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Preparing drospirenone, useful e.g. as hormonal contraceptive, comprises reacting dimethylen-androst-4-en-dione with halo propionic acetaldehyde compound, converting dimethylen-hydroxy-(dialkoxypropyl)-androst-4-ene to spirol and oxidizing
Preparing drospirenone, useful e.g. as hormonal contraceptive, comprises reacting dimethylen-androst-4-en-dione with halo propionic acetaldehyde compound, converting dimethylen-hydroxy-(dialkoxypropyl)-androst-4-ene to spirol and oxidizing
Preparing drospirenone (I) comprises either reacting 6,7,15,16-dimethylen-androst-4-en-3,17-dione with a halo propionic acetaldehyde compound (II) to obtain 6,7,15,16-dimethylen-17beta -hydroxy-17alpha -(3,3-dialkoxypropyl)-androst-4-ene (III), converting (III) to dimethylen-17-spirol (IV), and subsequently oxidizing (IV); or reacting 6,7,15,16-dimethylen-androst-4-en-3,17-dione with o-(3-halopropionic acid)-trialkylester compound (V) to obtain 17alpha -(3,3,3-trialkoxypropyl)-17beta -hydroxy-6,7,15,16-dimethylen-androst-4-en-3-one (VI), and converting (VI) to (I). Preparation of drospirenone (I) comprises either reacting 6,7,15,16-dimethylen-androst-4-en-3,17-dione with a halo propionic acetaldehyde compound of formula (X-CH 2-CH 2-CH(OR) 2) (II) to obtain 6,7,15,16-dimethylen-17beta -hydroxy-17alpha -(3,3-dialkoxypropyl)-androst-4-ene (III), converting (III) to dimethylen-17-spirol (IV), and subsequently oxidizing (IV); or reacting 6,7,15,16-dimethylen-androst-4-en-3,17-dione with o-(3-halopropionic acid)-trialkylester compound of formula (X-CH 2-CH 2-C(OR) 3) (V) to 17alpha -(3,3,3-trialkoxypropyl)-17beta -hydroxy-6,7,15,16-dimethylen-androst-4-en-3-one (VI), and converting (VI) to (I). X : Cl, Br, I, mesylate, tosylate or triflate; and R : not defined. An independent claim is included for the preparation of 6beta ,7beta ,15beta ,16beta -dimethylen-androst-4-en-3,17-dione diastereomer comprising cyclopropanation between the positions 6 and 7 of the steroid nucleus containing double bonds of 15beta ,16beta -methylen-androst-4,6-dien-3,17-dione. ACTIVITY : Antiandrogenic; Contraceptive. MECHANISM OF ACTION : None given.
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