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United States Patent (19) L L 3,933,802 Ferrini Et Al

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United States Patent (19) L L 3,933,802 Ferrini Et Al United States Patent (19) l l 3,933,802 Ferrini et al. (45) Jan. 20, 1976 54 SULPHAMOYLBENZOIC ACID AMDES Primary Examiner-Sam Rosen Assistant Examiner-D. W. Robinson (75) Inventors: Pier Giorgio Ferrini, Binningen; Attorney, Agent, or Firm-Joseph G. Kolodny, John J. Georges Haas; Alberto Rossi, both of Oberwil, all of Switzerland Maitner; Theodore O. Groeger 73) Assignee: Ciba-Geigy Corporation, Ardsley, 57 ABSTRACT N.Y. New 2-amino-5-sulphamoylbenzoic acid amide of the (22 Filed: May 22, 1974 general formula (21) Appl. No.: 472,333 (30) Foreign Application Priority Data May 28, 1973 Switzerland......................... 7643/73 Apr. 1, 1974 Switzerland......................... 4507174 (52) U.S. Cl............................... 260/239.7; 424/229 5 Int. Cl.............. C07D 237/00; C07D 239/00; C07D 241/00; CO7D 251/00 58) Field of Search......... 260/239.6, 239.7, 239.75, 260/239.65; 424/229 wherein R. denotes lower alkyl, R, denotes hydrogen, halogen, trifluoromethyl, lower alkyl or lower alkoxy, 56) References Cited Ra denotes hydrogen, hydroxyl or lower alkyl, R. de UNITED STATES PATENTS notes acyl and alk denotes lower 1,2-alkylene or 1,3- 2,910,488 0/959 Novello............................ 260f239.6 alkylene or a therapeutically acceptable acid addition 3,444,177 5/1969 Schmidt et al................... 260/239.7 salt thereof are usefull as mild analgesics with an anti FOREIGN PATENTS OR APPLICATIONS inflammatory component of action. 2,598 M 511963 France............................. 260f239.6 16 Claims, No Drawings 2,001,158 7|1970 Germany 3,933,802 1. and especially: butylene-1,2,w 2 propylene-1,2 and ethyl ene should be mentioned as examples. NEW SULPHAMOYLBENZOIC ACID AMIDEs The new 2-amino-5-sulphamoylbenzoic acid amides The invention relates to new 2-amino-5-sulphamoyl possess valuable pharmacological properties. Thus they benzoic acid amides of the general formula 5 exhibit, in particular, a distict anti-inflammatory ac tion, as can be shown, for example, in the turpentine pleuritis test on rats on peroral adminsitration of a dose of 10 to 300 mg/kg in each case, and above all a distinct antinociceptive (analgesic) action, as can be shown, for O example, in the acetic acid writhing test on mice on peroral administration of a dose of 100 to 300 mg/kg in each case. They are also distinguished by a compara tively low toxicity, as can be shown, for example, on peroral administration to rats. The new 2-amino-5-sul 15 phamoylbenzoic acid amides therefore are usefull as mild analgesics with an anti-inflammatory component (I) of action. The invention relates above all to those 2-amino-5- sulphamoylbenzoic acid amides of the formula wherein R. denotes identical lower alkyl groups with l to 4 C atoms, such as methyl or ethyl, R. denotes hy drogen, lower alkyl or lower alkoxy with up to 4 carbon atoms, or halogen up to atomic number 17, such as fluorine or chlorine, Ra denotes hydrogen, hydroxyl or 25 lower alkyl with 1 to 4 C atoms, such as isopropyl, n-propyl or above all ethyl or methyl, R. denotes a wherein R. denotes lower alkyl, R. denotes hydrogen, group of the formula -COOR' or -COR' wherein R' halogen, trifluoromethyl, lower alkyl or lower alkoxy, denotes lower alkyl with 1 to 4 C atoms, such as isobu R. denotes hydrogen, hydroxyl or lower alkyl, R. de tyl, n-butyl, isopropyl, n-propyl, ethyl or methyl, lower notes acyl and alk denotes lower 1,2-alkylene or 1,3- 30 alkenyl with 3 or 4C atoms, such as allyl or methallyl, alkylene, and processes for their manufacture. or phenyl, benzyl or phenylethyl which is optionally The radicals R and alk can in each case be identical monosubstituted or disubstituted in the phenyl part by or different. lower alkyl or lower alkoxy with 1 to 4 C atoms in each Lower alkyl R, R and R contains in particular 1 to case, such as methyl or methoxy, halogen up to atomic 7 C atoms, above all 1 to 4 C atoms, and is therefore in 35 number 17, such as chlorine, or nitro, and alk denotes particular heptyl, hexyl or pentyl, which can be 1,2-alkylene with 2-4C atoms, such as butylene-2,3 or straight-chain or branched and linked in any position, above all butylene-1,2, propylene-1,2 or ethylene. or, above all, n-butyl, sec.-butyl, tert.-butyl, isobutyl, However, the invention relates particularly to those isopropyl or n-propyl or especially ethyl or methyl. 5-sulphamoylanthranilic acid amides of the formula I Halogen R, is in particular fluorine, bromine or 40 wherein R is methyl, R, is chlorine, methoxy, methyl above all chlorine. or above all hydrogen, R is hydrogen or lower alkyl Lower alkoxy R contains in particular 1 to 7 C with 1 to 4 C atoms, such as ethyl or methyl, R. denotes atoms, above all to 4 C atoms, and is therefore in a group of the formula -COOR' or -COR' wherein particular heptyloxy, hexyloxy or pentoxy, which can R is lower alkyl with 1 to 4 C atoms, such as isobutyl, be straight chain or branched and linked in any posi 45 n-butyl, isopropyl, n-propyl, ethyl or methyl, lower tion, or above all n-butoxy, sec.-butoxy, tert-butoxy, alkenyl with 3 or 4C atoms, such as allyl or methallyl, isobutoxy, isopropoxy or n-propoxy, ethoxy or me or phenyl, benzyl or phenylethyl which is optionally thoxy. monosubstituted or disubstituted in the phenyl part by Acyl R is in particular acyl of the formula -COR or lower alkyl or lower alkoxy with 1 to 4C atoms in each -COOR wherein R. denotes lower alkyl, lower alkenyl 50 case, such as methyl or methoxy, halogen up to atomic or aryl-lower alkyl. - number 17, such as chlorine, or nitro, and alk denotes Lower alkyl R contains in particular 1 to 7C atoms, 1,2-alkylene with 2 to 4 C atoms, such as butylene-2,3, above all 1 to 4 C atoms, and is above all one of the butylene-1,2, propylene-1,2 or above all ethylene. lower alkyl groups mentioned for R, R and R. The invention relates very particularly, however, to Lower alkenyl R contains in particular 2 to 4 C 55 those of the abovementioned 5-sulphamoylanthranilic atoms, above all 3 or 4C atoms, and is especially allyl acid amides of the formula I wherein R is methyl, R is or methallyl. hydrogen, Rs is hydrogen, ethyl or methyl, R is a group Aryl-lower alkyl R is in particular phenyl-lower alkyl of the formula -COOR' or -COR'" wherein R' with 1 to 4 C atoms in the alkyl part, which is optionally denotes lower alkyl with 1 to 4 C atoms, allyl, phenyl or substituted in the phenyl part by lower alkyl, lower 50 benzyl which is optionally nitrated, for example in the alkoxy, halogen, trifluoromethyl and/or nitro, above all p-position, and alk is propylene-1,2 or above all ethyl benzyl ar phenylethyl which are optionally substituted e. as indicated. The invention relates especially, however, to those of The radicals alk can be straight-chain or branched the abovementioned 5-sulphamoylanthranilic acid am and can contain, where appropriate, 1 to 7 C atoms, 65 ides of the formula I wherein R is methyl, R is hydro particularly 1 to 4 C atoms, in the side chain. 3-Methyl gen, Rs is hydrogen or ethyl, R is a group of the for butylene-1,3 and isobutylene-1,3 and above allisobuty mula -COOR' wherein R' denotes lower alkyl with 1 lene-1,2, butylene-2,3 and particularly propylene-1,3 to 4 C atoms, allyl or benzyl which is optionally ni 3,933,802 3 4 trated, especially in the p-position, and alk is ethylene, However, it is also possible to prepare the new 2 wherein 1-(5-(dimethylsulphamoyl)-anthraniloyl)-4- amino-5-sulphamoylbenzoic acid amides by reacting a ethoxycarbonylpiperazine in particular should be sin 5-sulphamoylisatoic acid anhydride of the formula IIIa gled out. The new 2-amino-5-sulphamoylbenzoic acid amides can be obtained by processes which are in themselves known. Thus, for example, it is possible to prepare 2-amino 5-sulphamoylbenzoic acid amides of the formula I wherein R is hydrogen or hydroxy, by reducing the 10 O O O. nitro group in a 2-nitro-5-sulphamoylbenzoic acid N 2 amide of the formula II R NR; (IIIa) 5 l No. R R2 20 Y N. CO-N N-R Yank^ ( R NO II) N-OS wherein R and R, have the indicated meanings and Y 2 Rs' denotes hydrogen or lower alkyl, with an amine of R R2 the formula IV 30 (W) wherein alk and R have the indicated meanings to yield an optionally N-lower alkylated 5-sulphamoylan wherein R, R, R and alk have the indicated mean 35 thranilic acid amide. ings. The reaction with the amine of the formula IV can be The reduction of the nitro group can be carried out in carried out in a manner which is in itself known, if a manner which is in itself known and particularly in a necessary in the presence of a solvent and/or a conden manner which is described for analogous reactions, sation agent, especially a basic condensation agent, and such as by means of nascent hydrogen, produced, for 40 advantageously at an elevated temperature. example, by the action of a strong acid, such as a hy In resulting 2-amino-5-sulphamoylbenzoic acid am drogen halide acid, above all hydrochloric acid, or ides, substituents can be introduced, modified and split sulphuric acid or a lower aliphatic carboxylic acid, such off within the scope of the definition of the end prod as acetic acid, on base metals, such as iron, zinc, mag ucts.
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