Process and new intermediates for the preparation of...

Details Process and new intermediates for the preparation of... Process and new intermediates for the preparation of...

2003-07-31

2010-02-23

Badio, Barbara P (Department: 1612)

Organic compounds -- part of the class 532-570 series

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

C552S648000, C552S650000, C540S033000

Reexamination Certificate

active

07667056

ABSTRACT:
The present invention relates to a new process of synthesis and to some new intermediates for the preparation of steroids with progestogen activity, more particularly, for the preparation of Desogestrel of formula (I). Said process is characterized by the regioselective reduction of the compound of formula (II) to give the intermediate of formula (III).

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Schwarz et al., “Synthesis of 13-Ethyl-11-methylene-18, 19-dinor-17-alpha-pregn-4-en-20-yn-17-ol (Desogestrel) and its Main Metabolite 3-Oxo-Desogestrel.” Tetrahedron, vol. 5, No. 36, 1994, pp. 10709-10720, XP000611446 pp. 10711-10713, schemes 4-6.
Gao et al., “Synthesis of 13-ethyl-17-hydroxy-11-methylene-18, 19-din-or-17alpha-pregn-4-en-20-yn-3-one (3-oxo desogestrel).” Steroids, vol. 62, 1997, pp. 399-402, XP004082728, p. 401, scheme 4.
Gribble, G.W. et al., “Reactions of Sodium Borohydride in Acidic Media; VII. Reduction of Diaryl Ketones in Trifluoroacetic Acid,” Synthesis, vol. 10 (1978), pp. 763-765.
Smith, H., et al., “Totally Synthetic(+−)-13-Alky1-3-hydroxy and Methoxy-gona-1,3,5(10)-trien-17-ones and Related Compounds,” Experentia, 19, (1963), pp. 394-396.
Green, T., “Protective Groups in Organic Synthesis, 3rd Edition, (1999) p. 297.

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