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US 5,489,675 AGranted
Disaccharide sialidase substrates and inhibitors
AssigneeE. I. Du Pont de Nemours and Company
InventorSubramaniam Sabesan
Life of this patent
Estimating the term…
Abstract
Novel NeuAc-Gal dissacharide sialidase substrates and inhibitors which are locked into rigid conformation by the attachment of an alkyl group at the C-6 arm of the galactose core are provided. Also provided is a method for the inhibition of sialidase activity.
Claims12
A compound of formula I or II, ##STR8## wherein R is H or a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl;
- R.sup.1 is H, a C.sub.1 to C.sub.20 alkyl, a mono, di or polyvalent cation of an alkali metal, alkaline earth metal or transition metal, or an ammonium or substituted ammonium ion;
- X is O, S, CR.sup.4 R.sup.5 or NR.sup.6, wherein R.sup.4, R.sup.5 and R.sup.6 are each independently H or a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl;
- R.sup.2 is a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl;
- R.sup.3 and R.sup.3 ' are H, OH, a C.sub.1 to C.sub.20 alkoxy or substituted alkoxy, a mono, di or oligosaccharide, or a C.sub.1 to C.sub.20 alkylideneoxy taken together with R.sup.7 ' when R.sup.7 ' is not H;
- provided that one of R.sup.3 or R.sup.3 ' must be H but R.sup.3 and R.sup.3 ' may not both be H;
- R.sup.7 and R.sup.7 ' are independently H, a C.sub.1 to C.sub.20 acyl, a C.sub.1 to C.sub.20 alkyl, or a C.sub.1 to C.sub.20 alkylidene taken together with an adjacent R.sup.3 ', R.sup.7 or R.sup.7 ';
- and
- R.sup.8 is H, a C.sub.1 to C.sub.20 acyl, or a C.sub.1 to C.sub.20 alkyl.
5 more elements
A compound of formula III or IV, ##STR9## wherein R.sup.1 is a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl;
- R.sup.2 is a C.sub.1 to C.sub.20 alkyl, or a C.sub.1 to C.sub.20 alkylidene taken together with R.sup.3 ;
- R.sup.3 is a C.sub.1 to C.sub.20 alkyl, or a C.sub.1 to C.sub.20 alkylidene taken together with R.sup.2 ;
- R.sup.4 is a C.sub.1 to C.sub.20 alkyl, or a C.sub.1 to C.sub.20 alkylidene taken together with R.sup.5 when R.sup.5 is alkylideneoxy;
- R.sup.5 is H, a C.sub.1 to C.sub.20 alkoxy, or a C.sub.1 to C.sub.20 alkylideneoxy taken together with R.sup.4 ;
- R.sup.5 ' is H, a C.sub.1 to C.sub.20 alkoxy, or 2-(trimethylsilyl)ethoxy,or a mono, di or
- oligosaccharide;
- provided that one of R.sup.5 or R.sup.5 ' must be H and R.sup.5 and R.sup.5 ' may not both be H;
- X is S, or NR.sup.6, wherein R.sup.6, is H or a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl.
5 more elements
A compound of formula III or IV, ##STR10## wherein X is O;
- R.sup.1 is a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl or acetyl or benzyl;
- R.sup.2, R.sup.3 and R.sup.4 are independently H, C.sub.1 to C.sub.20, alkyl, acetyl, or benzyl;
- and
- R.sup.5 is H;
- R.sup.5 ' is C.sub.1 to C.sub.20 alkoxy, or 2-(trimethylsilyl)ethoxy.
2 more elements
Dependencies are inferred from the claim text.