IP Library Patent Application 18704588
Patent Application
App. No. 18/704,588

CCR6 RECEPTOR MODULATORS

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Patent No.
US None
App. No.
18/704,588
Abstract

The present invention relates to compounds of Formula (I), their synthesis and use as CCR6 receptor modulators for the prevention or treatment of e.g. inflammatory/autoimmune diseases/disorders and cancer.

Claims (178)

1 . A compound of Formula (I)

wherein

Q represents N, CH, or C—R, wherein R represents halogen or C 1-3 -alkyl;

R 1 represents

C 1-3 -alkyl;

R 2 represents

hydrogen;

C 1-4 -alkyl;

hydroxy-C 1-3 -alkyl;

C 1-3 -fluoroalkyl; or

C 3-5 -cycloalkyl;

R 3a represents

halogen;

C 1-5 -alkyl;

C 1-3 -fluoroalkyl;

C 1-3 -fluoroalkoxy;

C 3-5 -cycloalkyl; or

1-(C 1-3 -fluoroalkyl)-C 3-5 -cycloalkyl;

R 3b represents

hydrogen; or

halogen;

R 4 represents

C 1-4 -alkyl which is unsubstituted; mono-substituted, wherein the substituent is selected from hydroxy or C 1-3 -alkyl-amino; or di-substituted, wherein the first substituent represents hydroxy, and the second substituent represents C 1 -fluoroalkyl; or

-L-Cy, wherein

-L- represents a direct bond or —CH 2 —; and

Cy represents C 3-7 -cycloalkyl optionally containing one ring heteroatom selected from nitrogen or oxygen; wherein Cy independently is unsubstituted; or

mono-substituted with

 hydroxy;

 oxo;

 C 1-4 -alkyl;

 -C(═O)R A , wherein R A represents C 1-3 -alkyl or hydroxy-C 1-3 -alkyl; or

 C 1-3 -alkyl-carbonyl-amino; or

di-substituted, wherein the first substituent represents oxo, and the second substituent represents C 1-3 -alkyl; or di-substituted, wherein the first substituent represents hydroxy and the second substituent represents C 1-3 -alkyl-carbonyl;

or Cy represents a saturated 5- to 8-membered bridged bicyclic hydrocarbon ring system, wherein Cy independently is mono-substituted, wherein the substituent is selected from

hydroxy-C 1-3 -alkyl; or

—C(═O)R B , wherein R B represents

 hydroxy;

 —NR N1 R N2 , wherein R N1 and R N2 independently represent hydrogen or C 1-3 -alkyl; or R N1 and R N2 together with the nitrogen atom to which they are attached form pyrrolidinyl; or

 C 1-3 -alkoxy;

or Cy represents a 5- or 6-membered heteroaryl containing one or two ring heteroatoms independently selected from nitrogen or oxygen; and

R 5 represents

C 1-4 -alkyl;

hydroxy-C 1-3 -alkyl;

C 1-3 -alkoxy-C 1-3 -alkyl;

C 3-7 -cycloalkyl;

C 1-3 -fluoroalkyl;

C 1-3 -alkyl-carbonyl; or

C 1-3 -alkyl-carbonyl-amino-C 1-3 -alkyl;

or R 4 and R 5 together with the triazolyl ring to which they are attached form 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl or 6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl;

or a pharmaceutically acceptable salt thereof.

2 . A compound according to claim 1 , wherein

Q represents CH;

R 1 represents

C 1-3 -alkyl;

R 2 represents

hydrogen;

C 1-4 -alkyl;

hydroxy-C 1-3 -alkyl; or

C 1-3 -fluoroalkyl;

R 3a represents

halogen;

C 1-5 -alkyl;

C 1-3 -fluoroalkyl;

C 1-3 -fluoroalkoxy;

C 3-5 -cycloalkyl; or

1-(C 1-3 -fluoroalkyl)-C 3-5 -cycloalkyl;

R 3b represents

hydrogen;

R 4 represents

C 1-4 -alkyl which is mono-substituted, wherein the substituent is selected from hydroxy or C 1-3 -alkyl-amino; or di-substituted, wherein the first substituent represents hydroxy, and the second substituent represents C 1 -fluoroalkyl; or

-L-Cy, wherein

-L- represents a direct bond or —CH 2 —; and

Cy represents C 3-7 -cycloalkyl optionally containing one ring heteroatom selected from nitrogen or oxygen, wherein Cy independently is unsubstituted; or

mono-substituted with

 hydroxy; or

 -C(═O)R A , wherein R A represents C 1-3 -alkyl;

or Cy represents a saturated 5- to 8-membered bridged bicyclic hydrocarbon ring system, wherein Cy independently is mono-substituted, wherein the substituent is selected from

hydroxy-C 1-3 -alkyl; or

—C(═O)R B , wherein R B represents

 hydroxy; or

 C 1-3 -alkoxy;

or Cy represents a 6-membered heteroaryl containing one ring nitrogen atom; and

R 5 represents

C 1-4 -alkyl;

hydroxy-C 1-3 -alkyl;

C 3-7 -cycloalkyl; or

C 1-3 -fluoroalkyl;

or a pharmaceutically acceptable salt thereof.

3 . A compound according to claim 1 , wherein R 3a represents C 1-5 -alkyl or C 1-3 -fluoroalkyl; or a pharmaceutically acceptable salt thereof.

4 . A compound according to claim 1 , wherein R 2 represents C 1-4 -alkyl or hydroxy-C 1-3 -alkyl; or a pharmaceutically acceptable salt thereof.

5 . A compound according to claim 1 , wherein R 4 represents

C 1-4 -alkyl which is mono-substituted with hydroxy; or di-substituted, wherein the first substituent represents hydroxy, and the second substituent represents C 1 -fluoroalkyl; or

-L-Cy, wherein

-L- represents a direct bond; and

Cy represents C 3-7 -cycloalkyl optionally containing one ring heteroatom selected from nitrogen or oxygen; wherein Cy independently is unsubstituted; or

mono-substituted with

hydroxy; or

—C(═O)R A , wherein R A represents C 1-3 -alkyl;

or Cy represents bicyclo[1.1.1]pentan-1-yl or bicyclo[2.2.2]octan-1-yl, wherein Cy independently is mono-substituted, wherein the substituent is selected from

hydroxy-C 1-3 -alkyl; or

—C(═O)R B , wherein R B represents

hydroxy; or

C 1-3 -alkoxy;

or Cy represents pyridinyl;

or a pharmaceutically acceptable salt thereof.

6 . A compound according to claim 1 , wherein R 5 represents C 1-4 -alkyl or C 3-7 -cycloalkyl; or a pharmaceutically acceptable salt thereof.

7 . A compound according to claim 1 , wherein

a) the radical

 represents 3-methyl-azetidine-3-yl, 1,3-dimethyl-azetidine-3-yl, 1-isopropyl-3-methyl-azetidine-3-yl, 1-(2-hydroxyethyl)-3-methyl-azetidine-3-yl, or 1-(2,2-difluoroethyl)-3-methyl-azetidine-3-yl;

b) the radical

 represents 4-bromo-phenyl, 4-ethyl-phenyl, 4-(n-propyl)-phenyl, 4-isopropyl-phenyl, 4-tert-butyl-phenyl, 4-cyclopropyl-phenyl, 4-(2,2,2-trifluoroethyl)-phenyl, 4-trifluoromethoxy-phenyl, or 4-(1-trifluoromethyl-cyclopropyl)-phenyl;

c) the radical

 represents 5-(1-cyclopropyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(4-hydroxy-cyclohexyl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(1-hydroxy-1-trifluoromethyl-ethyl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(4-methoxycarbonyl-bicyclo[2.2.2]octan-1-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(1-methyl-1-methylamino-ethyl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(1-hydroxy-cyclobutyl-methyl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(4-carboxy-bicyclo[2.2.2]octan-1-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclohexyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-methyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-(2-hydroxyethyl)-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-ethyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-isopropyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopentyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-tert-butyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-(2,2-difluoropropyl)-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclobutyl-5-tetrahydropyran-4-yl-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(pyridin-3-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(1-hydroxy-1-methyl-ethyl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-isopropyl-5-(1-hydroxy-1-methyl-ethyl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(3-(hydroxymethyl)-bicyclo[1.1.1]pentan-1-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-isopropyl-5-(3-(hydroxymethyl)-bicyclo[1.1.1]pentan-1-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(4-hydroxy-tetrahydropyran-4-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-isopropyl-5-(4-hydroxy-tetrahydropyran-4-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-cyclopropyl-5-(N-acetyl-piperidin-4-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, 5-(1-isopropyl-5-(N-acetyl-piperidin-4-yl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl, or 5-(1-cyclopropyl-5-(1-hydroxy-1-methyl-ethyl)-1H-1,2,4-triazol-3-yl)-pyridin-3-yl;

or a pharmaceutically acceptable salt thereof.

8 . A compound according to claim 1 , wherein the asymmetric carbon atom bearing the hydroxy group has the absolute configuration depicted in Formula (II)

or a pharmaceutically acceptable salt thereof.

9 . A compound according to claim 1 , which is

(R)-(4-Bromo-phenyl)-{5-[1-cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-methanol;

(R)-(4-tert-Butyl-phenyl)-{5-[1-cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-methanol;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-[4-(1-trifluoromethyl-cyclopropyl)-phenyl]-methanol;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-trifluoromethoxy-phenyl)-methanol;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-[4-(2,2,2-trifluoro-ethyl)-phenyl]-methanol;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-ethyl-phenyl)-methanol;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-propyl-phenyl)-methanol;

trans-4-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-cyclohexanol;

(R)-2-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-1,1,1-trifluoro-propan-2-ol;

4-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester;

(R)-{5-[1-Cyclopropyl-5-(1-methyl-1-methylamino-ethyl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

1-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-ylmethyl)-cyclobutanol;

4-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-bicyclo[2.2.2]octane-1-carboxylic acid;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-{5-[1-Cyclohexyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-(1,3-Dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-{5-[1-methyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-methanol;

2-[3-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-5-(tetrahydro-pyran-4-yl)-[1,2,4]triazol-1-yl]-ethanol;

(R)-(1,3-Dimethyl-azetidin-3-yl)-{5-[1-ethyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(4-isopropyl-phenyl)-methanol;

(R)-(1,3-Dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-{5-[1-isopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-methanol;

(R)-{5-[1-Cyclopentyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-{5-[1-tert-Butyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-{5-[1-(2,2-Difluoro-propyl)-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-{5-[1-Cyclobutyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-[5-(1-Cyclopropyl-5-pyridin-3-yl-1H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-(4-Cyclopropyl-phenyl)-{5-[1-cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-methanol;

2-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-propan-2-ol;

2-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-propan-2-ol;

(R)-{5-[1-Cyclopropyl-5-(3-hydroxymethyl-bicyclo[1.1.1]pent-1-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-(1,3-Dimethyl-azetidin-3-yl)-{5-[5-(3-hydroxymethyl-bicyclo[1.1.1]pent-1-yl)-1-isopropyl-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(4-isopropyl-phenyl)-methanol;

4-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-tetrahydro-pyran-4-ol;

4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-tetrahydro-pyran-4-ol;

1-[4-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-piperidin-1-yl]-ethanone;

1-[4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-piperidin-1-yl]-ethanone;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1-isopropyl-3-methyl-azetidin-3-yl)-(4-isopropyl-phenyl)-methanol;

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-[1-(2,2-difluoro-ethyl)-3-methyl-azetidin-3-yl]-(4-isopropyl-phenyl)-methanol;

2-{3-[(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-hydroxy-(4-isopropyl-phenyl)-methyl]-3-methyl-azetidin-1-yl}-ethanol; or

2-(2-Cyclopropyl-5-{5-[(R)-hydroxy-(4-isopropyl-phenyl)-(3-methyl-azetidin-3-yl)-methyl]-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-propan-2-ol;

or a pharmaceutically acceptable salt thereof.

10 . A compound according to claim 1 , which is

(R)-{5-[1-Cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(1,3-dimethyl-azetidin-3-yl)-(3-fluoro-4-isopropyl-phenyl)-methanol;

4-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-2-fluoro-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-trans-cyclohexanol;

4-(2-Cyclopropyl-5-{5-[(R)-(1,3-dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-2-methyl-pyridin-3-yl}-2H-[1,2,4]triazol-3-yl)-trans-cyclohexanol;

(R)-(1,3-Dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-[5-(1-isopropyl-5-propyl-1H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-methanol;

4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-1-methyl-piperidin-2-one;

N-[4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-trans-cyclohexyl]-acetamide;

1-[4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-piperidin-1-yl]-2-hydroxy-ethanone;

4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-4-methyl-piperidin-2-one;

4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-piperidin-2-one;

1-[4-(5-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-2-isopropyl-2H-[1,2,4]triazol-3-yl)-4-hydroxy-piperidin-1-yl]-ethanone;

(R)-(1,3-Dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-{5-[1-(2-methoxy-ethyl)-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-methanol;

(R)-(1-Cyclopropyl-3-methyl-azetidin-3-yl)-{5-[1-cyclopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-(4-isopropyl-phenyl)-methanol;

N-{2-[3-{5-[(R)-(1,3-Dimethyl-azetidin-3-yl)-hydroxy-(4-isopropyl-phenyl)-methyl]-pyridin-3-yl}-5-(tetrahydro-pyran-4-yl)-[1,2,4]triazol-1-yl]-ethyl}-acetamide; or

(R)-(1,3-Dimethyl-azetidin-3-yl)-(4-isopropyl-phenyl)-{6-[1-isopropyl-5-(tetrahydro-pyran-4-yl)-1H-[1,2,4]triazol-3-yl]-pyridazin-4-yl}-methanol;

or a pharmaceutically acceptable salt thereof.

11 . A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt thereof and further comprising at least one pharmaceutically acceptable carrier.

12 - 14 . (canceled)

15 . A method for the prevention or treatment of inflammatory/autoimmune diseases, conditions, or disorders; or cancer, said method comprising administering to a subject in need of said prevention or treatment a pharmaceutically active amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

16 . A pharmaceutical composition comprising a compound according to claim 9 or a pharmaceutically acceptable salt thereof and further comprising at least one pharmaceutically acceptable carrier.

17 . A pharmaceutical composition comprising a compound or a pharmaceutically acceptable salt thereof according to claim 10 and further comprising at least one pharmaceutically acceptable carrier.

18 . A method for the prevention or treatment of inflammatory/autoimmune diseases, conditions, or disorders; or cancer, said method comprising administering to a subject in need of said prevention or treatment a pharmaceutically active amount of a compound according to claim 9 or a pharmaceutically acceptable salt thereof.

19 . A method for the prevention or treatment of inflammatory/autoimmune diseases, conditions, or disorders; or cancer, said method comprising administering to a subject in need of said prevention or treatment a pharmaceutically active amount of a compound according to claim 10 or a pharmaceutically acceptable salt thereof.

Assignments (2)
PATENT SECURITY AGREEMENT Recorded Jun 25, 2026
From: IDORSIA PHARMACEUTICALS LTD
To: BIOPHARMA CREDIT PLC, AS COLLATERAL AGENT
Reel/Frame 076038/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 25, 2024
From: ALLEMANN, OLIVER; CAROFF, EVA; HUBLER, FRANCIS; MEYER, EMMANUEL
To: IDORSIA PHARMACEUTICALS LTD
Reel/Frame 067223/0159 →