N-substituted fused-heterocyclic carboxamide derivatives as dual

Details N-substituted fused-heterocyclic carboxamide derivatives as dual N-substituted fused-heterocyclic carboxamide derivatives as dual

1985-08-02

1988-01-19

Siegel, Alan

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514470, 549 50, 549464, A61K 3138, A61K 3134, C07D49502, C07D49300

Patent

active

047205032

ABSTRACT:
N-substituted fused-heterocyclic carboxamide derivatives, for example, N-(2,2-diphenylethenyl)-3-hydroxythieno[3,2-b]thiophene-2-carboxamide can be prepared by ring closure between an appropriately substituted halo-thiophene ester, e.g., methyl 3-bromo-thiophene-2-carboxylate, and mercaptoacetamide followed by condensation with diphenylacetaldehyde. Alternatively, the ring closure can be carried out between an appropriately substituted mercaptothiophene ester, e.g., methyl 3-mercaptothiophene-2-carboxylate and a haloacetamide to afford the fused-heterocyclic intermediate, 3-hydroxythieno[3,2-b]thiophene-2-carboxamide. N-alkenylation of the intermediate will then lead to the final products.
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, eye inflammation caused by glaucoma or other eye diseases, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory bowel disease, or other prostaglandin and/or leukotriene mediated diseases.

REFERENCES:
patent: 3706810 (1972-12-01), Brabander
patent: 3733322 (1973-05-01), Wright
patent: 3745174 (1973-07-01), Thominet
patent: 4396621 (1983-08-01), Berngsconi et al.
patent: 4663344 (1987-05-01), Durette et al.

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