Antiinflammatory 17,17-bis (substituted thio) androstenes
AssigneeE. R. Squibb & Sons, Inc.
InventorRavi K. Varma
Life of this patent
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Abstract
3-Ketoandrostenes having in the 17-position the substituents R.sub.1 --S-- and R.sub.2 --S-- wherein R.sub.1 and R.sub.2 are the same or different and each is alkyl, cycloalkyl or aryl, have antiinflammatory activity.
Claims24
A 3-ketoandrostene having in the 17-position the substituents R.sub.1 -S- and R.sub.2 -S- wherein R.sub.1 and R.sub.2 are different groups, and each is an alkyl, cycloalkyl or aryl group.
A 3-ketoandrostene having the formula ##STR18## or 1,2-, 6,7- and 15,16-dehydro derivatives thereof, wherein R.sub.1 and R.sub.2 are the same alkyl, cycloalkyl or aryl group;
- R.sub.3 is hydroxy, alkoxy, aryloxy, alkylthio, arylthio, ##STR19## or halogen;
- R.sub.4 is hydrogen, methyl, hydroxy, ##STR20## or halogen;
- R.sub.5 is hydrogen or halogen;
- and
- R.sub.6 is carbonyl or .beta.-hydroxymethylene.
The 3-ketoandrostene in accordance with claim 2, 17-(ethylthio)-9-fluoro-11.beta.-hydroxy-17-(methylthio)androsta-1,4-dien- 3-one.
The 3-ketoandrostene in accordance with claim 2, 17-(ethylthio)-9-fluoro-11.beta.-hydroxy-17-(phenylthio)androsta-1,4-dien- 3-one.
The 3-ketoandrostene in accordance with claim 2, 17-(butylthio)-17-(ethylthio)-9-fluoro-11.beta.-hydroxyandrosta-1,4-dien-3 -one.
The 3-ketoandrostene in accordance with claim 2, 17.alpha.-(ethylthio)-9-fluoro-11.beta.-hydroxy-17-(methylthio)androsta-1, 4-dien-3-one.
The 3-ketoandrostene in accordance with claim 2, 17.beta.-(ethylthio)-9-fluoro-11.beta.-hydroxy-17-(methylthio)androsta-1,4 -dien-3-one.
The 3-ketoandrostene in accordance with claim 2, 17.alpha.-(ethylthio)-11.beta.-hydroxy-17-(methylthio)androsta-1,4-dien-3- one.
The 3-ketoandrostene in accordance with claim 2, 17.beta.-(ethylthio)-11.beta.-hydroxy-17-(methylthio)androsta-1,4-dien-3-o ne.
A method of treating topical inflammation in a mammalian host comprising topically administering an effective amount of a 3-ketoandrostene having in the 17-position the substituents R.sub.1 -S- and R.sub.2 -S- wherein R.sub.1 and R.sub.2 are the same or different and each is alkyl, cycloalkyl or aryl.
A process for preparing a steroid having the formula ##STR24## or 1,2- and 6,7-dehydro derivatives thereof, which comprises reacting a steroid having the formula ##STR25## or 1,2- and 6,7-dehydro derivatives thereof with a thiol having the formula
- R.sub.1 -SH
- in the presence of a Lewis acid and in the presence of a dimethylformamide dialkyl acetal;
- wherein R.sub.1 is alkyl, cycloalkyl or aryl, R.sub.3 is hydrogen, hydroxy, alkoxy, aryloxy, alkylthio, arylthio, ##STR26## or halogen, R.sub.4 is hydrogen, methyl, hydroxy, ##STR27## or halogen, and R.sub.5 is hydrogen or halogen, and R.sub.6 is carbonyl or .beta.-hydroxymethylene.
Dependencies are inferred from the claim text.