17alpha, 21-dihydroxypregnene esters as antiandrogenic agents

Abstract

17α,21-Dihydroxypregna-4,9-diene-3,20-dione and 17α,21-dihydroxypregna-4-ene-3.20-dione 17 and/or 21 esters of having remarkable antiandrogenic activity, and the processes for the preparation thereof.

1 - 8 . (canceled) 
     
     
         9 . A method of treating a patient suffering from acne, seborrhea, hirsutism, alopecia, mastodynia, prostate hyperplasia and carcinoma, virilization syndromes in the female, early puberty, inhibition of sexual aggressiveness in the male or contraception in the male, comprising administering to said patient topically or systemically an effective amount of a compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is hydrogen and R 2  is a C 3 -C 18  acyl group. 
       
     
     
         10 . A method of treating a patient in need of antiandrogenic activity, said method comprising administering to said patient an effective amount of a compound of formula (II) 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  and R 2 , which can be the same or different, are hydrogen or a C 3 -C 18  acyl group, with the proviso that at least one of R 1  and R 2  is different from hydrogen. 
       
     
     
         11 . The method as claimed in  claim 10  wherein R 1  is hydrogen and R 2  is propionyl. 
     
     
         12 . The method as claimed in  claim 10  wherein R 1  and R 2  are butanoyl. 
     
     
         13 . A method of treating a patient in need of antiandrogenic activity comprising administering to said patient an effective amount of a compound of formula (I) as defined in  claim 9 . 
     
     
         14 . A method of treating a patient suffering from acne, seborrhea, hirsutism, alopecia, mastodynia, prostate hyperplasia and carcinoma, virilization syndromes in the female, early puberty, inhibition of sexual aggressiveness in the male or contraception in the male, comprising administering to said patient topically or systemically an effective amount of a pharmaceutical composition comprising as active ingredient a compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is hydrogen and R 2  is a C 3 -C 18  acyl group, in admixture with an acceptable carrier, wherein said active ingredient is present in an amount of 0.1 to 1.0% by weight. 
       
     
     
         15 . The method as claimed in  claim 13 , wherein the compound of formula (I) is administered topically or systemically, for the treatment of acne, seborrhea, hirsutism, alopecia, mastodynia, prostate hyperplasia and carcinoma, virilization syndromes in the female, early puberty, or contraception in the male. 
     
     
         16 . The method as claimed in  claim 10 , wherein the compound of formula (II) is administered topically or systemically, for the treatment of acne, seborrhea, hirsutism, alopecia, mastodynia, prostate hyperplasia and carcinoma, virilization syndromes in the female, early puberty, or contraception in the male. 
     
     
         17 . A method as claimed in  claim 9  wherein the compound of formula (I) is as defined in  claim 9 , wherein R 1  is hydrogen and R 2  is propionate. 
     
     
         18 . A method as claimed in  claim 9  wherein the compound of formula (I) is as defined in  claim 9 , wherein R 1  is hydrogen and R 2  is butyrate. 
     
     
         19 . A method as claimed in  claim 14  wherein the active ingredient is present in an amount of 0.2-0.8% by weight.