US 12,291,520 B2
Galectin-3 inhibiting 2-hydroxycycloalkane-1-carbamoyl derivatives
Martin Bolli, Allschwil (CH); John Gatfield, Allschwil (CH); Corinna Grisostomi, Allschwil (CH); Lubos Remen, Allschwil (CH); Christoph Sager, Allschwil (CH); and Cornelia Zumbrunn, Allschwil (CH)
Assigned to IDORSIA PHARMACEUTICALS LTD, Allschwil (CH)
Appl. No. 18/251,273
Filed by Idorsia Pharmaceuticals Ltd, Allschwil (CH)
PCT Filed Nov. 1, 2021, PCT No. PCT/EP2021/080276
§ 371(c)(1), (2) Date May 1, 2023,
PCT Pub. No. WO2022/090544, PCT Pub. Date May 5, 2022.
Claims priority of application No. PCT/EP2020/080681 (WO), filed on Nov. 2, 2020; and application No. PCT/EP2021/053133 (WO), filed on Feb. 10, 2021.
Prior Publication US 2023/0348442 A1, Nov. 2, 2023
Int. Cl. C07H 19/12 (2006.01); C07D 405/04 (2006.01)
CPC C07D 405/04 (2013.01) [C07H 19/12 (2013.01)] 20 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein
n represents the integer 1 or 2;
Ar1 represents
aryl which is mono-, di-, tri-, tetra-, or penta-substituted, wherein the substituents are independently selected from halogen; methyl; cyano; methoxy; trifluoromethyl; and trifluoromethoxy;
5- or 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl independently is unsubstituted, mono-or di-substituted, wherein the substituents are independently selected from halogen, methyl, cyano, and methoxy; or
9- or 10-membered heteroaryl, wherein said 9- or 10-membered heteroaryl independently is unsubstituted, or mono-substituted with methyl;
R1 represents
hydroxy;
C1-3-alkoxy;
—O—CO—C1-3-alkyl;
—O—CH2—CH2—OH; or
—O—CH2—CO—OH;
L represents a direct bond or methylene; and
Ar2 represents
phenyl, wherein said phenyl is unsubstituted, mono-, di-or tri-substituted wherein the substituents are independently selected from C1-6-alkyl, C3-6-cycloalkyl, —CH2-C3-6-cycloalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy, C1-3-alkoxy, halogen, and cyano;
5- or 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl independently is unsubstituted, mono-, di-, or tri-substituted wherein the substituents are independently selected from C1-6-alkyl, C3-6-cycloalkyl, —CH2-C3-6-cycloalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy, C1-3-alkoxy, halogen, and cyano;
9-membered bicyclic heteroaryl or 10-membered bicyclic heteroaryl, wherein said 9- or 10-membered bicyclic heteroaryl independently is unsubstituted, mono-or di-substituted, wherein the substituents are independently selected from methyl, methoxy, and halogen; or
naphthyl;
or a pharmaceutically acceptable salt thereof.