Phenol derivatives, pharmaceutical compositions containing these compounds and processes for the preparation of these compounds and compositions

US4959391A · kind A · utility

Assignee

• Gruenenthal GmbH · DE

Inventors

• Oswald Zimmer · Würselen, DE
• Werner Vollenberg · Stolberg, DE
• Gerriet K. H. Loschen · Stolberg, DE
• Werner Winter · Aachen, DE
• Erwin Kiesewetter · Stolberg, DE
• Ulrich G. P. Seippl · Aachen, DE

Key dates

• Filing date: Jul 14, 1988
• Grant date: Sep 25, 1990
• Expiry date: Jul 14, 2008

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F9/5428
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.5 into another carboxylic acid derivative. By hydrogenation A and B may be varied within the scope of the definition.