C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
530/9
C07H 15/00 (2006.01) C07K 9/00 (2006.01)
Patent
CA 1185236
IMMUNOLOGICALLY ACTIVE DIPEPTIDYL SACCHARIDES AND METHODS OF PREPARATION ABSTRACT OF THE DISCLOSURE 2-Amino-2-deoxy-glycoses of the general structural formula: Image I II III wherein R1 is hydrogen, alkyl (1-7C), substituted alkyl (1-7C), phenyl, substituted phenyl, benzyl, or substituted benzyl; R2 is alkyl, substituted alkyl, phenyl, or substituted phenyl; R3 is H or lower alkyl (1-10C) with the proviso that when the aminoglycose has the 2-amino-2-deoxy-?- glucose configuration, R3 cannot be H; R4 and R5 are same or different and are H, aliphatic or aromatic acyl (2-21C) or substituted acyl (2-21C); R6 is H, or R6-R7 together is -CH2-CH2-CH2-, R7 is H, alkyl (1-7C), hydroxymethyl, mercaptomethyl, benzyl, or substituted benzyl; R8 and R9 each is carboxyl, esterified carboxyl (1-7C), amidated carboxyl, or mono- or di-alkyl-(1-3C)- amidated carboxyl; Provided that when R3 is lower alkyl, the stereochemistry at asymmetric center I can be either ? or ?, but that when the aminoglycose has the 2-amino-2-deoxy-D-glucose configuration, the stereochemistry at I cannot be ?; When R7 is not H, the stereochemistry at asymmetric center II is either ? or ?; and The stereochemistry at asymmetric center III is ?. These compounds possess immunostimulatory properties.
343787
Durette Philippe L.
Shen Tsung-Ying
Goudreau Gage Dubuc
Merck & Co. Inc.
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