Epipremnum Aureum

by | Mar 19, 2018 | Epipremnum Aureum

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

Synthesis

Thieme ChemDrug Synthesis[2][3] Patent:[4] Prec (Ex 23):[5] Recent Sino:[6][7][8]

The free-radical halogenation of Ethyl 4-methylcinnamate [20511-20-0] (1) with N-bromosuccinimide in the presence of benzoyl peroxide gives Ethyl 4-bromomethylcinnamate [60682-98-6] [78712-67-1] (2). Amination with Imidazole [288-32-4] (3) gives ethyl (E)-3-[4-(imidazol-1-ylmethyl)phenyl]acrylate [78712-80-8] (4). Lastly saponification of the ester completed the synthesis of Ozagrel (5).

References

  1. ^ Loo MH, Egan D, Vaughan ED, Marion D, Felsen D, Weisman S (March 1987). "The effect of the thromboxane A2 synthesis inhibitor OKY-046 on renal function in rabbits following release of unilateral ureteral obstruction". J. Urol. 137 (3): 571–6. doi:10.1016/s0022-5347(17)44108-5. PMID 3820396.
  2. ^ Blancafort, P.; Serradell, MN; Pento, JT; Castaer, J.; OKY-046. Drugs Fut 1983, 8, 4, 328.
  3. ^ Iizuka, Kinji; Akahane, Kenji; Momose, Denichi; Nakazawa, Masayuki; Tanouchi, Tadao; Kawamura, Masanori; Ohyama, Isao; Kajiwara, Ikuo; Iguchi, Yohichi (1981). "Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives". Journal of Medicinal Chemistry. 24 (10): 1139–1148. doi:10.1021/jm00142a005.
  4. ^ Morita Kaname, et al. EP0058079 (to Kissei Pharmaceutical Co Ltd, Ono Pharmaceutical Co Ltd).
  5. ^ Edward J. Cragoe, Jr. & John B. Bicking, U.S. patent 4,175,203 (1979 to Merck and Co Inc).
  6. ^ Liu Rong, Xiang Song, & Yu Xiangli, CN111333581 (2020 to Beijing Hasanlian Science & Technology Co ltd, Harbin Medisan Pharmaceutical Co Ltd, Lanxi Hasanlian Pharmaceutical Co ltd).
  7. ^ 张丽华, CN113493416 (2021 to Chifeng Jingfang Pharmaceutical Technology Development Co Ltd).
  8. ^ Zhang Lihua, et al. CN115141098 (2022 to Chifeng Jingfang Pharmaceutical Technology Development Co ltd).


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