Compounds, compositions, methods of synthesis, and methods of treatment

Abstract

The present disclosure relates to organic chemistry and in particular to a series of corticotropin releasing factor type-1 (CRF 1 ) receptor ligand compounds and compositions, as well as methods of preparation and treatment.

1 - 24 . (canceled) 
     
     
         25 . A compound of the formula: 
       
         
           
           
               
               
           
         
         wherein 
         X 1  is Br or I; 
         R 1  is Bu, Bu-F, Pr, Pr—F, F—CH 2 —CH═CH—CH 2    
         R 2  is Me, Et, Pr, Pr-F, Et-F, 
         R 4  is 4-Br, 4-Cl, 4-F, 4-I, 4-Me, 4-t-Bu, 4-SnMe 3 , 4-OH, 4-OMeF, 4-OCF 3 , 4-OEtF, 4-OPrF, 4-NO 2 , 4-NH 2 , 4-NHMe, 4-NMe 3 OTf, 4-NMe 3 I, 5-Cl, 5-F, 5-NO 2 , 5-NH 2 , 5-NHMe, 5-F, 5-NHMe, 5-NMe 3 OTf, or 5-NMe 3 I; 
         R 5  is H, 2-Br, 2-Cl, 2-F, 2-I, 2-Me, 2-Et, 2-CF 3 , 2-OMe, 2-OMeF, 2-OCF 3 , 2-OEtF, 2-OPrF, 2-NO 2 , 2-NH 2 , 2-NHMe, 2-NMe 2 , 2-NMe 3 OTf, 2-NMe 3 I, or 2-SnMe 3 ; and a salt of any of the foregoing. 
       
     
     
         26 . The compound of  claim 25 , wherein R 1  is Bu. 
     
     
         27 . The compound of  claim 25 , wherein R 2  is Et. 
     
     
         28 . The compound of  claim 25 , wherein R 4  is 4-SnMe 3 . 
     
     
         29 . The compound of  claim 25 , wherein R 5  is H. 
     
     
         30 . The compound of  claim 25  selected from:
 4-(2-bromo-4-methylphenyl)-8-(butyl(ethyl)amino)-6-methyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one, 
 4-(4-bromo-2-chlorophenyl)-8-(butyl(ethyl)amino)-6-methyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one, 
 4-(2-bromo-4-chlorophenyl)-8-(butyl(ethyl)amino)-6-methyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one, 
 8-(butyl(ethyl)amino)-4-(2,4-dibromophenyl)-6-methyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one, and 
 4-(4-bromo-2-ethylphenyl)-8-(butyl(ethyl)amino)-6-methyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one.