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【结 构 式】

【药物名称】Lergotrile

【化学名称】2-[(6aR,9S,10aR)-5-Chloro-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]acetonitrile

【CA登记号】36945-03-6

【 分 子 式 】C17H18ClN3

【 分 子 量 】299.80611

【开发单位】Lilly

【药理作用】Antiparkinsonian Drugs, Extrapyramidal Disorders, Treatment of, NEUROLOGIC DRUGS, Prolactin Secretion Inhibitors

合成路线1

It is prepared in two different ways, both starting from 6-methyl-8-methanesulfonyloxymethylergolin (II), m.p. 192-4 C, prepared by reaction of the corresponding hydroxy compound (I) with methanesulfonyl chloride in pyridine: 1) The starting product (II) is first chlorinated with N-chlorosuccinimide (A) in dioxane to 2-chloro-6-methyl-8-methanesulfonyloxymethylergolin (III), which is then treated with sodium cyanide in DMSO. 2) The starting product (II) is first treated with sodium cyanide in DMSO to give 6-methyl-8-cyanomethylergolin (IV), which is then chlorinated with N-chlorosuccinimide (A) in dioxane.

1 Castañer, J.; Chatterjee, S.S.; Lergotrile. Drugs Fut 1976, 1, 2, 63.
2 Clemens, J.A.; et al. (Eli Lilly and Company); D-6-methyl-2,8-disubstituted ergolines. DE 2335750; ES 446789; FR 2193606; GB 1423065; JP 57081487 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 40429 Succinchlorimide; N-Chlorosuccinimide; 1-chloro-2,5-pyrrolidinedione 128-09-6 C4H4ClNO2 详情 详情
(I) 10051 [(6aR,9R,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methanol; 9,10-Dyhydrosergol 18051-16-6 C16H20N2O 详情 详情
(II) 40428 (6aR,9R,10aR)-7-methyl-9-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline C19H26N2OS 详情 详情
(III) 40430 (6aR,9R,10aR)-5-chloro-7-methyl-9-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline C19H25ClN2OS 详情 详情
(IV) 40431 2-[(6aR,9S,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]acetonitrile C17H19N3 详情 详情
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