Prodrug of 1,1′-(1,6-dioxo-1,6-hexanediyl)bis-D-proline

US9737505B2 · kind B2 · utility

Assignee

• GlaxoSmithKline Intellectual Property Development Limited · GB

Inventors

• Alexis Denis · Paris, FR
• Olivier Mirguet · Les Ulis, FR
• Jérôme Toum · Les Ulis, FR

Key dates

• Filing date: Oct 28, 2015
• Grant date: Aug 22, 2017
• Expiry date: Oct 28, 2035

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D405/14
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The compound (2R,2′R)-bis(((((tetrahydro-2H-pyran-4-yl)oxy)carbonyl)oxy)methyl) 1,1′-adipoylbis(pyrrolidine-2-carboxylate) possesses physicochemical properties suitable for pharmaceutical development and is capable of generating (R)-1-[6-[(R)-2-carboxy-pyrrolidin-1-yl]-6-oxo-hexanoyl]pyrrolidine-2-carboxylic acid (CPHPC) in quantities capable of depleting serum amyloid P component (SAP) efficiently following oral administration, making it useful in the treatment of amyloidosis, Alzheimer's disease, type 2 diabetes mellitus and osteoarthritis.