Naphth[1,2-d]imidazoles

US4461894A · kind A · utility

Assignee

• Gruppo Lepetit S.p.A. · IT

Inventors

• Amedeo Omodei-Sale · Voghera, IT
• Emilio Toia · Milano, IT

Key dates

• Filing date: Apr 26, 1982
• Grant date: Jul 24, 1984
• Expiry date: Apr 26, 2002

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D263/60
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Naphth[1,2-d]imidazoles and naphth[2,1-d]oxazoles of formula ##STR1## wherein R and R.sub.1 are hydrogen, halogen, alkyl or alkoxy, R.sub.2 is hydrogen or halogen and A is one of the following moieties ##STR2## wherein R.sub.3 is alkyl, cycloalkyl, or a --(CH.sub.2).sub.n NR.sub.5 R.sub.6 group in which n is 1, 2 or 3, R.sub.5 is hydrogen or alkyl, R.sub.6 is alkyl or R.sub.5 and R.sub.6 taken together with the adjacent nitrogen atom are a 4- to 7-membered saturated hetero ring which may contain a further hetero atom and optionally may be substituted, e.g., with phenyl or substituted phenyl, R.sub.4 is hydrogen, alkyl, cycloalkyl or a --(CH.sub.2).sub.n NR.sub.5 R.sub.6 group, provided that one of R.sub.3 and R.sub.4 is a --(CH.sub.2).sub.n --NR.sub.5 R.sub.6 group, and R.sub.7 is --(CH.sub.2).sub.n --NR.sub.5 R.sub.6, or a pharmaceutically-acceptable acid addition salt thereof. They are made by contacting a corresponding naphth[1,2-d]imidazole or a naphth[2,1-d]oxazole wherein one of R.sub.3 and R.sub.4 or R.sub.7 is a --(CH.sub.2).sub.n X group wherein X is the residue of a reactive ester with an appropriate amine of the formula HNR.sub.5 R.sub.6 in the presence of an acid accept…