Hydroxamate sulfonamides as cd23 shedding inhibitors

1 . A compound of formula (1):

wherein:

Cy is an aryl or heteroaryl group;

m is zero or the integer 1, 2 or 3;

n is zero or the integer 1, 2 or 3; in which the sum of m and n is the integer 1, 2 or 3;

R 1 is a group selected from C 1-6 alkyl, aryl, heteroaryl, heterocycloalkyl, C 3-6 cycloalkyl, —C 1-6 alkylaryl, —C 1-6 alkylheteroaryl, —C 1-6 alkylheterocycloalkyl and —C 1-6 alkylC 3-6 cycloalkyl, in which each aryl and heteroaryl group, present as or as part of the group R 1 , is optionally substituted with 1, 2 or 3 R 7 substituents and in which each alkyl, heterocycloalkyl and cycloalkyl group, present as or as part of the group R 1 , is optionally substituted with 1, 2 or 3 R 8 substituents;

each R 7 is, independently, F, Cl, Br, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, —CN, —CO 2 R 7a , —CON(R 7a ) 2 or —COR 7a ;

each R 7a is, independently, a hydrogen atom, or a C 1-6 alkyl or C 1-6 haloalkyl group;

each R 8 is, independently F, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, ═O, ═NOR 10 , —CO 2 R 8a , —CON(R 8a ) 2 or —COR 8a ;

each R 8a is, independently a hydrogen atom, or a C 1-6 alkyl or C 1-6 haloalkyl group;

R 10 is a hydrogen atom or a C 1-3 alkyl group;

R 2 is a hydrogen atom or a C 1-3 alkyl group;

or R 1 and R 2 together with the carbon atom to which they are attached form a C 3-6 cycloalkyl or heterocycloalkyl group optionally substituted with 1, 2 or 3 R 9 substituents

each R 9 is, independently, F, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, ═O, ═NOR 10 , —CO 2 R 8a , —CON(R 8a ) 2 or —COR 8a ;

R 3 is F, Cl, Br, C 1-3 alkyl, C 1-3 haloalkyl, C 1-3 alkoxy or C 1-3 haloalkoxy;

R 4 is hydrogen, F, Cl, Br, C 1-3 alkyl, C 1-3 haloalkyl, C 1-3 alkoxy, C 1-3 haloalkoxy, —CN, —SO 2 R 5 , —SO 2 N(R 6 ) 2 , —CON(R 6 ) 2 , —N(R 6 ) 2 , —NHSO 2 R 5 or —NHCOR 5 ;

R 5 is a C 1-3 alkyl group;

each R 6 is, independently, a hydrogen atom or a C 1-3 alkyl group; and

R a and R b , which may be the same or different, are each hydrogen or C 1-3 alkyl, or R a and R b together with the carbon atom to which they are attached form a C 3-6 cycloalkyl or heterocycloalkyl group optionally substituted with 1, 2, or 3 R 9 substituents;

or a salt, solvate, hydrate, tautomer, isomer or N-oxide thereof.

2 . A compound according to claim 1 of formula (2):

or a salt, solvate, hydrate, tautomer, isomer or N-oxide thereof.

3 . A compound according to claim 1 of formula (3):

or a salt, solvate, hydrate, tautomer, isomer or N-oxide thereof.

4 . A compound according to claim 3 of formula (4):

or a salt, solvate, hydrate, tautomer, isomer or N-oxide thereof.

5 . A compound according to claim 1 wherein Cy is a phenyl group.

6 . A compound according to claim 1 wherein R a and R b are each a hydrogen atom.

7 . A compound according to claim 1 wherein m is the integer 1 and n is the integer 1.

8 . A compound according to claim 1 wherein R 1 is a group selected from C 1-6 alkyl, phenyl, heteroaryl, heterocycloalkyl, C 3-6 cycloalkyl, —(CH 2 ) 1-2 phenyl, —(CH 2 ) 1-2 heteroaryl, —(CH 2 ) 1-2 heterocycloalkyl and —(CH 2 ) 1-2 C 3-6 cycloalkyl, each of which is optionally substituted.

9 . A compound according to claim 8 wherein R 1 is a group selected from optionally substituted C 1-6 alkyl, phenyl, heterocycloalkyl, C 3-6 cycloalkyl and —(CH 2 ) 1-2 phenyl.

10 . A compound according to claim 1 wherein R 1 and R 2 together with the carbon atom to which they are attached form an optionally substituted C 3-6 cycloalkyl group.

11 . A compound according to claim 10 wherein R 1 and R 2 together with the carbon atom to which they are attached form a cyclobutyl group.

12 . A compound according to claim 1 wherein R 3 is F, Cl, methyl, ethyl, isopropyl, —CF 3 , —CF 2 H, methoxy, ethoxy, —OCF 3 or —OCF 2 H.

13 . A compound according to claim 1 wherein R 4 is hydrogen, F, Cl, methyl, —CF 3 , methoxy, ethoxy, —OCF 3 or —OCF 2 H.

14 . A compound according to claim 12 wherein R 3 is F, Cl, methyl, ethyl or methoxy.

15 . A compound according to claim 14 wherein R 3 is F, Cl, methyl or methoxy.

16 . A compound according to claim 14 wherein R 3 is a methyl group.

17 . A compound which is:

N-hydroxy-3-methyl-2-(4-o-tolylpiperazine-1-sulfonylmethyl)butyramide;

N-hydroxy-3-methyl-2-[4-(2-methyl-4-fluorophenyl)piperazine-1-sulfonylmethyl]butyramide;

N-hydroxy-3-methyl-2-[4-(2,4-dimethylphenyl)piperazine-1-sulfonylmethyl]-butyramide;

N-hydroxy-3-methyl-2-[4-(2-methyl-4-trifluoromethoxyphenyl)piperazine-1-sulfonylmethyl]butyramide;

2-benzyl-N-hydroxy-3-(4-o-tolylpiperazine-1-sulfonyl)propionamide;

2-benzyl-N-hydroxy-3-[4-(2-methyl-4-trifluoromethoxyphenyl)piperazine-1-sulfonyl]propionamide;

N-hydroxy-2-phenyl-3-(4-o-tolylpiperazine-1-sulfonyl)propionamide;

N-hydroxy-2(R)-(tetrahydropyran-4-yl)-3-(4-o-tolylpiperazine-1-sulfonyl)-propionamide;

N-hydroxy-3-methyl-2(R)-(4-o-tolylpiperazine-1-sulfonylmethyl)butyramide;

1-(4-o-tolylpiperazine-1-sulfonylmethyl)cyclobutanecarboxylic acid hydroxyamide;

or a salt, solvate, hydrate, tautomer, isomer or N-oxide thereof.

18 . A compound which is:

N-hydroxy-3-methyl-2-[4-(2-methoxyphenyl)piperazine-1-sulfonylmethyl]-butyramide;

N-hydroxy-3-methyl-2-[4-(2-chlorophenyl)piperazine-1-sulfonylmethyl]-butyramide;

or a salt, solvate, hydrate, tautomer, isomer or N-oxide thereof.

19 . A pharmaceutical composition comprising a compound according to claim 1 together with one or more pharmaceutically acceptable carriers, excipients or diluents.