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【结 构 式】

【药物名称】Cimicoxib, UR-8880

【化学名称】4-[4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide

【CA登记号】265114-23-6

【 分 子 式 】C16H13ClFN3O3S

【 分 子 量 】381.81571

【开发单位】Uriach (Originator)

【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antiarthritic Drugs, Non-Opioid Analgesics, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Cyclooxygenase-2 Inhibitors

合成路线1

Treatment of 4-(acetylamino)phenylsulfonyl chloride (I) with tert-butylamine yields sulfonamide (II), which on deprotection with potassium hydroxide gives amine (III). Reaction of compound (III) with 4-methoxy-3-fluorobenz-aldehyde gives imine (IV), which is cyclized with tosylmethyl isocyanide to afford imidazole (V). Regioselective chlorination of compound (V) with N-chlorosuccinimide (NCS) to afford the chloroimidazole (VI) and then deprotection of the sulfonamide group of (VI) yields cimicoxib in 40% overall yield.

1 Almansa, C.; Torres, M.C.; Gonzalez, C. (J. Uriach & Cia., SA); Novel imidazoles with anti-inflammatory activity. EP 1122243; JP 2002527508; WO 0023426 .
2 Almansa Rosales, C.; Gonzales Gonzales, C. (J. Uriach & Cia., SA); Method of preparing 4-(imidazol-1-yl)benzenesulphonamide derivs.. ES 2184633; WO 0316285 .
3 Sorbera, L.A., Ramis, I.; Cimicoxib. Drugs Fut 2004, 29 (4): 325.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
65184 3-fluoro-4-methoxybenzaldehyde 351-54-2 C8H7FO2 详情 详情
(I) 19362 4-(acetamido)benzenesulfonyl chloride; N-acetylsulfanilyl chloride 121-60-8 C8H8ClNO3S 详情 详情
(II) 65182 N-{4-[(tert-butylamino)sulfonyl]phenyl}acetamide C12H18N2O3S 详情 详情
(III) 65183 4-amino-N-(tert-butyl)benzenesulfonamide 209917-48-6 C10H16N2O2S 详情 详情
(IV) 65185 N-(tert-butyl)-4-{[(Z)-(3-fluoro-4-methoxyphenyl)methylidene]amino}benzenesulfonamide C18H21FN2O3S 详情 详情
(V) 65186 N-(tert-butyl)-4-[5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide C20H22FN3O3S 详情 详情
(VI) 65187 N-(tert-butyl)-4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide C20H21ClFN3O3S 详情 详情
Extended Information