【药物名称】FPL-66564
化学结构式(Chemical Structure):
参考文献No.16786
标题:Angiotensin converting enzyme inhibitors
作者:Baxter, A.J.G.; Meghani, P. (Celltech Medeva plc)
来源:EP 0535496; JP 1993507919; US 5348978; WO 9200276
合成路线图解说明:

D-Serine (I) is nitrosated in the presence of bromide ion to give (R)-2-bromo-3-hydroxypropanoic acid (II), which is converted into (R)-2-hydroxy-3-(methylthio)propanoic acid (IV), via the epoxy acid (III), using sodium methoxide followed by sodium methanethiolate. This hydroxy acid (IV) is coupled to (S)-3-(acetylthio)-2-methylpropanoic acid using either the imidazolide or acid chloride. Final deprotection of 2(R)-[3-(acetylthio)-2(S)-methyl-1-oxopropoxy]-3-(methylthio)propanoic acid (V) is achieved using aqueous ammonia. FPL 66564 is conveniently isolated either as the 1-adamantanamine or L-lysine salt.

参考文献No.185819
标题:FPL 66564, the first ultra short-acting angiotensin converting enzyme inhibitor (USACEI)
作者:Baxter, A.J.G.; Hallam, C.; Harper, S.T.; Meghani, P.
来源:J Hypertension 1992,10(Suppl. 4),S147
合成路线图解说明:

D-Serine (I) is nitrosated in the presence of bromide ion to give (R)-2-bromo-3-hydroxypropanoic acid (II), which is converted into (R)-2-hydroxy-3-(methylthio)propanoic acid (IV), via the epoxy acid (III), using sodium methoxide followed by sodium methanethiolate. This hydroxy acid (IV) is coupled to (S)-3-(acetylthio)-2-methylpropanoic acid using either the imidazolide or acid chloride. Final deprotection of 2(R)-[3-(acetylthio)-2(S)-methyl-1-oxopropoxy]-3-(methylthio)propanoic acid (V) is achieved using aqueous ammonia. FPL 66564 is conveniently isolated either as the 1-adamantanamine or L-lysine salt.

参考文献No.193896
标题:FPL 66564
作者:Carr, R.D.; Baxter, A.J.G.
来源:Drugs Fut 1993,18(1),12
合成路线图解说明:

D-Serine (I) is nitrosated in the presence of bromide ion to give (R)-2-bromo-3-hydroxypropanoic acid (II), which is converted into (R)-2-hydroxy-3-(methylthio)propanoic acid (IV), via the epoxy acid (III), using sodium methoxide followed by sodium methanethiolate. This hydroxy acid (IV) is coupled to (S)-3-(acetylthio)-2-methylpropanoic acid using either the imidazolide or acid chloride. Final deprotection of 2(R)-[3-(acetylthio)-2(S)-methyl-1-oxopropoxy]-3-(methylthio)propanoic acid (V) is achieved using aqueous ammonia. FPL 66564 is conveniently isolated either as the 1-adamantanamine or L-lysine salt.

参考文献No.194881
标题:(R)-2-(3-Mercapto-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acid (FPL 66564), the first ultra short-acting angiotensin converting enzyme inhibitor (USACEI)
作者:Baxter, A.J.G.; Carr, R.D.; Eyley, S.C.; Fraser-Rae, L.; Hallam, C.; Harper, S.T.; Hurved, P.A.; King, S.J.; Meghani, P.
来源:J Med Chem 1992,353718-20
合成路线图解说明:

D-Serine (I) is nitrosated in the presence of bromide ion to give (R)-2-bromo-3-hydroxypropanoic acid (II), which is converted into (R)-2-hydroxy-3-(methylthio)propanoic acid (IV), via the epoxy acid (III), using sodium methoxide followed by sodium methanethiolate. This hydroxy acid (IV) is coupled to (S)-3-(acetylthio)-2-methylpropanoic acid using either the imidazolide or acid chloride. Final deprotection of 2(R)-[3-(acetylthio)-2(S)-methyl-1-oxopropoxy]-3-(methylthio)propanoic acid (V) is achieved using aqueous ammonia. FPL 66564 is conveniently isolated either as the 1-adamantanamine or L-lysine salt.

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