Eli Lilly and Company

Wayne A Spitzer

Theodore Goodson, Jr

Frantz Victor

Shawn Christopher Miller

Mark Joseph Tebbe

Louis Nickolaus Jungheim

Joseph Chiou-Chung Tang

Joseph Matthew Colacino

Thomas R Sattelberg, Sr

Beverly Ann Heinz

Charles J Paget, Jr

Stjepan P Kukolja

Brent Jeffrey Rieder

Douglas O Spry

David A Hall

Chafiq Hamdouchi

Richard E Holmes

Ian G Wright

Steven R Lammert

Joseph Michael Gruber

Chyun-Yeh Earnest Wu

Marie T Reamer

Jesus Ezquerra-Carrera

Michael S Vannieuwenhze

Kurt D Schladetzky

Anti-viral compounds

A series of benzimidazole compounds having the following general structure are provided which inhibit the growth of picornaviruses (e.g., rhinoviruses, enteroviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus) and flaviviruses (e.g., hepatitis C and bovine diarrheal virus). ##STR1## A method for inhibiting picornaviruses and flaviviruses is also provided which includes administering to a host an effective amount of the inventive benzimidazole compounds.

Anti-viral compound

The present application provides a series of benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus and flaviviruses such as hepatitis C and bovine diarrheal virus.

Certain vinyl acetylene benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus.

The present application provides a series of benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. Such compounds are also useful as intermediates for preparing additional benzimidazole antiviral compounds.

Ribosylated 2-amino-1,3,4-thiadiazoles having antiviral activity, methods of use and pharmaceutical formulations therefor.

Thiadiazole antiviral agents

Compounds of formula (I) ##STR1## wherein R.sup.1 is hydrogen, and R.sup.2 is cyano or --C(.dbd.S)--NH--R.sup.3 ; or

This invention provides for certain phenyl-substituted imidazo compounds, their pharmaceutical formulations, and their use as positive inotropic agents and vasodilators.

Inotropic agents

Methods of producing a positive inotropic effect or vasodilation by

Compounds of the formula ##STR1## in which Y is hydrogen or hydroxyl, useful as intermediates in the production of antibiotics, are prepared by reacting a sulfinic acid of the formula ##STR2## with an oxidizing agent.

Process for preparing oxazolinoazetidinones

7.beta.-Acylamino-3-azido-3-cephem-4-carboxylic acid esters are obtained with the corresponding 3-halo or 3-sulfonyloxy-3-cephem esters and an alkali metal azide. The 3-azido compounds as the free acids or salts are antibacterial agents while in esterified form react with alcohols and phenols to provide 2-alkoxy (or 2-phenoxy)-3amino-3-cephem esters and isomeric ring expanded 4,7-bicyclo .beta.-lactam compounds, namely [2R-(2.alpha.,7.alpha.,8.beta.)-4-alkoxy (or 4-phenoxy)-9-oxo-8-acylamino-6-thia-1,3-diazabicyclo[5.2.0]non-3-ene-2-car boxylic acids and esters and the corresponding 3-alkoxy (or 3-phenoxy) 1,4-diazabicyclo[5.2.0]non-3-ene-2-carboxylic acids and esters. These reaction products obtained with the azide possess antibacterial properties.

3-Azidocephalosporins

4-Fluoroazetidinone antibacterial agents are provided by a process comprising the reaction of an azetidinone-4-sulfinic acid, or a salt thereof, with perchloryl fluoride (FClO.sub.3) at -80.degree. C. to -25.degree. C., e.g., p-nitrobenzyl 3-methyl-2-(2-oxo-4-sulfino-3-phenoxyacetamido-1-azetidinyl-3-butenoate is reacted with FClO.sub.3 to provide corresponding 4-fluoroazetidinone. The latter is isomerized with a tertiary amine to corresponding 2-butenoate which a carboxy group deprotection provides an antibacterial compound.

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Indianapolis, IN, United States of America

Wayne A Spitzer