N-alkenyl-3-hydroxybenzo[b]thiophene-2-carboxamide derivatives as dual cyclooxygenase and lipoxygenase inhibitors
US4760086A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Feb 27, 1985 |
| Grant date | Jul 26, 1988 |
| Priority date | — |
| Expiry date | Feb 27, 2005 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D333/70
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
N-Alkenyl-3-hydroxybenzo[b]thiophene-2-carboxamide derivatives have been prepared by: PA0 (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; PA0 (2) treating a substituted thiosalicylate with an appropriately substituted haloacetamide, followed by dehydration; and PA0 (3) further synthetic modification of compounds prepared above. 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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.