US 11,834,414 B2
1-methyl-4-[(4-phenylphenyl)sulfonylmethyl]cyclohexyanol and 1-methyl-4-[[4-(2-pyridyl)phenyl]sulfonylmethyl]cyclohexanol compounds and their therapeutic use
Lisa Patel, London (GB); and Stephen Allan Smith, Bishops Stortford (GB)
Assigned to Modern Biosciences Limited, London (GB)
Appl. No. 17/265,929
Filed by Modern Biosciences Limited, London (GB)
PCT Filed Aug. 15, 2019, PCT No. PCT/EP2019/071917
§ 371(c)(1), (2) Date Feb. 4, 2021,
PCT Pub. No. WO2020/035560, PCT Pub. Date Feb. 20, 2020.
Claims priority of application No. 1813312 (GB), filed on Aug. 15, 2018.
Prior Publication US 2022/0363642 A1, Nov. 17, 2022
Int. Cl. C07C 317/22 (2006.01); C07D 213/06 (2006.01); C07C 317/36 (2006.01)
CPC C07D 213/06 (2013.01) [C07C 317/22 (2013.01); C07C 317/36 (2013.01)] 22 Claims
 
1. A compound of the following formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof;
wherein:
═X— is independently —CH═ or —N═;
—R1 is independently —H or —R1X;
—R1X is independently —F, —Cl, —R1C, —R1F For —CN;
—R1C is independently saturated linear or branched C1-3alkyl;
—R1F is independently saturated linear or branched C1-3fluoroalkyl;
—R2 is independently —H or —R3X;
—R2X is independently —F, —Cl, —R2C, —R2F, or —CN;
—R2C is independently saturated linear or branched C1-3alkyl;
—R2F is independently saturated linear or branched C1-3fluoroalkyl;
—R3 is independently —H or —R3X;
—R3X is independently —F, —Cl, —R3C, —R3F, or —CN;
—R3C is independently saturated linear or branched C1-3alkyl;
—R3F is independently saturated linear or branched C1-3fluoroalkyl;
—R4 is independently —H or —R4X;
—R4X is independently —F, —Cl, —R4C, —R4F, or —CN;
—R4C is independently saturated linear or branched C1-3alkyl;
—R4F is independently saturated linear or branched C1-3fluoroalkyl;
—R5 is independently —H or —R5X;
—R5X is independently —F, —R5C, or —R5F;
—R5C is independently saturated linear or branched C1-3alkyl;
—R5F is independently saturated linear or branched C1-3fluoroalkyl;
—R6 is independently —H or —R6X;
—R6X is independently —F, —R6C, or —R6F;
—R6C is independently saturated linear or branched C1-3alkyl; and
—R6F is independently saturated linear or branched C1-3fluoroalkyl;
or —R5 and —R6, taken together with the carbon atom to which they are attached, form saturated C3-6cycloalkyl.