1H-4(5)-substituted imidazole derivatives, their preparation and their use as histamine H3 receptor ligands

US6355665B1 · kind B1 · utility

Assignee

• The James Black Foundation Limited · GB

Inventors

• Matthew John Tozer · London, GB
• Sarkis Barret Kalindjian · Banstead, GB
• Ian Linney · London, GB
• Katherine Isabel Mary Steel · Sydenham, GB
• Michael John Pether · London, GB
• Tracey Cooke · St Albans, GB

Key dates

• Filing date: Mar 14, 2000
• Grant date: Mar 12, 2002
• Expiry date: Mar 14, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A compound of the formula wherein R2 is an optionally substituted Cz to Cg alkylene or alkylene chain; R3 is C2 to C15 optionally substituted hydrocarbyl; X is a bond or —NR4—, wherein R4 is hydrogen or non-aromatic C1 to C5 optionally substituted hydrocarbyl, or aryl(C1 to C3)alkyl, or a pharmaceutically acceptable salt thereof.A method of modifing histamine activity in a patient comprising administering to said patient a pharmaceutical composition containing an effective amount of a compound of formula wherein R1 is selected from C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 alkylthio, carboxy, carboxy(C1 to C6)alkyl, formyl, C1 to C6 alkylcarbonyl, C1 to C6 alkylcarbonylalkoxy, nitro, trihalomethyl, hydroxy, amino, C1 to C6 alkylcarbonylalkoxy, nitro, trihalomethyl, hydroxy, amino, C1 to C6 alkylamino, di(C1 to C6 alkyl)amino, aryl, C1 to C6 alkylaryl, halo, sulfamoyl and cyano; R2 is optionally substituted C2 to C20 hydrocarbylene, in which one or more hydrogen atoms may be replaced by halogen atoms and up to 6 carbon atoms may be replaced by oxygen or nitrogen atoms, R2 being in the form of an optionally substituted C2 to C8 alkylene or alkenylene chain; R3 is hydrogen…