Chemistry:Butofilolol
From HandWiki
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.
It is an example of a butyrophenone.
Synthesis
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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
- ↑ "Pharmacokinetics of butofilolol (CAFIDE) after repeated oral administration in man". International Journal of Clinical Pharmacology Research 4 (3): 175–83. 1984. PMID 6149195.
- ↑ "[Long-term hypotensive treatment by butofilolol]". Annales de Cardiologie et d'Angeiologie 32 (4): 277–83. June 1983. PMID 6412614.
- ↑ "4-fluorophenol: A key intermediate for agrochemicals and pharmaceuticals". The Roots of Organic Development. Industrial Chemistry Library. 8. 1996. pp. 293–300. doi:10.1016/S0926-9614(96)80020-7. ISBN 978-0-444-82434-9.
- ↑ "Butofilolol". Drugs of the Future 7 (2): 96. 1982. doi:10.1358/dof.1982.007.02.199366.
- ↑ Demarne H, "ompositions for treatment of cardiovascular conditions associated with overproduction of catecholamines", US patent 4252825, issued 24 February 1981)
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