Preparation of new biodegradable polyurethanes as a therapeutic agent

Abstract

Cubylamines and cubylmethylamines are of interest as antiviral agents. New biodegradable polyurethanes and polyetherurethanes having hydrolytically labile morphine groups as a therapeutic agent were prepared by reacting 1,4-diisocyanatocubane (DICC) with morphine. The polyetherurethanes containing morphine were prepared by reacting poly(ethylene glycol) with an excess of DICC to obtain a prepolymer which was reacted with morphine, which contains two hydroxyl groups. The structure of the polymers was confirmed by FTIR and 1H NMR spectroscopy. The hydrolysis of drug-polymer conjugates was carried out in cellophane membrane dialysis bags containing aqueous buffer solution (pH 8) at 37 °C. UV spectroscopy was used to show that both 1,4-diaminocubane (DAC) and morphine were released by hydrolysis of the polyurethane segments. The polyurethane drug conjugates have longer duration of activity, due to slow release of DAC and morphine.