American Home Products Corporation

Bradford H Hirth

John Anthony Butera

Schuyler A Antane

Madelene M Antane

Russell F Graceffa

Dominick Anthony Quagliato

Geraldine Ruth McFarlane

Eric Gould Gundersen

David R Herbst

The compounds of the formula: ##STR1## wherein R.sub.1 is straight chain alkyl, branched chain alkyl, cycloalkyl, hydroxyalkyl, fluoroalkyl or polyfluoroalkyl; R.sub.2 and R.sub.3 are, independently, hydrogen or an acyl substituent selected from the group consisting of formyl, alkanoyl, alkenoyl, alkoxycarbonyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; or a pharmaceutically acceptable salt thereof, relaxes smooth muscles.

Substituted N-arylmethylamino derivatives of cyclobutene-3,4-diones

The compounds of the formula: ##STR1## wherein R.sub.1 is straight chain alkyl, branched chain alkyl, cycloalkyl, hydroxyalkyl, fluoroalkyl or polyfluoroalkyl; R.sub.7 and R.sub.8 are, independently, hydrogen or an acyl substituent selected from the group consisting of formyl, alkanoyl, alkenoyl, alkoxycarbonyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; A is a phenyl group with either two or three substituents of the following formula: ##STR2## wherein the positions of substitution are R.sub.2,R.sub.3 -, R.sub.2,R.sub.4 -, R.sub.2,R.sub.5 -, R.sub.2,R.sub.6 -, R.sub.3,R.sub.4 -, R.sub.3,R.sub.5 -, and R.sub.2,R.sub.4,R.sub.6 - and R.sub.2 is methyl, ethyl, fluoro, chloro, methoxy or trifluoromethyl; R.sub.3 is methyl, ethyl, fluoro, chloro, methoxy or trifluoromethyl; R.sub.4 is methyl, fluoro, bromo, methoxy or cyano; R.sub.5 is methyl, fluoro, chloro, methoxy, cyano or trifluoromethyl; R.sub.6 is methyl, fluoro, chloro, or methoxy; or a pharmaceutically acceptable salt thereof, relax smooth muscles.

Substituted N-arylmethylamino derivatives of cyclobutene-3, 4-diones

The compounds of the formula: ##STR1## wherein R.sub.1 is straight chain alkyl, branched chain alkyl cycloalkyl, hydroxyalkyl, fluoroalkyl or polyfluoroalkyl; R.sub.2 and R.sub.3 are, independently, hydrogen or an acyl substituent selected from the group consisting of formyl, alkanoyl, alkenoyl, alkoxycarbonyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; A is a substituted phenyl group of the following formula: ##STR2## wherein R.sub.4 and R.sub.5 are, independently, cyano, nitro, amino, alkyl, perfluoroalkyl, fluoroalkyl, alkoxy, perfluoroalkoxy, fluoroalkoxy, amino, alkylamino, dialkylamino, sulfamyl, alkylsulfonamido, arylsulfonamido, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, alkylcarboxamido, arylcarboxamido, alkylsulfonyl, perfluoroalkylsulfonyl, arylsulfonyl, chloro, bromo, fluoro, iodo, 1-imidazolyl, carboxyl or hydrogen, with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen; or a pharmaceutically acceptable salt thereof, relaxes smooth muscles.

The compounds of formula I are smooth muscle relaxants: ##STR1## wherein R.sub.1 is hydrogen, alkyl, cycloalkyl, alkanoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; R.sub.2 is hydrogen, alkyl or cyclic or bicyclic alkyl; A is selected from the following: ##STR2##

Substituted N-heteroaryl-1,2-diaminocyclobutene-3,4-dione compounds

The compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independent from each other, hydrogen, alkyl, or cyclic or bicyclic alkyl; R.sub.3 is an acyl substituent selected from the group consisting of formyl, alkanoyl, alkenoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; A is selected from the group consisting of: ##STR2## wherein R.sub.4 is hydrogen, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano or carboxyl; or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.

Diaminocyclobutene-3,4-diones

The compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independent from each other, hydrogen, alkyl or cyclic or bicyclic alkyl; R.sub.3 is an acyl substituent selected from the group consisting of formyl, alkanoyl, alkenoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; A is selected from the group consisting of: ##STR2## wherein R.sub.4 is hydrogen, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano or carboxyl; or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.

The compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, alkanoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; R.sub.2 is hydrogen, straight or branched chain alkyl or cyclic or bicyclic alkyl; A is selected from the following: ##STR2## wherein R.sub.9 is hydrogen, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, mono- or dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano, carboxyl, chloro, bromo, fluoro or iodo; n is an integer from 0 to 6; R.sub.3 and R.sub.4, independent from each other, are hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, perfluoroalkyl, hydroxyalkyl, alkoxyalkyl, fluoro, or, when taken together, form a spirocyclic ring; R.sub.5 and R.sub.6, independent from each other, are selected from the following: cyano, nitro, amino, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, mono- or dialkylamino, sulfonamide, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfonyl, perfluoroalkylsulfonyl, arylsulfonyl, chloro, bromo, fluoro, iodo, 1-imidazolyl, carboxyl, carboalkoxy, hydroxyl, or hydrogen; and the pharmaceutically acceptable salts thereof relax smooth muscles.

The compounds of formula I: ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, alkyl or cyclic or bicyclic alkyl; R.sub.3 is formyl, alkanoyl, alkenoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl arylalkanoyl or arylalkylsulfonyl; A is a substituted phenyl group of the following formula: ##STR2## wherein R.sub.5 is cyano and R.sub.6 is alkyl, chloro, bromo, fluoro or iodo and pharmaceutically acceptable salts thereof, are smooth muscle relaxants.

The compound of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are, independent from each other, hydrogen, C.sub.1-10 straight chain alkyl, C.sub.1-10 branched alkyl, or C.sub.3-10 cyclic or bicyclic alkyl;

The compound of the formula (I) or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants ##STR1##

Substituted n-aryl-1,2-diaminocyclobutene-3,4-diones

The compound of the formula (I) or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants. ##STR1##

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Monmouth Junction, NJ, United States of America

Bradford H Hirth