A practical synthesis of cabergoline.
Cabergoline is an N-acylurea derived from 9,10-dihydrolysergic acid, which is a potent prolactin inhibitor. It is marketed by Pharmacia as Dostinex for the treatment of hyperprolactinemia and is currently under active development for the treatment of a variety of CNS disorders. In the existing process, the N-acylurea is formed by the reaction of an amide with a large excess of ethyl isocyanate at elevated temperatures. An improved process was developed that eliminates this hazardous reaction. The amide is reacted with phenyl chloroformate and then with ethylamine, which provides a mild and efficient means of forming the unsymmetrical N-acylurea.
D000077465:Cabergoline; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D015259:Dopamine Agents / Q000138:chemical synthesis* / Q000737:chemistry; D004873:Ergolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011388:Prolactin / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry
D015259:Dopamine Agents; D004873:Ergolines; D014508:Urea; D011388:Prolactin; D000077465:Cabergoline