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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 6,969,710
- Publication Date: November 29, 2005
- Appl. No: 10/144677
- Application Filed: May 13, 2002
- Assignees: Biovitrum AB (Stockholm, 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 and R 3 are independently (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); alternatively, R 1 and R 3 are linked to form a group (CH 2) 2 O, (CH 2) 4 O, or (CH 2) 3-5 in formula (Ib); 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 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) 2 O, (CH 2) 4 O, or (CH 2) 3-5 in formula (Ia); R 5 is selected from the group consisting of the following chemical groups: [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) 2 O, (CH 2) 4 O or (CH 2) 3-5 ; R 8 is (a) H, or (b) C 1-6 alkyl.
- Claim: 2. A compound according to claim 1 wherein R 1 is a group Ar; 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 substituted with Y, wherein Y is (a) H, (b) halogen, (c) C 1-6 alkyl, (d) CF 3 , (f) C 1-6 alkoxy, (g) C 1-4 alkenyl; (h) phenyl; (l) OCF 3 , or (n) straight or branched C 1-6 hydroxyalkyl.
- Claim: 3. A compound according to claim 1 , wherein the group [chemical expression included] is attached to the phenyl ring in 2-position or 3-position.
- Claim: 4. A compound according to claim 1 , wherein R 2 is —SO 2 R 1 .
- Claim: 5. A compound according to claim 1 , wherein R 3 and R 4 are independently H, methyl or ethyl.
- Claim: 6. A compound according to claim 1 , wherein R 8 is H or methyl.
- Claim: 7. A compound according to claim 1 , wherein R 6 and R 7 are independently (a) H, (b) C 1-6 alkyl, (c) C 3-7 cycloalkyl, or (d) Ar.
- Claim: 8. A compound according to claim 1 , which is the compound N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride N-(4-(1,4-diazepan-1-yl)-2-{[(3-fluorophenyl)sulfonyl]-amino}phenyl)-3-fluorobenzenesulfonamide hydrochloride N-{5-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-N-ethylbenzenesulfonamide hydrochloride N-{5-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride N-{5-(1,4-diazepan-1-yl)-2-[(ethylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}[1,1′-biphenyl]-4-sulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-2,1,3-benzoxadiazole-4-sulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-2-naphthalenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[methyl(methylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-N-methylbenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[methyl(phenylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-1-naphthalenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-2-naphthalenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-4-fluorobenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-4-nitrobenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-3-(trifluoromethyl)benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-2-methylbenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-4-(trifluoromethoxy)beazenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-3,5-dimethyl-4-isoxazolesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-3-methoxybenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-4-methylbenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[ethyl(methylsulfonyl)amino]phenyl}-4-methylbenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[ethyl(methylsulfonyl)amino]phenyl}-3,4-dimethoxybenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[ethyl(methylsulfonyl)amino]phenyl}-7-quinolinesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[methyl(methylsulfonyl)amino]phenyl}-4-methylbenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[methyl(methylsulfonyl)amino]phenyl}-1-naphthalenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[methyl(methylsulfonyl)amino]phenyl}-5-(2-pyridinyl)-2-thiophenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-1-naphthalenesulfonainide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-5-(dimethylamino)-1-naphthalenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-8-quinolinesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-2,4,6-trimethylbenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-4-methylbenzenesulfonamide hydrochloride N-[5-(1,4-diazepan-1-yl)-2-({[(E)-2-phenylethenyl]sulfonyl}amino)phenyl]benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-2,5-dimethoxybenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-2-methylbenzenesulfonamide hydrochloride 4-butoxy-N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-3,5-dimethyl-4-isoxazolesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-5-fluoro-2-methylbenzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-4-(methylsulfonyl)benzenesulfonamide hydrochloride N-{4-(1,4-diazepan-1-yl)-2-[(methylsulfonyl)amino]phenyl}-N-methylbenzenesulfonamide hydrochloride N-{5-(1,4-diazepan-1-yl)-2-[methyl(phenylsulfonyl)amino]phenyl}-4-methylbenzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-(4-methoxyphenyl)benzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-(3-methoxyphenyl)benzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-(2-methoxyphenyl)benzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-(3-fluorophenyl)benzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-methyl-N-phenylbenzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-(4-isopropylphenyl)benzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-(4-methylphenyl)benzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-(2,5-dimethylphenyl)benzenesulfonamide hydrochloride 3-amino-N-(3-chlorophenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-N-(2-chlorophenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-N-(2,4-dichlorophenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-N-(2-methyl-5-chloro-phenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-N-(2-methyl-3-chloro-phenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-N-(4-trifluoro-phenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-N-(4-fluorophenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-N-(2-fluorophenyl)-4-(1,4-diazepan-1-yl)benzenesulfonamide hydrochloride 3-amino-4-(4-methyl-1,4-diazepan-1-yl)-N-phenylbenzenesulfonamide hydrochloride 4-(1,4-diazepan-1-yl)-3-nitro-N-phenylbenzenesulfonamide hydrochloride 3-amino-4-(1,4-diazepan-1-yl)-N-phenylbenzenesulfonamide hydrochloride 2-(1,4-diazepan-1-yl)-5-(4-morpholinylsulfonyl)phenylamine hydrochloride 4-(1,4-diazepan-1-yl)-N-phenyl-3-[(phenylsulfonyl)amino]benzenesulfonamide hydrochloride 4-(1,4-diazepan-1-yl)-N-phenyl-3-[(methylsulfonyl)amino]benzenesulfonamide hydrochloride 2-(3-amino-4-[1,4]diazepan-1-yl-benzenesulfonyl)-benzamide diacetic acid; or 4-[4-(3,4-dihydro-2H-quinoline-1-sulfonyl)-2-amino-phenyl]-[1,4]diazepane ditrifluoroacetic acid.
- Claim: 9. 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) symmetric or asymmetric sulfonylation of the amine by a sulfonylchloride; (d) introduction of groups R 3 and R 4 by alkylation reactions in basic conditions.
- Claim: 10. A pharmaceutical formulation containing a compound of claim 1 as an active ingredient, in combination with a pharmaceutically acceptable diluent or carrier.
- Claim: 11. A compound of the formula (I) [chemical expression included] or a pharmaceutically acceptable salt thereof, wherein X is [chemical expression included] R 1 and R 3 are independently (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, aromatic, 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) 2 O, (CH 2) 4 O, or (CH 2) 3-5 in formula (Ib); 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 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) 2 O, (CH 2) 4 O, or (CH 2) 3-5 in formula (Ia); R 5 is selected from the group consisting of the following chemical groups: [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) 2 O, (CH 2) 4 O or (CH 2) 3-5 , R 8 is (a) H, or (b) C 1-6 alkyl.
- Claim: 12. The compound of claim 11 , wherein Ar is a 5 to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur.
- Claim: 13. The compound of claim 12 , wherein Ar is isoxazolyl, benzoxadiazolyl, quinolinyl, or thienyl.
- Claim: 14. 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 as in claims 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 11 , 12 , or 13 .
- Claim: 15. 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 .
- Claim: 16. The method of claim 15 , wherein the mammal in need of such treatment is an obese mammal.
- Claim: 17. A method for the treatment of schizophrenia, the method comprising administering to a mammal in need of such treatment an effective amount of a compound as in claims 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 11 , 12 , or 13 .
- 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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