US 12,291,519 B2
2-hydroxycycloalkane-1-carbamoyl
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. 17/634,512
Filed by Idorsia Pharmaceuticals Ltd, Allschwil (CH)
PCT Filed Aug. 14, 2020, PCT No. PCT/EP2020/072865
§ 371(c)(1), (2) Date Feb. 10, 2022,
PCT Pub. No. WO2021/028570, PCT Pub. Date Feb. 18, 2021.
Claims priority of application No. PCT/EP2019/071921 (WO), filed on Aug. 15, 2019.
Prior Publication US 2022/0324847 A1, Oct. 13, 2022
Int. Cl. C07H 19/12 (2006.01); C07D 405/04 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01)
CPC C07D 405/04 (2013.01) [C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01); C07H 19/12 (2013.01)] 16 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; trifluoromethoxy; and NRN11RN12 wherein RN11 represents hydrogen and RN12 represents hydroxy-C2-3-alkyl, or RN11 and RN12 together with the nitrogen atom to which they are attached form a 4- to 6-membered heterocyclyl selected from morpholin-4-yl, azetidine-1-yl, pyrrolidine-1-yl, and piperidine-1-yl, wherein said 4- to 6-membered heterocyclyl is unsubstituted or mono-substituted with hydroxy;
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—R1X wherein R1X represents
hydroxy;
morpholin-4-yl; or
NRN21RN22, wherein RN21 and RN22 together with the nitrogen atom to which they are attached form a 4- to 6-membered heterocyclyl selected from azetidine-1-yl, pyrrolidine-1-yl, and piperidine-1-yl, wherein said 4- to 6-membered heterocyclyl is mono-substituted with hydroxy;
L represents a direct bond, methylene, or ethylene; and
Ar2 represents
phenyl or 5- or 6-membered heteroaryl, wherein said phenyl or 5- or 6-membered heteroaryl independently is unsubstituted, or mono-, di- or tri-substituted; wherein the substituents independently are selected from C1-6-alkyl, C3-6-cycloalkyl, —CH2—C3-6-cycloalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy, C1-3-alkoxy, halogen, morpholine-4-yl, amino, ethynyl 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 independently are selected from methyl, methoxy, and halogen; or
naphthyl;
or a pharmaceutically acceptable salt thereof.