【药物名称】Nifekalant hydrochloride, MS-551, Shinbit
化学结构式(Chemical Structure):
参考文献No.12486
标题:Pyrimidinedione deriv. cpds., method of producing the same and antiarrhythmic agents containing the same
作者:Katakami, T.; Yokoyama, T.; Miyamoto, M.; Mori, H.; Kawauchi, N.; Nobori, T.; Sannohe, K.; Kamiya, J.; Ishii, M.; Yoshihara, K. (Mitsui Chemicals, Inc.)
来源:AU 8943869; EP 0369627; JP 1991112948; JP 1991173873; US 5008267
合成路线图解说明:

By condensation of N-(2-hydroxyethyl)-N-[3-(4-nitrophenyl)propyl]amine (I) with 1,3-dimethyl-6-[2-(p-toluenesulfonyloxy)ethylamino]pyrimidine-2,4(1H,3H)-dione (II) by means of NaOH in hot ethanol or methanol. The starting materials are obtained as follows: 1) The esterification of 3-(4-nitrophenyl)propanol (III) with p-toluenesulfonyl chloride (IV) by means of pyridine in chloroform gives the corresponding p-toluenesulfonate (V), which is then condensed with ethanolamine (VI) by heating at 100 C to afford amine (I). 2) The condensation of ethanolamine (VI) with 6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VII) by heating at 90 C, or by means of triethylamine in refluxing isopropanol, gives 6-(2-hydroxyethylamino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VIII), which is then esterified with p-toluenesulfonyl chloride (IV) as before yielding pyrimidine (II).

参考文献No.200898
标题:MS-551
作者:Casta馿r, J.; Prous, J.
来源:Drugs Fut 1993,18(3),226
合成路线图解说明:

By condensation of N-(2-hydroxyethyl)-N-[3-(4-nitrophenyl)propyl]amine (I) with 1,3-dimethyl-6-[2-(p-toluenesulfonyloxy)ethylamino]pyrimidine-2,4(1H,3H)-dione (II) by means of NaOH in hot ethanol or methanol. The starting materials are obtained as follows: 1) The esterification of 3-(4-nitrophenyl)propanol (III) with p-toluenesulfonyl chloride (IV) by means of pyridine in chloroform gives the corresponding p-toluenesulfonate (V), which is then condensed with ethanolamine (VI) by heating at 100 C to afford amine (I). 2) The condensation of ethanolamine (VI) with 6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VII) by heating at 90 C, or by means of triethylamine in refluxing isopropanol, gives 6-(2-hydroxyethylamino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VIII), which is then esterified with p-toluenesulfonyl chloride (IV) as before yielding pyrimidine (II).

参考文献No.203387
标题:Synthesis and pharmacological studies of N-substituted 6-[(2-aminoethyl)amino]-1,3-dimethyl-2,4(1H,3H) pyrimidinediones, novel class III antiarrhythmic agents
作者:Katakami, T.; Yokoyama, T.; Miyamoto, M.; Mori, H.; Kawauchi, N.; Nobori, T.; San-nohe, K.; Kaiho, T.; Kamiya, J.
来源:J Med Chem 1992,35(18),3325-30
合成路线图解说明:

By condensation of N-(2-hydroxyethyl)-N-[3-(4-nitrophenyl)propyl]amine (I) with 1,3-dimethyl-6-[2-(p-toluenesulfonyloxy)ethylamino]pyrimidine-2,4(1H,3H)-dione (II) by means of NaOH in hot ethanol or methanol. The starting materials are obtained as follows: 1) The esterification of 3-(4-nitrophenyl)propanol (III) with p-toluenesulfonyl chloride (IV) by means of pyridine in chloroform gives the corresponding p-toluenesulfonate (V), which is then condensed with ethanolamine (VI) by heating at 100 C to afford amine (I). 2) The condensation of ethanolamine (VI) with 6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VII) by heating at 90 C, or by means of triethylamine in refluxing isopropanol, gives 6-(2-hydroxyethylamino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (VIII), which is then esterified with p-toluenesulfonyl chloride (IV) as before yielding pyrimidine (II).

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