Orally-active amino-benzamides - useful as anxiolytics, anticonvulsants, antiemetics and antiulcer cpds.

摘要

Amino-benzamides of formula (I) and their acid addn. salts salts are novel cpds.. In the formula, (a) where the -NH2 gp. is in posn. 4 on the ring then R3= ethylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, N-methyl-cyclohexylamino, benzylamino or 1-ethyl-pyrrolidin-2-yl-aminomethyl; R1=Cl in posn. and R2=H or (b) when the -NH2 gp. is fixed in any other posn on the ring then R3=1-5C alkylamino, 3-7C cycloalkylamino, benzylamino, quinulcidinylamino or -NH-(CH2)n-R4; R4=pyridyl, pyrrolidinyl or piperidyl substd. in posn. 1 by a 1-3C alkyl or when n=2 or 3 may be imidazolonyl pyrrolidino, piperidino or morpholino; n=0,1,2 or 3; R1=H Cl or Br and R2=CF3 or nitro or if R4=1 -substd. pyrrolidinylor piperidyl then R2 may be F, Cl,Br or methyl. (I) are antiemetics, antiulcer, anxiolytics and anti convulsants which have good absorption when administered orally. A typical cpd. is N-(1-ethyl-pyrrolidin-2-ylmethyl) -2-amino-5-chloro-3-trifluoromethyl-benzamide prepd. from 2-amino-5-chloro-3-trifluoromethyl-benzoyl chloride and 1 -ethyl -2-aminomethyl-pyrrolidine with triethylamine in chloroform.