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【结 构 式】 
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【药物名称】Anpirtoline hydrochloride, D-16949 【化学名称】4-(6-Chloropyridin-2-ylsulfanyl)piperidine hydrochloride 【CA登记号】99201-87-3, 98330-05-3 (free base) 【 分 子 式 】C10H14Cl2N2S 【 分 子 量 】265.20648 |
【开发单位】Degussa (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antidepressants, Mood Disorders, Treatment of, Non-Opioid Analgesics, PSYCHOPHARMACOLOGIC DRUGS, 5-HT1B Agonists |
合成路线1
2,6-Dichloropyridine (I) reacts with sodium hydrogen sulfide yielding 6-chloro-2-mercaptopyridine sodium salt (II). The thioether (III) is formed through reaction of 4-chloro-N-methylpiperidine with (II). Cleavage of the N-methyl group is achieved by condensation of (III) with ethyl chloroformate followed by acidic hydrolysis.
| 【1】 Engel, J.; Jacovlev, V.; Nickel, B.; Scheffler, G.; Thiemer, K. (Degussa-Hüls AG); New pyridine-2-ethers and pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring. DE 3443968; EP 0149088; ES 8607014; GB 2152048; JP 1985169476; US 4643995 . |
| 【2】 Szelenyi, I.; Engel, J.; Scheffler, G.; Nickel, B.; Thiemer, K.; Tibes, U.; Werner, U.; ANPIRTOLINE HYDROCHLORIDE < Rec INNM >. Drugs Fut 1989, 14, 7, 614. |
| 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) | 13573 | 2,6-Dichloropyridine | 2402-78-0 | C5H3Cl2N | 详情 | 详情 |
| (II) | 20947 | 6-Chloropyridine-2-thiol sodium salt | C5H3ClNNaS | 详情 | 详情 | |
| (III) | 20948 | 6-chloro-2-pyridinyl 1-methyl-4-piperidinyl sulfide; 4-[(6-chloro-2-pyridinyl)sulfanyl]-1-methylpiperidine | C11H15ClN2S | 详情 | 详情 | |
| (IV) | 20949 | 4-Chloro-1-methylpiperidine; 4-Chloro-N-methylpiperidine; N-methyl-4-chloropiperidine | 55770-77-4 | C6H12ClN | 详情 | 详情 |
| (V) | 20950 | ethyl 4-[(6-chloro-2-pyridinyl)sulfanyl]-1-piperidinecarboxylate | C13H17ClN2O2S | 详情 | 详情 |