Tetrahydropyranyl ethers of estrogens
AssigneeFarmilla Farmaceutici Milano S.p.A.
InventorsPietro de Ruggieri, Orazio Sighinolfi
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Abstract
Tetrahydropyranyl ethers of estrogens have interesting properties in the cure of climateric and menopausal disturbances, with an excellent dissociation index between their selective effect on the vagina and their very small or zero effect on the endometrium.
Claims5
Compounds of the formula:
- ##STR6## where R is 2'-tetrahydropyranyloxy;
- R.sub.1 is beta-hydroxy;
- R.sub.2 is beta-hydroxy with the proviso that, when R.sub.1 and R.sub.2 are beta-hydroxy, R is 2'-tetrahydropyranyloxy.
A process for preparing 3-(2'-tetrahydropyranyloxy)-estra-1,3,5(10) -- trien-16 beta, 17 beta -- diol which comprises reacting a corresponding 3-benzyloxy -- 16 beta, 17 beta-dihydroxy compound with an acetic anhydride or an acetyl chloride, subjecting the 16, 17-diester so-obtained to hydrogenolysis of the benzyl group in an organic solvent, etherifying the phenolic function thus liberated with 2,3-dihydropyran in the presence of an acid catalyst selected from the group consisting of p-toluenesulphonic acid, POCl.sub.3 and HCl, and finally removing the acetate groups by alkaline hydrolysis.
A compound comprising of 3-(2'-tetrahydropyranyloxy)-16.beta.,17.beta.-diacetoxyestra-1,3,5(10)-tri ene.
A compound comprising of 3-(2'-tetrahydropyranyloxy)-estra-1,3,5(10)-trien-16.beta., 17.beta.-diol.
Dependencies are inferred from the claim text.