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【结 构 式】 
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【药物名称】BTS-74398 【化学名称】1-[1-(3,4-Dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino) propylsulfanyl]ethanone monocitrate 【CA登记号】 【 分 子 式 】C23H31Cl2NO8S 【 分 子 量 】552.47542 |
【开发单位】Knoll 【药理作用】NEUROLOGIC DRUGS, TREATMENT OF EXTRAPYRAMIDAL MOVEMENT DISORDERS |
合成路线1
Addition of methylmagnesium iodide to nitrile (I), followed by hydrolytic treatment, provided ketone (II), which was brominated in CHCl3-MeOH to give bromomethyl ketone (III). Alkylation of thiourea (V) with 3-(dimethylamino)propyl chloride (IV) produced S-alkyl isothiourea (VI). After hydrolysis of (VI) with NaOEt, the intermediate thiol (VII) was condensed with bromoketone (III) to yield the required thioether, which was finally converted to the citrate salt.
| 【1】 Harris, P.J.; Heal, D.J. (The Boots Company plc); 1-Arylcycloalkyl sulphides, sulphoxides and sulphones for the treatment of depression, anxiety and Parkinson's disease. EP 0715620; JP 1996510222; US 5652271; WO 9426704 . |
| 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) | 27478 | 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile | C11H9Cl2N | 详情 | 详情 | |
| (II) | 27479 | 1-[1-(3,4-dichlorophenyl)cyclobutyl]-1-ethanone | C12H12Cl2O | 详情 | 详情 | |
| (III) | 27480 | 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]-1-ethanone | C12H11BrCl2O | 详情 | 详情 | |
| (IV) | 24581 | 3-(Dimethylamino)propyl chloride; 3-Chloro-N,N-dimethyl-1-propanamine | 5407-04-5 | C5H12ClN | 详情 | 详情 |
| (V) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (VI) | 27481 | 1-[[amino(imino)methyl]sulfanyl]-3-(dimethylamino)propane | C6H15N3S | 详情 | 详情 | |
| (VII) | 27482 | N,N-Dimethyl-N-(3-sulfanylpropyl)amine sodium salt | C5H12NNaS | 详情 | 详情 |
Extended Information