DE60208044T2 - Acylaminothiazolderivate, deren herstellung und deren therapeutische verwendung - Google Patents
Acylaminothiazolderivate, deren herstellung und deren therapeutische verwendung Download PDFInfo
- Publication number
- DE60208044T2 DE60208044T2 DE60208044T DE60208044T DE60208044T2 DE 60208044 T2 DE60208044 T2 DE 60208044T2 DE 60208044 T DE60208044 T DE 60208044T DE 60208044 T DE60208044 T DE 60208044T DE 60208044 T2 DE60208044 T2 DE 60208044T2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- group
- methyl
- amino
- thiazol
- 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.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000001225 therapeutic effect Effects 0.000 title claims description 5
- -1 methylenedioxy Chemical group 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 230000007170 pathology Effects 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- 201000010374 Down Syndrome Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010039966 Senile dementia Diseases 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000008901 benefit Effects 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 38
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 36
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 30
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 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
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 26
- 239000000243 solution Substances 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- 108090000765 processed proteins & peptides Proteins 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
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- 125000006239 protecting group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 5
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- 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
- 108010043324 Amyloid Precursor Protein Secretases Proteins 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
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229940080818 propionamide Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 3
- MURVUTUZSUEIGI-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(Br)C(CBr)=C1 MURVUTUZSUEIGI-UHFFFAOYSA-N 0.000 description 3
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 3
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 3
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 3
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 3
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 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 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 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
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- HEVVOFBKIOYHHQ-AWEZNQCLSA-N (2s)-2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[2-(ethoxymethyl)phenyl]-1,3-thiazol-2-yl]propanamide Chemical compound CCOCC1=CC=CC=C1C(S1)=CN=C1NC(=O)[C@H](C)NC(=O)CC1=CC(F)=CC(F)=C1 HEVVOFBKIOYHHQ-AWEZNQCLSA-N 0.000 description 2
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- HEVVOFBKIOYHHQ-UHFFFAOYSA-N 2-[[2-(3,5-difluorophenyl)acetyl]amino]-n-[5-[2-(ethoxymethyl)phenyl]-1,3-thiazol-2-yl]propanamide Chemical compound CCOCC1=CC=CC=C1C(S1)=CN=C1NC(=O)C(C)NC(=O)CC1=CC(F)=CC(F)=C1 HEVVOFBKIOYHHQ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- 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
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- 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
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- 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)
- Public Health (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0110504 | 2001-08-06 | ||
| FR0110504 | 2001-08-06 | ||
| FR0207222A FR2840899B1 (fr) | 2002-06-12 | 2002-06-12 | Derives d'acylaminothiazole, leur preparation et leur utilisation en therapeutique |
| FR0207222 | 2002-06-12 | ||
| PCT/FR2002/002802 WO2003014095A1 (fr) | 2001-08-06 | 2002-08-05 | Derives d'acylaminothiazole, leur preparation et leur utilisation en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60208044D1 DE60208044D1 (de) | 2006-01-19 |
| DE60208044T2 true DE60208044T2 (de) | 2006-08-17 |
Family
ID=26213132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60208044T Expired - Lifetime DE60208044T2 (de) | 2001-08-06 | 2002-08-05 | Acylaminothiazolderivate, deren herstellung und deren therapeutische verwendung |
Country Status (10)
| 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) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY156407A (en) * | 2002-02-28 | 2016-02-26 | Novartis Ag | 5-phenylthiazole derivatives and use as p13 kinase inhibitors |
| BR0314611A (pt) * | 2002-10-09 | 2005-07-26 | Pfizer Prod Inc | Compostos de tiazol para o tratamento de distúrbios neurodegenerativos |
| FR2850380B1 (fr) * | 2003-01-23 | 2006-07-07 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur utilisation en therapeutique |
| WO2004099200A1 (en) * | 2003-05-12 | 2004-11-18 | Pfizer Products Inc. | Isoxazole and isothiazole compounds for the treatment of neurodegenerative disorders |
| 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 |
| FR2865206B1 (fr) * | 2004-01-16 | 2009-02-06 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur application en therapeutique |
| NZ548531A (en) * | 2004-01-16 | 2010-01-29 | Sanofi Aventis | Acylaminothiazole derivatives, preparation method thereof and use of same in therapeutics |
| FR2865207B1 (fr) * | 2004-01-16 | 2008-10-17 | Sanofi Synthelabo | Derives d'acylaminothiazole, leur preparation et leur application en therapeutique |
| JP4813371B2 (ja) * | 2004-01-16 | 2011-11-09 | サノフイ−アベンテイス | アシルアミノチアゾール誘導体及びβ−アミロイド阻害剤としてのこれらの使用 |
| 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 |
| EP1981884B1 (en) * | 2006-01-18 | 2012-06-13 | Amgen, Inc | Thiazole compounds as protein kinase b (pkb) inhibitors |
| AU2008276512A1 (en) * | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazole modulators of PKB |
| AU2008276521B2 (en) | 2007-07-17 | 2011-11-03 | Amgen Inc. | Heterocyclic modulators of PKB |
| EP3436448A1 (en) * | 2016-03-31 | 2019-02-06 | Merck Patent GmbH | Compounds for the inhibition of cyclophilins and uses thereof |
| CA3088968C (en) | 2018-01-18 | 2023-10-17 | 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 |
| NZ335280A (en) * | 1996-11-22 | 2001-05-25 | Lilly Co Eli | D-penicillamine derivatives for treating beta-amyloid type diseases such as Alzheimer's disease |
| HUP0001232A3 (en) * | 1996-12-23 | 2001-02-28 | Elan Pharmaceuticals Inc San F | Cycloalkyl, lactam, lactone derivatives and their thio analogues inhibiting betha-amyloid peptide release and/or its synthesis and pharmaceutical compositions containing the 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 |
| EP1131634A2 (en) * | 1998-09-30 | 2001-09-12 | Elan Pharmaceuticals, Inc. | Determining the mechanism of beta-amyloid peptide generation |
| AU6229699A (en) | 1998-10-26 | 2000-05-15 | Sumitomo Pharmaceuticals Company, Limited | Beta-amyloid formation inhibitors |
-
2002
- 2002-08-02 AR ARP020102935A patent/AR039059A1/es active IP Right Grant
- 2002-08-05 WO PCT/FR2002/002802 patent/WO2003014095A1/fr not_active Ceased
- 2002-08-05 US US10/485,837 patent/US7288659B2/en not_active Expired - Lifetime
- 2002-08-05 AT AT02794623T patent/ATE312828T1/de active
- 2002-08-05 EP EP02794623A patent/EP1417189B1/fr not_active Expired - Lifetime
- 2002-08-05 JP JP2003519045A patent/JP2005500370A/ja active Pending
- 2002-08-05 DK DK02794623T patent/DK1417189T3/da active
- 2002-08-05 DE DE60208044T patent/DE60208044T2/de not_active Expired - Lifetime
- 2002-08-05 ES ES02794623T patent/ES2254773T3/es not_active Expired - Lifetime
- 2002-08-05 TW TW091117569A patent/TWI318974B/zh not_active IP Right Cessation
-
2007
- 2007-09-20 US US11/858,454 patent/US20080058380A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TWI318974B (en) | 2010-01-01 |
| DK1417189T3 (da) | 2006-05-08 |
| JP2005500370A (ja) | 2005-01-06 |
| AR039059A1 (es) | 2005-02-09 |
| US7288659B2 (en) | 2007-10-30 |
| US20080058380A1 (en) | 2008-03-06 |
| EP1417189A1 (fr) | 2004-05-12 |
| DE60208044D1 (de) | 2006-01-19 |
| EP1417189B1 (fr) | 2005-12-14 |
| US20040171643A1 (en) | 2004-09-02 |
| ES2254773T3 (es) | 2006-06-16 |
| WO2003014095A1 (fr) | 2003-02-20 |
| ATE312828T1 (de) | 2005-12-15 |
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