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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 7,718,650
- Publication Date: May 18, 2010
- Appl. No: 11/960045
- Application Filed: December 19, 2007
- Assignees: Biovitrum AB (SE)
- Claim: 1. A compound of the formula (II) [chemical expression included] 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 [chemical expression included] 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.
- Claim: 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.
- Claim: 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.
- Claim: 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.
- Claim: 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.
- Claim: 6. A compound according to claim 1 wherein R 1 is (a) a group Ar; or (b) C 1-6 alkyl.
- Claim: 7. A compound according to claim 1 wherein R 10 is H.
- Claim: 8. A compound according to claim 6 wherein R 10 is H.
- Claim: 9. A compound according to claim 7 wherein R 10 , R 14 and Y are each H.
- Claim: 10. A compound according to claim 8 wherein R 10 , R 14 and Y are each H.
- Claim: 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.
- Claim: 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
- Claim: 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.
- Current U.S. Class: 514/218
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- Primary Examiner: Kifle, Bruck
- Attorney, Agent or Firm: Fish & Richardson P.C.
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