17β-hydroxysteroid dehydrogenase type 3 inhibitors for the treatment of androgen dependent diseases
View Patent ↗In its many embodiments, the present invention provides a novel class of compounds as illustrated below, wherein the various moieties are described herein, as inhibitors of type 3 17β-hydroxysteroid dehydrogenase, pharmaceutical compositions containing one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with type 3 17β-hydroxysteroid dehydrogenase using such compounds or pharmaceutical compositions.
1. A compound represented by the structural formula:
wherein:
X is CH;
Z is O, NH or N(CH 3 );
R 1 and R 2 are the same or different, each being independently selected from the group consisting of phenyl, pyridyl, phenyl-alkyl- and pyridyl-alkyl-, wherein each of said phenyl, pyridyl, phenyl-alkyl- and pyridyl-alkyl- can be unsubstituted or optionally independently substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of halogen, alkyl, CF 3 , CN, —OCF 3 , —OH, —OCH 3 , —C(O)OH and —C(O)CH 3 ,
R 3 is H, —OH, —OCH 3 or —OCF 3 ;
R 4 is selected from the group consisting of H, alkyl, phenyl, phenylalkyl, pyridyl, pyridylalkyl and piperidyl;
m is a number from 0 to 4, and when m is more than 1, the R 4 groups can be the same or different and are independently selected; and
R 5 is —C(O)OH, —C(O)CH 3 , —C(O)NH 2 , —S(O 2 )OH, —S(O 2 )OCH 3 or —S(O 2 )NH 2 .
2. The compound of claim 1 , wherein Z is O.
3. The compound of claim 1 , wherein Z is NH or H(CH 3 ).
4. The compound of claim 1 , wherein R 1 and R 2 are the same and are phenyl or pyridyl, wherein each of said phenyl or pyridyl is either unsubstituted or optionally independently substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group shown in claim 1 .
5. The compound of claim 1 , wherein R 3 is H.
6. The compound of claim 1 , wherein R 4 is H.
7. The compound of claim 1 , wherein R 5 is —C(O)OH, —C(O)NH 2 or —C(O)CH 3 .
8. The compound of claim 4 , wherein R 1 and R 2 are the same and are phenyl, wherein said both phenyl groups are unsubstituted.
9. The compound of claim 4 , wherein R 1 is unsubstituted phenyl and R 2 is a phenyl substituted with one or more moieties selected from the group consisting of halogen, alkyl, —CF 3 , —OCF 3 , —C(O)OH and —C(O)CH 3 .
10. A pharmaceutical composition comprising a therapeutically effective amount of at least one compound of claim 1 in combination with at least one pharmaceutically acceptable carrier.