4-aryl-thiazole derivatives

US5254575A · kind A · utility

Assignee

• Akzo N.V. · NL

Inventors

• John H. Pick · Lesmahagow, GB
• Robert T. Logan · Lanark, GB

Key dates

• Filing date: Mar 25, 1992
• Grant date: Oct 19, 1993
• Expiry date: Mar 25, 2012

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D233/90
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The invention concerns a 4-aryl-thiazole or imidazole derivative having the formula I ##STR1## wherein X is 0 or NOH, PA0 Y is S or NR.sub.3, PA0 Ar is a group selected from phenyl, naphthyl, tetrahydronaphthyl, and biphenyl, PA0 R is one to four substituents independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower thioalkyl, cycloalkyl, halogen, CF.sub.3, NO.sub.2, and O-ALK-NR.sub.1 R.sub.2, in which ALK is a saturated aliphatic hydrocarbon group having 2-6 carbon atoms, and R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl, or form, together with the nitrogen atom to which they are bonded, a heterocyclic ring, and PA0 R.sub.3 is hydrogen or a lower alkyl; or a pharmaceutically acceptable salt thereof, with the proviso that 4-(4-chlorophenyl)-thiazole-2-carboxamide is excluded. The compounds according to the invention increase the sensitivity of cardiac myofibrils to calcium and possess phosphodiesterase inhibitory activity and bronchodilator activity, and are useful for the treatment of patients suffering from heart failure and asthma.