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Deprodone propionate, Eclar

丙酸地泼罗酮Chemical Name: (+)-11beta,17-Dihydroxy-1,4-pregnadiene-3,20-dione-17-propionate; (+)-11beta-Hydroxy-17-(propionyloxy)pregna-1,4-diene-3,20-dione; (+)-21-Desoxyprednisolone 17alpha-propionate
CAS No. 20424-00-4
项目整合开发状态: Launched-1992
项目研究机构: Abbott (Originator), SSP (Licensee), Teikoku Seiyaku (Licensee)
合成路线: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.
📌 参考资料/链接:
参考文献标题:Improvements in acylated steroids
文献作者:Housley,J.R.; Oxley,P.(The Boots Company plc)
参考来源:FR 1513708; GB 1158492

📄 详细内容


合成路线: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.

参考文献标题:Improvements in acylated steroids
文献作者:Housley,J.R.; Oxley,P.(The Boots Company plc)
参考来源:GB 1159490


合成路线: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.

参考文献标题:17-Acyloxysteroids and their manufacture
文献作者:Oxley,P.; Housley,J.T.(The Boots Company plc)
参考来源:US 3639434


合成路线: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.

参考文献标题:17-Acyloxysteroids and their manufacture
文献作者:Oxley,P.; Housley,J.T.(The Boots Company plc)
参考来源:US 3856956


合成路线: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.
参考文献标题:Deprodone Propionate
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1991,16(9),801


产品链接: CAS No. 20424-00-4››