JP2005500370A - アクリルアミノチアゾール誘導体、それらの製造および治療的使用 - Google Patents
アクリルアミノチアゾール誘導体、それらの製造および治療的使用 Download PDFInfo
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- JP2005500370A JP2005500370A JP2003519045A JP2003519045A JP2005500370A JP 2005500370 A JP2005500370 A JP 2005500370A JP 2003519045 A JP2003519045 A JP 2003519045A JP 2003519045 A JP2003519045 A JP 2003519045A JP 2005500370 A JP2005500370 A JP 2005500370A
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- phenyl
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- methyl
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- -1 Acrylic aminothiazole derivatives Chemical class 0.000 title claims abstract description 78
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 230000001225 therapeutic effect Effects 0.000 title claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 125000005843 halogen group Chemical group 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
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- 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 claims description 9
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 206010059245 Angiopathy Diseases 0.000 claims description 3
- 201000010374 Down Syndrome Diseases 0.000 claims description 3
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- 206010044688 Trisomy 21 Diseases 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
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- 150000004677 hydrates Chemical class 0.000 claims description 3
- 230000008901 benefit Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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- 230000008569 process Effects 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 78
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 57
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 56
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 52
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 47
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 108090000765 processed proteins & peptides Proteins 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 230000014509 gene expression Effects 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 229940080818 propionamide Drugs 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 6
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 4
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 4
- ZLLOWHFKKIOINR-UHFFFAOYSA-N 5-phenyl-1,3-thiazole Chemical compound S1C=NC=C1C1=CC=CC=C1 ZLLOWHFKKIOINR-UHFFFAOYSA-N 0.000 description 4
- 238000002965 ELISA Methods 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
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- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
- IGGNSAVLXJKCNH-UHFFFAOYSA-N 2-(3,5-difluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC(F)=CC(F)=C1 IGGNSAVLXJKCNH-UHFFFAOYSA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- 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
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
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- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0110504 | 2001-08-06 | ||
| FR0207222A FR2840899B1 (fr) | 2002-06-12 | 2002-06-12 | Derives d'acylaminothiazole, leur preparation et leur utilisation en therapeutique |
| PCT/FR2002/002802 WO2003014095A1 (fr) | 2001-08-06 | 2002-08-05 | Derives d'acylaminothiazole, leur preparation et leur utilisation en therapeutique |
Publications (2)
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| JP2005500370A true JP2005500370A (ja) | 2005-01-06 |
| JP2005500370A5 JP2005500370A5 (enExample) | 2006-01-05 |
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| JP2003519045A Pending JP2005500370A (ja) | 2001-08-06 | 2002-08-05 | アクリルアミノチアゾール誘導体、それらの製造および治療的使用 |
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| Country | Link |
|---|---|
| US (2) | US7288659B2 (enExample) |
| EP (1) | EP1417189B1 (enExample) |
| JP (1) | JP2005500370A (enExample) |
| AR (1) | AR039059A1 (enExample) |
| AT (1) | ATE312828T1 (enExample) |
| DE (1) | DE60208044T2 (enExample) |
| DK (1) | DK1417189T3 (enExample) |
| ES (1) | ES2254773T3 (enExample) |
| TW (1) | TWI318974B (enExample) |
| WO (1) | WO2003014095A1 (enExample) |
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|---|---|---|---|---|
| AR038703A1 (es) | 2002-02-28 | 2005-01-26 | Novartis Ag | Derivados de 5-feniltiazol y uso como inhibidor de quinasa p i 3 |
| OA12937A (en) * | 2002-10-09 | 2006-10-13 | Pfizer Prod Inc | Thiazole compounds for the treatment of neurodegenerative disorders. |
| FR2850380B1 (fr) * | 2003-01-23 | 2006-07-07 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur utilisation en therapeutique |
| MXPA05012196A (es) * | 2003-05-12 | 2006-02-08 | Pfizer Prod Inc | Compuestos de isoxazol e isotiazol para el tratamiento de trastornos neurodegenerativos. |
| MXPA06001480A (es) * | 2003-08-06 | 2006-05-15 | Pfizer Prod Inc | Compuestos de oxazol para el tratamiento de trastornos neurodegenerativos. |
| FR2873374B1 (fr) * | 2004-07-22 | 2006-10-20 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur application en therapeutique |
| EP1709018B1 (fr) | 2004-01-16 | 2011-07-20 | Sanofi-Aventis | Derives d'acylaminothiazole et leur application comme inhibiteurs de beta-amyloide |
| FR2865207B1 (fr) * | 2004-01-16 | 2008-10-17 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur application en therapeutique |
| FR2865206B1 (fr) * | 2004-01-16 | 2009-02-06 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur application en therapeutique |
| AU2005209442B2 (en) * | 2004-01-16 | 2011-03-31 | Sanofi-Aventis | Acylaminothiazole derivatives, preparation method thereof and use of same in therapeutics |
| US7220865B2 (en) * | 2004-04-01 | 2007-05-22 | Pfizer Inc | Isoxazole-and isothiazole-amine compounds for the treatment of neurodegenerative disorders |
| US7232820B2 (en) * | 2004-04-01 | 2007-06-19 | Pfizer Inc | Thiadiazole-amine compounds for the treatment of neurodegenerative disorders |
| AU2007207743B2 (en) * | 2006-01-18 | 2010-07-08 | Amgen Inc. | Thiazole compounds as protein kinase B (PKB) inhibitors |
| US7897619B2 (en) | 2007-07-17 | 2011-03-01 | Amgen Inc. | Heterocyclic modulators of PKB |
| US7919504B2 (en) | 2007-07-17 | 2011-04-05 | Amgen Inc. | Thiadiazole modulators of PKB |
| WO2017173048A1 (en) * | 2016-03-31 | 2017-10-05 | Merck Patent Gmbh | Compounds for the inhibition of cyclophilins and uses thereof |
| US11530211B2 (en) | 2018-01-18 | 2022-12-20 | Daiichi Sankyo Company, Limited | Dihydroindolizinone derivative |
| CN114040966A (zh) | 2019-07-08 | 2022-02-11 | 国立大学法人东京工业大学 | 使用了二氢吲嗪酮衍生物的胰岛素生产细胞的制作法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR016751A1 (es) * | 1996-11-22 | 2001-08-01 | Athena Neurosciences Inc | Metodo para inhibir la liberacion del peptido beta-amiloide en una celula, composicion farmaceutica y compuestos utiles en dicho metodo |
| ID22499A (id) | 1996-11-22 | 1999-10-21 | Elan Pharmaceuticals Inc Cs | Amida-amida asam n-(aril/heteroaril/alkilasetil) amino, komposisi farmasi yang terdiri dari amida asam amino tersebut, dan metode untuk menghambat pelepasan b-amiloid peptida dan/atau pembuatannya dengan menggunakan senyawa-senyawa tersebut |
| ZA9711537B (en) * | 1996-12-23 | 1998-06-25 | Athena Neurosciences Inc Eli L | Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting ß-amyloid peptide release and/or its synthesis by use of such compounds. |
| HRP980093A2 (en) * | 1997-02-28 | 1998-12-31 | Lilly Co Eli | Heterocyclic compounds, pharmaceutical compositions comprising same, and methods for inhibiting "beta"-amyloid peptide release and/or its synthesis by use of such compounds |
| AU6278099A (en) | 1998-09-30 | 2000-04-17 | Elan Pharmaceuticals, Inc. | Biological reagents and methods for determining the mechanism in the generation of beta-amyloid peptide |
| WO2000024392A1 (en) | 1998-10-26 | 2000-05-04 | Sumitomo Pharmaceuticals Company, Limited | β-AMYLOID FORMATION INHIBITORS |
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2002
- 2002-08-02 AR ARP020102935A patent/AR039059A1/es active IP Right Grant
- 2002-08-05 TW TW091117569A patent/TWI318974B/zh not_active IP Right Cessation
- 2002-08-05 JP JP2003519045A patent/JP2005500370A/ja active Pending
- 2002-08-05 EP EP02794623A patent/EP1417189B1/fr not_active Expired - Lifetime
- 2002-08-05 US US10/485,837 patent/US7288659B2/en not_active Expired - Lifetime
- 2002-08-05 DK DK02794623T patent/DK1417189T3/da active
- 2002-08-05 DE DE60208044T patent/DE60208044T2/de not_active Expired - Lifetime
- 2002-08-05 WO PCT/FR2002/002802 patent/WO2003014095A1/fr not_active Ceased
- 2002-08-05 ES ES02794623T patent/ES2254773T3/es not_active Expired - Lifetime
- 2002-08-05 AT AT02794623T patent/ATE312828T1/de active
-
2007
- 2007-09-20 US US11/858,454 patent/US20080058380A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE60208044T2 (de) | 2006-08-17 |
| TWI318974B (en) | 2010-01-01 |
| DK1417189T3 (da) | 2006-05-08 |
| WO2003014095A1 (fr) | 2003-02-20 |
| EP1417189A1 (fr) | 2004-05-12 |
| US20040171643A1 (en) | 2004-09-02 |
| US7288659B2 (en) | 2007-10-30 |
| ATE312828T1 (de) | 2005-12-15 |
| ES2254773T3 (es) | 2006-06-16 |
| AR039059A1 (es) | 2005-02-09 |
| DE60208044D1 (de) | 2006-01-19 |
| US20080058380A1 (en) | 2008-03-06 |
| EP1417189B1 (fr) | 2005-12-14 |
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