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【结 构 式】 
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【药物名称】Methylprednisolone aceponate, SH-440, ZK-91588, Adventan, Advantan 【化学名称】(6alpha,11beta)-21-Acetoxy-11-hydroxy-6-methyl-17-(propionyloxy)pregna-1,4-diene-3,20-dione 【CA登记号】86401-95-8 【 分 子 式 】C27H36O7 【 分 子 量 】472.58377 |
【开发单位】Leiras (Originator), Schering AG (Originator) 【药理作用】Atopic Dermatitis, Agents for, Dermatologic Drugs, Eczema, Treatment of, Topical Antiinflammatory Agents, Antiinflammatory Drugs, Corticosteroids |
合成路线1
The esterification of 11beta,17alpha,21-trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione (I) with triethyl orthopropionate (II) by means of pyridinium tosylate in DMF - benzene gives the corresponding cyclic diester (III), which is partially hydrolyzed with acetic acid - sodium acetate in methanol - water, yielding the 17alpha-propionyloxy derivative (IV). Finally, this compound is acetylated with acetic anhydride and pyridine.
| 【1】 Annen, K.; Petzoldt, K.; Laurent, H.; Wiechert, R.; Hofmeister, H.; Wendt, H. (Schering AG); New 6alpha-methylprednisolone derivs. their preparation and use. EP 0072547 . |
| 【2】 Naito, Y.; Sugai, S.; Kanbara, T.; Yoshida, S.; Akaboshi, S.; Ikegami, S.; Kamano, Y.; Okazaki, T:, Kajiwara, Y.; Studies on topical antiinflammatory corticosteroids. I. Syntheses and vasoconstrictive activities of 11beta,17alpha,21-trihydroxy-6alpha-methyl-1,4-pregnadiene-3,20-dione 17-ester and 17,21-diester derivatives. Chem Pharm Bull 1985, 33, 5, 1889. |
| 【3】 Prous, J.; Castaner, J.; Methylprednisolone Aceponate. Drugs Fut 1993, 18, 2, 130. |
| 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) | 10394 | Methylprednisolone | 83-43-2 | C22H30O5 | 详情 | 详情 |
| (II) | 10395 | 1,1,1-Triethoxypropane; 1,1-Diethoxypropyl ethyl ether; Triethyl orthopropionate | 115-80-0 | C9H20O3 | 详情 | 详情 |
| (III) | 10396 | 2'-Ethoxy-2'-ethyl-11-beta-hydroxy-6-alpha-methylspiro[gona-1,4-diene-17(R),4'-1,3-dioxane]3,5'-dione | C27H38O6 | 详情 | 详情 | |
| (IV) | 10397 | (6S,8S,9S,10R,11S,13S,14S,17R)-17-glycoloyl-11-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate | C25H34O6 | 详情 | 详情 |