US 12,404,295 B2
(Hetero)aryl-methyl-thio-beta-D-galactopyranoside derivatives
Martin Bolli, Allschwil (CH); Daniel Bur, Therwil (CH); John Gatfield, Allschwil (CH); Corinna Grisostomi, Allschwil (CH); Lubos Remen, Allschwil (CH); and Cornelia Zumbrunn, Allschwil (CH)
Assigned to IDORSIA PHARMACEUTICALS LTD, Allschwil (CH)
Appl. No. 17/633,895
Filed by Idorsia Pharmaceuticals Ltd, Allschwil (CH)
PCT Filed Aug. 7, 2020, PCT No. PCT/EP2020/072238
§ 371(c)(1), (2) Date Feb. 8, 2022,
PCT Pub. No. WO2021/028336, PCT Pub. Date Feb. 18, 2021.
Claims priority of application No. PCT/EP2019/071416 (WO), filed on Aug. 9, 2019.
Prior Publication US 2022/0315619 A1, Oct. 6, 2022
Int. Cl. C07H 19/056 (2006.01)
CPC C07H 19/056 (2013.01) 15 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
wherein
Ar1 represents
aryl which is mono-, di-, tri-, tetra-, or penta-substituted, wherein the substituents are independently selected from halogen, methyl, cyano, and methoxy; or
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;
Ar2 represents
phenyl or 5- or 6-membered heteroaryl, wherein said phenyl or 5- or 6-membered heteroaryl independently is unsubstituted, mono-, di-, or tri-substituted wherein the substituents independently are C1-6-alkyl, C3-6-cycloalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy, halogen, hydroxy-C1-3-alkyl, or phenyl; or
naphthyl;
R1a represents hydrogen; and R1b represents
—C2-4-alkyl; or
—C0-1-alkylene-Ar1b, wherein Ar1b represents phenyl or 5- or 6-membered heteroaryl, wherein said phenyl or 5- or 6-membered heteroaryl independently is unsubstituted, mono- or di-substituted with methyl;
or R1a and R1b both represent hydrogen, methyl, ethyl, or n-propyl;
or R1a and R1b together with the carbon atom to which they are attached form a 3- to 6-membered ring selected from
C3-6-cycloalkylene, wherein said C3-6-cycloalkylene independently is unsubstituted, mono-, or di-substituted, wherein the substituents independently are methyl or fluoro;
tetrahydro-2H-pyran-4,4-diyl, which is unsubstituted, di-, or tetra-substituted with methyl;
tetrahydro-2H-thiopyran-1,1-dioxide-4,4-diyl; or
piperidine-4,4-diyl, pyrrolidine-3,3-diyl, or azetidine-3,3-diyl wherein the nitrogen of said piperidine, pyrrolidine or azetidine independently is unsubstituted, or substituted with —C1-3-alkyl, —C0-2-alkylene-C3-6-cycloalkyl, or -L-RN1 wherein
-L- represents —CO—, —SO2—, *—CO—NH—, *—CO—O—, or *—SO2—NH—, and
RN1 represents —C1-3-alkyl or —C0-2-alkylene-C3-6-cycloalkyl;
wherein in the above groups the asterisks indicate the bond which is connected to the rest of the molecule; or
R1a and R1b together with the carbon atom to which they are attached form a spiro-bicyclic ring system of the structure (S1AB)

OG Complex Work Unit Chemistry
 wherein ring (A) represents a 3- to 6-membered non-aromatic carbocyclic ring, wherein said 3- to 6-membered non-aromatic carbocyclic ring optionally contains one ring oxygen atom and wherein said 3- to 6-membered non-aromatic carbocyclic ring is unsubstituted or di-substituted with fluoro; and
R2 represents hydroxy or C1-3-alkoxy;
or a pharmaceutically acceptable salt thereof.