IP Library › Granted Patent US 12,240,814

Granted Patent B2

US 12,240,814 · App. 18/493,017 · Granted Mar 4, 2025

1-methyl-4-[(4-phenylphenyl)sulfonylmethyl]cyclohexyanol and 1-methyl-4-[[4-(2-pyridyl)phenyl]sulfonylmethyl]cyclohexanol compounds and their therapeutic use

Inventors: Lisa Patel (London, GB); Stephen Allan Smith (Bishops Stortford, GB)

Assignee: Istesso Therapeutics Limited

C07D213/61 C07C317/22 C07C317/36 C07D213/06

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 12,240,814
App. No.: 18/493,017
Granted: Mar 4, 2025
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain substituted 1-methyl-4-[(4-phenylphenyl)sulfonylmethyl]cyclohexanol and 1-methyl-4-[[4-(2-pyridyl)phenyl]sulfonylmethyl]cyclohexanol compounds (collectively referred to herein as CHMSA compounds) that are useful, for example, in the treatment of disorders (e.g., diseases) including, e.g., multiple myeloma, diffuse large B-cell lymphoma, acute myeloid leukemia, eosinophilic leukemia, glioblastoma, melanoma, ovarian cancer, chemotherapy resistant cancer, radiation resistant cancer, inflammatory arthritis, rheumatoid arthritis, psoriatic arthritis, psoriasis, ulcerative colitis, Crohn's disease, systemic lupus erythematosus (SLE), lupus nephritis, asthma, chronic obstructive pulmonary disease (COPD), non-alcoholic fatty liver disease (NAFLD), non-alcoholic steatohepatitis (NASH), autoimmune hepatitis, hidradenitis suppurativa, etc. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, for example, in therapy.

Claims (81)

1. A method of treating inflammatory arthritis in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a compound of the following formula:

or a pharmaceutically acceptable salt thereof,

wherein:

═X— is independently —CH═ or —N═;

—R 1 is independently —H or —R 1X ;

—R 1X is independently —F, —Cl, —R 1C , —R 1F , or —CN;

—R 1C is independently saturated linear or branched C 1-3 alkyl;

—R 1F is independently saturated linear or branched C 1-3 fluoroalkyl;

—R 2 is independently —H or —R 2X ;

—R 2X is independently —F, —Cl, —R 2C , —R 2F , or —CN;

—R 2C is independently saturated linear or branched C 1-3 alkyl;

—R 2F is independently saturated linear or branched C 1-3 fluoroalkyl;

—R 3 is independently —H or —R 3X ;

—R 3X is independently —F, —Cl, —R 3C , —R 3F , or —CN;

—R 3C is independently saturated linear or branched C 1-3 alkyl;

—R 3F is independently saturated linear or branched C 1-3 fluoroalkyl;

—R 4 is independently —H or —R 4X ;

—R 4X is independently —F, —Cl, —R 4C , —R 4F , or —CN;

—R 4C is independently saturated linear or branched C 1-3 alkyl;

—R 4F is independently saturated linear or branched C 1-3 fluoroalkyl;

—R 5 is independently —H or —R 5X ;

—R 5X is independently —F, —R 5C , or —R 5F ;

—R 5C is independently saturated linear or branched C 1-3 alkyl;

—R 5F is independently saturated linear or branched C 1-3 fluoroalkyl;

—R 6 is independently —H or —R 6X ;

—R 6X is independently —F, —R 6C , or —R 6F ;

R 6C is independently saturated linear or branched C 1-3 alkyl; and

—R 6F is independently saturated linear or branched C 1-3 fluoroalkyl;

or —R 5 and —R 6 , taken together with the carbon atom to which they are attached, form saturated C 3-6 cycloalkyl.

2. The method of claim 1 , wherein —R 5 is —H and —R 6 is —H.

3. The method of claim 2 , wherein ═X— is —CH═.

4. The method of claim 3 , wherein ═X— is —N═.

5. The method of claim 3 , wherein:

—R 1 is independently —H, —F, —Cl, or —CN; and

—R 2 is independently —H, —F, —Cl, or —CN.

6. The method of claim 4 , wherein:

—R 1 is independently —H, —F, —Cl, or —CN; and

—R 2 is independently —H, —F, —Cl, or —CN.

7. The method of claim 3 , wherein:

—R 3 is independently —H, —F, —Cl, or —CN; and

—R 4 is independently —H or —CF 3 .

8. The method of claim 4 , wherein:

—R 3 is independently —H, —F, —Cl, or —CN; and

—R 4 is independently —H or —CF 3 .

9. The method of claim 5 , wherein:

—R 3 is independently —H, —F, —Cl, or —CN; and

—R 4 is independently —H or —CF 3 .

10. The method of claim 6 , wherein:

—R 3 is independently —H, —F, —Cl, or —CN; and

—R 4 is independently —H or —CF 3 .

11. The method of claim 3 , wherein the compound is a compound of the following formula: