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【结 构 式】 
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【药物名称】Pibutidine hydrochloride, IT-066 【化学名称】3-Amino-4-[4-[4-(1-piperidinylmethyl)-2-pyridyloxy]-2(Z)-butenylamino]-3-cyclobutene-1,2-dione hydrochloride 【CA登记号】126463-66-9, 103922-33-4 (free base) 【 分 子 式 】C19H25ClN4O3 【 分 子 量 】392.8891 |
【开发单位】Ikeda Mohando (Originator), Taisho (Codevelopment) 【药理作用】Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS, Histamine H2 Receptor Antagonists |
合成路线1
The condensation of 4-amino-2(Z)-buten-1-ol (I) with 2-bromo-4-(piperidinomethyl)pyridine (II) by means of NaH in refluxing THF gives 4-[4-(piperidinomethyl)pyridin-2-yloxy]-2(Z)-butenylamine (III), which is allowed to react with 3,4,-dimethoxy-3-cyclobutene-1,2-dione (IV) in methanol to afford 3-methoxy-4-[4-[4-(piperidinomethyl)pyridin-2-yloxy]-2(Z)-butenylamino]-3-cyclobutene-1,2-dione (V). Finally, this compound is treated with dry ammonia in methanol.
| 【1】 Nohara, F.; Fujinawa, T. (Ikeda Mohando); Pyridyloxy derivs.. AU 8548136; EP 0177016; ES 8701161; JP 1986085365; JP 1986207375; JP 1991261766; US 4710498 . |
| 【2】 Prous, J.; Castaner, J.; IT-066. Drugs Fut 1990, 15, 12, 1181. |
| 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) | 13022 | (Z)-4-Amino-2-buten-1-ol | C4H9NO | 详情 | 详情 | |
| (II) | 13021 | 2-Bromo-4-(1-piperidinylmethyl)pyridine | C11H15BrN2 | 详情 | 详情 | |
| (III) | 13023 | (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-amine; (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-butenylamine | C15H23N3O | 详情 | 详情 | |
| (IV) | 19999 | 3,4-dimethoxy-3-cyclobutene-1,2-dione | 5222-73-1 | C6H6O4 | 详情 | 详情 |
| (V) | 31233 | 3-methoxy-4-[((Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl)amino]-3-cyclobutene-1,2-dione | C20H25N3O4 | 详情 | 详情 |