Toloxatone ( Humoryl) is an antidepressant launched in 1984 in France by Sanofi for the treatment of depression. It was discontinued in 2002.
Synthesis
The reaction between
glycidol (1) and
m-toluidine (2) gives 3-m-toluidinopropane-1,2-diol (3). Treatment with diethyl carbonate (4) in the presence of sodium methoxide leads to an intermolecular cycloaddition to give tomoxatone.
[Sungurbey, K .; Castaer, J .; Toloxatone. Drugs Fut 1976, 1, 12, 569.][Douzon, C.; Fauvan, C.; Une nouvelle serie d'antidpresseurs: les derivs de l'hydroxymthyl-5-oxazolidinone-2. Chimie Thrapeutique 1973, 3, 324-327.][DE2012120 Claude P Fauran, Guy M Raynaud, Rene A Oliver, Colette A Douzon, (1972 to Delalande Sa).]
See also
