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5-(heterocyclyl)alkyl-N-(arylsulfonyl)indole compounds and their use as 5-HT6 ligands

A technology of compound, alkyl, applied in the field of 5-alkyl-N-indole compound

Inactive Publication Date: 2009-10-07
SUVEN LIFE SCI LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some 5-HT has been disclosed 6 regulator, but is still required for regulation of 5-HT 6 compound of

Method used

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  • 5-(heterocyclyl)alkyl-N-(arylsulfonyl)indole compounds and their use as 5-HT6 ligands
  • 5-(heterocyclyl)alkyl-N-(arylsulfonyl)indole compounds and their use as 5-HT6 ligands
  • 5-(heterocyclyl)alkyl-N-(arylsulfonyl)indole compounds and their use as 5-HT6 ligands

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0140] Example 1: Preparation of 5-(4-methylpiperazin-1-ylmethyl)-1H-indole

[0141] Step (i): Preparation of (3-methyl-4-nitrophenyl)-(4-methylpiperazin-1-yl)methanone

[0142] 3-Methyl-4-nitrobenzoic acid (5.525 mmol, 1.0 g) was placed in a 25 mL two necked round bottom flask connected to a condenser (with protective tube). Thionyl chloride (6.07 mmol, 0.735 g) and 1,2-dichloroethane (5 mL) were added thereto, and the resulting solution was refluxed for 3 hours. The reaction mixture was added to another 100 mL flask containing a solution of N-methylpiperazine (16.57 mmol, 1.66 g) in 10 mL of 1,2-dichloroethane, where the temperature was maintained below 5°C. The reaction mixture was then stirred at 25°C for 0.5 hours. After the reaction was complete, the reaction mixture was poured into 50 mL of water. The 1,2-dichloroethane layer was separated, washed with water (2×10 mL), brine (10 mL), and dried over anhydrous sodium sulfate. The volatiles were removed under reduced p...

Embodiment 2

[0149] Example 2: Preparation of 1-benzenesulfonyl-5-(4-methylpiperazin-1-ylmethyl)-1H-indole dihydrochloride

[0150] 5-(4-Methylpiperazin-1-ylmethyl)-1H-indole (0.8733 mmol, 0.2 g) (obtained in Example 1) was dissolved in 2 mL of N,N-dimethylformamide. The above solution was then added slowly to a 25 mL flask containing a suspension of sodium hydride (1.31 mmol, 31.4 mg) in 1 mL DMF under nitrogen atmosphere while maintaining the temperature below 10 °C. The reaction mixture was then stirred at 25°C for 1 hour. Benzenesulfonyl chloride (1.31 mmol, 0.2312 g) was slowly added to the well stirred solution while maintaining the temperature below 10°C. The reaction mixture was stirred for an additional 2 hours. After the reaction was completed, the reaction mixture was poured onto 20 g of ice-water mixture with stirring, and the resulting mixture was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate extracts were then washed with water (20 mL), brine (20 mL), ...

Embodiment 3

[0155] The following compounds (2-34) were prepared using the procedure described in Example 2 with some non-critical modifications.

[0156] 2.

[0157] 5.

[0158] 10.

[0159] 14.

[0160] -(4-Methylpiperazin-1-ylmethyl)

[0161] -1H-Indole dihydrochloride

[0162] (2H, m).

[0163] Acyl]-5-(piperazin-1-ylmethyl)

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Abstract

The present invention relates to novel 5-(Heterocyclyl)alkyl-N- (arylsulfonyl)indole compounds of the formula (I), their derivatives, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, their derivatives, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. These compounds are useful in the treatment of various disorders that are related to 5-HT6 receptor functions. Specifically, the compounds of this invention are also useful in the treatment of various CNS disorders, hematological disorders, eating disorders, diseases associated with pain, respiratory diseases, genito-urological disorders, cardiovascular diseases and cancer.

Description

technical field [0001] The present invention relates to novel 5-(heterocyclyl)alkyl-N-(arylsulfonyl)indole compounds of formula (I), derivatives thereof, stereoisomers thereof, pharmaceutically acceptable salts thereof and A pharmaceutically acceptable composition containing said substance. [0002] [0003] The present invention also relates to methods for preparing the above-mentioned novel compounds, their derivatives, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. [0004] These compounds are useful in the treatment of 5-HT 6 Various diseases related to receptor function. In particular, the compounds of the present invention are also useful in the treatment of a variety of CNS disorders, blood disorders, eating disorders, pain-related disorders, respiratory disorders, genitourinary disorders, cardiovascular disorders, and cancer. Background technique [0005] Various central nervous system ...

Claims

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Application Information

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IPC IPC(8): C07D209/08A61K31/404A61P25/00
CPCC07D209/08C07D209/36A61P1/00A61P25/00A61P25/14A61P25/18A61P25/24A61P25/28A61P25/32A61P25/34A61P3/04C07D401/06A61K31/404
Inventor 尼罗吉·文卡塔·萨蒂亚·罗摩克里希纳拉马·萨斯特里·坎布汉帕蒂贾格迪什巴布·孔达普拉巴卡尔·科思米尔卡尔文卡特斯瓦卢·贾斯蒂
Owner SUVEN LIFE SCI LTD
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