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Claims for Patent: 3,674,876

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Claims for Patent: 3,674,876

Title: BENZOTHIAZINE DIOXIDES AS LIPID REGULATING AGENTS
Abstract:Certain 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide and 3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide compounds effective as lipid regulating agents are disclosed.
Inventor(s): Lombardino; Joseph G. (Niantic, CT), Holland; Gerald F. (Old Lyme, CT)
Assignee: Pfizer Inc. (N/A)
Application Number:04/831,768
Patent Claims: 1. A method of lowering lipid levels in a human which comprises the oral or parenteral administration to a human in need of said treatment an effective amount for lowering lipid levels of a compound selected from the group consisting of ##SPC1## or the base salts thereof with pharmacologically-acceptable cations, wherein X and Y are each a member selected from the group consisting of hydrogen, fluorine, chlorine, bromine, nitro, alkyl and alkoxy having from one to five carbon atoms, and trifluoromethyl; R is a member selected from the group consisting of --OR.sub.1 and --NHR.sub.2 wherein R.sub.1 is alkyl having from one to 12 carbon atoms or phenylalkyl having up to three carbon atoms in the alkyl moiety, and R.sub.2 is chosen from the group consisting of hydrogen, alkyl having from one to eight carbon atoms, alkenyl having up to six carbon atoms, cycloalkyl having up to eight carbon atoms, phenylalkyl having up to three carbon atoms in the alkyl moiety, phenyl, nitrophenyl, naphthyl, pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 4,6-dimethyl-2-pyridyl, 5-chloro-2-pyridyl, 5-bromo-2-pyridyl, 5-nitro-2-pyridyl, 3-hydroxy-2-pyridyl, 5-carboxamido-2-pyridyl, 2-pyrazinyl, 2-pyrimidyl, 4,5-dimethyl-2-pyrimidyl, 4-pyrimidyl, 5-methyl-3-pyridazinyl, 6-methoxy-3-pyridazinyl, 1-phenyl-3-pyrazolonyl, 2-thiazolyl, 4-methyl-2-thiazolyl, 4-phenyl-2-thiazolyl, 5-bromo-2-thiazolyl, 4,5-dimethyl-2-thiazolyl, 3-isothiazoyl, 2-benzothiazolyl, 6-methyl-2-benzothiazolyl, 4-chloro-2-benzothiazolyl, 6-bromo-2-benzothiazolyl, 5-chloro-2-benzoxazolyl, 1,3,4-thiadiazolyl, 5-methyl-1,3,4-thiadiazolyl, 1,2,4-triazolyl, 6-phenyl-1,2,4-triazolyl, 7-indazolyl, mono- and di-substituted phenyl wherein each substitutent is halogen, hydroxy, alkoxy or thioalkoxy having up to three carbon atoms, alkyl having up to four carbon atoms, trifluoromethyl, acetyl, methylsulfinyl or methylsulfonyl; R.sub.3 is a member selected from the group consisting of hydrogen, alkyl having from one to six carbon atoms, alkenyl having up to four carbon atoms and phenylalkyl having up to three carbon atoms in the alkyl moiety; and Z is oxygen or sulfur, except when R is --OR.sub.1 when it is oxygen.

2. The method of claim 1 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide having the first formula wherein R is --NHR.sub.2.

3. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is phenyl and R.sub.3 is alkyl of from one to six carbon atoms.

4. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2benzothiazine3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is sulfur, R.sub.2 is phenyl and R.sub.3 is alkyl of from one to six carbon atoms.

5. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is chlorophenyl and R.sub.3 is alkyl of from one to six carbon atoms.

6. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is phenylalkyl having up to three carbon atoms in the alkyl moiety and R.sub.3 is alkyl of from one to six carbon atoms.

7. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is alkenyl having up to six carbon atoms and R.sub.3 is alkyl of from one to six carbon atoms.

8. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is cycloalkyl having up to eight carbon atoms and R.sub.3 is alkyl of from one to six carbon atoms.

9. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is dichlorophenyl and R.sub.3 is alkyl of from one to six carbon atoms.

10. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is chlorophenyl and R.sub.3 is hydrogen.

11. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is 2-thiazolyl and R.sub.3 is alkyl of from one to six carbon atoms.

12. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is pyridyl and R.sub.3 is alkyl of from one to six carbon atoms.

13. The method of claim 2 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is monomethyl 2-pyridyl and R.sub.3 is alkyl of from one to six carbon atoms.

14. The method of claim 1 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide having the first formula wherein R is OR.sub.1 and Z is oxygen.

15. The method of claim 14 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide wherein X and Y are each hydrogen, R.sub.1 is alkyl having from one to 12 carbon atoms and R.sub.3 is alkyl of from one to six carbon atoms.

16. The method of claim 14 wherein said compound is a 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-3-carboxylate-1,1dioxide wherein X and Y are hydrogen, R.sub.1 is alkyl having from one to 12 carbon atoms and R.sub.3 is hydrogen.

17. The method of claim 1 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide having the second formula wherein R is --NHR.sub.2.

18. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is phenyl and R.sub.3 is alkyl of from one to six carbon atoms.

19. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is chlorophenyl and R.sub.3 is alkyl of from one to six carbon atoms.

20. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is pyridyl and R.sub.3 is alkyl of from one to six carbon atoms.

21. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is dichlorophenyl and R.sub.3 is alkyl having from one to six carbon atoms.

22. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is bromophenyl and R.sub.3 is alkyl of from one to six carbon atoms.

23. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is naphthyl and R.sub.3 is alkyl of from one to six carbon atoms.

24. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is alkyl having from one to eight carbon atoms and R.sub.3 is alkyl of from one to six carbon atoms.

25. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X is hydrogen, Y is alkyl having from one to five carbon atoms, Z is oxygen, R.sub.2 is dichlorophenyl and R.sub.3 is alkyl of from one to six carbon atoms.

26. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X is hydrogen, Y is alkyl having from one to five carbon atoms, Z is oxygen, R.sub.2 is bromophenyl and R.sub.3 is alkyl of from one to six carbon atoms.

27. The method of claim 17 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is phenyl and R.sub.3 is phenylalkyl having up to three carbon atoms in the alkyl moiety.

28. The method of claim 17 wherein said compound is a 3,4-dihydro-3oxo-2H-1,2-benzothiazine-4-carboxamide-1,1-dioxide wherein X and Y are each hydrogen, Z is oxygen, R.sub.2 is 2-thiazolyl and R.sub.3 is alkyl of from one to six carbon atoms.

29. The method of claim 1 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxylate-1,1-dioxide having the second formula wherein R is OR.sub.1 and Z is oxygen.

30. The method of claim 29 wherein said compound is a 3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxylate-1,1-dioxide wherein X and Y are each hydrogen, R.sub.1 is alkyl having from one to 12 carbon atoms and R.sub.3 is alkyl of from one to six carbon atoms.

31. The method of claim 17 wherein said compound is 3,4-dihydro-4'-ethoxy-2-methyl-3-oxo-2H-1,2-benzothiazine-4-carboxanilide -1,1-dioxide.

32. The method of claim 17 wherein said compound is 2-benzyl-4'-chloro-3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxanilide- 1,1-dioxide.

33. The method of claim 2 wherein said compound is 2,2',5'-trimethyl-4'-nitro-4-hydroxy-2H-1,2-benzothiazine-3-carboxanilide- 1,1-dioxide.

34. The method of claim 17 wherein said compound is 2-benzyl-2',4'-dichloro-3,4-dihydro-3-oxo-2H-1,2-benzothiazine-4-carboxani lide-1,1-dioxide.

35. The method of claim 2 wherein said compound is 4-hydroxy-2-methyl-N-(6-methyl-2-benzothiazolyl)-2H-1,2-benzothiazine-3-ca rboxamide-1,1-dioxide.

36. The method of claim 2 wherein said compound is N-(6-bromo-2-benzothiazolyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-car boxamide-1,1-dioxide.
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