Patent number: 4548928
Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is heterocyclic or heterocyclic alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ##STR2## wherein Z is hydrogen, alkyl, hydroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, n, M and Y are as described above; and where Y is hydroxy their nontoxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts.
Type:
Grant
Filed:
November 19, 1984
Date of Patent:
October 22, 1985
Assignee:
USV Pharmaceutical Co.
Inventors:
John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
Patent number: 4507312
Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is heterocyclic or heterocyclic alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hydroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, n, M and Y are as described above; and where Y is hydroxy their nontoxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts.
Type:
Grant
Filed:
November 23, 1981
Date of Patent:
March 26, 1985
Assignee:
USV Pharmaceutical Corporation
Inventors:
John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
Patent number: 4347246
Abstract: A compound of the formula ##STR1## wherein: R.sub.1 is independently lower alkyl having from 1 to 6 carbon atoms, lower alkenyl having from 2 to 6 carbon atoms, lower alkynyl having from 2 to 6 carbon atoms, hydroxy, hydroxyalkyl, alkoxy, thio, thioalkyl, alkylmercapto, amino, aminoalkyl, alkylamino, nitro, cyano, alkanoyl, carboxy, carboxyalkyl, carbalkoxy, carbalkoxyalkyl, halogen, alkylsulfoxy, alkylsulfonyl, sulfonyl, sulfonamido, trifluoromethyl, or methylenedioxy, wherein the alkyl group in hydroxyalkyl, thioalkyl, aminoalkyl, carboxyalkyl, alkoxy, alkylmercapto, alkylsulfoxy, alkanoyl, carbalkoxy, and carbalkoxyalkyl has from 1 to 6 carbon atoms,n is an integer from 1 to 4 inclusive,R.sub.2 is selected from the group consisting of hydrogen and cycloalkyl, wherein the cycloalkyl group contains from 3 to 16 carbon atoms,R.sub.3 and R.sub.4 are hydrogen, andY is oxygen, sulphur, .dbd.NR.sub.1, .dbd.NOR.sub.1 or .dbd.N--NH.sub.2, R.sub.1 being the same as defined above.
Type:
Grant
Filed:
May 15, 1980
Date of Patent:
August 31, 1982
Assignee:
USV Pharmaceutical Corporation
Inventors:
John T. Suh, Bruce E. Williams, Jerry W. Skiles, Bernard Loev
Patent number: 4304771
Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is heterocyclic or heterocyclic alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, kydroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, n, M and Y are as described above; and where Y is hydroxy their nontoxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts.
Type:
Grant
Filed:
October 24, 1980
Date of Patent:
December 8, 1981
Assignee:
USV Pharmaceutical Corporation
Inventors:
John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
Patent number: 4287203
Abstract: Antihypertensive compounds of the structure ##STR1## wherein: n is an integer from 0 to 2 inclusive,R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are independently hydrogen, alkyl having from 1 to 6 carbon atoms, alkenyl having from 2 to 6 carbon atoms, alkynyl having from 2 to 6 carbon atoms, cycloalkyl having from 3 to 16 carbon atoms, phenyl, benzyl, tolyl, naphthyl, phenethyl, indanyl, tetrahydronaphthyl, decanydronaphthyl, pyridyl, quinolyl, pyrrolidyl, pyrrolyl, morpholinyl, thiomorpholinyl, furyl, furfuryl, tetrahydrofurfuryl, benzimidazole, thienyl, imidolyl, or tetrahydroindolyl, and where the R.sub.1 to R.sub.7 groups are alkyl, said groups carrying a substituent selected from hydroxy, alkoxy, amino, carboxy, or carbalkoxy, the alkyl group in alkoxy and carbalkoxy having from 1 to 6 carbon atoms, or R.sub.2 taken together with R.sub.3 and the carbons to which they are attached is tetrahydronaphthyl or phenyl, and when phenyl R.sub.1 and R.sub.4 are absent, or R.sub.6 and R.sub.
Type:
Grant
Filed:
April 23, 1980
Date of Patent:
September 1, 1981
Assignee:
USV Pharmaceutical Corporation
Inventors:
John T. Suh, Bruce E. Williams, Jerry W. Skiles, Bernard Loev
Patent number: 4256761
Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycyclo-alkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylamino-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hyroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.
Type:
Grant
Filed:
July 13, 1979
Date of Patent:
March 17, 1981
Assignee:
USV Pharmaceutical Corporation
Inventors:
John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab