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【结 构 式】

【药物名称】

【化学名称】6-Chloro-5-(methylsulfanyl)-N-(3-pyridyl)indoline-1-carboxamide

【CA登记号】

【 分 子 式 】C15H14ClN3OS

【 分 子 量 】319.81533

【开发单位】GlaxoSmithKline (Originator)

【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT2C (5-HT1C) Antagonists

合成路线1

The heating of nicotinoyl azide (I) in refluxing toluene gives the corresponding isocyanate (II), which without isolation is condensed with 6-chloro-5-(methylsulfanyl)indoline (IV) to afford the target compound. Intermediate indoline (IV) is obtained by reduction of 6-chloro-5-(methylsulfanyl)indole (III) with NaBH3CN in HOAc.

1 Ham, P.; Jones, G.E.; Forbes, I.T. (SmithKline Beecham plc); Indoline derivs. as 5HT2C antagonists. EP 0707581; JP 1996512299; US 5834494; WO 9501976 .
2 Davies, D.T.; Bromidge, S.M.; Dabbs, S.; et al.; Model studies on a synthetically facile series of N-substituted phenyl-N'-pyridin-3-yl ureas leading to 1-(3-pyridylcarbamoyl)indolines that are potent and selective 5-HT2C/2B receptor antagonists. Bioorg Med Chem 1999, 7, 12, 2767.
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) 13619 Nicotinoyl azide C6H4N4O 详情 详情
(II) 27045 3-isocyanatopyridine 15268-31-2 C6H4N2O 详情 详情
(III) 43774 6-chloro-5-(methylsulfanyl)-1H-indole; 6-chloro-1H-indol-5-yl methyl sulfide C9H8ClNS 详情 详情
(IV) 43775 6-chloro-5-(methylsulfanyl)indoline; 6-chloro-2,3-dihydro-1H-indol-5-yl methyl sulfide C9H10ClNS 详情 详情
Extended Information