IP Library Granted Patent US 8,592,456
Granted Patent B2
US 8,592,456 · App. 13/360,050 · Granted Nov 26, 2013

IL17 and IFN-gamma inhibition for the treatment of autoimmune inflammation

Inventors: Johann Leban (Planegg-Martinsried, DE); Stefan Tasler (Seefeld, DE); Roland Baumgartner (Planegg-Martinsried, DE); Wael Saeb (Planegg-Martinsried, DE); Carine Chevrier (Munich, DE)
Assignee: 4SC Discovery GmbH
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Quick Facts
Patent No.
US 8,592,456
App. No.
13/360,050
Granted
Nov 26, 2013
Kind
B2
Abstract

The present invention relates to compounds of the general formula (I), and the pharmaceutically acceptable salt or solvate thereof, as anti-inflammatory and immunomodulatory agents.

Claims (135)

1. A compound of formula (I)

or a pharmaceutically acceptable salt or solvate thereof,

wherein

R 1 is aryl, heteroaryl, cycloalkyl, heterocyclyl or alkyl, which is optionally substituted by one or more substituents R′, and which R 1 is not piperidinyl;

Ar is aryl, cycloalkyl, heterocyclyl or heteroaryl, which is optionally substituted by one or more substituents R′;

Z is H, halogen, —CR″O, —N(R″) 2 , —CN, —C(S)R″, —N═C(R′) 2 , —CO 2 R″, —NR′CO 2 R″, —CONHR″, —CON(R″) 2 , —COSR″, —CSNHR″, —CSN(R″) 2 , —SO 2 -alkyl, —SO 2 -haloalkyl, —SO 2 NHR″, —SO 2 (NR″) 2 , amino or —SO 2 R″;

Y is H, halogen, haloalkyl, or alkyl, which is optionally substituted by one or more substituents R′;

R′ each independently represents H, —CO 2 R″, —CONHR″, —CR″O, —SO 2 N(R″) 2 , —SO 2 NHR″, —NR″—CO-haloalkyl, —NO 2 , —NR″—SO 2 -haloalkyl, —NR″—SO 2 -alkyl, —SO 2 -alkyl, —NR″—CO-alkyl, —CN, alkyl, cycloalkyl, aminoalkyl, alkylamino, alkoxy, —OH, —SH, alkylthio, hydroxyalkyl, hydroxyalkylamino, halogen, haloalkyl, haloalkoxy, amino, heterocyclyl, aryl, haloaryl, haloarylalkyl, arylalkyl or heteroaryl; and

R″ each independently represents H, haloalkyl, hydroxyalkyl, amino, alkoxy, —N═C(R′) 2 , —NR′—CO—R′, —CR′O, —CO 2 R′, alkyl, cycloalkyl, aryl, haloaryl, haloarylalkyl, heteroaryl, heterocyclyl, arylalkyl or aminoalkyl, which are optionally substituted by one or more substituents R′;

wherein R 1 , Ar, Z and Y may not comprise more than three coupled substituents R′ and/or R″.

2. A compound according to claim 1 , wherein

Ar is aryl or heteroaryl, which is optionally substituted by one or more substituents R′.

3. A compound according to claim 1 , wherein

R 1 is aryl or heteroaryl which is optionally substituted by one or more substituents R′; and

Ar is aryl or heteroaryl, which is optionally substituted by one or more substituents R′.

4. A compound according to claim 1 , wherein

R 1 is aryl, which is optionally substituted by one or more substituents R′

Ar is aryl or heteroaryl, which is optionally substituted by one or more substituents R′; and

Z is H, halogen, —CR″O, —N(R″) 2 , —CN, —C(S)R″, —N═C(R′) 2 , —CO 2 R″, —NR′CO 2 R″, —CONHR″, —CON(R″) 2 , —COSR″, —CSNHR″, —CSN(R″) 2 , amino, which is optionally substituted by one or more substituents R′.

5. A compound according to claim 1 , wherein

R 1 is aryl or heteroaryl, which is optionally substituted by one or more substituents R′;

Ar is aryl or heteroaryl, which is optionally substituted by one or more substituents R′;

Z is H, halogen, —CR″O, —N(R″) 2 , —CN, —C(S)R″, —N═C(R′) 2 , —CO 2 R″, —NR′CO 2 R″, —CONHR″, —CON(R″) 2 , —COSR″, —CSNHR″, —CSN(R″) 2 , amino, which is optionally substituted by one or more substituents R′; and

R′ each independently represents H, —CO 2 R″, —SO 2 N(R″) 2 , —SO 2 NHR″, —CN, alkyl, alkoxy, —OH, hydroxyalkyl, halogen, haloalkyl, haloalkoxy, heterocyclyl, aryl, haloaryl, haloarylalkyl, arylalkyl or heteroaryl.

6. A compound according to claim 1 , wherein

R 1 is aryl, or heteroaryl, which is optionally substituted by one or more substituents R′;

Ar is aryl or heteroaryl, which is optionally substituted by one or more substituents R′;

Z is H, halogen, —CR″O, —C(S)R′, —CO 2 R″, —NR′CO 2 R″, —CONHR″, —CON(R″) 2 , —COSR″, —CSNHR″, —CSN(R″) 2 , which is optionally substituted by one or more substituents R′;

Y is H, halogen, haloalkyl, or alkyl, which is optionally substituted by one or more substituents R′;

R′ each independently represents H, —CO 2 R″, —CONHR″, —CR″O, —SO 2 N(R″) 2 , —SO 2 NHR″, —CN, alkyl, alkoxy, —OH, halogen, haloalkyl or haloalkoxy; and

R″ each independently represents H, haloalkyl, or alkyl, which is optionally substituted by one or more substituents R′.

7. A compound according to claim 1 , wherein

R 1 is aryl, which is optionally substituted by one or more substituents R′;

Ar is aryl, which is optionally substituted by one or more substituents R′;

Z is H, haloalkyl, aryl, heteroaryl, CO 2 R″, —CONHR″, —CR″O, —CON(R″) 2 , COSR″, which is optionally substituted by one or more substituents R′;

Y is H, halogen, haloalkyl, or alkyl, which is optionally substituted by one or more substituents R′;

R′ each independently represents H, —CO 2 R″, —CONHR″, —CR″O, —CN, alkyl, alkoxy, —OH, halogen, haloalkyl or haloalkoxy; and

R″ each independently represents H, haloalkyl, or alkyl, which is optionally substituted by one or more substituents R′.

8. A compound according to claim 1 , wherein

R′ each independently represents H, —NO 2 , —SO 2 -alkyl, —CN, alkyl, cycloalkyl, aminoalkyl, alkylamino, alkoxy, —OH, —SH, alkylthio, hydroxyalkyl, hydroxyalkylamino, halogen, haloalkyl, haloalkoxy, amino, heterocyclyl, aryl, haloaryl, haloarylalkyl, arylalkyl or heteroaryl; and

R″ each independently represents H, haloalkyl, hydroxyalkyl, amino, alkoxy, —N═C(R′) 2 , —NR′—CO—R′, —CR′O, —CO 2 R′, alkyl, cycloalkyl, aryl, haloaryl, haloarylalkyl, heteroaryl, heterocyclyl, arylalkyl or aminoalkyl, which are optionally substituted by one or more substituents R′.

9. A compound according to claim 1 , wherein

R′ each independently represents H, —CO 2 R″, —CONHR″, —CR″O, —SO 2 N(R″) 2 , —SO 2 NHR″, —NR″—CO-haloalkyl, —NO 2 , —NR″—SO 2 -haloalkyl, —NR″—SO 2 -alkyl, —SO 2 -alkyl, —NR″—CO-alkyl, —CN, alkyl, cycloalkyl, aminoalkyl, alkylamino, alkoxy, —OH, —SH, alkylthio, hydroxyalkyl, hydroxyalkylamino, halogen, haloalkyl, haloalkoxy, amino, heterocyclyl, aryl, haloaryl, haloarylalkyl, arylalkyl or heteroaryl; and

R″ each independently represents H, haloalkyl, hydroxyalkyl, amino, alkoxy, alkyl, cycloalkyl, aryl, haloaryl, haloarylalkyl, heteroaryl, heterocyclyl, arylalkyl or aminoalkyl.

10. A compound according to claim 1 , wherein

R′ each independently represents H, —NO 2 , —SO 2 -alkyl, —CN, alkyl, cycloalkyl, aminoalkyl, alkylamino, alkoxy, —OH, —SH, alkylthio, hydroxyalkyl, hydroxyalkylamino, halogen, haloalkyl, haloalkoxy, amino, heterocyclyl, aryl, haloaryl, haloarylalkyl, arylalkyl or heteroaryl; and

R″ each independently represents H, haloalkyl, hydroxyalkyl, amino, alkoxy, alkyl, cycloalkyl, aryl, haloaryl, haloarylalkyl, heteroaryl, heterocyclyl, arylalkyl or aminoalkyl.

11. A compound according to claim 1 , wherein

R 1 is aryl, heteroaryl, cycloalkyl, heterocyclyl or alkyl, which is optionally substituted by one or more substituents R′, and when R 1 is a heterocycle, it is a 3- to 8-membered non-aromatic heterocyclic group which contains at least one heteroatom selected from O and S.

12. A compound of formula (I)

or a pharmaceutically acceptable salt or solvate thereof,

wherein

R 1 is aryl, heteroaryl, cycloalkyl, heterocyclyl or alkyl, which is optionally substituted by one or more substituents R′

Ar is aryl, cycloalkyl, heterocyclyl or heteroaryl, which is optionally substituted by one or more substituents R′;

Z is H, halogen, —CR″O, —N(R″) 2 , —CN, —C(S)R″, —N═C(R′) 2 , —CO 2 R″, —NR′CO 2 R″, —CONHR″, —CON(R″) 2 , —COSR″, —CSNHR″, —CSN(R″) 2 , —SO 2 -alkyl, —SO 2 -haloalkyl, —SO 2 NHR″, —SO 2 (NR″) 2 , amino or —SO 2 R″;

Y is alkylester, which is optionally substituted by one or more substituents R′;

R′ each independently represents H, —CO 2 R″, —CONHR″, —CR″O, —SO 2 N(R″) 2 , —SO 2 NHR″, —NR″—CO-haloalkyl, —NO 2 , —NR″—SO 2 -haloalkyl, —NR″—SO 2 -alkyl, —SO 2 -alkyl, —NR″—CO-alkyl, —CN, alkyl, cycloalkyl, aminoalkyl, alkylamino, alkoxy, —OH, —SH, alkylthio, hydroxyalkyl, hydroxyalkylamino, halogen, haloalkyl, haloalkoxy, amino, heterocyclyl, aryl, haloaryl, haloarylalkyl, arylalkyl or heteroaryl; and

R″ each independently represents H, haloalkyl, hydroxyalkyl, amino, alkoxy, —N═C(R′) 2 , —NR′—CO—R′, —CR′O, —CO 2 R′, alkyl, cycloalkyl, aryl, haloaryl, haloarylalkyl, heteroaryl, heterocyclyl, arylalkyl or aminoalkyl, which are optionally substituted by one or more substituents R′;

wherein R 1 , Ar, Z and Y may not comprise more than three coupled substituents R′ and/or R″.

13. A compound according to claim 12 , wherein Y is —C(O)OC 2 H 5 .

14. A compound, which is one of the following compounds:

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(ethoxycarbonyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-cyanophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-(methoxycarbonyl)thiophen-3-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

(3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazol-4-yl)(piperidin-1-yl)methanone;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-isobutyl-5-(trifluoromethyl)-1H-pyrazol-4-carboxylate;

3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-N-methylisoxazole-4-carboxamide;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

isopropyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-phenyl-5-(trifluoromethyl)1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3,5-difluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-N-methylisoxazole-4-carboxamide;

3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-N-methoxy-N-methylisoxazole-4-carboxamide;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2,2,2-trifluoroethyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 3-(2-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2-chlorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 3-(2,6-dichlorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

3-(2,6-dichlorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-N-methylisoxazole-4-carboxamide;

ethyl 3-(2,4-dichlorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

(3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazol-4-yl)(isoxazolidin-2-yl)methanone;

S-methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carbothioate;

S-methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carbothioate;

S-methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carbothioate;

(3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazol-4-yl)(isoxazolidin-2-yl)methanone;

(Z)-methyl N-(3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazol-4-yl)-2,2,2-trifluoroacetimidate;

4-bromo-3-(2-chloro-6-fluorophenyl)-5-(1-(3-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole;

4-bromo-3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole;

4-bromo-3-(2-chloro-6-fluorophenyl)-5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole;

ethyl 3-(3-fluoropyridin-4-yl)-5-(1-(pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 5-(1-(3-acetamidophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(3-fluoropyridin-4-yl)isoxazole-4-carboxylate;

ethyl 3-(3,5-dichloropyridin-4-yl)-5-(1-(2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 5-(1-(3-acetamidophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(3,5-dichloropyridin-4-yl)isoxazole-4-carboxylate;

ethyl 3-(3,5-dichloropyridin-4-yl)-5-(1-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 5-(1-(2-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(3-fluoropyridin-4-yl)isoxazole-4-carboxylate;

isopropyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-cyanophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-isoxazole-4-carboxylate;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-isoxazole-4-carboxylate;

ethyl 3-(2-chlorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-isoxazole-4-carboxylate;

ethyl 5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2,6-dichlorophenyl)-isoxazole-4-carboxylate;

ethyl 5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-fluorophenyl)isoxazole-4-carboxylate;

isopropyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

(3-(2-chlorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazol-4-yl)(isoxazolidin-2-yl)methanone;

3-(2-chlorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-N-methoxy-N-methylisoxazole-4-carboxamide;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

S-methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-3-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carbothioate;

methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 5-(1-(3-acetamidophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-chloro-6-fluorophenyl)isoxazole-4-carboxylate;

methyl 3-(2-chlorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2,6-dichlorophenyl)isoxazole-4-carboxylate;

methyl 5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2,4-dichlorophenyl)isoxazole-4-carboxylate;

methyl 5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-fluorophenyl)isoxazole-4-carboxylate;

isopropyl 5-(1-(3-acetamidophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-chloro-6-fluorophenyl)isoxazole-4-carboxylate;

isopropyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 5-(1-(3-acetamidophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-chloro-6-fluorophenyl)isoxazole-4-carboxylate;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-(3-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

methyl 5-(1-(3-aminophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-chloro-6-fluorophenyl)isoxazole-4-carboxylate;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-(2-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate;

ethyl 3-(2-chloro-6-fluorophenyl)-5-(1-((tetrahydrofuran-2-yl)methyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylate; and

ethyl 5-(1-(2-aminophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-3-(2-chloro-6-fluorophenyl)isoxazole-4-carboxylate;

or a pharmaceutically acceptable salts or solvate thereof.

15. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

16. A compound according to claim 14 , or a pharmaceutically acceptable salt thereof.

17. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

18. A pharmaceutical composition comprising a compound according to claim 14 and a pharmaceutically acceptable carrier.

19. A method for treating psoriasis, psoriatric arthritis, autoimmune thyroiditis, Grave's disease, rheumatoid arthritis, vitiligo, Crohn's disease, ulcerative colitis, inflammatory bowel disease, ankylosing spondylitis, diabetes type I, multiple sclerosis, celiac disease, systemic lupus erythematosus, uveitis, Behcet disease, atopic dermatitis, Lichen planus, Sjögren's syndrome, spinal disc herniation, acne, Graft-versus-Host-Reaction, Host-versus-Graft-Reaction or osteoarthritis, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 .

20. A method for treating psoriasis, psoriatric arthritis, autoimmune thyroiditis, Grave's disease, rheumatoid arthritis, vitiligo, Crohn's disease, ulcerative colitis, inflammatory bowel disease, ankylosing spondylitis, diabetes type I, multiple sclerosis, celiac disease, systemic lupus erythematosus, uveitis, Behcet disease, atopic dermatitis, Lichen planus, Sjögren's syndrome, spinal disc herniation, acne, Graft-versus-Host-Reaction, Host-versus-Graft-Reaction or osteoarthritis, comprising administering to a subject in need thereof an effective amount of a compound according to claim 14 .

Assignments (4)
CHANGE OF ADDRESS Recorded Jul 2, 2021
From: IMMUNIC AG
To: IMMUNIC AG
Reel/Frame 057304/0526 →
MERGER Recorded Mar 19, 2021
From: 4SC DISCOVERY GMBH
To: 4SC AG
Reel/Frame 055661/0943 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2021
From: 4SC AG
To: IMMUNIC AG
Reel/Frame 055662/0100 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2012
From: LEBAN, JOHANN; TASLER, STEFAN; BAUMGARTNER, ROLAND; SAEB, WAEL; CHEVRIER, CARINE
To: 4SC DISCOVERY GMBH
Reel/Frame 028012/0808 →
Priority Claims (1)
EP 11152515 · Jan 28, 2011 · regional
Continuity (2)
Provisional Application 61437061 · Jan 28, 2011
Related Publication 20120196861A1 · Aug 2, 2012