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Literature DB >> 7086815

Isoxicam and related 4-hydroxy-N-isoxazolyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides. Potent nonsteroidal antiinflammatory agents.

H Zinnes, J C Sircar, N Lindo, M L Schwartz, A C Fabian, J Shavel, C F Kasulanis, J D Genzer, C Lutomski, G DiPasquale.

Abstract

A novel series of antiinflammatory agents, N-isoxazolyl-3-carboxamides of 4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide, was synthesized and evaluated as antiinflammatory agents in the carrageenin-induced rat paw edema (CIRPE) assay and adjuvant-induced polyarthritis (AIP) assay. Several analogues were found to be equipotent or more potent than aspirin and phenylbutazone. Structure-activity relationships are discussed. One of the compounds, 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine 3-carboxamide 1,1-dioxide (3a; isoxicam), was found to be 3 times as potent as phenylbutazone in the CIRPE and in the therapeutic AIP assays. Isoxicam (3a) is presently undergoing phase III clinical trial as an antiarthritic drug.

Entities: Chemical Disease Species

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Year: 1982 PMID： 7086815 DOI： 10.1021/jm00343a003

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

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Cited

6 in total

6. Solvent-free synthesis of 3,5-isoxazoles via 1,3-dipolar cycloaddition of terminal alkynes and hydroxyimidoyl chlorides over Cu/Al₂O₃ surface under ball-milling conditions.

Authors: Rafael A Hernandez R; Kelly Burchell-Reyes; Arthur P C A Braga; Jennifer Keough Lopez; Pat Forgione
Journal: RSC Adv Date: 2022-02-23 Impact factor: 3.361

6 in total

Isoxicam and related 4-hydroxy-N-isoxazolyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides. Potent nonsteroidal antiinflammatory agents.

1. Effect of impairment of renal function on the accumulation and disposition of isoxicam.

2. A modified mouse air pouch model for evaluating the effects of compounds on granuloma induced cartilage degradation.

3. N-Butyl-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

4. 4-Hy-droxy-3-(3-meth-oxybenzoyl)-2-[(3-meth-oxybenzoyl)methyl]-2H-1,2-benzothia-zine 1,1-dioxide.

5. 4-Hy-droxy-2-[(4-iodo-benzo-yl)meth-yl]-3-(3-meth-oxy-benzo-yl)-2H-1,2-benzothia-zine 1,1-dioxide.

6. Solvent-free synthesis of 3,5-isoxazoles via 1,3-dipolar cycloaddition of terminal alkynes and hydroxyimidoyl chlorides over Cu/Al₂O₃ surface under ball-milling conditions.

Isoxicam and related 4-hydroxy-N-isoxazolyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides. Potent nonsteroidal antiinflammatory agents.

1. Effect of impairment of renal function on the accumulation and disposition of isoxicam.

2. A modified mouse air pouch model for evaluating the effects of compounds on granuloma induced cartilage degradation.

3. N-Butyl-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

4. 4-Hy-droxy-3-(3-meth-oxybenzoyl)-2-[(3-meth-oxybenzoyl)methyl]-2H-1,2-benzothia-zine 1,1-dioxide.

5. 4-Hy-droxy-2-[(4-iodo-benzo-yl)meth-yl]-3-(3-meth-oxy-benzo-yl)-2H-1,2-benzothia-zine 1,1-dioxide.

6. Solvent-free synthesis of 3,5-isoxazoles via 1,3-dipolar cycloaddition of terminal alkynes and hydroxyimidoyl chlorides over Cu/Al2O3 surface under ball-milling conditions.

6. Solvent-free synthesis of 3,5-isoxazoles via 1,3-dipolar cycloaddition of terminal alkynes and hydroxyimidoyl chlorides over Cu/Al₂O₃ surface under ball-milling conditions.