Hypoglycaemic 2-amino-benzamido-ethyl-benzoic acid derivs. - prepd. e.g. by reaction of 2-amino-benzoic acid derivs. with 4-aminoethyl-benzoic acid derivs.

摘要

4-(2-(2-Tertiary amino-benzamido) ethyl) benzoic acid derivs. (I) and their salts with organic and inorganic acids and (when R5 is H) bases are new. R1 is H, halogen, NO2, amino, alkanoylamino, alkoxy, CN, COOH, alkoxycarbonyl or dialkylaminosulphonyl (the alkyl residues each being 1-3C); R2 and R3 are 1-7C alkyl or 3-7C cycloalkyl, or N(R2)(R3) is a 3-7C alkyleneimino gp. which is opt. substd. by 1 or 2 1-3C alkyl gps., a 1-3C alkoxy gp., OH, phenyl, COOH or 2-4C alkoxycarbonyl or in which a methylene gp. may be replaced by a 3-4C cyclic ketal gp., an O- or S-atom, a sulphoxide gp. or an imino gp. substd. by phenyl (or pyridyl, or N(R2)(R3) is pyrrolyl, tetrahydro-isoquinolyl or tetrahydro-benzazepinyl; R4 is H or 1-3C alkyl; and R5 is H or 1-4C alkyl. (I) have hypoglycaemic activity, as demonstrated by their effect on blood glucose levels when administered orally to female rats. Thus, 4-(2-(5-chloro-2-dimethylaminobenzamido) ethyl) benzoic acid (mouse LD50 greater than 2000 mg/kg p.o.) in a dosage of 10 mg/kg gives 32%, 18%, 6% and 8% reductions in blood glucose levels 1,2,3 and 4 hrs. after administration.