Metabolically stable prodrugs

US12397058B2 · kind B2 · utility

Assignees

• TSRL, Inc. · US
• THE REGENTS OF THE UNIVERSITY OF MICHIGAN · US

Inventors

• Elke Lipka · Ann Arbor, US
• Eric Simon · Princeton, US
• Andy D. White · Pinckney, US
• Kim Hutchings · Dexter, US
• Xinmin Gan · Ann Arbor, US

Key dates

• Filing date: Jun 26, 2019
• Grant date: Aug 26, 2025
• Expiry date: Nov 1, 2040

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D405/12
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Provided are prodrugs of various therapeutic agents that provide enhanced bioavailability of the therapeutic agent, and methods of treatment conditions in a subject by administration of the one or prodrugs. As provided herein a prodrug includes a therapeutic agent covalently attached to a cap, the cap having a structure according to formula (I) where: R1 is a branched or linear substituted or unsubstituted C2-C6 alkyl, alkenyl, or alkynl; X is —S(0)2-; R2 is a branched or linear substituted or unsubstituted C4-C20 alkyl, alkenyl, or alkynyl; and R3 is —H, C3-C5 cycloalkyl, C3-C5 cycloheteroalkyl, —C(CH3)3, —CF3, —C(CF3)3, or a substituted or unsubstituted phenyl.