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【结 构 式】 
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【药物名称】KW-3196 【化学名称】5-Deoxy-2-O-nitro-5-[4-(pyridin-3-ylcarbonyl)piperazin-1-yl]-1,4:3,6-dianhydro-L-iditol 【CA登记号】134186-21-3 【 分 子 式 】C16H20N4O6 【 分 子 量 】364.361 |
【开发单位】Kyowa Hakko (Originator) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis |
合成路线1
The preparation of KW-3196 is as follows: Reaction of 1,4:3,6-dianhydro-D-glucitol 5-methanesulfonate (I) (1) with piperazine (II) afforded (III), which was nitrated with fuming HNO3 to give the nitrate ester (IV). Nicotynoylation of (IV) gave KW-319).
| 【1】 Klessing, K.; Chatterjee, S.S. (Dr. Willmar Schwabe); Alkylaminodeoxy-1,4:3,6-dianhydrohexitol nitrates substituted by purine bases and their pharmaceutical compositions. EP 0044927 . |
| 【2】 Suzuki, F.; Hayashi, H.; Kuroda, T.; Kubo, K.; Ikeda, J. (Kyowa Hakko Kogyo Co., Ltd.); Hexitol derivatives having vasodilative activity. EP 0393574; JP 1991218381; US 5053408 . |
| 【3】 Ueno, H.; Hayashi, H.; Suzuki, F.; Synthesis of stereoisomers of 1,4:3,6-dianhydrohexitol nitrate derivative, KF14124. Bioorg Med Chem Lett 1992, 2, 1187-92. |
| 【4】 Suzuki, F.; KW-3196. Drugs Fut 1992, 17, 11, 995. |
| 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) | 14844 | (3R,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl methanesulfonate | C7H12O6S | 详情 | 详情 | |
| (II) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
| (III) | 14845 | (3S,3aR,6S,6aR)-6-piperazinohexahydrofuro[3,2-b]furan-3-ol | C10H18N2O3 | 详情 | 详情 | |
| (IV) | 14846 | 1-[(3S,3aR,6S,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl]piperazine | C10H17N3O5 | 详情 | 详情 | |
| (V) | 10753 | Nicotinoyl chloride | C6H4ClNO | 详情 | 详情 |
Extended Information