3,20-Diketo, 6-methyl, 17-alpha-hydroxy 19-norpregna 4,6-diene, its esters and the uses thereof
OwnerJean M. Gastaudinventor
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Abstract
A novel 3,20-diketo, 6-methyl, 17-alpha hydroxy 19-norpregna-4,6-diene is disclosed, along with a method for its production from 17-alpha-hydroxy 19-nor-progesterone acetate. The 17-alpha acetic ester, and the 17-alpha saturated or unsaturated aliphatic carboxylic acid esters (having up to 11 carbon atoms) of the compound, are also disclosed. The compound and its derivatives are useful in the treatment of luteal deficiency, hyperestrogenic or hyperandrogenic conditions, and seborrhea, either simple or complicated with acne.
Claims18
The 3,20-diketo, 6-methyl,17-alpha hydroxy 19-nor-pregna-4,6-diene.
A process for preparing a 17.alpha.-hydroxy-19-norpregna-4,6-dien-3,20-dione derivative of the formula ##STR3## wherein R is selected from the group consisting of hydrogen, acetyl, and saturated and unsaturated acyl groups of up to 11 carbon atoms, which comprises:
- (a) reacting 17.alpha.-acetoxy-3,20-diketo-19-norpregna-3,5-diene with ethyl orthoformate in acid medium to give 3-methoxy-17.alpha.-acetoxy-20-keto-19-norpregna-3,5-diene;
- (b) reacting said compound with phosphorus oxychloride and dimethylformamide to give 6-formyl-3-methoxy-17.alpha.-acetoxy-20-keto-19-norpregna-3,5-diene;
- (c) reducing said compound with sodium borohydride to give 6-hydroxymethyl-3-methoxy-17.alpha.-acetoxy-20-keto-19-norpregna-3,5-diene
- (d) reacting said nonisolated compound with acid to give 6-methylene-17.alpha.-acetoxy-19-norprogesterone;
- (e) isomerizing said compound in the presence of palladium on charcoal to give 3,20-diketo-6-methyl-17.alpha.-acetoxy-19-norpregna-4,6-diene;
- (f) hydrolyzing said compound with potassium methylate to form 3,20-diketo-6-methyl-17.alpha.-hydroxy-19-norpregna-4,6-diene;
- and
- (g) esterifying said compound with an appropriate esterfying reagent.
Dependencies are inferred from the claim text.