Phenyl derivatives containing an acidic group, their preparation and their use as chloride channel blockers

US6417393B1 · kind B1 · utility

Assignee

• Neurosearch A/S · DK

Inventors

• Palle Christophersen · Rang Taché Est, DK
• Ove Pedersen · Aabenraa, DK

Key dates

• Filing date: Jan 22, 1999
• Grant date: Jul 9, 2002
• Expiry date: Jan 22, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C335/22
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present patent application relates to compounds having formula (I) or a pharmaceutically acceptable salt thereof wherein one of R1, R2 and R3 is a non-cyclic acidic group having a pKa value below 8 or a group which is in vivo convertible to such a group; R4, R5 and the other two of the substituents R1, R2 and R3 are each independently selected from hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, alkoxy, hydroxy, halogen, trifluoromethyl, trifluoromethoxy, cyano, nitro, amnino, and aryl, aralkyl, arylamino, aryloxy, aryl—CO—, or heteroaryl, wherein the aryl and heteroaryl groups may be substituted one or more times with substituents selected from alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, hydroxy, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano, nitro and amino; or R3 and R4 or R4 and R5 together form a fused 4- to 7-membered carbocyclic ring which may be unsaturated, or partially or fully saturated, while the other substituents R1, R2, R3, R4 and R5 are as defined above; Y is —CO—, —CS—, —SO2—, or —C(═N—R8)—, wherein R8 is hydrogen, alkyl, or cyano; X is —NH—,…