Estrogenic estra-1,3,5(10)-trienes with differential effects on the alpha and beta estrogen receptors, having a linear hydrocarbon chain of from 5-9 carbon atoms in position 11
View Patent ↗Disclosed is a novel class of steroid compounds based on estradiol, and carrying an 11β-substitution. Said substitution is a hydrocarbon group which may be linear or branched, provided that it comprises, as the longest chain on carbon atom no. 11 of the steroid skeleton, one single linear chain having a length of from 5 to 9 carbon atoms, wherein said chain may be saturated or unsaturated. The resulting compounds have a desirable mixed agonist/antagonist profile for estrogen receptor α and estrogen receptor β.
1. A pharmaceutical composition comprising:
a steroid compound of the structural formula:
wherein:
one of X and Y is OH, the other being H;
R 3 is H or COR′ 3 , with R′ 3 being alkyl or aryl;
R 7 , R 16 , and R 17 each independently are H, alkyl, cycloalkyl, alkenyl, alkynyl or aryl;
R 11 is selected from the group consisting of
and
a pharmaceutical acceptable auxiliary, wherein the compound of formula I possesses ERα agonist activity and having ERβ antagonist activity.
2. A method for treating estrogen deficiency disorders, comprising:
administering to a patient afflicted with an estrogen deficiency disorder a therapeutically effective amount of the pharmaceutical composition of claim 1 .
3. A method of treating estrogen deficiency disorders by inducing ERα agonist activity and ERβ antagonist activity in a patient in need thereof, comprising:
administering a therapeutically effective amount of a steroid compound satisfying the following structural formula:
wherein:
one of X and Y is OH, the other being H;
R 3 is H or COR′ 3 , with R′ 3 being alkyl or aryl;
R 7 , R 16 , and R 17 each independently are H, alkyl, cycloalkyl, alkenyl, alkynyl or aryl;
R 11 is selected from the group consisting of
4. A steroid compound of the structural formula:
wherein:
one of X and Y is OH, the other being H;
R 3 is H or COR′ 3 , with R′ 3 being alkyl or aryl;
R 7 , R 16 , and R 17 each independently are H, alkyl, cycloalkyl, alkenyl, alkynyl or aryl; R 11 is selected from the group consisting of
wherein the compound of formula I possesses ERα agonist activity and ERβ antagonist activity.