IP Library › Granted Patent US 6,903,112

Granted Patent B2

US 6,903,112 · App. 10/691,937 · Granted Jun 7, 2005

Heterocyclylindazole and -azaindazole compounds as 5-hydroxytryptamine-6 ligands

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Quick Facts

Patent No.: US 6,903,112
App. No.: 10/691,937
Granted: Jun 7, 2005
Kind: B2

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Abstract

The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of disorders related to or affected by the 5-HT6 receptor.

Claims (117)

1. A compound of formula I

wherein

Q is SO 2 ;

either W is N or CR 6 and X is N, or W is CR 6 and X is N or CR 7 ;

Y is NR 8 or CR 9 R 10 ;

n is an integer of 1;

Z is NR 11 or CR 12 R 13 with the proviso that when W is CR 6 then Z must be CR 12 R 13 and with the further provisos that when Y is NR 8 then Z must be CR 12 R 13 and at least one of Y and Z must be NR 8 or NR 11 ;

R 1 , R 2 and R 7 , are each independently H, halogen, CN, OCO 2 R 14 , CO 2 R 15 , CONR 29 R 30 , CNR 16 NR 17 R 18 , SO m R 19 , NR 20 R 21 , OR 22 , COR 23 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 3 , R 4 , R 9 , R 10 , R 12 and R 13 are each independently H or an optionally substituted C 1 -C 6 alkyl group;

R 5 is an optionally substituted C 1 -C 6 alkyl, aryl or heteroaryl group;

m is 0 or an integer of 1 or 2;

R 6 is H, halogen, or an optionally substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, aryl or heteroaryl group;

R 8 and R 11 are each independently H, CNR 26 NR 27 R 28 or a C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, cycloheteralkyl, aryl or heteroaryl group;

R 14 , R 15 , R 22 and R 23 are each independently H or an optionally substituted 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;

R 16 , R 17 , R 18 , R 20 , R 21 , R 26 , R 27 , R 28 , R 29 and R 30 are each independently H or C 1 -C 4 alkyl;

R 19 , is an optionally substituted C 1 -C 4 alkyl, aryl or heteroaryl group;

R 24 and R 25 are each independently H or an optionally substituted C 1 -C 6 alkyl, aryl or heteroaryl group; and represents a single bond or a double bond; or the stereoisomers thereof or the pharmaceutically acceptable salts thereof.

2. The compound according to claim 1 wherein Y is NR 8 .

3. The compound according to claim 1 wherein W is N.

4. The compound according to claim 3 wherein Z is NR 11 .

5. The compound according to claim 1 wherein Q is SO 2 and R 5 is an optionally substituted aryl or heteroaryl group.

6. The compound according to claim 5 wherein X is CH and represents a single bond.

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

1-benzenesulfonyl-3-piperidin-3-yl-1H-indole;

1-(4-isopropyl-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(5-chloro-thiophene-2-sulfonyl)-3-piperidin-3-yl-1H-indole;

1-(3-chloro-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(3,4-difluoro-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(4-trifluoromethoxy-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(4-methoxy-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(4-trifluoromethy-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(3-chloro-4-methyl-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(2-chloro-4-trifluoromethyl-benzenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(2-naphthylenesulfonyl)-3-piperidin-3-yl-1H-indole;

1-(5-chloro-3-methyl-benzo[b]thiophene-2-sulfonyl)-3-piperidin-3-yl-1H-indole;

1-(2,6-dichloro-imidazo[2,1-b]thiazole-5-sulfonyl)-3-piperidin-3-yl-1H-indole.

2-chloro-3-(3-piperidin-3-yl-indole-1-sulfonyl)-imidazo[1,2-a]pyridine;

2-chloro-3-(3-piperidin-3-yl-indole-1-sulfonyl)-benzo[d]imidazo[2,1-b]thiazole;

1-(4-isopropyl-benzenesulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(5-chloro-thiophene-2-sulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(3-chloro-benzenesulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(3,4-difluoro-benzenesulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(4-trifluoromethoxy-benzenesulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(3-chloro-4-methyl-benzenesulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(2-chloro-4-trifluoromethyl-benzenesulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(2-naphthylenesulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

1-(5-chloro-3-methyl-benzo[b]thiophene-2-sulfonyl)-3-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridine;

2-chloro-3-(3-piperidin-3-yl-pyrrolo[2,3-b]pyridine-1-sulfonyl)-imidazo[1,2-a]pyridine;

2-chloro-3-(3-piperidin-3-yl-pyrrolo[2,3-b]pyridine-1-sulfonyl)-benzo[d]imidazo[2,1-b]thiazole; and

the pharmaceutically acceptable salts thereof.

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

wherein

Q is SO 2 ;

either W is N or CR 6 and X is N, or W is Cr 6 and X is N or CR 7 ;

Y is NR 8 , or CR 9 R 10 ;

n is an integer of 1;

R 1 , R 2 and R 7 are each independently H, halogen, CN, OCO 2 R 14 , CO 2 R 15 , CONR 29 R 30 , CNR 16 NR 17 R 18 , SO m R 19 , NR 20 R 21 , OR 22 , COR 23 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 3 , R 4 , R 9 , R 10 , R 12 and R 13 are each independently H or an optionally substituted C 1 -C 6 alkyl group;

R 5 is an optionally substituted C 1 -C 6 alkyl, aryl or heteroaryl group;

m is 0 or an integer of 1 or 2;

R 6 is H, halogen, or an optionally substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, aryl or heteroaryl group;

R 8 and R 11 are each independently H, CNR 26 NR 27 R 28 or a C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, cycloheteralkyl, aryl or heteroaryl group;

R 14 , R 15 , R 22 and R 23 are each independently H or an optionally substituted 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;

R 16 , R 17 , R 18 , R 20 , R 21 , R 26 , R 27 , R 28 , R 29 , and R 30 are each independently H or C 1 -C 4 alkyl;

R 19 is an optionally substituted C 1 -C 6 alkyl, aryl or heteroaryl group;

9. The composition according to claim 8 having a formula I compound wherein n is 1; Q is SO 2 ; Y is NR 8 ; and X is CR 7 .

10. The composition according to claim 8 having a formula I compound wherein Q is SO 2 ; X is CR 7 ; and Z is NR 11 .

11. The composition according to claim 9 having a formula I compound wherein R 5 is an optionally substituted aryl group and represents a single bond.

12. The composition according to claim 8 having a formula I compound selected from the group consisting of: