IP Library Granted Patent US 7,838,518
Granted Patent B2
US 7,838,518 · App. 10/504,556 · Granted Nov 23, 2010

1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders

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Quick Facts
Patent No.
US 7,838,518
App. No.
10/504,556
Granted
Nov 23, 2010
Kind
B2
Abstract

The present invention relates to 1-arylsulfonyl-3 substituted indole or indoline derivatives having the general formula (I) (I) wherein the dotted line represents an optional bond; n is 0 or 1; m is 0-5 and Ar, R6-R11 are defined in the description. The invention further relates to pharmaceutical compositions comprising said derivatives, and to the use of these 1-arylsulfonyl-3-substituted indole or indoline derivatives in the treatment of central nervous disorders such as psychosis, schizophrenia, manic depressions, depressions, neurological disorders, cognitive enhancement, Parkinson's disease, amyotrophic lateral sclerosis, Alzheimer's disease and Huntington's disease.

Claims (20)

1. A 1-arylsulfonyl-3-substituted indole or indoline compound having the general formula I

wherein

Ar is selected from phenyl, biphenyl, naphthyl, thienyl, furyl, benzothienyl, benzothiadiazolyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzodioxinyl, quinolinyl, and isoquinolinyl, Ar being optionally substituted with 1-5 substitutents selected from halogen, (C 1-4 )alkyl (optionally substituted with halogen), (C 1-4 )alkyloxy (optionally substituted with halogen), (C 6-12 )aryl (optionally substituted with halogen or (C 1-4 )alkyloxy), (C 6-12 )aryloxy (optionally substituted with halogen), di(C 1-4 )alkylamino, (C 1-4 )alkanoyl or (C 1-4 )alkanoylamino;

the dotted line represents an optional bond;

n is 0 or 1;

m is 2-3;

R 6 represents 1-4 substituents independently selected from H, (C 1-4 )alkyl (optionally substituted with halogen), (C 1-4 )alkyloxy (optionally substituted with halogen), (C 1-4 )alkyloxycarbonyl, cyano, nitro and halogen;

R 7 together with R 9 complete a 7-membered saturated ring;

each R 8 is independently H, (C 1-4 ) alkyl or (C 6-12 )aryl (optionally substituted with halogen, (C 1-4 )alkyl or (C 1-4 )alkyloxy);

and

R 10 is H, (C 1-4 )alkyl, (C 6-12 )aryl or (C 6-12 )aryl(C 1-4 )alkyl;

each R 11 is independently H or (C 1-4 )alkyl; or

a pharmaceutically acceptable salt thereof.

2. The 1-arylsulfonyl-3-substituted indole or indoline compound of claim 1 , wherein the Ar is selected from phenyl, naphthyl, thienyl and benzothienyl.

3. The 1-arylsulfonyl-3-substituted indole or indoline derivative of claim 1 , wherein m is 2, all of R 8 and R 11 are H, R 10 is H or (C 1-4 )alkyl.

4. The 1-arylsulfonyl-3-substituted indole or indoline compound of claim 1 , wherein n is 0.

5. A pharmaceutical composition, comprising:

the 1-arylsulfonyl-3-substituted indole or indoline compound of formula I or a pharmaceutically acceptable salt thereof, as according to claim 1 and

a pharmaceutically acceptable carrier therefore.

6. A method of treating a disorder selected from psychosis, schizophrenia, manic depressions, depressions, neurological disorders, cognitive enhancement, Parkinson's disease, amyotrophic lateral sclerosis, Alzheimer's disease or Huntington's disease, in a patient in need thereof comprising administering to the patient an effective amount of a 1-arylsulfonyl-3-substituted indole or indoline compound of claim 1 .

Assignments (6)
MERGER Recorded Mar 8, 2013
From: ORGANON BIOSCIENCES NEDERLAND B.V.
To: MERCK SHARP & DOHME B.V.
Reel/Frame 029940/0296 →
MERGER Recorded Mar 7, 2013
From: MSD OSS B.V.
To: ORGANON BIOSCIENCES NEDERLAND B.V.
Reel/Frame 029939/0001 →
MERGER Recorded Dec 1, 2011
From: N.V. ORGANON
To: MSD OSS B.V.
Reel/Frame 027307/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 30, 2007
From: AKZO NOBEL N.V.
To: N.V. ORGANON
Reel/Frame 018816/0737 →
CORRECTIVE ASSIGNMENT TO CORRECT THE SEVENTH ASSIGNOR'S NAME AND THE ASSIGNEE'S ADDRESS PREVIOUSLY RECORDED ON REEL 016394 FRAME 0325. ASSIGNOR(S) HEREBY CONFIRMS THE 7TH ASSIGNOR'S NAME "DAVID ROBERT JAAP" AND THE ASSIGNEE'S ADDRESS IS "VELPERWEG 76, 6824 BM ARNHEM, NETHERLANDS.". Recorded Feb 23, 2006
From: SPINKS, DANIEL; ARMER, RICHARD E.; MILLER, DAVID J.; RANKOVIC, ZORAN; SPINKS, GAYLE; MESTRES, JORDI; JAAP, DAVID ROBERT
To: AKZO NOBEL N.V.
Reel/Frame 017204/0406 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2004
From: SPINKS, DANIEL; ARMER, RICHARD E.; MILLER, DAVID J.; RANKOVIC, ZORAN; SPINKS, GAYLE; MESTRES, JORDI; JAAP, DAVID R.
To: AKZO NOBEL N.V.
Reel/Frame 016394/0325 →