4-Alkyl-2,6-di(secondary or tertiary alkylamino) pyridines, compositions thereof and methods for treating diabetes and obesity

Abstract

Compounds of the formula ##STR1## wherein R is secondary alkyl of 3 to 7 carbon atoms or tertiary alkyl of 4 to 7 carbon atoms, R' is secondary alkyl of 3 to 7 carbon atoms or tertiary alkyl of 4 to 7 carbon atoms, R.sub.1 is alkyl of 1 to 4 carbon atoms, R.sub.2 is hydrogen, chloro or bromo, and R.sub.3 is hydrogen, --CO--R.sub.4 or cyano, Wherein R.sub.4 is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 3 carbon atoms, ##STR2## OR AMINO, WHEREIN EACH X is independently alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or halo or two X's on adjacent carbon atoms together are methylenedioxy, with the proviso that the ortho positions of the phenyl ring are free of halo substituents, and n is 0, 1, 2 or 3, And the pharmaceutically acceptable acid addition salts thereof, Are useful as anti-obesity and anti-diabetic agents. The compounds wherein R.sub.2 is hydrogen and R.sub.3 is alkylcarbonyl, benzoyl or substituted benzoyl are synthesized from ketoketenimines and amidines while those wherein R.sub.2 is hydrogen and R.sub.3 is alkylcarbonyl are also synthesized from isoxazolium salts and ammonia. The compounds wherein R.sub.2 is hydrogen and R.sub.3 is cyano are synthesized from the corresponding 2,6-dihalopyridines as are many of the other compounds. The compounds wherein R.sub.2 is hydrogen and R.sub.3 is alkylcarbonyl, alkoxycarbonyl or carbamoyl are synthesized from the corresponding cyano compounds. The compounds wherein R.sub.2 is hydrogen and R.sub.3 is (C.sub.2-4 alkyl) carbonyl are also synthesized from the corresponding compounds wherein R.sub.3 is acetyl. The compounds wherein R.sub.2 is chloro or bromo are synthesized from the corresponding compounds wherein R.sub.2 is hydrogen and an N-halosuccinimide. The compounds wherein R.sub.3 is hydrogen are synthesized from the corresponding alkylcarbonyl compounds or 2,6-dihalopyridines.

Dependencies are inferred from the claim text.