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Details for Patent: 6,586,603

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Details for Patent: 6,586,603

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. (Chicago, IL)
Filing Date:Oct 21, 2002
Application Number:10/274,679
Claims:1. A method for the preparation of 4-[5-(4-chlorophenyl)-3-trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamid e wherein the method comprises: contacting ethyl trifluoroacetate with 4-chloroacetophenone in the presence of sodium methoxide and an ether solvent to form 4,4,4-trifluoro-1-[4-(chloro)phenyl]-butane-1,3-dione; and contacting the 4,4,4-trifluoro-1-[4-(chloro)phenyl]-butane-1,3-dione with 4-sulphonamidophenyl hydrazine hydrochloride in the presence of absolute ethyl alcohol under reflux to produce 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonami de.
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