Potent soft anti-inflammatory corticosteroid compounds and uses thereof
AssigneeBodor Laboratories, Inc.
InventorNicholas S. Bodor
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Abstract
Potent soft corticosteroid pharmaceutical compositions comprising them and method for use as anti-inflammatory agents. Also, a method for softening fluticasone propionate and similar corticosteroids to arrive at potent but safer alternatives. The compound 5-fluoromethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate, which is equally potent to but safer than fluticasone, is among those provided. Another compound of particular interest is 2-hydroxyethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16β-methyl-3-oxoandrosta-1,4-diene-17β-carboxylate.
Claims16
A compound having the formula (I):
- wherein each X is independently F or Cl, and Y is S.
A process for softening a 17α-alkylcarbonyloxy-substituted corticosteroid compound of the formula (II)
- wherein each X is independently F or Cl, Y is S, and R is C1-C3 alkyl, said compound of formula (II) having local or topical as well as systemic corticosteroid activity, said process comprising synthesizing the corresponding corticosteroid compound wherein the 17α-OCOR group in formula (II) is replaced by a 17α-dichloroacetoxy (17α-OCOCHCl2) group, to provide the resultant soft corticosteroid compound of formula (I)
- wherein each X and Y are as defined with formula (II) above.
A compound having the formula (III):
- wherein each X′ is independently H, F or Cl provided that at least one X′ is F or Cl, Y is O or S and the wavy line indicates the α- or β-configuration.
Dependencies are inferred from the claim text.