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【结 构 式】 
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【药物名称】BPDZ-83 【化学名称】7-Chloro-3-(1,2,2-trimethylpropylamino)-4H-pyrido[2,3-e][1,2,4]thiadiazine 1,1-dioxide 【CA登记号】 【 分 子 式 】C12H17ClN4O2S 【 分 子 量 】316.81189 |
【开发单位】Université Libre de Bruxelles (Originator), University of Liege(Originator) 【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, K(ATP) Channel Activators |
合成路线1
2-Amino-5-chloropyridine-3-sulfonamide (II) was obtained by the reaction of 2-amino-5-chloropyridine (I) with chlorosulfonic acid, followed by treatment of the sulfonyl chloride intermediate with aqueous ammonia. Condensation of amino sulfonamide (II) with thiocarbonyldiimidazole (III) produced the imidazolyl pyridothiadiazine (IV). Nucleophilic substitution of the imidazolyl group with 1,2,2-trimethylpropylamine (V) in a sealed vessel at 180 C furnished the corresponding amino pyridothiadiazine.
| 【1】 de Tullio, P.; Quedraogo, R.; Pirotte, B.; et al.; 3-Alkylamino-4H-pyrido[2,3-e]-1,2,4-thiadiazine 1,1-dioxides structurally related to diazoxide and pinacidil as potassium channel openers acting on vascular smooth muscle cells: Design, synthesis, and pharmacological evaluation. J Med Chem 2000, 43, 8, 1456. |
| 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) | 18559 | 5-Chloro-2-pyridinylamine; 5-Chloro-2-pyridinamine; 2-Amino-5-chloropyridine | 1072-98-6 | C5H5ClN2 | 详情 | 详情 |
| (II) | 46289 | 2-amino-5-chloro-3-pyridinesulfonamide | C5H6ClN3O2S | 详情 | 详情 | |
| (III) | 11990 | Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole | 6160-65-2 | C7H6N4S | 详情 | 详情 |
| (IV) | 46290 | 7-chloro-3-(1H-imidazol-1-yl)-2H-pyrido[2,3-e][1,2,4]thiadiazine-1,1(4H)-dione | C9H6ClN5O2S | 详情 | 详情 | |
| (V) | 30977 | (2R)-3,3-dimethyl-2-butanamine; (1R)-1,2,2-trimethylpropylamine | C6H15N | 详情 | 详情 |