Method of producing...

Details Method of producing... Method of producing...

C - Chemistry, Metallurgy

07

J

C07J 73/00 (2006.01) C07J 7/00 (2006.01) C07J 71/00 (2006.01) C07J 75/00 (2006.01)

Patent

CA 2461221

The invention relates to the production of 17.beta.-(substituted)-3-oxo- .DELTA.1,2-4-azasteroids (I), wherein R1 is a C1-C4 alkyl, OR2, wherein R2 is a C1-C4 alkyl, or NR3R4, wherein R3 and R4, which may be identical or different, denote hydrogen or a C1-C4 alkyl radical. According to the invention, the latter are obtained using a method consisting in: breaking the oxazolidinethione ring present in a 2-(substituted)-3-hydroxyoxazolidinethione having formula (IV), wherein R5 is Br or trichloromethylsulphonyl; and eliminating the substituent in position 2 in order to form a double bond in position 1,2. Some (I) compounds are inhibitors of testosterone-5.alpha.- reductase and can be used in the treatment of hyperandrogenic alterations.

L'invention concerne les 17.beta.-(substitué)-3-oxo-.DELTA.?1,2¿-4-azastéroïdes de la formule (I), dans laquelle : R?1¿ est un alkyle C¿1?-C¿4?, OR?2¿ ; R?2¿ est un alkyle C¿1?-C¿4?, ou NR?3¿R?4¿ ; R?3¿ y R?4¿, égales ou différents, représentent hydrogène ou un radical alkyle C¿1?-C¿4?, lesquels peuvent s'obtenir au moyen d'un procédé consistant à : briser l'anneau d'oxazolidinédione présent dans un 2-(substitué)-3-hydroxyoxazolidinédione de formule (IV), dans laquelle R?5¿ est Br ou trichlorométylsulphonyle, et éliminer le substituant dans la position 2, pour former une double liaison dans la position 1,2. Certains de ces composés (I) sont inhibiteurs de la testostérone-5.alpha.- reductase et peuvent s'utiliser dans le traitement d'altérations hyperandrogéniques.

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