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【结 构 式】 
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【药物名称】Deprodone propionate, Eclar 【化学名称】(+)-11beta,17-Dihydroxy-1,4-pregnadiene-3,20-dione-17-propionate 【CA登记号】20424-00-4 【 分 子 式 】C24H32O5 【 分 子 量 】400.51964 |
【开发单位】Abbott (Originator), SSP (Licensee), Teikoku Seiyaku (Licensee) 【药理作用】Antiinflammatory Drugs, Corticosteroids |
合成路线1
This compound can be obtained by two different ways: 1) The oxidation of 21-desoxyprednisolone (I) with chromium trioxide and manganous nitrate in acetic acid gives 21-desoxyprednisone (II), which is esterified with propionic anhydride and p-toluenesulfonic acid yielding 21-desoxy-17-O-propionylprednisone (III). Finally, this compound is reduced with KBH4 in DMF - water. 2) The esterification of 21-O-(methanesulfonyl)prednisolone (IV) with acetyl nitrate in acetic acid gives 21-O-(methanesulfonyl)-11-O-nitroprednisolone (V), which is treated with NaI and NaHSO3 in acetic acid yielding the corresponding 21-desoxy nitrate ester (VI). The esterification of (VI) with propionic anhydride as before affords 21-desoxy-11-O-nitro-17-O-propionylprednisolone (VII), which is finally denitrated with Zn powder in acetic acid.
| 【1】 Oxley, P.; Housley, J.T. (The Boots Company plc); 17-Acyloxysteroids and their manufacture. US 3639434 . |
| 【2】 Oxley, P.; Housley, J.T. (The Boots Company plc); 17-Acyloxysteroids and their manufacture. US 3856956 . |
| 【3】 Housley, J.R.; Oxley, P. (The Boots Company plc); Improvements in acylated steroids. GB 1159490 . |
| 【4】 Housley, J.R.; Oxley, P. (The Boots Company plc); Improvements in acylated steroids. FR 1513708; GB 1158492 . |
| 【5】 Prous, J.; Castaner, J.; Deprodone Propionate. Drugs Fut 1991, 16, 9, 801. |
| 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) | 14171 | (8S,9S,10R,11S,13S,14S,17R)-17-Acetyl-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 | C21H28O4 | 详情 | 详情 | |
| (II) | 14172 | (8S,9S,10R,13S,14S,17R)-17-Acetyl-17-hydroxy-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-3,11(6H)-dione | C21H26O4 | 详情 | 详情 | |
| (III) | 14173 | (8S,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate | C24H30O5 | 详情 | 详情 | |
| (IV) | 14174 | 2-[(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]phenanthren-17-yl]-2-oxoethyl methanesulfonate | 35410-28-7 | C22H30O7S | 详情 | 详情 |
| (V) | 14175 | 2-[(8S,9S,10R,11S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-11-(nitrooxy)-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl methanesulfonate | C22H29NO9S | 详情 | 详情 | |
| (VI) | 14176 | (8S,9S,10R,11S,13S,14S,17R)-17-Acetyl-17-hydroxy-10,13-dimethyl-11-(nitrooxy)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | C21H27NO6 | 详情 | 详情 | |
| (VII) | 14177 | (8S,9S,10R,11S,13S,14S,17R)-17-acetyl-10,13-dimethyl-11-(nitrooxy)-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate | C24H31NO7 | 详情 | 详情 |