Details for Patent: 6,156,781
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| Title: | Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation |
| Abstract: | A class of pyrazolyl benzenesulfonamide 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.2 is selected from hydrido, alkyl, haloalkyl, alkoxycarbonyl, cyano, cyanoalkyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, carboxyalkylaminocarbonyl, carboxyalkyl, aralkoxycarbonylalkylaminocarbonyl, aminocarbonylalkyl, alkoxycarbonylcyanoalkenyl and hydroxyalkyl; wherein R.sup.3 is selected from hydrido, alkyl, cyano, hydroxyalkyl, cycloalkyl, alkylsulfonyl and halo; and wherein R.sup.4 is selected from aralkenyl, aryl, cycloalkyl, cycloalkenyl and heterocyclic; wherein R.sup.4 is optionally substituted at a substitutable position with one or more radicals selected from halo, alkylthio, alkylsulfonyl, cyano, nitro, haloalkyl, alkyl, hydroxyl, alkenyl, hydroxyalkyl, carboxyl, cycloalkyl, alkylamino, dialkylamino, alkoxycarbonyl, aminocarbonyl, alkoxy, haloalkoxy, sulfamyl, heterocyclic and amino; provided R.sup.2 and R.sup.3 are not both hydrido; further provided that R.sup.2 is not carboxyl or methyl when R.sup.3 is hydrido and when R.sup.4 is phenyl; further provided that R.sup.4 is not triazolyl when R.sup.2 is methyl; further provided that R.sup.4 is not aralkenyl when R.sup.2 is carboxyl, aminocarbonyl or ethoxycarbonyl; further provided that R.sup.4 is not phenyl when R.sup.2 is methyl and R.sup.3 is carboxyl; and further provided that R.sup.4 is not unsubstituted thienyl when R.sup.2 is trifluoromethyl; or a pharmaceutically-acceptable salt thereof. |
| Inventor(s): | Talley; John J (St. Louis, MO), Penning; Thomas D (Elmhurst, IL), Collins; Paul W (Deerfield, IL), Rogier, Jr.; Donald J (St. Louis, MO), Malecha; James W (Libertyville, IL), Miyashiro; Julie M (Chicago, IL), Bertenshaw; Stephen R (Brentwood, MO), Khanna; Ish K (Vernon Hills, IL), Graneto; Matthew J (St. Louis, MO), Rogers; Roland S (Richmond Heights, MO), Carter; Jeffery S (Chesterfield, MO), Docter; Stephen H. (Mt. Prospect, IL), Yu; Stella S (Morton Grove, IL) |
| Assignee: | G. D. Searle & Co. (Skokie, IL) |
| Filing Date: | Nov 24, 1999 |
| Application Number: | 09/449,076 |
| Claims: | 1. A method of treating an inflammation-associated skin-related condition in a subject, said method comprising administering to the subject having said condition, a therapeutically-effective amount of a compound selected from compounds, and their pharmaceutically acceptable salts, of the group consisting of 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e; 4-[5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide 4-[5-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e; 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e; 4-[5-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e; 4-[5-(2-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e; 4-[5-(4-trifluoromethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenes ulfonamide; 4-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e; 4-[5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide; 4-[5-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonami de; 4-[5-(4-trifluoromethoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene sulfonamide; 4-[5-(2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e; 4-[5-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide ; 4-[5-(4-aminophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide ; 4-[5-(4-chlorophenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide ; 4-[5-(4-[methylthio]phenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfo namide; 4-[5-(2,4-[difluoro]phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulf onamide; 4-[5-(2,6-[difluoro]phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulf onamide; -[5-(4-chlorophenyl)-3-(heptafluoropropyl)-1H-pyrazol-1-yl]benzenesulfonami de; 4-[5-(4-chlorophenyl)-3-(chloro-difluoromethyl)-1H-pyrazol-1-yl]benzenesulf onamide; 4-[5-(4-chlorophenyl)-3-(pentafluoroethyl)-1H-pyrazol-1-yl]benzenesulfonami de; 4-[5-(4-biphenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide; 4-[5-(4-(morpholino)phenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfo namide; 4-[5-(1-cyclohexenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide ; 4-[5-(1-cyclohexyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide; 4-[5-(4-[trifluoromethyl]phenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzene sulfonamide; 4-[5-(3,4-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfon amide; and 4-[5-(2,4-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfon amide. 2. The method of claim 1 where the compound is 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonami de, or a pharmaceutically-acceptable salt thereof. 3. The method of claim 1 where the compound is 4-[5-(4-chlorophenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e, or a pharmaceutically-acceptable salt thereof. 4. The method of claim 1 where the compound is 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonami de, or a pharmaceutically-acceptable salt thereof. 5. The method of claim 1 wherein the condition is selected from psoriasis, eczema, burns and dermatitis. 6. The method of claim 1 wherein the condition is a burn. 7. The method of claim 1 wherein the condition is dermatitis. 8. The method of claim 1 wherein the condition is psoriasis. |
