Prodrugs of urolithins and uses thereof

US10532992B2 · kind B2 · utility

Assignee

• Amazentis SA · CH

Inventors

• Christopher L. Rinsch · Morges, CH
• Rune Ringom

Key dates

• Filing date: Jun 11, 2018
• Grant date: Jan 14, 2020
• Expiry date: Jun 11, 2038

Classification

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

Abstract

The invention provides compounds of formula (I) or salts thereof: wherein: A, B, C, D, W, X, Y and Z are as defined in the specification, and at least one of A, B, C, D, W, X, Y and Z is OR1; each R1 being independently H or C(═O)R2, and at least one R1 group being C(═O)R2; where each R2 is selected from: CHR3NHR4, where R4 is H and R3 is a group selected from CH3, CH2CH(CH3)2, CH(CH3)CH2CH3, CH2Ph, CH2-3-(1H-indole), CH2CH2SCH3, CH2OH, CHOHCH3, CH2SH, CH2SeH and CH2PhpOH, wherein said R3 group can optionally be substituted by one or more groups selected from halogen, cyano, nitro, ORA or C1-C4 alkyl; or R3 and R4 together with the C and N atoms to which they are attached form a 5-membered heteroalkyl ring, wherein said heteroalkyl ring can optionally be substituted by one or more groups selected from halogen, cyano, nitro, ORA or C1-C3 alkyl, wherein RA is C1-C4 alkyl optionally substituted with one or more halogen, cyano or nitro groups. The compounds are effective pro-drugs for urolithins and they enable the ready delivery of urolithins to the site in the digestive tract where they can be absorbed into the body.