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US 4,285,937 AGranted
Novel androstadiene-17-carboxylic acid esters
AssigneeCiba-Geigy Corporation
InventorJaroslav Kalvoda
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AssigneeCiba-Geigy Corporation
InventorJaroslav Kalvoda
Estimating the term…
The invention provides novel esters of androstadiene 17-carboxyclic acids of the formula ##STR1## wherein R' represents a hydroxyl group which is esterified with a carboxyclic acid having not more than 7 carbon atoms, R" represents a methyl group in the .alpha.- or .beta.-position or the methylene group, wherein R is H or Cl, each of X and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that at least one of these substituents is one of these halogens, when R is Cl, and that Y is only Cl or F and X only Cl, when R is H and that the androstadiene-17-carboxylic acid ester group does not contain more than 11 carbon atoms. The new esters have pronounced antiinflammatory action coupled with remarkably low systemic side effects on thymus, adrenals and body weight. They are especially suitable to be used in dermatology.
Esters of androstadiene-17-carboxylic acids of the formula ##STR5## wherein R' represents a hydroxyl group which is esterified with a lower aliphatic carboxylic acid having not more than 7 carbon atoms, R" represents a methyl group in the alpha- or beta-position or the methylene group, R is H or Cl, and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that Y is only Cl or F, when R is H and that the androstadiene-17-carboxylic acid ester group is derived from an aliphatic alcohol, so that said group contains not more than 6 carbon atoms.
The methyl 9alpha-chloro-6alpha-fluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-pr opionyloxy-androsta-1,4-diene-17-carboxylate.
The methyl 2-chloro-9alpha-fluoro-11beta-hydroxy-17alpha-propionyloxy-16beta-methyl-3 -oxo-androsta-1,4-diene-17-carboxylate.
Androstadiene-17-carboxylic acids of the formula ##STR6## wherein R' represents a free hydroxyl group or a hydroxyl group which is esterified with a lower aliphatic carboxylic acid having not more than 7 carbon atoms, R" represents a methyl group in the alpha- or beta-position or the methylene group, R is H or Cl, and Y represents a hydrogen, chlorine or fluorine atom, with the proviso that Y is only Cl or F, when R is H.
Esters of androstadiene-17-carboxylic acids of the formula ##STR7## wherein R is hydrogen or chlorine, R.sub.1 is the acyl radical of a lower aliphatic carboxylic acid having not more than 7 carbon atoms and R.sub.2 is the moiety of an aliphatic alcohol with not more than 10 carbon atoms, which is unsubstituted or substituted by halogen, hydroxy, lower alkoxy or acyloxy containing said acyl radical R.sub.1.
Dependencies are inferred from the claim text.