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Substituted isoxazoles for the treatment of inflammation

Bibliographic Details
Title: Substituted isoxazoles for the treatment of inflammation
Patent Number: 5,633,272
Publication Date: May 27, 1997
Appl. No: 08/473,884
Application Filed: June 07, 1995
Abstract: A class of substituted isoxazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.1 is selected from hydroxyl, lower alkyl, carboxyl, lower carboxyalkyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower aralkyl, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower haloalkyl, lower hydroxylalkyl, cycloalkyl, cycloalkylalkyl, and aralkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, aryl, and heteroaryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from lower alkyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Inventors: Talley, John J. (Brentwood, MO); Brown, David L. (Chesterfield, MO); Nagarajan, Srinivasan (Chesterfield, MO); Carter, Jeffery S. (Chesterfield, MO); Weier, Richard M. (Lake Bluff, IL); Stealey, Michael A. (Libertyville, IL); Collins, Paul W. (Deerfield, IL); Rogers, deceased, Roland S. (late of Richmond Heights, MO); Seibert, Karen (St. Louis, MO)
Claim: What is claimed is
Claim: 1. A compound of Formula II ##STR32## wherein R.sup.1 is selected from alkyl, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyl, amino, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl;
Claim: wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, hydroxyalkyl, haloalkoxy, amino, alkylamino, arylamino, aminoalkyl, nitro, alkoxyalkyl, alkylsulfinyl, alkylsulfonyl, aminosulfonyl, halo, alkoxy and alkylthio; and
Claim: wherein R.sup.4 is selected from lower alkyl, hydroxyl, and amino;
Claim: or a pharmaceutically-acceptable salt thereof.
Claim: 2. A compound of claim 1 wherein R.sup.1 is selected from hydroxyl, amino, lower alkyl, lower carboxyalkyl, lower alkoxycarbonyl, aminocarbonyl, carboxyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower alkoxy, lower haloalkoxy, lower aralkoxy, lower cycloalkylalkoxy, lower alkylthio, lower aralkylthio, lower cycloalkylalkylthio, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower hydroxyalkyl, lower haloalkyl, lower cycloalkyl, lower cycloalkylalkyl, lower aralkyl, halo, lower alkylamino, lower aralkylamino, lower N-alkyl-N-aralkylamino, lower N-alkyl-N-cycloalkylalkylamino, lower arylcarbonyloxyalkyl, lower alkoxycarbonyloxyalkyl, lower alkylaminocarbonyloxyalkyl, lower alkoxycarbonylthioalkyl, and lower alkylaminocarbonylthioalkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, lower alkylsulfonyl, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Claim: 3. A compound of claim 2 wherein R.sup.1 is selected from hydroxyl, lower alkyl, carboxyl, lower carboxyalkyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower aralkyl, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower haloalkyl, lower hydroxylalkyl, cycloalkyl, cycloalkylalkyl, and aralkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Claim: 4. A compound of claim 3 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected form benzyl and phenylethyl, wherein the phenyl ring is optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, aminosulfonyl, methylthio, ethylthio, butylthio, and hexylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Claim: 5. The compound of claim 4 which is 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
Claim: 6. A compound of Formula III ##STR33## wherein R.sup.1 is selected from hydroxyl, alkyl, carboxyalkyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl; and
Claim: wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, hydroxyalkyl, haloalkoxy, amino, alkylamino, arylamino, aminoalkyl, nitro, alkoxyalkyl, alkylsulfinyl, aminosulfonyl, halo, alkoxy and alkylthio; or a pharmaceutically-acceptable salt thereof.
Claim: 7. A compound of claim 6 wherein R.sup.1 is selected from hydroxyl, lower alkyl, carboxyl, lower carboxyalkyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower aralkyl, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower haloalkyl, lower hydroxylalkyl, lower cycloalkyl, lower cycloalkylalkyl, and aralkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; and wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, aminosulfonyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy and lower alkylthio; or a pharmaceutically-acceptable salt thereof.
Claim: 8. A compound of claim 7 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected from phenylethyl and benzyl optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; and wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, aminomethyl, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, methylthio, aminosulfonyl, ethylthio, butylthio, and hexylthio; or a pharmaceutically-acceptable salt thereof.
Claim: 9. A pharmaceutical composition comprising a therapeutically-effective amount of a compound, said compound selected from a family of compounds of Formula II ##STR34## wherein R.sup.1 is selected from alkyl, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyl, amino, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl;
Claim: 10. A pharmaceutical composition of claim 9 wherein R.sup.1 is selected from hydroxyl, amino, lower alkyl, lower carboxyalkyl, lower alkoxycarbonyl, aminocarbonyl, carboxyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower alkoxy, lower haloalkoxy, lower aralkoxy, lower cycloalkylalkoxy, lower alkylthio, lower aralkylthio, lower cycloalkylalkylthio, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower hydroxyalkyl, lower haloalkyl, lower cycloalkyl, lower cycloalkylalkyl, lower aralkyl, halo, lower alkylamino, lower aralkylamino, lower N-alkyl-N-aralkylamino, lower N-alkyl-N-cycloalkylalkylamino, lower arylcarbonyloxyalkyl, lower alkoxycarbonyloxyalkyl, lower alkylaminocarbonyloxyalkyl, lower alkoxycarbonylthioalkyl, and lower alkylaminocarbonylthioalkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, lower alkylsulfonyl, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Claim: 11. A pharmaceutical composition of claim 10 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected form benzyl and phenylethyl, wherein the phenyl ring is optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, aminosulfonyl, methylthio, ethylthio, butylthio, and hexylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Claim: 12. A pharmaceutical composition of claim 11 wherein said compound is 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
Claim: 13. A pharmaceutical composition comprising a therapeutically-effective amount of a compound, said compound selected from a family of compounds of Formula III ##STR35## wherein R.sup.1 is selected from hydroxyl, alkyl, carboxyalkyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl; and
Claim: 14. A method of treating inflammation or an inflammation-associated disorder in a subject, said method comprising administering to the subject having or susceptible to said inflammation or inflammation-associated disorder, a therapeutically-effective amount of a compound of Formula II ##STR36## wherein R.sup.1 is selected from alkyl, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyl, amino, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl;
Claim: 15. A method of claim 14 wherein R.sup.1 is selected from hydroxyl, amino, lower alkyl, lower carboxyalkyl, lower alkoxycarbonyl, aminocarbonyl, carboxyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower alkoxy, lower haloalkoxy, lower aralkoxy, lower cycloalkylalkoxy, lower alkylthio, lower aralkylthio, lower cycloalkylalkylthio, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower hydroxyalkyl, lower haloalkyl, lower cycloalkyl, lower cycloalkylalkyl, lower aralkyl, halo, lower alkylamino, lower aralkylamino, lower N-alkyl-N-aralkylamino, lower N-alkyl-N-cycloalkylalkylamino, lower arylcarbonyloxyalkyl, lower alkoxycarbonyloxyalkyl, lower alkylaminocarbonyloxyalkyl, lower alkoxycarbonylthioalkyl, and lower alkylaminocarbonylthioalkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, lower alkylsulfonyl, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Claim: 16. A method of claim 15 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected form benzyl and phenylethyl, wherein the phenyl ring is optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, aminosulfonyl, methylthio, ethylthio, butylthio, and hexylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
Claim: 17. A method of claim 16 wherein said compound is 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
Claim: 18. A method of treating inflammation or an inflammation-associated disorder in a subject, said method comprising administering to the subject having or susceptible to said inflammation or inflammation-associated disorder, a therapeutically-effective amount of a compound of Formula III ##STR37## wherein R.sup.1 is selected from hydroxyl, alkyl, carboxyalkyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl; and
Claim: 19. A method of claim 14 for use in treatment of inflammation.
Claim: 20. A method of claim 14 for use in treatment of an inflammation-associated disorder.
Claim: 21. A method of claim 20 wherein the inflammation-associated disorder is arthritis.
Claim: 22. A method of claim 20 wherein the inflammation-associated disorder is pain.
Claim: 23. A method of claim 20 wherein the inflammation-associated disorder is fever.
Claim: 24. The compound of claim 4 selected from compounds, or their pharmaceutically acceptable salts, of the group consisting of
Claim: 4-[5-ethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-propyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-isopropyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-butyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-isobutyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-cyclohexyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-neopentyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-cyclohexylmethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-(4-chlorophenyl)methyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-trifluoromethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-difluoromethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-chloromethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-methyl-3-phenylisoxazol-4-yl]benzenesulfonic acid;
Claim: 4-[5-propyl-3-phenylisoxazol-4-yl]benzenesulfonic acid;
Claim: 4-[5-methoxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-3-hydroxypropyl)-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-4-chlorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-4-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-3-fluoro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-3-aminosulfonyl-4-methoxyphenyl)-5-methyl-isoxazol-4-yl]benzenesulfona mide;
Claim: 4-[3-3-chloro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-3-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]carboxylic acid;
Claim: 4-[5-hydroxy-3-phenyl-4-isoxazolyl]benzenesulfonamide;
Claim: 4-[3-methyl-5-phenyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-(3-fluoro-4-methoxyphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: [3-(3-chloro-4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]isoxazol-5-yl]ace tic acid;
Claim: 5-methyl-4-[4-(methylsulfonyl)phenyl]-3-phenyl-isoxazole;
Claim: 3-(3-chloro-4-methoxyphenyl)-5-methyl-4-[4-(methylsulfonyl)phenyl]isoxazole
Claim: [4-[4-(aminosulfonyl)phenyl]-3-phenyl-isoxazol-5-yl]acetic acid;
Claim: [4-[4-(aminosulfonyl)phenyl]-3-phenyl-isoxazol-5-yl]propanoic acid;
Claim: ethyl [4-[4-(aminosulfonyl)phenyl]-3-phenyl-isoxazol-5-yl]propanoate;
Claim: [3-(3-fluoro-4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]isoxazol-5-yl]ace tic acid; and
Claim: [4-[4-(aminosulfonyl)phenyl]-3-(3-fluoro-4-methoxyphenyl)isoxazol-5-yl]prop anoic acid.
Claim: 25. The compound of claim 4 which is 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
Claim: 26. A pharmaceutical composition of claim 11 wherein said compound is selected from compounds, or their pharmaceutically-acceptable salts, of the group consisting of
Claim: 3-(3-chloro-4-methoxyphenyl)-5-methyl-4-[4-(methylsulfonyl)phenyl]isoxazole ;
Claim: 27. A pharmaceutical composition of claim 11 wherein said compound is 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
Claim: 28. A method of claim 16 wherein said compound is selected from compounds, or their pharmaceutically-acceptable salts, of the group consisting of
Claim: 4-[5isopropyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[5-(3-hydroxypropyl)-3-phenylisoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-(4-chlorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-(4-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-(3-fluoro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-(3-aminosulfonyl-4-methoxyphenyl)-5-methyl-isoxazol-4-yl]benzenesulfon amide;
Claim: 4-[3-(3-chloro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 4-[3-(3-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
Claim: 29. A method of claim 16 wherein said compound is 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
Current U.S. Class: 514/378; 548/182; 548/186; 548/190; 548/193; 548/202; 548/203; 548/225; 548/228; 548/229; 548/232; 548/234; 548/235; 548/243; 548/245; 548/247; 548/248; 5462/721; 544/405; 514/255; 514/340; 514/365; 514/369; 514/370; 514/374; 514/376; 514/377; 514/380
Current International Class: C07D26106; C07D26110; C07D26112; C07D26114; A61K 3142
Patent References Cited: 5310926 May 1994 Hagiwara et al.
5318970 June 1994 Suzuki et al.
Other References: Ichiro Yamawaki et al, Chem. Pharm. Bull., 36:3142-3146 @(1988).
Umezawa et al, Bull. Chem. Soc. Jpn vol. 36, No. 9, pp. 1150-1154 Sep. (1963).
Descamps et al, Bull. Soc. Chim. Belg., 73:459-82 (1964).
Hagiwara et al. CA 114:42776k, @1991.
Nagai et al., CA 117:212485w, @1992.
Primary Examiner: Richter, Johann
Assistant Examiner: Stockton, Laura L.
Attorney, Agent or Firm: Bulock, Joseph W.
Accession Number: edspgr.05633272
Database: USPTO Patent Grants
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Items – Name: Title
  Label: Title
  Group: Ti
  Data: Substituted isoxazoles for the treatment of inflammation
– Name: DocumentID
  Label: Patent Number
  Group: Patent
  Data: 5,633,272
– Name: DateEntry
  Label: Publication Date
  Group: Patent
  Data: May 27, 1997
– Name: DocumentID
  Label: Appl. No
  Group: Patent
  Data: 08/473,884
– Name: DateFiled
  Label: Application Filed
  Group: Patent
  Data: June 07, 1995
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: A class of substituted isoxazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.1 is selected from hydroxyl, lower alkyl, carboxyl, lower carboxyalkyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower aralkyl, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower haloalkyl, lower hydroxylalkyl, cycloalkyl, cycloalkylalkyl, and aralkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, aryl, and heteroaryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from lower alkyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Author
  Label: Inventors
  Group: Patent
  Data: <searchLink fieldCode="ZA" term="%22Talley%2C+John+J%2E%22">Talley, John J.</searchLink> (Brentwood, MO); <searchLink fieldCode="ZA" term="%22Brown%2C+David+L%2E%22">Brown, David L.</searchLink> (Chesterfield, MO); <searchLink fieldCode="ZA" term="%22Nagarajan%2C+Srinivasan%22">Nagarajan, Srinivasan</searchLink> (Chesterfield, MO); <searchLink fieldCode="ZA" term="%22Carter%2C+Jeffery+S%2E%22">Carter, Jeffery S.</searchLink> (Chesterfield, MO); <searchLink fieldCode="ZA" term="%22Weier%2C+Richard+M%2E%22">Weier, Richard M.</searchLink> (Lake Bluff, IL); <searchLink fieldCode="ZA" term="%22Stealey%2C+Michael+A%2E%22">Stealey, Michael A.</searchLink> (Libertyville, IL); <searchLink fieldCode="ZA" term="%22Collins%2C+Paul+W%2E%22">Collins, Paul W.</searchLink> (Deerfield, IL); <searchLink fieldCode="ZA" term="%22Rogers%2C+deceased%2C+Roland+S%2E%22">Rogers, deceased, Roland S.</searchLink> (late of Richmond Heights, MO); <searchLink fieldCode="ZA" term="%22Seibert%2C+Karen%22">Seibert, Karen</searchLink> (St. Louis, MO)
– Name: Comment
  Label: Claim
  Group: Patent
  Data: What is claimed is
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 1. A compound of Formula II ##STR32## wherein R.sup.1 is selected from alkyl, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyl, amino, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, hydroxyalkyl, haloalkoxy, amino, alkylamino, arylamino, aminoalkyl, nitro, alkoxyalkyl, alkylsulfinyl, alkylsulfonyl, aminosulfonyl, halo, alkoxy and alkylthio; and
– Name: Comment
  Label: Claim
  Group: Patent
  Data: wherein R.sup.4 is selected from lower alkyl, hydroxyl, and amino;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 2. A compound of claim 1 wherein R.sup.1 is selected from hydroxyl, amino, lower alkyl, lower carboxyalkyl, lower alkoxycarbonyl, aminocarbonyl, carboxyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower alkoxy, lower haloalkoxy, lower aralkoxy, lower cycloalkylalkoxy, lower alkylthio, lower aralkylthio, lower cycloalkylalkylthio, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower hydroxyalkyl, lower haloalkyl, lower cycloalkyl, lower cycloalkylalkyl, lower aralkyl, halo, lower alkylamino, lower aralkylamino, lower N-alkyl-N-aralkylamino, lower N-alkyl-N-cycloalkylalkylamino, lower arylcarbonyloxyalkyl, lower alkoxycarbonyloxyalkyl, lower alkylaminocarbonyloxyalkyl, lower alkoxycarbonylthioalkyl, and lower alkylaminocarbonylthioalkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, lower alkylsulfonyl, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 3. A compound of claim 2 wherein R.sup.1 is selected from hydroxyl, lower alkyl, carboxyl, lower carboxyalkyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower aralkyl, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower haloalkyl, lower hydroxylalkyl, cycloalkyl, cycloalkylalkyl, and aralkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4. A compound of claim 3 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected form benzyl and phenylethyl, wherein the phenyl ring is optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, aminosulfonyl, methylthio, ethylthio, butylthio, and hexylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 5. The compound of claim 4 which is 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 6. A compound of Formula III ##STR33## wherein R.sup.1 is selected from hydroxyl, alkyl, carboxyalkyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl; and
– Name: Comment
  Label: Claim
  Group: Patent
  Data: wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, hydroxyalkyl, haloalkoxy, amino, alkylamino, arylamino, aminoalkyl, nitro, alkoxyalkyl, alkylsulfinyl, aminosulfonyl, halo, alkoxy and alkylthio; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 7. A compound of claim 6 wherein R.sup.1 is selected from hydroxyl, lower alkyl, carboxyl, lower carboxyalkyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower aralkyl, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower haloalkyl, lower hydroxylalkyl, lower cycloalkyl, lower cycloalkylalkyl, and aralkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; and wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, aminosulfonyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy and lower alkylthio; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 8. A compound of claim 7 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected from phenylethyl and benzyl optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; and wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, aminomethyl, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, methylthio, aminosulfonyl, ethylthio, butylthio, and hexylthio; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 9. A pharmaceutical composition comprising a therapeutically-effective amount of a compound, said compound selected from a family of compounds of Formula II ##STR34## wherein R.sup.1 is selected from alkyl, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyl, amino, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 10. A pharmaceutical composition of claim 9 wherein R.sup.1 is selected from hydroxyl, amino, lower alkyl, lower carboxyalkyl, lower alkoxycarbonyl, aminocarbonyl, carboxyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower alkoxy, lower haloalkoxy, lower aralkoxy, lower cycloalkylalkoxy, lower alkylthio, lower aralkylthio, lower cycloalkylalkylthio, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower hydroxyalkyl, lower haloalkyl, lower cycloalkyl, lower cycloalkylalkyl, lower aralkyl, halo, lower alkylamino, lower aralkylamino, lower N-alkyl-N-aralkylamino, lower N-alkyl-N-cycloalkylalkylamino, lower arylcarbonyloxyalkyl, lower alkoxycarbonyloxyalkyl, lower alkylaminocarbonyloxyalkyl, lower alkoxycarbonylthioalkyl, and lower alkylaminocarbonylthioalkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, lower alkylsulfonyl, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 11. A pharmaceutical composition of claim 10 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected form benzyl and phenylethyl, wherein the phenyl ring is optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, aminosulfonyl, methylthio, ethylthio, butylthio, and hexylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 12. A pharmaceutical composition of claim 11 wherein said compound is 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 13. A pharmaceutical composition comprising a therapeutically-effective amount of a compound, said compound selected from a family of compounds of Formula III ##STR35## wherein R.sup.1 is selected from hydroxyl, alkyl, carboxyalkyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl; and
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 14. A method of treating inflammation or an inflammation-associated disorder in a subject, said method comprising administering to the subject having or susceptible to said inflammation or inflammation-associated disorder, a therapeutically-effective amount of a compound of Formula II ##STR36## wherein R.sup.1 is selected from alkyl, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyl, amino, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 15. A method of claim 14 wherein R.sup.1 is selected from hydroxyl, amino, lower alkyl, lower carboxyalkyl, lower alkoxycarbonyl, aminocarbonyl, carboxyl, lower aminocarbonylalkyl, lower alkoxycarbonylalkyl, lower alkoxy, lower haloalkoxy, lower aralkoxy, lower cycloalkylalkoxy, lower alkylthio, lower aralkylthio, lower cycloalkylalkylthio, lower alkoxyalkyl, lower aralkoxyalkyl, lower alkylthioalkyl, lower aralkylthioalkyl, lower alkylaminoalkyl, lower aryloxyalkyl, lower arylthioalkyl, lower hydroxyalkyl, lower haloalkyl, lower cycloalkyl, lower cycloalkylalkyl, lower aralkyl, halo, lower alkylamino, lower aralkylamino, lower N-alkyl-N-aralkylamino, lower N-alkyl-N-cycloalkylalkylamino, lower arylcarbonyloxyalkyl, lower alkoxycarbonyloxyalkyl, lower alkylaminocarbonyloxyalkyl, lower alkoxycarbonylthioalkyl, and lower alkylaminocarbonylthioalkyl; wherein R.sup.3 is selected from cycloalkyl, cycloalkenyl, and aryl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, lower alkylsulfonyl, aminosulfonyl, and lower alkylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 16. A method of claim 15 wherein R.sup.1 is selected from hydroxyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, neopentyl, hexyl, carboxyl, carboxypropyl, carboxymethyl, carboxyethyl, benzyl, phenethyl, aminocarbonylmethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxymethyl, benzyloxymethyl, phenylethoxymethyl, methylthiomethyl, benzylthiomethyl, N-methylaminomethyl, N,N-dimethylaminomethyl, phenyloxymethyl, phenylthiomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxylmethyl, hydroxylpropyl, hydroxylethyl, cyclohexyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexylmethyl, cyclohexylethyl, cyclobutylethyl, cyclopentylmethyl, cycloheptylpropyl, and lower aralkyl selected form benzyl and phenylethyl, wherein the phenyl ring is optionally substituted at a substitutable position with fluoro, chloro, bromo, iodo, methyl, and methoxy; wherein R.sup.3 is selected from phenyl, naphthyl, biphenyl, cyclohexyl, cyclopentyl, cycloheptyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 4-cyclohexenyl, and 1-cyclopentenyl; wherein R.sup.3 is optionally substituted at a substitutable position with one or more radicals independently selected from trifluoromethoxy, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-dipropylamino, N-butylamino, N-methyl-N-ethylamino, phenylamino, N-methyl-N-phenylamino, methylsulfinyl, ethylsulfinyl, methyl, ethyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, hexyl, cyano, carboxyl, methoxycarbonyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, fluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, hydroxyl, hydroxymethyl, amino, nitro, fluoro, chloro, bromo, iodo, methoxy, ethoxy, propoxy, n-butoxy, pentoxy, hexyloxy, methylenedioxy, aminosulfonyl, methylthio, ethylthio, butylthio, and hexylthio; and wherein R.sup.4 is selected from methyl, hydroxyl and amino; or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 17. A method of claim 16 wherein said compound is 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 18. A method of treating inflammation or an inflammation-associated disorder in a subject, said method comprising administering to the subject having or susceptible to said inflammation or inflammation-associated disorder, a therapeutically-effective amount of a compound of Formula III ##STR37## wherein R.sup.1 is selected from hydroxyl, alkyl, carboxyalkyl, aminocarbonylalkyl, alkoxycarbonylalkyl, carboxyl, alkoxy, haloalkoxy, aralkoxy, cycloalkylalkoxy, alkylthio, aralkylthio, cycloalkylalkylthio, alkoxyalkyl, aralkoxyalkyl, alkylthioalkyl, aralkylthioalkyl, alkylaminoalkyl, aryloxyalkyl, arylthioalkyl, hydroxyalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aralkyl, halo, alkylamino, aralkylamino, N-alkyl-N-aralkylamino, N-alkyl-N-cycloalkylalkylamino, arylcarbonyloxyalkyl, arylcarbonylthio, alkoxycarbonyloxyalkyl, alkylaminocarbonyloxyalkyl, alkoxycarbonylthioalkyl, and alkylaminocarbonylthioalkyl; and
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 19. A method of claim 14 for use in treatment of inflammation.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 20. A method of claim 14 for use in treatment of an inflammation-associated disorder.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 21. A method of claim 20 wherein the inflammation-associated disorder is arthritis.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 22. A method of claim 20 wherein the inflammation-associated disorder is pain.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 23. A method of claim 20 wherein the inflammation-associated disorder is fever.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 24. The compound of claim 4 selected from compounds, or their pharmaceutically acceptable salts, of the group consisting of
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-ethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-propyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-isopropyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-butyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-isobutyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-cyclohexyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-neopentyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-cyclohexylmethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-(4-chlorophenyl)methyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-trifluoromethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-difluoromethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-chloromethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-methyl-3-phenylisoxazol-4-yl]benzenesulfonic acid;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-propyl-3-phenylisoxazol-4-yl]benzenesulfonic acid;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-methoxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-3-hydroxypropyl)-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-4-chlorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-4-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-3-fluoro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-3-aminosulfonyl-4-methoxyphenyl)-5-methyl-isoxazol-4-yl]benzenesulfona mide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-3-chloro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-3-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]carboxylic acid;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-hydroxy-3-phenyl-4-isoxazolyl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-methyl-5-phenyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-methyl-3-phenyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-(3-fluoro-4-methoxyphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: [3-(3-chloro-4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]isoxazol-5-yl]ace tic acid;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 5-methyl-4-[4-(methylsulfonyl)phenyl]-3-phenyl-isoxazole;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 3-(3-chloro-4-methoxyphenyl)-5-methyl-4-[4-(methylsulfonyl)phenyl]isoxazole
– Name: Comment
  Label: Claim
  Group: Patent
  Data: [4-[4-(aminosulfonyl)phenyl]-3-phenyl-isoxazol-5-yl]acetic acid;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: [4-[4-(aminosulfonyl)phenyl]-3-phenyl-isoxazol-5-yl]propanoic acid;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: ethyl [4-[4-(aminosulfonyl)phenyl]-3-phenyl-isoxazol-5-yl]propanoate;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: [3-(3-fluoro-4-methoxyphenyl)-4-[4-(methylsulfonyl)phenyl]isoxazol-5-yl]ace tic acid; and
– Name: Comment
  Label: Claim
  Group: Patent
  Data: [4-[4-(aminosulfonyl)phenyl]-3-(3-fluoro-4-methoxyphenyl)isoxazol-5-yl]prop anoic acid.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 25. The compound of claim 4 which is 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 26. A pharmaceutical composition of claim 11 wherein said compound is selected from compounds, or their pharmaceutically-acceptable salts, of the group consisting of
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 3-(3-chloro-4-methoxyphenyl)-5-methyl-4-[4-(methylsulfonyl)phenyl]isoxazole ;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 27. A pharmaceutical composition of claim 11 wherein said compound is 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 28. A method of claim 16 wherein said compound is selected from compounds, or their pharmaceutically-acceptable salts, of the group consisting of
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5isopropyl-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[5-(3-hydroxypropyl)-3-phenylisoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-(4-chlorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-(4-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-(3-fluoro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-(3-aminosulfonyl-4-methoxyphenyl)-5-methyl-isoxazol-4-yl]benzenesulfon amide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-(3-chloro-4-methylphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 4-[3-(3-fluorophenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide;
– Name: Comment
  Label: Claim
  Group: Patent
  Data: 29. A method of claim 16 wherein said compound is 4-[5-hydroxymethyl-3-phenylisoxazol-4-yl]benzenesulfonamide, or a pharmaceutically-acceptable salt thereof.
– Name: CodeClass
  Label: Current U.S. Class
  Group: Patent
  Data: 514/378; 548/182; 548/186; 548/190; 548/193; 548/202; 548/203; 548/225; 548/228; 548/229; 548/232; 548/234; 548/235; 548/243; 548/245; 548/247; 548/248; 5462/721; 544/405; 514/255; 514/340; 514/365; 514/369; 514/370; 514/374; 514/376; 514/377; 514/380
– Name: CodeClass
  Label: Current International Class
  Group: Patent
  Data: C07D26106; C07D26110; C07D26112; C07D26114; A61K 3142
– Name: Ref
  Label: Patent References Cited
  Group: Patent
  Data: <searchLink fieldCode="RF" term="%225310926%22">5310926</searchLink> May 1994 Hagiwara et al.<br /><searchLink fieldCode="RF" term="%225318970%22">5318970</searchLink> June 1994 Suzuki et al.
– Name: Ref
  Label: Other References
  Group: Patent
  Data: Ichiro Yamawaki et al, Chem. Pharm. Bull., 36:3142-3146 @(1988).<br />Umezawa et al, Bull. Chem. Soc. Jpn vol. 36, No. 9, pp. 1150-1154 Sep. (1963).<br />Descamps et al, Bull. Soc. Chim. Belg., 73:459-82 (1964).<br />Hagiwara et al. CA 114:42776k, @1991.<br />Nagai et al., CA 117:212485w, @1992.
– Name: AuthorEditor
  Label: Primary Examiner
  Group: Patent
  Data: <searchLink fieldCode="ZE" term="%22Richter%2C+Johann%22">Richter, Johann</searchLink>
– Name: AuthorEditor
  Label: Assistant Examiner
  Group: Patent
  Data: <searchLink fieldCode="ZE" term="%22Stockton%2C+Laura+L%2E%22">Stockton, Laura L.</searchLink>
– Name: AuthorCorporate
  Label: Attorney, Agent or Firm
  Group: Patent
  Data: <searchLink fieldCode="ZG" term="%22Bulock%2C+Joseph+W%2E%22">Bulock, Joseph W.</searchLink>
– Name: AN
  Label: Accession Number
  Group: ID
  Data: edspgr.05633272
PLink https://login.libproxy.scu.edu/login?url=https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&scope=site&db=edspgr&AN=edspgr.05633272
RecordInfo BibRecord:
  BibEntity:
    Languages:
      – Text: English
    Titles:
      – TitleFull: Substituted isoxazoles for the treatment of inflammation
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Talley, John J.
      – PersonEntity:
          Name:
            NameFull: Brown, David L.
      – PersonEntity:
          Name:
            NameFull: Nagarajan, Srinivasan
      – PersonEntity:
          Name:
            NameFull: Carter, Jeffery S.
      – PersonEntity:
          Name:
            NameFull: Weier, Richard M.
      – PersonEntity:
          Name:
            NameFull: Stealey, Michael A.
      – PersonEntity:
          Name:
            NameFull: Collins, Paul W.
      – PersonEntity:
          Name:
            NameFull: Rogers, deceased, Roland S.
      – PersonEntity:
          Name:
            NameFull: Seibert, Karen
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 27
              M: 05
              Text: May 27, 1997
              Type: published
              Y: 1997
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