【药物名称】Amfenac sodium, AHR-5850D, Fenazox, Fenamate
化学结构式(Chemical Structure):
参考文献No.830
标题:Anti-inflammatory methods using 2-amino-3-(5- and 6-)benzoylphenyl acetic acids, esters and metal salts thereof and the compounds
作者:Welstead, W.J.Jr.; Moran, H.W. (A.H. Robins Co. Inc.)
来源:CA 1012979; DE 2324768; FR 2184934; GB 1521097; US 4045576
合成路线图解说明:

The reaction of 1-aminoindolin-2-one (I) with phenylacetone (A) by means of acetic acid in refluxing ethanol gives 1-(alpha-methylphenethylidiene-imino)indolin-2-one (II), which by reaction with refluxing ethanolic hydrogen chloride affords ethyl alpha-(2-methyl-3-phenylindol-7-yl)acetate (III). The ozonolysis of (III) in acetic acid yields ethyl 2-acetamido-3-benzoylphenyl-acetate (IV), which is cyclized by refluxing with HCl in acetic acid to give 7-benzoylindolin-2-one (V). Finally, of the ester (III) with KOH in refluxing water affords the corresponding acid (this compound is hydrolyzed with NaOH in refluxing water). The hydrolysis of the ester (III) with KOH in refluxing water affords the corresponding acid (VI), which can be ozonolyzed as before yielding 2-acetamido-3-benzoylphenylacetic acid (VII). This acid can be cyclized to (V) by refluxing with HCl in acetic acid as before.

参考文献No.49336
标题:Amfenac
作者:Hillier, K.; Casta馿r, J.
来源:Drugs Fut 1978,3(5),340
合成路线图解说明:

The reaction of 1-aminoindolin-2-one (I) with phenylacetone (A) by means of acetic acid in refluxing ethanol gives 1-(alpha-methylphenethylidiene-imino)indolin-2-one (II), which by reaction with refluxing ethanolic hydrogen chloride affords ethyl alpha-(2-methyl-3-phenylindol-7-yl)acetate (III). The ozonolysis of (III) in acetic acid yields ethyl 2-acetamido-3-benzoylphenyl-acetate (IV), which is cyclized by refluxing with HCl in acetic acid to give 7-benzoylindolin-2-one (V). Finally, of the ester (III) with KOH in refluxing water affords the corresponding acid (this compound is hydrolyzed with NaOH in refluxing water). The hydrolysis of the ester (III) with KOH in refluxing water affords the corresponding acid (VI), which can be ozonolyzed as before yielding 2-acetamido-3-benzoylphenylacetic acid (VII). This acid can be cyclized to (V) by refluxing with HCl in acetic acid as before.

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