N-alkenyl-3-hydroxybenzo¬b|thiophene-2- carboxamide...

C - Chemistry – Metallurgy – 07 – D

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C07D 333/70 (2006.01) A61K 31/38 (2006.01) C07C 63/70 (2006.01) C07D 303/04 (2006.01) C07D 409/00 (2006.01) C07D 409/12 (2006.01)

Patent

CA 1298837

1737M/0677A 17023IA TITLE OF THE INVENTION N-ALKENYL-3-HYDROXYBENZO[b]THIOPHENE- 2-CARBOXAMIDE DERIVATIVES AS DUAL CYCLOOXYGENASE AND LIPOXYGENASE INHIBITORS ABSTRACT OF THE DISCLOSURE N-Alkenyl-3-hydroxybenzo[b]thiophene-2- carboxamide derivatives have been prepared by: 1) treating a substituted 2-halobenzoate with thioacetamide followed by N-alkenylation with appropriate agents, such as aldehydes, ketones, enol ethers, epoxides, acetals or ketals; 2) treating a substituted thiosalicylate with an appropriately substituted haloacetamide, followed by dehydration; and 3) further synthetic modification of compounds prepared above. 1737M/0677A - 2 - 17023IA These compounds have been found to be effective inhibitors of both cyclooxygenase and lipoxygenase and thereby useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory bowel disease, glaucoma or other prostaglandins and/or leukotriene mediated diseases. Furthermore, these compounds have been found to exhibit cytoprotective activity which does not involve the inhibition of gastric acid secretion but can be used at relatively low dosages for increasing the resistance of gastro-intestinal mucosa to strong irritants.

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