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【结 构 式】 
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【药物名称】 【化学名称】N-[2-(Cyclopentylmethylsulfanyl)-1(R)-[N-(4-methoxybenzyl)carbamoyl]ethyl]carbamic acid tert-butyl ester 【CA登记号】219624-92-7, 219624-97-2 (enantiomer) 【 分 子 式 】C22H34N2O4S 【 分 子 量 】422.59128 |
【开发单位】Ono (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Non-Opioid Analgesics, N-Type Calcium Channel Blockers |
合成路线1
Alkylation of L-cysteine (I) with cyclopentylmethyl methanesulfonate (II) produced the cysteine thioether (III). A tert-butoxycarbonyl group was subsequently introduced into the amino group of (III) by using di-tert-butyl dicarbonate and NaOH. The resultant N-Boc-cysteine thioether (V) was finally coupled with p-methoxybenzylamine (VI) by means of EDC and HOBt to furnish the corresponding amide.
| 【1】 Seko, T.; et al.; Structure-activity study and analgesic efficacy of amino acid derivatives as N-type calcium channel blockers. Bioorg Med Chem Lett 2001, 11, 16, 2067. |
| 【2】 Seko, T.; Kato, M. (Ono Pharmaceutical Co., Ltd.); Amino acid derivs.. EP 0997147; WO 9902146 . |
| 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) | 14643 | L-cysteine; (R)-2-Amino-3-mercaptopropionic acid | 52-90-4 | C3H7NO2S | 详情 | 详情 |
| (II) | 51117 | cyclopentylmethyl methanesulfonate | C7H14O3S | 详情 | 详情 | |
| (III) | 51118 | (2R)-2-amino-3-[(cyclopentylmethyl)sulfanyl]propionic acid | C9H17NO2S | 详情 | 详情 | |
| (IV) | 51119 | (2R)-2-[(tert-butoxycarbonyl)amino]-3-[(cyclopentylmethyl)sulfanyl]propionic acid | C14H25NO4S | 详情 | 详情 | |
| (V) | 15908 | 3-methoxy-2,6-dimethyl-4(1H)-pyridinone | C8H11NO2 | 详情 | 详情 |