Terfenadine, MDL-9918, RMI-9918, Seldane-D, Seldane, Triludan, Teldane, -Drug Synthesis Database

【结构式】

【药物名称】Terfenadine, MDL-9918, RMI-9918, Seldane-D, Seldane, Triludan, Teldane

【化学名称】alpha-(4-tert-Butylphenyl)-4-(alpha-hydroxy-alpha-phenylbenzyl)-1-piperidinebutanol

【CA登记号】50679-08-8

【分子式】C₃₂H₄₁NO₂

【分子量】471.68907

【开发单位】Aventis Pharma (Originator)

【药理作用】Drugs for Allergic Rhinitis, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders, Histamine H1 Antagonists

合成路线1 合成路线2

合成路线1

By condensation of alpha,alpha-diphenyl-4-piperidinemethanol (I) with 1-(p-tert-butylphenyl)-4-chlorobutanol (II) by means of KHCO3 and KI in refluxing toluene.

参考文献中间体

【1】 Thorpe, P.; Castaner, J.; Terfenadine. Drugs Fut 1978, 3, 3, 220.
【2】 Carr, A.A.; Kinsolving, C.R. (Aventis Pharmaceuticals, Inc.); Olefinic 4-substituted piperidino deriatives. ES 410732; FR 2181689; GB 1413140; JP 48085579; US 3862173 .
【3】 Carr, A.A.; Kinsolving, C.R. (Aventis Pharmaceuticals, Inc.); 1-Aroylalkyl-4-diphenylmethyl piperidines. DE 2303305; ES 410730; FR 2181692; GB 1412605; JP 48085576; US 3806526 .

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)	17178	diphenyl(4-piperidinyl)methanol; alpha,alpha-Diphenyl-4-piperidinomethanol; Azacyclonol	115-46-8	C₁₈H₂₁NO	详情	详情
(II)	39796	1-[4-(tert-butyl)phenyl]-4-chloro-1-butanol		C₁₄H₂₁ClO	详情	详情

合成路线2

1) By condensation of 4-methoxybenzylamine (I) with N,N',S-trimethylisothiourea hydroiodide (C) in refluxing ethanol, followed by treatment with H2SO4.

参考文献中间体

【1】 Thorpe, P.; Castaner, J.; Terfenadine. Drugs Fut 1978, 3, 3, 220.
【2】 Carr, A.A.; Kinsolving, C.R. (Aventis Pharmaceuticals, Inc.); 1-Aroylalkyl-4-diphenylmethyl piperidines. DE 2303305; ES 410730; FR 2181692; GB 1412605; JP 48085576; US 3806526 .
【3】 Carr, A.A.; Kinsolving, C.R. (Aventis Pharmaceuticals, Inc.); Olefinic 4-substituted piperidino deriatives. ES 410732; FR 2181689; GB 1413140; JP 48085579; US 3862173 .

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)	17179	2-[4-(4-[4-[hydroxy(diphenyl)methyl]-1-piperidinyl]butanoyl)phenyl]-2-methylpropyl acetate	76811-96-6	C₃₄H₄₁NO₄	详情	详情
(III)	12077	4-Chloro-1-[4-(1,1-dimethylethyl)phenyl]-1-butanone; 1-[4-(tert-Butyl)phenyl]-4-chloro-1-butanone; 4'-tert-Butyl-4-chlorobutyrophenone	43076-61-5	C₁₄H₁₉ClO	详情	详情
(IV)	39797	1-[4-(tert-butyl)phenyl]-4-[4-[hydroxy(diphenyl)methyl]-1-piperidinyl]-1-butanone		C₃₂H₃₉NO₂	详情	详情

Extended Information