CA2660441A1 - Imidazole amines as inhibitors of .beta.-secretase - Google Patents
Imidazole amines as inhibitors of .beta.-secretase Download PDFInfo
- Publication number
- CA2660441A1 CA2660441A1 CA002660441A CA2660441A CA2660441A1 CA 2660441 A1 CA2660441 A1 CA 2660441A1 CA 002660441 A CA002660441 A CA 002660441A CA 2660441 A CA2660441 A CA 2660441A CA 2660441 A1 CA2660441 A1 CA 2660441A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- optionally substituted
- phenyl
- 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.)
- Abandoned
Links
- -1 Imidazole amines Chemical class 0.000 title claims description 30
- 239000003112 inhibitor Substances 0.000 title description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
- 208000035475 disorder Diseases 0.000 claims abstract description 15
- 201000010099 disease Diseases 0.000 claims abstract description 13
- 208000037259 Amyloid Plaque Diseases 0.000 claims abstract description 12
- 230000002265 prevention Effects 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- 208000024827 Alzheimer disease Diseases 0.000 claims description 14
- 102100021257 Beta-secretase 1 Human genes 0.000 claims description 14
- 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 201000010374 Down Syndrome Diseases 0.000 claims description 5
- 206010044688 Trisomy 21 Diseases 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 210000002682 neurofibrillary tangle Anatomy 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 3
- SCODXNNXABJQIY-UHFFFAOYSA-N 8-[3-(2-fluoropyridin-3-yl)phenyl]-8-[4-(trifluoromethoxy)phenyl]-3,4-dihydroimidazo[5,1-c][1,2,4]oxadiazin-6-amine Chemical compound C12=NOCCN2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=C(OC(F)(F)F)C=C1 SCODXNNXABJQIY-UHFFFAOYSA-N 0.000 claims description 2
- QIQBZQYBYKQPSP-UHFFFAOYSA-N 8-[3-(5-fluoropyridin-3-yl)phenyl]-8-[4-(trifluoromethoxy)phenyl]-3,4-dihydroimidazo[5,1-c][1,2,4]oxadiazin-6-amine Chemical compound C12=NOCCN2C(N)=NC1(C=1C=C(C=CC=1)C=1C=C(F)C=NC=1)C1=CC=C(OC(F)(F)F)C=C1 QIQBZQYBYKQPSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000006999 cognitive decline Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- RRDVLXWUXDSNDZ-UHFFFAOYSA-N 8-(2,6-diethylpyridin-4-yl)-8-[3-(2-fluoropyridin-3-yl)phenyl]-3,4-dihydro-2h-imidazo[1,5-a]pyrimidin-6-amine Chemical compound CCC1=NC(CC)=CC(C2(C3=NCCCN3C(N)=N2)C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)=C1 RRDVLXWUXDSNDZ-UHFFFAOYSA-N 0.000 claims 1
- BTKIVAGPTLXEER-UHFFFAOYSA-N 8-[3-(2-fluoropyridin-3-yl)phenyl]-8-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]-3,4-dihydro-2h-imidazo[1,5-a]pyrimidin-6-amine Chemical compound C12=NCCCN2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C=1C=NN(CC(F)(F)F)C=1 BTKIVAGPTLXEER-UHFFFAOYSA-N 0.000 claims 1
- SIFXKACBEOUPOD-UHFFFAOYSA-N 8-[3-(2-fluoropyridin-3-yl)phenyl]-8-pyridin-4-yl-3,4-dihydro-2h-imidazo[1,5-a]pyrimidin-6-amine Chemical compound C12=NCCCN2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=NC=C1 SIFXKACBEOUPOD-UHFFFAOYSA-N 0.000 claims 1
- 208000024667 ABeta amyloidosis, Dutch type Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 1
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims 1
- 208000036536 dutch type ABeta amyloidosis Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 abstract description 3
- 108010090849 Amyloid beta-Peptides Proteins 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 25
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 239000000758 substrate Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 19
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000908 ammonium hydroxide Substances 0.000 description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- 238000003818 flash chromatography Methods 0.000 description 16
- 239000000377 silicon dioxide Substances 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 14
- 108090000790 Enzymes Proteins 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 101800001718 Amyloid-beta protein Proteins 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
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- 235000011152 sodium sulphate Nutrition 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- 210000004556 brain Anatomy 0.000 description 9
- UMCMPZBLKLEWAF-BCTGSCMUSA-N 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 UMCMPZBLKLEWAF-BCTGSCMUSA-N 0.000 description 8
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 8
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 8
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 8
- 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 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83835706P | 2006-08-17 | 2006-08-17 | |
| US60/838,357 | 2006-08-17 | ||
| PCT/US2007/075690 WO2008022024A2 (en) | 2006-08-17 | 2007-08-10 | Imidazole amines as inhibitors of beta-secretase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2660441A1 true CA2660441A1 (en) | 2008-02-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002660441A Abandoned CA2660441A1 (en) | 2006-08-17 | 2007-08-10 | Imidazole amines as inhibitors of .beta.-secretase |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2054414A2 (es) |
| JP (1) | JP2010500999A (es) |
| AR (1) | AR062409A1 (es) |
| CA (1) | CA2660441A1 (es) |
| CL (1) | CL2007002288A1 (es) |
| MX (1) | MX2009001699A (es) |
| PE (1) | PE20080744A1 (es) |
| TW (1) | TW200817406A (es) |
| WO (1) | WO2008022024A2 (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7763609B2 (en) | 2003-12-15 | 2010-07-27 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| US7592348B2 (en) | 2003-12-15 | 2009-09-22 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| US7700603B2 (en) | 2003-12-15 | 2010-04-20 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| KR20080029965A (ko) | 2005-06-14 | 2008-04-03 | 쉐링 코포레이션 | 아스파르틸 프로테아제 억제제 |
| BRPI0612545A2 (pt) | 2005-06-14 | 2010-11-23 | Schering Corp | compostos inibidores de protease, composições farmacêuticas e uso dos mesmos |
| ES2572263T3 (es) | 2005-10-25 | 2016-05-31 | Shionogi & Co | Derivados de dihidrooxazina y tetrahidropirimidina como inhibidores de BACE 1 |
| CA2653650A1 (en) | 2006-06-12 | 2007-12-21 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| EP2147914B1 (en) | 2007-04-24 | 2014-06-04 | Shionogi&Co., Ltd. | Aminodihydrothiazine derivatives substituted with cyclic groups |
| EP2151435A4 (en) | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| EP2283016B1 (en) | 2008-04-22 | 2014-09-24 | Merck Sharp & Dohme Corp. | Thiophenyl-substituted 2-imino-3-methyl pyrrolo pyrimidinone compounds as bace-1 inhibitors, compositions, and their use |
| KR101324426B1 (ko) | 2008-06-13 | 2013-10-31 | 시오노기세야쿠 가부시키가이샤 | β 세크레타제 저해 작용을 갖는 황 함유 복소환 유도체 |
| EP2360155A4 (en) | 2008-10-22 | 2012-06-20 | Shionogi & Co | 2-AMINOPYRIDIN-4-ON AND 2-AMINOPYRIDINE DERIVATIVE WITH BACE1-HEMDERING EFFECT |
| UA108363C2 (uk) | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
| CN102834384A (zh) | 2009-12-11 | 2012-12-19 | 盐野义制药株式会社 | *嗪衍生物 |
| US9018219B2 (en) | 2010-10-29 | 2015-04-28 | Shionogi & Co., Ltd. | Fused aminodihydropyrimidine derivative |
| WO2012057248A1 (ja) | 2010-10-29 | 2012-05-03 | 塩野義製薬株式会社 | ナフチリジン誘導体 |
| EP2694521B1 (en) | 2011-04-07 | 2015-11-25 | Merck Sharp & Dohme Corp. | Pyrrolidine-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| EP2694489B1 (en) | 2011-04-07 | 2017-09-06 | Merck Sharp & Dohme Corp. | C5-c6 oxacyclic-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| EP2703399A4 (en) | 2011-04-26 | 2014-10-15 | Shionogi & Co | OXAZINE DERIVATIVE AND BACE-1 HEMMER THEREOF |
| JP2014524472A (ja) | 2011-08-22 | 2014-09-22 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｂａｃｅ阻害剤としての２−スピロ置換イミノチアジンならびにそのモノオキシドおよびジオキシド、組成物、ならびにそれらの使用 |
| WO2014065434A1 (en) | 2012-10-24 | 2014-05-01 | Shionogi & Co., Ltd. | Dihydrooxazine or oxazepine derivatives having bace1 inhibitory activity |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06014792A (es) * | 2004-06-16 | 2007-02-16 | Wyeth Corp | Difenilimidazopirimidina y aminas imidazol como inhibidores de ??-secretasa. |
| ATE444962T1 (de) * | 2004-06-16 | 2009-10-15 | Wyeth Corp | Amino-5,5-diphenylimidazolon-derivate zur beta- sekretase-hemmung |
| BRPI0606690A2 (pt) * | 2005-01-14 | 2009-07-14 | Wyeth Corp | composto; uso do composto para o tratamento de uma doença ou distúrbio associado com uma atividade excessiva de bace; e composição farmacêutica |
| AU2006266167A1 (en) * | 2005-06-30 | 2007-01-11 | Wyeth | Amino-5-(6-membered)heteroarylimidazolone compounds and the use thereof for beta-secretase modulation |
| TW200738683A (en) * | 2005-06-30 | 2007-10-16 | Wyeth Corp | Amino-5-(5-membered)heteroarylimidazolone compounds and the use thereof for β-secretase modulation |
-
2007
- 2007-07-24 TW TW096126963A patent/TW200817406A/zh unknown
- 2007-08-07 CL CL200702288A patent/CL2007002288A1/es unknown
- 2007-08-07 PE PE2007001049A patent/PE20080744A1/es not_active Application Discontinuation
- 2007-08-10 CA CA002660441A patent/CA2660441A1/en not_active Abandoned
- 2007-08-10 JP JP2009524746A patent/JP2010500999A/ja not_active Withdrawn
- 2007-08-10 EP EP07840855A patent/EP2054414A2/en not_active Withdrawn
- 2007-08-10 MX MX2009001699A patent/MX2009001699A/es not_active Application Discontinuation
- 2007-08-10 WO PCT/US2007/075690 patent/WO2008022024A2/en active Application Filing
- 2007-08-16 AR ARP070103654A patent/AR062409A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200817406A (en) | 2008-04-16 |
| JP2010500999A (ja) | 2010-01-14 |
| EP2054414A2 (en) | 2009-05-06 |
| WO2008022024A2 (en) | 2008-02-21 |
| MX2009001699A (es) | 2009-02-25 |
| CL2007002288A1 (es) | 2008-02-08 |
| PE20080744A1 (es) | 2008-05-24 |
| AR062409A1 (es) | 2008-11-05 |
| WO2008022024A3 (en) | 2008-05-22 |
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