【药物名称】Pariprazole sodium, Rabeprazole sodium, LY-307640, E-3810, Aciphex, Pariet
化学结构式(Chemical Structure):
参考文献No.8300
标题:Pyridine derivs., pharmaceutical compsns. comprising the same, the use of the same for the manufacture of medicaments having therapeutic or preventative value, and a process for preparing the same
作者:Souda, S.; Ueda, N.; Miyazawa, S.; Tagami, K.; Nomoto, S.; Okita, M.; Shimomura, N.; Kaneko, T.; Fujimoto, M.; Murakami, M.; Oketani, K.; Fujisaki, H.; Shibata, H.; Wakabayashi, T. (Eisai Co., Ltd.)
来源:AU 8781138; EP 0268956; EP 0475456; EP 0654471; EP 0786461; JP 1989006270; JP 1993247035; JP 1995291967; US 5045552; US 5998445
合成路线图解说明:

The condensation of 4-chloro-2,3-dimethylpyridine N-oxide (I) with 3-methoxypropanol (II) by means of NaH in DMSO gives 4-(3-methoxypropoxy)-2,3-dimethylpyridine N-oxide (III), which is treated with acetic anhydride at 90 C yielding 2-(acetoxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (IV). The hydrolysis of (IV) with NaOH in ethanol affords 2-(hydroxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V), which by treatment with SOCl2 in dichloromethane is converted into 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (VI). The condensation of (VI) with 2-mercaptobenzimidazole (VII) by means of NaOH in ethanol gives 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethylthio]benzimidazole (VIII), which is oxidized with m-chloroperbenzoic acid in ether - dichloromethane to afford 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylsulfinyl]benzimidazole (IX). Finally, this compound is treated wtih aqueous Na2CO3.

参考文献No.129135
标题:E-3810
作者:Casta馿r, J.; Prous, J.
来源:Drugs Fut 1991,16(1),19
合成路线图解说明:

The condensation of 4-chloro-2,3-dimethylpyridine N-oxide (I) with 3-methoxypropanol (II) by means of NaH in DMSO gives 4-(3-methoxypropoxy)-2,3-dimethylpyridine N-oxide (III), which is treated with acetic anhydride at 90 C yielding 2-(acetoxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (IV). The hydrolysis of (IV) with NaOH in ethanol affords 2-(hydroxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V), which by treatment with SOCl2 in dichloromethane is converted into 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (VI). The condensation of (VI) with 2-mercaptobenzimidazole (VII) by means of NaOH in ethanol gives 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethylthio]benzimidazole (VIII), which is oxidized with m-chloroperbenzoic acid in ether - dichloromethane to afford 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylsulfinyl]benzimidazole (IX). Finally, this compound is treated wtih aqueous Na2CO3.

参考文献No.228735
标题:Synthesis of 14C-labelled sodium pariprazole (E3810)
作者:Sohda, S.; Tagami, K.; Chiku, S.
来源:J Label Compd Radiopharm 1993,33(9),849
合成路线图解说明:

A synthesis for [14C]-labeled E-3810 has been described: The cyclization of o-phenylenediamine (I) with [14C]-labeled carbon disulfide (II) by means of aqueous KOH gives the potassium salt of [14C]-2-mercaptobenzimidazole (III), which is treated with acetic acid to obtain the corresponding thiol (IV). The condensation of (IV) with 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V) by means of NaOH in refluxing ethanol yields [14C]-labeled 2-[4-(3-methoxypropoxy)-3-methylpyridin-3-ylmethylthio]benzimidazole (VI). The oxidation of (VI) with m-chloroperbenzoic acid in dichloromethane affords the corresponding sulfoxide (VIII), which is finally treated with 0.1 N NaOH in ethanol.

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