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Celecoxib, YM-177, SC-58635, Onsenal, Solexa, Celebrex, Celebra
塞来昔布Chemical Name: 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
CAS No. 169590-42-5
项目整合开发状态: Launched-1999
项目研究机构: Pfizer (Orphan Drug), Pfizer (Originator), National Cancer Institute (Not Determined), National Cancer Institute of Canada (Not Determined), National Institutes of Health (Not Determined), Pfizer (Licensee), Yamanouchi (Licensee), National Cancer Institut
合成路线:The condensation of 4-methylacetophenone (I) with ethyl trifluoroacetate (II) by means of NaOMe in refluxing methanol gives 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione,which is cyclized with 4-hydrazinophenylsulfonamide (III) in refluxing ethanol.
📌 参考资料/链接：
参考文献标题:Substd.pyrazolyl benzenesulfonamides for the treatment of inflammation
文献作者:Talley,J.J.; Penning,T.D.; Collins,P.W.; Rogier,D.J.Jr.; Malecha,J.W.; Miyashiro,J.M.; Bertenshaw,S.R.; Khanna,I.K.; Granets,M.J.; Rogers,R.S.; Carter,J.S.; Docter,S.H.; Yu,S.S.(Pharmacia Corp.)
参考来源:EP 0731795; EP 0922697; EP 0924201; JP 1997506350; JP 2000109466; US 5521207; WO 9515316
📄 详细内容
合成路线:The condensation of 4-methylacetophenone (I) with ethyl trifluoroacetate (II) by means of NaOMe in refluxing methanol gives 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione,which is cyclized with 4-hydrazinophenylsulfonamide (III) in refluxing ethanol.
参考文献标题:Method of preparing 3-haloalkyl-1H-pyrazoles
文献作者:Zhi,B.; Newaz,M.; Talley,J.J.; Bertenshaw,S.(Pharmacia Corp.)
参考来源:WO 9637476
合成路线:The condensation of 4-methylacetophenone (I) with ethyl trifluoroacetate (II) by means of NaOMe in refluxing methanol gives 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione,which is cyclized with 4-hydrazinophenylsulfonamide (III) in refluxing ethanol.
参考文献标题:Celecoxib
文献作者:Graul,A.; Martel,A.M.; Castar,J.
参考来源:Drugs Fut 1997,22(7),711
合成路线:Claisen condensation of 4'-chloroacetophenone (I) with ethyl trifluoroacetate in the presence of NaOMe provided diketone (II).Subsequent reaction of (II) with 4-sulfamoylphenylhydrazine (III) provided the title 1,5-diaryl pyrazole along with minor amounts of the 1,3-diaryl regioisomer,which was removed by recrystallization from EtOAc and isooctane.
合成路线:The condensation of 4-methylacetophenone (I) with ethyl trifluoroacetate (II) by means of NaOMe in refluxing methanol gives 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione,which is cyclized with 4-hydrazinophenylsulfonamide (III) in refluxing ethanol.
参考文献标题:Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635,celecoxib)
文献作者:Penning,T.D.; Bertenshaw,S.R.; Talley,J.J.; Carter,J.S.; Collins,P.W.; Docter,S.; Graneto,M.J.; Lee,L.F.; Malecha,J.W.; Miyashiro,J.M.; Rogers,R.S.; Rogier,D.J.; Yu,S.S.; Anderson,G.D.; Burton,E.G.; Cogburn,J.N.; Gregory,S.A.; et al.
参考来源:J Med Chem 1997,40(9),1347
产品链接: CAS No. 169590-42-5››