【药物名称】Topiramate, KW-6485, RWJ-17021-000, McN-4853, Epitomax, Topamax Sprinkle, Topamax, Topimax
化学结构式(Chemical Structure):
参考文献No.85087
标题:TOPIRAMATE < Rec INN; USAN >
作者:Maryanoff, B.D.; Margul, B.L.
来源:Drugs Fut 1989,14(4),342
合成路线图解说明:

Topiramate is synthesized by two methods: D-Fructose, an abundant and inexpensive monosaccharide, is reacted with acetone to produce the thermodynamically more stable bisacetonide (I). This bisacetonide is then condensed with sulfamoyl chloride in the presence of sodium hydride. Alternatively, intermediate (I) is reacted with sulfuryl chloride and pyridine in methylene chloride and then with sodium azide in acetonitrile to furnish azido sulfate (II), which is reduced with copper powder in methanol.

参考文献No.106272
标题:Anticonvulsant O-alkyl sulfamates. 2,3:4, 5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate and related compounds
作者:Maryanoff, B.E.; Nortey, S.O.; Gardocki, J.F.; Shank, R.P.; Dodgson, S.P.
来源:J Med Chem 1987,30880-7
合成路线图解说明:

Topiramate is synthesized by two methods: D-Fructose, an abundant and inexpensive monosaccharide, is reacted with acetone to produce the thermodynamically more stable bisacetonide (I). This bisacetonide is then condensed with sulfamoyl chloride in the presence of sodium hydride. Alternatively, intermediate (I) is reacted with sulfuryl chloride and pyridine in methylene chloride and then with sodium azide in acetonitrile to furnish azido sulfate (II), which is reduced with copper powder in methanol.

参考文献No.900158
标题:Anticonvulsant sulfamate derivatives.
作者:Maryanoff, B.E.; Gardocki, J.F. (McNeilab, Inc.)
来源:EP 0138441; JP 5331132; US 4513006
合成路线图解说明:

Topiramate is synthesized by two methods: D-Fructose, an abundant and inexpensive monosaccharide, is reacted with acetone to produce the thermodynamically more stable bisacetonide (I). This bisacetonide is then condensed with sulfamoyl chloride in the presence of sodium hydride. Alternatively, intermediate (I) is reacted with sulfuryl chloride and pyridine in methylene chloride and then with sodium azide in acetonitrile to furnish azido sulfate (II), which is reduced with copper powder in methanol.

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