1,1-DIARYL-1-OXADIAZOL-ALKYLAMINES

1494943 Oxadiazoles G D SEARLE & CO 1 April 1975 [1 April 1974] 13184/75 Heading C2C Novel compounds I in which Alk is C 2-4 alkylene, R is H or C 1-7 alkyl, X is H, halogen or C 1-7 alkyl, Ar is phenyl, pyridyl, halophenyl or C 1-7 alkyphenyl, and NR<SP>1</SP>R<SP>11</SP> is an azabicycloalkane structure containing 6 to 8 carbon atoms and containing at least 5 atoms in each ring of the azabicycloalkane structure, are prepared by (a) reacting in a basic medium with heating, a compound II with a compound of formula (R<SP>111</SP>CO) 2 O or R<SP>111</SP>COCl in which R<SP>111</SP> is C 1-7 alkyl or carbalkoxy with the proviso that when R<SP>111</SP> is carbalkoxy, the product is heated with an aqueous base and then acidified to give the corresponding carboxylic acid which is decarboxylated to give a compound I where R is H, or (b) reacting a compound IV in which Z is Cl or Br, with a compound of formula HNR<SP>1</SP>R<SP>11</SP> in an inert solvent in the presence of an acid acceptor, the mixture being heated to complete the reaction, or (c) reacting a compound V with a dehydrating agent. Compounds II are prepared by reacting a compound III with an azide ion. Compounds I form non-toxic salts with acids. 2,2 - Diphenyl - 4 - (7 - azabicyclo-[2.2.1]hept- 7-yl) butyronitrile is prepared by reacting 2,2- diphenyl-4-bromobutyronitrile with 7-azabicyclo-[2.2.1] heptane. Compounds I and their pharmaceutically acceptable acid addition salts have antidiarrheal activity.