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3' substituted compounds having 5-ht6 receptor affinity

A technology of compounds and solvates, applied in the field of compounds with selective 5-HT6 affinity, can solve the problem of selective agonists and antagonists hindering receptor function in vivo research and other issues

Inactive Publication Date: 2010-08-11
MEMORY PHARMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although 5-HT 6 Receptors have unique pharmacological profiles, but a lack of selective agonists and antagonists hampers in vivo studies of receptor function

Method used

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  • 3' substituted compounds having 5-ht6 receptor affinity
  • 3' substituted compounds having 5-ht6 receptor affinity
  • 3' substituted compounds having 5-ht6 receptor affinity

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0452] I. Preparation of Sulfonyl Chloride

[0453] The sulfonyl chlorides used herein are commercially available from suppliers such as Sigma-Aldrich, Milwaukee, WI US; Lancaster Synthesis, Windham, NH USA; or Maybridge Chemical Co. Ltd., Cornwall, UK; or can be obtained by methods known in the art or Prepare according to the method outlined below.

[0454] For example, benzenesulfonyl chloride, 2-chlorobenzenesulfonyl chloride, 3-chlorobenzenesulfonyl chloride, 4-chlorobenzenesulfonyl chloride, 2-fluorobenzenesulfonyl chloride, 3-fluorobenzenesulfonyl chloride, 4-fluorobenzenesulfonyl chloride, 2- Methoxybenzenesulfonyl chloride, 3-methoxybenzenesulfonyl chloride, 4-methoxybenzenesulfonyl chloride, 2-difluoromethoxybenzenesulfonyl chloride, 3-difluoromethoxybenzenesulfonyl chloride, 4-di Fluoromethoxybenzenesulfonyl chloride, 2-trifluoromethoxybenzenesulfonyl chloride, 3-trifluoromethoxybenzenesulfonyl chloride, 4-trifluoromethoxybenzenesulfonyl chloride, 3-trifluoromethylb...

Embodiment 1

[0847] Example 1: Synthesis of 3-piperazin-1-yl-1-[(3-pyrrolidin-1-ylphenyl)sulfonyl]-1H-pyrrolo[3,2-b]pyridine (compound 64)

[0848]

[0849] 4-(1H-pyrrolo[3,2-b]pyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester (112 mg, 0.000369 mol) and tetrahydrofuran (3 mL, 0.03 mol) and N, N-di Methylformamide (3 mL, 0.03 mol) was added to the vial. The material was stirred at 5 °C under nitrogen atmosphere and a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.44 mL) was added. The reaction was stirred for 10 minutes and a solution of 3-pyrrolidin-1-ylbenzenesulfonyl chloride (163 mg, 0.000665 mol) in tetrahydrofuran (4 mL, 0.05 mol) was added followed by N,N-dimethylethylamine (112 uL , 0.00103mol). The reaction was stirred for 20 minutes and extracted with ethyl acetate, washed with water and brine. The solvent was concentrated in vacuo. The residue was stirred in dichloromethane (5 mL, 0.08 mol), and trifluoroacetic acid (1 mL, 0.01 mol) was ad...

Embodiment 2

[0851] Example 2: 3-{[3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[3,2-b]pyridin-1 base]sulfonyl}quinoline ( Compound 50) Synthesis

[0852]

[0853] 4-(1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester (99.0 mg, 0.000331mol) was stirred in tetrahydrofuran (3mL, 0.04mol) and N,N-dimethylformamide (3mL, 0.04mol), and a solution of 1.0M sodium bis(trimethylsilyl)amide in tetrahydrofuran was added ( 0.50mL). The reaction was stirred for 30 minutes and added to a mixture containing quinoline-3-sulfonyl chloride hydrochloride (131 mg, 0.000496 mol;) and tetrahydrofuran (3 mL, 0.04 mol) and N,N-dimethyl ethylamine (53.8 uL, 0.000496 mol) in a 1 neck round bottom flask. Gas evolution was observed during the transfer of the azaindole anion solution to the sulfonyl chloride solution (once the base was added to the suspension in THF, it became clear. The reaction was stirred for 30 minutes. The reaction was washed with acetic acid Ethyl et...

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Abstract

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein Q, R1, R4, m and Ar are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

Description

[0001] This application claims priority to US Provisional Application US 60 / 956,102, filed August 15, 2007, and US Provisional Application US 61 / 019,789, filed January 8, 2008, both of which are incorporated herein by reference in their entireties. field of invention [0002] The present invention relates to serotonin 5-HT 6 field of affinity. More specifically, the present invention relates to 5-HT 6 New compounds with affinity for receptors, especially selective for 5-HT 6 Compounds of affinity, methods of making these compounds, compositions comprising these compounds, and methods of use thereof. Background of the invention [0003] Human 5-hydroxytryptamine-6 ​​(5-HT 6 ) receptor, one of the most recently cloned serotonergic receptors, is a 440 amino acid polypeptide with seven transmembrane domains typical of G protein-coupled receptors. It is one of 14 receptors that mediate the action of the neurotransmitter serotonin (5-HT, serotonin) (Hoyer et al., Neuropharmaco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/78A61K31/425A61K31/535
CPCC07D471/04A61P1/06A61P1/12A61P1/14A61P25/00A61P25/02A61P25/04A61P25/06A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P3/04A61P43/00
Inventor R·邓恩W·谢A·郑一姆
Owner MEMORY PHARMA CORP
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