Treatment of inflammatory bowel disease

1 . A method comprising administering a compound to a mammal suffering from an inflammatory bowel disease for the treatment of said disease, said compound represented by the general formula I;

wherein hatched lines represent the α configuration, a triangle represents the β configuration, a wavy line represents either the α configuration or the β configuration and a dotted line represents the presence or absence of a double bond;

A and B are independently selected from the group consisting of O, S and CH 2 , provided that at least one of A or B is S;

D represents a covalent bond or CH 2 , O, S or NH;

X is CO 2 R, CONR 2 , CH 2 OR, P(O)(OR) 2 , CONRSO 2 R, SONR 2 or

Y is O, OH, OCOR 2 , halogen or cyano;

Z is CH 2 or a covalent bond;

R is H or R 2 ;

R 1 is H, R 2 , phenyl, or COR 2 ;

R 2 is C 1 -C 5 lower alkyl or alkenyl;

R 3 is benzothienyl, benzofuranyl, naphthyl, or substituted derivatives thereof, wherein the substituents maybe selected from the group consisting of C 1 -C 5 alkyl, halogen, CF 3 , CN, NO 2 , NR 2 , CO 2 R and OR and R 4 is hydrogen or C 1 -C 5 lower alkyl.

2 . The method according to claim 1 wherein said compound is represented by the general formula II;

3 . The method according to claim 2 wherein said compound is represented by the general formula III;

4 . The method of claim 1 wherein Z represents a covalent bond.

5 . The method of claim 1 wherein D represents a covalent bond or is CH 2 .

6 . The method of claim 1 wherein X is CO 2 R.

7 . The method of claim 6 wherein R is selected from the group consisting of H, methyl, i-propyl, and n-propenyl.

8 . The method of claim 1 wherein R is H, or n-propenyl.

9 . The method of claim 1 wherein R 1 is H.

10 . The method of claim 1 wherein D is CH 2 .

11 . The method of claim 10 wherein R 3 is benzo[b]thienyl, 3-chlorobenzo[b]thienyl or naphthyl.

12 . The method of claim 1 wherein said compound is selected from the group consisting of

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-(hydroxy)-5-(naphthyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-(hydroxy)-5-(naphthyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-(hydroxy)-5-(naphthyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid isopropyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxy-5-(benzothienyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxy-5-(benzothienyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxy-5-(benzothienyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid isopropyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxy-5-(benzofuranyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxy-5-(benzofuranyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxy-5-(benzofuranyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid isopropyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((E)-3-hydroxy-4-naphthalen-2-yl-but-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((E)-3-hydroxy-4-naphthalen-2-yl-but-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid,

{3-[(1R,2S,3R)-2-((E)-4-Benzo[b]thiophen-3-yl-3-hydroxybut-1-enyl)-3-hydroxy-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester,

{3-[(1R,2S,3R)-2-((E)-4-Benzo[b]thiophen-3-yl-3-hydroxybut-1-enyl)-3-hydroxy-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-(hydroxy)-3-(methyl)-5-(naphthyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((E)-3-hydroxy-3-methyl-4-naphthalen-2-yl-but-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester,

{3-[(1R,2S,3R)-3-Hydroxy-2-((E)-3-hydroxy-3 methyl-4-naphthalen-2-yl-but-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-(hydroxy)-3-(methyl)-5-(naphthyl)but-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid,

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-(hydroxy)-3-(methyl)-5-(benzothienyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester and

{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-(hydroxy)-3-(methyl)-5-(benzothienyl)pent-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid methyl ester.

13 . The method of claim 1 wherein D is CH 2 and Z represents a covalent bond.

14 . The method of claim 1 wherein R 4 is hydrogen or methyl.

15 . The method of claim 1 wherein R 4 is hydrogen.

16 . The method of claim 1 wherein said irritable bowel disease is Crohn's disease.

17 . The method of claim 1 wherein said irritable bowel disease is ulcerative colitis.

18 . An oral or rectal dosage form comprising a therapeutically effective amount of a compound represented by the general Formula 1

wherein hatched lines represent the α configuration, a triangle represents the β configuration, a wavy line represents the α configuration or the β configuration and a dotted line represents the presence or absence of a double bond;

A and B are independently selected from the group consisting of O, S and CH 2 ;

provided that at least one of A or B is S;

D represents a covalent bond or CH 2 , O, S or NH;

X is CO 2 R, CONR 2 , CH 2 OR, P(O)(OR) 2 , CONRSO 2 R SONR 2 or

Y is O, OH, OCOR 2 , halogen or group;

Z is CH 2 or a covalent bond;

R is H or R 2 ;

R 1 is H, R 2 , phenyl, or COR 2 ;

R 2 is C 1 -C 5 lower alkyl or alkenyl; and

R 3 is benzothienyl, benzofuranyl, naphthyl or substituted derivatives thereof, wherein the substituents maybe selected from the group consisting of C 1 -C 5 alkyl, halogen, CF 3 , CN, NO 2 , NR 2 , CO 2 R and OR and R 4 is hydrogen or C 1 -C 5 alkyl.