Anthranilates Fenamic Acid Derivatives

Tolfenamic Acid. 2-[(3-Chioro-2.methylphenyl)-aminojbenzoic acid V-(3-clj loro f-totyl >anthranilic acid JV-C2-methyl-3-chlorophenyl)anthranilic acid GEA 6414 Clotam Tolfedine. CMHuCINO, mol wt 261.71. C 64.25%, H 4.62%, Cl 13.55%, N 5.35%, O 12.23%, Deriv of anthranilic acid, related structurally to merenamic and flu-fenamic acids, q.q. v. Prepn Neth. pat. Appl, 6,680,251... 

Flufenamic acid (162) is a reasonably well-established NSAID (Non Steroidal Anti Inflammatory Drug). Alkylation of its potassiuni salt with the hydroxyethyl ethyl ether of ethylenechlo-rohydrin affords the latendated derivative etofenamate (163) [41]. Antiinflammatory activity is apparently retained when both rings in the fenamate series carry carboxyl groups. Thus, condensation of dichlorobenzoic acid 164 with anthranilic acid (165) by means of nucleophilic aromatic... 

These agents are considered to be 7/-aryl-substituted derivatives of anthranilic acid, which itself is a bioisostere of salicylic acid. These agents retain the acidic properties that are characteristic of this class of agents though mefenamic acid and meclofenamic acid are derivatives of anthranilic acid, diclofenac is derived from 2-arylacetic acid (Figure 13.10). The most active fenamates have small alkyl or halogen substituents at the 2, 3, or 6 position of the iV-aryl moiety... 

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