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    Threo-adrenalinecarboxylic acid, processes for the production thereof, and pharmaceutical compositions thereof
    5.
    发明公开
    Threo-adrenalinecarboxylic acid, processes for the production thereof, and pharmaceutical compositions thereof 失效
    苏 - 肾上腺素羧酸，其制备方法和含有它们的药物组合物。

    公开(公告)号：EP0112606A1

    公开(公告)日：1984-07-04

    申请号：EP83304804.4

    申请日：1983-08-19

    申请人： ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

    发明人： Umezawa, Hamo ,  Nagatsu, Toshiharu ,  Narabayashi, Hirotaro ,  Takeuchi, Tomio ,  Iwadare, Shuichi ,  Matsumoto, Ikuo ,  Yoshizawa, Junji ,  Morishima, Hajime ,  Tomimoto, Koji

    IPC分类号： C07C101/72 ,  C07C125/063 ,  C07B57/00

    CPC分类号： C07C229/36 ,  Y02P20/55

    摘要： DL- and L-Threo-3-(3,4-dihydroxyphenyl)-N-methyl-serine which may also be termed as DL- and L-threo-adrenalinecarboxylic acid are now provided, which are new compounds useful for therapeutic treatment of Parkinson's disease and mental depression disease. DL-Adrenalinecarboxylic acid may be produced by a new process comprising reacting glycine with O-protected 3,4-dihydroxybenzaldehyde, hydrolyzing the resultant reaction product under acidic conditions to form O-protected DL-3-(3,4-dihydroxyphenyl)serine, isolating the O-protected DL-3-(3,4-dihydroxyphenyl)serine into the threo isomer and the erythro isomer by recrystallization from a suitable organic solvent, introducing an unsubstituted or substituted benzyl group into the 2-amino group of the resulting O-protected DL-threo-3-(3,4-dihydroxyphenyl)serine, then N-methylating the resulting O-protected DL-threo-3-(3,4-dihydroxyphenyl)-N-benzylserine,and removing the O-protecting groups as well as the unsubstituted or substituted benzyl group at the 2-methylamino group of the N-methylation product.
    L-threo-Adrenalinecarboxylic acid may be produced by a new process comprising introducing a p-methoxybenzyloxycarbonyl group into the 2-amino group of the O-protected DL-threo-3-(3,4-dihydroxyphenyl)serine obtained as an intermediate product, optically resolving the resultant 0-protected DL-threo-3-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl-serine by reacting the latter with an optically active amine and recrystallizing the resultant amine salt products from a suitable organic solvent, removing the p-methoxybenzyloxycarbonyl group from the resultant O-protected L-threo-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl-serine, reacting the resultant O-protected L-threo-(3,4-dihydroxyphenyl)serine with dimethyl sulfate in dry acetone to form an O-protected L-threo-(3,4-dihydroxyphenyl)-N-methylserine methyl ester, saponifying this methyl ester and then removing the O-protecting groups from the saponification product.

    摘要翻译： DL和L-苏-3-（3,4-二羟基苯基）-N-甲基 - 丝氨酸因此可称为为DL和L-苏adrenalinecarboxylic酸现在提供，这对于治疗性治疗是有用的新化合物 帕金森氏症和精神抑郁症。 DL Adrenalinecarboxylic酸可以由一个新的流程，包括使用O-保护3,4-二羟基苯甲醛甘氨酸，水解在酸性条件下将所得的反应产物以形成O-保护DL-3丝氨酸产生（3,4-二羟基苯基） 分离O-保护DL-3-（3,4-二羟基苯基）丝氨酸到苏 - 异构体和从合适的有机溶剂重结晶法的赤式异构体，引入到unsubstituiertem或substituiertem苄基引入生成的O的2-氨基 - 保护的DL-苏 - （3,4-二羟基苯基）丝氨酸，然后加入N-甲基化得到的O-保护的DL-苏-3-（3,4-二羟基苯基）-N- benzylserine，除去O型保护基团如 以及在2-甲基氨基的N-甲基化产物的unsubstituiertem或substituiertem苄基。 ... L-苏Adrenalinecarboxylic酸可以由一个新的流程corncrising intronucing一对甲氧基基团引入到O-保护DL-苏-3-（3,4-二羟基苯基）丝氨酸的2-氨基来制备 得到的中间产物，旋光拆分得到的O-保护的DL-苏-3-（3,4- dihyroxyphenyl）由后者-N-对甲氧基苄丝氨酸与光学活性的胺反应，并从再结晶得到的胺盐产品 合适的有机溶剂，除去O型保护的L-苏 - （3,4-二羟基苯基）的对甲氧基组结式-N-对甲氧基苄丝氨酸，O-起反应所得到的保护的L-苏式 - （3,4-二羟 ）丝氨酸与硫酸二甲酯在无水丙酮以形成（3,4-二羟基苯基）-N-甲基丝氨酸甲酯，皂化该甲基酯，然后从O-保护的L-苏式的皂化产物中除去O-保护基团。