Morton-Norwich Products, Inc.

Norwich Eaton Pharmaceuticals, Inc.

Robert J Alaimo

Joseph E Gray

Ozra E Millner, Jr

Stanford S Pelosi, Jr

Marvin M Goldenberg

George M Klein

Jon A Andersen

Christopher J Hatton

James B Sheffer

Ronald J Storrin

The present invention involves compounds of the class of imidazo[4,5-f]quinolines and methods for enhancing the immune response system of mammals which comprises systemically administering to mammals having a depressed immune function an effective but nontoxic amount of a composition comprising such a compound.

Imidazo(4,5-f)quinolines useful as immunomodulating agents

New thiocyanatoquinoxaline compounds useful as immunomodulating agents which have the general formula: ##STR1## wherein R is hydrogen, methyl or 5-thiocyanato-2-furanyl; R.sub.1 is hydrogen, methyl or 2-furanyl; or R and R.sub.1 taken together completes a cyclohexyl ring.

Thiocyanatoquinoxaline compounds with immunomodulating activity

The compound 5-methyl-2-trifluoromethylindolo[2,3-b]quinoxaline is useful as an immunomodulating agent.

5-Methyl-2-trifluoromethylindolo[2,3-b]quinoxaline

The compound 6,7-dichloro-2-[(1-methyl-2-pyrrolidylidene)amino]-4-thiocyanatobenzothiaz ole is useful as an immunomodulating agent.

6,7-Dichloro-2-[(methy

Compounds of the formula: ##STR1## wherein R is 4-chlorophenyl, 3,4-dichlorophenyl, or 3,4-dimethoxyphenyl, and R.sub.1 is hydrogen or methylaminocarbonyl with the proviso that when R is 4-chlorophenyl, R.sub.1 is methylaminocarbonyl are useful as antifungal agents.

5-[(3,4-Dimethoxyphenyl)or(4-chlorophenyl)]-2-furancarboxa

The compound 5-(2,4-dichlorophenyl)-2-furancarboxaldehyde-O-[(methylamino)carbonyl]oxim e is useful as an antifungal agent.

5-(2,4-Dichlorophenyl)-3-furancarboxaldehyde-

The compound 5-[3,4-dimethoxyphenyl]-N-{[(methylamino)carbonyl]oxy}-.alpha.-oxo-2-furan ethanimidoyl chloride is useful as an antifungal agent.

Antifungal compound

8-[(4-Aminophenyl)sulfonyl] amino-2-napthalenyl phosphorodiamidate is useful as an inhibitor of the enzyme urease.

8-[(4-Aminophenyl)sulfonyl]amino-2-naphthalenyl phosphorodiamidate

[[(4-Aminophenyl)sulfonyl]amino]phenyl phosphorodiamidates are useful as inhibitors of the enzyme urease as well as being effective antimicrobial agents.

[[(4-Aminophenyl)sulfonyl]amino]phenyl phosphorodiamidates

3-[[(4-Aminophenyl)sulfonyl]amino]-N-[diaminophosphinyl]-benzamide is useful as an inhibitor of the enzyme urease as well as being an effective antimicrobial agent.

3-[[(4-Aminophenyl)sulfonyl]amino]-N-[diaminophosphinyl]-benzamide

Certain thiocyanatobenzothiazoles of the formula: ##STR1## wherein R is hydrogen, 4-bromo, 4-chloro, 4-fluoro, 3,4-dichloro or 4-nitro; R.sub.1 is methoxy or thiocyanato; R.sub.2 is n-butyl, chloro, methyl, or thiocyanato; and R.sub.3 is hydrogen or chloro are effective antibacterial agents.

Antibacterial thiocyanatobenzothiazoles

2-Bromo-1-hydroxyquinolizinium bromide substituted anilinium salts are useful as antiinflammatory agents.

2-Bromo-1-hydroxyquinolizinium bromide substituted anilinium salts

N-(6-ethyl-4-thiocyanato-2-benzothiazolyl)-5-nitrofuramide is an effective agent against coccidiosis in the chicken.

N-(6-Ethyl-4-thiocyanato-2-benzothiazolyl)-5-nitrofuramide

A series of 2-(3,4-dichlorophenyl)-4-(substituted amino)quinazolines of the formula: ##STR1## wherein R is (1-pyrrolidinyl)propyl; 3-[bis-(2-hydroxyethyl)amino]propyl; 2,3-dihydroxypropyl; 3-diethylamino-2-hydroxypropyl; or 3-hydroxypropyl and various acid salts are effective antibacterial agents.

2-(3,4-Dichlorophenyl)-4-(substituted amino)-quinazolines

2-(Substituted phenylimino)-2H-quinolizines are effective antiulcerogenic drugs.

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Norwich, NY, United States of America

Robert J Alaimo