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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 7,144,883
- Publication Date: December 05, 2006
- Appl. No: 10/167141
- Application Filed: June 11, 2002
- Assignees: Biovitrum AB (Stockholm, SE)
- Claim: 1. A compound of the formula I [chemical expression included] or a pharmaceutically acceptable salt thereof, wherein: ring B is [chemical expression included] in which D is a five-membered heterocyclic or heteroaryl ring, said ring comprising one or two atoms selected from the group consisting of nitrogen, sulfur and oxygen, with the proviso that when D contains an oxygen atom, D is heteroaryl; W is —(CH); P is [chemical expression included] P and R 3 are bound to the same ring and are disposed in meta- or para-positions relative to each other; R 1 is (a) C 1-6 alkyl, (b) C 1-6 alkoxyalkyl, (c) straight or branched C 1-6 hydroxyalkyl, (d) straight or branched C 1-6 alkylhalides; or (e) a group Ar; Ar is (a) phenyl, (b) 1-naphthyl, (c) 2-naphthyl, (d) benzyl, (e) cinnamoyl, (f) a 5 to 7-membered, optionally aromatic, partially saturated or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, or (g) a bicyclic ring system comprising at least one heterocyclic ring according to (f); wherein the group Ar is substituted in one or more positions with (a) H, X or Y, or (b) a 5 to 7-membered, optionally aromatic, partially saturated or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur; R 2 is (a) H, (b) C 1-6 alkyl, (c) C 1-6 alkoxy, (d) straight or branched C 1-6 hydroxyalkyl, or (e) straight or branched C 1-6 alkylhalides; or R 1 and R 2 are linked to form a group (CH 2) 4 O; one of R 3 is a group [chemical expression included] X and Y are independently (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 4 , (r) —NR 4 R 5 , (s) —NO 2 , (t) —CONR 4 R 5 , (u) —NHSO 2 R 4 , (v) —NR 4 COR 5 , (x) —SO 2 NR 4 R 5 , (z) —C(═O)R 4 , (aa) —CO 2 R 4 , (ab) —S(O) n R 4 wherein n is 0, 1, 2 or 3, (ac) —S—(C 1-6)alkyl, or (ad) —SCF 3 ; R 4 and R 5 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 4 and R 5 are linked to form a group (CH 2) 2 O, (CH 2) 4 O or (CH 2) 3-5 ; and R 6 is (a) H, or (b) straight of branched C 1-6 alkyl.
- Claim: 2. The compound according to claim 1 of the general formula VI [chemical expression included] wherein R 3 , P, X and Y are as defined for formula (I) in claim 1 ; and wherein D is a five-membered heterocyclic or heteroaryl ring, said ring comprising one or two atoms selected from the group consisting of nitrogen, sulfur and oxygen, with the proviso that when D contains an oxygen atom, D is heteroaryl, and wherein when the heteroaryl ring comprises one or two nitrogen atoms, a group R 6 is attached at the secondary nitrogen, in which R 6 is as defined for formula (I) in claim 1 .
- Claim: 3. The compound according to claim 1 , wherein R 1 is (a) C 1-6 alkyl, or (e) a group Ar; Ar is (a) phenyl, (b) 1-naphthyl, (c) 2-naphthyl, or (f) a 5 to 7-membered, optionally aromatic, partially saturated or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur; wherein the group Ar is substituted in one or more positions with X or Y; wherein X or Y is (a) H, (b) halogen, (c) C 1-6 alkyl, (d) —CF 3 , (f) C 1-6 alkoxy, (g) C 1-4 alkenyl, (l) —OCF 3 , or (n) straight or branched C 1-6 hydroxyalkyl; R 2 is (a) H, or (b) C 1-3 alkyl; or R 1 and R 2 are linked to form a group (CH 2) 4 O; R 3 is [chemical expression included] wherein R 6 is (a) H, or (b) C 1-6 alkyl; and D is pyrrolyl, thienyl or furanyl.
- Claim: 4. The compound of claim 3 , wherein R 6 is methyl.
- Claim: 5. The compound of claim 3 , wherein R 2 is methyl.
- Claim: 6. The compound according to claim 1 , which is the compound 3-Cyanophenyl-N-(7-piperazin-1-yl-benzofuran-5-yl)-benzenesulfonamide, hydrochloride, 4-Phenoxy-N-(7-piperazin-1-yl-benzofuran-5-yl)-benzenesulfonamide, hydrochloride, 1-Naphthyl-N-(7-piperazin-1-yl-benzofuran-5-yl)-benzenesulfonamide, hydrochloride, N-(7-Piperazin-1-yl-benzofuran-5-yl)-benzenesulfonamide, hydrochloride, 5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonic acid (7-piperazin-1-yl-benzofuran-5-yl)-amide hydrochloride, or N-[7-(4-Methylpiperazin-1-yl)-1-benzofuran-5-yl]-benzenesulfonamide, hydrochloride.
- Claim: 7. A pharmaceutical formulation containing a compound according to claim 1 as active ingredient, in combination with a pharmaceutically acceptable diluent or carrier.
- Claim: 8. A method for the treatment of obesity, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1 .
- Claim: 9. A method for the treatment of obesity, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 2 .
- Claim: 10. A method for the treatment of obesity, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 6 .
- Claim: 11. A method for the treatment of type II diabetes, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1 .
- Claim: 12. A method for the treatment of type II diabetes, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 2 .
- Claim: 13. A method for the treatment of type II diabetes, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 6 .
- Claim: 14. A method for the treatment of binge disorders, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1 .
- Claim: 15. A method for the treatment of binge disorders, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 2 .
- Claim: 16. A method for the treatment of binge disorders, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 6 .
- Claim: 17. A method for reducing body-weight or reducing food intake, comprising administering to a subject in need thereof an effective amount of a compound according to claim 1 .
- Claim: 18. A method for reducing body-weight or reducing food intake, comprising administering to a subject in need thereof an effective amount of a compound according to claim 2 .
- Claim: 19. A method for reducing body-weight or reducing food intake, comprising administering to a subject in need thereof an effective amount of a compound according to claim 6 .
- Current U.S. Class: 51425/411
- Patent References Cited: 4808595 February 1989 Hoffman, Jr. ; 0 701 819 March 1996 ; 0 815 861 January 1998 ; 1 020 445 July 2000 ; 947606 January 1964 ; WO 84/01151 March 1984 ; WO 94/21619 September 1994 ; WO 98/27081 June 1998 ; WO 9827081 June 1998 ; WO 99/02502 January 1999 ; WO 99/37623 July 1999 ; WO 99/42465 August 1999 ; WO 00/12073 March 2000 ; WO 00/55159 September 2000 ; WO 01/32646 May 2001 ; WO 01/32660 May 2001 ; WO 200132646 May 2001 ; WO 01/85722 November 2001 ; WO 01/96336 December 2001 ; WO 02/32863 April 2002 ; WO 02/092585 November 2002 ; WO 02/098857 December 2002 ; WO 02/100822 December 2002
- Other References: STN International, file CAPLUS, CAPLUS Accession No. 1970:509549, document No. 73:109549, Werbel, Leslie M. et al: Synthetic schistosomicides . . . J. Med. Chem 13(4):592-598, 1970. cited by other ; Methvin Isaac et al., “6-Bicyclopiperazinyl-1-arylsulfonylindoles and 6-Bicyclopiperidinyl-1-arylsulfonylindoles Derivatives as Novel, Potent, and Selective 5-HT6 Receptor Antagonists”, Bioorganic & Medicinal Chemistry Letters, 10, pp. 1719-1721 (2000). cited by other
- Primary Examiner: Coleman, Brenda
- Attorney, Agent or Firm: Fish & Richardson P.C.
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