Non-aromatic estrogenic steroids with a hydrocarbon...

C - Chemistry – Metallurgy – 07 – J

Patent

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Details

C07J 9/00 (2006.01) A61K 31/565 (2006.01) A61K 31/575 (2006.01) C07J 51/00 (2006.01) C07J 71/00 (2006.01)

Patent

CA 2382489

Disclosed are novel, selective estrogens type having a steroid skeleton with a non-aromatic A-ring and a free or capped hydroxyl group at carbon atom No. 3. The estrogens satisfy general formula (I), in which R1 is H, (C1-C3)alkyl or (C2-C3)acyl; R2 is H, .alpha.-(C1-C4)alkyl, .alpha.-(C2-C4)alkenyl or .alpha.-(C2-C4)alkynyl; R3 is H or (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl, each at location 15 or 16 of the steroid skeleton; R4 is H or (C1-C5)alkyl, (C2-C5)alkenyl or (C2-C5)alkynyl, each optionally substituted with halogen; preferred is ethynyl; R5 is H, (C1-C3)alkyl or (C2-C3)acyl; R6 is (C1-C5)alkyl, (C2-C5)alkenyl, (C2-C5)alkynyl or (C1-C5)alkylidene, each optionally substituted with halogen or (C1-C3)alkyloxy; dotted bonds represent optional double bonds.

L'invention concerne un nouveau type d'oestrogènes sélectifs possédant un squelette stéroïde comprenant un noyau A non aromatique et un groupe hydroxyle libre ou coiffé au niveau de l'atome de carbone numéro 3. Ces oestrogènes sont illustrés par la formule (I), dans laquelle R<1> représente H, alkyle C1-C3 ou acyle C2-C3; R<2> représente H, alpha -alkyle C1-C4, alpha -alkényle C2-C4, ou alpha -alkynyle C2-C4; R<3> représente H ou alkyle C1-C4, alkényle C2-C4 ou alkynyle C2-C4, chacun au niveau de la position 15 ou 16 du squelette stéroïde; R<4> représente H ou alkyle C1-C5, alkényle C2-C5 ou alkynyle C2-C5, chacun étant éventuellement substitué par halogène, de préférence, éthynyle; R<5> représente H, alkyle C1-C3 ou acyle C2-C3; R<6> représente alkyle C1-C5, alkényle C2-C5, alkynyle C2-C5 ou alkylidène C1-C5, chacun étant éventuellement substitué par halogène ou alkyloxy C1-C3; les lignes en pointillés représentent de doubles liaisons éventuelles.

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