Modified kojibiosides analogues
AssigneeAlberta Research Council
InventorsOm Srivastava, Roman Szweda, Ulrike Spohr
Life of this patent
Estimating the term…
Abstract
Disclosed are novel analogues of kojibiose and pharmaceutical compositions comprising such analogues.
Claims26
A compound useful as an .alpha.-glucosidase I inhibitor or as an intermediate in the production of .alpha.-glucosidase I inhibitor selected from the group consisting of compounds represented by formulas I-IV, VII and VIII ##STR12## wherein each Y is independently --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.1 is selected from the group consisting of --O-acetyl, --OH, --O-mesityl, --N.sub.3, --Cl, --F, --I, --H, --O-methyl, --OSi(CH.sub.3).sub.2 -tert-butyl and --O-benzyl;
- and R.sup.2 is selected from the group consisting of --O-acetyl, --OH, --O-methyl, --OC(S)O-phenyl, --H and --O-benzyl;
- ##STR13## wherein each Y is independently --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.3 is selected from the group consisting of --OH, --O-mesityl, --N.sub.3, --Cl, --I, --H, --OSi(CH.sub.3).sub.2 -tert-butyl;
- and R.sup.4 is selected from the group consisting of --OH, --H and --OC(S)0-phenyl;
- ##STR14## wherein each Y is independently --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.5 is selected from the group consisting of --OSi(CH.sub.3).sub.2 tert-butyl, --N.sub.3, --Cl, --H and --OH and R.sup.6 is selected from the group consisting of hydrogen and --OH;
- ##STR15## wherein each Y is independently --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.7 is selected from the group consisting of --OH, --O-mesityl, --F, --OH and --O-methyl;
- and R.sup.8 is selected from the group consisting of --OH and --O-methyl;
- ##STR16## wherein each Y is independently --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.13 is selected from the group consisting of --F, --N.sub.3, --O-methyl, --H, and --O-benzyl;
- R.sup.14 is selected from the group consisting --O-acetyl, --OH, --O-benzyl, --H and --O-methyl;
- R.sup.15 is selected from the group consisting --O-acetyl, --OH, --O-benzyl, --H and --O-methyl;
- R.sup.16 is selected from the group consisting of --OH, O-acetyl and --O-benzyl;
- and R.sup.17 is selected from the group consisting of --O-acetyl and --OH;
- and ##STR17## wherein each Y is independently --O-- or --NH--, R is an aglycon or from 1-20 carbon atoms, R.sup.18, R.sup.19 and R.sup.20 are --O-benzyl and R.sup.21 is --O-acetyl or --OH.
A compound useful as an .alpha.-glucosidase I inhibitor or as an intermediate in the production of .alpha.-glucosidase I inhibitor selected from the group consisting of compounds represented by formulas V, VI, IX, X, XI, XII and XIII:
- ##STR24## wherein each Y is independently --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.9 is selected from the group consisting of --O-mesityl, --N.sub.3, --NH.sub.2, --Cl, --F, --H, --OH, and --O-methyl and R.sup.10 is selected from the group consisting of --OH, --H and --O-methyl, with the proviso that when each Y is --O-- and R.sup.9 is hydroxyl, then R.sup.10 is not hydroxyl;
- ##STR25## wherein each Y is independently --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.11 is selected from the group consisting of --O-mesityl, --N.sub.3, --NH.sub.2, --Cl, --F, --H, --OH and --O-methyl and R.sup.12 is selected from the group consisting of --OH, --H and --O-methyl with the proviso that when each Y is --O-- and R.sup.11 is hydroxyl, then R.sup.12 is not hydroxyl;
- ##STR26## wherein each Y is independently selected from --O-- or --NH--, R is an aglycon of from 1-20 carbon atoms, R.sup.22 is selected from the group consisting of --F, --N.sub.3, --NH.sub.2, --O-methyl, --H and --OH;
- and R.sup.23 and R.sup.24 are selected from the group consisting of --OH, --H and --O-methyl with the proviso that when each Y is --O--, R.sup.22 is hydroxyl and R.sup.23 is hydroxyl, then R.sup.24 is not hydroxyl;
- ##STR27## wherein each Y is independently --O-- or --NH-- and R is an aglycon of from 1-20 carbon atoms;
- ##STR28##
Dependencies are inferred from the claim text.