JP2012515205A5 - - Google Patents
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- 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
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- -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
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
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- 239000003085 diluting agent Substances 0.000 claims 1
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- 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
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| KR20110082189A (ko) | 2008-11-06 | 2011-07-18 | 아스트라제네카 아베 | 아밀로이드 베타의 조절제 |
| PA8854101A1 (es) | 2008-12-18 | 2010-07-27 | Ortho Mcneil Janssen Pharm | Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa |
| NZ593951A (en) | 2009-02-06 | 2013-01-25 | Ortho Mcneil Janssen Pharm | 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 |
| KR20120024555A (ko) | 2009-05-07 | 2012-03-14 | 얀센 파마슈티칼즈, 인코포레이티드 | 감마 세크레타제 조절제로서의 신규 치환된 인다졸 및 아자-인다졸 유도체 |
| US8946266B2 (en) | 2009-07-15 | 2015-02-03 | Janssen Pharmaceuticals, Inc. | Substituted triazole and imidazole derivatives as gamma secretase modulators |
| EP2523949B1 (en) | 2010-01-15 | 2014-08-20 | Janssen Pharmaceuticals Inc. | Novel substituted triazole derivatives as gamma secretase modulators |
| KR101852215B1 (ko) | 2010-08-10 | 2018-04-25 | 다케다 야쿠힌 고교 가부시키가이샤 | 헤테로시클릭 화합물 및 이의 용도 |
| MX2013002511A (es) * | 2010-09-02 | 2013-07-29 | Takeda Pharmaceutical | Triazoles fusionados para el tratamiento o profilaxis de daño cognitivo moderado. |
| 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 |
| JP2014508794A (ja) | 2011-03-24 | 2014-04-10 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | γ−セクレターゼ調節剤としての新規な置換トリアゾリルピペラジンおよびトリアゾリルピペラジン誘導体 |
| ES2602794T3 (es) | 2011-03-31 | 2017-02-22 | Pfizer Inc | Piridinonas bicíclicas novedosas |
| CN103874702B (zh) | 2011-07-15 | 2015-12-09 | 杨森制药公司 | 作为γ分泌酶调节剂的经取代的吲哚衍生物 |
| ES2585009T3 (es) | 2012-05-16 | 2016-10-03 | Janssen Pharmaceuticals, Inc. | Derivados de 3,4-dihidro-2H-pirido[1,2-a]pirazina-1,6-diona sustituidos útiles para el tratamiento de (inter alia) enfermedad de Alzheimer |
| 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 |
| JP6275161B2 (ja) | 2012-12-20 | 2018-02-07 | ヤンセン ファーマシューティカ エヌ．ベー． | γセクレターゼ調節剤としての新規な三環式３，４−ジヒドロ−２Ｈ−ピリド［１，２−ａ］ピラジン−１，６−ジオン誘導体 |
| WO2014111457A1 (en) | 2013-01-17 | 2014-07-24 | Janssen Pharmaceutica Nv | Novel substituted pyrido-piperazinone derivatives as gamma secretase modulators |
| JP6072308B2 (ja) * | 2013-02-21 | 2017-02-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ジヒドロプテリジノンｉｉ |
| EP3004081B1 (en) | 2013-06-04 | 2017-11-15 | Acturum Real Estate AB | Triazole compounds and their use as gamma secretase modulators |
| JP6368777B2 (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 | ピリミジン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 |
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| 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 |
| WO2016125048A1 (en) | 2015-02-03 | 2016-08-11 | Pfizer Inc. | Novel cyclopropabenzofuranyl pyridopyrazinediones |
| 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 |
| AR110001A1 (es) * | 2016-11-01 | 2019-02-13 | Hoffmann La Roche | Derivados heteroarilo bicíclicos |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| JP7248671B2 (ja) * | 2017-12-18 | 2023-03-29 | エフ． ホフマン－ラ ロシュ アーゲー | トリアゾロ－アゼピン誘導体 |
| EP3743428B1 (en) * | 2018-01-22 | 2022-01-19 | F. Hoffmann-La Roche AG | Triazolo-azepine derivatives |
| KR20220063228A (ko) | 2019-09-16 | 2022-05-17 | 다케다 야쿠힌 고교 가부시키가이샤 | 아졸-융합된 피리다진-3(2h)-온 유도체 |
| WO2021105337A1 (en) | 2019-11-29 | 2021-06-03 | 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 |
| JP2025528048A (ja) * | 2022-08-08 | 2025-08-26 | 蘇州必揚医薬科技有限公司 | プロテインチロシンキナーゼ阻害剤およびその医療上の使用 |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2643796A1 (en) * | 2006-03-09 | 2007-09-13 | Eisai R & D Management Co., Ltd. | Polycyclic cinnamide derivatives |
| AU2008248129B8 (en) * | 2007-05-07 | 2013-05-30 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
| AU2008250436B2 (en) | 2007-05-11 | 2013-03-28 | 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 |
| KR20100055456A (ko) | 2007-08-31 | 2010-05-26 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 다환식 화합물 |
| CA2703824C (en) | 2008-01-11 | 2016-06-07 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| 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
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2010
- 2010-01-07 US US12/683,791 patent/US8349880B2/en active Active
- 2010-01-12 ES ES10700643T patent/ES2426023T3/es active Active
- 2010-01-12 WO PCT/US2010/020710 patent/WO2010083141A1/en not_active Ceased
- 2010-01-12 CN CN201080012637.2A patent/CN102356081B/zh not_active Expired - Fee Related
- 2010-01-12 EP EP10700643.9A patent/EP2379553B1/en not_active Not-in-force
- 2010-01-12 JP JP2011546297A patent/JP5638007B2/ja not_active Expired - Fee Related
- 2010-01-15 AR ARP100100099A patent/AR075139A1/es not_active Application Discontinuation
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