【药物名称】SM-18163
化学结构式(Chemical Structure):
参考文献No.34703
标题:Piperidinylpyramidine derivs.
作者:Fujiwara, N.; Ueda, Y.; Murata, S.; Hirota, F.; Kawakami, H.; Fujita, H. (Sumitomo Pharmaceuticals Co., Ltd.)
来源:EP 0892795; JP 2001511764; US 5948786; WO 9738992
合成路线图解说明:

N-Benzoylisonipecotic acid (I) was chlorinated with SOCl2 to produce the corresponding acid chloride (II). Acylation of the lithium enolate of (4-methoxyphenyl)acetone (III) with acid chloride (II) provided a mixture of diketone regioisomers (IV) and (V); these were separated by column chromatography. The desired diketone (IV) was then cyclized with guanidine (VI) in hot pyridine to afford the pyrimidine (VII). Basic hydrolysis of the benzamide function of (VII) gave the piperidine derivative (VIII). The target amide was finally prepared by acylation of (VIII) with 3,4-methylenedioxybenzoic acid (IX) in the presence of EDC.

参考文献No.642732
标题:Synthesis and bioactivities of novel piperidylpyrimidine derivatives: Inhibitors of tumor necrosis factor-alpha production
作者:Fujiwara, N.; Fujita, H.; Iwai, K.; Kurimoto, A.; Murata, S.; Kawakami, H.
来源:Bioorg Med Chem Lett 2000,10(12),1317
合成路线图解说明:

N-Benzoylisonipecotic acid (I) was chlorinated with SOCl2 to produce the corresponding acid chloride (II). Acylation of the lithium enolate of (4-methoxyphenyl)acetone (III) with acid chloride (II) provided a mixture of diketone regioisomers (IV) and (V); these were separated by column chromatography. The desired diketone (IV) was then cyclized with guanidine (VI) in hot pyridine to afford the pyrimidine (VII). Basic hydrolysis of the benzamide function of (VII) gave the piperidine derivative (VIII). The target amide was finally prepared by acylation of (VIII) with 3,4-methylenedioxybenzoic acid (IX) in the presence of EDC.

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