JP2012515205A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012515205A5 JP2012515205A5 JP2011546297A JP2011546297A JP2012515205A5 JP 2012515205 A5 JP2012515205 A5 JP 2012515205A5 JP 2011546297 A JP2011546297 A JP 2011546297A JP 2011546297 A JP2011546297 A JP 2011546297A JP 2012515205 A5 JP2012515205 A5 JP 2012515205A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- tetrahydro
- phenyl
- azepin
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 hydroxy, amino Chemical group 0.000 claims 120
- GJPUTKWVQJEZPE-UHFFFAOYSA-N 1h-azepin-2-amine Chemical compound NC1=CC=CC=CN1 GJPUTKWVQJEZPE-UHFFFAOYSA-N 0.000 claims 45
- 125000005843 halogen group Chemical group 0.000 claims 40
- 125000000217 alkyl group Chemical group 0.000 claims 38
- 125000003545 alkoxy group Chemical group 0.000 claims 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 28
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 22
- 125000004076 pyridyl group Chemical group 0.000 claims 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- BXLHOSHUHPPGDV-UHFFFAOYSA-N 1h-azepin-2-ol Chemical compound OC1=CC=CC=CN1 BXLHOSHUHPPGDV-UHFFFAOYSA-N 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000001425 triazolyl group Chemical group 0.000 claims 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 201000002832 Lewy body dementia Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 201000008319 inclusion body myositis Diseases 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- OIZXNQQCBZBLPI-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3,4,5-trifluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC(F)=C(F)C(F)=C1 OIZXNQQCBZBLPI-UHFFFAOYSA-N 0.000 claims 2
- IECYPDLRLARBTB-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 IECYPDLRLARBTB-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- UURWCDYFZCJXMM-QGZVFWFLSA-N (8r)-n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-8-[4-(trifluoromethoxy)phenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCC[C@H](C=3C=CC(OC(F)(F)F)=CC=3)C2=N1 UURWCDYFZCJXMM-QGZVFWFLSA-N 0.000 claims 1
- GXUIBEGWVDCQHE-QGZVFWFLSA-N (8r)-n-[3-fluoro-4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound CC1=NC=NN1C(C(=C1)F)=CC=C1NC1=NN2CCC[C@H](C=3C=CC(F)=CC=3)C2=N1 GXUIBEGWVDCQHE-QGZVFWFLSA-N 0.000 claims 1
- UURWCDYFZCJXMM-KRWDZBQOSA-N (8s)-n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-8-[4-(trifluoromethoxy)phenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCC[C@@H](C=3C=CC(OC(F)(F)F)=CC=3)C2=N1 UURWCDYFZCJXMM-KRWDZBQOSA-N 0.000 claims 1
- GXUIBEGWVDCQHE-KRWDZBQOSA-N (8s)-n-[3-fluoro-4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound CC1=NC=NN1C(C(=C1)F)=CC=C1NC1=NN2CCC[C@@H](C=3C=CC(F)=CC=3)C2=N1 GXUIBEGWVDCQHE-KRWDZBQOSA-N 0.000 claims 1
- ZQKKUACPEQGYGK-LJQANCHMSA-N (9r)-9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CC=CC2)NC=2C=C(C(=CC=2)N2N=C(C)N=C2)OC)=CC=C(F)C=C1 ZQKKUACPEQGYGK-LJQANCHMSA-N 0.000 claims 1
- GGXUXERMYNGBEC-QGZVFWFLSA-N (9r)-n-[2-fluoro-5-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(trifluoromethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2F)N2N=C(C)N=C2)OC)=CC=C(OC(F)(F)F)C=C1 GGXUXERMYNGBEC-QGZVFWFLSA-N 0.000 claims 1
- XOYMUEMCZKLHHH-QGZVFWFLSA-N (9r)-n-[4-(3-chloro-1,2,4-triazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2N=C(Cl)N=C2)OC)=CC=C(F)C=C1 XOYMUEMCZKLHHH-QGZVFWFLSA-N 0.000 claims 1
- VNJJNEUHBAJYST-QGZVFWFLSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2,4-difluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1F VNJJNEUHBAJYST-QGZVFWFLSA-N 0.000 claims 1
- UPLRVCGMDNCGNC-QGZVFWFLSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=CC=C1F UPLRVCGMDNCGNC-QGZVFWFLSA-N 0.000 claims 1
- OIZXNQQCBZBLPI-OAHLLOKOSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3,4,5-trifluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC(F)=C(F)C(F)=C1 OIZXNQQCBZBLPI-OAHLLOKOSA-N 0.000 claims 1
- XRRCVLNYATYOLT-GOSISDBHSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=CC(F)=C1 XRRCVLNYATYOLT-GOSISDBHSA-N 0.000 claims 1
- IECYPDLRLARBTB-GOSISDBHSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCCC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1 IECYPDLRLARBTB-GOSISDBHSA-N 0.000 claims 1
- PETFLWQZSWIXIC-LJQANCHMSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7-methylidene-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CCC(=C)C2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1 PETFLWQZSWIXIC-LJQANCHMSA-N 0.000 claims 1
- VTHAWVAAIFRQTO-GOSISDBHSA-N (9r)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1([C@@H]2C3=NC(=NN3CC=CC2)NC=2C=C(C(=CC=2)N2C=C(Cl)N=C2)OC)=CC=C(F)C=C1 VTHAWVAAIFRQTO-GOSISDBHSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- KTTWWFBBFMNIEM-UHFFFAOYSA-N 2-(4-chloroimidazol-1-yl)-5-[[8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(F)=CC=C1C1C2=NC(NC=3C=C(C(=CC=3)N3C=C(Cl)N=C3)C#N)=NN2CCC1 KTTWWFBBFMNIEM-UHFFFAOYSA-N 0.000 claims 1
- CTDJIZCCHAQGEI-UHFFFAOYSA-N 2-[4-(4-chloroimidazol-1-yl)-3-methoxyanilino]-7-ethyl-9-(4-fluorophenyl)-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-7-ol Chemical compound N1=C2C(C=3C=CC(F)=CC=3)CC(CC)(O)CCN2N=C1NC(C=C1OC)=CC=C1N1C=NC(Cl)=C1 CTDJIZCCHAQGEI-UHFFFAOYSA-N 0.000 claims 1
- RVZJLRQEPROIIG-UHFFFAOYSA-N 2-[4-(4-chloroimidazol-1-yl)-3-methoxyanilino]-9-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-9-ol Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=N1)N=C2N1CCCCC2(O)C1=CC=C(F)C=C1 RVZJLRQEPROIIG-UHFFFAOYSA-N 0.000 claims 1
- VRZTUHJDNATGOH-UHFFFAOYSA-N 2-[4-(4-chloroimidazol-1-yl)-3-methoxyanilino]-9-(4-fluorophenyl)-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-7-one Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCC(=O)C2)N=C1C2C1=CC=C(F)C=C1 VRZTUHJDNATGOH-UHFFFAOYSA-N 0.000 claims 1
- MGHRMDCRSZRYRT-UHFFFAOYSA-N 2-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7-n,7-n-dimethyl-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepine-2,7-diamine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCC(C2)N(C)C)N=C1C2C1=CC=C(F)C=C1 MGHRMDCRSZRYRT-UHFFFAOYSA-N 0.000 claims 1
- VWUXQVNBSGWPPY-UHFFFAOYSA-N 2-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7-n-methyl-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepine-2,7-diamine Chemical compound N1=C2C(C=3C=CC(F)=CC=3)CC(NC)CCN2N=C1NC(C=C1OC)=CC=C1N1C=NC(Cl)=C1 VWUXQVNBSGWPPY-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- BYJRFFLTMXJDIH-UHFFFAOYSA-N 4-[2-[4-(4-chloroimidazol-1-yl)-3-methoxyanilino]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-9-yl]benzonitrile Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(C#N)C=C1 BYJRFFLTMXJDIH-UHFFFAOYSA-N 0.000 claims 1
- GDTOJGYZPQAPBA-UHFFFAOYSA-N 7-(azetidin-1-yl)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC2)N=C1C(C=1C=CC(F)=CC=1)CC2N1CCC1 GDTOJGYZPQAPBA-UHFFFAOYSA-N 0.000 claims 1
- JXRQWNISXMFUJF-UHFFFAOYSA-N 9-(4-bromophenyl)-n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(Br)C=C1 JXRQWNISXMFUJF-UHFFFAOYSA-N 0.000 claims 1
- QZSIMDGUIRZHLV-UHFFFAOYSA-N 9-(4-chlorophenyl)-n-[3-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2=CN(C)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(Cl)C=C1 QZSIMDGUIRZHLV-UHFFFAOYSA-N 0.000 claims 1
- ATMGMCKLGOHVRT-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(C=2ON=C(C)N=2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 ATMGMCKLGOHVRT-UHFFFAOYSA-N 0.000 claims 1
- ZQKKUACPEQGYGK-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2N=C(C)N=C2)C(OC)=CC=1NC(=NN1CC=CC2)N=C1C2C1=CC=C(F)C=C1 ZQKKUACPEQGYGK-UHFFFAOYSA-N 0.000 claims 1
- STCJZEUXGBWJQB-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(3-methyl-1,2-oxazol-5-yl)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(C=2ON=C(C)C=2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 STCJZEUXGBWJQB-UHFFFAOYSA-N 0.000 claims 1
- XYQTVJRDVVTBMA-UHFFFAOYSA-N 9-(4-fluorophenyl)-n-[3-methoxy-4-(6-methylpyridazin-4-yl)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(C=2C=C(C)N=NC=2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 XYQTVJRDVVTBMA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- BKARWAKOJJOBEN-UHFFFAOYSA-N n-[3,5-difluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(trifluoromethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=C(F)C=C1NC1=NN2CCCCC(C=3C=CC(OC(F)(F)F)=CC=3)C2=N1 BKARWAKOJJOBEN-UHFFFAOYSA-N 0.000 claims 1
- UURWCDYFZCJXMM-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-8-[4-(trifluoromethoxy)phenyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCC(C=3C=CC(OC(F)(F)F)=CC=3)C2=N1 UURWCDYFZCJXMM-UHFFFAOYSA-N 0.000 claims 1
- XLEHDVGYNCEJBM-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9'-(4-fluorophenyl)spiro[1,3-dioxolane-2,7'-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepine]-2'-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCC3(OCCO3)CC(C=3C=CC(F)=CC=3)C2=N1 XLEHDVGYNCEJBM-UHFFFAOYSA-N 0.000 claims 1
- HGYRHOIVRTUKEJ-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(F)=CC=3)C2=N1 HGYRHOIVRTUKEJ-UHFFFAOYSA-N 0.000 claims 1
- SFDPVZCAJIGKPZ-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[3-fluoro-4-(trifluoromethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=C(F)C(OC(F)(F)F)=CC=3)C2=N1 SFDPVZCAJIGKPZ-UHFFFAOYSA-N 0.000 claims 1
- ZGEIPGMPHOCQIY-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(2,2,2-trifluoroethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(OCC(F)(F)F)=CC=3)C2=N1 ZGEIPGMPHOCQIY-UHFFFAOYSA-N 0.000 claims 1
- YVPHOYSDZMKDTF-UHFFFAOYSA-N n-[3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(trifluoromethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C(C)N=CN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(OC(F)(F)F)=CC=3)C2=N1 YVPHOYSDZMKDTF-UHFFFAOYSA-N 0.000 claims 1
- GXUIBEGWVDCQHE-UHFFFAOYSA-N n-[3-fluoro-4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound CC1=NC=NN1C(C(=C1)F)=CC=C1NC1=NN2CCCC(C=3C=CC(F)=CC=3)C2=N1 GXUIBEGWVDCQHE-UHFFFAOYSA-N 0.000 claims 1
- GOLUZQYFQAIUDQ-UHFFFAOYSA-N n-[3-fluoro-4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound CC1=NC=NN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(F)=CC=3)C2=N1 GOLUZQYFQAIUDQ-UHFFFAOYSA-N 0.000 claims 1
- CELZOCIYJRQKTQ-UHFFFAOYSA-N n-[3-fluoro-4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(2,2,2-trifluoroethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound CC1=NC=NN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(OCC(F)(F)F)=CC=3)C2=N1 CELZOCIYJRQKTQ-UHFFFAOYSA-N 0.000 claims 1
- DRNPZCODRJLFSL-UHFFFAOYSA-N n-[3-fluoro-4-(5-methyl-1,2,4-triazol-1-yl)phenyl]-9-[4-(trifluoromethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound CC1=NC=NN1C(C(=C1)F)=CC=C1NC1=NN2CCCCC(C=3C=CC(OC(F)(F)F)=CC=3)C2=N1 DRNPZCODRJLFSL-UHFFFAOYSA-N 0.000 claims 1
- YAQWHYPOTPCRJL-UHFFFAOYSA-N n-[4-(3-chloro-1,2,4-triazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(N2N=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 YAQWHYPOTPCRJL-UHFFFAOYSA-N 0.000 claims 1
- UMENVUFCZBXBCO-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3,5-difluorophenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C1=CC(F)=CC=C1C1C2=NC(NC=3C=C(F)C(=C(F)C=3)N3C=C(Cl)N=C3)=NN2CCCC1 UMENVUFCZBXBCO-UHFFFAOYSA-N 0.000 claims 1
- ZBNLMUKHPXNHBK-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-fluoro-5-methoxyphenyl]-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C(F)=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1 ZBNLMUKHPXNHBK-UHFFFAOYSA-N 0.000 claims 1
- KZTQUAAPLBAWCC-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-5-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN12)N=C1CCCC2C1=CC=C(F)C=C1 KZTQUAAPLBAWCC-UHFFFAOYSA-N 0.000 claims 1
- SOVYWPCYKYARCL-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-7-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN12)C=C1CCCC2C1=CC=C(F)C=C1 SOVYWPCYKYARCL-UHFFFAOYSA-N 0.000 claims 1
- ABWVFXNOLNNHGP-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-8-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCC2)N=C1C2C1=CC=C(Cl)C=C1Cl ABWVFXNOLNNHGP-UHFFFAOYSA-N 0.000 claims 1
- UXVWXZNCHOBILM-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCC2)N=C1C2C1=CC=C(F)C=C1 UXVWXZNCHOBILM-UHFFFAOYSA-N 0.000 claims 1
- KJBZXTBCUHHHKH-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9'-(4-fluorophenyl)spiro[1,3-dioxolane-2,7'-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepine]-2'-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC2)N=C1C(C=1C=CC(F)=CC=1)CC12OCCO1 KJBZXTBCUHHHKH-UHFFFAOYSA-N 0.000 claims 1
- KNHITGRUZFMVLF-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2,4-dichlorophenyl)-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC=CC2)N=C1C2C1=CC=C(Cl)C=C1Cl KNHITGRUZFMVLF-UHFFFAOYSA-N 0.000 claims 1
- XZEFJQNURDEUTP-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2,4-difluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C=C1F XZEFJQNURDEUTP-UHFFFAOYSA-N 0.000 claims 1
- UPLRVCGMDNCGNC-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(2-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=CC=C1F UPLRVCGMDNCGNC-UHFFFAOYSA-N 0.000 claims 1
- NNWXPNWHHIHASW-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3,4-difluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(F)C(F)=C1 NNWXPNWHHIHASW-UHFFFAOYSA-N 0.000 claims 1
- RZDMAGNGLOJORS-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3,5-difluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC(F)=CC(F)=C1 RZDMAGNGLOJORS-UHFFFAOYSA-N 0.000 claims 1
- XRRCVLNYATYOLT-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(3-fluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=CC(F)=C1 XRRCVLNYATYOLT-UHFFFAOYSA-N 0.000 claims 1
- QLTQICTXJWAYKD-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-chlorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(Cl)C=C1 QLTQICTXJWAYKD-UHFFFAOYSA-N 0.000 claims 1
- KUXYSUOPKJTPDG-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7,7-dimethoxy-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCC(C2)(OC)OC)N=C1C2C1=CC=C(F)C=C1 KUXYSUOPKJTPDG-UHFFFAOYSA-N 0.000 claims 1
- BDNLQDKQPAYYPW-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7-methoxyimino-5,6,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound N1=C2C(C=3C=CC(F)=CC=3)CC(=NOC)CCN2N=C1NC(C=C1OC)=CC=C1N1C=NC(Cl)=C1 BDNLQDKQPAYYPW-UHFFFAOYSA-N 0.000 claims 1
- ONGNMYCKZSZZML-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7-methyl-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCC(C)C2)N=C1C2C1=CC=C(F)C=C1 ONGNMYCKZSZZML-UHFFFAOYSA-N 0.000 claims 1
- QHSPIFWBCJOQCR-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-7-pyrrolidin-1-yl-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC2)N=C1C(C=1C=CC(F)=CC=1)CC2N1CCCC1 QHSPIFWBCJOQCR-UHFFFAOYSA-N 0.000 claims 1
- VTHAWVAAIFRQTO-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-(4-fluorophenyl)-8,9-dihydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CC=CC2)N=C1C2C1=CC=C(F)C=C1 VTHAWVAAIFRQTO-UHFFFAOYSA-N 0.000 claims 1
- MLWUDEMNFSULJH-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-[4-(2,2,2-trifluoroethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(OCC(F)(F)F)C=C1 MLWUDEMNFSULJH-UHFFFAOYSA-N 0.000 claims 1
- PGHQZMBEHPHQHE-UHFFFAOYSA-N n-[4-(4-chloroimidazol-1-yl)-3-methoxyphenyl]-9-[4-(2,2-difluoroethoxy)phenyl]-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepin-2-amine Chemical compound C=1C=C(N2C=C(Cl)N=C2)C(OC)=CC=1NC(=NN1CCCC2)N=C1C2C1=CC=C(OCC(F)F)C=C1 PGHQZMBEHPHQHE-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14531909P | 2009-01-16 | 2009-01-16 | |
| US61/145,319 | 2009-01-16 | ||
| PCT/US2010/020710 WO2010083141A1 (en) | 2009-01-16 | 2010-01-12 | Bicyclic compounds for the reduction of beta-amyloid production |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012515205A JP2012515205A (ja) | 2012-07-05 |
| JP2012515205A5 true JP2012515205A5 (https=) | 2013-01-17 |
| JP5638007B2 JP5638007B2 (ja) | 2014-12-10 |
Family
ID=42061022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011546297A Expired - Fee Related JP5638007B2 (ja) | 2009-01-16 | 2010-01-12 | ベータ−アミロイド産生の減少のための二環式化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8349880B2 (https=) |
| EP (1) | EP2379553B1 (https=) |
| JP (1) | JP5638007B2 (https=) |
| CN (1) | CN102356081B (https=) |
| AR (1) | AR075139A1 (https=) |
| ES (1) | ES2426023T3 (https=) |
| TW (1) | TW201030002A (https=) |
| WO (1) | WO2010083141A1 (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2742897A1 (en) | 2008-11-06 | 2010-05-14 | Astrazeneca Ab | Modulators of amyloid beta. |
| PA8854101A1 (es) | 2008-12-18 | 2010-07-27 | Ortho Mcneil Janssen Pharm | Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa |
| WO2010089292A1 (en) | 2009-02-06 | 2010-08-12 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc | Novel substituted bicyclic heterocyclic compounds as gamma secretase modulators |
| TWI461425B (zh) | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| AU2010262036B2 (en) | 2009-05-07 | 2014-10-30 | Cellzome Limited | Novel substituted indazole and aza-indazole derivatives as gamma secretase modulators |
| JP2012532912A (ja) | 2009-07-15 | 2012-12-20 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | ガンマセクレターゼモジュレーターとしての置換されたトリアゾールおよびイミダゾール誘導体 |
| BR112012017310A2 (pt) * | 2010-01-15 | 2016-04-19 | Janssen Pharmaceuticals Inc | derivados de triazol substituídos como moduladores de gama secretase |
| LT2603513T (lt) | 2010-08-10 | 2020-05-25 | Takeda Pharmaceutical Company Limited | Heterociklinis junginys ir jo panaudojimas kaip ampa receptoriaus teigiamo alosterinio moduliatoriaus |
| BR112013004746A2 (pt) | 2010-09-02 | 2016-06-07 | Takeda Pharmaceutical | "composto, medicamento, inibidor da produção de beta-amilóide, modulador de gama-secretase, métodos para inibir a produção de beta-amilóide, para modular gama-secretase, e para prevenir ou tratar deficiência cognitiva branda ou mal de alzheimer, e, uso do composto." |
| TW201309655A (zh) * | 2011-01-28 | 2013-03-01 | 必治妥美雅史谷比公司 | 降低β－類澱粉生成之化合物 |
| AU2012230348A1 (en) | 2011-03-24 | 2013-08-29 | Cellzome Limited | Novel substituted triazolyl piperazine and triazolyl piperidine derivatives as gamma secretase modulators |
| EP2691393B1 (en) | 2011-03-31 | 2016-09-14 | Pfizer Inc | Novel bicyclic pyridinones |
| KR101913135B1 (ko) | 2011-07-15 | 2018-10-30 | 얀센 파마슈티칼즈, 인코포레이티드 | 감마 세크레타제 조절 인자로서의 신규의 치환 인돌 유도체 |
| US9181245B2 (en) | 2012-05-16 | 2015-11-10 | Janssen Pharmaceuticals, Inc. | Substituted pyrido[1,2-a]pyrazines and substituted pyrido[1,2-a][1,4]diazepines for the treatment of (inter alia) Alzheimer's disease |
| EP2687528A1 (en) | 2012-07-17 | 2014-01-22 | Ares Trading S.A. | Fused triazole derivatives as gamma secretase modulators |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| CA2889249C (en) | 2012-12-20 | 2021-02-16 | Francois Paul Bischoff | Tricyclic 3,4-dihydro-2h-pyrido[1,2-a]pyrazine-1,6-dione derivatives as gamma secretase modulators |
| CA2891755C (en) | 2013-01-17 | 2021-10-26 | Janssen Pharmaceutica Nv | Substituted pyrido-piperazinone derivatives as gamma secretase modulators |
| EP2958918B1 (en) * | 2013-02-21 | 2016-12-07 | Boehringer Ingelheim International GmbH | Dihydropteridinones ii |
| WO2014195323A1 (en) | 2013-06-04 | 2014-12-11 | Acturum Life Science AB | Pyrimidine compounds and their use as gamma secretase modulators |
| JP6368776B2 (ja) | 2013-06-04 | 2018-08-01 | アクチュラム・ライフ・サイエンス・アクチエボラーグ | トリアゾール化合物およびガンマセクレターゼモジュレーターとしてのその使用 |
| JP6396438B2 (ja) | 2013-06-04 | 2018-09-26 | アクチュラム・ライフ・サイエンス・アクチエボラーグ | トリアゾール化合物およびガンマセクレターゼモジュレーターとしてのその使用 |
| 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 |
| MX368391B (es) | 2015-02-03 | 2019-09-30 | Pfizer | Ciclopropabenzofuranil-piridopirazindionas novedosas. |
| JP7012715B2 (ja) | 2016-06-27 | 2022-01-28 | エフ．ホフマン－ラ ロシュ アーゲー | γ－セクレターゼモジュレーターとしてのトリアゾロピリジン |
| AR109829A1 (es) * | 2016-09-29 | 2019-01-30 | Hoffmann La Roche | Derivados de piperidina puenteados |
| WO2018083050A1 (en) * | 2016-11-01 | 2018-05-11 | F. Hoffmann-La Roche Ag | Bicyclic heteroaryl derivatives |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| WO2019121434A1 (en) * | 2017-12-18 | 2019-06-27 | F. Hoffmann-La Roche Ag | Triazolo-azepine derivatives |
| CN111417636B (zh) * | 2018-01-22 | 2023-09-26 | 豪夫迈·罗氏有限公司 | 三唑并-氮杂䓬衍生物 |
| AU2020321955A1 (en) | 2019-07-30 | 2022-03-17 | Eikonizo Therapapeutics, Inc. | HDAC6 inhibitors and uses thereof |
| AU2020348675B2 (en) | 2019-09-16 | 2025-11-20 | Takeda Pharmaceutical Company Limited | Azole-fused pyridazin-3(2H)-one derivatives |
| EP4065581B1 (en) | 2019-11-29 | 2024-07-24 | F. Hoffmann-La Roche AG | Process for the preparation (9s)-2-bromo-9-(2,3,4-trifluorophenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[1,5-a]azepine |
| IL316201A (en) | 2022-04-08 | 2024-12-01 | Eikonizo Therapeutics Inc | Oxadiazole HDAC6 inhibitors and their uses |
| WO2024032584A1 (zh) * | 2022-08-08 | 2024-02-15 | 苏州必扬医药科技有限公司 | 一种蛋白酪氨酸激酶抑制剂及其医疗用途 |
| CN120324393B (zh) * | 2025-05-20 | 2025-11-04 | 广东海洋大学 | (2,4-二氯苯基)甲基硫基甲烷脒及其盐的用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR059955A1 (es) * | 2006-03-09 | 2008-05-14 | Eisai R&D Man Co Ltd | Compuestos policiclicos no peptidicos, medicamentos que los contienen, y usos para prevenir o tratar enfermedades causadas por la produccion de beta amiloide |
| AU2008248129B8 (en) * | 2007-05-07 | 2013-05-30 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
| EP2155740B1 (en) | 2007-05-11 | 2011-01-26 | F. Hoffmann-La Roche AG | Hetarylanilines as modulators for amyloid beta |
| US7935815B2 (en) * | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| ES2529648T3 (es) | 2007-08-31 | 2015-02-24 | Eisai R&D Management Co., Ltd. | Compuesto policíclico |
| ES2375919T3 (es) | 2008-01-11 | 2012-03-07 | F. Hoffmann-La Roche Ag | Moduladores de beta-amiloide. |
| MX2010008700A (es) | 2008-02-22 | 2010-08-30 | Hoffmann La Roche | Moduladores de beta-amiloide. |
-
2009
- 2009-12-31 TW TW098146451A patent/TW201030002A/zh unknown
-
2010
- 2010-01-07 US US12/683,791 patent/US8349880B2/en active Active
- 2010-01-12 CN CN201080012637.2A patent/CN102356081B/zh not_active Expired - Fee Related
- 2010-01-12 JP JP2011546297A patent/JP5638007B2/ja not_active Expired - Fee Related
- 2010-01-12 EP EP10700643.9A patent/EP2379553B1/en not_active Not-in-force
- 2010-01-12 WO PCT/US2010/020710 patent/WO2010083141A1/en not_active Ceased
- 2010-01-12 ES ES10700643T patent/ES2426023T3/es active Active
- 2010-01-15 AR ARP100100099A patent/AR075139A1/es not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012515205A5 (https=) | ||
| JP7129420B2 (ja) | Ｈｐｋ１阻害剤としてのイソキノリン | |
| JP7654071B2 (ja) | 複素環スピロ化合物及び使用方法 | |
| US20230174519A1 (en) | Inhibitors of Rho Associated Coiled-Coil Containing Protein Kinase | |
| RU2431635C2 (ru) | Соединения и композиции в качестве ингибиторов активности каннабиноидного рецептора 1 | |
| JP2022500402A5 (https=) | ||
| CN101671336B (zh) | 芳杂环并嘧啶衍生物和类似物及其制备方法和用途 | |
| JP6631616B2 (ja) | ＣＤＫ阻害剤としての２−アミノ−ピリド［２，３−ｄ］ピリミジン−７（８Ｈ）−オン誘導体及びその使用 | |
| KR102165113B1 (ko) | Ａ2ａ 길항제 성질을 갖는 헤테로비시클로-치환된-[1,2,4]트리아졸로[1,5-ｃ]퀴나졸린-5-아민 화합물 | |
| JP2013500975A5 (https=) | ||
| JP2025536259A (ja) | 三環式化合物及びその使用 | |
| US20210309663A1 (en) | Compounds and compositions for inhbiting the activity of shp2 | |
| RU2016111675A (ru) | Соединения биарилацетамида и способы их применения | |
| JP2023549055A (ja) | 複素環式スピロ化合物及びその使用方法 | |
| JP2019535664A5 (https=) | ||
| RU2018138471A (ru) | Гетероциклические соединения в качестве ингибиторов киназы RET | |
| JP2007523183A5 (https=) | ||
| JP2013529611A5 (https=) | ||
| JP2014513139A5 (https=) | ||
| CN105294683A (zh) | Cdk类小分子抑制剂的化合物及其用途 | |
| JP2022502490A5 (https=) | ||
| NZ586579A (en) | Fused heterocyclic derivatives and methods of use as c-met inhibitors | |
| RU2015148189A (ru) | ПРОИЗВОДНЫЕ 2-АМИДОПИРИДО[4, 3-d]ПИРИМИДИН-5-ОНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ WEE-1 | |
| RU2012136907A (ru) | Модуляторы гамма-секретазы | |
| TW200538128A (en) | Therapeutic combinations of atypical antipsychotics with corticotropin releasing factor antagonists |