SUBSTITUTED 2-HYDROXY-3-[1-(1H-IMIDAZOLE-4-YL)-ALKYL]-BENZENE CARBOXIMIDEAMIDES, THEIR OPTICAL ISOMERS AND THEIR RACEMIC MIXTURES OR THEIR NONTOXIC OPHTHALMOLOGICALLY ACCEPTABLE ACID SALTS Russian patent published in 1999 - IPC

FIELD: organic chemistry. SUBSTANCE: invention relates to compounds of the general formula (I) where R₁ - hydrogen atom or alkyl radical with 1-4 carbon atoms; R₂ - hydrogen atom, hydroxyl group, amino-group or alkyl radical with 1-4 carbon atoms; R₃ - hydrogen atom, or R₂ and R₃ form together group -CH₂-CH₂-. Invention relates to also a method of synthesis of compounds of the formula (I) that involves interaction of compound of the formula (II) where R₁ has a value indicated above with alkanol with 1-4 C-atoms in the presence of gaseous hydrogen chloride. Synthesized compound of the formula (III) where value R₁ is indicated above and alk means alkyl radical with 1-4 C-atoms is interacted with one of enantiomers of α--methylbenzylamine. Synthesized 2-hydroxy-3-[1-(1H-imidazole- -4-yl)-alkyl] -N--α-methylbenzylbenzene carboximideamide of the formula (IV) where R₁ has the above indicated value is interacted with compound of the formula R₂NH₂ (V) where R₂ means hydrogen atom, hydroxyl group, amino-group or alkyl radical with 1-4 C-atoms if R₃ means hydrogen, or with ethylenediamine if R₂ and R₃ mean together -CH₂-CH₂-group. For synthesis of compound of the formula (I) as an optic isomer N--α--methyl- -benzylated diastereomers of the formula (IV) where R₁ means alkyl radical with 1-4 C-atoms are separated. For synthesis of compound of the formula (I) where R₂ and R₃ mean hydrogen alpha-methylbenzyl-group in separated diastereomers is removed by hydrolysis with concentrated hydrochloric acid at 80-110 C and if necessary the end product is converted to acid additive salt. Invention proposes also a pharmaceutical composition for intraocular pressure decrease that contains an active component as one or some 2-hydroxy-3-[1-(1H-imidazole-4-yl)-alkyl] -benzene carboxyimideamides of the formula (I) or their nontoxic ophthalmologically acceptable acid salts at amount 0.01 wt.-%. Compounds of the formulas (I), (II), (III), (IV) and (V) are given in description of invention. EFFECT: improved method of synthesis, enhanced effectiveness of compounds. 15 cl, 4 tbl