Patents Assigned to USV Pharmaceutical Corp.
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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: 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: 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
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Patent number: 4542234Abstract: The (S,S) optical isomer of a compound having the general formula ##STR1## wherein R and R.sub.1-5 are as defined herein, is recovered essentially free of the (R,S) and (S,R) isomers, by forming a solution of the esters of the (S,S) and the (R,S) and/or (S,R) isomers of said compound, selectively precipitating an acid salt (e.g. maleate) of the (S,S) ester from the solution, and treating the precipitate to form the desired free acid.Type: GrantFiled: October 6, 1983Date of Patent: September 17, 1985Assignee: USV Pharmaceutical Corp.Inventors: Laurence W. Reilly, Jr., Jeffrey N. Barton
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Patent number: 4534979Abstract: Polyene compounds represented by the general formulae ##STR1## in which: R and R.sub.1 are each hydrogen or an alkyl group of from 1 to 5 carbon atoms;R.sub.2 is an alkyl group of from 1 to 5 carbon atoms;R.sub.3 is hydroxyl, alkoxy of from 1 to 5 carbon atoms, NH.sub.2, NHR.sub.2 or NR.sub.2 R.sub.2 and Z is a cycloalkyl, cycloalkenyl or cycloalkdienyl group substituted with from 0 to 5 alkyl groups, a keto group or a hydroxyl group or a phenyl group substituted with from 0 to 4 hydroxy, alkoxy, alkyl, aryloxy, aralkyloxy or trifluoromethyl groups or halogen atoms or combinations thereof and the pharmaceutically-acceptable salts thereof.The foregoing compounds have been found to be effective in the treatment of psoriasis, inflammatory conditions and allergic responses.Type: GrantFiled: November 2, 1984Date of Patent: August 13, 1985Assignee: USV Pharmaceutical Corp.Inventors: Bernard Loev, Wan-Kit Chan, Howard Jones
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Patent number: 4535177Abstract: Optical isomeric compounds having the general formula ##STR1## are prepared by: reacting by catalytic hydrogenation a compound of the formula ##STR2## with a compound of the formula ##STR3## wherein R, R.sub.1, R.sub.2 and R.sub.3 are as defined herein, to form a mixture of isomers in a ratio of L(S)L(S)>D(R)L(S); and recovering the (S,S) diastereomer by selectively precipitating an acid salt of the (S,S) ester from the solution.Type: GrantFiled: November 14, 1983Date of Patent: August 13, 1985Assignee: USV Pharmaceutical Corp.Inventors: Frederick A. Golec, Jr., Thomas Goetzen
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Patent number: 4530931Abstract: X is in the 8 position and is O(CH.sub.2).sub.n, N(CH.sub.2).sub.n ;Y is O(CH.sub.2).sub.n, N(CH.sub.2).sub.n ;R.sub.2 is monosubstituted or independently disubstituted H, carboxyl, or alkylcarboxy;Z is 0; andn is 0 to 10 inclusive,useful in the treatment of ischemic heart disease and hypertriglyceridemia.Type: GrantFiled: March 21, 1984Date of Patent: July 23, 1985Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Charles A. Sutherland