Westwood Pharmaceuticals, Inc.

Westwind Pharmaceuticals, Inc.

Edward J Luber, Jr

Paul L Warner, Jr

F Christopher Zusi

William A Somerville

6-Aminonicotinic acid is reacted with an alkali carbonate selected from the group consisting of sodium carbonate and potassium carbonate. The reaction is carried out at elevated temperature and in dimethylformamide. The 6-aminonicotinic acid alkali salt so produced is reacted with 3-chloromethylpyridine hydrochloride. The reaction is carried out at elevated temperature and in dimethylformamide. The desired nicotinyl ester is thus produced.

Process for the synthesis of the nicotinyl ester of 6-aminonicotinic acid

A 1-(2-acylaminophenyl)imidazole of formula: ##STR1## wherein R.sup.5 is a cycloaliphatic, phenyl, substituted phenyl group bonded to the carbonyl carbon through a carbon-to-carbon linkage are intermediates for the preparation of 4-substituted imidazo[1,2-a]quinoxalines having anti-inflammatory, immunosuppressant and anti-fungal activity.

1-(2-Acylaminophenyl)imidazoles

A method for treating inflammatory disorders in mammals which comprises administering to said mammals having an inflammatory disorder a therapeutically effective amount of 4-trifluoromethylimidazo[1,2-a]quinoxaline.

Treatment of inflammatory disorders with

2(1-imidazolyl)phenylureylene compounds of the formula: ##STR1## wherein R.sup.2 is hydrogen or a radical bonded to the nitrogen by a carbon to nitrogen linkage and selected from the group consisting of aliphatic, cycloaliphatic, phenyl, substituted phenyl, fused bicyclic aryl, and monocyclic aryl substituted aliphatic groups are intermediates for the preparation of 4-substituted amino imidazo[1,2-a]quinoxalines having immunosuppressant activity.

1-(2-Phenylureylene)imidazoles

A 4-substituted imidazo [1,2-a]quinoxaline of formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is bonded to a ring carbon through a carbon-to-carbon linkage and is an aliphatic, cycloaliphatic, substituted phenyl, fused bicyclic aryl; or a monocyclic aryl substituted aliphatic group.

4-Substituted imidazo [1,2-a]quinoxalines

Preparation of 4-substituted imidazo[1,2-a]quinoxalines by cyclizing a compound of the formula: ##STR1## with phosphorous oxychloride wherein X.sup.2 is a group --R.sup.5 or --NHR.sup.2 where R.sup.5 and R.sup.2 are hydrogen or various organo groups.

Process for preparing 4-substituted imidazo[1,2-a]quinoxalines

A 4-substituted imidazo[1,2-a]quinoxaline of formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sup.2 is hydrogen or a radical bonded to the nitrogen by a carbon to nitrogen linkage and selected from the group consisting of aliphatic, cycloaliphatic, phenyl, substituted phenyl, fused bicyclic aryl, and monocyclic aryl substituted aliphatic group.

4-Aminosubstituted imidazo(1,2-A)quinoxalines

A method for reducing the immunological response in mammals by the administration of certain substituted phenyl or substituted anilino imidazo[1,2-a]quinoxalines.

Method for reducing immunological response

A method for treating a fungal infection in mammals which comprises administering to said mammals having a fungal infection a therapeutically effective amount of a 4-(substituted phenyl)imidazo[1,2-a]quinoxaline.

Method for treating fungal infection in mammals with imidazo

A 1-(2-acylaminophenyl)imidazole of formula: ##STR1## wherein R.sup.5 is hydrogen or an aliphatic, cycloaliphatic, phenyl, substituted phenyl, fused bicyclic aryl or monocyclic aryl substituted aliphatic group bonded to the carbonyl carbon through a carbon-to-carbon linkage. The compounds are useful as intermediates in the preparation of 4-substituted imidazo[1,2-a]quinoxalines.

A 1-(2-acylaminophenyl)imidazole of formula: ##STR1## wherein R.sup.2 is hydrogen or a radical bonded to the nitrogen by a carbon to nitrogen linkage and selected from the group consisting of aliphatic, cycloaliphatic, phenyl, substituted phenyl, fused bicyclic aryl, and monocyclic aryl substituted aliphatic groups.

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Buffalo, NY, United States of America

Edward J Luber, Jr