JP2013516395A5 - - Google Patents
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- JP2013516395A5 JP2013516395A5 JP2012546418A JP2012546418A JP2013516395A5 JP 2013516395 A5 JP2013516395 A5 JP 2013516395A5 JP 2012546418 A JP2012546418 A JP 2012546418A JP 2012546418 A JP2012546418 A JP 2012546418A JP 2013516395 A5 JP2013516395 A5 JP 2013516395A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- alkylthio
- halogen
- group
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 328
- 125000004414 alkyl thio group Chemical group 0.000 claims description 206
- 125000003545 alkoxy group Chemical group 0.000 claims description 182
- 229910052736 halogen Inorganic materials 0.000 claims description 80
- 150000002367 halogens Chemical class 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 41
- -1 cyano, amino, aminocarbonyl Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- GBXWORVXRWWDTA-UHFFFAOYSA-N 2,2-dichloroethyl 5-amino-3-[5-[(5-bromo-3-methylpyridine-2-carbonyl)amino]-2-fluorophenyl]-3-(difluoromethyl)-2,6-dihydropyrazine-1-carboxylate Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C(C2(N=C(N)CN(C2)C(=O)OCC(Cl)Cl)C(F)F)=C1 GBXWORVXRWWDTA-UHFFFAOYSA-N 0.000 claims 1
- NWYKTGFANHHXBN-UHFFFAOYSA-N 2-amino-n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1h-pyrazin-3-yl]-4-fluorophenyl]-6-oxo-1h-pyrazine-3-carboxamide Chemical compound C1NCC(N)=NC1(C(F)F)C1=CC(NC(=O)C2=C(NC(=O)C=N2)N)=CC=C1F NWYKTGFANHHXBN-UHFFFAOYSA-N 0.000 claims 1
- ZKNMXFGYYJETSC-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1h-pyrazin-3-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound NC1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C(C2(N=C(N)CNC2)C(F)F)=C1 ZKNMXFGYYJETSC-UHFFFAOYSA-N 0.000 claims 1
- GSOCTKHBFREQCV-UHFFFAOYSA-N 5-bromo-3-methylpyridine-2-carboxylic acid Chemical compound CC1=CC(Br)=CN=C1C(O)=O GSOCTKHBFREQCV-UHFFFAOYSA-N 0.000 claims 1
- HRLVPHGCEGTVLK-UHFFFAOYSA-N 5-cyanopyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C#N)C=N1 HRLVPHGCEGTVLK-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- FGPUURAPBZPKJF-UHFFFAOYSA-N n-[3-(3-amino-1,5-dimethyl-6-oxo-2h-pyrazin-5-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound O=C1N(C)CC(N)=NC1(C)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F FGPUURAPBZPKJF-UHFFFAOYSA-N 0.000 claims 1
- HJOOOXDRGOESCS-UHFFFAOYSA-N n-[3-(3-amino-1,5-dimethyl-6-oxo-2h-pyrazin-5-yl)phenyl]-5-bromopyridine-2-carboxamide Chemical compound O=C1N(C)CC(N)=NC1(C)C1=CC=CC(NC(=O)C=2N=CC(Br)=CC=2)=C1 HJOOOXDRGOESCS-UHFFFAOYSA-N 0.000 claims 1
- KDEOLGIEXQPNFC-UHFFFAOYSA-N n-[3-(3-amino-2-ethyl-1,5-dimethyl-6-oxo-2h-pyrazin-5-yl)phenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)C(CC)N(C)C(=O)C1(C)C1=CC=CC(NC(=O)C=2N=CC(Br)=CC=2)=C1 KDEOLGIEXQPNFC-UHFFFAOYSA-N 0.000 claims 1
- FOLNCKZOMNIALC-UHFFFAOYSA-N n-[3-(5-amino-1,3-dimethyl-2,6-dihydropyrazin-3-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1N(C)CC(N)=NC1(C)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F FOLNCKZOMNIALC-UHFFFAOYSA-N 0.000 claims 1
- VYTHRSNJIFMUBH-UHFFFAOYSA-N n-[3-(5-amino-1,3-dimethyl-6-oxo-2h-pyrazin-3-yl)-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(C)CC1(C)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)Cl)=CC=C1F VYTHRSNJIFMUBH-UHFFFAOYSA-N 0.000 claims 1
- VGTILVOMEOFBMU-UHFFFAOYSA-N n-[3-(5-amino-1,3-dimethyl-6-oxo-2h-pyrazin-3-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(C)CC1(C)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F VGTILVOMEOFBMU-UHFFFAOYSA-N 0.000 claims 1
- IBPGEEKFYIPLRV-UHFFFAOYSA-N n-[3-(5-amino-1,3-dimethyl-6-oxo-2h-pyrazin-3-yl)-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(C)CC1(C)C1=CC(NC(=O)C=2N=CC(Cl)=CC=2)=CC=C1F IBPGEEKFYIPLRV-UHFFFAOYSA-N 0.000 claims 1
- GMUSGOAHDMSZNC-UHFFFAOYSA-N n-[3-(5-amino-1-ethyl-3-methyl-6-oxo-2h-pyrazin-3-yl)-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(CC)CC1(C)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)Cl)=CC=C1F GMUSGOAHDMSZNC-UHFFFAOYSA-N 0.000 claims 1
- NNONTILIEPOHQT-UHFFFAOYSA-N n-[3-(5-amino-1-ethyl-3-methyl-6-oxo-2h-pyrazin-3-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(CC)CC1(C)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F NNONTILIEPOHQT-UHFFFAOYSA-N 0.000 claims 1
- WFPDPMQFKZCRFF-UHFFFAOYSA-N n-[3-(5-amino-1-ethyl-3-methyl-6-oxo-2h-pyrazin-3-yl)-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(CC)CC1(C)C1=CC(NC(=O)C=2N=CC(=CC=2)C#N)=CC=C1F WFPDPMQFKZCRFF-UHFFFAOYSA-N 0.000 claims 1
- IPEYSDUMVODEGM-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-6-oxo-1-propan-2-yl-2h-pyrazin-3-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(C(C)C)CC1(C)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F IPEYSDUMVODEGM-UHFFFAOYSA-N 0.000 claims 1
- SGPKXKUDYCPOBE-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-6-oxo-1-pyridin-3-yl-2h-pyrazin-3-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound O=C1C(N)=NC(C)(C=2C(=CC=C(NC(=O)C=3N=CC(Br)=CC=3)C=2)F)CN1C1=CC=CN=C1 SGPKXKUDYCPOBE-UHFFFAOYSA-N 0.000 claims 1
- YUOPBZQOSQHOJB-UHFFFAOYSA-N n-[3-[1-acetyl-5-amino-3-(difluoromethyl)-2,6-dihydropyrazin-3-yl]-4-fluorophenyl]-5-(difluoromethoxy)-3-methylpyridine-2-carboxamide Chemical compound C1N(C(=O)C)CC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=CC(OC(F)F)=CN=2)C)=CC=C1F YUOPBZQOSQHOJB-UHFFFAOYSA-N 0.000 claims 1
- JHDMJWNJCPZFBW-UHFFFAOYSA-N n-[3-[1-acetyl-5-amino-3-(difluoromethyl)-2,6-dihydropyrazin-3-yl]-4-fluorophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound C1N(C(=O)C)CC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Br)=CN=2)C)=CC=C1F JHDMJWNJCPZFBW-UHFFFAOYSA-N 0.000 claims 1
- FOLBFWMABGBJIK-UHFFFAOYSA-N n-[3-[5-amino-1-(2-methoxyethyl)-3-methyl-6-oxo-2h-pyrazin-3-yl]-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(CCOC)CC1(C)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)Cl)=CC=C1F FOLBFWMABGBJIK-UHFFFAOYSA-N 0.000 claims 1
- PZMNGGWMBNDIDP-UHFFFAOYSA-N n-[3-[5-amino-1-(2-methoxyethyl)-3-methyl-6-oxo-2h-pyrazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)C(=O)N(CCOC)CC1(C)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F PZMNGGWMBNDIDP-UHFFFAOYSA-N 0.000 claims 1
- PBVWMRZIDFSIRJ-UHFFFAOYSA-N n-[3-[5-amino-1-(cyclopropanecarbonyl)-3-(difluoromethyl)-2,6-dihydropyrazin-3-yl]-4-fluorophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C(C2(N=C(N)CN(C2)C(=O)C2CC2)C(F)F)=C1 PBVWMRZIDFSIRJ-UHFFFAOYSA-N 0.000 claims 1
- GFKHOTKTQLRBEC-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-1-(2-methoxyacetyl)-2,6-dihydropyrazin-3-yl]-4-fluorophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound C1N(C(=O)COC)CC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Br)=CN=2)C)=CC=C1F GFKHOTKTQLRBEC-UHFFFAOYSA-N 0.000 claims 1
- ZKECAQPFRZAODT-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1h-pyrazin-3-yl]-4-fluorophenyl]-5-(difluoromethoxy)-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(OC(F)F)=CN=C1C(=O)NC1=CC=C(F)C(C2(N=C(N)CNC2)C(F)F)=C1 ZKECAQPFRZAODT-UHFFFAOYSA-N 0.000 claims 1
- YIVQZDWEYRMEFX-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1h-pyrazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1NCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F YIVQZDWEYRMEFX-UHFFFAOYSA-N 0.000 claims 1
- UUBHPJXFLIBPAK-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1h-pyrazin-3-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C1NCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2N=CC(=CC=2)C#N)=CC=C1F UUBHPJXFLIBPAK-UHFFFAOYSA-N 0.000 claims 1
- QQJJZOBMLMQJSH-UHFFFAOYSA-N n-[3-[5-amino-3-methyl-1-(1-methylpyrazol-4-yl)-6-oxo-2h-pyrazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1=NN(C)C=C1N1C(=O)C(N)=NC(C)(C=2C(=CC=C(NC(=O)C=3N=CC(Br)=CC=3)C=2)F)C1 QQJJZOBMLMQJSH-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29172409P | 2009-12-31 | 2009-12-31 | |
| US61/291,724 | 2009-12-31 | ||
| PCT/EP2010/070502 WO2011080176A1 (en) | 2009-12-31 | 2010-12-22 | Pyrazine derivatives and their use in the treatment of neurological disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013516395A JP2013516395A (ja) | 2013-05-13 |
| JP2013516395A5 true JP2013516395A5 (enExample) | 2014-08-21 |
| JP5600754B2 JP5600754B2 (ja) | 2014-10-01 |
Family
ID=43598456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012546418A Expired - Fee Related JP5600754B2 (ja) | 2009-12-31 | 2010-12-22 | ピラジン誘導体および神経障害の処置におけるそれらの使用 |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US20120277244A1 (enExample) |
| EP (1) | EP2519515B1 (enExample) |
| JP (1) | JP5600754B2 (enExample) |
| KR (1) | KR101419157B1 (enExample) |
| CN (1) | CN102712621B (enExample) |
| AU (1) | AU2010338365B2 (enExample) |
| BR (1) | BR112012015916A2 (enExample) |
| CA (1) | CA2785341A1 (enExample) |
| CL (1) | CL2012001762A1 (enExample) |
| CR (1) | CR20120332A (enExample) |
| CU (1) | CU20120099A7 (enExample) |
| EA (1) | EA201200952A1 (enExample) |
| EC (1) | ECSP12012065A (enExample) |
| ES (1) | ES2445536T3 (enExample) |
| GT (1) | GT201200219A (enExample) |
| HN (1) | HN2012001413A (enExample) |
| IL (1) | IL220268A0 (enExample) |
| MX (1) | MX2012007754A (enExample) |
| NZ (1) | NZ600136A (enExample) |
| PE (1) | PE20121640A1 (enExample) |
| PH (1) | PH12012501007A1 (enExample) |
| PL (1) | PL2519515T3 (enExample) |
| PT (1) | PT2519515E (enExample) |
| SG (1) | SG181431A1 (enExample) |
| TN (1) | TN2012000249A1 (enExample) |
| WO (1) | WO2011080176A1 (enExample) |
| ZA (1) | ZA201203614B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006307314C1 (en) | 2005-10-25 | 2011-08-25 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivative |
| ES2476605T3 (es) | 2007-04-24 | 2014-07-15 | Shionogi & Co., Ltd. | Derivados de aminohidrotiazina sustituidos con grupos cíclicos |
| JP5383483B2 (ja) | 2007-04-24 | 2014-01-08 | 塩野義製薬株式会社 | アルツハイマー症治療用医薬組成物 |
| AU2009258496B8 (en) | 2008-06-13 | 2014-06-26 | Shionogi & Co., Ltd. | Sulfur-containing heterocyclic derivative having beta-secretase-inhibiting activity |
| WO2010047372A1 (ja) | 2008-10-22 | 2010-04-29 | 塩野義製薬株式会社 | Ｂａｃｅ１阻害活性を有する２－アミノピリミジン－４－オンおよび２－アミノピリジン誘導体 |
| UA108363C2 (uk) | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
| UA110467C2 (uk) | 2009-12-11 | 2016-01-12 | Шионогі Енд Ко., Лтд. | Похідні оксазину |
| US20130079349A1 (en) * | 2010-06-09 | 2013-03-28 | Janssen Pharmaceutica Nv | 5-amino-3,6-dihydro-1h-pyrazin-2-one derivatives useful as inhibitors of beta-secretase (bace) |
| PH12012502377A1 (en) | 2010-06-09 | 2014-10-14 | Janssen Pharmaceutica Nv | 5,6-dihydro-2h-[1,4]oxazin-3-yl-amine derivatives useful as inhibitors of beta-secretase (bace) |
| KR20130089231A (ko) * | 2010-06-28 | 2013-08-09 | 얀센 파마슈티카 엔.브이. | 알츠하이머병 및 다른 형태의 치매 치료용으로 유용한 3-아미노-5,6-디하이드로-1ｈ-피라진-2-온 유도체 |
| CN103261199A (zh) | 2010-10-29 | 2013-08-21 | 盐野义制药株式会社 | 萘啶衍生物 |
| JP5766198B2 (ja) | 2010-10-29 | 2015-08-19 | 塩野義製薬株式会社 | 縮合アミノジヒドロピリミジン誘導体 |
| NZ610948A (en) | 2010-12-22 | 2014-06-27 | Janssen Pharmaceutica Nv | 5,6-dihydro-imidazo[1,2-a]pyrazin-8-ylamine derivatives useful as inhibitors of beta-secretase (bace) |
| US8524897B2 (en) | 2011-01-12 | 2013-09-03 | Novartis Ag | Crystalline oxazine derivative |
| PT2663561E (pt) | 2011-01-13 | 2016-06-07 | Novartis Ag | Derivados heterocíclicos novos e sua utilização no tratamento de distúrbios neurológicos |
| JP2014505689A (ja) * | 2011-01-13 | 2014-03-06 | ノバルティス アーゲー | 代謝障害の処置用ｂａｃｅ−２阻害剤 |
| JP5853033B2 (ja) | 2011-03-01 | 2016-02-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプＪａｎｓｓｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａ Ｎａａｍｌｏｚｅ Ｖｅｎｎｏｏｔｓｃｈａｐ | β−セクレターゼ（ＢＡＣＥ）の阻害剤として有用な６，７−ジヒドロ−ピラゾロ［１，５−ａ］ピラジン−４−イルアミン誘導体 |
| BR112013022917A2 (pt) | 2011-03-09 | 2016-12-06 | Janssen Pharmaceutica Nv | derivados 3,4-dihidro-pirrolo[1,2-a]pirazino-1-ilamina úteis como inibidores de beta-secretase (bace) |
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| US9145426B2 (en) | 2011-04-07 | 2015-09-29 | Merck Sharp & Dohme Corp. | Pyrrolidine-fused thiadiazine dioxide compounds as BACE inhibitors, compositions, and their use |
| AU2012243329B2 (en) | 2011-04-13 | 2015-09-17 | Merck Sharp & Dohme Corp. | 5-substituted iminothiazines and their mono-and dioxides as BACE inhibitors,compositions,and their use |
| CN103608345A (zh) | 2011-04-26 | 2014-02-26 | 盐野义制药株式会社 | 噁嗪衍生物和含有该噁嗪衍生物的bace1抑制剂 |
| KR20140054295A (ko) | 2011-08-22 | 2014-05-08 | 머크 샤프 앤드 돔 코포레이션 | Bace 억제제로서의 2-스피로-치환된 이미노티아진 및 그의 모노- 및 디옥시드, 조성물 및 그의 용도 |
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| KR102243133B1 (ko) | 2013-06-12 | 2021-04-22 | 얀센 파마슈티카 엔.브이. | 베타-세크레타제(bace) 저해제로서의 4-아미노-6-페닐-6,7-디하이드로[1,2,3]트리아졸로[1,5-a]피라진 유도체 |
| JP6325092B2 (ja) | 2013-06-12 | 2018-05-16 | ヤンセン ファーマシューティカ エヌ．ベー． | βーセクレターゼ（ＢＡＣＥ）の阻害剤としての４−アミノ−６−フェニル−５，６−ジヒドロイミダゾ［１，５−Ａ］ピラジン誘導体 |
| KR102243135B1 (ko) | 2013-06-12 | 2021-04-22 | 얀센 파마슈티카 엔.브이. | 베타-세크레타제(bace) 저해제로서의 4-아미노-6-페닐-5,6-디하이드로이미다조[1,5-a]피라진-3(2h)-온 유도체 |
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| NL6911868A (enExample) | 1968-08-31 | 1970-03-03 | ||
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| US20130079349A1 (en) * | 2010-06-09 | 2013-03-28 | Janssen Pharmaceutica Nv | 5-amino-3,6-dihydro-1h-pyrazin-2-one derivatives useful as inhibitors of beta-secretase (bace) |
| KR20130089231A (ko) * | 2010-06-28 | 2013-08-09 | 얀센 파마슈티카 엔.브이. | 알츠하이머병 및 다른 형태의 치매 치료용으로 유용한 3-아미노-5,6-디하이드로-1ｈ-피라진-2-온 유도체 |
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