US 12,312,362 B2
Spiro derivatives of Alpha-D-galactopyranosides
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. 18/248,007
Filed by Idorsia Pharmaceuticals Ltd, Allschwil (CH)
PCT Filed Oct. 5, 2021, PCT No. PCT/EP2021/077381
§ 371(c)(1), (2) Date Apr. 5, 2023,
PCT Pub. No. WO2022/073969, PCT Pub. Date Apr. 14, 2022.
Claims priority of application No. PCT/EP2020/077968 (WO), filed on Oct. 6, 2020.
Prior Publication US 2023/0295182 A1, Sep. 21, 2023
Int. Cl. C07H 19/12 (2006.01); C07D 413/14 (2006.01); C07D 498/10 (2006.01)
CPC C07D 498/10 (2013.01) [C07D 413/14 (2013.01); C07H 19/12 (2013.01)] 18 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
wherein
Ar1 represents
aryl which is unsubstituted, or 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;
C1-4-alkoxy;
—O—CO—C1-3-alkyl;
O—CO—NH—RN11 wherein RN11 represents hydrogen or C1-3-alkyl;
—O—CH2—C1-fluoroalkyl; or
—O—CH2—CO—R1X wherein R1X represents
hydroxy;
C1-3-alkoxy;
morpholin-4-yl; or
—NRN21RN22 wherein RN21 and RN22 both independently represent hydrogen or methyl; and

OG Complex Work Unit Chemistry
represents a spirocyclic fragment, wherein:
ring A represents a heterocycloalkylene selected from

OG Complex Work Unit Chemistry
wherein X represents nitrogen or oxygen, and n represents the integer 0 or 1; and wherein in case X represents nitrogen, said nitrogen is unsubstituted or mono-substituted with C1-4-alkyl;
and

OG Complex Work Unit Chemistry
wherein R2 represents hydrogen or C1-4-alkyl; and
ring B represents
C4-7-cycloalkane-diyl wherein said C4-7-cycloalkane-diyl is unsubstituted, mono-, or di-substituted wherein the substituents are independently selected from C1-4-alkyl; C1-3-fluoroalkyl; C1-4-alkoxy; halogen; cyano; oxo; hydroxy; hydroxy-C1-4-alkyl; hydroxyimino; morpholin-4-yl; and —NH—RN11 wherein RN11 represents C1-6-alkyl, C2-4-alkoxy, C3-6-cycloalkyl, C2-3-fluoroalkyl, —CO—C1-4-alkyl, or —CO—C1-4-alkoxy;
4- to 7-membered heterocycloalkane-diyl wherein said heterocycloalkane-diyl contains one ring oxygen atom;
4- to 7-membered heterocycloalkane-diyl wherein said heterocycloalkane-diyl contains one ring nitrogen atom, wherein said ring nitrogen atom is unsubstituted or mono-substituted with C1-4-alkyl, —CO—C1-4-alkyl, —SO2—C1-4-alkyl, —CO—C1-4-alkoxy, or —CO—NH—C1-4-alkyl; and wherein said 4- to 7-membered heterocycloalkane-diyl carries no further substituent in addition to said substituent on the ring nitrogen atom, or carries one further substituent on a ring carbon atom that is attached to said ring nitrogen atom wherein said substituent is oxo, or —CO—OH; or
bridged bicyclic C6-9-cycloalkane-diyl;
or a pharmaceutically acceptable salt thereof.