【药物名称】Ulobetasol propionate, Halobetasol propionate, CGP-14458, BMY-30056, Miracorten, Ultravate
化学结构式(Chemical Structure):
参考文献No.13964
标题:Anner, G. (Ciba-Geigy AG). Polyhalogenated steroids
作者:Kalvoda, J.; Anner, G. (Novartis AG)
来源:CH 631185
合成路线图解说明:

The reaction of 21-chloro-9beta-11beta-epoxy-16beta-methyl-17-(propionyloxy)pregn-4-en-3,20-dione (I) with ethyl orthoformate and p-toluenesulfonic acid in ethanol - dioxane gives 21-chloro-9beta-11beta-epoxy-3-ethoxy-16beta-methyl-17-(propionyloxy)pregna-3,5-dien-20-one (II), which is treated with perchloryl fluoride (ClO3F) in THF - water, yielding 21-chloro-9beta,11beta-epoxy-6alpha-fluoro-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (III). The addition of HF to the epoxy ring of (III) by means of the complex urea - HF affords 21-chloro-6alpha,9alpha-difluoro-11beta-hydroxy-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (IV), which is finally dehydrogenated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in refluxing dioxane.

参考文献No.13972
标题:Process for the preparation of polyhalogenated steroids
作者:Kalvoda, J.; Anner, G. (Novartis AG)
来源:CH 632000; DE 2743069
合成路线图解说明:

The reaction of 21-chloro-9beta-11beta-epoxy-16beta-methyl-17-(propionyloxy)pregn-4-en-3,20-dione (I) with ethyl orthoformate and p-toluenesulfonic acid in ethanol - dioxane gives 21-chloro-9beta-11beta-epoxy-3-ethoxy-16beta-methyl-17-(propionyloxy)pregna-3,5-dien-20-one (II), which is treated with perchloryl fluoride (ClO3F) in THF - water, yielding 21-chloro-9beta,11beta-epoxy-6alpha-fluoro-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (III). The addition of HF to the epoxy ring of (III) by means of the complex urea - HF affords 21-chloro-6alpha,9alpha-difluoro-11beta-hydroxy-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (IV), which is finally dehydrogenated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in refluxing dioxane.

参考文献No.143256
标题:Halobetasol Propionate
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1991,16(7),614
合成路线图解说明:

The reaction of 21-chloro-9beta-11beta-epoxy-16beta-methyl-17-(propionyloxy)pregn-4-en-3,20-dione (I) with ethyl orthoformate and p-toluenesulfonic acid in ethanol - dioxane gives 21-chloro-9beta-11beta-epoxy-3-ethoxy-16beta-methyl-17-(propionyloxy)pregna-3,5-dien-20-one (II), which is treated with perchloryl fluoride (ClO3F) in THF - water, yielding 21-chloro-9beta,11beta-epoxy-6alpha-fluoro-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (III). The addition of HF to the epoxy ring of (III) by means of the complex urea - HF affords 21-chloro-6alpha,9alpha-difluoro-11beta-hydroxy-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (IV), which is finally dehydrogenated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in refluxing dioxane.

参考文献No.802272
标题:The effect of topically applied compound F in selected dermatoses
作者:Witten, V.H.; Sulzberger, M.B.
来源:J Invest Dermatol 1952,19101-2
合成路线图解说明:

The reaction of 21-chloro-9beta-11beta-epoxy-16beta-methyl-17-(propionyloxy)pregn-4-en-3,20-dione (I) with ethyl orthoformate and p-toluenesulfonic acid in ethanol - dioxane gives 21-chloro-9beta-11beta-epoxy-3-ethoxy-16beta-methyl-17-(propionyloxy)pregna-3,5-dien-20-one (II), which is treated with perchloryl fluoride (ClO3F) in THF - water, yielding 21-chloro-9beta,11beta-epoxy-6alpha-fluoro-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (III). The addition of HF to the epoxy ring of (III) by means of the complex urea - HF affords 21-chloro-6alpha,9alpha-difluoro-11beta-hydroxy-16beta-methyl-17-(propionyloxy)pregn-4-ene-3,20-dione (IV), which is finally dehydrogenated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in refluxing dioxane.

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