Arylmethylazole preparation processes

US5023357A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Herbert Siegel · Hofheim, DE
• Klaus-Dieter Kampe · Bad Soden am Taunus, DE
• Hans G. Alpermann · Bocholt, DE
• Hermann Gerhards · Hofheim, DE
• Patricia Usinger · Eppstein, DE
• Ulrich Schacht · Hofheim, DE
• Margret Leven · Kelkheim, DE
• Wolfgang Raether
• Walter Dittmar · Hofheim, DE
• Burkhard Sachse · Kelkheim, DE

Key dates

• Filing date: Sep 21, 1989
• Grant date: Jun 11, 1991
• Expiry date: Sep 21, 2009

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D249/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Arylmethylazoles of the formula I ##STR1## in which Aryl is (substituted) phenyl or naphthyl; PA0 Z is CH or N; PA0 R.sup.1 and Q are H or alkyl; PA0 R.sup.2 is H, alk(en)yl or alkynyl; PA0 R.sup.3 l and R.sup.4 are H, alkyl or other hydrocarbons; or PA0 R.sup.3 and R.sup.4 together are a --(CH.sub.2).sub.2-11 chain or a bridged --(CH.sub.2).sub.4-5 chain, and their acid addition salts, stereoisomers and optically active enantiomers possess outstanding antimycotic and antidepressant activity. They are obtained, inter alia, from arylmethylazoles II ##STR2## which are reacted with a strong base and then with a carbonyl compound III 0=CR.sup.3 R.sup.4 ; thereafter, the product is reacted with the protic acid or with an alkyl halide IV R.sup.2 Hal. If desired, the products are converted to the acid addition salts, or the stereoisomers or optically active enantiomers are resolved.