【药物名称】AD-5467
化学结构式(Chemical Structure):
参考文献No.7223
标题:Thiolactam-N-acetic acid derivs., their production and use
作者:Meguro, K.; Ikeda, H.; Yamamoto, Y. (Senju Pharmaceuticals Co., Ltd.; Takeda Chemical Industries, Ltd.)
来源:EP 0243018; JP 1988107970; US 4771050
合成路线图解说明:

The cyclization of 2-amino-6-isoproylphenol (I) with 2-bromo-3-methylbutyryl chloride (II) by means of NaHCO3 in ethyl acetate - water gives 2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one (III), which is condensed with methyl bromoacetate (IV) by means of NaH in DMF yielding 2,8-diisopropyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-4-acetic acid methyl ester (V). The reaction of (V) with P2S5 in refluxing toluene affords the corresponding thioxo derivative (VI), which is finally hydrolyzed with NaOH in dioxane - methanol.

参考文献No.120742
标题:Studies on antidiabetic agents. IX. A new aldose reductase inhibitor, AD-5467, and related 1,4-benzoxazine and 1,4-benzothiazine derivatives: Synthesis and biological activity
作者:Ikeda, H.; Meguro, K.; Yamamoto, Y.; Tawada, Sugiyama, Y.
来源:Chem Pharm Bull 1990,38(5),1238-45
合成路线图解说明:

The cyclization of 2-amino-6-isoproylphenol (I) with 2-bromo-3-methylbutyryl chloride (II) by means of NaHCO3 in ethyl acetate - water gives 2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one (III), which is condensed with methyl bromoacetate (IV) by means of NaH in DMF yielding 2,8-diisopropyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-4-acetic acid methyl ester (V). The reaction of (V) with P2S5 in refluxing toluene affords the corresponding thioxo derivative (VI), which is finally hydrolyzed with NaOH in dioxane - methanol.

参考文献No.129430
标题:AD-5467
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1991,16(1),13
合成路线图解说明:

The cyclization of 2-amino-6-isoproylphenol (I) with 2-bromo-3-methylbutyryl chloride (II) by means of NaHCO3 in ethyl acetate - water gives 2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one (III), which is condensed with methyl bromoacetate (IV) by means of NaH in DMF yielding 2,8-diisopropyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-4-acetic acid methyl ester (V). The reaction of (V) with P2S5 in refluxing toluene affords the corresponding thioxo derivative (VI), which is finally hydrolyzed with NaOH in dioxane - methanol.

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