5-Amino or substituted amino-7-phenyl or substituted phenyl-2,3-dihydro-1H-1,4-diazepines

摘要

Compounds of the formula WHEREIN R1 is hydrogen, alkyl of 1 to 6 carbon atoms or amino, R2 is hydrogen or alkyl of 1 to 6 carbon atoms, with the provisos that (1) at least one of R1 and R2 is not a tertiary alkyl group and (2) R2 is hydrogen when R1 is amino, or R1 and R2 taken together and with the nitrogen atom to which they are joined are pyrrolidino, piperidino or N'-2-hydroxyethylpiperazino, EACH X' is independently alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, or two X's on adjacent carbon atoms together are methylenedioxy, 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 R1 is alkyl and R2 is hydrogen are synthesized by a two-step synthesis from 2-alkyl-5-arylisoxazolium salts and ethylenediamine. The compounds wherein R1 and R2 are hydrogen are synthesized by cleaving the t-butyl group from the corresponding compounds wherein R1 is t-butyl and R2 is hydrogen. The compounds wherein R1 is amino are synthesized from the corresponding compounds wherein R1 is hydrogen or alkyl. All of the compounds are synthesized by reacting ammonia, a suitable amine or hydrazine with a compound of the formula WHEREIN R' is primary or secondary alkyl of 1 to 4 carbon atoms.