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【结 构 式】 
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【药物名称】BIIB-513 【化学名称】N2-[4-[4-(2-Furylcarbonyl)piperazin-1-yl]-3-(methylsulfonyl)benzoyl]guanidine methanesulfonate 【CA登记号】193401-08-0 (mono HCl salt) 【 分 子 式 】C19H25N5O8S2 【 分 子 量 】515.5678 |
【开发单位】Boehringer Ingelheim (Originator) 【药理作用】Angina pectoris, Treatment of, Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Na+/H+ Exchange type 1 (NHE-1) Inhibitors |
合成路线1
Condensation of N-(2-furanylcarbonyl)piperazine (I) with 4-chloro-3-(methylsulfonyl)benzoic acid (II) at 120 C produced the disubstituted piperazine (III). After activation of the carboxy group as the imidazolide (IV) upon treatment with 1,1'-carbonyldiimidazole and N-methylmorpholine, treatment with guanidine hydrochloride (V) and NaH in hot DMF yielded the corresponding benzoyl guanidine, which was finally isolated as the methanesulfonate salt.
| 【1】 Burger, E.; Eickmeier, C.; Roos, O. (Boehringer Ingelheim GmbH); Novel benzoyl guanidine derivs., process for their preparation and their use in the preparation of medicines. DE 19601303; EP 0882031; JP 2000503309; US 6114335; WO 9726253 . |
| 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) | 30751 | 2-furyl(1-piperazinyl)methanone; 2-Furoyl-1-piperazine | 40172-95-0 | C9H12N2O2 | 详情 | 详情 |
| (II) | 37884 | 4-chloro-3-(methylsulfonyl)benzoic acid | C8H7ClO4S | 详情 | 详情 | |
| (III) | 37885 | 4-[4-(2-furoyl)-1-piperazinyl]-3-(methylsulfonyl)benzoic acid | C17H18N2O6S | 详情 | 详情 | |
| (IV) | 37886 | 2-furyl[4-[4-(1H-imidazol-1-ylcarbonyl)-2-(methylsulfonyl)phenyl]-1-piperazinyl]methanone | C20H20N4O5S | 详情 | 详情 | |
| (V) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |