| Sonstiges: |
- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 7,319,097
- Publication Date: January 15, 2008
- Appl. No: 11/214523
- Application Filed: August 30, 2005
- Assignees: Biovitrum AB (SE)
- Claim: 1. A method for the treatment of type II diabetes, the method comprising administering to a subject in need thereof an effective amount of a compound of 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. The method of 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. The method of claim 1 , wherein the group [chemical expression included] is attached to the phenyl ring in 2-position and 3-position.
- Claim: 4. The method of claim 1 , wherein R 2 is —SO 2 R 1 .
- Claim: 5. The method of claim 1 , wherein R 3 and R 4 are independently H, methyl or ethyl.
- Claim: 6. The method of claim 1 , wherein R 5 is selected from the group consisting of the following chemical groups: [chemical expression included] wherein R 8 is H or methyl.
- Claim: 7. The method of 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. The method of claim 1 , wherein the compound of formula (I) is N-[2-{ethyl[(3-fluorophenyl)sulfonyl]amino}-4-(4-methyl-1-piperazinyl)phenyl]-3-fluorobenzenesulfonamide, N-[2-[ethyl(phenylsulfonyl)amino]-4-(4-methyl-1-piperazinyl)phenyl] benzenesulfonamide, 3-fluoro-N-[2-{[(3-fluorophenyl)sulfonyl]amino}-4-(4-methyl-1-piperazinyl) phenyl]benzenesulfonamide, N-{5-(4-methyl-1-piperazinyl)-2-[(8-quinolinylsulfonyl)amino]phenyl}-7-quinolinesulfonamide, N-[2-chloro-4-({4-(4-methyl-1-piperazinyl)-2-[(phenylsulfonyl)amino]anilino}sulfonyl)phenyl]acetamide, 3,4-dimethoxy-N-{4-(4-methyl-1-piperazinyl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide, 3-methoxy-4-methyl-N-{4-(4-methyl-1-piperazinyl)-2-[(phenylsulfonyl)amino]phenyl}benzenesulfonamide, 4-methyl-N-{4-(4-methyl-1-piperazinyl)-2-[(methylsulfonyl)amino]phenyl}benzenesulfonamide, 3,4-dimethoxy-N-{4-(4-methyl-1-piperazinyl)-2-[(methylsulfonyl)amino]phenyl}benzenesulfonamide, 3-cyano-N-{4-(4-methyl-1-piperazinyl)-2-[(methylsulfonyl)amino]phenyl}benzenesulfonamide, N-{4-(1-piperazinyl)-2-[(phenylsulfonyl)amino]phenyl}-1-naphthalenesulfonamide, 5-(dimethylamino)-N-{4-(1-piperazinyl)-2-[(phenylsulfonyl)amino]phenyl}-1-naphthalenesulfonamide, N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]-8-quinolinesulfonamide, 2,4,6-trimethyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide, 4-methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl] benzenesulfonamide, N-[2-({[(E)-2-phenylethenyl]sulfonyl}amino)-5-(1-piperazinyl)phenyl]benzenesulfonamide, 2,5-dimethoxy-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl] benzenesulfonamide, 2-methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl] benzenesulfonamide, 2,4-difluoro-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl] benzenesulfonamide, 4-butoxy-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide, 3,5-dimethyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]-4-isoxazolesulfonamide, 5-fluoro-2-methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide, 4-(methylsulfonyl)-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide, 2-(methylsulfonyl)-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide, 2-methoxy-4-methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide, 4-methoxy-2-methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide, N-[2-amino-4-(1-piperazinyl)phenyl]-3-fluorobenzenesulfonamide, N-[2-(ethylamino)-4-(1-piperazinyl)phenyl]-3-fluorobenzenesulfonamide, 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)benzenesulfonamide 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-naphthalenesulfonamide 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 3-amino-N-(3-chlorophenyl)-4-(4-methyl-1-piperazinyl)benzenesulfonamide hydrochloride 3-amino-N-(2-methoxyphenyl)-4-(4-methyl-1-piperazinyl)benzenesulfonamide hydrochloride 3-amino-N-(2-methoxyphenyl)-4-(1-piperazinyl)benzenesulfonamide hydrochloride 3-amino-N-(2-methoxyphenyl)-4-(3-methyl-1-1piperazinyl)benzenesulfonamide hydrochloride 3-amino-4-(hexahydro-pyrrolo[1,2-α]pyrazin-2-yl)-N-(2-methoxyphenyl)-benzenesulfonamide hydrochloride 3-amino-N -phenyl-4-piperazin-1-yl-benzenesulfonamide hydrochloride 3-amino-4-(3-methyl-piperazin-1-yl)-N-phenyl-benzenesulfonamide hydrochloride 3-amino-4-(4-ethyl-piperazin-1-yl)-N-phenyl-benzenesulfonamide hydrochloride 3-amino-4-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-N-phenyl-benzenesulfonamide hydrochloride 3-amino-4-(5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-N-phenyl-benzenesulfonamide hydrochloride 3-amino-4-(trans -2,5-dimethyl-piperazin-1yl)-N-(2methoxy-phenyl)benzenesulfonamide hydrochloride 2-(3-amino-4-[1,4]diazepan-1-yl-benzenesulfonyl)-benzamide diacetic acid 4-[4-(3-fluoro-2-methoxy-phenylsulfamoyl)-2-amino-phenyl]-[1,4]diazepane ditrifluoroacetic acid 2-[1,4]diazepan-1-yl-5-(3,4-dihydro-1H-isoquinoline-2-sulfonyl)-aniline dihydrochioride 4-[4-(3,4-dihydro-2H-quinoline-1-sulfonyl)-2-amino-phenyl]-[1,4]diazepane ditrifluoroacetic acid; or 3-amino-2-chloro-N-naphthalen-1-yl-4-piperazin-1-yl-benzenesulfonamide, hydrochloride.
- Claim: 9. The method of claim 1 , wherein the method comprises administering the compound of formula I, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent or carrier.
- Claim: 10. A method for the treatment of type II diabetes, the method comprising administering to a subject in need thereof an effective amount of a compound of 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); 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 13 is (a) homopiperazine, (b) methylhomopiperazine, or (c) a group R 5 ; and 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: 11. The method of claim 10 , wherein R 13 is (a) homopiperazine, (b) methylhomopiperazine, or (c) a group R 5 selected from [chemical expression included] and R 8 is (a) H, or (b) C 1-6 alkyl, in particular methyl; 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: 12. The method of claim 10 , wherein the compound of formula (II) is: 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, N-[4-nitro-5-(piperazinyl)phenyl]benzenesulfonamide, or N-[4-amino-5-(piperazinyl)phenyl]benzenesulfonamide.
- Claim: 13. The method of claim 10 , wherein the method comprises administering the compound of formula II, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent or carrier.
- Claim: 14. A method for the treatment of type II diabetes, the method comprising administering to a subject in need thereof an effective amount of a compound of 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: 15. The method of claim 14 , wherein Ar is a 5 to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur.
- Claim: 16. The method of claim 14 , wherein Ar is isoxazolyl, benzoxadiazolyl, quinolinyl, or thienyl.
- Current U.S. Class: 51421/201
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