Ticlid,Millot,France,1978
mucolytic, antibacterial, surface active agent
An antithrombotic. a platelet aggregation inhibitor
Ticlopidine hydrochloride is a selective P2Y12 receptor antagonist. It inhibits ADP-induced platelet aggregation and displays antithrombotic activity following oral administration in vivo.
A solution of thieno[3,2-c]pyridine (13.5 g; 0.1 mol) and 2-chlorobenzyl
chloride (17.7 g) in acetonitrile (150 ml) is boiled during 4 hours.
After evaporation of the solvent, the solid residue consists of 5-(2-
chlorobenzyl)-thieno[3,2-c]pyridinium chloride which melts at 166°C
(derivative n° 30). This compound is taken up into a solution comprising
ethanol (300 ml) and water (100 ml). Sodium borohydride (NaBH4)(20 g) is
added portionwise to the solution maintained at room temperature. The
reaction medium is maintained under constant stirring during 12 hours and is
then evaporated. The residue is taken up into water and made acidic with
concentrated hydrochloric acid to destroy the excess reducing agent. The
mixture is then made alkaline with ammonia and extracted with ether. The
ether solution is washed with water, dried and evaporated. The oily residue is
dissolved in isopropanol (50 ml) and hydrochloric acid in ethanol solution is
then added thereto.
After filtration and recrystallization from ethanol, there are obtained 5-(2-
chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride crystals
(yield: 60%) having a melting point (Koefler block) of 190°C.
Platelet aggregation inhibitor
Selective P2Y 12 receptor antagonist. Inhibits ADP-induced platelet aggregation and displays antithrombotic activity following oral administration in vivo .
