Nicotinamide riboside analogs and pharmaceutical compositions and uses thereof

US10485814B2 · kind B2 · utility

Assignee

• GlaxoSmithKline Intellectual Property (No. 4) Limited · GB

Inventors

• Bruce Szczepankiewicz · Gages Lake, US
• Frank Preugschat · Morrisville, US
• Karsten Koppetsch · Woburn, US
• Robert B. Perni · Marlborough, US

Key dates

• Filing date: Jun 5, 2015
• Grant date: Nov 26, 2019
• Expiry date: Jun 5, 2035

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/048
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Provided herein are stereoisomerically pure ester and carbonate analogues of nicotinamide riboside and nicotinamide riboside hydride, and pharmaceutical compositions and uses thereof. The stereoisomerically pure ester and carbonate analogues of nicotinamide riboside and nicotinamide riboside hydride may be used to treat a disease or disorder that would benefit from increased NAD levels including a mitochondrial disease or disorder, insulin resistance, a metabolic syndrome, diabetes, obesity, for increasing insulin sensitivity in a subject, or to treat or prevent a skin condition.The compounds have general formulas (I) or (II): wherein R1 is —C(═O)—X—(C2-C18 straight chain or branched) alkyl or —C(═O)—X—(C2-C18 straight chain or branched) alkenyl; each R2 is independently selected from hydrogen, and a —C(O)—X—(C1-C18 straight chain or branched) alkyl or a —C(O)—X—(C2-C18 straight chain or branched) alkenyl; and X is a covalent bond or O.