CA2472617A1 - Substituted amino carboxamides for the treatment of alzheimer's disease - Google Patents
Substituted amino carboxamides for the treatment of alzheimer's disease Download PDFInfo
- Publication number
- CA2472617A1 CA2472617A1 CA002472617A CA2472617A CA2472617A1 CA 2472617 A1 CA2472617 A1 CA 2472617A1 CA 002472617 A CA002472617 A CA 002472617A CA 2472617 A CA2472617 A CA 2472617A CA 2472617 A1 CA2472617 A1 CA 2472617A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optionally substituted
- aryl
- amino
- independently selected
- 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.)
- Abandoned
Links
- 208000024827 Alzheimer disease Diseases 0.000 title claims abstract description 76
- 238000011282 treatment Methods 0.000 title claims abstract description 38
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 324
- 238000000034 method Methods 0.000 claims abstract description 98
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 61
- 201000010099 disease Diseases 0.000 claims abstract description 56
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 203
- 125000000217 alkyl group Chemical group 0.000 claims description 190
- -1 -C.ident.N Chemical group 0.000 claims description 177
- 229910052736 halogen Inorganic materials 0.000 claims description 142
- 150000002367 halogens Chemical class 0.000 claims description 140
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 107
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 105
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 97
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 60
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 47
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 42
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 41
- 206010012289 Dementia Diseases 0.000 claims description 32
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 24
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 23
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 208000010877 cognitive disease Diseases 0.000 claims description 21
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 21
- 230000003412 degenerative effect Effects 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 15
- 201000010374 Down Syndrome Diseases 0.000 claims description 14
- 206010044688 Trisomy 21 Diseases 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 208000018282 ACys amyloidosis Diseases 0.000 claims description 13
- 208000007487 Familial Cerebral Amyloid Angiopathy Diseases 0.000 claims description 13
- 208000032849 Hereditary cerebral hemorrhage with amyloidosis Diseases 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 210000004558 lewy body Anatomy 0.000 claims description 11
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 230000002792 vascular Effects 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 230000001054 cortical effect Effects 0.000 claims description 9
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- NCQYGBKQXRQAAG-JVPBZIDWSA-N (2s)-2-[[(2s)-2-[[(2s)-2-amino-3-(3,5-difluorophenyl)propyl]amino]propanoyl]amino]-3-methyl-n-(2-methylpropyl)butanamide Chemical group CC(C)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC[C@@H](N)CC1=CC(F)=CC(F)=C1 NCQYGBKQXRQAAG-JVPBZIDWSA-N 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 21
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 11
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- GGLRBZWDZQTZTO-JOYXZSCHSA-N 1-n-[(2s)-1-[[(2s)-1-[[(2s)-3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-phenylpropan-2-yl]-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC=CC(C(=O)N[C@H](CN[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)NCC(C)C)CC=2C=CC=CC=2)=C1 GGLRBZWDZQTZTO-JOYXZSCHSA-N 0.000 claims 1
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 abstract description 103
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- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 230000008021 deposition Effects 0.000 abstract description 3
- 241000124008 Mammalia Species 0.000 abstract description 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 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
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- 238000003776 cleavage reaction Methods 0.000 description 72
- 230000007017 scission Effects 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000000758 substrate Substances 0.000 description 50
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- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 32
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- A—HUMAN NECESSITIES
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34531602P | 2002-01-04 | 2002-01-04 | |
| US60/345,316 | 2002-01-04 | ||
| US35041902P | 2002-01-18 | 2002-01-18 | |
| US60/350,419 | 2002-01-18 | ||
| PCT/US2003/000326 WO2003057721A2 (en) | 2002-01-04 | 2003-01-06 | Substituted amino carboxamides for the treatment of alzheimer's disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2472617A1 true CA2472617A1 (en) | 2003-07-17 |
Family
ID=26994342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002472617A Abandoned CA2472617A1 (en) | 2002-01-04 | 2003-01-06 | Substituted amino carboxamides for the treatment of alzheimer's disease |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6962934B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1458745A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2005534614A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003206413A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0306724A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2472617A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA04006575A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2003057721A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003294441A1 (en) * | 2002-11-22 | 2004-06-18 | Bristol-Myers Squibb Company | 1-aryl-2-hydroxyethyl amides as potassium channel openers |
| US7521481B2 (en) * | 2003-02-27 | 2009-04-21 | Mclaurin Joanne | Methods of preventing, treating and diagnosing disorders of protein aggregation |
| JP2007516207A (ja) * | 2003-06-30 | 2007-06-21 | メルク エンド カムパニー インコーポレーテッド | アルツハイマー病の治療のためのＮ−アルキルフェニルカルボキサミドβ−セクレターゼ阻害剤 |
| EP1694635A2 (en) * | 2003-10-30 | 2006-08-30 | Elan Pharmaceuticals, Inc. | HYDROXYPROPYL AMIDES FOR THE TREATMENT OF ALZHEIMER’S DISEASE |
| JP2007517781A (ja) | 2003-12-19 | 2007-07-05 | メルク エンド カムパニー インコーポレーテッド | アルツハイマー病治療用のフェニルアミドおよびピリジルアミド系β−セクレターゼ阻害薬 |
| US20060014790A1 (en) * | 2004-01-21 | 2006-01-19 | Varghese John | Methods of treatment of amyloidosis using spirocyclohexane aspartyl-protease inhibitors |
| US7847100B2 (en) | 2004-04-20 | 2010-12-07 | Merck, Sharp & Dohme, Inc. | 1,3,5-substituted phenyl derivative compounds useful as beta-secretase inhibitors for the treatment of Alzheimer's disease |
| AU2005236063A1 (en) | 2004-04-20 | 2005-11-03 | Merck & Co., Inc. | 2, 4, 6-substituted pyridyl derivative compounds useful as beta-secretase inhibitors for the treatment of Alzheimer's disease |
| WO2005113582A1 (en) * | 2004-05-22 | 2005-12-01 | Boehringer Ingelheim International Gmbh | Substituted ethane-1,2-diamines for the treatment of alzheimer's disease |
| EP1758854B1 (en) * | 2004-06-15 | 2014-07-16 | Merck Sharp & Dohme Corp. | Pyrrolidin-3-yl compounds useful as beta-secretase inhibitors for the treatment of alzheimer's disease |
| CA2603404A1 (en) | 2005-03-30 | 2006-10-05 | Boehringer Ingelheim International Gmbh | Substituted 1,2-ethylendiamines, medicaments comprising said compound; their use and their method of manufacture |
| MX2007012341A (es) | 2005-04-08 | 2008-02-12 | Comentis Inc | Compuestos que inhiben actividad beta-secretasa y metodos de uso de los mismos. |
| EP1919861A2 (de) * | 2005-08-11 | 2008-05-14 | Boehringer Ingelheim International GmbH | Verbindungen zur behandlung der alzheimer erkrankung |
| US20090042867A1 (en) * | 2005-08-11 | 2009-02-12 | Klaus Fuchs | Compounds for the treatment of alzheimer's disease |
| CA2618474A1 (en) * | 2005-08-11 | 2007-02-15 | Boehringer Ingelheim International Gmbh | Compounds for treating alzheimer's disease |
| EP1915339A1 (de) * | 2005-08-11 | 2008-04-30 | Boehringer Ingelheim International GmbH | Inhibitoren der beta-sekretase zur behandlung der alzheimer- erkrankung |
| 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 |
| 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 |
| 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. |
| CA2687608C (en) | 2007-05-25 | 2013-07-02 | Amgen Inc. | Substituted hydroxyethyl amine compounds as beta-secretase modulators and methods of use |
| JP5450407B2 (ja) | 2007-07-06 | 2014-03-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 置換アミノ−キナゾリノン、前記化合物を含む薬物、それらの使用及び製造方法 |
| US7803809B2 (en) | 2008-11-12 | 2010-09-28 | Amgen Inc. | Substituted pyrano [2,3-b] pyridinamine compounds as beta-secretase modulators and methods of use |
| MX2011002705A (es) * | 2008-09-11 | 2011-09-09 | Amgen Inc | Compuestos con anillos espiro-triciclicos como moduladores de beta-secretasas y metodos de uso. |
| US8822485B2 (en) | 2009-11-23 | 2014-09-02 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| WO2011063233A1 (en) | 2009-11-23 | 2011-05-26 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| WO2011090911A1 (en) | 2010-01-19 | 2011-07-28 | Amgen Inc. | Amino heteroaryl compounds as beta-secretase modulators and methods of use |
| MX2012010658A (es) | 2010-03-15 | 2012-12-05 | Amgen Inc | Compuestos de anillo espiro tetraciclico como moduladores de beta-secretasa. |
| US8497264B2 (en) | 2010-03-15 | 2013-07-30 | Amgen Inc. | Amino-oxazines and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
| US9346827B2 (en) | 2011-02-07 | 2016-05-24 | Amgen Inc. | 5-amino-oxazepine and 5-amino-thiazepane compounds as beta secretase antagonists and methods of use |
| WO2013044092A1 (en) | 2011-09-21 | 2013-03-28 | Amgen Inc. | Amino-oxazines and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
| US9725469B2 (en) | 2012-11-15 | 2017-08-08 | Amgen, Inc. | Amino-oxazine and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5696270A (en) | 1989-05-23 | 1997-12-09 | Abbott Laboratories | Intermediate for making retroviral protease inhibiting compounds |
| US5362912A (en) | 1989-05-23 | 1994-11-08 | Abbott Laboratories | Process for the preparation of a substituted diaminodiol |
| US5352705A (en) * | 1992-06-26 | 1994-10-04 | Merck & Co., Inc. | Inhibitors of farnesyl protein transferase |
| DE69334250D1 (de) | 1992-12-29 | 2009-01-29 | Abbott Lab | Verfahren und Intermediate zur Herstellung von retroviralen Proteasehemmern |
| JPH11507538A (ja) | 1995-06-07 | 1999-07-06 | アテナ ニューロサイエンシズ インコーポレイティド | β−セクレターゼ、β−セクレターゼに対する抗体、及びβ−セクレターゼ阻害を検出するためのアッセイ |
| AU4329499A (en) * | 1998-07-30 | 2000-02-21 | Warner-Lambert Company | Reduced dipeptide analogues as calcium channel antagonists |
| JP2003502342A (ja) | 1999-06-15 | 2003-01-21 | エラン ファーマスーティカルズ インコーポレイテッド | ベータ−セクレターゼのスタチン誘導テトラペプチド阻害剤 |
-
2003
- 2003-01-06 AU AU2003206413A patent/AU2003206413A1/en not_active Abandoned
- 2003-01-06 US US10/337,075 patent/US6962934B2/en not_active Expired - Fee Related
- 2003-01-06 WO PCT/US2003/000326 patent/WO2003057721A2/en not_active Ceased
- 2003-01-06 JP JP2003558035A patent/JP2005534614A/ja active Pending
- 2003-01-06 BR BRPI0306724-6A patent/BR0306724A/pt not_active IP Right Cessation
- 2003-01-06 CA CA002472617A patent/CA2472617A1/en not_active Abandoned
- 2003-01-06 EP EP03703711A patent/EP1458745A2/en not_active Withdrawn
-
2004
- 2004-07-02 MX MXPA04006575A patent/MXPA04006575A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| US6962934B2 (en) | 2005-11-08 |
| EP1458745A2 (en) | 2004-09-22 |
| BR0306724A (pt) | 2006-04-11 |
| WO2003057721A3 (en) | 2004-03-25 |
| JP2005534614A (ja) | 2005-11-17 |
| WO2003057721A2 (en) | 2003-07-17 |
| MXPA04006575A (es) | 2004-10-04 |
| AU2003206413A8 (en) | 2003-07-24 |
| AU2003206413A1 (en) | 2003-07-24 |
| US20030166580A1 (en) | 2003-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20110106 |