Heteroaryl amines as glycogen synthase kinase 3β inhibitors (GSK3 inhibitors)

US7514445B2 · kind B2 · utility

Assignee

• Janssen Pharmaceutica NA · BE

Inventors

• Eddy Jean Edgard Freyne · Rumst, BE
• Peter Jacobus Johannes Antonius Buijnsters · Breda, NL
• Marc Willems · Beerse, BE
• Werner Constant Johan Embrechts · Beerse, BE
• Christopher John Love · Deurne, BE
• Paul Adriaan Jan Janssen · Vosselaar, BE
• Paulus Joannes Lewi · Turnhout, BE
• Jan Heeres · Vosselaar, BE
• Marc René de Jonge · Tilburg, NL
• Lucien Maria Henricus Koymans · Retie, BE
• Hendrik Maarten Vinkers · Ekeren, BE
• Koen Jeanne Alfons Van Aken · Kortrijk, BE
• Gaston Stanislas Marcella Diels · Turnhout, BE

Key dates

• Filing date: Oct 29, 2002
• Grant date: Apr 7, 2009
• Expiry date: May 20, 2024

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/12
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

This invention concerns a compound of formulaa N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine and a stereochemically isomeric form thereof, wherein ring A is a 6-membered heterocycle; R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; optionally substituted C1-6alkyl; C1-6alkyloxycarbonyl; optionally substituted C1-6alkyloxyC1-6alkylcarbonyl; X is a direct bond or a linker atom or group; Z is a direct bond or a linker atom or group; R2 is hydrogen, C1-10alkyl, C2-10alkenyl, C2-10alkynyl, a carbocycle or a heterocycle, each of said groups may optionally be substituted; R3 is hydrogen; hydroxy; halo; optionally substituted C1-6alkyl or C2-6alkenyl or C2-6alkynyl; C1-6alkyloxy; C1-6alkylthio; C1-6alkyloxycarbonyl; C1-6alkylcarbonyloxy; carboxyl; cyano; nitro; amino; mono- or di(C1-6alkyl)amino; polyhaloC1-6alkyl; polyhaloC1-6alkyloxy; polyhaloC1-6alkylthio; R21; R21—C1-6alkyl; R21—O—; R21—S—; R21—C(═O)—; R21—S(═O)p—; R7—S(═O)p—; R7—S(═O)p—NH—; R21—S(═O)p—NH—; R7—C(═O)—; —NHC(═O)H; —C(═O)NHNH2; R7—C(═O)—NH—; R21—C(═O)—NH—; —C(═NH)R7—C(═NH)R21; R4 is an optionally substituted heterocycle provided that —X—R2 and/or R3 is other than hydrogen; their use, pharmaceuti…