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Substituted naphthalene sulfonamides

Caldirola, Patrizia ; Bremberg, Ulf ; et al.
2009
Online Patent

Titel:
Substituted naphthalene sulfonamides
Autor/in / Beteiligte Person: Caldirola, Patrizia ; Bremberg, Ulf ; Johansson, Gary ; Mott, Andrew ; Jensen, Annika Jenmalm ; Beierlien, Katarina ; Thor, Markus ; Tedenborg, Lars
Link:
Veröffentlichung: 2009
Medientyp: Patent
Sonstiges:
  • Nachgewiesen in: USPTO Patent Grants
  • Sprachen: English
  • Patent Number: 7,572,787
  • Publication Date: August 11, 2009
  • Appl. No: 11/510324
  • Application Filed: August 25, 2006
  • Assignees: Biovitrum AB (Stockholm, SE)
  • Claim: 1. A compound of the formula II: [chemical expression included] or a pharmaceutically acceptable salt thereof, wherein: 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 optionally substituted in one or more positions 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 2-4 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) —NR 4 R 5 , (p) —NO 2 , (q) —CONR 4 R 5 , (r) —NHSO 2 R 4 , (s) —NR 4 COR 5 , (t) —SO 2 NR 4 R 5 , (u) —C(═O)R 4 , (v) —CO 2 R 4 , (w) —S(O) n R 4 , wherein n is 0, 1, 2 or 3, (x) —S—(C 1-6)alkyl, (y) —SCF 3 , and (z) 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; R 3 is a group selected from the group consisting of [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 2-4 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) —NR 4 R 5 , (q) —NO 2 , (r) —CONR 4 R 5 , (s) —NHSO 2 R 4 , (t) —NR 4 COR 5 , (u) —SO 2 NR 4 R 5 , (v) —C(═O)R 4 , (w) —CO 2 R 4 , (x) —S(O) n R 4 ; wherein n is 0, 1, 2 or 3; (y) —S—(C 1-6)alkyl, or (z) —SCF 3 ; each R 4 and R 5 independently (a) H, (b) C 1-6 alkyl, (c) C 3-7 cycloalkyl, or (d) Ar 1 ; wherein Ar 1 is selected from the group consisting of (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, and (g) a bicyclic ring system comprising at least one heterocyclic ring according to (f); wherein the group Ar 1 is optionally substituted in one or more positions 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 2-4 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) —NR 6 R 7 , (p) —NO 2 , (q) —CONR 7 R 8 , (r) —NHSO 2 R 7 , (s) —NR 7 COR 8 , (t) —SO 2 NR 7 R 8 , (u) —C(═O)R 7 , (v) —CO 2 R 7 , (w) —S(O) n R 7 , wherein n is 0, 1, 2 or 3, (x) —S—(C 1-6)alkyl, (y) —SCF 3 ; and (z) 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; wherein each R 7 and R 8 is independently (a) H, (b) C 1-6 alkyl, or (c) C 3-7 cycloalkyl; alternatively, R 4 and R 5 are linked to form a group (CH 2) 3-5 ; and R 6 is (a) H, or (b) straight or branched C 1-6 alkyl.
  • Claim: 2. The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, 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 optionally substituted in one or more positions with substituents selected from the group consisting of (a) halogen, (b) C 1-6 alkyl, (c) —CF 3 , (d) C 1-6 alkoxy, (e) C 2-4 alkenyl, (f) —OCF 3 , or (g) straight or branched C 1-6 hydroxyalkyl; R 2 is (a) H, or (b) C 1-3 alkyl; and R 3 is [chemical expression included] wherein R 6 is (a) H, or (b) C 1-6 alkyl.
  • Claim: 3. A compound according to claim 2 , or a pharmaceutically acceptable salt thereof, wherein: R 2 is H or methyl; and R 6 is H or methyl.
  • Claim: 4. The compound according to claim 1 , wherein the compound is selected from the group consisting of: N-(4-Methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-(3,4-Dimethoxyphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-(3,4-Difluorophenyl)-4-(4-methyl-1,4-diazepan-1-yl)-1-naphthalenesulfonamide; N-(3-Fluorophenyl)-4-(4-methyl-1,4-diazepan-1-yl)-1-naphthalenesulfonamide; 4-(4-Ethyl-1-piperazinyl)-N-phenyl-1-naphthalenesulfonamide; 4-Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl-N-(4-methylphenyl)-1-naphthalenesulfonamide; N-(3,4-Dimethoxyphenyl)-4-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl-1-naphthalenesulfonamide; 4-(4-Ethyl-1-piperazinyl)-N-(4-methylphenyl)-1-naphthalenesulfonamide; N-(4-Methylphenyl)-4-(4-methyl-1-piperazinyl)-1-naphthalenesulfonamide; N-[4-(2,5-Diazabicyclo[2.2.1]hept-2-yl)-1-naphthyl]-4-methylbenzenesulfonamide; N-(2-Naphthyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(4-methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; 4-(1,4-Diazepan-1-yl)-N-(4-methylphenyl)-1-naphthalenesulfonamide 4-(1,4-Diazepan-1-yl)-N-(2-methoxy-4-methylphenyl)-1-naphthalenesulfonamide; N-(4-methylphenyl)-4-(3,5-dimethyl-1-piperazinyl)-1-naphthalenesulfonamide; 4-(4-Isopropyl-1-piperazinyl)-N-(4-methylphenyl)-1-naphthalenesulfonamide; 4-Bromo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2,5-Dichloro-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide; 2-Chloro-4-fluoro-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide; 2,3-Dichloro-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide; 2,4-Dichloro-5-methyl-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide; 3-Trifluoromethyl-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide; 2-Trifluoromethyl-N-[4-(1-piperazinyl)-1-naphthyl]benzenesulfonamide; 4-Bromo-N-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; Naphthalene-1-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide; 2,5-Dichloro-thiophene-3-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide; 4-Methoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 4-Chloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2-Chloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; N-(4-Piperazin-1-yl-naphthalen-1-yl)-4-trifluoromethyl-benzenesulfonamide; 4-Fluoro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 5-Fluoro-2-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 4-Phenoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2-Bromo-4-iodo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; Thiophene-2-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide; 5-Chloro-thiophene-2-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide; 3-Methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 4-Butyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2,4,6-Trimethyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2,4,5-Trichloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 4-Iodo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2-Methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 3,4-Dichloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 5-Bromo-2-methoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2-Bromo-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 3-Chloro-2-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2,6-Dichloro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 3-Methoxy-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 3-Chloro-4-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 4-Bromo-2-fluoro-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 2,4-Dichloro-6-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 4-Bromo-2-methyl-N-(4-piperazin-1-yl-naphthalen-1-yl)-benzenesulfonamide; 4,5-Dichloro-thiophene-2-sulfonic acid (4-piperazin-1-yl-naphthalen-1-yl)-amide; N-Methyl-N-(4-bromo-2-methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(5-fluoro-2-methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(2-methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(3-chloro-2-methylphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(2,5-dichlorothiophen-3-yl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(2-naphthyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(1-naphthyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(4-chlorophenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; N-Methyl-N-(4-methoxyphenyl)-4-(1-piperazinyl)-1-naphthalenesulfonamide; 5-Fluoro-2-methyl-N-{4-[(2R,5S)-2,5-dimethyl-1-]piperazin-1-yl-1-naphthyl}benzenesulfonamide; 5-Fluoro-2-methyl-N-[4-(1,2,3,6-tetrahydropyridin-4-yl)-1-naphthyl]benzenesulfonamide; N-[4-(4-Methyl-1-piperazinyl)-2-naphthyl]benzenesulfonamide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid phenylamide; 4-piperazin-1-yl-naphthalene-1-sulfonic acid (2-methoxy-phenyl)-amide; 4-(cis-3,5-Dimethyl-piperazin-1-yl)-naphthalene-1-sulfonic acid (2-methoxyphenyl)-amide; 4-(cis-3,5-Dimethyl-piperazin-1-yl)-naphthalene-1-sulfonic acid (3-chlorophenyl)-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-chloro-phenyl)-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid phenylamide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (3-chloro-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (2-methylsulfanyl-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (2,3-dihydro-benzo[1,4]dioxin-6-yl)-methyl-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid methyl-(2-methylsulfanyl-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid methyl-(3-trifluoromethyl-phenyl)-amide; 4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-chloro-4-methyl-phenyl)-methyl-amide; 4-piperazin-1-yl-naphthalene-1-sulfonic acid (3-ethyl-phenyl)-methyl-amide; 4-(3,5-Dimethyl-piperazin-1-yl)-naphthalene-1-sulfonic acid (2-isopropylphenyl)-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2-isopropyl-phenyl)-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-ethyl-phenyl)-amide; N-(2-Fluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-trifluoromethyl-phenyl)-amide; N-(2,4-Difluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (2-trifluoromethoxy-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (3-phenoxyphenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (3-trifluoromethoxy-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (2-chloro-5-methyl-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (4-isopropyl-phenyl)-amide; N-(3,5-Difluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide; 1-[4-(1,2,3,4-Tetrahydroquinolin-1(2H)-ylsulfonyl)-1-naphthyl]piperazine; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-nitro-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (3-nitro-phenyl)-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (3-nitro-phenyl)-methyl-amide; N-(4-Methylphenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide; N-(3-Chloro-4-methylphenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2,3-dimethyl-phenyl)-methyl-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (4-isopropyl-phenyl)-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (4-isopropyl-phenyl)-methyl-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2,4-dimethyl-phenyl)-amide; 4-[1,4]Diazepan-1-yl-naphthalene-1-sulfonic acid (2-chloro-5-methyl-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (2,5-dimethoxy-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (3-acetyl-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (2,4-dimethyl-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (3-trifluoromethyl-phenyl)-amide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid biphenyl-2-ylamide; 4-Piperazin-1-yl-naphthalene-1-sulfonic acid (3-benzyloxy-phenyl)-amide; N-(4-fluorophenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide; N-(3-Ethylphenyl)-4-piperazin-1-ylnaphthalene-1-sulfonamide; 4-Piperazinyl-N-[3-(trifluoromethylsulfanyl)phenyl]naphthalene-1-sulfonamide 4-Piperazinyl-N-[3-benzoylphenyl]naphthalene-1-sulfonamide; 4-Piperazinyl-N-[3-(4-bromo-1-methyl-1H-pyrazol-3-yl)phenyl]naphthalene-1-sulfonamide; and 4-Piperazinyl-N-[biphenyl-3-yl]naphthalene-1-sulfonamide; and pharmaceutically acceptable salts thereof.
  • Claim: 5. A compound selected from the group consisting of: N-(3,4-Dimethoxyphenyl)-4-(3-methyl-1-piperazinyl)-1-naphthalenesulfonamide; N-(4-Methylphenyl)-4-(3-methyl-1-piperazinyl)-1-naphthalenesulfonamide; and pharmaceutically acceptable salts thereof.
  • Claim: 6. A process for the preparation of a compound according to claim 1 , wherein P is [chemical expression included] said method comprising the steps of: (a) performing a nucleophilic aromatic substitution of the aromatic halogen atom in 1-chloro-3-nitronaphthalene or 1-chloro-4-nitronaphthalene with an aliphatic diamine; (b) reducing the nitro group in 1-diamine-substituted 3-nitronaphthalene or 4-nitronaphthalene obtained in step (a) to form 1-diamine-substituted 3-aminonaphthalene or -4-aminonaphthalene, respectively; and (c) reacting the 1-diamine-substituted 3-aminonaphthalene or -4-aminonaphthalene obtained in step (b) with a suitable sulfonyl chloride.
  • Claim: 7. The process of claim 6 , wherein step (a) is performed by means of Palladium catalyzed nucleophilic substitution.
  • Claim: 8. A process for the preparation of a compound according to claim 1 , wherein P is [chemical expression included] 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 sulfonamide; and (c) reacting the product of step (b) with a diamine.
  • Claim: 9. A pharmaceutical formulation containing a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, as an active ingredient, in combination with a pharmaceutically acceptable diluent or earner.
  • Claim: 10. A method for the treatment of obesity and/or type II diabetes, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.
  • Claim: 11. 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 , or a pharmaceutically acceptable salt thereof.
  • Claim: 12. A method for the treatment of a disorder of the central nervous system, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the disorder of the central nervous system is selected from the group consisting of panic attacks, memory disorders, sleep disorders, migraine, anorexia, bulimia, binge disorders, obsessive compulsive disorders, psychoses, Alzheimer's disease, Parkinson's disease, Huntington's chorea, schizophrenia, attention deficit hyperactive disorders, and drug abuse.
  • Claim: 13. A method for the treatment of a disorder of the central nervous system, which comprises administering to a mammal in need of such treatment an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the disorder of the central nervous system is selected from the group consisting of anxiety and depression.
  • Current U.S. Class: 514/218
  • Patent References Cited: 4808595 February 1989 Hoffman, Jr. ; 2004/0024210 February 2004 Johansson et al. ; 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 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 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: Methvin, Issac 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 ; STN International, file Caplus, Caplus Accession No. 1970:509549, document No. 73:109549, Werbel, Leslie M. et al., Synthetic schistosomicide, J. Med. Chem, vol. 13, No. 4, pp. 592-598, (1970). cited by other
  • Primary Examiner: Coleman, Brenda L
  • Attorney, Agent or Firm: Fish & Richardson P.C.

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