Synthesis and Physical Studies of the Organic Salts of Pindolol: Pindolol Benzoate and Pindolol 2-Methoxyphenylacetate

Abstract

In order to investigate the formation of organic salts of drugs, two salts of pindolol were prepared using salt-forming agents which were crystalline and suitable for physical studies in the solid state. The stoichiometry of the products, pindolol benzoate and pindolol 2-methoxyphenylacetate, was established by elemental analysis. The precipitates formed were assessed by differential scanning calorimetry (DSC), thermogravimetry (TG), x-ray powder diffractometry (XRPD) and Fourier transform-infrared spectrometry (FT-IR). According to the TG and DSC curves, there was no water of crystallization in the precipitates, and the products were thermally stable. Both precipitates gave one sharp melting endotherm which differed from the endotherms of the starting compounds. The x-ray dipaction pattern of the precipitates direred clearly from those of the starting materials, acid and base. The products showed absorption by FT-IR typical of carboxylic acid salts at about 1640-1540 cm⁻¹. The carbonyl absorption indicative of the carboxylic acid group of benzoic acid or 2-methonyphenylacetic acid was not detectable in the spectra of the precipitates. All this indicates that two new crystalline organic salts (1:1) were formed during the syntheses.