Pyridin-2-yl derivatives as immunomodulating agents

1. A compound of the Formula (I),

wherein

A represents

wherein the asterisks indicate the bond that is linked to the pyridine group of Formula (I);

R 1 represents methyl, ethyl or methoxy; R 2 represents hydrogen; and R 3 represents C 2-5 -alkyl or C 1-4 -alkoxy; or

R 1 represents C 2-5 -alkyl or C 1-4 -alkoxy; R 2 represents hydrogen; and R 3 represents methyl or ethyl; or

R 1 represents methyl, ethyl, or methoxy; R 2 represents C 3-5 -alkyl; and R 3 represents hydrogen;

R 4 represents hydrogen or methoxy;

R 5 represents hydrogen, C 1-3 -alkyl, or methoxy;

R 6 represents —CH 2 —(CH 2 ) n —CONR 61 R 62 , hydroxy, hydroxy-C 2-4 -alkoxy, di-(hydroxy-C 1-2 -alkyl)-C 1-2 -alkoxy, 2,3-dihydroxy-propoxy, —OCH 2 —(CH 2 ) n —NR 61 R 62 , —OCH 2 —CH(OH)—CH 2 —NR 6 R 6 , —OCH 2 —(CH 2 ) n —NHSO 2 R 63 , —OCH 2 —CH(OH)—CH 2 —NHSO 2 R 63 , —OCH 2 —(CH 2 ) n —NHCOR 64 , or —OCH 2 —CH(OH)—CH 2 —NHCOR 64 ;

R 61 represents hydrogen, methyl, ethyl, 2-hydroxyethyl, carboxymethyl, 1-(C 1-5 -alkylcarboxy)methyl, 2-carboxyethyl, 2-(C 1-5 -alkylcarboxy)ethyl, 2-aminoethyl, or 2-methylamino-ethyl;

R 62 represents hydrogen, or methyl;

R 63 represents C 1-3 -alkyl, methylamino, ethylamino, or dimethylamino;

R 64 represents hydroxymethyl, 2-hydroxyethyl, aminomethyl, methylaminomethyl, 2-aminoethyl, or 2-methylamino-ethyl;

n represents the integer 1, or 2; and

R 7 represents hydrogen, methyl or chloro;

or a salt thereof.

2. The compound according to claim 1 , wherein A represents

wherein the asterisks indicate the bond that is linked to the pyridine group of Formula (I);

or a salt thereof.

3. The compound according to claim 1 , wherein A represents

wherein the asterisk indicates the bond that is linked to the pyridine group of Formula (I);

or a salt thereof.

4. The compound according to claim 1 , wherein R 1 represents methyl or methoxy, R 2 represents hydrogen, and R 3 represents C 2-4 -alkyl or C 1-3 -alkoxy; or a salt thereof.

5. The compound according to claim 1 , wherein R 1 represents C 2-4 -alkyl or C 1-3 -alkoxy, R 2 represents hydrogen, and R 3 represents methyl; or a salt thereof.

6. The compound according to claim 1 , wherein R 1 represents methyl, R 2 represents C 4 -alkyl, and R 3 represents hydrogen; or a salt thereof.

7. The compound according to claim 1 , wherein at least one of R 4 , R 5 and R 7 represents a group other than hydrogen; or a salt thereof.

8. The compound according to claim 1 , wherein R 4 represents methoxy, and R 5 and R 7 represent hydrogen; or a salt thereof.

9. The compound according to claim 1 , wherein R 4 represents hydrogen, R 5 represents C 1-3 -alkyl or methoxy, and R 7 represents methyl or chloro; or a salt thereof.

10. The compound according to claim 1 , wherein R 6 represents —CH 2 —(CH 2 ) n —CONR 61 R 62 , di-(hydroxy-C 1-2 -alkyl)-C 1-2 -alkoxy, 2,3-dihydroxy-propoxy, —OCH 2 —(CH 2 ) n —NR 61 R 62 , —OCH 2 —CH(OH)—CH 2 —NR 61 R 62 , or —OCH 2 —CH(OH)—CH 2 —NHCOR 64 ;

or a salt thereof.

11. The compound according to claim 1 , wherein R 6 represents 2,3-dihydroxy-propoxy, or —OCH 2 —CH(OH)—CH 2 —NHCOR 64 ; or a salt thereof.

12. The compound according to claim 1 selected from the group consisting of:

N—((S)-3-{2-ethyl-4-[5-(6-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide;

N—((S)-3-{2-ethyl-4-[5-(4-isobutyl-6-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide;

2-hydroxy-N—((R)-2-hydroxy-3-{4-[5-(6-isobutyl-4-methoxy-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide;

2-hydroxy-N—((S)-2-hydroxy-3-{4-[5-(6-isobutyl-4-methoxy-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide;

N—((S)-3-{2-ethyl-4-[5-(6-isobutyl-4-methoxy-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide;

(S)-3-{4-[5-(6-isobutyl-4-methoxy-pyridin-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol;

(R)-3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diol;

(S)-3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diol;

N—((S)-3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide;

3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-N-(2-hydroxy-ethyl)-propionamide; and

3-(3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionylamino)-propionic acid;

or a salt of such a compound.

13. The compound according to claim 1 selected from the group consisting of:

2-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethylamine;

3-(2-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethylamino)-propionic acid;

N-(2-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethyl)-2-hydroxy-acetamide;

2-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,3-diol;

(S)-1-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-3-(2-hydroxy-ethylamino)-propan-2-ol;

ethanesulfonic acid ((S)-3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-amide;

3-((S)-3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propylamino)-propionic acid;

(S)-3-(2-ethyl-4-{5-[6-(1-ethyl-propyl)-4-methyl-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diol;

N—[(S)-3-(2-ethyl-4-{5-[6-(1-ethyl-propyl)-4-methyl-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide;

(S)-3-(2-Ethyl-4-{5-[6-(1-ethyl-propyl)-4-methoxy-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diol;

(S)-3-(2-chloro-4-{5-[6-(1-ethyl-propyl)-4-methoxy-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diol;

N—[(S)-3-(2-ethyl-4-{5-[6-(1-ethyl-propyl)-4-methoxy-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide;

N—[(S)-3-(4-{5-[6-(1-ethyl-propyl)-4-methoxy-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-2,6-dimethyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide;

N—[(S)-3-(2-chloro-4-{5-[6-(1-ethyl-propyl)-4-methoxy-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide;

N—[(S)-3-(4-{5-[6-(1-ethyl-propyl)-4-methoxy-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-2-methoxy-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide; and

N-((2S)-3-{2-ethyl-4-[3-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-5-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide;

or a salt of such a compound.

14. A pharmaceutical composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.