Sterling Winthrop Inc.

Sanofi

Sanofi Sa

Sanofi Pharmaceuticals, Inc.

David J Aldous

Guy D Diana

Thomas R Bailey

Theodore John Nitz

Gee-Hong Kuo

Michael Reuman

Compounds of the formula ##STR1## wherein Azo is alkyltetrazolyl or is chosen from the group consisting of oxadiazolyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, triazinyl, thiazolyl, isothiazolyl or any of these substituted with a member of the group consisting of alkyl, alkylthio, alkoxy, hydroxy, halo, cyano, nitro, hydroxyalkyl, alkoxyalkyl, alkoxycarbonyl, alkanoyl, fluoroalkyl or the N-oxide of any of the preceding;

Therapeutic phenoxyalkylazoles and phenoxyalkylazines

Compounds of the formula; ##STR1## wherein: Thi is thiadiazolyl or substituted thiadiazolyl alkoxy, fluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, halo, alkyl, cycloalkyl, hydroxyalkyl, or

Thiadiazoles and their uses as antipicornaviral agents

Compounds of the formula ##STR1## wherein Pyr is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substitutents chosen from alkyl, alkoxy, hydroxy, halo, cyano, nitro, hydroxyalkyl, alkoxyalkyl, alkanoyl, fluoroalkyl or the N-oxide of any of these;

Therapeutic phenoxyalkylheterocycles

Described herein are compound of the formula: ##STR1## wherein: Thi is thiadiazolyl or substituted thiadiazolyl;

Thiadiazoles and their use as antipicornaviral agents

Compounds of the formula ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the specification,

Therapeutic phenoxyalkylpyridazines and intermediates therefor

Described herein are compounds of the formula; ##STR1## wherein: Thi is a unsubstituted or substituted thiadiazolyl;

Compounds of the formula ##STR1## wherein Q is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substituents; Y is an alkylene bridge of 3-9 carbon atoms; R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl or cyano; R.sub.3 is alkoxycarbonyl, alkyltetrazolyl, substituted or unsubstituted phenyl or heterocyclyl, the N-oxide thereof, or a pharmaceutically acceptable acid addition salt thereof is an effective antipicornaviral agent.

A compound of the formula ##STR1## wherein Y, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined in the specification.

Heterocycle substituted phenoxyalkylheterocycles and their use as

The invention pertains to heterocycle substituted phenoxyalkylheterocycles of the formula ##STR1## wherein Thi, Y, R.sub.1, R.sub.2 and R.sub.3 are as defined in the specification, or a pharmaceutically acceptable salt thereof which are effective antipicornaviral agents.

Compounds of the formula ##STR1## wherein Azo is alkyltetrazolyl, oxadiazolyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, triazinyl, thiazolyl, isothiazolyl;

Disclosed herein are compounds and pharmaceutical compositions useful for combating picornaviruses and preventing or treating picornaviral infections. The compounds have the formula: ##STR1## wherein Het.sub.1 is chosen from the group consisting of oxazolyl, isoxazolyl, oxadiazolyl;

Antipicornaviral agents

The invention discloses compounds of the formula ##STR1## wherein, Het.sub.1 is chosen from the group consisting of substituted or unsubstituted furyl, oxazolyl, isoxazolyl, oxadiazolyl, tetrazolyl, thiadiazolyl Y is an alkylene bridge of 3 to 9 carbon atoms. Het.sub.2 is quinolyl quinolyl substituted by R.sub.1 and R.sub.2 ; R.sub.1 and R.sub.2 are each individually chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinyl alkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl or cyano; R.sub.3 is alkyltetrazolyl, or substituted or unsubstituted heterocyclyl chosen from benzoxazolyl, benzathiazolyl, thiadiazolyl, imidazolyl, dihydroimidazolyl, oxazolyl, thiazolyl, oxadiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, furyl, triazolyl, tetrazolyl, thiophenyl the N-oxide thereof or a pharmaceutically acceptable acid addition salt thereof are effective antipicornaviral agents.

Substituted quinoline derivatives useful as antipiconaviral agents

Compounds of the formula ##STR1## wherein: R.sub.1 and R.sub.2 are independently hydrogen, halo, alkyl, alkenyl, alkoxy, hydroxy, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, alkylthioalkynyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, amino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy or cyanomethyl, nitro, difluoromethyl, trifluoromethyl or cyano; Y is alkylene of 3 to 9 carbon atoms; R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkanoyl, alkanoyloxy, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, cyanomethyl, fluoroalkyl, cyano, phenyl, alkynyl, alkene, or halo; R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle; or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.

Therapeutic phenoxyalklpyridazines and intermediates therefor

Compounds of the formula; ##STR1## wherein: Thi is thiadiazolyl or substituted thiadiazolyl;

Growing community of inventors

Glenmore, PA, United States of America

David J Aldous