IP Library › Granted Patent US 7,259,165

Granted Patent B2

US 7,259,165 · App. 10/778,441 · Granted Aug 21, 2007

Heterocyclyl-3-sulfonylazaindole or-azaindazole derivatives as 5-hydroxytryptamine-6 ligands

Assignee: Wyeth

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 7,259,165
App. No.: 10/778,441
Granted: Aug 21, 2007
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

The present invention provides a compound of formula I and the use thereof for the treatment of a central nervous system disorder related to or affected by the 5-HT6 receptor.

Claims (108)

1. A compound of formula I

wherein

W is CR 2 ;

X is N or CR 4 ;

Y is N or CR 5 ;

Z is N or CR 6 ;

Q is N or CR 7 with the proviso that one and only one of X, Y, Z and Q must be N;

R 1 is an optionally substituted C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, aryl, or heteroaryl group or an optionally substituted 8- to 13-membered bicyclic or tricyclic ring system having a N atom at the bridgehead and optionally containing 1, 2 or 3 additional heteroatoms selected from N, O or S;

R 2 is H, halogen, or a C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 7 cycloalkyl, aryl or heteroaryl group each optionally substituted;

R 3 is H or a, C 3 -C 7 cycloalkyl, aryl or heteroaryl group each optionally substituted;

R 4 , R 5 , R 6 and R 7 are each independently H, halogen, CN, COR 8 , OCO 2 R 9 , CO 2 R 10 , CONR 11 R 12 , SO n R 13 , NR 14 R 15 , OR 16 or a C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, aryl or heteroaryl group each optionally substituted or a group M having the structure

with the proviso that at least one of R 4 , R 5 , R 6 or R 7 must be a group M and with the further proviso that when W is CR 2 and X or Z is N, then R 7 must be other than a group M;

R 8 , R 9 , R 10 and R 13 are each independently H or a C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted;

R 11 , R 12 , R 14 and R 15 are each independently H or an optionally substituted C 1 -C 4 alkyl group or R 11 and R 12 or R 14 and R 15 may be taken together with the atom to which they are attached to form a 5- to 7-membered ring optionally containing another heteroatom selected from O, NR 22 or SO n ;

R 16 is H or a C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted;

n is 0 or an integer of 1 or 2;

R 17 is H or a C 1 -C 6 alkyl or C 3 -C 7 cycloalkyl group each optionally substituted;

R 18 , R 19 , R 20 , R 21 and R 23 are each independently H or a C 1 -C 6 alkyl or C 3 -C 7 cycloalkyl group each optionally substituted;

m is 1 or 2; and

R 22 is H or a C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted; or

the stereoisomers thereof or the pharmaceutically acceptable salts thereof.

2. The compound according to claim 1 wherein m is 1.

3. The compound according to claim 1 wherein Y is CR 5 and R 5 is a group M.

4. The compound according to claim 2 wherein Y is CR 5 and R 5 is a group M.

5. The compound according to claim 2 wherein R 1 is an optionally substituted phenyl, naphthyl or heteroaryl group.

6. The compound according to claim 5 wherein R 5 or R 7 is a group M.

7. The compound according to claim 1 selected from the group consisting of:

5-(4-benzylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine;

5-(4-methylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine;

3-(phenylsulfonyl)-5-(4-propylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine;

3-(phenylsulfonyl)-5-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine;

3[-(3-cyanophenyl)sulfonyl]-5-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine;

5-(4-benzylpiperazin-1-yl)-3-[(1-naphthyl)sulfonyl]-1H-pyrrolo[3,2-c]pyridine;

5-(4-methylpiperazin-1-yl)-3-[(2-naphthyl)sulfonyl]-1H-pyrrolo[3,2-b]pyridine;

3-[(2-chloro-4-fluorophenyl)sulfonyl]-5-(4-propylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine;

1-methyl-3-(phenylsulfonyl)-5-piperazin-1-yl-1H-pyrrolo[3,2-b]pyridine;

1-phenyl-3-(phenylsulfonyl)-5-piperazin-1-yl-1H-pyrrolo[2,3-c]pyridine;

5-(4-benzylpiperazin-1-yl)-3-[(3-fluorophenyl)sulfonyl]-1H-pyrrolo[3,2-c]pyridine;

3-[(4-fluorophenyl)sulfonyl]-5-(4-methylpiperazin-1-yl)-1H-pyrrolo[3,2-b]pyridine;

3-[(2-chlorophenyl)sulfonyl]-5-(4-propylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine;

3-[(4-aminophenyl)sulfonyl]-5-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine;

2-methyl-3-(phenylsulfonyl)-5-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine;

4-chloro-3-(phenylsulfonyl)-5-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine;

7-fluoro-3-(phenylsulfonyl)-5-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine;

6-fluoro-3-(phenylsulfonyl)-5-piperazin-1-yl-1H-pyrrolo[2,3-c]pyridine;

6-(4-benzylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-pyrrolo[3,2-c]pyridine;

6-(4-methylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine;

3-(phenylsulfonyl)-6-(4-propylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine;

3-(phenylsulfonyl)-6-piperazin-1-yl-1H-pyrrolo[2,3-b]pyridine;

4-(4-benzylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine;

4-(4-methylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine; and

3-(phenylsulfonyl)-4-(4-propylpiperazin-1-yl)-1H-pyrrolo[3,2-c]pyridine; or

3-(phenylsulfonyl)-4-piperazin-1-yl-1H-pyrrolo[3,2-b]pyridine;

a stereoisomer thereof; or

a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and an effective amount of a compound of formula I