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【结 构 式】 
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【药物名称】YM-268 【化学名称】5,5'-Methylenebis(1,4-phenylene)bismethylenebis(thiazolidine-2,4-dione) 【CA登记号】141716-96-3 【 分 子 式 】C21H18N2O4S2 【 分 子 量 】426.51661 |
【开发单位】Yamanouchi (Originator) 【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS, Insulin Sensitizers, PPARgamma Agonists |
合成路线1
Diazotization of 4,4'-diaminodiphenylmethane (I) with NaNO2 and HCl, followed by copper-catalyzed coupling with methyl acrylate afforded the alpha,alpha'-dichloro diester (II). Subsequent cyclization of (II) with thiourea (III) in refluxing EtOH produced the bis(iminothiazolidinone) (IV). Finally, acid hydrolysis of (IV) yielded the title compound.
| 【1】 Niigata, K.; Takahashi, T.; Iwaoka, K.; Yoneda, T.; Noshiro, O.; Koike, R. (Yamanouchi Pharmaceutical Co., Ltd.); Bisheterocyclic cpd.. EP 0533933; JP 1992511153; WO 9200967 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 | |
| (I) | 36325 | 4-(4-aminobenzyl)phenylamine; 4-(4-aminobenzyl)aniline | 101-77-9 | C13H14N2 | 详情 | 详情 |
| (II) | 36324 | methyl 2-chloro-3-[4-[4-(2-chloro-3-methoxy-3-oxopropyl)benzyl]phenyl]propanoate | C21H22Cl2O4 | 详情 | 详情 | |
| (III) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (IV) | 36326 | 2-imino-5-(4-[4-[(2-imino-4-oxo-1,3-thiazolidin-5-yl)methyl]benzyl]benzyl)-1,3-thiazolidin-4-one | C21H20N4O2S2 | 详情 | 详情 |
Extended Information