PB62472

CLAIMS

1. A compound of formula (I) R1

N O (I) ( )a N R2 wherein

1 R represents straight chain C1-6alkyl; a represents 1 or 2;

2 3 4 2 R represents -C1-6alkylene-R -R , in which the alkylene is straight chain and is optionally substituted by one C1-3alkyl group, or R represents a 5 to 7 membered ring containing one SO2 group;

3 5 6 7 8 R represents -SO2-, -NR SO2-, -SO2NR - or –NR C(O)NR -;

4 R represents -C1-6alkyl, -C5-7cycloalkyl optionally substituted by one or two C1-3alkyl groups, -C1-3alkyleneC5-7cycloalkyl in which the C5-7cycloalkyl is optionally substituted by one or two C1-3alkyl groups, -aryl optionally substituted by one or two halogen, C1-3alkyl, trifluoromethyl, or cyano groups, or -C1-3alkylene-aryl optionally substituted by one or two halogen, C1-3alkyl, trifluoromethyl, or cyano groups;

5 6 7 8 R , R , R and R each independently represent hydrogen or C1-6aIkyl;

6 4 or together R and R represent a saturated 5 to 7 membered ring, optionally containing one –O-, -S-, -NH-, or –N(CH3)- group;

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8 4 or together R and R represent a saturated 5 to 7 membered ring, optionally containing one –O-, -S-, -NH-, or –N(CH3)- group; or a salt thereof.

1 2. A compound according to claim 1 in which R represents C2-5alkyl; a represents 1 or 2;

2 3 4 2 R represents -C2-5alkylene-R -R , in which the alkylene is straight chain and is optionally substituted by one C1-3alkyl group, or R represents a 5 membered ring containing one SO2 group;

3 5 6 7 8 R represents -SO2-, -NR SO2-, -SO2NR - or –NR C(O)NR -;

4 R represents -C1-4alkyl, -C5-6cycloalkyl, -C1alkyleneC5-6cycloalkyl, -aryl optionally substituted by one or two halogen, C1-3alkyl, trifluoromethyl, or cyano groups, or -C1alkylene-aryl optionally substituted by one or two halogen, C1-3alkyl, trifluoromethyl, or cyano groups;

5 6 7 8 R , R , R and R each independently represent hydrogen or C1-3aIkyl; or a salt thereof.

3. A compound according to claim 1 or claim 2 in which R1 represents n-butyl or n-pentyl.

4. A compound according to any of claims 1 to 3 in which a represents 2.

3 5 6 5. A compound according to any of claims 1 to 4 in which R represents -SO2-, -NR SO2- or -SO2NR -.

3 5 6 6. A compound according to claim 5 in which R represents -NR SO2- or -SO2NR -.

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4 7. A compound according to any of claims 1 to 6 in which R represents -C1-4alkyl, -C5-6cycloalkyl, -C1alkyleneC5-6cycloalkyl, -aryl optionally substituted by one or two halogen, C1-3alkyl, trifluoromethyl, or cyano groups, or -C1alkylene-aryl optionally substituted by one or two halogen,

C1-3alkyl, trifluoromethyl, or cyano groups.

5 6 7 8 8. A compound according to any of claims 1 to 7 in which R , R , R and R each independently represent hydrogen or C1-3alkyl.

9. A compound which is: 6-Butyl-8-({1-[2-(ethylsulfonyl)ethyl]-4-piperidinyl}oxy)quinoline; 6-Butyl-8-[(1-{2-[(1,1-dimethylethyl)sulfonyl]ethyl}-4-piperidinyl)oxy]quinoline; 6-Butyl-8-({1-[3-(methylsulfonyl)propyl]-4-piperidinyl}oxy)quinoline; 6-Butyl-8-({1-[3-(ethylsulfonyl)propyl]-4-piperidinyl}oxy)quinoline; 6-Butyl-8-({1-[3-(propylsulfonyl)propyl]-4-piperidinyl}oxy)quinoline; 6-Butyl-8-[(1-{3-[(1-methylethyl)sulfonyl]propyl}-4-piperidinyl)oxy]quinoline; 6-Butyl-8-[(1-{3-[(1,1-dimethylethyl)sulfonyl]propyl}-4-piperidinyl)oxy]quinoline; 6-Butyl-8-({1-[3-(cyclopentylsulfonyl)propyl]-4-piperidinyl}oxy)quinoline; 6-Butyl-8-[(1-{4-[(1,1-dimethylethyl)sulfonyl]butyl}-4-piperidinyl)oxy]quinoline; 6-Butyl-8-({1-[3-(ethylsulfonyl)butyl]-4-piperidinyl}oxy)quinoline; 8-({1-[3-(Ethylsulfonyl)propyl]-4-piperidinyl}oxy)-6-pentylquinoline; 6-Butyl-8-[((3R)-1-{3-[(1,1-dimethylethyl)sulfonyl]propyl}-3-pyrrolidinyl)oxy] quinoline; 6-Butyl-8-{[1-(1,1-dioxidotetrahydro-3-thienyl)-4-piperidinyl]oxy}quinoline; N-(2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)ethanesulfonamide; N-(2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)-2-methyl-1-propanesulfonamide;

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N-(2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)benzenesulfonamide; N-(3-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)ethanesulfonamide; N-(3-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)-1-propanesulfonamide; N-(3-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)-2-propanesulfonamide; N-(3-{4-[(6-Pentyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)ethanesulfonamide; N-(3-{4-[(6-Pentyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)-1-propanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)methanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)ethanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)-1-propanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)-2-propanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)-2-methyl-1-propanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)cyclohexanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)-1-cyclohexylmethanesulfonamide; N-(4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)-N-methylethanesulfonamide; N-(4-{4-[(6-Pentyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)ethanesulfonamide; N-(5-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}pentyl)methanesulfonamide; N-(5-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}pentyl)ethanesulfonamide; 2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}-N-(1,1-dimethylethyl) ethanesulfonamide; 3-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}-N-(1,1-dimethylethyl)-1-propanesulfonamide; 4-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}-N-propyl-1-butanesulfonamide; or N-(3-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}propyl)-N'-propylurea; or a salt thereof.

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10. A compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide, or a salt thereof.

11. A compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide, in the form of the free base.

12. A compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)ethanesulfonamide, in the form of a dihydrochloride salt.

13. A compound according to any of claims 1 to 10, or a pharmaceutically acceptable salt thereof.

14. A compound as defined in any of claims 1 to 10, or a pharmaceutically acceptable salt thereof for use in therapy.

15. A compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form of a dihydrochloride salt for use in therapy.

16. A compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form of the free base for use in therapy.

17. A compound according to any of claims 14 to 16 for use in the treatment of inflammatory and/or allergic diseases of the respiratory tract.

18. A compound according to claim 17 for use in the treatment of allergic rhinitis.

19. A composition which comprises a compound as defined in any of claims 1 to 10, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers and/or excipients.

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20. A composition which comprises a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form of a dihydrochloride salt, and one or more pharmaceutically acceptable carriers and/or excipients.

21. A composition which comprises a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form the free base, and one or more pharmaceutically acceptable carriers and/or excipients.

22. A composition according to any of claims 19 to 21, wherein said composition is suitable for intranasal delivery.

23. A combination comprising a compound as defined in any of claims 1 to 10, or a pharmaceutically acceptable salt thereof, and one or more other therapeutic agents.

24. A combination comprising a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form of a dihydrochloride salt, and one or more other therapeutic agents.

25. A combination comprising a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form the free base, and one or more other therapeutic agents.

26. A combination according to any of claims 23 to 25, in which said one or more therapeutic agents is a corticosteroid.

27. A combination according to claim 26 in which the corticosteroid is fluticasone furoate (6a,9a-difluoro-17a-[(2-furanylcarbonyl)oxy]-11b- hydroxy-16a-methyl-3-oxo-androsta-1,4-diene-17b-carbothioic acid S-fluoromethyl ester).

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28. The use of a compound as defined in any of claims 1 to 10, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment of inflammatory and/or allergic diseases of the respiratory tract.

29. The use of a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form of a dihydrochloride salt, in the manufacture of a medicament for the treatment of inflammatory and/or allergic diseases of the respiratory tract.

30. The use of a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide in the form of the free base, in the manufacture of a medicament for the treatment of inflammatory and/or allergic diseases of the respiratory tract.

31. The use according to any of claims 28 to 30, in which the disease is allergic rhinitis.

32. A method for the treatment of inflammatory and/or allergic diseases of the respiratory tract which comprises administering to a patient in need thereof an effective amount of a compound as defined in any of claims 1 to 10, or a pharmaceutically acceptable salt thereof.

33. A method for the treatment of inflammatory and/or allergic diseases of the respiratory tract which comprises administering to a patient in need thereof an effective amount of a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide, in the form of a dihydrochloride salt.

34. A method for the treatment of inflammatory and/or allergic diseases of the respiratory tract which comprises administering to a patient in need thereof an effective amount of a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl) ethanesulfonamide, in the form the free base.

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35. A method according to any of claims 32 to 34, in which the disease is allergic rhinitis.

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