Process for the production of 19-norpregn-4-en-3,20-dione-17α-ol(gestonorone) and intermediates therefor
AssigneeRichter Gedeon Nyrt.
InventorsJános Csörgei, Anita Horváth, Csaba Sánta, Sándor Mahó, Zoltán Béni, János Horváth
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Abstract
The present invention relates to a new stereoselective process for the synthesis of 17(α)-17-acetyl-17-hydroxy-estr-4-en-3-one of formula (I), as well as to the new intermediates of the process. The 17(α)-17-acetyl-17-hydroxy-estr-4-en-3-one (gestonorone) is an important intermediate in the synthesis of the active ingredients having progestogen activity—such as gestonorone capronate and nomegestroi acetate. Formulas (I), (II) and (III).
Claims20
A process for the synthesis of (17α)-17-acetyl-17-hydoxy-estr-4-en-3-one of formula (I)
- characterized by reacting the compound of formula (II)
- with 1.5-10 mol equivalent of methyl lithium in the presence of substituted 1,2-diamino-ethane in an ether or formaldehyde dialkylacetal solvent or a mixture thereof at a temperature between −78° and −10° C., then reacting the protected imine derivative obtained as intermediate with mineral acids or strong organic acids at a temperature between 0° C. and the boiling point of the applied organic solvent.
(17α)-3-methoxy-17-[(trimethylsilyl)-oxy]-estr-2,5(10)-dien-17-carbonitrile of formula (II)
(17α)-17-hydroxy-3-methoxyestra-2,5(10)-dien-17-carbonitrile of formula (III)
Dependencies are inferred from the claim text.