1,1-Diaryl-1-oxadiazol-alkylamines

Abstract

The present invention relates to compounds of the following formula ##STR1## wherein Y is straight or branched chain alkylene containing 1-4 carbon atoms; R 1 is lower alkyl containing 1-7 carbon atoms; X is hydrogen, halo such as fluoro, chloro, bromo or iodo, or lower alkyl containing 1-7 carbon atoms; Ar is phenyl, 2-pyridyl, mono-substituted phenyl, wherein the substituent is halo such as fluoro, chloro, or bromo, or lower alkyl containing 1-7 carbon atoms; and R 2 and R 3 are lower alkyl containing 1-7 carbon atoms, or R 2 and R 3 together with N is an azamonocyclic ring selected from the group comprising pyrrolidinyl, piperidino, 4-phenyl-4-hydroxypiperidino, 4-phenyl-4-carboxypiperidino, 4-phenyl-4-carbalkoxypiperidino, or 4-phenyl-4-acetoxypiperidino substituted piperidino and morpholino, or an azabicyclo-alkane containing 6 to 9 carbon atoms and containing at least 5 atoms in each ring of the azabicycloalkane.

What is claimed is: 
     
       1. A compound of the formula and acid addition salts thereof wherein Y is alkylene containing 1-4 carbon atoms; R 1  is lower alkyl; X is hydrogen, halo or lower alkyl; Ar is phenyl, halo-substituted phenyl, lower alkyl substituted phenyl, or 2-pyridyl; and .[.R 2  and R 3  are lower alkyl, or.]. R 2  and R 3  together with N is a heterocyclic ring system consisting of azamonocyclic ring of the formula ##STR28## wherein n is 0 or 1 and Z is oxygen, methylene, phenylhydroxymethylene, phenylcarboxymethylene, phenylcarbloweralkoxymethylene or azabicycloalkane containing 6 to 9 carbon atoms and containing at least 5 atoms in each ring of the azabicycloalkane.  .[.   
     
     
       2.  As in claim 1, a compound of the formula ##STR29## and acid addition salts thereof wherein Y is alkylene; R 1  is lower alkyl; X is hydrogen, halo, or lower alkyl; Ar is phenyl, halo-substituted phenyl, lower alkyl substituted phenyl, or 2-pyridyl; and R 2  and R 3  are lower alkyl..]. 
     
     
       3. As in claim 1, a compound of the formula ##STR30## and acid addition salts thereof wherein Y is alkylene; R 1  is lower alkyl; X is hydrogen, halo, or lower alkyl; Ar is phenyl, halo-substituted phenyl, lower alkyl substituted phenyl, or 2-pyridyl; and R 2  and R 3  together with N is a heterocyclic ring system consisting of azamonocyclic rings of the formula ##STR31## wherein n is 0 or 1 and Z is oxygen, methylene, phenylhydroxymethylene, phenylcarboxymethylene, phenylcarbloweralkoxymethylene and bicycloazacycloalkane containing 6 to 9 carbon atoms and containing at least 5 atoms in each ring of the azabicycloalkane. 
     
     
       4. As in claim 1, a compound of the formula ##STR32## and acid addition salts thereof wherein Y is alkylene; R 1  is lower alkyl; X is hydrogen, halo, or lower alkyl; Ar is phenyl, halo-substituted phenyl, lower alkyl substituted phenyl, or 2-pyridyl; and R 2  and R 3  together with N is a heterocyclic ring system consisting of azamonocyclic ring of the formula ##STR33## wherein n is 0 or 1 and Z is oxygen, methylene, phenylhydroxymethylene, phenylcarboxymethylene or phenylcarbloweralkoxymethylene. 
     
     
       5. As in claim 1, a compound of the formula ##STR34## and acid addition salts thereof wherein Y is alkylene; R 1  is lower alkyl; X is hydrogen, halo, or lower alkyl; Ar is phenyl, halo-substituted phenyl, lower alkyl substituted phenyl, or 2-pyridyl; and R 2  and R 3  together with N is a heterocyclic ring system consisting of bicycloazacycloalkanes containing 6 to 9 carbon atoms and containing at least 5 atoms in each ring of the azabicycloalkane. 
     
     
       6. As in claim 1, the compound which is 5-{[1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)]propyl}-2-methyl-1,3,4-oxadiazole. .[.7. As in claim 1, the compound which is 5-{[1,1-diphenyl-3-(dimethylamino)]butyl}-2-methyl-1,3,4-oxadiazole..]. .[.8. As in claim 1, the compound which is 5-{[1-phenyl-1-(2-pyridyl)-3-diisopropylamino]propyl}-2-methyl-1,3,4-oxadiazole..]. .[.9. As in claim 1, the compound which is 5-[(1,1-diphenyl-3-diisopropylamino)propyl]-2-methyl-1,3,4-oxadiazole..]. 
     
     
         0. As in claim 1, the compound which is 5-[1,1-diphenyl-3-(2-azabicyclo 
     
     
        [2.2.2]oct-2-yl)propyl]-2-ethyl-1,3,4-oxadiazole. 11. As in claim 1, the compound which is 5-{[1,1-diphenyl-3-(4-acetoxy-4-phenyl)piperidino]propyl}-2-methyl-1,3,4-o 
     
     
       xadiazole. 12. As in claim 1, the compound which is 5-{[1,1-diphenyl-3-(4-hydroxy-4-phenyl)piperidino]propyl}-2-methyl-1,3,4-o 
     
     
       xadiazole. 13. As in claim 1, the compound which is 5-{[1,1-diphenyl-3-(7-azabicyclo[2.2.1]hept-7-yl)]propyl}-2-methyl-1,3,4-o 
     
     
       xadiazole. 14. As in claim 1, the compound which is 5-{[1,1-diphenyl-3-(3-azabicyclo[3.2.2]non-3-yl)]propyl}-2-methyl-1,3,4-ox 
     
     
       adiazole. 15. As in claim 1, the compound which is 5-{[1-phenyl-1-(2-pyridyl)-3-(3-azabicyclo[3.2.2]non-3-yl)]propyl}-2-methyl-1,3,4-oxadiazole.