Combined synthesis route for desogestrel and etonogestrel
AssigneeMerck Sharp & Dohme Corp.
InventorMartin Ostendorf
Life of this patent
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Abstract
The present invention relates to a synthesis route and to steroid derivatives of general formula VI and VII useful in the synthesis of desogestrel and etonogestrel.
Claims11
A process for the manufacture of a steroid derivative according to general formula IX
- using a steroid derivative of general formula VI or VII
- wherein in the steroid derivatives of general formula VI, VII and IX, R1 and R2 are the same and are selected from H and (1-4C)alkyl;
- or R1 and R2, together with the sulphur atoms to which they are attached, form a 1,3-dithiolane or 1,3-dithiane, said dithiolane or dithiane being optionally substituted with one or more (1-4C)alkyl group;
- and
- R3 and R4 are the same and are selected from H and (1-4C)alkyl;
- or R3 and R4, together with the oxygen atoms to which they are attached, form a 1,3-dioxolane or 1,3-dioxane, said dioxolane or dioxane being optionally substituted with one or more (1-4C)alkyl group.
A process for the manufacture of etonogestrel comprising steps 1 through 7, wherein etonogestrel is obtained from the 20-yn-11-methylene-3-dithioacetal steroid derivative of general formula IX by deprotection of the 3-dithioactetal
A process for the manufacture of desogestrel comprising steps 1 through 6 and further comprising an additional step 8, wherein desogestrel is obtained from the 20-yn-11-methylene-3-dithioacetal stereoid derivative of general formula IX by deprotection of the 3-dithioactetal followed by reduction of the resulting carbonyl group
A steroid derivative of general formula VI or VII,
- wherein,
- R1 and R2 are the same and are selected from H and (1-4C)alkyl;
- or R1 and R2, together with the sulphur atoms to which they are attached, form a 1,3-dithiolane or 1,3-dithiane, said dithiolane or dithiane being optionally substituted with one or more (1-4C)alkyl group and R3 and R4 are the same and are selected from H and (1-4C)alkyl;
- or R3 and R4, together with the oxygen atoms to which they are attached, form a 1,3-dioxolane or 1,3-dioxane, said dioxolane or dioxane being optionally substituted with one or more (1-4C)alkyl group.
Dependencies are inferred from the claim text.