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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 7,566,715
- Publication Date: July 28, 2009
- Appl. No: 11/215173
- Application Filed: August 30, 2005
- Assignees: Biovitrum AB (SE)
- Claim: 1. A compound of the formula (I) [chemical expression included] or a pharmaceutically acceptable salt thereof, wherein X is [chemical expression included] R 1 is a group Ar; R 3 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; each 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); alternatively, R 1 and R 3 are linked to form a group (CH 2) 3-5 in formula (Ib); optionally, the group Ar is substituted with one or more substituents selected from the group consisting of (a) halogen, (b) C 1-6 alkyl, (c) CF 3 , (d) hydroxy, (e) C 1-6 alkoxy, (f) C 1-4 alkenyl; (g) phenyl; (h) phenoxy, (i) benzyloxy, (j) benzoyl, (k) OCF 3 , (l) CN, (m) straight or branched C 1-6 hydroxyalkyl, (n) straight or branched C 1-6 alkylhalides, (o) NH 2 , (p) NHR 6 , (q) NR 6 R 7 , (r) NO 2 , (s) —CONR 6 R 7 , (t) NHSO 2 R 6 , (u) NR 6 COR 7 , (v) SO 2 NR 6 R 7 , (w) —C(═O)R 6 , (x) —CO 2 R 6 , or (y) S(O) n R 6 ; wherein n is 0, 1, 2 or 3; and (z) 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 2 and R 4 are independently: (a) —SO 2 R 1 , (b) H, (c) C 1-6 alkyl, (d) C 1 -C 3 alkenyl, (e) C 1 -C 3 alkylaryl, (f) Ar as defined above for R 1 , (g) —C(═O)R 6 , (h) —C(O)NR 6 R 7 , (i) —C(S)NR 6 R 7 , (j) —CO 2 R 6 ; (k) —C(S)R 6 ; (l) straight or branched C 1-6 hydroxyalkyl, or (m) straight or branched C 1-6 alkylhalides; alternatively, R 2 and R 4 are linked to form a group (CH 2) 3-5 in formula (Ia); R 5 is selected from the group consisting of the following chemical groups: [chemical expression included] each R 6 and R 7 is independently (a) H, (b) C 1-6 alkyl, (c) C 3-7 cycloalkyl, or (d) Ar 1 ; wherein each Ar 1 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 1 is substituted with one or more substituents selected from the group consisting of (a) halogen, (b) C 1-6 alkyl, (c) CF 3 , (d) hydroxy, (e) C 1-6 alkoxy, (f) C 1-4 alkenyl; (g) phenyl; (h) phenoxy, (i) benzyloxy, (j) benzoyl, (k) OCF 3 , (l) CN, (m) straight or branched C 1-6 hydroxyalkyl, (n) straight or branched C 1-6 alkylhalides, (o) NH 2 , (p) NHR 9 , (q) NR 9 R 10 , (r) NO 2 , (s) —CONR 9 R 10 , (t) NHSO 2 R 9 , (u) NR 9 COR 10 , (v) SO 2 NR 9 R 10 , (w) —C(═O)R 9 , (x) —CO 2 R 9 , or (y) S(O) n R 9 ; wherein n is 0, 1, 2 or 3; and (z) a 5 to 7-membered, partially or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur; 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; and each R 9 and R 10 is independently (a) H, (b) C 1-6 alkyl; or (c) C 3-7 cycloalkyl; or alternatively, R 9 and R 10 are linked to form a group (CH 2) 3-5 .
- Claim: 2. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ar is (a) phenyl, (b) 1-naphthyl, (c) 2-naphthyl, or (f) a 5 to 7-membered, partially or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur; the group Ar is optionally substituted one or more substituents selected from the group consisting of (a) halogen, (b) C 1-6 alkyl, (c) CF 3 , (d) C 1-6 alkoxy, (e) C 1-4 alkenyl; (f) phenyl; (g) OCF 3 , and (h) straight or branched C 1-6 hydroxyalkyl.
- Claim: 3. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the group [chemical expression included] is attached to the phenyl ring in 2-position and 3-position.
- Claim: 4. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 is —SO 2 R 1 .
- Claim: 5. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 3 and R 4 are independently H, methyl or ethyl.
- Claim: 6. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R 6 and R 7 is independently (a) H, (b) C 1-6 alkyl, (c) C 3-7 cycloalkyl, or (d) Ar 1 .
- Claim: 7. A compound according to claim 1 , which is the compound 3-amino-4-(hexahydro-pyrrolo[1,2-α]pyrazin-2-yl)-N-(2-methoxyphenyl)-benzenesulfonamide; 3-amino-4-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)N-phenyl-benzenesulfonamide; or 3-amino-4-(5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-N-phenyl-benzenesulfonamide; or a pharmaceutically acceptable salt of such a compound.
- Claim: 8. A pharmaceutical formulation comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, as an active ingredient, in combination with a pharmaceutically acceptable diluent or carrier.
- Claim: 9. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein Ar is a 5 to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur.
- Claim: 10. The compound of claim 9 , or a pharmaceutically acceptable salt thereof, wherein Ar is isoxazolyl, benzoxadiazol, quinolinyl, or thienyl.
- Claim: 11. A method for the treatment of obesity, the method comprising administering to a mammal in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.
- Claim: 12. A method for the reduction of food intake, the method comprising administering to a mammal in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.
- Claim: 13. The method of claim 12 , wherein the mammal in need of such treatment is an obese mammal.
- Claim: 14. A method for the treatment of a disorder of the central nervous system selected from the group consisting of anxiety, depression, sleep disorders, and schizophrenia, the method comprising administering to a mammal in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.
- Claim: 15. The method of claim 14 , wherein the disorder is depression.
- Claim: 16. The method of claim 14 , wherein the disorder is anxiety.
- Claim: 17. The method of claim 14 , wherein the disorder is schizophrenia.
- Claim: 18. The method of claim 14 , wherein the disorder is sleep disorders.
- Claim: 19. A method for the treatment of type II diabetes, the method comprising administering to a mammal in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.
- Claim: 20. A method for the treatment of a disorder of the central nervous system wherein the disorder is a memory disorder, the method comprising administering to a mammal in need of such treatment an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.
- Current U.S. Class: 514/249
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- Primary Examiner: Kifle, Bruck
- Attorney, Agent or Firm: Fish & Richardson P.C.
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