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 . |
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