IP Library Granted Patent US 8,076,326
Granted Patent B2
US 8,076,326 · App. 12/770,837 · Granted Dec 13, 2011

N-phenyl- (piperazinyl or homopiperazinyl)-benzenesulfonamide or benzenesulfonyl-phenl-(piperazine or homopiperazine) compounds suitable for treating disorders that respond to modulation of the serotonin 5-HT

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Quick Facts
Patent No.
US 8,076,326
App. No.
12/770,837
Granted
Dec 13, 2011
Kind
B2
Abstract

The present invention relates to N-phenyl-(piperazinyl or homopiperazinyl)-benzenesulfonamide or benzenesulfonyl-phenyl-(piperazine or homopiperazine) compounds, pharmaceutical compositions containing them, and their use in therapy. The compounds possess valuable therapeutic properties and are particularly suitable for treating diseases that respond to modulation of the serotonin 5-HT 6 receptor. wherein X is a bond or a group N—R 4 ; R 1 is hydrogen or methyl; R 2 is hydrogen or methyl; R 3 is hydrogen, C 1 -C 3 alkyl, fluorine, C 1 -C 2 alkoxy or fluorinated C 1 -C 2 alkoxy; R 4 is hydrogen, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, or C 3 -C 4 cycloalkyl-CH 2 —; R 5 is hydrogen, fluorine, chlorine, C 1 -C 2 alkyl, fluorinated C 1 -C 2 alkyl, C 1 -C 2 alkoxy or fluorinated C 1 -C 2 alkoxy; R 6 is hydrogen, fluorine or chlorine; and n is 1 or 2.

Claims (46)

1. N-Phenyl-(piperazinyl or homopiperazinyl)-benzenesulfonamide or benzenesulfonyl-phenyl-(piperazine or homopiperazine) of formula (I) or (I′)

wherein

X is a bond or a group N-R 4;

R 1 is hydrogen or methyl;

R 2 is hydrogen or methyl;

R 3 is hydrogen, C 1 -C 3 alkyl, fluorine, C 1 -C 2 alkoxy or fluorinated C 1 -C 2 alkoxy;

R 4 is hydrogen, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, or C 3 -C 4 cycloalkyl-CH 2 -;

R 5 is hydrogen, fluorine, chlorine, C 1 -C 2 alkyl, fluorinated C 1 -C 2 alkyl, C 1 -C 2 alkoxy or fluorinated C 1 -C 2 alkoxy;

R 6 is hydrogen, fluorine or chlorine; and

n is 1 or 2,

or a physiologically tolerated acid addition salt or an N-oxide thereof.

2. The compound as claimed in claim 1 , wherein R 5 is hydrogen, fluorine, C 1 -C 2 alkyl, fluorinated C 1 -C 2 alkyl, C 1 -C 2 alkoxy or fluorinated C 1 -C 2 alkoxy.

3. The compound of claim 1 , where R 1 is hydrogen.

4. The compound of claim 1 , wherein R 2 is hydrogen.

5. The compound of claim 1 , wherein R 2 is methyl.

6. The compound of claim 1 , wherein X is a group N—R 4 .

7. The compound of claim 1 , wherein n is 1.

8. The compound of claim 1 , wherein R 3 is methyl or methoxy.

9. The compound of claim 1 , wherein R 3 is hydrogen or fluorine.

10. The compound of claim 1 , wherein R 4 is hydrogen, C 1 -C 4 alkyl or cyclopropylmethyl.

11. The compound of claim 1 , wherein R 4 is hydrogen.

12. The compound of claim 1 , wherein R 5 is hydrogen.

13. The compound of claim 1 , wherein R 5 is methyl, methoxy or difluoromethoxy.

14. The compound of claim 1 , wherein R 5 is chlorine or fluorine.

15. The compound of claim 1 , wherein R 6 is hydrogen.

16. The compound of claim 1 , wherein R 5 and R 6 are hydrogen, R 3 is selected from the group consisting of C 1 -C 2 alkyl and C 1 -C 2 alkoxy, and R 4 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, or cyclopropylmethyl.

17. The compound of claim 1 , wherein

X is a bond or a group N—R 4 ;

R 1 is hydrogen or methyl;

R 2 is hydrogen;

R 3 is hydrogen, C 1 -C 2 alkyl, C 1 -C 2 alkoxy ;

R 4 is hydrogen, methyl, ethyl, n-propyl, isopropyl or cyclopropylmethyl;

R 5 is hydrogen, methyl or methoxy;

R 6 is hydrogen; and

n is 1 or 2.

18. The compound of claim 17 , wherein R 3 is methyl.

19. The compound of claim 18 , wherein R 5 is hydrogen.

20. The compound of claim 19 , wherein R 4 is hydrogen.

21. The compound of claim 20 , wherein R 1 is hydrogen.

22. The compound of claim 21 , wherein X is a group N—R 4 .

23. The compound of claim 22 , wherein n is 1.

24. The compound of claim 23 , wherein the OCHF 2 -radical in formula I is located on the benzene ring in the ortho-position with respect to X.

25. The compound of claim 23 , wherein the OCHF 2 -radical in formula I is located on the benzene ring in the meta-position with respect to X.

26. The compound of claim 23 , wherein the OCHF 2 -radical in formula I is located on the benzene ring in the para-position with respect to X.

27. A pharmaceutical composition comprising at least one compound of claim 1 , optionally together with at least one physiologically acceptable carrier or auxiliary substance.

28. A non-prophylactic method for treating acute or chronic signs, symptoms and/or malfunctions of a disorder selected from diseases of the central nervous system or obesity, said method comprising administering an effective amount of at least one compound of claim 1 to a subject in need thereof, wherein said disease of the central nervous system is a cognitive dysfunction associated with Alzheimer's Disease or schizophrenia.

Assignments (5)
CORRECTIVE ASSIGNMENT TO REMOVE THE RECORDAL OF US PATENT 6589960 PREVIOUSLY RECORDED ON REEL 030237 FRAME 0947. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 13, 2014
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 032446/0551 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2013
From: ABBOTT GMBH & CO KG
To: ABBVIE DEUTSCHLAND GMBH & CO KG
Reel/Frame 030805/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030237/0947 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 19, 2010
From: HAUPT, ANDREAS; POHLKI, FRAUKE; DRESCHER, KARLA; WICKE, KARSTEN; UNGER, LILIANE; RELO, ANA-LUCIA; BESPALOV, ANTON; VOGG, BARBARA; BACKFISCH, GISELA; DELZER, JUERGEN
To: ABBOTT GMBH & CO. KG
Reel/Frame 024708/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2010
From: ZHANG, MIN; LAO, YANBIN
To: ABBOTT LABORATORIES
Reel/Frame 024627/0654 →