GB867880A - N-acyl derivatives of (3:5-diamino-2:4:6-triiodobenzoyl)-amino acids and x-ray contrast media containing the same - Google Patents

Abstract

The invention comprises compounds of the general formula: <FORM:0867880/IV (b)/1> and their non-toxic salts with organic or inorganic bases, where X is a methylene or polymethylene group which may be substituted by alkyl or phenyl groups, ac is an acyl radical preferably of an aliphatic carboxylic acid of which the acyl group contains 1-6 carbon atoms. The compounds may be prepared by 3:5-dinitrobenzoylating the amino group of the required amino acid e.g. by reaction with 3:5 dinitrobenzoyl chloride by a Schotten-Baumann reaction, and reducing the acylation product to the corresponding 3:5 diaminobenzoyl product, which is then tri iodinated preferably by means of iodine monochloride in hydrochloric acid, and then N-acylated on both of the amino groups. Examples are given of the preparation of 3:5-bis (acetylamino)-2:4:6-tri-iodo hippuric acid, 3:5-bis (acetylamino)-2:4:6-tri-iodobenzoyl-N-d: 1-leucine, 3: 5-bis (propionylamino)-2:4:6-tri-iodo hippuric acid, 3:5-bis (formylamino)-2:4:6-tri-iodohippuric acid, 3:5-bis (acetylamino)-2:4:6-tri-iodobenzoyl-N-d:1-alanine, and N-[3:5 bis-(acetylamino)-2:4:6 tri-iodobenzoyl]-a -aminophenyl acetic acid and the corresponding unacylated compounds. Methyl glucamine salts of the acylated compounds are specified.ALSO:Compounds of the general formula <FORM:0867880/VI/1> (where X is a methylene or polymethylene group, which may be substituted by alkyl or phenyl groups, and ac is an acyl radical), and non-toxic salts of these compounds with organic or inorganic bases, are used in X-ray contrast media. Compounds specified are 3 : 5-bis-(acetylamino) - 2 : 4 : 6 - triiodo hippuric acid and the corresponding formylamino and propionylamino compounds, 3 : 5-bis-(acetylamino)-2 : 4 : 6 - triiodobenzoyl - N - d : l - leucine and the corresponding d : l-alanine compound, and N - [3 : 5 - bis - (acetylamino) - 2 : 4 : 6 - triiodobenzoyl] - a - aminophenylacetic acid. The compounds may be used with a diluent, and other constituents may be included in the preparation of the X-ray contrast media. In examples compositions are prepared by mixing 3 : 5 - bis - (acetylamino) - 2 : 4 : 6 - triiodo hippuric acid with methyl glucamine and water, and by mixing the methyl glucamine salt of the above hippuric acid compound with sodium citrate, the sodium salt of ethylene diamine tetra-acetic acid, and water.