A patent/NO20090246L/no not_active Application Discontinuation
-
2010
- 2010-11-11 US US12/944,145 patent/US20110059992A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009541311A5 (https=) | ||
| JP5529004B2 (ja) | Ｈｓｐ９０阻害剤として有用なトリアジノンおよびジアジノン誘導体 | |
| AU2015279377B2 (en) | Indolin-2-one or pyrrolo-pyridin-2-one derivatives | |
| US8329736B2 (en) | Triazole compounds that modulate HSP90 activity | |
| JP5441691B2 (ja) | Ｈｓｐ９０活性を調節するトリアゾール化合物 | |
| JP2011515462A5 (https=) | ||
| JP2008513514A5 (https=) | ||
| CA2796967A1 (en) | Heterocyclic derivatives as alk inhibitors | |
| WO2019025440A1 (en) | COMBINATION OF ATR KINASE INHIBITORS AND PD-1 / PD-L1 INHIBITORS | |
| TW200843740A (en) | Triazole compounds that modulate Hsp90 activity | |
| EP3585365B1 (en) | Combination of atr kinase inhibitors with parp inhibitors | |
| WO2018153969A1 (en) | Combination of atr kinase inhibitors with radium-223 salt | |
| JP2017536342A5 (https=) | ||
| CA2868323A1 (en) | Novel triazole compounds that modulate hsp90 activity | |
| JP2009501745A5 (https=) | ||
| WO2018153972A1 (en) | Combination of atr kinase inhibitors and antiandrogens | |
| KR101457027B1 (ko) | 트리아진 유도체와 이들의 치료적 용도 | |
| RU2015106437A (ru) | Производные имидазо[2,1]тиазол-3-она, пригодные в качестве диагностических агентов для болезни альцгеймера | |
| JP2006522775A5 (https=) | ||
| JP2006504714A5 (https=) | ||
| RU2008148901A (ru) | Замещенные изоиндолы в качестве ингибиторов васе и их применение | |
| WO2025040546A1 (en) | Pyrazole compounds as cullin ring ubiquitin ligase compounds | |
| HK1230199A1 (en) | Indolin-2-one or pyrrolo-pyridin-2-one derivatives |