Patent GB-769554-A (GB)
Title: Organic acid addition salts of alkamine esters of unsubstituted aminosalicylic acids and of alkamine esters of aminosalicylic acids substituted at the nitrogen atom and a process for their production
Filed: 1952-07-30
Abstract: The invention comprises addition salts of a non-toxic organic acid (except a penicillin) with an alkamine ester of an amino-salicylic acid or of an alkamine ester of an aminosalicylic acid substituted at the nitrogen atom.  Such compounds are obtained by reacting the alkamine ester and the acid in solution or as a melt or by double decomposition.  The non-toxic acids may be aliphatic, aromatic, hydroaromatic or heterocyclic saturated or unsaturated carboxylic, sulphonic or phosphoric acids or bifunctional acids.  They may contain amino, hydroxyl, nitro, halogen, alkyl, alkoxy, aryl, aryloxy, alkaryl or aralkyl groups or heterocyclic residues such as the pyridino, piperidino or pyrimidino group.  Acid esters of organic acids and phosphorus-containing acids are included.  Acids specified are 2- and 4-amino-benzoic, 4-amino-salicylic, 4-n-butylaminosalicylic, metanilic, 4-toluene-sulphonic, b -naphthalene sulphonic, 2 - hydroxy - 4 - nitrobenzoic and 2 - hydroxy - 5 - nitrobenzoic acids.  Examples describe the preparation of salts of (1) butyric acid and the piperidinoethyl ester of 4-amino-salicylic acid; (2) undecene-(1)-acid-(11) and 4-amino-salicylic acid diethylaminoethyl ester; (3) d-tartaric acid and 4-amino-salicylic acid dimethylaminoethyl ester (neutral salt); (4) mono-ethyl phosphoric acid and 5-amino-salicylic acid diethylaminoethyl ester; (5) isethionic acid and 4-n-propylamino-salicylic acid g -diisobutylaminopropyl ester; (6) crotonic acid and 4-n-butylaminosalicylic acid diethylaminoethyl ester; (7) 4-aminosalicylic acid and 4-aminosalicylic acid diethylaminoethyl ester; (8) p-amino benzoic acid and 4-aminosalicylic acid piperidino-ethyl ester; (9) 4-n-butylaminobenzoic acid and 4-aminosalicylic acid dimethylaminoethyl ester; (10) p-toluene sulphonic acid and 5-aminosalicylic acid g -dimethylaminopropyl ester; (11) metanilic acid and 4-amino-salicylic acid diethylaminoethyl ester; (12) anthranilic acid and 3-aminosalicylic acid diethylaminoethyl ester; (13) picolinic acid and 4-aminosalicylic acid diethylaminoethyl ester; (14) phthalic acid and 4-isopropylaminosalicylic acid diethylaminoethyl ester; (15) 2-hydroxy-4-nitrobenzoic acid and 4-n-butylaminosalicylic acid diethylaminoethyl ester; (16) b -naphthalenesulphonic acid and 4-n-butylaminosalicylic acid piperidinoethyl ester; (17) 4-aminosalicylic acid and 4-n-butylaminosalicylic acid diethylaminoethyl ester; (18) 2-hydroxy-5-nitrobenzoic acid and 5-n-butylamino-salicylic acid diethylaminoethyl ester.  Other alkamine esters mentioned are 4-aminosalicylic acid g -diisobutylaminopropyl ester, 4 - n - propylaminosalicylic acid piperidinoethyl ester, 4-sec.-butylaminosalicylic acid g -diethylaminopropyl ester, 5 - n - propylaminosalicylic acid diethylaminoethyl ester, 5-b -methoxyethylaminosalicylic acid dimethylaminoethyl ester, the dimethylaminoethyl esters and the diethylaminoethyl esters of 4-methoxy- and 4-butoxyethylaminosalicylic acids.  Specifications 766,325, 766,326 and 766,327 are referred to.ALSO:A therapeutic composition comprises as active ingredient an addition salt of a non-toxic organic acid (except a penicillin) with an alkamine ester of an aminosalicylic acid or of an aminosalicylic and substituted at the nitrogen atom (see Group IV(b)).  Specified are salts containing as the alkamine ester compounds having amino or alkyl- or alkoxyalkylamino groups in the 3-, 4- or 5- position and having dialkylamino alkyl piperidinoalkyl esterifying groups.  The organic acid may be a substituted or unsubstituted aliphatic aromatic, hydroaromatic or heterocyclic carboxylic, sulphonic or phosphoric acid.  It may contain amino, hydroxyl, nitro, halogen, alkyl, alkoxy, aryl, aryloxy or alkaryl or aralkyl groups or heterocyclic residues such as the pyridino, piperidino or pyrimidin residues.  The composition may be in the form of an aqueous solution, in powder or tablet form in admixture with a diluent or in the form of an ointment in a base such as lanoline or petroleum jelly.  A fungicidal and anaesthetic composition referred to contains the crotonic acid salt of the diethylaminoethyl ester of 4-n-butylaminosalicylic acid in lanoline or other ointment base. Specifications 766,325, 766,326 and 766,327 [all in Group IV(b)] are referred to.