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【结 构 式】 
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【药物名称】Bromfenac sodium, AHR-10282B, AHR-10282(anhydrous), Xibrom, Bronuck, Duract 【化学名称】2-[2-Amino-3-(4-bromobenzoyl)phenyl]acetic acid monosodium salt sesquihydrate 【CA登记号】120638-55-3, 91714-93-1 (anhydrous), 91714-94-2 (anhydrous;free acid) 【 分 子 式 】C15H13BrNNaO4 【 分 子 量 】374.16896 |
【开发单位】Wyeth Pharmaceuticals (Originator), GlaxoSmithKline (Licensee), ISTA Pharmaceuticals (Licensee), Senju (Licensee) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antiinflammatory Ophthalmic Agents, Ocular Antiinflammatory and Antiinfective Agents, OCULAR MEDICATIONS, Ophthalmic Drugs, Non-Steroidal Antiinflammatory Drugs |
合成路线1
The cyclization of 2-amino-4'-bromobenzophenone (I) with ethyl 2-(methylthio)acetate (II) by means of tert-butyl hypochlorite in dichloromethane at 70 C gives 7-(4-bromobenzoyl)-3-(methylthio)-2,3-dihydro-1H-indol-2-one (III), which is desulfurized by a treatment with Raney Nickel in THF yielding 7-(4-bromobenzoyl)-2,3-dihydro-1H-indol-2-one (IV). Finally, this compound is hydrolyzed with refluxing 3N NaOH and acidified with concentrated HCl.
| 【1】 Moran, H.W.; Welstead, W.J. Jr. (A.H. Robins Co. Inc.); 2-Aminophenylacetic acid derivs.. US 4126635 . |
| 【2】 Prous, J.; Castaner, J.; BROMFENAC SODIUM < Rec INNM; USAN >. Drugs Fut 1988, 13, 11, 943. |
| 【3】 Walsh, D.A.; Moran, H.W.; Shamblee, D.A.; Uwaydah, I.M.; Welstead, W.J. Jr.; Sancilio, L.F.; Dannenburg, W.N.; Anti-inflammatory agents. 3. Synthesis and pharmac. J Med Chem 1984, 27, 11, 1379-88. |
| 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) | 23396 | (2-aminophenyl)(4-bromophenyl)methanone | C13H10BrNO | 详情 | 详情 | |
| (II) | 48543 | Ethyl methylthioacetate; (Methylthio)acetic acid ethyl ester; ethyl 2-(methylsulfanyl)acetate | 4455-13-4 | C5H10O2S | 详情 | 详情 |
| (III) | 23398 | 7-(4-bromobenzoyl)-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one | C16H12BrNO2S | 详情 | 详情 | |
| (IV) | 23399 | 7-(4-bromobenzoyl)-1,3-dihydro-2H-indol-2-one | C15H10BrNO2 | 详情 | 详情 |