Repirinast, MY-5116, Romet
瑞吡司特Chemical Name: 7,8-Dimethyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-2-carboxylic acid 3-methylbutyl ester
CAS No. 73080-51-0
项目整合开发状态: Launched-1987
项目研究机构: Mitsubishi Chemical (Originator), Mitsubishi Pharma (Originator), Nikken Chemicals (Originator)
合成路线:1) The cyclization of 2,3-dimethylaniline (I) with diethyl acetylmalonate (II) in 1-chloronaphthalene at 240 C gives 3-acetyl-4-hydroxy-7,8-dimethylquinolin-2(1H)-one (III),which by reaction with diethyl oxalate (IV) by means of sodium ethoxide in refluxing benzene yields ethyl-4-(4-hydroxy-7,8-dimethyl-2-oxo-1,2-dihydroquinolin-3yl)-2,4-dioxo-butanoate (V).The cyclization of (V) in acetic acid concentrated HCl at 100 C affords 5,6-dihydro-7,8 dimethyl-4,5-dioxo-4H-pyrano[3,2-c]quinoline-2-carboxylic acid (VI),which is converted into the corresponding acyl chloride (VII) by reaction with refluxing SOCl2.Finally,this compound is treated with hot 3-methylbutanol (VIII).
合成路线:2) The condensation of quinolone (III) with 3 methylbutyl oxalate (X) [obtained from 3 methyl butanol (VIII) and oxalic acid (IX)] by means of NaH yields 3-methylbutyl-4-(4 hydroxy-7,8-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)-2,4-dioxobutanoate (XI),which is then cyclized by means of sulfuric acid.([*]-labeled compound).
📌 参考资料/链接：
参考文献标题:Repirinast
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1987,12(1),37
📄 详细内容
合成路线:1) The cyclization of 2,3-dimethylaniline (I) with diethyl acetylmalonate (II) in 1-chloronaphthalene at 240 C gives 3-acetyl-4-hydroxy-7,8-dimethylquinolin-2(1H)-one (III),which by reaction with diethyl oxalate (IV) by means of sodium ethoxide in refluxing benzene yields ethyl-4-(4-hydroxy-7,8-dimethyl-2-oxo-1,2-dihydroquinolin-3yl)-2,4-dioxo-butanoate (V).The cyclization of (V) in acetic acid concentrated HCl at 100 C affords 5,6-dihydro-7,8 dimethyl-4,5-dioxo-4H-pyrano[3,2-c]quinoline-2-carboxylic acid (VI),which is converted into the corresponding acyl chloride (VII) by reaction with refluxing SOCl2.Finally,this compound is treated with hot 3-methylbutanol (VIII).
参考文献标题:Antiallergic agents I.Pyranoquinoline derivatives
文献作者:Takahashi,K.; Hata,S.; Morinaka,Y.; Yamada,S.
参考来源:Eur J Med Chem - Chim Ther 1981,16(3),251
合成路线:2) The condensation of quinolone (III) with 3 methylbutyl oxalate (X) [obtained from 3 methyl butanol (VIII) and oxalic acid (IX)] by means of NaH yields 3-methylbutyl-4-(4 hydroxy-7,8-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)-2,4-dioxobutanoate (XI),which is then cyclized by means of sulfuric acid.([*]-labeled compound).
参考文献标题:Study in vivo of MY-5116.Absorption,distribution and elimination in rats
文献作者:Esumi,A.; Jin,Y.; Uohama,K.
参考来源:Clin Rep 1985,20(2),391
产品链接: CAS No. 73080-51-0››