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【结 构 式】 
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【药物名称】Celecoxib, YM-177, SC-58635, Onsenal, Solexa, Celebrex, Celebra 【化学名称】4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide 【CA登记号】169590-42-5 【 分 子 式 】C17H14F3N3O2S 【 分 子 量 】381.37923 |
【开发单位】Pfizer (Orphan Drug), Pfizer (Originator), National Institutes of Health (Not Determined), Pfizer (Licensee), Yamanouchi (Licensee), National Cancer Institute (Codevelopment) 【药理作用】Actinic Keratoses, Agents for, Adenomatous Polyposis Therapy, ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antiarthritic Drugs, Bladder Cancer Therapy , Brain Cancer Therapy, Breast Cancer Therapy, Colorectal Cancer Therapy, DERMATOLOGIC DRUGS, Head and Neck Cancer Therapy, Non-Opioid Analgesics, OCULAR MEDICATIONS, Oncolytic Drugs, Ophthalmic Drugs, Osteoarthritis, Treatment of, Rheumatoid Arthritis, Treatment of, Solid Tumors Therapy, Treatment of Age-Related Macular Degeneration, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Cyclooxygenase-2 Inhibitors, Non-Steroidal Antiinflammatory Drugs |
合成路线1
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.
| 【1】 Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; et al.; 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). J Med Chem 1997, 40, 9, 1347. |
| 【2】 Graul, A.; Martel, A.M.; Castañer, J.; Celecoxib. Drugs Fut 1997, 22, 7, 711. |
| 【3】 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.); Substd. pyrazolyl benzenesulfonamides for the treatment of inflammation. EP 0731795; EP 0922697; EP 0924201; JP 1997506350; JP 2000109466; US 5521207; WO 9515316 . |
| 【4】 Zhi, B.; Newaz, M.; Talley, J.J.; Bertenshaw, S. (Pharmacia Corp.); Method of preparing 3-haloalkyl-1H-pyrazoles. WO 9637476 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 17145 | 1-(4-methylphenyl)-1-ethanone; p-methylacetophenone; 4-methylacetophenone; 4-methylphenylethanone | 122-00-9 | C9H10O | 详情 | 详情 |
| (II) | 14588 | Ethyl 2,2,2-trifluoroacetate; Trifluoroethyl acetate | 383-63-1 | C4H5F3O2 | 详情 | 详情 |
| (III) | 17147 | 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione; 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione | 720-94-5 | C11H9F3O2 | 详情 | 详情 |
| (IV) | 17148 | 4-Hydrazinobenzenesulfonamide; 4-Sulfonamidophenylhydrazine | 4392-54-5 | C6H9N3O2S | 详情 | 详情 |