JP2005510559A - Asp2阻害剤活性を有するヒドロキシエチレン化合物 - Google Patents
Asp2阻害剤活性を有するヒドロキシエチレン化合物 Download PDFInfo
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- JP2005510559A JP2005510559A JP2003547355A JP2003547355A JP2005510559A JP 2005510559 A JP2005510559 A JP 2005510559A JP 2003547355 A JP2003547355 A JP 2003547355A JP 2003547355 A JP2003547355 A JP 2003547355A JP 2005510559 A JP2005510559 A JP 2005510559A
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- alkyl
- benzyl
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- 102100021257 Beta-secretase 1 Human genes 0.000 title abstract description 20
- 101710150192 Beta-secretase 1 Proteins 0.000 title abstract description 17
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 title abstract description 3
- 230000000694 effects Effects 0.000 title description 3
- 239000003112 inhibitor Substances 0.000 title description 3
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims abstract description 30
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims abstract description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
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- 238000001556 precipitation Methods 0.000 claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- -1 bicyclo [2.2.1] hept-2-ylcarbamoyl Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- YSHQWXMZPYKBEO-YGOYIFOWSA-N n-[(2s,3s,5r)-6-(3,3-dimethylbutylamino)-3-hydroxy-5-methyl-6-oxo-1-phenylhexan-2-yl]-3-methylsulfonylbenzamide Chemical compound C([C@@H]([C@@H](O)C[C@@H](C)C(=O)NCCC(C)(C)C)NC(=O)C=1C=C(C=CC=1)S(C)(=O)=O)C1=CC=CC=C1 YSHQWXMZPYKBEO-YGOYIFOWSA-N 0.000 claims description 4
- FSANQGKLVRTEFH-ZUVGRRGESA-N N-[(2S,3S,5R)-5-(2-bicyclo[2.2.1]heptanylcarbamoyl)-3-hydroxy-8-methyl-1-phenylnonan-2-yl]-3-methylsulfonyl-5-propoxybenzamide Chemical compound CS(=O)(=O)C1=CC(OCCC)=CC(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@@H](O)C[C@@H](CCC(C)C)C(=O)NC2C3CCC(C3)C2)=C1 FSANQGKLVRTEFH-ZUVGRRGESA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- LUKQYLFCEYZVOF-HOJAQTOUSA-N n-[(2s,3s,5r)-6-(3,3-dimethylbutylamino)-3-hydroxy-5-methyl-6-oxo-1-phenylhexan-2-yl]-5-methylsulfonylthiophene-2-carboxamide Chemical compound C([C@@H]([C@@H](O)C[C@@H](C)C(=O)NCCC(C)(C)C)NC(=O)C=1SC(=CC=1)S(C)(=O)=O)C1=CC=CC=C1 LUKQYLFCEYZVOF-HOJAQTOUSA-N 0.000 claims description 3
- GTHIDBYCDWSTCL-XGMAVGGMSA-N n-[(2s,3s,5r)-6-(3-bicyclo[2.2.1]heptanylamino)-3-hydroxy-5-methyl-6-oxo-1-phenylhexan-2-yl]-3-methoxy-5-methylsulfonylpyridine-4-carboxamide Chemical compound COC1=CN=CC(S(C)(=O)=O)=C1C(=O)N[C@H]([C@@H](O)C[C@@H](C)C(=O)NC1C2CCC(C2)C1)CC1=CC=CC=C1 GTHIDBYCDWSTCL-XGMAVGGMSA-N 0.000 claims description 3
- YOWQAGWJEGZZAD-HUMIOPDMSA-N n-[(2s,3s,5r)-6-(3-bicyclo[2.2.1]heptanylamino)-3-hydroxy-5-methyl-6-oxo-1-phenylhexan-2-yl]-3-methylsulfonyl-5-(2-oxopyrrolidin-1-yl)benzamide Chemical compound C([C@@H]([C@@H](O)C[C@@H](C)C(=O)NC1C2CCC(C2)C1)NC(=O)C=1C=C(C=C(C=1)N1C(CCC1)=O)S(C)(=O)=O)C1=CC=CC=C1 YOWQAGWJEGZZAD-HUMIOPDMSA-N 0.000 claims description 3
- NQQNEJOPZMESIV-COPCDDAFSA-N n-[(2s,3s,5r)-6-(cyclohexylamino)-3-hydroxy-5-methyl-6-oxo-1-phenylhexan-2-yl]-3-methoxy-5-methylsulfonylpyridine-4-carboxamide Chemical compound COC1=CN=CC(S(C)(=O)=O)=C1C(=O)N[C@H]([C@@H](O)C[C@@H](C)C(=O)NC1CCCCC1)CC1=CC=CC=C1 NQQNEJOPZMESIV-COPCDDAFSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- KZKSCWDMDRSEKJ-OOEPTKCWSA-N n-[(2s,3s,5r)-6-(3-bicyclo[2.2.1]heptanylamino)-3-hydroxy-5-methyl-6-oxo-1-phenylhexan-2-yl]-3-methoxy-5-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC(OC)=CC(C(=O)N[C@@H](CC=2C=CC=CC=2)[C@@H](O)C[C@@H](C)C(=O)NC2C3CCC(C3)C2)=C1 KZKSCWDMDRSEKJ-OOEPTKCWSA-N 0.000 claims description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 37
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
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- 229940088598 enzyme Drugs 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000012267 brine Substances 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 239000000872 buffer Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- QSJVIYNRIIFQTR-UHFFFAOYSA-N 3-hydroxy-5-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC(O)=CC(C(O)=O)=C1 QSJVIYNRIIFQTR-UHFFFAOYSA-N 0.000 description 9
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- 239000000284 extract Substances 0.000 description 8
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- RJGKNTNJHTUTJD-UHFFFAOYSA-N 3-amino-5-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC(N)=CC(C(O)=O)=C1 RJGKNTNJHTUTJD-UHFFFAOYSA-N 0.000 description 7
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- ZZNYBVMFYCWKIZ-UHFFFAOYSA-N 3-methanesulfonyl-5-nitrobenzoic acid Chemical compound CS(=O)(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZZNYBVMFYCWKIZ-UHFFFAOYSA-N 0.000 description 5
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/42—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (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)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0128746A GB0128746D0 (en) | 2001-11-30 | 2001-11-30 | Novel compounds |
| GB0128747A GB0128747D0 (en) | 2001-11-30 | 2001-11-30 | Novel compounds |
| GB0214088A GB0214088D0 (en) | 2002-06-18 | 2002-06-18 | Novel compounds |
| PCT/EP2002/013517 WO2003045903A1 (en) | 2001-11-30 | 2002-11-29 | Hydroxyethylene compounds with asp2 inhibitory activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005510559A true JP2005510559A (ja) | 2005-04-21 |
| JP2005510559A5 JP2005510559A5 (https=) | 2006-01-05 |
Family
ID=27256340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003547355A Pending JP2005510559A (ja) | 2001-11-30 | 2002-11-29 | Asp2阻害剤活性を有するヒドロキシエチレン化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7160905B2 (https=) |
| EP (1) | EP1448516A1 (https=) |
| JP (1) | JP2005510559A (https=) |
| AU (1) | AU2002352189A1 (https=) |
| WO (1) | WO2003045903A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2007528402A (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 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0314302D0 (en) * | 2003-06-19 | 2003-07-23 | Glaxo Group Ltd | Novel compounds |
| KR20070107062A (ko) * | 2005-02-01 | 2007-11-06 | 와이어쓰 | β-세크리타제의 억제제로서의 아미노-피리딘 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60124080T2 (de) * | 2000-03-23 | 2007-03-01 | Elan Pharmaceuticals, Inc., San Francisco | Verbindungen und verfahren zur behandlung der alzheimerschen krankheit |
-
2002
- 2002-11-29 US US10/496,334 patent/US7160905B2/en not_active Expired - Fee Related
- 2002-11-29 AU AU2002352189A patent/AU2002352189A1/en not_active Abandoned
- 2002-11-29 EP EP02787874A patent/EP1448516A1/en not_active Withdrawn
- 2002-11-29 JP JP2003547355A patent/JP2005510559A/ja active Pending
- 2002-11-29 WO PCT/EP2002/013517 patent/WO2003045903A1/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2007528402A (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 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7160905B2 (en) | 2007-01-09 |
| US20050038028A1 (en) | 2005-02-17 |
| EP1448516A1 (en) | 2004-08-25 |
| WO2003045903A1 (en) | 2003-06-05 |
| AU2002352189A1 (en) | 2003-06-10 |
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