# US 2004/0147487 A1 · Inositol derivatives for increasing chloride secretion and inhibiting inflammation

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- Number: US 2004/0147487 A1
- Document ID: US20040147487A1
- Status: Published application
- Kind: A1
- Application number: 10/432,340
- Filed: 2004-03-22
- Published: 2004-07-29
- Earliest claimed: 2004-03-22
- Assignees: Inologic, Inc.
- Inventors: Alexis Traylor-Kaplan; Carsten Schultz; Tanja Meyerdierks; Mark Moody; Andrew Schnaars; Jane Smith
- Web page: https://patentgrep.com/patent/US20040147487A1

## CPC

- C07F 9/65522: {condensed with carbocyclic rings or carbocyclic ring systems}
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07F 9/117: with cycloaliphatic alcohols
- C07F 9/65517: {condensed with carbocyclic rings or carbocyclic ring systems}
- C07F 9/65527: {condensed with carbocyclic rings or carbocyclic ring systems}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Inositol derivatives, compositions comprising inositol derivatives, and methods for using compositions comprising inositol derivatives as agents for activating the secretion of chloride ions and/or treatment of inflammation are described.

## Claims

### Claim 1

A compound of the formula:
16
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain, alkyl and —OC1-C20 straight or branched chain alkyl, and —OC2-C20 straight or branched chain alkenyl or alkynyl;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

A compound of claim 1 selected from the group consisting of D-2,3,5-tri-O-butyryl-myo-inositol 1,4,6-trisphosphate hexakis(acetoxymethyl)ester, D-2,3,5-Tri-O-butyryl-myo-inositol 1,4,6-trisphosphate hexakis(propionoxymethyl) ester, and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 3

A compound of the formula:
17
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, and —OC2-C20 straight or branched chain alkenyl or alkynyl;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups, including racemates and diastereomers thereof, with the proviso that the compound of formula (II) is not D-3,6-Di-O-butyryl-myo-inositol 1,2,4,5-tetrakisphosphate octakis(acetoxymethyl) ester; or D-1,4-Di-O-butyryl-myo-inositol 2,3,5,6-tetrakisphosphate octakis(acetoxymethyl)ester;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 4

A compound of the formula:
18
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20 straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2; or each R1 may be taken together to form a cyclic structure;
each R2 is independently selected from a group consisting of hydrogen and —C(R4)(R4)OC(O)C1-C4 straight or branched chain alkyl and each R3 is independently selected from a group consisting of —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —C1-C11—X—Y, where each X is independently selected from a group consisting of —O—, —S—, —Se—, —CO(O)—, —CS(O)—, —CO(S)—, —OC(O)—, —SC(O)—, OC(S)—, or —NH—, and where Y is independently selected from a group consisting of —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 5 (depends on 4)

A compound of claim 4 selected from the group consisting of rac-(3aS, 4R, 5S, 6R, 7S, 7aS)-4,5,6,7-tetrakis[[bis(acetoxymethoxy)phosphoryl]oxy]-2,2-dimethyl-3a-propyl-hexahydrobenzo-(1,3)-dioxol; rac-(1S, 2R, 3S, 4R, 5S, 6S)-4,5,6,7-tetrakis[[bis(acetoxymethoxy)phosphoryl]oxy]-1-butyroxy-6-propoxy-1-propyl-cyclohexane; rac-(1S, 2R, 3S, 4R, 5S, 6S)-2,3,4,5,6-pentakis-[[bis(acetoxy-methoxy)phosphoryl]oxy]-6-butyroxy-2-propyl-cyclohexane; and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 6

A compound of the formula:
19
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain allyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20 straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R4 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R4, except hydrogen, being unsubstituted or substituted with one or more halogen OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups, including racemates and diastereomers thereof; and
each W is independently selected from a group consisting of —C(X)(Y)—, —C(X)(Y)—C(X)(Y)—, and —C(X)(Y)—C(X)(Y)—C(X)(Y)—; where
X and Y are independently selected from a group consisting of hydrogen, —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl, including racemates and diastereomers thereof and hydrogen, —OH, —Oalkyl, —SH, —Salkyl, —CO(O)alkyl, —CS(O)alkyl, —CO(S)alkyl, —OC(O)alkyl, —SC(O)alkyl, —OC(S)alkyl, or —CONH2, or —CONHalkyl, or —CON(alkyl)(alkyl), —NH2; and
n is an integer from 2 to 13, preferably 2 to 5;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 7

A compound of the formula:
20
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20 straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, —OH, C1-C6 alkyl, —NO2, —OC1-C6 alkyl, and —OC(O)C1-C6 alkyl groups, including racemates and diastereomers thereof; and
each V is independently selected from a group consisting of —C(X)(Y)—, —C(X)(Y)—C(X)(Y)—, or —C(X)(Y)—C(X)(Y)—C(X)(Y)—; and
m is an integer from 2 to 15, preferably from 2 to 5; and
each W is independently selected from a group consisting of —C(X)—, —C(X)—C(X)(Y)—, or —C(X)—C(X)(Y)—C(X)(Y)—; and
n is an integer from 1 to 15, preferably from 1 to 3; and
X and Y are independently selected from a group consisting of hydrogen, —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl, including racemates and diastereomers thereof and hydrogen, —OH, —Oalkyl, —SH, —Salkyl, —CO(O)alkyl, —CS(O)alkyl, —CO(S)alkyl, —OC(O)alkyl, —SC(O)alkyl, —OC(S)alkyl, or —CONH2, or —CONHalkyl, or —CON(alkyl)(alkyl), —NH2;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 8

A method for regulating chloride secretion and/or inhibiting inflammation in a cell or tissue, comprising contacting the cell or tissue with an effective amount of a compound of formula (I):
21
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight- or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, and —OC2-C20 straight or branched chain alkenyl or alkynyl;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 9 (depends on 8)

A method of claim 8, wherein the compound is selected from the group consisting of D-2,3,5-tri-O-butyryl-myo-inositol 1,4,6-trisphosphate hexakis-(acetoxymethyl) ester; D-2,3,5-Tri-O-butyryl-myo-inositol 1,4,6-trisphosphate hexakis(propionoxymethyl)ester, and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 10

A method of regulating chloride secretion and/or inhibiting inflammation in a human or animal patient in need thereof comprising administering to the patient a therapeutically effective amount of a compound of the formula:
22
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, and —OC2-C20 straight or branched chain alkenyl or alkynyl;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 11 (depends on 10)

A method of claim 10, wherein the compound is selected from the group consisting of D-2,3,5-tri-O-butyryl-myo-inositol 1,4,6-trisphosphate hexakis-(acetoxymethyl) ester; D-2,3,5-Tri-O-butyryl-myo-inositol 1,4,6-trisphosphate hexakis(propionoxymethyl)ester, and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 12

A method for regulating chloride secretion and/or inhibiting inflammation in a cell or tissue, comprising contacting the cell or tissue with an effective amount of a compound of formula (II):
23
each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, and —OC2-C20 straight or branched chain alkenyl or alkynyl;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, —NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 13 (depends on 12)

A method of claim 12, wherein the compound is selected from the group consisting of D-3,6-di-O-butyryl-myo-inositol 1,2,4,5-tetrakisphosphate octakis(propionoxymethyl)ester, D-1,4-di-O-butyryl-myo-inositol 2,3,5,6-tetrakis-phosphate octakis(propionoxymethyl)ester, and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 14

A method of regulating chloride secretion and/or inhibiting inflammation in a human or animal patient in need thereof comprising administering to the patient a therapeutically effective amount of a compound of the formula:
24
each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain allyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, and —OC2-C20 straight or branched chain alkenyl or alkynyl;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, —NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 15 (depends on 14)

A method of claim 14, wherein the compound is selected from the group consisting of D-3,6-di-O-butyryl-myo-inositol 1,2,4,5-tetrakisphosphate octakis(propionoxymethyl)ester; D-1,4-di-O-butyryl-myo-inositol 2,3,5,6-tetrakis-phosphate octakis(propionoxymethyl)ester, and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 16

A method for regulating chloride secretion and/or inhibiting inflammation in a cell or tissue, comprising contacting the cell or tissue with an effective amount of a compound of formula (III):
25
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain al. V, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20 straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2; or each R1 may be taken together to form a cyclic structure;
each R2 is independently selected from a group consisting of hydrogen and —C(R4)(R4)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —C1-C11—X—Y, where each X is independently selected from a group consisting of —O—, —S—, —Se—, —CO(O)—, —CS(O)—, —CO(S)—, —OC(O)—, —SC(O)—, OC(S)—, or —NH—, and where Y is independently selected from a group consisting of —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl, including racemates and diastereomers thereof.
each R4 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R4 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R4, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 al, and OC(O)C1-C6 alkyl groups;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 17 (depends on 16)

A method of claim 16 wherein the compound is selected from the group consisting of rac-(3aS, 4R, 5S, 6R, 7S, 7aS)4,5,6,7-tetrakis[[bis(acetoxy-methoxy)phosphoryl]oxy]-2,2-dimethyl-3a-propyl-hexahydrobenzo-(1,3)-dioxol; rac-(1S, 2R, 3S, 4R, 5S, 6S)-4,5,6,7-tetrakis[[bis(acetoxymethoxy)phosphoryl]oxy]-1-butyroxy-6-propoxy-1-propyl-cyclohexane; rac-(1S, 2R, 3S, 4R, 5S, 6S)-2,3,4,5,6-pentakis-[[bis(acetoxymethoxy)phosphoryl]oxy]-6-butyroxy-2-propyl-cyclohexane; and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 18

A method of regulating chloride secretion and/or inhibiting inflammation in a human or animal patient in need thereof comprising administering to the patient a therapeutically effective amount of a compound of the formula (III):
26
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20 straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2; or each R1 may be taken together to form a cyclic structure;
each R2 is independently selected from a group consisting of hydrogen and —C(R4)(R4)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —C1-C11—X—Y, where each X is independently selected from a group consisting of —O—, —S—, —Se—, —CO(O)—, —CS(O)—, —CO(S)—, —OC(O)—, —SC(O)—, OC(S)—, or —NH—, and where Y is independently selected from a group consisting of —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl, including racemates and diastereomers thereof
each R4 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R4 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R4, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 19 (depends on 18)

A method of claim 18 wherein the compound is selected from the group consisting of rac-(3aS, 4R, 5S, 6R, 7S, 7aS)4,5,6,7-tetrakis[[bis(acetoxymethoxy)phosphoryl]oxy]-2,2-dimethyl-3a-propyl-hexahydrobenzo-(1,3)-dioxol; rac-(1S, 2R, 3S, 4R, 5S, 6S)-4,5,6,7-tetrakis[[is(acetoxymethoxy)phosphoryl]oxy]-1-butyroxy-6-propoxy-1-propyl-cyclohexane; rac-(1S, 2R, 3S, 4R, 5S, 6S)-2,3,4,5,6-pentakis-[[bis(acetoxy-methoxy)phosphoryl]oxy]-6-butyroxy-2-propyl-cyclohexane; and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 20

A method for regulating chloride secretion and/or inhibiting inflammation in a cell or tissue, comprising contacting the cell or tissue with an effective amount of a compound of formula (IV):
27
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20′ straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups, including racemates and diastereomers thereof; and
each W is independently selected from a group consisting of —C(X)(Y)—, —C(X)(Y)—C(X)(Y)—, and —C(X)(Y)—C(X)(Y)—C(X)(Y)—; where
X and Y are independently selected from a group consisting of hydrogen, —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl, including racemates and diastereomers thereof and hydrogen, —OH, —Oalkyl, —SH, —Salkyl, —CO(O)alkyl, —CS(O)alkyl, —CO(S)alkyl, —OC(O)alkyl, —SC(O)alkyl, —OC(S)alkyl, or —CONH2, or —CONHalkyl, or —CON(alkyl)(alkyl), —NH2; and
n is an integer from 2 to 13, preferably 2 to 5;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 21 (depends on 20)

A method of claim 20 wherein the compound is selected from the group consisting of D-2-O-butyryl-1,2,4,5,6-pentahydrobenzoxirane 1,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester; D-2-O-butyryl-2,3,4,5,6-pentahydrobenzoxirane 3,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester; D-2-O-butyryl1,2,4,5,6-pentahydrochroman 1,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester; D-2-O-butyryl-2,3,4,5,6-pentahydrochroman 3,4,5,6-tetraakisphosphate octakis(acetoxymethyl)ester; and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 22

A method of regulating chloride secretion and/or inhibiting inflammation in a human or animal patient in need thereof comprising administering to the patient a therapeutically effective amount of a compound of the formula (T):
28
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20 straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, OH, C1-C6 alkyl, NO2, —OC1-C6 alkyl, and OC(O)C1-C6 alkyl groups, including racemates and diastereomers thereof; and
each W is independently selected from a group consisting of —C(X)(Y)—, —C(X)(Y)—C(X)(Y)—, and —C(X)(Y)—C(X)(Y)—C(X)(Y)—; where
X and Y are independently selected from a group consisting of hydrogen, —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl, including racemates and diastereomers thereof and hydrogen, —OH, —Oalkyl, —SH, —S allyl, —CO(O)alkyl, —CS(O)alkyl, —CO(S)alkyl, —OC(O)alkyl, —SC(O)alkyl, —OC(S)alkyl, or —CONH2, or —CONHalkyl, or —CON(alkyl)(alkyl), —NH2; and
n is an integer from 2 to 13, preferably 2 to 5;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 23 (depends on 22)

A method of claim 22 wherein the compound is selected from the group consisting of D-2-O-butyryl-1,2,4,5,6-pentahydrobenzoxirane 1,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester;
D-2-O-butyryl-2,3,4,5,6-pentahydrobenzoxirane 3,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester, D-2-O-butyryl1,2,4,5,6-pentahydrochroman 1,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester; D-2-O-butyryl-2,3,4,5,6-pentahydrochroman 3,4,5,6-tetrakisphosphate octakis(acetoxymethyl)ester; and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 24

A method for regulating chloride secretion and/or inhibiting inflammation in a cell or tissue, comprising contacting the cell or tissue with an effective amount of a compound of formula (V):
29
wherein each R1 is independently selected from the group consisting of hydrogen, —OH, —C1-C20 straight or branched chain alkyl, —C2-C20 straight or branched chain alkenyl or alkynyl, —OC(O)C1-C20 straight or branched chain alkyl and —OC1-C20 straight or branched chain alkyl, —OC2-C20 straight or branched chain alkenyl or alkynyl, and —OPO(OR2)2;
each R2 is independently selected from a group consisting of hydrogen and —C(R3)(R3)OC(O)C1-C4 straight or branched chain alkyl; and
each R3 is independently selected from a group consisting of hydrogen and —C1-C12 alkyl, both R3 taken as a 5- or 6-membered ring, phenyl, and benzyl, said R3, except hydrogen, being unsubstituted or substituted with one or more halogen, —OH, C1-C6 alkyl, —NO2, —OC1-C6 allyl, and —OC(O)C1-C6 alkyl groups, including racemates and diastereomers thereof; and
each V is independently selected from a group consisting of —C(X)(Y)—, —C(X)(Y)—C(X)(Y)—, or —C(X)(Y)—C(X)(Y)—C(X)(Y)—; and
m is an integer from 2 to 15, preferably from 2 to 5; and
each W is independently selected from a group consisting of —C(X)—, —C(X)—C(X)(Y)—, or —C(X)—C(X)(Y)—C(X)(Y)—; and
n is an integer from 1 to 15, preferably from 1 to 3; and
X and Y are independently selected from a group consisting of hydrogen, —C1-C11 straight or branched chain alkyl, —C2-C12 straight or branched chain alkenyl or alkynyl, or unsubstituted and substituted benzyl, and phenyl, including racemates and diastereomers thereof and hydrogen, —OH, —Oalkyl, —SH, —Salkyl, —CO(O)alkyl, —CS(O)alkyl, —CO(S)alkyl, —OC(O)alkyl, —SC(O)alkyl, —OC(S)alkyl, or —CONH2, or —CONHalkyl; or —CON(alkyl)(alkyl), —NH2;
and the racemates, diastereomers and pharmaceutically acceptable salts thereof.

### Claim 25 (depends on 24)

A method of claim 24 wherein the compound is selected from the group consisting of (1S, 2R, 3S, 4R, 5S, 6S, 8R)-2,3,4,5-tetrakis[[bis(acetoxymethoxy)phosphoryl]oxy]-7,12-dioxa-tricyclo-[6.3.1.01,6]-dodecane; and the racemates, diastereomers and pharmaceutically acceptable salts thereof.