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【结 构 式】 
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【药物名称】Etiprednol dicloacetate, BNP-166, Respicort, Ethinase, Cronaze 【化学名称】(11beta,17alpha)-17-(2,2-Dichloroacetoxy)-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid ethyl ester 【CA登记号】199331-40-3 【 分 子 式 】C24H30Cl2O6 【 分 子 量 】485.4091 |
【开发单位】Ivax (Originator) 【药理作用】Asthma Therapy, Drugs for Allergic Rhinitis, GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders |
合成路线1
The oxidative cleavage of prednisolone (I) using sodium metaperiodate produces carboxylic acid (II). Regioselective esterification of diol (II) with dichloroacetyl chloride (III) under phase-transfer conditions gives the 17-ester (IV). The title ethyl ester is then obtained by esterification of (IV) with iodoethane in the presence of NaHCO3 and tetrabutylammonium hydrogensulfate.
| 【1】 Bodor, N.S. (Soft Drugs, Inc.); Androstene derivs.. WO 9742214 . |
| 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) | 13538 | (8S,9S,10R,11S,13S,14S,17R)-17-Glycoloyl-11,17-dihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one; Prednisolone | 50-24-8 | C21H28O5 | 详情 | 详情 |
| (II) | 14612 | (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid | C20H26O5 | 详情 | 详情 | |
| (III) | 17829 | 2,2-dichloroacetyl chloride; dichloroacetyl chloride | 79-36-7 | C2HCl3O | 详情 | 详情 |
| (IV) | 58347 | (8S,9S,10R,11S,13S,14S,17R)-17-[(2,2-dichloroacetyl)oxy]-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid | C22H26Cl2O6 | 详情 | 详情 |