C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/515.4, 260/5
C07C 51/347 (2006.01) A61K 31/16 (2006.01) A61K 31/195 (2006.01) C07C 233/31 (2006.01) C07C 233/47 (2006.01) C07C 233/76 (2006.01) C07C 233/87 (2006.01) C07C 271/22 (2006.01) C07C 271/34 (2006.01) C07C 271/54 (2006.01) C07D 209/48 (2006.01) C07K 1/06 (2006.01) C07K 5/02 (2006.01) C07K 5/06 (2006.01) A47L 13/40 (2006.01)
Patent
CA 1182125
ABSTRACT: A process for producing threo-3-amino-2-hydroxybutanoyl- aminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: Image (I), wherein R1 represents a naphthyl or a group of the formula: Image in which R6 and R7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy, a lower alkyl or phenyl and R2 represents a protected amino, with a starting compound represented by the general formula: Image (II), wherein R3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: Image (III), wherein R1, R2 and R3 have the same meanings as above, and then reducing the same into threo-3-protected arnino-2-hydroxybutanoic acid or its ester represented by the general formula: Image (IV), wherein R1, R2 and R3 have the same meanings as above, and further converting the above compound into threo -3-amino-2- hydroxybutanoic acid represented by the general formula; Image (V), wherein R? represents amino or a protected amino, thereafter condensing the same, in a conventional manner for forming a peptide bond, with a compound represented by the general formula: Image (VI), wherein R4 represents all alkyl having 3 - 4 carbon atom or 3-guanidinopropyl, while previously protecting as required those groups not relevant to the reaction, and removing the protecting groups for the functional groups to produce threo-3-amino-2- hydroxybutanoylaminoacetic acids represented by the general formula: Image (VII), wherein R1 and R4 have the same meanings as above. This inven- tion also provides the compounds represented by the general formula (III) as novel intermediates for the above aimed compounds and a process for producing the intermediates.
340428
Aoyagi Takaaki
Nishizawa Rinzo
Saino Tetsushi
Shirai Tadashi
Suzuki Masao
Borden Ladner Gervais Llp
Nippon Kayaku Kabushiki Kaisha
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