Compounds and their uses
First Claim
Patent Images
1. A compound represented by the general formula:
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X-β
1,6-pinitol wherein,X represents a sugar residue;
the sugar residue is substituted with one, two or three groups, and the pinitol is unsubstituted or is further substituted with between one and four groups, said substituted groups being substituted on at least one of said sugar residue and said pinitol and being independently selected from the group consisting of;
(a) a phosphoryl group having a formula selected from the group consisting of —
O—
P(O)(OH)2, —
O—
P(S)(OH)2, —
O—
P(O)(OR)2, —
O—
P(S)(OR)2, —
O—
P(O)OHR, —
O—
P(S)OHR, —
O—
P(O)OR1R2, —
O—
P(S)OR1R2, —
O—
P(S)(OH)(SH), or a cyclic phosphate;
(b) a phosphorus-containing group having a formula selected from the group consisting of —
O—
P(OR)—
NR1R2 and —
O—
P(O)(OR)—
NR1R2;
(c) a sulphur-containing group having a formula selected from the group consisting of —
O—
S(O)(OH)2, —
SH, —
SR, —
S(—
O)—
R, —
S(O)2R, RO—
S(O)2−
, —
O—
SO2NH2, —
O—
SO2R1R2 or —
NHSO2NH2;
(d) a substituted amino-containing group having a formula selected from the group consisting of —
NHR, —
NR1R2, —
NHAc, —
NHCOR, —
NH—
O—
COR, —
NHSO3−
, —
NHSO2R, —
N(SO2R), —
NHC(═
NH)NH2, —
NH—
CO—
NR1R2 or —
NH—
C(S)—
NH2;
(e) a hydroxy group;
a substituted hydroxy group represented by the formula —
OR3, where R3 is C1-10 unsubstituted alkyl or C1-10 substituted alkyl, alkoxyalkyl, aryloxyalkyl, cycloalkyl, alkenylalkyl in which the alkyl group is unsubstituted, alkylene-cycoalkyl in which the cycloalkyl group has 3-7 carbon atoms, —
OCOR, aryl, heteroaryl, acetal, or said substituted groups comprise two hydroxyl groups that are joined to form a ketal;
(f) halogen substituents fluorine or chlorine; and
(g) hydrogen, forming a deoxy sugar;
wherein R, R1 and R2 are independently hydrogen or C1-10 unsubstituted alkyl or C1-10 substituted alkyl or aryl;
or a derivative of the compound, said derivative comprising salts, coordination complexes with metal ions, esters, free acids or bases, hydrates or protecting groups.
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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, such as the chiro-inositol derivative pinitol (3-O-methyl-chiro-inositol).
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Citations
25 Claims
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1. A compound represented by the general formula:
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X-β
1,6-pinitolwherein, X represents a sugar residue;
the sugar residue is substituted with one, two or three groups, and the pinitol is unsubstituted or is further substituted with between one and four groups, said substituted groups being substituted on at least one of said sugar residue and said pinitol and being independently selected from the group consisting of;
(a) a phosphoryl group having a formula selected from the group consisting of —
O—
P(O)(OH)2, —
O—
P(S)(OH)2, —
O—
P(O)(OR)2, —
O—
P(S)(OR)2, —
O—
P(O)OHR, —
O—
P(S)OHR, —
O—
P(O)OR1R2, —
O—
P(S)OR1R2, —
O—
P(S)(OH)(SH), or a cyclic phosphate;
(b) a phosphorus-containing group having a formula selected from the group consisting of —
O—
P(OR)—
NR1R2 and —
O—
P(O)(OR)—
NR1R2;
(c) a sulphur-containing group having a formula selected from the group consisting of —
O—
S(O)(OH)2, —
SH, —
SR, —
S(—
O)—
R, —
S(O)2R, RO—
S(O)2−
, —
O—
SO2NH2, —
O—
SO2R1R2 or —
NHSO2NH2;
(d) a substituted amino-containing group having a formula selected from the group consisting of —
NHR, —
NR1R2, —
NHAc, —
NHCOR, —
NH—
O—
COR, —
NHSO3−
, —
NHSO2R, —
N(SO2R), —
NHC(═
NH)NH2, —
NH—
CO—
NR1R2 or —
NH—
C(S)—
NH2;
(e) a hydroxy group;
a substituted hydroxy group represented by the formula —
OR3, where R3 is C1-10 unsubstituted alkyl or C1-10 substituted alkyl, alkoxyalkyl, aryloxyalkyl, cycloalkyl, alkenylalkyl in which the alkyl group is unsubstituted, alkylene-cycoalkyl in which the cycloalkyl group has 3-7 carbon atoms, —
OCOR, aryl, heteroaryl, acetal, or said substituted groups comprise two hydroxyl groups that are joined to form a ketal;
(f) halogen substituents fluorine or chlorine; and
(g) hydrogen, forming a deoxy sugar;
wherein R, R1 and R2 are independently hydrogen or C1-10 unsubstituted alkyl or C1-10 substituted alkyl or aryl;
or a derivative of the compound, said derivative comprising salts, coordination complexes with metal ions, esters, free acids or bases, hydrates or protecting groups. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13)
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9. A compound selected from the group consisting of:
- O-(2-amino-2-deoxy-glucopyranosyl)-β
(1,6)-D-3-O-methyl-chiro-inositol;
O-(2-amino-2-deoxy-D-glucopyranosyl)-α
(1,6)-D-3-O-methyl-chiro-inositol;
O-(2-amino-2-deoxy-D-galactopyranosyl)-α
(1,6)-D-3-O-methyl-chiro-inositol; and
1′
-D-6-O-(2′
-amino-2′
-deoxy-β
-D-galactopyranosyl)-3-O-methyl-D-chiro-inositol;
or a derivative of said compound, said derivative comprising salts, coordination complexes with metal ions, free acids or bases, hydrates or protecting groups.
- O-(2-amino-2-deoxy-glucopyranosyl)-β
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14. A compound represented by the general formula:
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X-β
1,6-pinitolwherein; X represents a sugar residue;
the sugar residue is substituted with between one and four groups, and the pinitol is further substituted with one, two or three groups, said substituted groups being substituted on at least one of said sugar residue and said pinitol and being independently selected from the group consisting of;
(a) a phosphoryl group having a formula selected from the group consisting of —
O—
P(O)(OH)2, —
O—
P(S)(OH)2, —
O—
P(O)(OR)2, —
O—
P(S)(OR)2, —
O—
P(O)OHR, —
O—
P(S)OHR, —
O—
P(O)0R1R2, —
O—
P(S)OR1R2, —
O—
P(S)(OH)(SH), or a cyclic phosphate;
(b) a phosphorus-containing group having a formula selected from the group consisting of —
O—
P(OR)—
NR1R2 and —
O—
P(O)(OR)—
NR1R2;
(c) a sulphur-containing group having a formula selected from the group consisting of —
O—
S(O)(OH)2, —
SH, —
SR, —
S(—
O)—
R, —
S(O)2R, RO—
S(O)2−
, —
O—
SO2NH2, —
O—
SO2R1R2 or —
NHSO2NH2;
(d) a substituted amino-containing group having a formula selected from the group consisting of —
NHR, —
NR1R2, —
NHAc, —
NHCOR, —
NH—
O—
COR, —
NHSO3−
, —
NHSO2R, —
N(SO2R), —
NHC(═
NH)NH2, —
NH—
CO—
NR1R2 or —
NH—
C(S)—
NH2;
(e) a hydroxy group;
a substituted hydroxy group represented by the formula —
OR3, where R3 is C1-10 unsubstituted akyl or C1-10 substituted alkyl, alkoxyalkyl, aryloxyalkyl, cycloalkyl, alkenylalkyl in which the alkyl group is unsubstituted, alkylene-cycoalkyl in which the cycloalkyl group has 3-7 carbon atoms, —
OCOR, aryl, heteroaryl, acetal, or said substituted groups comprise two hydroxyl groups that are joined to form a ketal;
(f) halogen substituents fluorine or chlorine; and
(g) hydrogen, forming a deoxy sugar;
wherein R, R1, and R2 are independently hydrogen or C1-10 unsubstituted alkyl or C1-10 substituted alkyl or aryl;
or a derivative of the compound, said derivative comprising salts, coordination complexes with metal ions, esters, free acids or bases, hydrates or protecting groups. - View Dependent Claims (15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25)
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Specification