【药物名称】Iodixanol, DU-6807, 2-5410-3A, OptiPrep, Visipaque, Acupaque
化学结构式(Chemical Structure):
参考文献No.2446
标题:X-ray contrast agents
作者:Wille, K.; Hansen, P.-E.; Holtermann, H. (Amersham plc)
来源:EP 0108638; US 5349085
合成路线图解说明:

The title compound is prepared by condensation of the acetamido isophthalamide (I) with epichlorohydrin (II) in 2-methoxyethanol.

参考文献No.58599
标题:An N-alkylation
作者:Priebe, H. (Amersham plc)
来源:GB 2331098
合成路线图解说明:

In an improved method, the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II). Subsequent alkylation of (II) with 1-chloro-3-methoxy-2-propanol (III) yields regioselectively the N-alkylated acetamide (IV). The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线图解说明:

In a different strategy, the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II). Subsequent condensation of (II) with epichlorohydrin (III) yields the dimeric adduct (IV). The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线图解说明:

In an improved method, the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II). Subsequent alkylation of (II) with 2-chloroethanol (III) yields regioselectively the N-alkylated acetamide (IV). The borate groups of (IV) are finally removed upon quenching with diluted HCl.

参考文献No.58601
标题:Process for the production of iodinated organic X-ray contrast agents
作者:Cockbain, J.; Malthe-Soerenssen, D.; Schelver Hyni, A.C.; Aabye, A.; Bjoersvik, H.R.; Brekke, G.; Sjoegren, C.E. (Amersham plc)
来源:WO 9823296
合成路线图解说明:

The title compound is prepared by condensation of the acetamido isophthalamide (I) with epichlorohydrin (II) in 2-methoxyethanol.

参考文献No.58602
标题:Preparation of iodixanol
作者:Skailes, H.J.; Homestad, O.M. (Amersham plc)
来源:WO 0047549
合成路线图解说明:

The title compound is prepared by condensation of the acetamido isophthalamide (I) with epichlorohydrin (II) in 2-methoxyethanol.

参考文献No.671940
标题:N-acylation reactions performed in aqueous reaction medium: Screening and optimising of a synthetic step of a process for iodixanol
作者:Bjoersvik, H.-R.; et al.
来源:Org Process Res Dev 2002,6(2),113
合成路线图解说明:

In an alternative method, the tetra-acid chloride (I) derived from O-acetyl-iodixanol is condensed with 3-amino-1,2-propanediol (II) under Schotten-Baumann conditions to afford amide (III). The acetate ester group of (III) is then removed by acidic hydrolysis to furnish the title compound.

参考文献No.707300
标题:A selective process for N-alkylation in competition with O-alkylation: Boric acid, borax, and metaborate as a cheap and effective protecting group applicable for industrial-scale synthetic processes
作者:Bjoersvik, H.-R.; et al.
来源:Org Process Res Dev 2001,5(5),472
合成路线图解说明:

In an improved method, the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II). Subsequent alkylation of (II) with 1-chloro-3-methoxy-2-propanol (III) yields regioselectively the N-alkylated acetamide (IV). The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线图解说明:

In a different strategy, the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II). Subsequent condensation of (II) with epichlorohydrin (III) yields the dimeric adduct (IV). The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线图解说明:

In an improved method, the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II). Subsequent alkylation of (II) with 2-chloroethanol (III) yields regioselectively the N-alkylated acetamide (IV). The borate groups of (IV) are finally removed upon quenching with diluted HCl.

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