Merck + Co., Inc.

Peter Kulsa

Helmut H Mrozik

Richard J Bochis

Clarence S Rooney

Michael H Fisher

Dale R Hoff

Richard L Tolman

Edward F Rogers

Bruce O Linn

Imidazo pyridines with a carbamate group in the 2-position and a phenylthio, or phenylsulfinyl group in the 6-position are disclosed which also are substituted at the 3-position. The 3-position substituents may be halogen, substituted aminomethyl, acyl, and the like. The compounds are active anthelmintic agents. Compositions and methods for the use of such compounds against helmintic infections are also disclosed.

3-Substituted imidazo [1,2-A] pyridines

Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.

Certain 6-substituted-2-pyridinamines

Symmetrically substituted pyromellic diimides are disclosed wherein the compounds are substituted with a variety of substituent groups. The symmetrically substituted compounds are useful for administration to ruminant animals to increase feed efficiency, shift volatile fatty acid production in the ruminant from acetate with an increase in the more energetically efficient propionate and butyrate and to suppress methane formation in the rumen. Compositions and methods of treatment utilizing said compounds as the active ingredient thereof are also disclosed.

Symmetrically substituted pyromellitic diimides as ruminant feed

Derivatives of C-076, a series of macrolides, are described in which the substituents are acyl groups. The acyl substituents may be aromatic of non-aromatic. The acyl derivatives are prepared by various procedures depending upon the particular C-076 compound being substituted. The compounds thus produced have profound anthelmintic, insecticidal, ectoparasiticidal and acaracidal activity and compositions for such uses are also disclosed.

Acyl derivatives of C-076 compounds

Substituted imidazo [1,2-a] pyridines

Dihydroxybenzisoxazolin-3-yl-substituted-1-methyl-5-nitroimidazoles having the hydroxy- groups on adjacent 4,5-; 5,6- or 6,7-positions of the isoxazolin group. These compounds have antibacterial and antiprotozoal activity in humans and animals. They are particularly active against trypanosomiasis and trichomoniasis.

Dihydroxybenzisoxazolin-3-yl-substituted-5-nitroimidazoles as

Novel substituted benzoylacrylanilides are prepared by reacting a substituted benzoylacrylic acid with a substituted aniline in the presence of a coupling agent. These acrylanilides have significant anticoccidial activity.

Substituted benzoylacrylanilides

Certain substituted imidazo [1,2-a] pyridines

Novel substituted nitroimidazoles are provided, for example, 2-(4,5-substituted-isoxazol-3-yl)-1-substituted-5-nitroimidazole; 2-(4,5-disubstituted-.DELTA..sup.2 -isoxazolin-3-yl)-1-substituted-5-nitroimidazole; or 2-(4,5-disubstituted-2-loweralkyl-isoxazolidin-3-yl)-1-substituted-5-nitro imidazole. These compounds have antibacterial and antiprotozoal activity especially against human and animal trypanosomiasis and trichomoniasis.

Nitroimidazoles

Novel substituted nitroimidazoles are provided, for example, 2-(4,5-substituted-isoxazol-3-yl)-1-substituted-5-nitroimidazole; 2-(4,5-disubstituted-.DELTA..sup.2 -isoxazolin-3-yl)-1-substituted-5-nitroimidazole; or 2-(4,5-disubstituted-2-loweralkyl-isoxazolidin-3-yl)-1-substituted-5-nitro imidazole. These compounds have antibacterial and antiprotozoal activity, especially against human and animal trypanosomiasis and trichomoniasis.

Isoxazole substituted nitroimidazoles

4-Nitro-5-cyanoimidazoles substituted with a 1-loweralkyl group and variously substituted at the 2-position are useful as antiparasitic agents particularly as coccidiostats. The 4-nitro-5-cyanoimidazole coccidiostats are included in compositions useful for administration to poultry as treatment for coccidiosis.

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Plainfield, NJ, United States of America

Peter Kulsa