药物详细合成路线

Name	Ciclopirox olamine;HOE-296;Ciclochem;Penlac nail lacquer;Mycoster;Batrafen;Loprox
Chemical Name	6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone 2-aminoethanol
CAS	41621-49-2
Related CAS	29342-05-0 (free base)
Formula	C14H24N2O3
Structure
Formula Weight	268.35898
Stage	上市-1982
Company	Aventis Pharma (Originator), Pierre Fabre (Not Determined), Ferrer (Licensee)
Activity/Mechanism	Antifungal Agents, ANTIINFECTIVE THERAPY
Syn. Route	1

Route 1 compound can be prepared in two different ways:1) the reaction of methyl 5-oxo-5-cyclohexyl-3-methylpentenoate (i) with nh2oh gives the corresponding oxime (ii), which is then cyclized to 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridone (iii). finally, this compound is salified with ethanolamine (iv).2) compound (iii) can also be obtained by reaction of 6-cyclohexyl-4-methyl-2-pyron (v) with hydroxylamine hydrochloride in hot 2-aminopyridine. List of intermediates No. (3s,5r)-8,8-dibromo-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-7-octen-2-one (i) (2s,4r)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-1-methylene-6-heptynyl trifluoromethanesulfonate (ii) methyl 2-((3s,5r)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)acetate (iii) methyl 2-((3s,5r)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)acetate (iv) Reference 1:     matsumoto, y.; et al.; drugs today 1974, 10, 1, 35. Reference 2:     blancafort, p.; serradell, m.n.; hopkins, s.j.; castaner, j.; ciclopirox olamine. drugs fut 1979, 4, 11, 795. Reference 3:     lohaus, g.; dittmar, w.; us 3972888 . Reference 4:     lohaus, g.; dittmar, w.; za 6906039 .

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名环吡司胺；英文名Ciclopirox olamine;HOE-296;Ciclochem;Penlac nail lacquer;Mycoster;Batrafen;Loprox；CAS[41621-49-2]

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