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1. (WO2006031134) ANTI-INFLAMMATORY COMPOUNDS
Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

CLAIMS

1. A compound of formula (I)


where: W is N, CH or COH

Y is NH or NR2 and Z is S, SO or SO2, or
Z is NH or NR2 and Y is S, SO or SO2;
where R2 is straight or branched chain C1-C8 alkyl;

R1 is CO2H, CO2R3, CHO, C(=O)R3, CN, CONH2, CONHR3, CON(R3)2, CH(OH)(OR3), CH(OR3)2, H, halogen, NHCOR3, N(COR3)2, NH2, NHR3, N(R3)2, NO2, OH, OR3, SO2NHR3, SO2N(R3)2, SO3H, SO2NH2, SO2R3, or
R1 is straight or branched chain C1-C8 alkyl, C2-C8 alkenyl or C2- C8 alkynyl, each of which is optionally substituted with one or more substituents selected from aryl, heteroaryl, halogen, NH2, NHR4, N(R4)2, acyl, OH, OR4, or phosphate, or
R1 is a radical of formula (a), (b) or (c)


where n is an integer from 1 to 6;

where R3 is straight or branched chain C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl, aryl or heteroaryl group, optionally substituted with one or more substituents selected from halogen, NH2, NHR4, N(R4)2, OH, OR4, acyl or phosphate;

and where R4 is a straight or branched chain C1-C8 alkyl group, or where two R4 groups together form a cyclopentyl, cyclohexyl, morpholyl, or N-methylpiperazinyl substituent;

indicates a single bond or a double bond;

provided that the following compounds are excluded:

3,4-dihydro-2H-naphtho[2,3-b]-1 ,4-thiazine-5,10-dione;
2,3-dihydro-7-methy!-1 H-pyrido[3,2-g][1 ,4]benzothiazine-5,10-dione;

2,3-dihydro-1H-pyrido[3>2-g][1,4]benzothiazine-5,10-dione;
3,4-dihydro-8-(4-methyl-3-pentenyl)-1 , 1 -dioxide-2H-naphtho[2,3-b]- 1 ,4-thiazine-5, 10-dione;
3,4-dihydro-7-(4-methyl-3-pentenyl)-1 , 1 -dioxide-2H-naphtho[2,3-b]- 1,4-thiazine-5,10-dione;
3,4-dihydro-1 ,1-dioxide-2H-naphtho[2,3-b]-1 ,4-thiazine-5,10-dione;

or:

a compound of formula (II)


where: W, Y, Z and R1 are as defined above;
R5 is H1 C1-C8 alkyl or acyl; and
indicates a single bond or a double bond;

or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

2. A compound as claimed in claim 1 which is a compound of formula (I).

3. A compound as claimed in claim 1 which is a compound of formula (II).

4. A compound as claimed in any one of claims 1 to 3 where R1 is straight or branched chain C1-C8 alkyl, CO2H, CO2R3, CHO, CN, CON(R3)2, COH(OR3), H, or a radical of formula (a), (b) or (c).

5. A compound as claimed in claim 4 where R1 is straight or branched chain C1-C8 alkyl, CO2H, CO2R3, CN or CON(R3)2.

6. A compound as claimed in claim 5 where R1 is straight or branched chain C1-C8 alkyl.

7. A compound as claimed in claim 6 where R1 is methyl.

8. A compound as claimed in claim 6 where R1 is substituted with one or more N(R4)2 substituents where the two R4 groups together form a morpholyl substituent.

9. A compound as claimed in claim 5 where R1 is CON(R3)2.

10. A compound as claimed in claim 9 where R3 is methyl.

11. A compound as claimed in claim 5 where R1 is CO2R3.

12. A compound as claimed in claim 11 where R3 is straight or branched chain C1-C8 alkyl.

13. A compound as claimed in claim 12 where R3 is methyl.

14. A compound as claimed in claim 5 where R1 is CO2H.

15. A compound as claimed in claim 5 where R1 is CN.

16. A compound as claimed in any one of claims 1 to 15 where Y is NH or NR2 and Z is S, SO or SO2.

17. A compound as claimed in claim 16 where Y is NH and Z is SO2.

18. A compound as claimed in any one of claims 1 to 15 where Z is NH or NR2 and Y is S, SO or SO2.

19. A compound as claimed claim 18 where Z is NH and Y is SO2.

20. A compound as claimed in claim 2 where R1 is CO2H or CO2R3 and Y is S, SO or SO2.

21. A compound as claimed in any one of claims 1 to 20 where W is N.

22. A compound as claimed in any one of claims 1 to 20 where W is CH.

23. A compound as claimed in any one of claims 1 to 20 where W is COH.

24. A compound as claimed in any one of claims 1 to 19, 21 , 22 or 23 where R5 is H.

25. A compound as claimed in claim 2 where W is N and R1 is straight or branched chain C1-C8 alkyl or CO(NR3)2.

26. A compound as claimed in claim 25 where R1 is methyl.

27. A compound as claimed in claim 25 where R3 is methyl.

28. A compound as claimed in claim 1 , selected from:



(5) (6)
(4)

(8) (9) (10) (11)
(7)



(14)
(12) (13)



(15) (16) (17)


or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

29. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound as claimed in any one of claims 1 to 28.

30. A method of treating an inflammatory disease or disorder, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of formula (III) or a compound of formula (IV):



(III) (IV)

where: W, Y, Z, R1 and R5 are as defined in claim 1 ; and
indicates a single bond or a double bond;

or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

31. A method as claimed in claim 30 where the inflammatory disease or disorder is an inflammatory disease of the joints, skin, muscle, nervous system, lungs, kidneys, liver or gastrointestinal tract, or a disease in which inflammatory processes play a secondary role in the development of pathology or where inflammatory processes are involved in pathogenesis as a secondary phenomenon, such as vascular diseases, or an autoimmune disease where organ damage is mediated by inflammation.

32. A method as claimed in claim 31 where the inflammatory disease or disorder is gout, acute or chronic idiopathic inflammatory arthritis, psoriasis, chronic dermatosis, myositis, a demyelinating disease, chronic obstructive pulmonary disease, interstitial lung disease, glomerulonephritis, interstitial nephritis, chronic active hepatitis, Crohn's disease, ulcerative colitis, plaque formation in atherosclerosis, a degenerative disease of the joints or nervous system, or multiple sclerosis.