Butofilolol (trade name Cafide) is a beta-blocker drug for the treatment of essential hypertension (high blood pressure).[1][2] It is not known to be marketed anywhere.
The Fries rearrangement of the ester formed by 4-fluorophenol (1)[3] and butryryl chloride (2) gives 5'-fluoro-2'-hydroxybutyrophenone (3). Treatment with epichlorohydrin in the presence of base leads to 1-[5-fluoro-2-(oxiranylmethoxy)phenyl]butan-1-one (4). Lastly, reaction with tert-butylamine gives butofilolol.[4][5]
References
^Houin G, Barre J, Jeanniot JP, Ledudal P, Cautreels W, Tillement JP (1984). "Pharmacokinetics of butofilolol (CAFIDE) after repeated oral administration in man". International Journal of Clinical Pharmacology Research. 4 (3): 175–83. PMID6149195.
^Toussain P, Gay G, Debry G (June 1983). "[Long-term hypotensive treatment by butofilolol]". Annales de Cardiologie et d'Angeiologie. 32 (4): 277–83. PMID6412614.
^Mercier C, Youmans P (1996). "4-fluorophenol: A key intermediate for agrochemicals and pharmaceuticals". The Roots of Organic Development. Industrial Chemistry Library. Vol. 8. pp. 293–300. doi:10.1016/S0926-9614(96)80020-7. ISBN 978-0-444-82434-9.
^US 4252825, Demarne H, "ompositions for treatment of cardiovascular conditions associated with overproduction of catecholamines", issued 24 February 1981, assigned to C. M. Industries)
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