Aryl sulfonamide compounds for treating obesity

1. A compound of the formula (II)

or a pharmaceutically acceptable salt thereof, wherein

R 9 , R 12 and R 14 are H; or

two of R 9 , R 12 and R 14 are H; and the remaining of R 9 , R 12 and R 14 is

(a) —NH 2 ,

(b) —NHR 6 ,

(c) —NR 6 R 7 ,

(d) —N(CO)R 6 ,

(e) —N(CS)R 6 , or

(f) —NO 2 ;

R 10 is a group R 3 ;

R 11 is a group R 1 ;

in which each of R 1 and R 3 , independently, is:

(a) H

(b) C 1-6 alkyl,

(c) C 1-6 alkoxy,

(d) straight or branched C 1-6 hydroxyalkyl,

(e) straight or branched C 1-6 alkylhalides; or

(f) a group Ar;

Ar is

(a) phenyl,

(b) 1-naphthyl,

(c) 2-naphthyl,

(d) benzyl,

(e) cinnamoyl,

(f) a 5 to 7-membered, partially or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, or

(g) a bicyclic ring system consisting of two heterocyclic rings as defined under (f), or a bicyclic ring system consisting of one benzene ring and one heterocyclic ring as defined under (f);

optionally, the group Ar is substituted with

(a) Y, or

(b) a 5 to 7-membered, partially or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur; Y is

(a) H,

(b) halogen,

(c) C 1-6 alkyl,

(d) CF 3 ,

(e) hydroxy,

(f) C 1-6 alkoxy,

(g) C 1-4 alkenyl;

(h) phenyl;

(i) phenoxy,

(j) benzyloxy,

(k) benzoyl,

(l) OCF 3 ,

(m) CN,

(n) straight or branched C 1-6 hydroxyalkyl,

(o) straight or branched C 1-6 alkylhalides,

(p) NH 2 ,

(q) NHR 6 ,

(r) NR 6 R 7 ,

(s) NO 2 ,

(t) —CONR 6 R 7 ,

(u) NHSO 2 R 6 ,

(v) NR 6 COR 7 ,

(x) SO 2 NR 6 R 7 ,

(z) —C(═O)R 6 ,

(aa) —CO 2 R 6 , or

(ab) S(O) n R 6 ; wherein n is 0, 1, 2 or 3;

R 13 is

R 6 and R 7 are independently

(a) H,

(b) C 1-6 alkyl,

(c) C 3-7 cycloalkyl, or

(d) Ar, as defined above for R 1 ;

alternatively, R 6 and R 7 are linked to form a group (CH 2 ) 3-5 ;

R 8 is

(a) H, or

(b) C 1-6 alkyl.

2. A compound according to claim 1 or a pharmaceutically acceptable salt thereof wherein R 13 is

(a) homopiperazine,

(b) methylhomopiperazine,

with the proviso that only one of R 9 , R 12 and R 14 is —NH 2 , —NHR 6 , —NR 6 R 7 , —N(CO)R 6 , —N(CS)R 6 , —NO 2 ; the other ones are H.

3. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof, which is selected from the following compounds

4-chloro-N-[5-(4-methyl-1,4-diazepan-1-yl)-2-nitrophenyl]benzenesulfonamide,

N-[2-amino-5-(1,4-diazepan-1-yl)phenyl]benzenesulfonamide,

N-[2-amino-5-(4-methyl-1,4-diazepan-1-yl)phenyl]benzenesulfonamide, and

N-[4-amino-5-(methyl-1,4-diazepan-1-yl)phenyl]benzenesulfonamide, and pharmacecutically acceptable salts thereof.

4. A process for the preparation of a compound of claim 1 comprising:

(a) introduction of a cyclic diamine into a halogen and nitro substituted benzene under mild and basic conditions;

(b) reduction of the nitro to a corresponding amine;

(c) selective introduction of a sulfonylamide group by a sulphonylchloride reacting with the amine;

(d) introduction of a sulfonylanimo group by an aromatic nucleophilic substitution reaction.

5. A pharmaceutical formulation containing a compound according to claim 1 , or as pharmaceutically acceptable salt therof, as an active ingredient, in combination with a parmaceutically acceptable diluent or carrier.

6. A compound according to claim 1 wherein R 1 is

(a) a group Ar; or

(b) C 1-6 alkyl.

7. A compound according to claim 1 wherein R 10 is H.

8. A compound according to claim 6 wherein R 10 is H.

9. A compound according to claim 7 wherein R 10 , R 14 and Y are each H.

10. A compound according to claim 8 wherein R 10 , R 14 and Y are each H.

11. A method for the treatment of a disorder of the central nervous system wherein the disorder of the central nervous system is selected from the group consisting of anxiety and depression, wherein the method comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

12. A method for the treatment of obesity, comprising administering to a mammal, in need of such treatment an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof

13. A method for the treatment of type II diabetes, comprising administering to a mammal, in need of such treatment an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.