Sertaconazole nitrate, FI-7045(free base), Ertaczo, Ginedermofix, Zalain, Dermoseptic, Extens, Dermofix, Fisderm, -Drug Synthesis Database

【结构式】

【药物名称】Sertaconazole nitrate, FI-7045(free base), Ertaczo, Ginedermofix, Zalain, Dermoseptic, Extens, Dermofix, Fisderm

【化学名称】(R,S)-(±)-1-[2-(7-Chlorobenzo[b]thien-3-ylmethoxy)-2-(2,4-dichlorophenyl)ethyl]imidazole nitrate

【CA登记号】99592-39-9,583057-49-2，99592-32-2 (free base)

【分子式】C₂₀H₁₆Cl₃N₃O₄S

【分子量】500.79122

【开发单位】Ferrer (Originator), Robert Labs. (Originator), Mylan (Licensee)

【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY

合成路线1 合成路线2 合成路线3

合成路线1

参考文献中间体

【1】 Petschen I,Camps X. Sallares J. 2006. Process for preparation of eantiomeric imidazole derivatives. W0 200602981 1(本专利属于Ferrer Intemacional,S A, Spain)
【2】 Chen BQ，Zhao YS，Ma N，et al. 2002．Synthesis of sertaconazole nitrate. 发明专利申请公开说明书．CN 1358719(本专利属于Hebei Provincial Inst. of Pharmacy, Peop Rep China)
【3】 Raga M, Palacin C, Castello JM, et aL. 1986. New imidazole antifungal agents derived from benzo[b]tliophene. Eur J Med Chem．21: 329～332（本论文作者来自于Cent. Invest. Grupo Ferret，Barcelona, Spain)

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	14550	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanol; alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol; 1-(2',4'-Dichlorophenyl)-2-(1-imidazolyl)ethanol	24155-42-8	C₁₁H₁₀Cl₂N₂O	详情	详情
(II)	66697	(R)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol		C₁₁H₁₀Cl₂N₂O	详情	详情
(III)	66698	3,7-bis(chloromethyl)benzo[b]thiophene		C₁₀H₈Cl₂S	详情	详情

合成路线2

参考文献中间体

【1】 Foguet R, Ramentol J. Guglietta A. et al. 2003. Preparation of R-(一）-1-[2-(7-chlorobenzo.[b] thiophen-3-yl-methoxy)-2-(2,4-dichlorophenyl)-ethyl}lH-imidazole,i,e. R-(-)-sertaconuole, for the treatment of fungal infections．W0 2003068770(本专利属于Ferrer Intemacional S A，Spain)

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	32200	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanone	46503-52-0	C₁₁H₈Cl₂N₂O	详情	详情
(II)	66697	(R)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol		C₁₁H₁₀Cl₂N₂O	详情	详情
(III)	14551	3-(bromomethyl)-7-chloro-1-benzothiophene	17512-61-7	C₉H₆BrClS	详情	详情

合成路线3

Sertaconazole nitrate has been synthesized by condensation of 1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol (I) with 3-(bromomethyl)-7-chlorobenzo[b]thiophene (II) by means of NaH in HMPT, followed by salification with HNO3.

参考文献中间体

【1】 Moreno-Mañas, M.; Raga, M.M.; Palacín, C.; Ortiz, J.A.; Cuberes, M.R.; Castelló, J.M.; Synthesis and antimycotic activity of (benzo[b]thienyl)methyl ethers of 1 -(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol and of (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone oxime. Arzneim-Forsch Drug Res 1992, 42, 5a, 691.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	14550	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanol; alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol; 1-(2',4'-Dichlorophenyl)-2-(1-imidazolyl)ethanol	24155-42-8	C₁₁H₁₀Cl₂N₂O	详情	详情
(II)	14551	3-(bromomethyl)-7-chloro-1-benzothiophene	17512-61-7	C₉H₆BrClS	详情	详情

Extended Information