Uses
Cerestat is a Potent and Noncompetitive NMDA receptor antagonist, Significantly reduced ischemic volume in rat focal cerebral ischemia model. (2). It is a neuroprotective, decreases contusion volume, reduced hemispheric swelling and ICP and also increases CPP. (3)
Manufacturing Process
A solution of m-ethylphenylcyanamide (1.46 g, 10 mmol) and sodium hydride
(480 mg, 20 mmol, prewashed with hexane) in anhydrous THF (10 ml) was
heated at 80-85°C for 2.5 hours. After it was allowed to cool to room
temperature, methyl iodide (3.5 g, 25 mmol) was added and stirring
continued at room temperature for 2 hours. Methanol (10 ml) followed by
water (20 ml) was added and the reaction mixture was extracted with
dichloromethane (3x25 ml). Concentration of the organic layer followed by
flash chromatography on SiO2 afforded N-(m-ethylphenyl)-N-methylcyanamide
(960 mg, 60%) as a colorless liquid: IR (film): 2220, 3400cm-1.
A mixture of m-ethylphenyl-N-methylcyanamide (520 mg, 3.25 mmol) and 1-
aminonaphthalene hydrochloride (508 mg, 3.25 mmol) was placed in a
preheated oil bath at 160°C for 3 hours and then allowed to cool to room
temperature. The resulting solid was taken into dichloromethane and washed
with 10% sodium hydroxide solution. The organic layer was concentrated and
the resulting residue was dissolved in absolute ethanol (2 ml) and treated
with dilute hydrochloric acid. It was concentrated and the solid was twice recrystallized from absolute ethanol-ether to give N-(1-naphthyl)-N'-(methylphenyl)-
N'-methylguanidine hydrochloride (403 mg, 37%) as off-white
needles, melting point 223-225°C.
