US2010222330A1PendingUtilityA1

New Compounds

46
Assignee: BIOVITRUM ABPriority: Jun 11, 2001Filed: May 17, 2010Published: Sep 2, 2010
Est. expiryJun 11, 2021(expired)· nominal 20-yr term from priority
A61P 7/00A61P 43/00A61P 3/10C07D 295/096C07D 243/08C07D 295/135A61P 25/00C07D 487/04A61P 25/20C07D 307/79C07D 333/34C07D 241/04C07D 217/22A61P 3/04A61K 31/495A61P 25/16A61P 25/14A61P 25/24A61P 25/22A61P 25/18A61K 31/4965C07D 413/12C07D 215/38C07D 487/08A61P 25/28A61P 25/30A61P 25/06C07D 215/40C07D 471/04C07D 409/12C07D 307/78C07D 319/18
46
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Claims

Abstract

The present invention relates to substituted sulfonamide compounds of the general formula (I), wherein P is sulfonamide or amide-substituted sulfonic acid, which compounds are potentially useful for the prophylaxis and treatment of medical conditions relating to obesity, type II diabetes and/or disorders of the central nervous system.

Claims

exact text as granted — not AI-modified
1 . A compound of the formula I 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         ring B is 
       
       
         
           
           
               
               
           
         
       
       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 N or —(CH)—, provided that not more than three groups W are N in both rings A and B together; 
 P is 
 
       
         
           
           
               
               
           
         
         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 
       
       
         
           
           
               
               
           
         
         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 , or 
         (ab) —S(O) n R 4 ; wherein n is 0, 1, 2 or 3; 
         (ac) —S—(C 1-6 )alkyl 
         (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. 
       
     
     
         2 . The compound according to  claim 1  of the general formula II 
       
         
           
           
               
               
           
         
         wherein R 3 , P, X and Y are as defined for formula (I). 
       
     
     
         3 . The compound according to  claim 1  of the general formula III 
       
         
           
           
               
               
           
         
         wherein R 3 , P, X and Y are as defined for formula (I). 
       
     
     
         4 . The compound according to  claim 1  of the general formula IV 
       
         
           
           
               
               
           
         
         wherein R 3 , P, X and Y are as defined for formula (I). 
       
     
     
         5 . The compound according to  claim 1  of the general formula V 
       
         
           
           
               
               
           
         
         wherein R 3 , P, X and Y are as defined for formula (I). 
       
     
     
         6 . The compound according to  claim 1  of the general formula VI 
       
         
           
           
               
               
           
         
         wherein R 3 , P, X and Y are as defined for formula (I); 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. 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). 
       
     
     
         7 . 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, in particular methyl;   or R 1  and R 2  are linked to form a group (CH 2 ) 4 O;   R 3  is   
       
         
           
           
               
               
           
         
         
           wherein R 6  is 
           (a) H, or 
           (b) C 1-6  alkyl, in particular methyl; 
         
         X and Y are H; and/or 
         D is pyrrolyl, thienyl or furanyl. 
       
     
     
         8 . The compound according to  claim 1 , which is the compound
 N-(4-Methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   N-(2,4-Dimethoxyphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   N-(3,4-di-Fluorophenyl)-4-(4-methyl-1,4-diazepan-1-yl)-1-naphthalenesulfonamide, hydrochloride   N-(3-Fluorophenyl)-4-(4-methyl-1,4-diazepan-1-yl)-1-naphthalenesulfonamide, hydrochloride   4-(4-Ethyl-1-piperazinyl)-N-phenyl-1-naphthalenesulfonamide, hydrochloride   4-Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl-N-(4-methylphenyl)-1-naphthalenesulfonamide, hydrochloride   N-(3,4-Dimethoxyphenyl)-4-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl-1-naphthalenesulfonamide, hydrochloride   4-(4-Ethyl-1-piperazinyl)-N-(4-methylphenyl)-1-naphthalenesulfonamide, hydrochloride   N-(3,4-Dimethoxyphenyl)-4-(3-methyl-1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   N-(4-Methylphenyl)-4-(4-methyl-1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   N-[4-(2,5-Diazabicyclo[2.2.1]hept-2-yl)-1-naphthyl]-4-methylbenzenesulfonamide, hydrochloride   N-(4-Methylphenyl)-4-(3-methyl-1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   N-(2-Naphthyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   N-Methyl-N-(4-methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   4-(1,4-Diazepan-1-yl)-N-(4-methylphenyl)-1-naphthalenesulfonamide, hydrochloride   4-(1,4-Diazepan-1-yl)-N-(2-methoxy-4-methylphenyl)-1-naphthalenesulfonamide, hydrochloride   N-(2-Methoxy-4-methylphenyl)-4-(3,5-trimethyl-1-piperazinyl)-1-naphthalenesulfonamide, hydrochloride   4-(4-Isopropyl-1-piperazinyl)-N-(4-methylphenyl)-1-naphthalenesulfonamide, hydrochloride   4-Bromo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   2,5-di-Chloro-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide, hydrochloride   2-Chloro-4-fluoro-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide, hydrochloride   2,3-di-Chloro-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide, hydrochloride   2,4-di-Chloro-5-methyl-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide, hydrochloride   3-tri-Fluoromethyl-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide, hydrochloride   2-tri-Fluoromethyl-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide, hydrochloride   4-Bromo-N-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   Naphthalene-1-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide, hydrochloride   Naphthalene-1-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide, hydrochloride   2,5-Dichloro-thiophene-3-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide, hydrochloride   4-Methoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   4-Chloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   2-Chloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   N-(4-piperazin-1-yl-naphthalen-1-yl)-4-trifluoromethyl-benzenesulfonamide, hydrochloride   4-Fluoro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   5-Fluoro-2-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   4-Phenoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   2-Bromo-4-iodo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   Thiophene-2-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide, hydrochloride   5-Chloro-thiophene-2-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide, hydrochloride   3-Methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   4-Butyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide hydrochloride   2,4,6-Trimethyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide hydrochloride   2,4,5-Trichloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   4-Iodo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   2-Methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   3,4-Dichloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   5-Bromo-2-methoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   2-Bromo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   3-Chloro-2-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   2,6-Dichloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   3-Methoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   3-Chloro-4-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   4-Bromo-2-fluoro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   2,4-Dichloro-6-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   4-Bromo-2-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide, hydrochloride   4,5-Dichloro-thiophene-2-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide, hydrochloride   N-Methyl-N-(4-bromo-2-methylphenyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   N-Methyl-N-(5-fluoro-2-methylphenyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   N-Methyl-N-(2-methylphenyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   N-Methyl-N-(3-chloro-2-methylphenyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   2,5-di-Chlorothiophen-3-yl-N-Methyl-N-(2,5-dichlorothiophen-3-yl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   N-Methyl-N-(2-naphthyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   N-Methyl-N-(1-naphthyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   N-Methyl-N-(4-chlorophenyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   N-Methyl-N-(4-methoxyphenyl)-4-(1-pyperazinyl)-1-napthalenesulphonamide, hydrochloride   5-Fluoro-2-methyl-N-{4-[(2R,5S)-2,5-dimethyl-1-]piperazin-1-yl-1-naphthyl}benzenesulfonamide, hydrochloride   5-Fluoro-2-methyl-N-[4-(1,2,3,6-tetrahydropyridin-4-yl)-1-naphthyl]benzenesulfonamide, hydrochloride   N-[4-(4-Methyl-1-piperazinyl)-2-naphthyl]benzenesulfonamide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid phenylamide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2-methoxy-phenyl)-amide, hydrochloride   4-(cis-3,5-Dimethyl-piperazin-1-yl)-naphthalene-1-sulfonic acid (2-methoxy-phenyl)-amide, hydrochloride   4-(cis-3,5-Dimethyl-piperazin-1-yl)-naphthalene-1-sulfonic acid (3-chloro-phenyl)-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-chloro-phenyl)-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid phenylamide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-chloro-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2-methylsulfanyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid methyl-naphthalen-1-yl-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2,3-dihydro-benzo[1,4]dioxin-6-yl)-methyl-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid methyl-(2-methylsulfanyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid methyl-(3-trifluoromethyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-chloro-4-methyl-phenyl)-methyl-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-ethyl-phenyl)-methyl-amide, hydrochloride   4-(3,5-Dimethyl-piperazin-1-yl)-naphthalene-1-sulfonic acid (2-isopropyl-phenyl)-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2-isopropyl-phenyl)-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-ethyl-phenyl)-amide, hydrochloride   N-(2-Fluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide, hydrochloride   4-[1,4]-Diazepan-1-yl-naphthalene-1-sulfonic acid (3-trifluoromethyl-phenyl)-amide, hydrochloride   N-(2,4-di-Fluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2-trifluoromethoxy-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-3-phenoxyphenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-trifluoromethoxy-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2-chloro-5-methyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-trifluoromethoxy-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2-chloro-5-methyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (4-isopropyl-phenyl)-amide, hydrochloride   N-(3,5-di-Fluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide, hydrochloride   1-[4-(3,4-Dihydroquinolin-1(2H)-ylsulfonyl)-1-naphthyl]piperazine, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-nitro-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-nitro-phenyl)-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-nitro-phenyl)-methyl-amide, hydrochloride   N-(4-Methylphenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide, hydrochloride   N-(3-Chloro-4-methylphenyl-4-piperazin-1-ylnaphthalene-1-sulfonamide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2,3-dimethyl-phenyl)-methyl-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (4-isopropyl-phenyl)-amide, hydrochloride   4-[1,4]-Diazepan-1-yl-naphthalene-1-sulfonic acid (4-isopropyl-phenyl)-methyl-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2,4-dimethyl-phenyl)-amide, hydrochloride   4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2-chloro-5-methyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2,5-dimethoxy-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-acetyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (2,4-dimethyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-trifluoromethyl-phenyl)-amide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid biphenyl-2-ylamide, hydrochloride   4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-benzyloxy-phenyl)-amide, hydrochloride   N-(4-fluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide, hydrochloride   N-(3-Ethylphenyl)-4-piperazin.1.ylnaphthalene-1-sulphonamine, hydrochloride   4-piperazinyl-N-[3-(trifluoromethyl)phenyl]naphthalene-1-sulfonamide, hydrochloride   4-piperazinyl-N-[3-benzoylphenyl]naphthalene-1-sulfonamide, hydrochloride   4-Piperazinyl-N-[3-(4-bromo-1-methyl-1H-pyrazol-3-yl)phenyl]naphthalene-1-sulfonamide, hydrochloride   4-piperazinyl-N-[3-biphenylphenyl]naphthalene-1-sulfonamide, hydrochloride   
     
     
         9 . The compound according to  claim 1 , which is the compound
 N-[1-(4-Methyl-1-piperazinyl)-3-isoquinolinyl]benzenesulfonamide, hydrochloride   2,4-di-Fluoro-N-[1-(4-methyl-1-piperazinyl)-3-isoquinolinyl]benzenesulfonamide, hydrochloride   4-Bromo-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonic acid [1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-amide, hydrochloride   3-Chloro-2-methyl-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   3,4-Dichloro-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   4-Methyl-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   3-Methoxy-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   5-Chloro-thiophene-2-sulfonic acid [1-(4-methyl-piperazin-1-yl]-amide, hydrochloride   N-{2-Chloro-4-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-ylsulfamoyl]-phenyl}-acetamide hydrochloride   2,5-Dichloro-thiophene-3-sulfonic acid [1-(4-methyl-piperazin-1-yl)-isoquinol n-3-yl]-amide, hydrochloride   N-[1-(4-Methyl-piperazin-1-yl)-isoquinolin-3-yl]-3-trifluoromethyl-benzenesulfonamide, hydrochloride   N-[1-(4-Methyl-piperazin-1-yl)-isoquinolin-3-yl]-4-phenoxy-benzenesulfonamide, hydrochloride   5-Bromo-2-methoxy-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   2-Methanesulphonayl-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   3,5-Dimethyl-isoxazole-4-sulfonic acid [1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-amide, hydrochloride   2,4,6-Trimethyl-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   3,4-Dimethoxy-N-[1-(4-methyl-piperazin-1-yl)-isoquinolin-3-yl]-benzenesulfonamide, hydrochloride   
     
     
         10 . The compound according to  claim 1 , which is the compound
 N-(8-{[2-(di-Methylamino)ethyl]amino}-5-quinolinyl)benzenesulfonamide, hydrochloride   
     
     
         11 . The compound according to  claim 1 , which is the compound
 4-Methyl-N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)benzenesulfonamide, trifluoroacetic acid   4-Bromo-N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)benzenesulfonamide, trifluoroacetic acid   N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)naphthalene-1-sulfonamide, trifluoroacetic acid   N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)butane-1-sulfonamide, trifluoroacetic acid   3-Trifluoromethyl-N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)benzenesulfonamide, trifluoroacetic acid   3,4-Dimethoxy-N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)benzenesulfonamide, trifluoroacetic acid   2,4-Dichloro-N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)benzenesulfonamide, trifluoroacetic acid   N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)thiophene-2-sulfonamide, trifluoroacetic acid   1-Phenyl-N-(8-piperazin-1-yl-1,7-naphthyridin-6-yl)methanesulfonamide, trifluoroacetic acid   
     
     
         12 . 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   N-[7-(4-Methylpiperazin-1-yl)-1-benzofuran-5-yl]-benzenesulfonamide, hydrochloride   
     
     
         13 . A process for the preparation of a compound according to  claim 1 , wherein P is 
       
         
           
           
               
               
           
         
       
       said method comprising the steps of:
 (a) nucleophilic aromatic substitution of the aromatic halogen atom in 1-chloro-3-nitronaphthalene or 1-chloro-4-nitronaphthalene with aliphatic or aromatic diamines; 
 (b) reduction of the nitro group in 1-diamine-3-nitronaphthalene or 1-diamine-4-nitronaphthalene obtained in step (a) to form 1-diamine-3-NH 2 -naphthalene or 1-diamine-4-NH 2 -naphthalene, respectively; and 
 (c) synthesis of a sulfonamide by reacting 1-diamine-3-NH 2 -naphthalene or 1-diamine-4-NH 2 -naphthalene obtained in step (b) with a suitable sulfonyl chloride. 
 
     
     
         14 . The process of  claim 13 , wherein step (a) is by means of Palladium catalyzed nucleophilic substitution. 
     
     
         15 . A process for the preparation of a compound according to  claim 1 , wherein P is 
       
         
           
           
               
               
           
         
       
       said method comprising the steps of:
 (a) nucleophilic aromatic substitution of the trifluoromethanesulfonate group in 2-trifluoromethansulfonate-5-nitroquinoline with aliphatic or aromatic diamines; 
 (b) reduction of the nitro group in 2-diamine-5-nitroquinoline obtained in step (a) to form 2-diamine-5-NH 2 -quinoline; and 
 (c) synthesis of a sulfonamide by reacting 2-diamine-5-NH 2 -quinoline obtained in step (b) with a suitable sulfonyl chloride. 
 
     
     
         16 . A process for the preparation of a compound according to  claim 1 , wherein P is 
       
         
           
           
               
               
           
         
       
       said method comprising the steps of:
 (a) reacting a fluoronaphthalene and chlorosulfonic acid under acidic conditions, to introduce a sulfonyl chloride group in the para position to the carbon having the fluoro atom; 
 (b) reacting the product of step (a) with an aliphatic or aromatic primary amine to give a sulphonamide; and 
 (c) reaction of the product of step (b) with a diamine. 
 
     
     
         17 . A pharmaceutical formulation containing a compound according to  claim 1  as active ingredient, in combination with a pharmaceutically acceptable diluent or carrier. 
     
     
         18 . A method for the treatment or prophylaxis of obesity, type II diabetes, and/or disorders of the central nervous system, which comprises administering to a mammalin need of such treatment an effective amount of a compound according to  claim 1 . 
     
     
         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 1 . 
     
     
         20 . A method for modulating 5-HT 6  receptor activity, comprising administering to a subject in need thereof an effective amount of a compound according to  claim 1 .

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