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US 2001/0056072 A1Published application
Compounds and their uses
OwnerManuel Martin-Lomas, Thomas William Rademacher +2inventors
InventorsManuel Martin-Lomas, Thomas William Rademacher, Hugo Norberto Caro, Irene Francois
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Abstract
Compounds having a mimetic or antagonistic property of an inositol phosphoglycan, and the uses of these compounds are disclosed, together with the use, e.g. to treat a condition ameliorated by administration of an IPG second messenger or an IPG antagonist thereof. Preferred compounds of the invention are based on the substituted cyclitols, and in particular cyclitols linked to a sugar moiety where the molecule is substituted with a negatively charged group such as phosphate.
Claims14
A compound represented by the general formula:
- X-cyclitol
- wherein:
- X represents a sugar residue, the sugar residue is substituted with one or more negatively charged groups;
- the sugar residue and cyclitol are linked by an α or β linkage other than a β1,4 linkage;
- the sugar residue is optionally further substituted with between one and three groups, and the cyclitol is unsubstituted or is substituted with between one and five groups, the group or groups independently selected from:
- (a) phosphoryl groups such as phosphate —O—P(O)(OH)2;
- thiophosphate —O—P(S)(OH)2;
- phosphate esters —O—P(O)(OR)2;
- thiophosphate esters —O—P(S)(OR)2;
- phosphonate —O—P(O)OHR;
- thiophosphonate —O—P(S)OHR;
- substituted phosphonate —O—P(O)OR1R2;
- substituted thiophosphonate —O—P(S)OR1R2;
- —O—P(S)(OH)(SH);
- cyclic phosphate;
- (b) other phosphorus containing compounds such as phosphoramidite —O—P(OR)—NR1R2 and phosphoramidate —O—P(O)(OR)—NR1R2;
- (c) sulphur groups such as —O—S(O)(OH), —SH, —SR, —S(—O)—R, —S(O)2R, RO—S(O)2−, —O—SO2NH2, —O—SO2R1R2 or sulphamide —NHSO2NH2;
- (d) amino groups such as —NHR, —NR1R2, —NHAc, —NHCOR, —NH—O—COR, —NHSO3−, —NHSO2R, —N(SO2R)2, and/or amidino groups such as —NH—C(═NH)NH2 and/or ureido groups such as —NHCO—NR1R2 or thiouriedo groups such as —NH—C(S)—NH2;
- (e) hydroxy groups and substituted hydroxy groups such as —OR3, where R3 is C1-10 unsubstituted or substituted alkyl, e.g. CHF2 or CF3, alkoxyalkyl, aryloxyalkyl, cycloalkyl, alkenyl (unsubstituted alkyl), alkylene (C3-7 cycloalkyl), —OCOR, aryl, heteroaryl, acetal, or where two hydroxyl groups are joined as a ketal;
- (f) halogen substituents such as fluorine or chlorine;
- (g) hydrogen, e.g. to provide a deoxy sugar;
- wherein R, R1 and R2 are independently hydrogen or C1-10 unsubstituted or substituted alkyl or aryl;
- or a derivative thereof.
20 more elements
A compound represented by the general formula:
- X-α1,6-cyclitol
- wherein:
- X represents a sugar residue;
- the sugar residue is substituted with one or more negatively charged groups;
- the sugar residue is optionally further substituted with between one and three groups, and the cyclitol is unsubstituted or is substituted with between one and five groups, the group or groups independently selected from:
- (a) phosphoryl groups such as phosphate —O—P(O)(OH)2;
- thiophosphate —O—P(S)(OH)2;
- phosphate esters —O—P(O)(OR)2;
- thiophosphate esters —O—P(S)(OR)2;
- phosphonate —O—P(O)OHR;
- thiophosphonate —O—P(S)OHR;
- substituted phosphonate —O—P(O)OR1R2;
- substituted thiophosphonate —O—P(S)OR1R2;
- —O—P(S)(OH)(SH);
- cyclic phosphate;
- (b) other phosphorus containing compounds such as phosphoramidite —O—P(OR)—NR1R2 and phosphoramidate —O—P(O)(OR)—NR1R2;
- (c) sulphur groups such as —O—S(O)(OH), —SH, —SR, —S(—O)—R, —S(O)2R, RO—S(O)2−, —O—SO2NH2, —O—SO2R1R2 or sulphamide —NHSO2NH2;
- (d) amino groups such as —NHR, —NR1R2, —NHAc, —NHCOR, —NH—O—COR, —NHSO3−, —NHSO2R, —N(SO2R)2, and/or amidino groups such as —NH—C(═NH)NH2 and/or ureido groups such as —NH—CO—NR1R2 or thiouriedo groups such as —NH—C(S)—NH2;
- (e) hydroxy groups and substituted hydroxy groups such as —OR3, where R3 is C1-10 unsubstituted or substituted alkyl, e.g. CHF2 or CF3, alkoxyalkyl, aryloxyalkyl, cycloalkyl, alkenyl (unsubstituted alkyl), alkylene (C3-7 cycloalkyl), —OCOR, aryl, heteroaryl, acetal, or where two hydroxyl groups are joined as a ketal;
- (f) halogen substituents such as fluorine or chlorine;
- (g) hydrogen, e.g. to provide a deoxy sugar;
- wherein R, R1 and R2 are independently hydrogen or C1-10 unsubstituted or substituted alkyl or aryl;
- or a derivative thereof.
20 more elements
Dependencies are inferred from the claim text.