EP1 receptor ligands

1. A compound of general formula I:

wherein:

W 1 is a phenyl ring;

W 2 is a 6-membered heterocyclic ring that contains at least 1 N atom and can additionally contain 1 or 2 heteroatoms selected from the group consisting of N, O, and S; wherein said 6-membered heterocyclic ring is aromatic, partially unsaturated or saturated, and which is optionally substituted by one or more R 3 ;

R 1 is -R 6 -R 7 ;

each R 2 is independently selected from the group consisting of H, halogen, C 1-6 -alkyl, C 1-6 -haloalkyl, —O—C 1-6 -alkyl, —O—C 1-6 -haloalkyl, hydroxyC 1-6 -alkyl, CN, —NR 14 COR 15 , —NR 14 SO 2 R 15 and —SO 2 R 15 ;

each R 3 is independently selected from the group consisting of H, halogen, C 1-6 -alkyl C 1-6 -haloalkyl, —O—C 1-6 -alkyl, —O—C 1-6 -haloalkyl, hydroxyC 1-6 -alkyl, —C 1-4 -alkylene-OR 14 , —C 2-4 -alkenylene-COOH, ═O and CN;

each R 4 is independently selected from the group consisting of H and C 1-6 -alkyl, or both R 4 together with the C atom to which they are bonded form a C 3-6 cycloalkyl;

R 5 is selected from the group consisting of H, halogen, C 1-6 -haloalkyl, —O—C 1-6 -alkyl, —O—C 1-6 -haloalkyl, -OH, C 1-6 -alkyl, C 3-6 cycloalkyl and —SO 2 R 15 ;

R 6 is selected from the group consisting of a direct bond, —C 1-4 -alkylene-, —O—C 1-4 -alkylene-and —C 2-4 -alkenylene-;

R 7 is selected from the group consisting of —CO 2 H, —SO 3 H, 5-tetrazolyl, —OPO 3 H 2 , —PO 3 H 2 , —CONR 12 R 12 , —CONH—SO 2 R 12 , —NR 14 CONR 14 —SO 2 R 15 and —SO 2 —NHCOR 15

Y is selected from the group consisting of —C 2-4 -alkylene-, —O—C 1-4 -alkylene-, —C 2-4 -alkenylene-, —C 1-4 -alkylene-O—, —NR 13 —C 1-4 -alkylene- and —C 1-4 -alkylene-NR 13 —;

B is selected from the group consisting of C 2-6 -alkyl, C 2-6 alkenyl and Cy, any of them optionally substituted by one or more R 8 ;

each R 8 is independently selected from the group consisting of halogen, C 1-6 -haloalkyl, —O—C 1-6 -alkyl, —O—C 1-6 -haloalkyl, C 1-6 -alkyl, —OH, —CN, —CH 2 OR 14 and —CONR 12 R 12 ;

each R 9 is independently selected from the group consisting of CR 10 and N;

each R 10 is independently selected from the group consisting of H, halogen, C 1-6 -alkyl, C 1-6 -haloalkyl, —O—C 1-6 -alkyl, —O—C 1-6 -haloalkyl and hydroxyC 1-6 -alkyl;

R 11 is CR 5 or N,

each R 12 is independently selected from the group consisting of H, C 1-6 -alkyl, C 1-6 -haloalkyl, —NR 14 R 14 and C 3-6 cycloalkyl;

each R 13 is independently selected from the group consisting of H, C 1-6 -alkyl, C 1-6 -haloalkyl, and C 3-6 cycloalkyl;

each R 14 is independently selected from the group consisting of H and C 1-6 -alkyl;

each R 15 is independently selected from the group consisting of C 1-6 -alkyl;

Cy is a 3-6 membered monocyclic or 8-12 membered polycyclic ring which can be carbocyclic or heterocyclic containing 1 to 3 heteroatoms selected from N, O and S and which can be aromatic, partially unsaturated or saturated and wherein one or more C or S atoms in Cy can be oxidized to form CO, SO or SO 2 ;

with the proviso that when W1 and W2 is a benzimidazole, R6 and R7 are not at the same time respectively a —O—C 1-4 -alkylene- and a —CO 2 H or that R 7 is not —CONH—SO 2 R 12 ;

and the salts and prodrugs thereof.

2. The compound according to claim 1 wherein each R 9 is CR 10 and each R 10 is H.

3. The compound according to claim 1 , wherein each R 4 is H.

4. The compound according to claim 1 , wherein Y is —O—CH 2 — or —CH 2 —O—, preferably —O—CH 2 —.

5. The compound according to claim 1 , where R 11 is CR 5 and R 5 is selected from the group consisting of H, halogen and —C 1-6 -haloalkyl.

6. The compound according to claim 1 , wherein B is phenyl, C 3-6 -cycloalkyl, C 2-6 -alkyl, C 2-6 alkenyl or is a 5-6 membered monocyclic heterocycle containing 1 or 2 N atom which can be aromatic, partially unsaturated or saturated, any of them optionally substituted by one or more R 8 .

7. The compound according to claim 1 , wherein B is phenyl optionally substituted by 1 to 5 R 8 .

8. The compound according to claim 1 , wherein

represents

where E 1 , E 2 and E 3 are CR 2 ; or one of E 1 , E 2 or E 3 is N and the others are CR 2 ; or two of E 1 , E 2 or E 3 are N and the other is CR 2 .

9. The compound according to claim 1 , wherein

represents

where G is selected from the group consisting of CR 3 , CR 3 R 3 , OCR 3 R 3 ; OCR 3 ; CR 3 R 3 —CR 3 R 3 and N;

D is selected from the group consisting of CR 3 , CR 3 R 3 and N;

- - - represents a single bond or a double bond.

10. The compound according to claim 1 wherein

is selected from the group consisting of

11. The compound according to claim 10 wherein

represents

12. The compound according to claim 1 , wherein R 6 is a direct bond and R 7 is —CO 2 H.

13. The compound according to claim 1 , wherein each R 2 is independently selected from the group consisting of H and halogen and each R 3 is H.

14. A compound according to claim 1 selected from:

1-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-((2,4-difluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

4-(5-chloro-2-cyclobutoxybenzyl)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-bromo-2-(4-chloro-2-fluorobenzyloxy)benzyl)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-chloro-2-(2-fluoro-2-methylpropoxy)benzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)-3,4dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-chloro-2-((2,4-difluorobenzyl)oxy)benzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(2-((4-chloro-2-fluorobenzyl)oxy)benzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(2-(benzyloxy)benzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(2-((2-chloro-4-fluorobenzyl)oxy)-5-fluorobenzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(2-((2,4-difluorobenzyl)oxy)benzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

1-(2-((2,4-difluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-((2,4-difluorobenzyl)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-(cyclobutylmethoxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-isobutoxybenzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-[5-chloro-2-(1,2-dimethylpropoxy)benzyl]-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-[5-chloro-2-(2-fluoro-2-methylpropoxy)benzyl]-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-[5-chloro-2-(cyclobutyloxy)benzyl]-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-{5-chloro-2-[(2-methylprop-2-enyl)oxy]benzyl}-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-[5-chloro-2-(3-fluoro-2-methylpropoxy)benzyl]-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-[5-chloro-2-(2-fluoropropoxy)benzyl]-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-{[2-(fluoromethyl)prop-2-enyl]oxy}benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-sulfonic acid,

1-(5-chloro-2-((2,4-difluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-sulfonic acid,

1-(2-((4-chloro-2-fluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-sulfonic acid,

N-((1-(5-chloro-2-((2,4-difluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinolin-5-yl)sulfonyl)acetamide,

N-((1-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)-1,2,3,4-tetrahydroquinolin-5-yl)sulfonyl)acetamide,

1-(5-chloro-2-(cyclopentyloxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-(propooxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(2-(4-chloro-2-fluorobenzyloxy)-5-methylbenzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

1-(5-chloro-2-(neopentyloxy)benzyl)-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

4-(2-(4-chloro-2-fluorobenzyloxy)-5-methylbenzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-fluoro-2-isobutoxybenzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-chloro-2-isobutoxybenzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-chloro-2-cyclobutoxybenzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-chloro-2-(cyclopropylmethoxy)benzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

4-(5-chloro-2-(neopentyloxy)benzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

1-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylic acid,

8-{5-chloro-2-[(2,4-difluorobenzyl)oxy]benzyl}-5,6,7,8-tetrahydro-1,8-naphthyridine-4-carboxylic acid,

8-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-5,6,7,8-tetrahydro-1,8-naphthyridine-4-carboxylic acid,

1-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-1,2,3,4-tetrahydro-1,7-naphthyridine-5-carboxylic acid,

1-{5-chloro-2-[(2,4-difluorobenzyl)oxy]benzyl}-1,2,3,4-tetrahydro-1,7-naphthyridine-5-carboxylic acid,

1-{5-chloro-2-[(2,4-difluorobenzyl)oxy]benzyl}-1,2,3,4-tetrahydro-1,6-naphthyridine-5-carboxylic acid,

1-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-1,2,3,4-tetrahydro-1,6-naphthyridine-5-carboxylic acid,

1-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-1,2,3,4-tetrahydroquinoxaline-5-carboxylic acid,

1-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-N-(methylsulfonyl)-1,2,3,4-tetrahydroquinoline-5-carboxamide,

1-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-N-[(dimethylamino)sulfonyl]-1,2,3,4-tetrahydroquinoline-5-carboxamide,

1-{5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl}-N-[(dimethylamino)sulfonyl]-1,2,3,4-tetrahydroquinoline-5-carboxamide,

N-({1-(5-chloro-2-[(4-chloro-2-fluorobenzyl)oxy]benzyl})-1,2,3,4-tetrahydroquinolin-5-yl]amino}carbonyl)methanesulfonamide,

4-(2-cyclobutoxy-5-fluorobenzyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid,

and the salts and prodrugs thereof.

15. A medicament comprising at least a compound according to claim 1 .

16. Pharmaceutical composition comprising at least one compound according to claim 1 and at least one pharmaceutically acceptable carrier, additive, adjuvant or vehicle.