N-(imidazolidin-2-ylidene)quinoline derivatives as modulators of alpha 2 adrenergic receptors

Abstract

The present invention relates to novel N-(imidazolidin-2-ylidene)quinoline derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals.

What is claimed is: 
     
         1 . A method of treating a skin condition in a mammal, the method comprising administering to the mammal in need thereof a pharmaceutical composition comprising a therapeutically effective amount of at least one compound of Formula I 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is hydrogen, substituted or unsubstituted C 1-8  alkyl or halogen; 
         Y is CH or N; and 
         X is CH or N; 
         or a pharmaceutically acceptable salt thereof; 
         provided that the compound is not N-(4,5-dihydro-1H-imidazol-2-yl)-3-quinolinamine. 
       
     
     
         2 . The method according to  claim 1 , wherein the skin condition is selected from: rosacea, sunburn, psoriasis, acne, acne rosacea, photoaging, seborrheic dermatitis, allergic dermatitis, telangiectasia of the face, rhinophyma, burning or stinging sensation of the face, erythema of the skin, cutenous hyperactivity with dilation of blood vessels of the skin, Lyell's syndrome, Stevens-Johnson syndrome, erythema multiforme minor and erythema multiforme major. 
     
     
         3 . The method according to  claim 1 , wherein:
 R 1  is hydrogen, methyl, bromine or chlorine;   Y is CH or N; and   X is CH or N.   
     
     
         4 . The method according to  claim 1 , wherein:
 R 1  is methyl, bromine or chlorine;   Y is CH or N; and   X is CH or N.   
     
     
         5 . The method according to  claim 1 , wherein:
 R 1  is methyl;   Y is CH or N; and   X is CH or N.   
     
     
         6 . The method according to  claim 1 , wherein:
 R 1  is bromine;   Y is CH or N; and   X is CH or N.   
     
     
         7 . The method according to  claim 1 , wherein:
 R 1  is chlorine;   Y is CH or N; and   X is CH or N.   
     
     
         8 . The method according to  claim 1 , wherein:
 R 1  is chlorine;   Y is CH or N; and   X is CH.   
     
     
         9 . The method according to  claim 1 , wherein:
 R 1  is chlorine;   Y is CH; and   X is CH or N.   
     
     
         10 . The method according to  claim 1 , wherein the compound of Formula I is selected from:
 N-(imidazolidin-2-ylidene)-4-methylquinolin-3-amine;   4-Chloro-N-(imidazolidin-2-ylidene)quinolin-3-amine;   4-Bromo-N-(imidazolidin-2-ylidene)quinolin-3-amine;   N-(imidazolidin-2-ylidene)pyrido[2,3-b]pyrazin-7-amine;   N-(imidazolidin-2-ylidene)-8-methylpyrido[2,3-b]pyrazin-7-amine; and   4-Chloro-N-(imidazolidin-2-ylidene)-1,5-naphthyridin-3-amine;   and pharmaceutically acceptable salts thereof.   
     
     
         11 . The method of  claim 1 , wherein the compound has the following structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         12 . The method of  claim 1 , wherein the skin condition is selected from rosacea, sunburn, erythema of the skin, telangiectasia of the face, and cutenous hyperactivity with dilation of blood vessels of the skin. 
     
     
         13 . The method of  claim 12 , wherein the skin condition is rosacea. 
     
     
         14 . The method of  claim 1 , wherein the skin condition is psoriasis. 
     
     
         15 . The method of  claim 11 , wherein the skin condition is selected from rosacea, sunburn, erythema of the skin, telangiectasia of the face, and cutenous hyperactivity with dilation of blood vessels of the skin. 
     
     
         16 . The method of  claim 15 , wherein the skin condition is rosacea. 
     
     
         17 . The method of  claim 11 , wherein the skin condition is psoriasis. 
     
     
         18 . The method of  claim 1 , wherein the mammal is a human.