JP5675340B2 - 新規阻害剤 - Google Patents
新規阻害剤 Download PDFInfo
- Publication number
- JP5675340B2 JP5675340B2 JP2010503510A JP2010503510A JP5675340B2 JP 5675340 B2 JP5675340 B2 JP 5675340B2 JP 2010503510 A JP2010503510 A JP 2010503510A JP 2010503510 A JP2010503510 A JP 2010503510A JP 5675340 B2 JP5675340 B2 JP 5675340B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- inhibitor
- imidazol
- nitrovinyl
- 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.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title claims description 165
- 150000001875 compounds Chemical class 0.000 claims description 144
- -1 cyano, hydroxyl Chemical group 0.000 claims description 137
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 239000003814 drug Substances 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
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- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 17
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 108010081484 glutaminyl-peptide cyclotransferase Proteins 0.000 claims description 15
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- 229940079593 drug Drugs 0.000 claims description 14
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
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- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004001 thioalkyl group Chemical group 0.000 claims description 7
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
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- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 claims description 6
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Classifications
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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| PCT/EP2008/054710 WO2008128981A1 (en) | 2007-04-18 | 2008-04-18 | Nitrovinyl-diamine derivatives as glutaminyl cyclase inhibitors |
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| US9925282B2 (en) | 2009-01-29 | 2018-03-27 | The General Hospital Corporation | Cromolyn derivatives and related methods of imaging and treatment |
| KR101755737B1 (ko) | 2009-09-11 | 2017-07-07 | 프로비오드룩 아게 | 글루타미닐 사이클라제의 억제제로서 헤테로사이클릭 유도체 |
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| US10525005B2 (en) | 2013-05-23 | 2020-01-07 | The General Hospital Corporation | Cromolyn compositions and methods thereof |
| CN110305095A (zh) | 2013-10-22 | 2019-10-08 | 综合医院公司 | 色甘酸衍生物以及成像和治疗的相关方法 |
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| DE3044566A1 (de) * | 1980-11-26 | 1982-07-15 | Basf Ag, 6700 Ludwigshafen | N-substituierte imidazol-derivate, ihre herstellung, diese enthaltende arzneimittel und ihre verwendung |
| WO2001070696A1 (en) | 2000-03-21 | 2001-09-27 | Ishihara Sangyo Kaisha, Ltd. | Nitroethenamine derivatives or salts thereof and pharmaceutical compositions containing the derivatives or the salts |
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| WO2008034891A2 (en) * | 2006-09-21 | 2008-03-27 | Probiodrug Ag | Novel genes related to glutaminyl cyclase |
| US7741354B2 (en) * | 2006-11-09 | 2010-06-22 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| US8420684B2 (en) * | 2006-11-09 | 2013-04-16 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| DK2091948T3 (da) * | 2006-11-30 | 2012-07-23 | Probiodrug Ag | Nye inhibitorer af glutaminylcyclase |
| DK2121944T3 (da) * | 2007-01-19 | 2011-10-31 | Probiodrug Ag | In vivo screeningsmodeller til behandling af Alzheimers sygdom og andre QPCT-relaterede lidelser |
| JP5612860B2 (ja) * | 2007-03-09 | 2014-10-22 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのイミダゾ［１，５−ａ］ピリジン誘導体 |
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2008
- 2008-04-18 ES ES08736360.2T patent/ES2468551T3/es active Active
- 2008-04-18 EP EP08736360.2A patent/EP2142513B1/en active Active
- 2008-04-18 US US12/105,730 patent/US8772508B2/en active Active
- 2008-04-18 JP JP2010503510A patent/JP5675340B2/ja not_active Expired - Fee Related
- 2008-04-18 DK DK08736360.2T patent/DK2142513T3/da active
- 2008-04-18 WO PCT/EP2008/054710 patent/WO2008128981A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2142513A1 (en) | 2010-01-13 |
| WO2008128981A1 (en) | 2008-10-30 |
| ES2468551T3 (es) | 2014-06-16 |
| JP2010524893A (ja) | 2010-07-22 |
| EP2142513B1 (en) | 2014-03-12 |
| US20080292582A1 (en) | 2008-11-27 |
| US8772508B2 (en) | 2014-07-08 |
| DK2142513T3 (da) | 2014-06-10 |
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