Pyridin-4-yl derivatives
The invention relates to compounds of the Formula (I), Formula (I) wherein R 1 and R 2 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
1. A compound of Formula (I),
wherein
R 1 represents C 2-5 -alkyl or cyclopentyl; and
R 2 represents —OCH 2 —CH(OH)—CH 2 —NHCO—CH 2 OH;
or a salt thereof.
2. A compound according to claim 1 , wherein R 1 represents ethyl, n-propyl, isopropyl, n-butyl, isobutyl, isopentyl, pent-3-yl, or cyclopentyl, or a salt thereof.
3. A compound according to claim 1 , wherein R 1 represents n-propyl, isopropyl, isobutyl, or cyclopentyl, or a salt thereof.
4. A compound according to claim 1 , wherein R 1 represents cyclopentyl, or a salt thereof.
5. A compound according to claim 1 , wherein the stereocenter of the
R 2 group —OCH 2 —CH(OH)—CH 2 —NHCO—CH 2 OH is in the S-configuration, or a salt thereof.
6. A compound according to claim 1 selected from the group consisting of:
(S)—N-(3-(2-ethyl-4-(5-(2-ethylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methyl-phenoxy)-2-hydroxypropyl)-2-hydroxyacetamide;
(S)—N-(3-(2-ethyl-4-(5-(2-propylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methyl-phenoxy)-2-hydroxypropyl)-2-hydroxyacetamide;
(S)—N-(3-(2-ethyl-4-(5-(2-isopropylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide;
(S)—N-(3-(2-ethyl-4-(5-(2-butylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide;
(S)—N-(3-(2-ethyl-4-(5-(2-isobutylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide;
(S)—N-(3-(2-ethyl-4-(5-(2-isopentylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide;
(S)—N-(3-(2-ethyl-4-(5-(2-(pentan-3-yl)-pyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide; and
(S)—N-(3-(2-ethyl-4-(5-(2-cyclopentylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxypropyl)-2-hydroxyacetamide;
or a salt of any such compound.
7. A compound according to claim 1 which is (S)—N-(3-(2-ethyl-4-(5-(2-cyclopentylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)-2-hydroxyproplyl)-2-hydroxyacetamide or a salt thereof.
8. A pharmaceutical composition comprising
a compound according to claim 1 , in free or pharmaceutically acceptable salt form, and
a pharmaceutically acceptable carrier.
9. A compound according to claim 1 which is (S)—N-(3-(2-ethyl-4-(5-(2-ethylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methyl-phenoxy)-2-hydroxypropyl)-2-hydroxyacetamide or a salt thereof.
10. A pharmaceutical composition comprising
a compound according to claim 7 , in free or pharmaceutically acceptable salt form, and
a pharmaceutically acceptable carrier.
11. A pharmaceutical composition comprising
a compound according to claim 9 , in free or pharmaceutically acceptable salt form, and
a pharmaceutically acceptable carrier.