Pyridinyl sulfonamide derivatives, pharmaceutical compositions and uses thereof

1. A compound of formula (I)

wherein

ring A is selected from the group consisting of:

R 1 is selected from the group consisting of H, F, Cl, Br, CN, —OH, C 1-4 -alkyl, alkyl), —(CH 2 ) m —COOH, —(CH 2 ) m —C(═O)—O—(C 1-4 -alkyl), —C(═O)-heterocyclyl, —(CH 2 ) m —C(═O)—NH 2 , —(CH 2 ) m —C(═O)—NH—(C 1-4 -alkyl), —(CH 2 ) m —C(═O)—N(C 1-4 -alkyl) 2 , —C(═O)—NH—C 3-6 -cycloalkyl, —C(═O)—NH-heterocyclyl, —(CH 2 ) m —NH—C(═O)—(C 1-3 -alkyl), —N(C 1-3 -alkyl)-C(═O)—(C 1-4 -alkyl), —N(C 1-3 -alkyl)-C(═O)—NH 2 , —NH—C(═O)—NH—(C 1-4 -alkyl), heterocyclyl and phenyl,

wherein each alkyl group or sub-group is optionally substituted with 1 or more F atoms or with one OH or —O—(C 1-3 -alkyl) group; and

wherein each heterocyclyl is selected from the group consisting of azetidinyl, imidazolidinyl, piperidinylpiperidinyl, tetrahydropyranyl and morpholinyl, and each heterocycl is optionally substituted with one or two groups independently selected from the group consisting of oxo, C 1-3 -alkyl, —C(═O)—CH 3 and —C(═O)-cyclopropyl; and

wherein multiple R 1 may be identical or different, if n is 2; and

n is an integer selected from 1 and 2; and

m is an integer selected from 0, 1 and 2; and

wherein in any definition mentioned hereinbefore, if not specified otherwise, any alkyl group or sub-group may be straight-chained or branched and is optionally substituted with 1 or more F atoms,

or a salt thereof.

2. The compound of formula (I) according to claim 1 , wherein

R 1 is selected from the group consisting of:

H, F, Cl, —OH, —O—(C 1-2 -alkyl), —(CH 2 ) m —COOH, —(CH 2 ) m —C(═O)—O—(C 1-2 -alkyl), —C(═O)-heterocyclyl, —(CH 2 ) m —C(═O)—NH 2 , —(CH 2 ) m —C(═O)—NH—(C 1-4 -alkyl), —(CH 2 ) m —C(═O)—N(CH 3 )(C 1-3 -alkyl), —C(═O)—NH-cyclopropyl, —C(═O)—NH-heterocyclyl, —(CH 2 ) m —NH—C(═O)—(C 1-3 -alkyl), —N(C 1-2 -alkyl)-C(═O)—(C 1-2 -alkyl), —N(C 1-2 -alkyl)-C(═O)—NH 2 , —NH—C(═O)—NH—(C 1-2 -alkyl), heterocyclyl and phenyl,

wherein each alkyl group or sub-group is optionally substituted with 1 to 3 F atoms or with one OH or —O—(C 1-2 -alkyl) group; and

wherein each heterocyclyl is selected from the group consisting of azetidinyl, imidazolidinyl, piperidinylpiperidinyl, tetrahydropyranyl and morpholinyl, and each heterocyclyl is optionally substituted with one or two groups independently selected from the group consisting of oxo, —C(═O)—CH 3 and —C(═O)-cyclopropyl; and

wherein m is 0 or 1; and

wherein multiple R 1 may be identical or different, if n is 2;

or a salt thereof.

3. The compound of formula (I) according to claim 2 , wherein

R 1 is selected from the group consisting of:

H, F, —OH, —CH 3 , —CF 3 , —O—CH 3 , —COOH, —(CH 2 ) m —C(═O)—O—CH 3 , —(CH 2 ) m —C(═O)—NH 2 , —C(═O)—NH—(C 1-3 -alkyl), —(CH 2 )—C(═O)—N(CH 3 ) 2 , —(CH 2 )—C(═O)—N(CH 3 )(CH 2 CH 3 ), —C(═O)—NH-cyclopropyl, 1-(cyclopropylcarbonyl)-piperidin-4-yl and 3-methyl-2-oxo-imidazolidin-1-yl,

wherein each ethyl group or sub-group in said R 1 group is optionally substituted in position 2 with one F atom, one OH or one —O—CH 3 group; and

wherein each propyl group or sub-group in said R 1 group is optionally substituted in position 2 or 3 with 1 to 3 F atoms; and

wherein m is 0 or 1; and

wherein, if n is 2, multiple R 1 may be identical or different and the second R 1 group is selected from the group consisting of F, CH 3 , CF 3 and phenyl;

or a salt thereof.

4. The compound of formula (I) according to claim 1 , wherein

ring A is

R 1 is selected from the group consisting of H, F, —OH, C 1-4 -alkyl, —O—(C 1-4 -alkyl), —(CH 2 ) m —COOH, —(CH 2 ) m —C(═O)—O—(C 1-4 -alkyl), —C(═O)-heterocyclyl, —(CH 2 ) m —C(═O)—NH 2 , —(CH 2 ) m —C(═O)—NH—(C 1-4 -alkyl), —(CH 2 ) m —C(═O)—N(C 1-4 -alkyl) 2 , —C(═O)—NH—C 3-6 -cycloalkyl, —C(═O)—NH-heterocyclyl, —(CH 2 ) m —NH—C(═O)—(C 1-3 -alkyl), —N(C 1-3 -alkyl)-C(═O)—(C 1-4 -alkyl), —N(C 1-3 -alkyl)-C(═O)—NH 2 , —NH—C(═O)—NH—(C 1-4 -alkyl), heterocyclyl and phenyl,

wherein each alkyl group or sub-group is optionally substituted with 1 or more F atoms or with one OH or —O—(C 1-3 -alkyl) group; and

wherein each heterocyclyl is selected from the group consisting of azetidinyl, imidazolidinyl, piperidinyl, tetrahydropyranyl and morpholinyl, and each heterocyclyl is optionally substituted with one or two groups independently selected from the group consisting of oxo, C 1-3 -alkyl, —C(═O)—CH 3 and —C(═O)-cyclopropyl; and

wherein multiple R 1 may be identical or different, if n is 2; and

n is an integer selected from 1 and 2; and

m is an integer selected from 0 and 1; and

or a salt thereof.

5. The compound of formula (I) according to claim 4 , wherein

R 1 is selected from the group consisting of:

H, —OH, C 1-2 -alkyl, —O—(C 1-2 -alkyl), —(CH 2 ) m —COOH, —(CH 2 ) m —C(═O)—O—(C 1-2 -alkyl), —C(═O)-heterocyclyl, —(CH 2 ) m —C(═O)—NH 2 , —(CH 2 ) m —C(═O)—NH—(C 1-4 -alkyl), —(CH 2 ) m —C(═O)—N(C 1-2 -alkyl) 2 , —C(═O)—NH—C 3-6 -cyclopropyl, —C(═O)—NH-heterocyclyl, —(CH 2 ) m —NH—C(═O)—(C 1-3 -alkyl), —N(CH 3 )—C(═O)—(C 1-2 -alkyl), —N(CH 3 )—C(═O)—NH 2 , —NH—C(═O)—NH—(C 1-3 -alkyl), heterocyclyl and phenyl,

wherein each alkyl group or sub-group is optionally substituted with 1 to 3 F atoms or with one OH or —O—CH 3 group; and

wherein each heterocyclyl is selected from the group consisting of azetidinyl, imidazolidinyl, tetrahydropyranyl and morpholinyl, and each heterocyclyl is optionally substituted with one or two groups independently selected from the group consisting of oxo, C 1-3 -alkyl and —C(═O)—CH 3 ; and

wherein, if n is 2, multiple R 1 may be identical or different, the second R 1 group is selected from the group consisting of CH 3 , CF 3 and phenyl;

or a salt thereof.

6. The compound of formula (I) according to claim 1 , wherein

ring A is

R 1 is selected from the group consisting of H, F, Cl, —OH, —O—(C 1-4 -alkyl), —C(═O)-heterocyclyl, —(CH 2 ) m —C(═O)—NH 2 , —(CH 2 ) m —C(═O)—NH—(C 1-4 -alkyl), —(CH 2 ) m —C(═O)—N(C 1-4 -alkyl) 2 , —(CH 2 ) m —NH—C(═O)—(C 1-3 -alkyl) and —N(C 1-3 -alkyl)-C(═O)—(C 1-4 -alkyl),

wherein each alkyl group or sub-group is optionally substituted with 1 or more F atoms or with one OH or —O—(C 1-3 -alkyl) group; and

wherein each heterocyclyl is selected from the group consisting of azetidinyl, imidazolidinyl, piperidinyl, tetrahydropyranyl and morpholinyl, and each heterocyclyl is optionally substituted with one oxo or C 1-3 -alkyl group; and

wherein, if n is 2, multiple R 1 may be identical or different and the second R 1 group is F; and

n is an integer selected from 1 and 2; and

m is an integer selected from 0 and 1; and

or a salt thereof.

7. The compound of formula (I) according to claim 1 , wherein

ring A is

R 1 is selected from the group consisting of H, —(CH 2 ) m —COOH, —(CH 2 ) m —C(═O)—O—(C 1-4 -alkyl), —C(═O)-heterocyclyl, —(CH 2 ) m —C(═O)—NH 2 , —(CH 2 ) m —C(═O)—NH—(C 1-4 -alkyl) and —(CH 2 ) m —C(═O)—N(C 1-4 -alkyl) 2 ,

wherein each alkyl group or sub-group is optionally substituted with 1 or more F atoms or with one OH or —O—(C 1-3 -alkyl) group; and

wherein each heterocyclyl is selected from the group consisting of azetidinyl, imidazolidinyl, piperidinyl, tetrahydropyranyl and morpholinyl, and each heterocyclyl is optionally substituted with one oxo or C 1-3 -alkyl group; and

wherein multiple R 1 may be identical or different, if n is 2; and

n is 1; and

m is an integer selected from 0 and 1; and

or a salt thereof.

8. The compound of formula (I) according to claim 1 , wherein

ring A is

R 1 is selected from the group consisting of H, F, Cl, Br, CN, —OH, C 1-4 -alkyl, —O—(C 1-4 -alkyl), —C(═O)—NH 2 , —C(═O)—NH—(C 1-4 -alkyl), —C(═O)—N(C 1-4 -alkyl) 2 and heterocyclyl,

wherein each alkyl group or sub-group is optionally substituted with 1 or more F atoms or with one OH or —O—(C 1-3 -alkyl) group; and

wherein each heterocyclyl is selected from the group consisting of azetidinyl, and piperidinyl, and each heterocyclyl is optionally substituted with one C 1-3 -alkyl, —C(═O)—CH 3 or —C(═O)-cyclopropyl group; and

wherein, if n is 2, multiple R 1 may be identical or different and the second R 1 group is selected from the group consisting of F and CH 3 ; and

n is an integer selected from 1 and 2; and

or a salt thereof.

9. The compound of formula (I) according to claim 1 selected from the group consisting of:

or a salt thereof.

10. A pharmaceutically acceptable salt of a compound according to claim 1 .

11. A method for treating cancer, NASH (non-alcoholic steatohepatitis), pulmonary fibrosis, retinopathy, nephropathy or stroke, comprising administering a therapeutically effective amount of a compound according claim 1 , or a pharmaceutically acceptable salt thereof, to a patient in need thereof.

12. A pharmaceutical composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, optionally together with one or more inert carriers and/or diluents.

13. A method for treating a disease or condition which is mediated by inhibiting the activity of AOC3, comprising administering a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition comprising one or more compounds according to claim 1 , or a pharmaceutically acceptable salt thereof, and one or more additional therapeutic agents, optionally together with one or more inert carriers and/or diluents.

15. The compound of formula (I) according to claim 9 having the structure:

16. The compound of formula (I) according to claim 9 having the structure:

or a pharmaceutically acceptable salt thereof.

17. The compound of formula (I) according to claim 9 having the structure:

or a pharmaceutically acceptable salt thereof.

18. The compound of formula (I) according to claim 9 having the structure:

or a pharmaceutically acceptable salt thereof.

19. The compound of formula (I) according to claim 9 having the structure:

or a pharmaceutically acceptable salt thereof.

20. The compound of formula (I) according to claim 9 having the structure:

or a pharmaceutically acceptable salt thereof.

21. The compound of formula (I) according to claim 9 having the structure:

22. The compound of formula (I) according to claim 9 having the structure:

23. The compound of formula (I) according to claim 9 having the structure:

24. The compound of formula (I) according to claim 9 having the structure:

25. The compound of formula (I) according to claim 9 having the structure:

26. The compound of formula (I) according to claim 9 having the structure: