Orally active 7.alpha.-alkyl androgens

Abstract

Orally Active androgens are derivative of 7α-methyl-19-nortestosterone. The compounds satisfy formula (I) wherein R 1 is O, (H,H), (H,OR), NOR, with R being hydrogen, (C 1-6 ) alkyl, or (C 1-6 ) acyl; R 2 is ethyl optionally substituted by halogen; R 3 is hydrogen, (C 1-2 ) alkyl, or ethenyl; R 4 is (C 1-2 ) alkyl; R 5 is hydrogen, or (C 1-15 )acyl; and the dotted lines indicate optional bonds.

We claim:  
     
         1 . A compound of the structural formula:  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is O, (H,H), (H,OR), NOR, with R being hydrogen, (C 1-6 ) alkyl, or (C 1-6 ) acyl;  
 R 2  is ethyl optionally substituted by halogen;  
 R 3  is hydrogen, (C 1-2 ) alkyl, or ethenyl;  
 R 4  is (C 1-2 ) alkyl;  
 R 5  is hydrogen, or (C 1-15 ) acyl; and  
 the dotted lines indicate optional bonds with the proviso that the compound is not (7α,17β)-7-ethyl-17-hydroxyestr-4-en-3-one, (7α-ethyl-19-nortestosterone) or a carboxylic ester thereof.  
 
     
     
         2 . The compound according to  claim 1 , wherein R 2  is ethyl.  
     
     
         3 . The compound according to  claim 1 , wherein R 1  is oxo, R 3  is hydrogen, and the dotted lines indicate a Δ 4  double bond.  
     
     
         4 . The compound (7α,17β)-7,13-diethyl-17-hydroxygon-4-en-3-one.  
     
     
         5 . A pharmaceutical composition, comprising: 
 a pharmaceutically acceptable carrier and    a steroid compound, as a medicinally active agent, satisfying formula I                          wherein    R 1  is O, (H,H), (H,OR), NOR, with R being hydrogen, (C 1-6 ) alkyl, or (C 1-6 ) acyl;    R 2  is ethyl optionally substituted by halogen    R 3  is hydrogen, (C 1-2 ) alkyl, or ethenyl;    R 4  is (C 1-2 ) alkyl;    R 5  is hydrogen, or (C 1-15 ) acyl; and    the dotted lines indicate optional bonds.    
     
     
         6 . The pharmaceutical composition according to  claim 5 , wherein R 2  is ethyl.  
     
     
         7 . The pharmaceutical composition according to  claim 6 , wherein the steroid compound is selected from the group consisting of (7α,17β)-7-ethyl-17-hydroxyestr-4-en-3-one and (7α,17β)-7,13-diethyl-17-hydroxygon-4-en-3-one.  
     
     
         8 . The pharmaceutical composition according to  claim 5  suitable for oral administration.  
     
     
         9 . A kit for male contraception, comprising: 
 a progestagen and an androgen, wherein the androgen is a compound according to  claim 1 .    
     
     
         10 . A method of treatment of androgen insufficiency, comprising: 
 administering to a patient in need thereof an effective amount of an androgen, wherein the androgen is a steroid compound satisfying formula I                          wherein    R 1  is O, (H,H), (H,OR), NOR, with R being hydrogen, (C 1-6 ) alkyl, or (C 1-6 ) acyl;    R 2  is ethyl optionally substituted by halogen;    R 3  is hydrogen, (C 1-2 ) alkyl, or ethenyl;    R 4  is (C 1-2 ) alkyl;    R 5  is hydrogen, or (C 1-15 ) acyl; and    the dotted lines indicate optional bonds.    
     
     
         11 . The method of treatment according to  claim 10 , wherein R 2  is ethyl.  
     
     
         12 . The method of treatment according to  claim 11 , wherein the steroid compound is selected from the group consisting of(7α,17β)-7-ethyl-17-hydroxyestr-4-en-3-one and (7α,17β)-7,13-diethyl-17-hydroxygon-4-en-3-one.