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【结 构 式】 
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【药物名称】Prednisolone sodium metasulfobenzoate, ATL-2502, Predocol, Predecol, Colal-Pred 【化学名称】11beta,17-Dihydroxy-21-(3-sulfobenzoyloxy)pregna-1,4-diene-3,20-dione sodium salt 【CA登记号】630-67-1 【 分 子 式 】C28H31NaO9S 【 分 子 量 】566.60767 |
【开发单位】Alizyme (Originator) 【药理作用】GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for |
合成路线1
The title compound is prepared by two alternative methods. Sulfonation of benzoic acid (I) with hot chlorosulfonic acid affords 3-carboxybenzenesulfonyl chloride (II). After conversion of (II) to the pyridine complex, coupling with prednisolone (III) produces the target 21-sulfobenzoate ester, which is finally isolated as the title sodium salt by treatment with aqueous NaOH.
| 【1】 Girault, P.; Allais, A. (Aventis Pharma SA); Process for the preparation of 21-m-sulfo benzoates of DELTA1,4-dehydrocorticosteroids. US 3032568 . |
| 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) | 10202 | Benzoic acid | 65-85-0 | C7H6O2 | 详情 | 详情 |
| (II) | 59291 | 3-(Chlorosulfonyl)benzoic acid; m-(Chlorosulfonyl)benzoic acid | 4025-64-3 | C7H5ClO4S | 详情 | 详情 |
| (III) | 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 |
合成路线2
Alternatively, the title compound is prepared by condensation of prednisolone 21-methanesulfonate (I) with sodium 3-sulfobenzoate (II) in DMF/H2O, followed by conversion to the corresponding sodium salt with aqueous sodium acetate.
| 【1】 Joly, R.; Warnant, J. (Aventis Pharma SA); Novel process for the preparation of 21-esters of 20-keto-steroids. FR 1344153; US 3037034 . |