5-Aryl-1H-1,5-benzodiazepine-2,4-diones

Abstract

5-Aryl-1H-1,5-benzodiazepine-2,4-diones of a formula selected from the group consisting of ##SPC1## Wherein ##SPC2## -- A -- X wherein R 1 is allyl, methylallyl, dimethylallyl, chloroallyl, cyclohexyl, cycloalkylmethyl, cycloalkenylmethyl of 4 to 7 carbon atoms, phenyl, tolyl, xylyl, methoxyphenyl, dimethoxyphenyl, halophenyl, phenylalkyl of 7 to 8 carbon atoms, pyridyl or --A --X where A is straight or branched alkylene of 1 to 4 carbon atoms, and X is hydroxyl, alkoxy, acyloxy, dialkylamino of 2 to 4 carbon atoms, or a 5- to 6-membered nitrogen-containing heterocyclic ring linked to A through a ring nitrogen atom, R 2 is hydrogen or methyl, R 3 is naphthyl, pyrimidyl, thienyl, pyridyl, methylpyridyl or halopyridyl, R 4 is hydrogen, methyl, methoxy, trifluoromethyl, cyano, halogen, lower alkanoyl or (lower alkoxy of 1 to 2 carbon atoms)-carbonyl, R 5 is hydrogen, methyl, ethyl, methoxy, trifluoromethyl, cyano, nitro, halogen, lower alkanoyl or lower alkoxy-carbonyl, R 6 is hydrogen, methyl, ethyl, methoxy or halogen, R 7 is cyano.[.,.]. .Iadd.or .Iaddend.lower alkanoyl .[.or lower alkoxycarbonyl.]., R 8 is cyano, nitro, lower alkanoyl or lower alkoxycarbonyl, R 9 is hydrogen, methyl, ethyl, methoxy or halogen, and R 10 is hydrogen, methyl, methoxy, trifluoromethyl or halogen, Useful as psychosedatives and anticonvulsives in warm-blooded animals.

We claim: 
     
       1. A compound of a formula selected from the group consisting of ##SPC32## wherein   R 1  is alkyl of 1 to 4 carbon atoms, hydroxyethyl, hydroxypropyl, acetoxyethyl, cyclohexyl, benzyl or phenyl,   R 2  is naphthyl, pyrimidyl, thienyl, pyridyl, methyl-pyridyl or chloropyridyl,   R 3  is chlorine, bromine, trifluoromethyl or cyano,   R 4  is cyano.[.,.]. .Iadd.or .Iaddend.acetyl .[.or methoxycarbonyl.].,   R 5  is cyano, nitro, acetyl or methoxycarbonyl, and   R 6  is halogen or trifluoromethyl.   
     
     
       2. A compound of a formula selected from the group consisting of ##SPC33## and ##SPC34##   wherein   R 1  is straight or branched alkyl of 1 to 3 carbon atoms or hydroxyalkyl of 2 to 3 carbon atoms,   R 3  is pyridyl,   R 4  is halogen, trifluoromethyl or cyano,   R 5  is hydrogen, trifluoromethyl, nitro, cyano or halogen,   R 8  is cyano or nitro, and   R 10  is halogen or trifluoromethyl.   
     
     
       3. A compound according to claim 1, which is 7-chloro-1-methyl-5-(2'-pyridyl)-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione. 
     
     
       4. A compound according to claim 1, which is 7-cyano-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione. 
     
     
       5. A compound according to claim 1, which is 5-(2'-acetyl-phenyl)-7-chloro-1-methyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione. 
     
     
       6. A compound according to claim 1, which is 1-methyl-5-(2'-pyridyl)-7-trifluoromethyl-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione. 
     
     
       7. A compound according to claim 1, which is 1-ethyl-7-chloro-5-(2'-pyridyl)-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione. 
     
     
       8. A compound according to claim 1, which is 7-bromo-1-methyl-5-(2'-pyridyl)-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione.