Amiprilose, SM-1213, Therafectin, -Drug Synthesis Database

【结构式】

【药物名称】Amiprilose, SM-1213, Therafectin

【化学名称】3-O-[3-(Dimethylamino)propyl]-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose
　　　　　　1,2-O-Isopropylidene-3-O-[3'-(N,N-dimethylamino)propyl]-D-glucofuranose

【CA登记号】56824-20-5, 60414-06-4 (HCl)

【分子式】C₁₄H₂₇NO₆

【分子量】305.37439

【开发单位】Boston Life Sciences (Originator), Kissei (Licensee)

【药理作用】Antiarthritic Drugs, IMMUNOMODULATING AGENTS, Immunomodulators, Rheumatoid Arthritis, Treatment of, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES

合成路线1

The reaction of 1,2:5.6-di-O-isopropyliden-D-glucofuranose (I) with 3-chloro-N,N-dimethylaminopropane (II) by means of NaOH in refluxing dioxane gives 1,2:5,6-di-O-isopropylidene-3-O-[3'-(N,N-dimethylamino)propyl]-D-gluco-furanose (III), which is partially hydrolyzed with HCl in water.

参考文献中间体

【1】 Gordon, P. (Boston Life Sciences, Inc.); Method of enhancing learning and/or memory in warm blooded animals. US 3965262 .
【2】 Hopkins, S.J.; Serradell, M.N.; Castaner, J.; Therafectin. Drugs Fut 1985, 10, 4, 301.

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)	29141	(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol	582-52-5	C₁₂H₂₀O₆	详情	详情
(II)	24581	3-(Dimethylamino)propyl chloride; 3-Chloro-N,N-dimethyl-1-propanamine	5407-04-5	C₅H₁₂ClN	详情	详情
(III)	29142	3-([(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy)-N,N-dimethyl-1-propanamine		C₁₇H₃₁NO₆	详情	详情

Extended Information