DE60221977T2 - Pro-pharmakon von cox-2-inhibitoren - Google Patents
Pro-pharmakon von cox-2-inhibitoren Download PDFInfo
- Publication number
- DE60221977T2 DE60221977T2 DE60221977T DE60221977T DE60221977T2 DE 60221977 T2 DE60221977 T2 DE 60221977T2 DE 60221977 T DE60221977 T DE 60221977T DE 60221977 T DE60221977 T DE 60221977T DE 60221977 T2 DE60221977 T2 DE 60221977T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- pharmaceutically acceptable
- compounds
- methylphenyl
- trifluoromethyl
- 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 - Fee Related
Links
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title description 16
- 229940111134 coxibs Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 37
- -1 5-methyl-3-phenylisoxazol-4-yl Chemical group 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 32
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 15
- 206010061218 Inflammation Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 230000004054 inflammatory process Effects 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- VOHWHIJGUFVMCO-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 VOHWHIJGUFVMCO-UHFFFAOYSA-N 0.000 claims description 7
- NCYZWCLZAPERAN-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(=O)(=O)NCCO)C=C1 NCYZWCLZAPERAN-UHFFFAOYSA-N 0.000 claims description 7
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 5
- YRAUNLSKYHHJIH-UHFFFAOYSA-N n-ethyl-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)N(C(=O)CC)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 YRAUNLSKYHHJIH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
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- 238000000034 method Methods 0.000 description 41
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
- 230000008569 process Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical group 0.000 description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 8
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- 238000003786 synthesis reaction Methods 0.000 description 8
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- 238000002425 crystallisation Methods 0.000 description 7
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
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Applications Claiming Priority (5)
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| US28458901P | 2001-04-17 | 2001-04-17 | |
| US284589P | 2001-04-17 | ||
| US35795902P | 2002-02-19 | 2002-02-19 | |
| US357959P | 2002-02-19 | ||
| PCT/US2002/012013 WO2002083655A1 (en) | 2001-04-17 | 2002-04-17 | Prodrugs of cox-2 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60221977D1 DE60221977D1 (de) | 2007-10-04 |
| DE60221977T2 true DE60221977T2 (de) | 2008-05-15 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| DE60221977T Expired - Fee Related DE60221977T2 (de) | 2001-04-17 | 2002-04-17 | Pro-pharmakon von cox-2-inhibitoren |
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| MX (1) | MXPA03009410A (enExample) |
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| PE (1) | PE20021108A1 (enExample) |
| PL (1) | PL367180A1 (enExample) |
| WO (2) | WO2002102376A1 (enExample) |
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2002
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- 2002-04-12 WO PCT/US2002/011690 patent/WO2002102376A1/en not_active Ceased
- 2002-04-12 IL IL15820002A patent/IL158200A0/xx unknown
- 2002-04-12 EP EP02723846A patent/EP1494666A1/en not_active Withdrawn
- 2002-04-12 JP JP2003504963A patent/JP2004529986A/ja not_active Withdrawn
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- 2002-04-12 EA EA200301018A patent/EA006677B1/ru not_active IP Right Cessation
- 2002-04-12 PL PL02367180A patent/PL367180A1/xx not_active Application Discontinuation
- 2002-04-12 CN CNB028120523A patent/CN1292746C/zh not_active Expired - Fee Related
- 2002-04-12 BR BR0208947-5A patent/BR0208947A/pt not_active IP Right Cessation
- 2002-04-12 CA CA002444356A patent/CA2444356A1/en not_active Abandoned
- 2002-04-12 AU AU2002254609A patent/AU2002254609B2/en not_active Ceased
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- 2002-04-12 KR KR10-2003-7013653A patent/KR20040012761A/ko not_active Ceased
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- 2002-04-16 US US10/123,730 patent/US6613790B2/en not_active Expired - Fee Related
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- 2002-04-17 WO PCT/US2002/012013 patent/WO2002083655A1/en not_active Ceased
- 2002-04-17 EP EP02762127A patent/EP1379513B1/en not_active Expired - Lifetime
- 2002-04-17 JP JP2002581411A patent/JP2004526765A/ja not_active Withdrawn
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2004
- 2004-09-14 US US10/940,053 patent/US20050032852A1/en not_active Abandoned
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