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【结 构 式】 
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【药物名称】 【化学名称】6alpha,9-Difluoro-11beta-hydroxy-16alpha,17-(isopropylidenedioxy)-21-(2-oxotetrahydrofuran-3-ylsulfanyl)pregna-1,4-diene-3,20-dione 【CA登记号】193408-35-4 ((R)-isomer), 193408-36-5 ((S)-isomer) 【 分 子 式 】C28H34F2O7S 【 分 子 量 】552.63978 |
【开发单位】GlaxoSmithKline (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Glucocorticoid Receptor Agonists |
合成路线1
Fluocinolone acetonide (I) was selectively mesylated at the primary alcohol group by means of methanesulfonyl chloride and pyridine. Treatment of the resulting mesylate (II) with alpha-mercapto-gamma-butyrolactone (IV) in the presence of NaH in THF produced the desired thioether derivative.
| 【1】 Burgess, C.M.; Biggadike, K.; Angell, R.M.; et al.; Selective plasma hydrolysis of glucocorticoid gamma-lactones and cyclic carbonates by the enzyme paraoxonase: An ideal plasma inactivation mechanism. J Med Chem 2000, 43, 1, 19. |
| 【2】 Farrell, R.M.; Biggadike, K. (Glaxo Wellcome Inc.); 21-(2-Oxo-tetrahydrofuran)-thio pregnane derivs., a process for their production and pharmaceutical compsns. containing them. US 6013244; WO 9724367 . |
| 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) | 46292 | (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one | C24H30F2O6 | 详情 | 详情 | |
| (II) | 46293 | 2-[(4aS,4bR,5S,6aS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6-yl]-2-oxoethyl methanesulfonate | C25H32F2O8S | 详情 | 详情 | |
| (III) | 46294 | 3-sulfanyldihydro-2(3H)-furanone | C4H6O2S | 详情 | 详情 |
Extended Information