Flerobuterol (; developmental code name CRL-40827) is a selective β-adrenergic receptor agonist related to salbutamol which was under development for the treatment of major depressive disorder but was never marketed. It is an agonist of the β1-, β2-, and β3-adrenergic receptors. The drug was under development in France by Cephalon and Lafon and reached phase 2 clinical trials prior to its development being discontinued. It was first described in the scientific literature by 1988 and its development was terminated in 2007. Synthesis The chemical synthesis of flerobuterol was reported:FR2486074 idem Louis Lafon, US4835315 (1989 to Laboratoire L. Lafon).FR2554811 idem Louis Lafon, EP0146443 (1985 to LABORATOIRE L. LAFON Société anonyme dite:).FR2502145 idem Louis Lafon, US486180 (1989 to Cephalon France SAS).
The halogenation of 2'-fluoroacetophenone [445-27-2] (1) with molecular bromine in acetic acid led to 2-Fluorophenacyl bromide [655-15-2] (2). Alkylation with tert-butylamine [75-64-9] led to 2-(tert-butylamino)-1-(2-fluorophenyl)ethenone, PC13374926 (3). The reduction of the ketone with sodium borohydride led to Flerobuterol (4).
References