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【结 构 式】 
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【药物名称】SM-10661(racemate), SM-12502 【化学名称】(+)-cis-(2R,5S)-3,5-Dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride 【CA登记号】119383-00-5, 130841-70-2 (racemate) 【 分 子 式 】C10H13ClN2OS 【 分 子 量 】244.74491 |
【开发单位】Sumitomo Pharmaceuticals (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Treatment of Septic Shock, Platelet-Activating Factor (PAF) Antagonists |
合成路线1
Methylation of methyl (+)-lactate (I) followed by thioacetylation and acidic hydrolysis affords (-)-thiolactic acid (IV). Reaction of 3-pyridinecarboxyaldehyde (V) with methylamine in toluene under the azeotropic condition provides the imine (VI), which when condensed with (IV) affords (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one (VII). Treatment of (VII) with aqueous HCl/isopropanol results in the precipitation of SM-12502.
| 【1】 Koike, H.; Natsume, Y.; Tojo, S.; Morooka, S.; SM-12502. Drugs Fut 1995, 20, 2, 153. |
| 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) | 11591 | methyl (2R)-2-hydroxypropanoate | 17392-83-5 | C4H8O3 | 详情 | 详情 |
| (II) | 16679 | methyl (2R)-2-[(methylsulfonyl)oxy]propanoate | C5H10O5S | 详情 | 详情 | |
| (III) | 16680 | methyl (2S)-2-(acetylsulfanyl)propanoate | C6H10O3S | 详情 | 详情 | |
| (IV) | 16681 | (2S)-2-sulfanylpropionic acid | C3H6O2S | 详情 | 详情 | |
| (V) | 12849 | Nicotinaldehyde; 3-Pyridinecarboxaldehyde | 500-22-1 | C6H5NO | 详情 | 详情 |
| (VI) | 16683 | N-methyl-N-[(Z)-3-pyridinylmethylidene]amine; N-[(Z)-3-pyridinylmethylidene]methanamine | C7H8N2 | 详情 | 详情 | |
| (VII) | 16684 | (2R,5S)-3,5-dimethyl-2-(3-pyridinyl)-1,3-thiazolan-4-one | C10H12N2OS | 详情 | 详情 |