Mesulergine hydrochloride, CU-32085, CQ-32085, -Drug Synthesis Database

【结构式】

【药物名称】Mesulergine hydrochloride, CU-32085, CQ-32085

【化学名称】N'-(1,6-Dimethylergolin-8alpha-yl)-N,N-dimethylsulfamide monohydrochloride
　　　　　　1,6-Dimethyl-8alpha-(N,N-dimethylsulfamoylamino)ergoline monohydrochloride
　　　　　　N'-[(8alpha)-1,6-Dimethylergolin-8-yl]-N,N-dimethylsulfamide monohydrochloride

【CA登记号】72786-12-0, 64795-35-3 (free base)

【分子式】C₁₉H₂₈ClN₃O₂S

【分子量】397.97091

【开发单位】Novartis (Originator)

【药理作用】Antiparkinsonian Drugs, Extrapyramidal Disorders, Treatment of, NEUROLOGIC DRUGS, Dopamine Receptor Agonists

合成路线1

The hydrogenation of 1-methyl-7,8-lysergic acid ethyl ester (I) with H2 over PtO2 gives 1-methyl-9,10-dihydroisolysergic acid methyl ester (II), which by reaction with hydrazine is converted into the corresponding hydrazide (III). The reaction of (III) with NaNO2-HCl yields the expected azide (IV), which is submitted to a Curtius degradation by heating and hydrolysis to afford 1,6-dimethyl-8(alpha)-aminoergoline (V). Finally, this compound is treated with N,N-dimethylsulfamoyl chloride (VI) and 2,6-lutidine in methylene chloride.

参考文献中间体

【1】 Stuetz, P.; Fehr, T.; Stadler, P. (Novartis AG); Sulfonamido and sulfamoylamino-ergoline-I derivatives. BE 0849745; CA 1092100; CH 620441; DE 2656344; ES 454442; FR 2336135; GB 1567484; JP 7778900; NL 7614018 .
【2】 Serradell, M.N.; Koch, H.; Castaner, J.; Mesulergine Hydrochloride. Drugs Fut 1984, 9, 3, 191.

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)	30355	methyl 4,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylate		C₁₈H₂₀N₂O₂	详情	详情
(II)	30356	methyl 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate		C₁₈H₂₂N₂O₂	详情	详情
(III)	30357	4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbohydrazide		C₁₇H₂₂N₄O	详情	详情
(IV)	30358	4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbonyl azide		C₁₇H₁₉N₅O	详情	详情
(V)	30359	4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-ylamine; 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-amine		C₁₆H₂₁N₃	详情	详情
(VI)	30360	[(Chlorosulfonyl)(methyl)amino]methane;dimethylsulfamoyl chloride	13360-57-1	C₂H₆ClNO₂S	详情	详情

Extended Information