【药物名称】Tamsulosin hydrochloride, Amsulosin hydrochloride, Y-617, YM-12617-1, LY-253351, YM-617, EU-617, Josir, Omix, Harnal, Flomax, Alna, Flomax MR, Omic, Omnic, Pradif
化学结构式(Chemical Structure):
参考文献No.28189
标题:Sulfamoyl-substd. phenethylamine derivs., their preparation, and pharmaceutical compsns., containing them
作者:Niigata, K.; Fujikura, T. (Yamanouchi Pharmaceutical Co., Ltd.)
来源:EP 0034432; US 4373106; US 5447958
合成路线图解说明:

The condensation of 2-methoxy-5-(2-bromopropionyl)benzenesulfonamide (I) with N-benzyl-2-(2 ethoxyphenoxy)ethylamine (II) in refluxing butanone gives the tertiary amine (III), which is reduced with sodium in ethanol to the alcohol (IV). Debenzylation of (IV) with H2 over Pd/C in methanol affords the hydroxyamine (V), which by reaction with SOCl2 in acetonitrile is converted to the corresponding chloro derivative (VI). Finally, this compound is dechlorinated by hydrogenolysis with H2 over Pd/C in methanol.

参考文献No.42008
标题:Phenylethanolamine derivatives
作者:Fujikura, T.; et al. (Yamanouchi Pharmaceutical Co., Ltd.)
来源:DE 2843016; ES 474149; ES 481549; FR 2405931; GB 2006772
合成路线图解说明:

The condensation of 2-methoxy-5-(2-bromopropionyl)benzenesulfonamide (I) with N-benzyl-2-(2 ethoxyphenoxy)ethylamine (II) in refluxing butanone gives the tertiary amine (III), which is reduced with sodium in ethanol to the alcohol (IV). Debenzylation of (IV) with H2 over Pd/C in methanol affords the hydroxyamine (V), which by reaction with SOCl2 in acetonitrile is converted to the corresponding chloro derivative (VI). Finally, this compound is dechlorinated by hydrogenolysis with H2 over Pd/C in methanol.

合成路线图解说明:

The condensation of 2-methoxyphenol (I) with ethylene oxide (II) gives 2-(2-methoxyphenoxy)ethanol (III), which is treated with SOCl2 to yield 2-(2-methoxyphenoxy)ethyl chloride (IV). The reaction of (IV) with benzylamine (A) gives N-[2-(2-methoxyphenoxy)ethyl]benzylamine (V), which is condensed with 2-methyl-5-bromoacetylbenzenesulfonamide (VI) affording N-[2-(2-methoxyphenoxy)ethyl]-N-[(4-methyl-3-aminosulfonylbenzoyl)methyl]benzylamine (VII). The reduction of (VII) with NaBH4 affords the corresponding protected carbinol (VIII), which is finally debenzylated by hydrogenation with H2 over Pd/C.

参考文献No.65154
标题:YM-12617
作者:Casta馿r, J.; Mannhold, R.
来源:Drugs Fut 1986,11(4),293
合成路线图解说明:

The condensation of 2-methoxy-5-(2-bromopropionyl)benzenesulfonamide (I) with N-benzyl-2-(2 ethoxyphenoxy)ethylamine (II) in refluxing butanone gives the tertiary amine (III), which is reduced with sodium in ethanol to the alcohol (IV). Debenzylation of (IV) with H2 over Pd/C in methanol affords the hydroxyamine (V), which by reaction with SOCl2 in acetonitrile is converted to the corresponding chloro derivative (VI). Finally, this compound is dechlorinated by hydrogenolysis with H2 over Pd/C in methanol.

参考文献No.90283
标题:The synthesis of the 14C and 2H-isotopomers of (R)-N-[2-(2'-ethoxyphenoxy)-ethyl]-N-2-[3-(4'-methoxy-3'-sulfonamido)-phenyl]-propylamine hydrochloride, an alpha1-adrenoreceptor antagonist
作者:Hunden, D.C.; Wheller, W.J.; Schmiegel, K.K.
来源:J Label Compd Radiopharm 1989,26(2),171
合成路线图解说明:

A new synthesis of YM-12617-1, the active R-isomer of YM-12617, has been described: The reductocondensation of 1-(4-methoxyphenyl)-2-propanone (I) with R-1-phenylethylamine (II) gives regioselectively the secondary amine (III) as the HCl salt, which by sulfonation with chlorosulfonic acid and treatment with NH4OH yields (R,R)-2-methoxy-5-[2-(1-phenylethylamino)propyl]benzenesulfonamide (IV). Eliminating the protecting group by hydrogenation, the free amine hydrochloride (V) is obtained, which is finally submitted to a reductocondensation with 2-(2-ethoxyphenoxy)acetaldehyde (VI) by means of sodium borohydride in methanol, and treated with HCl in ether.

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