Chemistry:Ozagrel

From HandWiki

Ozagrel (INN) is an antiplatelet agent working as a thromboxane A2 synthesis inhibitor.[1]

Synthesis

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The free-radical halogenation of ethyl 4-methylcinnamate (1) with N-bromosuccinimide in the presence of benzoyl peroxide gives ethyl 4-bromomethylcinnamate (2).[2] Alkylation of imidazole (3) with this material gives the ethyl ester (4) of the drug, which is saponified to give ozagrel.[3][4]

References

  1. "The effect of the thromboxane A2 synthesis inhibitor OKY-046 on renal function in rabbits following release of unilateral ureteral obstruction". The Journal of Urology 137 (3): 571–576. March 1987. doi:10.1016/s0022-5347(17)44108-5. PMID 3820396. 
  2. Cragoe Jr EJ, Bicking JB, "nterphenylene 11,12-secoprostaglandins", US patent 4175203, issued 20 November 1979
  3. "Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives". Journal of Medicinal Chemistry 24 (10): 1139–1148. October 1981. doi:10.1021/jm00142a005. PMID 7199088. 
  4. "Ozagrel". Pharmaceutical Substances. Georg Thieme Verlag KG. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-15-0068.