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【结 构 式】 
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【药物名称】Loteprednol etabonate, IDR-90102(topical), IDR-90103(oral formulation), CDDD-5604, HGP-1, P-5604, Locort, Loterox, Alrex, Lotemax, Lenoxin 【化学名称】11beta,17-Dihydroxy-3-oxoandrosta-1,4-diene-17beta-carboxylic acid chloromethyl ester 17-(ethylcarbonate) 【CA登记号】82034-46-6, 129260-79-3 (loteprednol) 【 分 子 式 】C24H31ClO7 【 分 子 量 】466.96347 |
【开发单位】Bausch & Lomb (Proprietary), Soft Drugs (Originator), Ivax (Not Determined), Asta Medica (Licensee) 【药理作用】Antiallergic Ophthalmic Agents, Antiinflammatory Ophthalmic Agents, Asthma Therapy, Dermatologic Drugs, Drugs for Allergic Rhinitis, Ocular Antiinflammatory and Antiinfective Agents, OCULAR MEDICATIONS, Ophthalmic Drugs, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders, Corticosteroids |
合成路线1
The oxidation of 11beta,17,21-trihydroxypregnan-1,4-diene-3,20-dione (I) with sodium metaperiodate in THF/methanol gives 11beta,17alpha-dihydroxy-3-oxoandrosta-1,4-diene-17beta-carboxylic acid (II), which is treated with ethyl chloroformate and triethylamine in dichloromethane yielding 17alpha-(ethoxycarbonyloxy)-11beta-hydroxy-3-oxoandrosta-1,4-diene-17beta-carboxylic acid (III). Finally, this compound is esterified with chloromethyl iodide and NaOH in methanol/water.
| 【1】 Graul, A.; Martin, L.; Castaner, J.; Loteprednol Etabonate. Drugs Fut 1997, 22, 10, 1086. |
| 【2】 Bodor, N.S. (N.S. Bodor); Steroids with antiinflammatory activity. BE 0889563; US 4996335 . |
| 【3】 Druzgala, P.; Hochhaus, G.; Bodor, N.; Soft drugs - 10. Blanching activity and receptor binding affinity of a new type of glucocorticoid: Loteprednol etabonate. J Steroid Biochem Mol Biol 1991, 38, 2, 149-154. |
| 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) | 14613 | (8S,9S,10R,11S,13S,14S,17R)-17-[(ethoxycarbonyl)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 | C23H30O7 | 详情 | 详情 |