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【结 构 式】 
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【药物名称】WAY-100289 【化学名称】endo-2-(Cyclopropylmethoxy)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylcarbamoyl)benzamide maleate 【CA登记号】136013-69-9 【 分 子 式 】C24H31N3O7 【 分 子 量 】473.53057 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】Anxiolytics, Nausea and Vomiting, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, 5-HT3 Antagonists |
合成路线1
The reaction of salicylamide (I) with cyclopropylmethyl bromide in the presence of potassium hydroxide gives the ether (II). This intermediate is converted to the benzoyl isocyanate (III) by refluxing with oxalyl chloride in 1,2-dichloroethane. The isocyanate is converted without further purification to endo-2-(cyclopropylmethoxy)-N-[[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl) amino]-carbonyl]benzamide (WAY100289) by reaction with endo-3-aminotropane.
| 【1】 Ward, T.J.; White, J.C.; Bradley, G. (John Wyeth & Brother Ltd.); Aroyl-ureas. AU 9163749; EP 0422846; GB 2236528; JP 1991133986 . |
| 【2】 Ward, T.J.; Taylor, A.; White, J.C.; Coleman, J.; Bradley, G.; Rhodes, K.F.; Novel antagonists of the 5-HT3 receptor. Synthesis and structure activity relationships of (2-alkoxybenzoyl)ureas. J Med Chem 1992, 35, 9, 1515-9. |
| 【3】 Ward, T.J.; WAY 100289. Drugs Fut 1993, 18, 1, 23. |