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US 9,695,213 B2Granted
Process for the preparation of drospirenone
AssigneeIndustriale Chimica S.R.L.
InventorsRoberto Lenna, Johannes Bernardus Maria Rewinkel, Francesco Barbieri, Maria Giovanna Luoni
Life of this patent
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Abstract
A process is described wherein, by employing 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (II) as starting product, in a single stage reaction there is obtained drospirenone, (I), a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic action, that is useful for preparing pharmaceutical compositions with contraceptive action.
Claims5
A process for the preparation of drospirenone of the formula (I):
- comprising the step of:
- reacting 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene -5β-androstane-3β,5,17β-triol of the formula (II):
- with oxygen, at a temperature in the range of 30° C. to 50° C., in the presence of acetic acid, or a mixture of an acid and at least one organic solvent, and a catalytic system consisting of ferric nitrate nonahydrate, sodium chloride and 2,2,6,6-tetramethylpiperidine-1-oxyl radical, or a derivative thereof, selected from the group consisting of 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl radical, 4-methoxy-2,2,6,6 -tetramethylpiperidine-1-oxyl radical, 4-(benzoyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl radical, 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl radical and 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl radical;
- wherein each of the catalytic system components is present in a molar ratio of 15% to 25% in moles with respect to 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene -5β-androstane-3β,5,17β-triol of the formula (II).
1 more element
Dependencies are inferred from the claim text.