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- W1990389008 abstract "It is generally accepted that the anti-inflammatory effect of glucocorticosteroids cannot be separated from their adverse effects at the receptor level. However, modification of the pharmacokinetics through structural alterations could provide steroids with a better therapeutic index than those currently used. Thus, new 16α,17α-acetals between butyraldehyde and 6α-fluoro- or 6α,9α-difluoro-16α-hydroxycortisol were synthesized and studied. Acetalization of the corresponding 16α,17α-diols or transacetalization of their 16α,17α-acetonides in dioxane produced mixtures of C-22 epimers, which were resolved by preparative chromatography. Alternatively, an efficient method was used to produce the 22R-epimer stereoselectively through performing the acetalization and transacetalization in a hydrocarbon with an inert material present. The C-22 configuration of (22R)-6α,9α-difluoro-11β,21-dihydroxy-16α,17α-propylmethylenedioxypregn-4-ene-3,20-dione was unambiguously established by single crystal X-ray diffraction. The present compounds, especially the 22R-epimer just mentioned, bind to the rat thymus glucocorticoid receptor with high potency. The C-22 epimers of the 6α,9α-difluoro derivatives showed a 10-fold higher biotransformation rate than the budesonide 22R-epimer when incubated with human liver S9 subcellular fraction. The high receptor affinity in combination with the high biotransformation rate indicates that (22R)-6α,9α-difluoro-11β,21-dihydroxy-16α,17α-propylmethylenedioxypregn-4-ene-3,20-dione may be an improved 16α,17α-acetal glucocorticosteroid for therapy of inflammatory diseases, in which the mucous membranes are involved, such as those in the intestinal tract as well in the respiratory tract." @default.
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- W1990389008 date "1998-01-01" @default.
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- W1990389008 title "6α-Fluoro- and 6α,9α-difluoro-11β,21- dihydroxy-16α,17α-propylmethylenedioxypregn-4-ene-3,20-dione: Synthesis and evaluation of activity and kinetics of their C-22 epimers" @default.
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- W1990389008 doi "https://doi.org/10.1016/s0039-128x(97)00107-4" @default.
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