RU2006124863A - Трициклические производные индолгидроксиэтиламина и их применение при лечении болезни альцгеймера - Google Patents
Трициклические производные индолгидроксиэтиламина и их применение при лечении болезни альцгеймера Download PDFInfo
- Publication number
- RU2006124863A RU2006124863A RU2006124863/04A RU2006124863A RU2006124863A RU 2006124863 A RU2006124863 A RU 2006124863A RU 2006124863/04 A RU2006124863/04 A RU 2006124863/04A RU 2006124863 A RU2006124863 A RU 2006124863A RU 2006124863 A RU2006124863 A RU 2006124863A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- hydroxy
- propyl
- phenylmethyl
- tetrahydro
- Prior art date
Links
- 208000024827 Alzheimer disease Diseases 0.000 title abstract 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims abstract 10
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims abstract 10
- 201000010099 disease Diseases 0.000 claims abstract 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 5
- 208000037259 Amyloid Plaque Diseases 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 88
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 87
- VGPKJZKKCPUOEF-UHFFFAOYSA-N 10,10-dioxo-10lambda6-thia-3,9-diazatricyclo[6.4.1.04,13]trideca-1(13),2,4,6,8,11-hexaene-6-carboxamide Chemical compound N=1S(C=CC=2C=NC3=CC(=CC1C23)C(=O)N)(=O)=O VGPKJZKKCPUOEF-UHFFFAOYSA-N 0.000 claims 84
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 61
- -1 cyano, hydroxy Chemical group 0.000 claims 49
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 9
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- TYABZJINIKXMCL-LBNVMWSVSA-N 1,6-diethyl-n-[(1s,2r)-2-hydroxy-1-(phenylmethyl)-3-(tetrahydro-2h-pyran-4-ylamino)propyl]-1,3,4,6-tetrahydro[1,2]thiazepino[5,4,3-cd]indole-8-carboxamide 2,2-dioxide Chemical compound C([C@H](NC(=O)C=1C=C2N(S(CCC3=CN(CC)C(=C23)C=1)(=O)=O)CC)[C@H](O)CNC1CCOCC1)C1=CC=CC=C1 TYABZJINIKXMCL-LBNVMWSVSA-N 0.000 claims 1
- CYWIMYQJZNCIBU-LBNVMWSVSA-N 1,6-diethyl-n-[(1s,2r)-2-hydroxy-1-(phenylmethyl)-3-(tetrahydro-2h-pyran-4-ylamino)propyl]-1,6-dihydro[1,2]thiazepino[5,4,3-cd]indole-8-carboxamide 2,2-dioxide Chemical compound C([C@H](NC(=O)C=1C=C2N(S(C=CC3=CN(CC)C(=C23)C=1)(=O)=O)CC)[C@H](O)CNC1CCOCC1)C1=CC=CC=C1 CYWIMYQJZNCIBU-LBNVMWSVSA-N 0.000 claims 1
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 125000006308 propyl amino group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 102100021257 Beta-secretase 1 Human genes 0.000 abstract 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 1
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 abstract 1
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 abstract 1
- 101710150192 Beta-secretase 1 Proteins 0.000 abstract 1
- 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0328900.6A GB0328900D0 (en) | 2003-12-12 | 2003-12-12 | Novel compounds |
| GB0328900.6 | 2003-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2006124863A true RU2006124863A (ru) | 2008-01-20 |
Family
ID=30130158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006124863/04A RU2006124863A (ru) | 2003-12-12 | 2004-12-09 | Трициклические производные индолгидроксиэтиламина и их применение при лечении болезни альцгеймера |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20070073060A1 (https=) |
| EP (1) | EP1692143B1 (https=) |
| JP (1) | JP2007513913A (https=) |
| KR (1) | KR20060121164A (https=) |
| CN (1) | CN1914214A (https=) |
| AT (1) | ATE414090T1 (https=) |
| AU (1) | AU2004299231A1 (https=) |
| BR (1) | BRPI0417476A (https=) |
| CA (1) | CA2549072A1 (https=) |
| DE (1) | DE602004017777D1 (https=) |
| GB (1) | GB0328900D0 (https=) |
| IL (1) | IL175819A0 (https=) |
| IS (1) | IS8521A (https=) |
| MA (1) | MA28241A1 (https=) |
| NO (1) | NO20063137L (https=) |
| RU (1) | RU2006124863A (https=) |
| WO (1) | WO2005058915A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007528400A (ja) | 2004-03-09 | 2007-10-11 | エラン ファーマシューティカルズ，インコーポレイテッド | 置換ヒドロキシエチルアミン系のアスパラギン酸プロテアーゼ阻害薬 |
| WO2006010095A2 (en) | 2004-07-09 | 2006-01-26 | Elan Pharmaceuticals Inc. | Oxime derivative substituted hydroxyethylamine aspartyl protease inhibitors |
| 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 |
| GB0422766D0 (en) * | 2004-10-13 | 2004-11-17 | Glaxo Group Ltd | Novel compounds |
| WO2007047305A1 (en) | 2005-10-12 | 2007-04-26 | Elan Pharmaceuticals, Inc. | Methods of treating amyloidosis using cyclopropyl derivative aspartyl protease inhibitors |
| US7872009B2 (en) | 2005-11-21 | 2011-01-18 | Amgen Inc. | Beta-Secretase modulators and methods of use |
| US7838676B2 (en) * | 2005-11-21 | 2010-11-23 | Amgen Inc. | Beta-secretase modulators and methods of use |
| 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. |
| 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. |
| PL2185561T3 (pl) * | 2007-07-27 | 2011-11-30 | Sanofi Aventis | Pochodne 1,2,3,4-tetrahydropirolo(1,2-a)pirazyno-6-karboksamidów i 2,3,4,5-tetrahydropirolo(1,2-a)-diazepino-7-karboksamidów, ich wytwarzanie i zastosowanie terapeutyczne |
| 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. |
| 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. |
| KR101653707B1 (ko) * | 2008-05-29 | 2016-09-02 | 알바니 몰레큘라 리써치, 인크. | 5-ｈｔ3 수용체 조절제, 이의 제조 방법, 및 그의 용도 |
| FR2960876B1 (fr) | 2010-06-03 | 2012-07-27 | Sanofi Aventis | Derives de 3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1h)-dicarboxamide leur preparation et leur application en therapeutique. |
| WO2011153359A1 (en) | 2010-06-04 | 2011-12-08 | Albany Molecular Research, Inc. | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| MX365851B (es) * | 2012-08-24 | 2019-06-17 | Treventis Corp | Compuestos de benzofurazano anti-amiloides y metodos. |
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0958293B1 (en) * | 1997-02-04 | 2005-01-19 | 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 |
| DE60124080T2 (de) * | 2000-03-23 | 2007-03-01 | Elan Pharmaceuticals, Inc., San Francisco | Verbindungen und verfahren zur behandlung der alzheimerschen krankheit |
| JP2004502664A (ja) * | 2000-06-30 | 2004-01-29 | イーラン ファーマスーティカルズ、インコーポレイテッド | アルツハイマー病処置用化合物 |
| AU2002359376B2 (en) * | 2001-11-08 | 2008-01-10 | Elan Pharmaceuticals, Inc. | N, N'-substituted-1,3-diamino-2-hydroxypropane derivatives |
| GB0228410D0 (en) * | 2002-12-05 | 2003-01-08 | Glaxo Group Ltd | Novel Compounds |
| GB0309221D0 (en) * | 2003-04-23 | 2003-06-04 | Glaxo Group Ltd | Novel compounds |
-
2003
- 2003-12-12 GB GBGB0328900.6A patent/GB0328900D0/en not_active Ceased
-
2004
- 2004-12-09 JP JP2006543488A patent/JP2007513913A/ja not_active Withdrawn
- 2004-12-09 KR KR1020067011376A patent/KR20060121164A/ko not_active Withdrawn
- 2004-12-09 DE DE602004017777T patent/DE602004017777D1/de not_active Expired - Fee Related
- 2004-12-09 RU RU2006124863/04A patent/RU2006124863A/ru not_active Application Discontinuation
- 2004-12-09 US US10/596,296 patent/US20070073060A1/en not_active Abandoned
- 2004-12-09 AT AT04803724T patent/ATE414090T1/de not_active IP Right Cessation
- 2004-12-09 BR BRPI0417476-3A patent/BRPI0417476A/pt not_active IP Right Cessation
- 2004-12-09 WO PCT/EP2004/014076 patent/WO2005058915A1/en not_active Ceased
- 2004-12-09 AU AU2004299231A patent/AU2004299231A1/en not_active Abandoned
- 2004-12-09 CN CNA2004800416435A patent/CN1914214A/zh active Pending
- 2004-12-09 CA CA002549072A patent/CA2549072A1/en not_active Abandoned
- 2004-12-09 EP EP04803724A patent/EP1692143B1/en not_active Expired - Lifetime
-
2006
- 2006-05-22 IL IL175819A patent/IL175819A0/en unknown
- 2006-06-26 MA MA29143A patent/MA28241A1/fr unknown
- 2006-06-26 IS IS8521A patent/IS8521A/xx unknown
- 2006-07-06 NO NO20063137A patent/NO20063137L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0417476A (pt) | 2007-05-08 |
| EP1692143B1 (en) | 2008-11-12 |
| CA2549072A1 (en) | 2005-06-30 |
| JP2007513913A (ja) | 2007-05-31 |
| GB0328900D0 (en) | 2004-01-14 |
| KR20060121164A (ko) | 2006-11-28 |
| DE602004017777D1 (de) | 2008-12-24 |
| NO20063137L (no) | 2006-08-31 |
| ATE414090T1 (de) | 2008-11-15 |
| MA28241A1 (fr) | 2006-10-02 |
| IL175819A0 (en) | 2006-10-05 |
| AU2004299231A1 (en) | 2005-06-30 |
| US20070073060A1 (en) | 2007-03-29 |
| WO2005058915A1 (en) | 2005-06-30 |
| IS8521A (is) | 2006-06-26 |
| CN1914214A (zh) | 2007-02-14 |
| EP1692143A1 (en) | 2006-08-23 |
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