JP2006524206A5 - - Google Patents
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- Publication number
- JP2006524206A5 JP2006524206A5 JP2006505223A JP2006505223A JP2006524206A5 JP 2006524206 A5 JP2006524206 A5 JP 2006524206A5 JP 2006505223 A JP2006505223 A JP 2006505223A JP 2006505223 A JP2006505223 A JP 2006505223A JP 2006524206 A5 JP2006524206 A5 JP 2006524206A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- propyl
- ethyl
- dioxide
- indole
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 39
- -1 cyano, hydroxy, carboxy Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 2
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 230000006933 amyloid-beta aggregation Effects 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- BRNRSUUDAXVKFY-JTHBVZDNSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-(2,2,2-trifluoroethylamino)butan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC(F)(F)F)C1=CC=CC=C1 BRNRSUUDAXVKFY-JTHBVZDNSA-N 0.000 claims 1
- FFOYVHXUAYQKKC-UKILVPOCSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-(propan-2-ylamino)butan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNC(C)C)C1=CC=CC=C1 FFOYVHXUAYQKKC-UKILVPOCSA-N 0.000 claims 1
- KZSWFBYGEHXBKH-XTEPFMGCSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-(pyridin-2-ylmethylamino)butan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1N=CC=CC=1)C1=CC=CC=C1 KZSWFBYGEHXBKH-XTEPFMGCSA-N 0.000 claims 1
- RFDDXKUWIRIUMP-XTEPFMGCSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-(pyridin-4-ylmethylamino)butan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=CN=CC=1)C1=CC=CC=C1 RFDDXKUWIRIUMP-XTEPFMGCSA-N 0.000 claims 1
- FYFXGPATXSURAK-XDFJSJKPSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-(quinolin-3-ylmethylamino)butan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C2C=CC=CC2=NC=1)C1=CC=CC=C1 FYFXGPATXSURAK-XDFJSJKPSA-N 0.000 claims 1
- OJCGTUUAJINADL-CQTOTRCISA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-[(6-pyridin-2-ylpyridin-2-yl)methylamino]butan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1N=C(C=CC=1)C=1N=CC=CC=1)C1=CC=CC=C1 OJCGTUUAJINADL-CQTOTRCISA-N 0.000 claims 1
- CEBSXXKIZOJMCZ-MFMCTBQISA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-[2-[3-(trifluoromethyl)phenyl]propan-2-ylamino]butan-2-yl]-9-methyl-10-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)SCCN3C=C(C(C=1)=C32)CC)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 CEBSXXKIZOJMCZ-MFMCTBQISA-N 0.000 claims 1
- RYDQNNZIERLVEQ-BBVCVYGMSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-9,11-dimethyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)C(C)N3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 RYDQNNZIERLVEQ-BBVCVYGMSA-N 0.000 claims 1
- FDBMWJPRLCCERS-XTEPFMGCSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 FDBMWJPRLCCERS-XTEPFMGCSA-N 0.000 claims 1
- LUOVVGBKHGGZOU-LMSSTIIKSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-4-[(3-methoxyphenyl)methylamino]-1-phenylbutan-2-yl]-10-oxo-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2NC(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 LUOVVGBKHGGZOU-LMSSTIIKSA-N 0.000 claims 1
- DHMUWFLOJWNFRP-XTEPFMGCSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-4-[(5-methylpyrazin-2-yl)methylamino]-1-phenylbutan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1N=CC(C)=NC=1)C1=CC=CC=C1 DHMUWFLOJWNFRP-XTEPFMGCSA-N 0.000 claims 1
- FABRCIKGOOMRBB-LMSSTIIKSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-4-[(6-methylpyridin-2-yl)methylamino]-1-phenylbutan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1N=C(C)C=CC=1)C1=CC=CC=C1 FABRCIKGOOMRBB-LMSSTIIKSA-N 0.000 claims 1
- KIAJFELWEMLUBU-LMSSTIIKSA-N 3-ethyl-N-[(2S,3R)-3-hydroxy-4-[[5-(methylcarbamoyl)pyridin-3-yl]methylamino]-1-phenylbutan-2-yl]-9-methyl-10-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)SCCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C(C=NC=1)C(=O)NC)C1=CC=CC=C1 KIAJFELWEMLUBU-LMSSTIIKSA-N 0.000 claims 1
- SNTCTRGDVFKQPC-AHKZPQOWSA-N 3-ethyl-N-[(2S,3R)-4-[(1-ethylpyrazol-4-yl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC1=CN(CC)N=C1)C1=CC=CC=C1 SNTCTRGDVFKQPC-AHKZPQOWSA-N 0.000 claims 1
- KZBAKEHPWOCZMR-XTEPFMGCSA-N 3-ethyl-N-[(2S,3R)-4-[(1-ethylpyrazol-4-yl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC1=CN(CC)N=C1)C1=CC=CC=C1 KZBAKEHPWOCZMR-XTEPFMGCSA-N 0.000 claims 1
- WLNRSNILOZRUHQ-XTEPFMGCSA-N 3-ethyl-N-[(2S,3R)-4-[(3-ethyl-1,2-oxazol-5-yl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound O1N=C(CC)C=C1CNC[C@@H](O)[C@@H](NC(=O)C=1C=C2C(CC)=CN3CCS(=O)(=O)N(C)C(=C23)C=1)CC1=CC=CC=C1 WLNRSNILOZRUHQ-XTEPFMGCSA-N 0.000 claims 1
- RIJZIPUXTWWJJL-LMSSTIIKSA-N 3-ethyl-N-[(2S,3R)-4-[(5-ethylthiophen-3-yl)methylamino]-3-hydroxy-1-phenylbutan-2-yl]-9-methyl-10,10-dioxo-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound S1C(CC)=CC(CNC[C@@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C3C(CC)=CN4CCS(=O)(=O)N(C)C(=C34)C=2)=C1 RIJZIPUXTWWJJL-LMSSTIIKSA-N 0.000 claims 1
- BIFXFADRRVXKMW-LMSSTIIKSA-N 6,6,5 tricyclic sulfonamide, 21 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 BIFXFADRRVXKMW-LMSSTIIKSA-N 0.000 claims 1
- GPAVTBALSLYNRZ-LMSSTIIKSA-N 6,6,5 tricyclic sulfonamide, 23 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 GPAVTBALSLYNRZ-LMSSTIIKSA-N 0.000 claims 1
- MNGUVHPNHVMEDL-MFMCTBQISA-N 7,6,5 tricyclic sulfonamide, 22 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 MNGUVHPNHVMEDL-MFMCTBQISA-N 0.000 claims 1
- WPHAMDWBDNXCBJ-LMSSTIIKSA-N 7,6,5 tricyclic sulfonamide, 34 Chemical compound C([C@H](NC(=O)C=1C=C2NS(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=C(OC)C=CC=1)C1=CC=CC=C1 WPHAMDWBDNXCBJ-LMSSTIIKSA-N 0.000 claims 1
- VHIKANGIVZQCPI-XTEPFMGCSA-N 7,6,5 tricyclic sulfonamide, 35 Chemical compound C([C@H](NC(=O)C=1C=C2N(S(CCN3C=C(CC)C(=C23)C=1)(=O)=O)CC)[C@H](O)CNC1CCOCC1)C1=CC=CC=C1 VHIKANGIVZQCPI-XTEPFMGCSA-N 0.000 claims 1
- BKJAHVKDVOINBT-LMSSTIIKSA-N 7,6,5 tricyclic sulfonamide, 36 Chemical compound C([C@H](NC(=O)C=1C=C2N(C(C)C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNC1CCOCC1)C1=CC=CC=C1 BKJAHVKDVOINBT-LMSSTIIKSA-N 0.000 claims 1
- XBSGWVTXAJRWKB-LMSSTIIKSA-N 7,6,5 tricyclic sulfonamide, 38 Chemical compound C([C@H](NC(=O)C=1C=C2N(S(CCN3C=C(CC)C(=C23)C=1)(=O)=O)CC)[C@H](O)CNC1CCCCC1)C1=CC=CC=C1 XBSGWVTXAJRWKB-LMSSTIIKSA-N 0.000 claims 1
- IBCUBWFCCFTHOX-IGYGKHONSA-N 9-ethyl-N-[(2S,3R)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-10,10-dioxo-3-propyl-10lambda6-thia-1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2N(CC)S(=O)(=O)CCN3C=C(C(C=1)=C32)CCC)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 IBCUBWFCCFTHOX-IGYGKHONSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- FYACSYJEEVPJRT-AHKZPQOWSA-N C([C@H](NC(=O)C1=CC2=C3N(C(S(=O)(=O)N2C)(C)C)C=C(C3=C1)CC)[C@H](O)CNC1CCOCC1)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C1=CC2=C3N(C(S(=O)(=O)N2C)(C)C)C=C(C3=C1)CC)[C@H](O)CNC1CCOCC1)C1=CC=CC=C1 FYACSYJEEVPJRT-AHKZPQOWSA-N 0.000 claims 1
- AFMRBRUYHBVKCH-JFVQPPLISA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)C(C)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)C(C)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNC(C)(C)CCCC(C)C)C1=CC=CC=C1 AFMRBRUYHBVKCH-JFVQPPLISA-N 0.000 claims 1
- NVTKGNKFONWMJJ-PJGYDLQESA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)C(C)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC1=CN(CC)N=C1)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)C(C)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC1=CN(CC)N=C1)C1=CC=CC=C1 NVTKGNKFONWMJJ-PJGYDLQESA-N 0.000 claims 1
- OENNVAYYRUALCN-JTHBVZDNSA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNC)C1=CC=CC(Cl)=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNC)C1=CC=CC(Cl)=C1 OENNVAYYRUALCN-JTHBVZDNSA-N 0.000 claims 1
- POXZPNDRDGMUOM-JTHBVZDNSA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC(F)(F)C(F)(F)F)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC(F)(F)C(F)(F)F)C1=CC=CC=C1 POXZPNDRDGMUOM-JTHBVZDNSA-N 0.000 claims 1
- NPLLWQSCEDKDLI-XTEPFMGCSA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=NC=CC=1)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCC=1C=NC=CC=1)C1=CC=CC=C1 NPLLWQSCEDKDLI-XTEPFMGCSA-N 0.000 claims 1
- WJPFSIOHUCRTFZ-MFMCTBQISA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCCC=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CNCCC=1C=CC=CC=1)C1=CC=CC=C1 WJPFSIOHUCRTFZ-MFMCTBQISA-N 0.000 claims 1
- UGPLNYIRISZEBD-GSBZAIBZSA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CN[C@@H]1C2=CC=CC=C2CC1)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CCN3C=C(C(C=1)=C32)CC)[C@H](O)CN[C@@H]1C2=CC=CC=C2CC1)C1=CC=CC=C1 UGPLNYIRISZEBD-GSBZAIBZSA-N 0.000 claims 1
- RUAWEOGDECXJLX-LMSSTIIKSA-N C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 Chemical compound C([C@H](NC(=O)C=1C=C2N(C)S(=O)(=O)CN3C=C(C(C=1)=C32)CC)[C@H](O)CNC(C)(C)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 RUAWEOGDECXJLX-LMSSTIIKSA-N 0.000 claims 1
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| PE20040762A1 (es) * | 2002-11-27 | 2004-11-06 | Elan Pharm Inc | Ureas substituidas y carbamatos utiles para el tratamiento de la enfermedad de alzheimer |
| GB0328900D0 (en) * | 2003-12-12 | 2004-01-14 | Glaxo Group Ltd | Novel compounds |
| US7763609B2 (en) | 2003-12-15 | 2010-07-27 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| GB0411404D0 (en) * | 2004-05-21 | 2004-06-23 | Glaxo Group Ltd | Novel compounds |
| BRPI0515383A (pt) * | 2004-09-21 | 2008-07-22 | Pfizer Prod Inc | n-etil hidroxietilamina útil no tratamento de condições do snc |
| GB0422765D0 (en) * | 2004-10-13 | 2004-11-17 | Glaxo Group Ltd | Novel compounds |
| GB0422755D0 (en) * | 2004-10-13 | 2004-11-17 | Glaxo Group Ltd | Novel compounds |
| GB0422766D0 (en) * | 2004-10-13 | 2004-11-17 | Glaxo Group Ltd | Novel compounds |
| WO2006088705A1 (en) * | 2005-02-14 | 2006-08-24 | Wyeth | Terphenyl guanidines as [beta symbol] -secretase inhibitors |
| GB0506562D0 (en) * | 2005-03-31 | 2005-05-04 | Glaxo Group Ltd | Novel compounds |
| MX2007012341A (es) | 2005-04-08 | 2008-02-12 | Comentis Inc | Compuestos que inhiben actividad beta-secretasa y metodos de uso de los mismos. |
| WO2007019078A2 (en) * | 2005-08-03 | 2007-02-15 | Merck & Co., Inc. | Tricyclic beta-secretase inhibitors for the treatment of alzheimer's disease |
| US7838676B2 (en) * | 2005-11-21 | 2010-11-23 | Amgen Inc. | Beta-secretase modulators and methods of use |
| US7872009B2 (en) * | 2005-11-21 | 2011-01-18 | Amgen Inc. | Beta-Secretase modulators and methods of use |
| EP1971598A1 (en) * | 2005-11-21 | 2008-09-24 | Amgen Inc. | Beta-secretase modulators and methods of use |
| US7745484B2 (en) | 2005-11-21 | 2010-06-29 | Amgen Inc. | Beta-secretase modulators and methods of use |
| CA2687608C (en) | 2007-05-25 | 2013-07-02 | Amgen Inc. | Substituted hydroxyethyl amine compounds as beta-secretase modulators and methods of use |
| CL2008001500A1 (es) | 2007-05-25 | 2008-12-26 | Amgen Inc | Compuestos derivados de hidroxietil amina sustituidas, moduladores de betasecretasa; proceso de preparacion de dichos c ompuestos; composicion farmaceutica que los comprende; y su uso para tratar un trastorno neurologico, tal como alzheimer, sindrome de down, demencia degenerativa, entre otros. |
| FR2919288B1 (fr) * | 2007-07-27 | 2009-09-04 | Sanofi Aventis Sa | Derives de 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-6- carboxamides, leur preparation et leur application en therapeutique. |
| FR2919285B1 (fr) | 2007-07-27 | 2012-08-31 | Sanofi Aventis | Derives de 1-oxo-isoindoline-4-carboxamides et de 1-oxo- 1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur preparation et leur application en therapeutique. |
| KR20100050485A (ko) * | 2007-07-27 | 2010-05-13 | 사노피-아벤티스 | 1,2,3,4-테트라히드로피롤로[1,2-ａ]피라진-6-카르복스아미드 및 2,3,4,5-테트라히드로피롤로[1,2-ａ][1,4]-디아제핀-7-카르복스아미드 유도체, 그의 제조 및 치료적 용도 |
| FR2919286A1 (fr) | 2007-07-27 | 2009-01-30 | Sanofi Aventis Sa | Derives de derives de 1-oxo-1,2-dihydroisoquinoleine-5- carboxamides et de 4-oxo-3,4-dihydroquinazoline-8- carboxamides,leur preparation et leur application en therapeutique. |
| FR2919289B1 (fr) * | 2007-07-27 | 2009-09-04 | Sanofi Aventis Sa | Derives de 2,3,4,5-tetrahydropyrrolo[1,2-a][1,4]- diazepine-7-carboxamides, leur preparation et leur application en therapeutique. |
| WO2013148130A1 (en) * | 2012-03-29 | 2013-10-03 | Oklahoma Medical Research Foundation | Inhibition of memapsin 1 cleavage in the treatment of diabetes |
| RU2764243C2 (ru) * | 2017-09-22 | 2022-01-14 | ДЖУБИЛАНТ ЭПИПЭД ЭлЭлСи | Гетероциклические соединения в качестве ингибиторов PAD |
| WO2019075358A1 (en) * | 2017-10-13 | 2019-04-18 | Ghosh Arun K | BACE1 INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| US12043631B2 (en) | 2017-10-13 | 2024-07-23 | Purdue Research Foundation | BACE1 inhibitors for the treatment of Alzheimer's disease |
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| WO1998033795A1 (en) * | 1997-02-04 | 1998-08-06 | The Regents Of The University Of California | Nanomolar, non-peptide inhibitors of cathepsin d |
| US6207664B1 (en) * | 1998-11-25 | 2001-03-27 | Pfizer Inc. | Squalene synthetase inhibitor agents |
| CA2410680A1 (en) * | 2000-06-30 | 2002-01-10 | Elan Pharmaceuticals, Inc. | Compounds to treat alzheimer's disease |
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2003
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2004
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- 2004-04-21 WO PCT/EP2004/004244 patent/WO2004094430A1/en not_active Ceased
- 2004-04-21 KR KR1020057019979A patent/KR20050111797A/ko not_active Withdrawn
- 2004-04-21 JP JP2006505223A patent/JP2006524206A/ja not_active Withdrawn
- 2004-04-21 CA CA002523291A patent/CA2523291A1/en not_active Abandoned
- 2004-04-21 US US10/553,878 patent/US20060229302A1/en not_active Abandoned
- 2004-04-21 BR BRPI0409622-3A patent/BRPI0409622A/pt not_active IP Right Cessation
- 2004-04-21 CN CNA2004800175617A patent/CN1809573A/zh active Pending
- 2004-04-21 MX MXPA05011365A patent/MXPA05011365A/es not_active Application Discontinuation
- 2004-04-21 EP EP04728567A patent/EP1620438A1/en not_active Withdrawn
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2005
- 2005-10-05 ZA ZA200508041A patent/ZA200508041B/en unknown
- 2005-10-19 MA MA28563A patent/MA27674A1/fr unknown
- 2005-10-21 CO CO05107375A patent/CO5700829A2/es not_active Application Discontinuation
- 2005-11-17 NO NO20055442A patent/NO20055442L/no not_active Application Discontinuation
- 2005-11-21 IS IS8135A patent/IS8135A/is unknown