Patents Assigned to USV Pharmaceutical
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Patent number: 4588734Abstract: 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.These compounds possess antihypertensive and angiotensin converting enzyme inhibitory activity.Type: GrantFiled: November 19, 1984Date of Patent: May 13, 1986Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4585758Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.Type: GrantFiled: January 10, 1985Date of Patent: April 29, 1986Assignee: USV Pharmaceutical Corp.Inventors: Fu-chih Huang, John T. Suh, Jerry W. Skiles
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Patent number: 4579866Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof, wherein: R.sub.1 and R.sub.2 are independently H, OH, lower alkyl, lower alkoxy, aryloxy, heteroaryloxy, heteroaryl lower alkoxy, aryl, heteroaryl, aryl-lower alkyl, aryl-lower alkoxy, halogenated aryl-lower alkoxy, lower alkenyl, lower alkynyl, lower alkenoxy, lower alkynoxy, halogen or trifluoromethyl;A is H, aryl, lower alkyl, aryl-lower alkyl or heteroaryl; andB is ##STR2## n=0-6, wherein D is H, CONR.sub.3 R.sub.4, CO.sub.2 H, CO.sub.2 R.sub.5, CH.sub.2 OH or CH.sub.2 OR.sub.6,whereinR.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently H, lower alkyl, aryl, aryl-lower alkyl or heteroaryl;E is H, OH, lower alkyl, aryl or heteroaryl; andF is ##STR3## wherein G is the same as R.sub.1 and R.sub.2, useful for the treatment of allergy, asthma and inflammatory conditions.Type: GrantFiled: May 29, 1984Date of Patent: April 1, 1986Assignee: USV Pharmaceutical Corp.Inventors: David Stevenson, Robert C. Liu, Laurence L. Ho, Howard Jones, Stephen Coutts
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Patent number: 4579865Abstract: Compounds of the structure; ##STR1## and pharmaceutically acceptable salts thereof, wherein:R.sub.1 is H, alkyl, alkoxy, carboxyl, alkylcarboxy, trifluoromethyl, halogen, nitro or hydroxy;X is O, N, S or C;Y is O, N or S; andR.sub.2 is H, alkyl, cycloalkyl, aryl or heteroaryl useful in the treatment of ischemic heart disease and hypertriglyceridemia.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Charles A. Sutherland
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Patent number: 4578386Abstract: Provided are compounds of the structure: ##STR1## wherein R.sub.1, R.sub.3, R.sub.5 and R.sub.6 are independently H, alkyl, aralkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkenyl, alkynyl, hydroxy, hydroxyalkyl, alkoxy, mercapto, mercaptoalkyl, alkylthio, amino, alkylamino, aminoalkyl, formyl, carboxy and salts thereof, carbalkoxy, alkanoyl, cyano, nitro, halo, trifluoromethyl, alkylsulfonyl, aminosulfonyl, carbamoyl or cycloalkyl; andR.sub.7 is H, alkyl, aryl, aralkyl, oxo, or alkanoyl;wherein at least one of R.sub.1 R.sub.5 or R.sub.6 is an aryl, heteroaryl, or heteroaryl substituted with H, alkyl, halo, amino, trifluoromethyl or cyano.Type: GrantFiled: February 10, 1984Date of Patent: March 25, 1986Assignee: USV Pharmaceutical Corp.Inventor: Thomas D. Lee
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Patent number: 4576942Abstract: Compounds of the formulae ##STR1## wherein, A is benzo, pyrido, thieno, pyrazolo, imidazo, pyrimido, isoxazolo, thiazolo, furo or pyrrolo;X is O, S, SO or SO.sub.2 ;R.sub.1 is H, alkyl, aryl, OH, OR, aryloxy, halogen, amino, nitro, cyano, COOR, trihalomethyl, ##STR2## R.sub.2. R.sub.3, R.sub.4 and R.sub.5 are identical or different and each represent H, alkyl, aryl, OH, OR, amino, alkylamino, dialkylamino, COOR, thio, alkylthio, cyano, or halogen; and n is 1-2; and pharmaceutically acceptable salts thereof having anti-allergy and anti-inflammatory activity.Type: GrantFiled: July 12, 1984Date of Patent: March 18, 1986Assignee: USV Pharmaceutical Corp.Inventor: Raymond D. Youssefyeh
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Patent number: 4576941Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.Type: GrantFiled: February 29, 1984Date of Patent: March 18, 1986Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, John J. Piwinski, Howard Jones, Edward S. Neiss
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Patent number: 4569941Abstract: Compounds of the formulae: ##STR1## wherein, Z and Y are each alkylene or oxy-alkylene containing one to about five carbon atoms in the principal chain or said alkylene substituted with OH, alkanoyloxy, alkoxy, mercapto or alkylmercapto;each of R.sub.1, R.sub.2 and R.sub.3 is independently H, alkyl, aryl, halo, alkoxy, alkenyloxy, alkylsulfinyl, alkylsulfonyl, alkylmercapto, cyano, carboxy, carbalkoxy, carboxamido, sulfamoyl, trifluoromethyl, hydroxy, hydroxyalkyl, acyloxy, alkylamino, sulfonylamino, or acylamino; or R.sub.1 and R.sub.2, when taken together, form a methylenedioxy or --O--CO--O--;Ar is heteroaryl, cycloalkyl or ##STR2## wherein, R.sub.1, R.sub.2 and R.sub.3 are as hereindescribed; andR is H, alkyl, cycloalkyl, aryl, aralkyl, alkenyl, alkynyl, carboalkoxy, or CONR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is H or alkyl; wherein the total number of carbon atoms in each hydrocarbyl group is up to 10; and ##STR3## wherein, each of R.sub.1 and R.sub.Type: GrantFiled: January 17, 1985Date of Patent: February 11, 1986Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, Rack H. Chung, deceased, Nai-Yi Wang, Jeffrey N. Barton
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Patent number: 4567279Abstract: This invention relates to new chemical compounds which possess valuable therapeutic activity particularly as lipoxygenase inhibitors possessing antiflammatory and antiallergic properties. The present new compounds are of the formula: ##STR1## wherein, Z and Z.sub.1 each are alkylene chains containing up to three carbon atoms in the principal chain and a total of up to five carbon atoms and include from 0-1 double bonds;R is H or lower alkyl;R.sub.1 and R.sub.2 each are H, lower alkyl, OH, lower alkoxy, benzyloxy, carboxy, alkylenecarboxyl or alkylcarbonyl.R.sub.3 is H, lower alkyl, aralkyl or lower alkanoyl; andX is --O(CH.sub.2).sub.n --, --CH.dbd.CH--, --(CH.sub.2).sub.n --, --S(CH.sub.2).sub.n -- or ##STR2## n=0 or 1 n'=1 or 2.Type: GrantFiled: December 13, 1984Date of Patent: January 28, 1986Assignee: USV Pharmaceutical Corp.Inventor: Wan-kit Chan
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Patent number: 4567184Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen, alkyl, carboxy, alkylcarboxy, arylcarboxy, alkyl carbalkoxy, alkanoyl, formyl, nitrile, amino, amino alkyl, alkylamine, carboxamide, halo, trihalomethyl, hydroxy, alkoxy, aryloxy, nitro, sulfonyl, sulfonamide, thio, alkylthio, or R.sub.1 and R.sub.2 can be taken together to form a phenyl ring;B is C or N, in which N can be in any position of the ring;X is O, S, NR.sub.4, CH.sub.2 Z, CH.dbd.N, CH.dbd.CH, C.tbd.C, CH.sub.2 ZCH.sub.2, C.dbd.O, C.dbd.CR or WC.dbd.O;Y is CHCH.sub.2, C.dbd.CH, C--CH.sub.2, CHCHR.sub.5, CHC(R.sub.5).sub.2 or CC(R.sub.5).sub.2 ;R.sub.3 is O, OH, OR.sub.4, SH, SR.sub.4, NH, HNR.sub.4 or N(R.sub.4).sub.2 ; andM is an integer from 0 to 10; wherein Z is O, S or NR.sub.4 ; R.sub.4 is H, alkyl or aryl;W is O, S or NR.sub.4 ; and R.sub.5 is H, alkyl or fluoro have antiinflammatory and antiallergic activities.Type: GrantFiled: September 9, 1983Date of Patent: January 28, 1986Assignee: USV Pharmaceutical CorporationInventors: John H. Musser, Utpal R. Chakraborty
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Patent number: 4565825Abstract: 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. The compounds of the invention exhibit antihypertensive and angiotensin converting enzyme inhibitory activity.Type: GrantFiled: November 19, 1984Date of Patent: January 21, 1986Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4564677Abstract: Disclosed is a method of preparing N-amino compounds from corresponding secondary amines by reacting a secondary amine with nitrous acid and zinc in a neutral pH reaction media to form the corresponding N-amine.Type: GrantFiled: January 19, 1984Date of Patent: January 14, 1986Assignee: USV Pharmaceutical Corp.Inventor: Martin L. Kantor
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Patent number: 4563463Abstract: New quinoline compound, and the corresponding 1,2-; 1,3-; and 1,4-benzodiazines, the quinoline compounds being of the formulae: ##STR1## and salts thereof, wherein R is hydrogen, acyl, carboethoxy,(3-methoxyphen)acetyl,(2-phenyl)propionyl, dimethylcarbamoyl or methyl,R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, halo, trifluoromethyl, amino, lower alkyl amino, lower acylamino, cyano, aryl, aryl/lower alkylene, nitro, lower alkynyl, lower alkenyl, lower alkyl sulfinyl, lower alkyl sulfonyl, lower alkoxycarbonyl, carboxyl, lower alkoxy, lower alkanoyl, or lower alkenoyl,Y is oxygen, sulfur, nitrogen or R.sub.3 N wherein R.sub.Type: GrantFiled: November 2, 1984Date of Patent: January 7, 1986Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Richard E. Brown
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Patent number: 4558038Abstract: Compounds of the formula ##STR1## wherein R and R.sub.9 are independently hydroxy and lower alkoxy,R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, aryl-lower alkyl having from 7 to 12 carbon atoms, or heterocycliclower alkyl having from 6 to 12 carbon atoms,R.sub.3, R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are hydrogen or lower alkyl,R.sub.6 is heterocyclicand their pharmaceutically acceptable, nontoxic acid addition salts and where R or R.sub.9 or both are hydroxy, their pharmaceutically acceptable, nontoxic basic salts, possess antihypertensive activity.Type: GrantFiled: November 15, 1984Date of Patent: December 10, 1985Assignee: USV Pharmaceutical Corp.Inventors: Jerry W. Skiles, Raymond D. Youssefyeh, John T. Suh, Howard Jones
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Patent number: 4556652Abstract: Compounds having the general structure ##STR1## and their pharmaceutically acceptable salts, wherein the substitutents are defined herein, which exhibit antihypertensive activity.Type: GrantFiled: March 2, 1984Date of Patent: December 3, 1985Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, Jerry W. Skiles, John J. Piwinski, Paul Menard, Howard Jones
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Patent number: 4555508Abstract: Compounds having the general structure ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are defined herein, which exhibit antihypertensive activity.Type: GrantFiled: March 2, 1984Date of Patent: November 26, 1985Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, John R. Regan, John J. Piwinski, Paul Menard, Howard Jones
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Patent number: 4552876Abstract: Compounds of the formula: ##STR1## wherein, R is H, alkyl, cycloalkyl, aryl, or heteroaryl;R.sub.1 is H, alkyl, cycloalkyl, aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aryl, halo, OR.sup.2, SR.sup.2, NR.sub.2, CF.sub.3, NO.sub.2, CN, COOR.sup.2, CHO, SO.sub.3 H or SO.sub.2 NH.sub.2,whereinR.sup.2 is H, methyl, ethyl or propyl;Y is ##STR2## Z is O, S, NH or CH.sub.2 ; X is --CH.sub.2 --, ##STR3## or --(CH.sub.2).sub.n CHOH(CH.sub.2).sub.n --; whereinR.sup.2 is H, methyl, ethyl or propyl;n is 1-10, and pharmaceutically acceptable salts thereof have antiallergy and antiinflammatory activity.Type: GrantFiled: July 9, 1984Date of Patent: November 12, 1985Assignee: USV Pharmaceutical Corp.Inventors: Howard Jones, Ernest Magnien, John H. Musser, Mujahid L. Shaikh
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Patent number: 4549992Abstract: 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 independently 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, aryalkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylaminoalkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused hetero-aryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is a group of the formula ##STR2## wherein X is a branched alkane or cycloalkyl; and where Y is hydroxy their non-toxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts.Type: GrantFiled: March 8, 1982Date of Patent: October 29, 1985Assignee: USV Pharmaceutical Corp.Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4548928Abstract: 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: GrantFiled: November 19, 1984Date of Patent: October 22, 1985Assignee: USV Pharmaceutical Co.Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4547509Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sub.1 is H, alkyl, alkoxy, carboxyl, alkylcarboxy, acylamino, dialkyl amino, trihalomethyl, halogen, nitro, hydroxy or cyano;X is in the 5, 6 or 7 position and is O(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3, S(CH.sub.2).sub.n or (CH.sub.2).sub.n ;Y is O(CH.sub.2).sub.n, S(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3 where R.sub.3 is H, alkyl or (CH.sub.2).sub.n ;R.sub.2 is monosubstituted or independently disubstituted H, hydroxy, alkyl, halogen, nitro, alkoxy, carboxyl, alkylcarboxy, trihalomethyl, cyano, trifluoromethyl, dialkylamino or acylamino;Z is O, S or (NR.sub.3).sub.2 where R.sub.3 is H, alkyl or aryl; andn is 0 to 10 inclusiveuseful in the treatment of ischemic heart disease and hypertriglyceridemia.Type: GrantFiled: January 3, 1983Date of Patent: October 15, 1985Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Charles A. Sutherland