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【结 构 式】 
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【药物名称】Lazabemide hydrochloride, Ro-19-6327/001, Tempium, Pakio 【化学名称】N-(2-Aminoethyl)-5-chloropyridine-2-carboxamide hydrochloride 【CA登记号】103878-83-7, 103878-84-8 (free base) 【 分 子 式 】C8H11Cl2N3O 【 分 子 量 】236.10237 |
【开发单位】Chugai (Originator), Roche (Originator) 【药理作用】Antiparkinsonian Drugs, Cognition Disorders, Treatment of, Extrapyramidal Disorders, Treatment of, NEUROLOGIC DRUGS, Smoking Cessation, Aid to, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, MAO-B Inhibitors |
合成路线1
The reaction of 5-chloropyridine-2-carboxylic acid (I) with N-(2-aminoethyl)carbamic acid tert-butyl ester (II) by means of carbonyl-dimidazole (CDI) in refluxing THF gives N-[2-(tert-butoxycarbonylamino)ethyl]-5-chloropyridine-2-carboxamide (III), which is then hydrolyzed with trifluoroacetic acid in refluxing dichloromethane and treated with ethanolic HCl to obtain the hydrochloride.
| 【1】 Imhof, R.; Kyburz, E. (F. Hoffmann-La Roche AG); Ethylenediaminemonoamide derivs., pharmaceutical compsns. containing them and use of these cpds. As antidepressants or antiparkinsonians. AU 8546636; CH 661043; CH 664755; DE 3530046; ES 8705407; ES 8800158; FR 2569694; JP 1986060657; JP 1995300417; US 4764522 . |
| 【2】 Prous, J.; Castaner, J.; Lazabemide Hydrochloride. Drugs Fut 1993, 18, 2, 113. |
| 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) | 13240 | 5-Chloro-2-pyridinecarboxylic acid | C6H4ClNO2 | 详情 | 详情 | |
| (II) | 13241 | N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate；tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate | 57260-73-8 | C7H16N2O2 | 详情 | 详情 |
| (III) | 13242 | tert-butyl 2-[[(5-chloro-2-pyridinyl)carbonyl]amino]ethylcarbamate | C13H18ClN3O3 | 详情 | 详情 |