【药物名称】Seratrodast, ABT-001, A-73001, Abbott-73001, AA-2414, Bronica
化学结构式(Chemical Structure):
参考文献No.3880
标题:Quinone derivs., their production and use
作者:Terao, S.; Maki, Y. (Takeda Chemical Industries, Ltd.)
来源:AU 8545615; EP 0171251; ES 8704870; JP 1986044840; JP 1991072444; JP 1991081248; JP 1991086841; US 5180742; WO 8600887; WO 8604058
合成路线图解说明:

The reaction of pimelic acid monoester (I) with refluxing SOCl2 gives the corresponding acid chloride (II), which by a Friedel-Craft's condensation with benzene (AlCl3 as catalyst) is converted into 6-benzoylhexanoic acid ethyl ester (III). The reduction of (III) with NaBH4 in methanol affords 7-hydroxy-7-phenylheptanoic acid ethyl ester (IV), which is hydrolyzed with NaOH in hot THF - water to yield the corresponding free acid (V). Finally, this compound is condensed with trimethylhydroquinone (VI) by means of boron trifluoride ethearate in hot toluene.

参考文献No.6663
标题:Quinone amides, their production and use
作者:Terao, S.; Maki, Y. (Takeda Chemical Industries, Ltd.)
来源:EP 0232089; JP 1987246545
合成路线图解说明:

The reaction of pimelic acid monoester (I) with refluxing SOCl2 gives the corresponding acid chloride (II), which by a Friedel-Craft's condensation with benzene (AlCl3 as catalyst) is converted into 6-benzoylhexanoic acid ethyl ester (III). The reduction of (III) with NaBH4 in methanol affords 7-hydroxy-7-phenylheptanoic acid ethyl ester (IV), which is hydrolyzed with NaOH in hot THF - water to yield the corresponding free acid (V). Finally, this compound is condensed with trimethylhydroquinone (VI) by means of boron trifluoride ethearate in hot toluene.

参考文献No.98400
标题:Quinones. 4. Novel eicosanoid antagonists: Synthesis and pharmacological evaluation
作者:Shiraishi, M.; Kato, K.; Terao, S.; Ashida, Y.; Terashita, Z.-I.; Kito, G.
来源:J Med Chem 1989,32(9),2214-21
合成路线图解说明:

The reaction of pimelic acid monoester (I) with refluxing SOCl2 gives the corresponding acid chloride (II), which by a Friedel-Craft's condensation with benzene (AlCl3 as catalyst) is converted into 6-benzoylhexanoic acid ethyl ester (III). The reduction of (III) with NaBH4 in methanol affords 7-hydroxy-7-phenylheptanoic acid ethyl ester (IV), which is hydrolyzed with NaOH in hot THF - water to yield the corresponding free acid (V). Finally, this compound is condensed with trimethylhydroquinone (VI) by means of boron trifluoride ethearate in hot toluene.

参考文献No.118992
标题:AA-2414
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1990,15(8),783
合成路线图解说明:

The reaction of pimelic acid monoester (I) with refluxing SOCl2 gives the corresponding acid chloride (II), which by a Friedel-Craft's condensation with benzene (AlCl3 as catalyst) is converted into 6-benzoylhexanoic acid ethyl ester (III). The reduction of (III) with NaBH4 in methanol affords 7-hydroxy-7-phenylheptanoic acid ethyl ester (IV), which is hydrolyzed with NaOH in hot THF - water to yield the corresponding free acid (V). Finally, this compound is condensed with trimethylhydroquinone (VI) by means of boron trifluoride ethearate in hot toluene.

参考文献No.124058
标题:Quinone derivatives: Synthesis and structure-activity relations of a novel class of eicosanoid antagonists, AA-2414 and its analogs
作者:Terao, S.
来源:Advances in Prostaglandin, Thromboxane and Leukotriene Research 1989,19651-654
合成路线图解说明:

The reaction of pimelic acid monoester (I) with refluxing SOCl2 gives the corresponding acid chloride (II), which by a Friedel-Craft's condensation with benzene (AlCl3 as catalyst) is converted into 6-benzoylhexanoic acid ethyl ester (III). The reduction of (III) with NaBH4 in methanol affords 7-hydroxy-7-phenylheptanoic acid ethyl ester (IV), which is hydrolyzed with NaOH in hot THF - water to yield the corresponding free acid (V). Finally, this compound is condensed with trimethylhydroquinone (VI) by means of boron trifluoride ethearate in hot toluene.

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