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【结 构 式】 
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【药物名称】KRN-2391 【化学名称】N-Cyano-N'-(2-nitrooxyethyl)-3-pyridinecarboxamidine monomethanesulfonate 【CA登记号】134431-49-5, 133299-87-3 (free base), 143966-31-8 (mono(4-p-tosylate)), 143966-32-9 (monobenzenesulfonate), 143966-37-4 (monoHCl 【 分 子 式 】C10H13N5O6S 【 分 子 量 】331.30901 |
【开发单位】Kirin Brewery (Originator) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Vasodilators, Potassium Channel Activators |
合成路线1
The synthesis used for the preparation of KRN2391 is as follows: The reaction of 3-cyanopyridine (I) with alcohol (ROH) in the presence of catalytic amount of alkoxide (NaOR) gives the imidate (II). The imidate (II) is converted to the cyanoimidate (III) by treatment with cyanamide in an aqueous phosphate buffer solution. The cyanoimidate (III) is coupled without further purification with nitroxyethylamine which is pre-prepared in situ from its hydrochloride (IV) and NaOH in water to provide the cyanoamidine (V). Finally, KRN2391 is obtained by salt formation of the cyanoamidine (V) with methanesulfonic acid.
| 【1】 Ogawa, N.; Izawa, T.; KRN2391. Drugs Fut 1994, 19, 6, 546. |
| 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) | 14062 | Nicotinonitrile; 3-Cyanopyridine | 100-54-9 | C6H4N2 | 详情 | 详情 |
| (II) | 14063 | methyl 3-pyridinecarboximidoate | C7H8N2O | 详情 | 详情 | |
| (III) | 14064 | methyl N-cyano-3-pyridinecarboximidoate | C8H7N3O | 详情 | 详情 | |
| (IV) | 14065 | N'-Cyano-N-[2-(nitrooxy)ethyl]-3-pyridinecarboximidamide | C9H9N5O3 | 详情 | 详情 |