3-Benzoylfluoro-methanesulfonanilides

Abstract

Benzoylhaloalkanesulfonanilides of the general type ##SPC1## Wherein R x is a haloalkyl group having up to four carbon atoms and at least one halogen atom bonded to the alpha carbon atom or if there is no halogen bonded to said alpha carbon atom, having at least 2 halogen atoms bonded to the beta carbon atom, R is hydrogen, alkyl or alkenyl containing not more than three carbon atoms, or a pharmaceutically acceptable cation; each Y .Iadd.and Y' .Iaddend.is selected from hydroxy, halogen and alkyl, alkoxy, haloalkyl and haloalkoxy groups having up to 4 carbon atoms and n and n' are each 0-3. These compounds and their salts have valuable pharmacological activity as anti-inflammatory agents. .Iadd.

What is claimed is:  .[.1. A compound of the formula: ##SPC5## 
       wherein R x  is a haloalkyl group having up to four carbon atoms and at least one halogen atom bonded to the alpha carbon atom or if there is no halogen bonded to said alpha carbon atom, having at least 2 halogen atoms bonded to the beta carbon atom, R is hydrogen, alkyl or alkenyl containing not more than three carbon atoms, or a pharmaceutically acceptable cation; each Y is selected from hydroxy, halogen and alkyl, alkoxy, haloalkyl and haloalkoxy groups having up to 4 carbon atoms and n and n' are each 0-3..]. .[.2. A compound according to claim 1 wherein the halogen atoms in the R x  group are all fluorine..]. .[.3. A compound according to claim 2 wherein R x  is a perfluoroalkyl group..]. .[.4. N-methyl 3-benzoyltrifluoromethanesulfonanilide according to claim 3..]. .[.5. 3-benzoyl-4-hydroxytrifluoromethanesulfonanilide according to claim 3..]. .[.6. A compound according to claim 1, in which the haloalkanesulfonamido group is in meta orientation to the carbonyl group..]. .[.7. A compound according to claim 6, in which R x  is HCF 2  --..]. .[.8. 3-benzoyldifluoromethanesulfonanilide according to claim 7..]. .[.9. The sodium salt of 3-benzoyldifluoromethanesulfonanilide according to claim 7..]. .[.10. A compound according to claim 6, in which R x  is H 2  CF--..]. .[.11. 3-benzoylfluoromethanesulfonanilide according to claim 10..].  .[.12. A compound of the formula: ##SPC6## 
       wherein R x  is a haloalkyl group having up to two carbon atoms and at least one halogen atom bonded to the alpha carbon atom or if there is no halogen bonded to said alpha carbon atom, having at least two halogen atoms bonded to the beta carbon atom, provided that the halogen in R x  is selected from chlorine and fluorine; R is hydrogen, methyl, ethyl or a pharmaceutically acceptable cation; each Y is selected from hydroxy, halogen, methyl and methoxy; and n and n' are each 0-1..]. .[.13. A compound according to claim 12 of the formula: ##SPC7##.]. .[.14. A compound according to claim 2 wherein R x  is trifluoromethyl..]. .Iadd. 15. A compound of the formula ##SPC8## 
       wherein R x  is a fluoromethyl group, R is hydrogen, alkyl or alkenyl containing not more than three carbon atoms, or a pharmaceutically acceptable cation; each Y and Y' is selected from hydroxy, halogen and alkyl, alkoxy, haloalkyl and haloalkoxy groups having up to 4 carbon atoms and n and n' are each 0-3. .Iaddend..Iadd. 16. A compound according to claim 15 wherein R x  is CF 3  --. .Iaddend. .Iadd. 17. N-methyl 3-benzoyltrifluoromethanesulfonanilide according to claim 16. .Iaddend..Iadd. 18. 3-Benzoyl-4-hydroxytrifluoromethanesulfonanilide according to claim 16. .Iaddend..Iadd. 19. A compound according to claim 15 in which R x  is HCF 2  --. .Iaddend..Iadd. 20. 3-Benzoyldifluoromethanesulfonanilide according to claim 19. .Iaddend..Iadd. 21. The sodium salt of 3-benzoyldifluoromethanesulfonanilide according to claim 19. .Iaddend..Iadd. 22. A compound according to claim 15 in which R x  is H 2  CF--. .Iaddend..Iadd. 23. 3-Benzoylfluoromethanesulfonanilide according to claim 22. .Iaddend..Iadd. 24. A compound according to claim 15 of the formula: ##SPC9## 
       wherein R is hydrogen, methyl, ethyl or a pharmaceutically acceptable cation. .Iaddend.