Iofratol, B-19470

碘拉醇Chemical Name: N,N''-(2-Hydroxypropane-1,3-diyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[2(S)-hydroxypropionamido]-2,4,6-triiodo-1,3-benzenedicarboxamide]; N,N''-(2-Hydroxytrimethylene)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-5-[(S)-lactamido]isophthalamide]
CAS No. 141660-63-1
项目整合开发状态: Preclinical
项目研究机构: Bracco (Originator)
合成路线:The synthetic pathway is shown in Scheme 19316401a:Treatment of (S)-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarbonyldichloride (I) with 2-amino-1,3-propanediol in diglyme yields (S)-3-[(2-acetyloxy-1-oxopropyl)amino]-5-[[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl]-2,4,6-triiodobenzenecarbonylchloride (II).Compound (II) is treated with 1,3-diamino-2-propanol to give the dimeric compound [(S)-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide] (III).Hydrolysis of compound (III) and desalting of its aqueous solution gives a crude [S-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide,which is subsequently purified through a bed of adsorbent resin.
📌 参考资料/链接:
参考文献标题:1,3-Bis[3-(mono- or poly-hydroxy)acylamino-5-(mono- or poly-hydroxyalkyl)aminocarbonyl-2,4,6-triiodo-benzoyl-amino]-hydroxy-or hydroxyalkyl-propanes,their methods of preparation and X-ray contrast media containing them
文献作者:Uggeri,F.; Brocchetta,M.(Bracco SpA)
参考来源:EP 0557345; JP 1994504268; WO 9208691

📄 详细内容


合成路线:The synthetic pathway is shown in Scheme 19316401a:Treatment of (S)-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarbonyldichloride (I) with 2-amino-1,3-propanediol in diglyme yields (S)-3-[(2-acetyloxy-1-oxopropyl)amino]-5-[[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl]-2,4,6-triiodobenzenecarbonylchloride (II).Compound (II) is treated with 1,3-diamino-2-propanol to give the dimeric compound [(S)-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide] (III).Hydrolysis of compound (III) and desalting of its aqueous solution gives a crude [S-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide,which is subsequently purified through a bed of adsorbent resin.

参考文献标题:Iofratol
文献作者:Luzzani,F.L.; Ha雗,C.
参考来源:Drugs Fut 1995,20(11),1120


合成路线:The synthetic pathway is shown in Scheme 19316401a:Treatment of (S)-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarbonyldichloride (I) with 2-amino-1,3-propanediol in diglyme yields (S)-3-[(2-acetyloxy-1-oxopropyl)amino]-5-[[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl]-2,4,6-triiodobenzenecarbonylchloride (II).Compound (II) is treated with 1,3-diamino-2-propanol to give the dimeric compound [(S)-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide] (III).Hydrolysis of compound (III) and desalting of its aqueous solution gives a crude [S-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide,which is subsequently purified through a bed of adsorbent resin.

参考文献标题:Contrast media research.An investment for the future
文献作者:Renaa,T.; Jakobsen,T.
参考来源:Acta Radiol 1987,Suppl.3709-11


合成路线:The synthetic pathway is shown in Scheme 19316401a:Treatment of (S)-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarbonyldichloride (I) with 2-amino-1,3-propanediol in diglyme yields (S)-3-[(2-acetyloxy-1-oxopropyl)amino]-5-[[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl]-2,4,6-triiodobenzenecarbonylchloride (II).Compound (II) is treated with 1,3-diamino-2-propanol to give the dimeric compound [(S)-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide] (III).Hydrolysis of compound (III) and desalting of its aqueous solution gives a crude [S-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide,which is subsequently purified through a bed of adsorbent resin.
参考文献标题:Physicochemical parameters of X-ray contrast media
文献作者:Heimann,G.; Kollenkirchen,U.; Miklautz,H.; Krause,W.
参考来源:Invest Radiol 1994,2972-80


产品链接: CAS No. 141660-63-1››