Reactions of 4-Chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidine-5-amine (Moxonidine) with Aroylpyruvic Acids and Their Functional Derivatives. Analgesic Activity of the Obtained Compounds

Refluxing mixture of 4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidine-5-amine (moxonidine) with methyl ether of benzoylpyruvic acid leads to the formation of benzoylpyruvic acid and 4-hydroxymoxonidine hydrochloride. The presence of anhydrous sodium acetate in the reaction mixture leads to the salt of moxonidine with benzoylpyruvic acid. The interaction of moxonidine with 5-aryl-2,3-dihydro-furan-2,3-diones in acetic acid medium leads to the formation of moxonidine salts with aroylpyruvic acids, the structure of which was confirmed by the retrosynthetic analysis of moxonidine with benzoylpyruvic acid. The X-ray diffraction analysis was performed for the single crystals of 4-hydroxymoxonidine hydrochloride and moxonidine 2,4-dioxo-4-(4-methylphenyl)butanoate. It was shown that the prepared salts are able to suppress somatic pain in laboratory mice in the acetic acid writhing test.

4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidine-5-amine (moxonidine), benzoylpyruvic acid, 5-aryl-2,3-dihydrofuran-2,3-diones, analgesic activity, X-ray diffraction analysis