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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| CN102325765B (zh) | 2009-02-06 | 2014-12-24 | 杨森制药公司 | 作为γ-分泌酶调节剂的取代的双环杂环化合物 |
| 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 |
| CA2755467A1 (en) | 2009-05-07 | 2010-12-23 | Janssen Pharmaceuticals, Inc. | Novel substituted indazole and aza-indazole derivatives as gamma secretase modulators |
| BR112012000915A2 (pt) | 2009-07-15 | 2019-09-24 | Janssen Pharmaceuticals Inc | derivados de triazol e imidazol substituídos como moduladores de gama secretase. |
| AU2011206635B2 (en) | 2010-01-15 | 2015-01-22 | Cellzome Limited | Novel substituted triazole derivatives as gamma secretase modulators |
| SI2603513T1 (sl) | 2010-08-10 | 2020-07-31 | Takeda Pharmaceutical Company Limited | Heterociklična spojina in njena uporaba kot pozitivni alosterični modulator receptorja AMPA |
| EP2611805A1 (en) | 2010-09-02 | 2013-07-10 | Takeda Pharmaceutical Company Limited | Fused triazoles for the treatment or prophylaxis of mild cognitive impairment |
| 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 |
| WO2012131539A1 (en) | 2011-03-31 | 2012-10-04 | Pfizer Inc. | Novel bicyclic pyridinones |
| ES2555167T3 (es) | 2011-07-15 | 2015-12-29 | Janssen Pharmaceuticals, Inc. | Nuevos derivados de indol sustituidos como moduladores de gamma secretasa |
| CN104583208B (zh) | 2012-05-16 | 2016-09-28 | 杨森制药公司 | 可用于治疗(尤其是)阿尔茨海默病的取代的3,4-二氢-2H-吡啶并[1,2-a]吡嗪-1,6-二酮衍生物 |
| 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 |
| AU2013366668B2 (en) | 2012-12-20 | 2017-07-20 | Janssen Pharmaceutica Nv | Novel tricyclic 3,4-dihydro-2H-pyrido[1,2-alpha]pyrazine -1,6-dione derivatives as gamma secretase modulators |
| AU2014206834B2 (en) | 2013-01-17 | 2017-06-22 | Janssen Pharmaceutica Nv | Novel substituted pyrido-piperazinone derivatives as gamma secretase modulators |
| WO2014127816A1 (en) * | 2013-02-21 | 2014-08-28 | 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 |
| US9611254B2 (en) | 2013-06-04 | 2017-04-04 | Acturum Life Science AB | Triazole compounds and their use as gamma secretase modulators |
| DK3004080T3 (da) | 2013-06-04 | 2019-01-02 | Acturum Real Estate Ab | Triazolforbindelser og deres anvendelse som gamma-sekretase-modulatorer |
| 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 |
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| 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 |
| WO2021021979A2 (en) | 2019-07-30 | 2021-02-04 | Eikonizo Therapapeutics, Inc. | Hdac6 inhibitors and uses thereof |
| PL4031552T3 (pl) | 2019-09-16 | 2025-03-17 | Takeda Pharmaceutical Company Limited | Pochodne azolowo-skondensowanych pirydazyn-3(2h)-onów |
| 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 |
| EP4504190A4 (en) | 2022-04-08 | 2026-03-25 | Eikonizo Therapeutics Inc | OXADIAZOLE HDAC6 INHIBITORS AND THEIR USES |
| CN119604488A (zh) * | 2022-08-08 | 2025-03-11 | 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 |
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| PL1992618T3 (pl) | 2006-03-09 | 2012-06-29 | Eisai R&D Man Co Ltd | Policykliczna pochodna cynamidowa |
| CA2686589A1 (en) * | 2007-05-07 | 2008-11-13 | Schering Corporation | Gamma secretase modulators |
| AU2008250436B2 (en) | 2007-05-11 | 2013-03-28 | F. Hoffmann-La Roche Ag | Hetarylanilines as modulators for amyloid beta |
| ES2529648T3 (es) | 2007-08-31 | 2015-02-24 | Eisai R&D Management Co., Ltd. | Compuesto policíclico |
| US7935815B2 (en) | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| KR101244517B1 (ko) | 2008-01-11 | 2013-03-18 | 에프. 호프만-라 로슈 아게 | 아밀로이드 베타에 대한 조절제 |
| AU2009216851B2 (en) | 2008-02-22 | 2013-11-07 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
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- 2010-01-12 JP JP2011546297A patent/JP5638007B2/ja not_active Expired - Fee Related
- 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
- 2010-01-15 AR ARP100100099A patent/AR075139A1/es not_active Application Discontinuation
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