藥物詳細合成路線

Name	Fenticonazole nitrate;Rec-151476B free base;Rec-151476;Lomexin
Chemical Name	(±)-1-[2-(2,4-Dichlorophenyl)-2-[[4-(phenylthio)phenyl]methoxy]ethyl]-1H-imidazole mononitrate
CAS	73151-29-8
Related CAS	72479-26-6 (free base)
Formula	C24H21Cl2N3O4S
Structure
Formula Weight	518.42267
Stage	上市-1986
Company	Recordati (Originator), SK Pharma (Not Determined), Effik (Licensee), Gerot (Licensee), Pfizer (Licensee)
Activity/Mechanism	Antifungal Agents, ANTIINFECTIVE THERAPY
Syn. Route	1

Route 1 the reduction of 2,4-dichlorophenacyl chloride with nabh4 gives 1-(2,4-dichlorophenyl)-2-chloroethanol (ii), which is condensed with imidazole (iii) to yield 1-(2,4-dichlorophenyl)-2-(n-imidazolyl)ethanol (iv). finally, this compound is condensed with 4-(phenylthio)benzyl chloride (v) [prepared by chloromethylation of diphenyl sulfide (vi) with formaldehyde and hcl] using nah as condensing agent. List of intermediates No. (3r,4s)-1-(4-methoxyphenyl)-4-[(e)-1-propenyl]-3-[(triisopropylsilyl)oxy]-2-azetidinone (iii) 2-[(2,2-dimethylpropanoyl)amino]-4-isobutylphenylboronic acid (iv) benzyl (2s)-2-([[(2s,4r)-1-[(2s)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl]-4-(2-naphthylmethoxy)pyrrolidinyl]carbonyl]amino)pentanoate (vi) (3as,4r,6r,6ar)-4-methoxy-6-[(trityloxy)methyl]tetrahydro-2lambda(4)-furo[3,4-d][1,3,2]dioxathiol-2-one (i) (2r,3r,4s,5s)-4-azido-2-methoxy-5-[(trityloxy)methyl]tetrahydro-3-furanyl 4-methylbenzenesulfonate (ii) (2s,3s,4r,5r)-3-azido-5-methoxy-4-[[(4-methylphenyl)sulfonyl]oxy]tetrahydro-2-furancarboxylic acid (v) Reference 1:     cova, a.; tajana, a.; nardi, d.; cappelleti, r.; sibilia, c.; physico-chemical, structural and analytical studies on fenticonazole, a new drug with antimycotic properties. arzneim-forsch drug res 1981, 31, 12, 2127. Reference 2:     nardi, d.; massarani, e.; tajana, a.; veronese, m. (recordati industria chimica e farmaceutica spa); substituted dibenzyl ethers and parmaceutical compositions containing said ethers for the treatment of infections. de 2917244; fr 2426047; gb 2025395; us 4221803 . Reference 3:     blancafort, p.; castaner, j.; serradell, m.n.; fenticonazole nitrate. drugs fut 1983, 8, 9, 767.

來源:藥化網

作者:藥化小編

摘要:本文合成路線介紹的是藥物中文名硝酸芬替康唑；英文名Fenticonazole nitrate;Rec-151476B free base;Rec-151476;Lomexin；CAS[73151-29-8]

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