|
【结 构 式】 
|
【药物名称】Talsaclidine fumarate, WAL-2014-FU 【化学名称】3(R)-(2-Propynyloxy)-1-azabicyclo[2.2.2]octane fumarate 【CA登记号】147025-54-5, 147025-53-4 (free base), 129508-81-2 (undefined isomer) 【 分 子 式 】C14H19NO5 【 分 子 量 】281.31123 |
【开发单位】Boehringer Ingelheim (Originator) 【药理作用】Alzheimer's Dementia, Treatment of , Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Muscarinic M1 Agonists |
合成路线1
The condensation of 3-hydroxy-1-azabicyclo[2.2.2]octan borane complex (I) with 2-propynyl bromide (II) by means of NaH in DMF gives racemic 3-(2-propynyloxy)-1-azabicyclo[2.2.2]octane (III), which is then submitted to optical resolution with (+)- or (-)-dibenzoyltartaric acid. The optically pure tartrates are treated with aqueous K2CO3 and finally with fumaric acid to obtain the optically pure fumarates.
| 【1】 Walther, G.; Weber, K.-H.; Stransky, W.; Kuhn, F.; Müller, E.; Ensinger, H. (Boehringer Ingelheim GmbH); Novel quinuclidines, their pharmaceutical use and process for their preparation. AU 8945403; DE 3839385; EP 0370415; JP 1990243688; US 5286864; US 5451587 . |
| 【2】 Mealy, N.; Prous, J.; Castaner, J.; WAL-2014-FU. Drugs Fut 1994, 19, 1, 35. |