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1-methylolimidazole [1, 2-alpha] quinoxaline compound and its application

A technology of hydroxymethylimidazole and quinoxaline, which is applied in the directions of drug combination, organic chemistry, medical preparations containing active ingredients, etc., can solve the problems of low incidence of side effects, limited improvement of solubility, and difficulty in finding

Inactive Publication Date: 2005-04-27
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These compounds have a low incidence of side effects
However, the solubility of such compounds is poor, and it is difficult to find a suitable solvent for dissolving and administering
[0004] It is well known that the conversion of pharmaceutical compounds into salts can improve the solubility to some extent, but for such compounds, even when converted into salts, the solubility improvement is limited

Method used

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  • 1-methylolimidazole [1, 2-alpha] quinoxaline compound and its application
  • 1-methylolimidazole [1, 2-alpha] quinoxaline compound and its application
  • 1-methylolimidazole [1, 2-alpha] quinoxaline compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0125] Example 1: N-cyclopentyl-7,8-dichloro-1-hydroxymethyl[1,2-a]quinoxalin-4-amine

[0126] 1.1. Add 29g (0.392mol) of 2,3-epoxypropanol, 61g (0.726mol) of 3,4-dihydropyran, 10g (0.04mol) of pyridinium p-toluenesulfonate and 300ml of dichloromethane 500ml round bottom flask, stirred, and heated to 30°C. TLC followed the progress of the reaction. After 60 hours of reaction, the reaction was stopped. After cooling to room temperature, 400 ml of anhydrous diethyl ether was added to the reaction mixture. Wash with half-saturated sodium chloride solution (3 x 200ml). The organic layer was separated and dried over anhydrous sodium sulfate. After filtering, the solvent was evaporated to dryness to obtain 35.2 g of light yellow oil. The yield was 56.8%. The crude product can be fed directly without purification. It can be purified by silica gel column chromatography, eluent: petroleum ether: ethyl acetate = 3:1, to obtain 19.4 g of colorless liquid. The yield was 31.3%.

...

Embodiment 2

[0139] Example 2: N-cyclopentyl-1-hydroxymethyl[1,2-a]quinoxalin-4-amine

[0140] 2.1. Add 9.3g (0.095mol) of imidazole-5-methanol, 9.5g (0.068mol) of o-fluoronitrobenzene, 10ml (0.069mol) of triethylamine and 150ml of acetonitrile into a 250ml eggplant-shaped flask. Stir and warm to reflux. TLC detects the progress of the reaction. React for 30 hours, stop the reaction, and cool to room temperature. After freezing overnight, a solid precipitated out and was filtered with suction to obtain 7.8 g of a yellow solid. The filtrate was evaporated to dryness under reduced pressure, and the residue was separated by silica gel column chromatography. Eluent: ethyl acetate: methanol = 10:1. 2.4 g of a yellow solid was obtained. A total of 10.2 g of the product was obtained with a yield of 68%.

[0141] The melting point is 150-152°C.

[0142] MS (+Q): 219.9 (M+1 peak), 202.0 (M-H 2 O peak).

[0143] 2.2. Add 1-(2-nitrophenyl)imidazole-5-methanol 4,8g (21.9mmol) and triethylamin...

Embodiment 3

[0155] Example 3: N-n-propyl-7,8-dichloro-1-hydroxymethyl[1,2-a]quinoxalin-4-amine

[0156] The compound was prepared according to the method of Example 1, except that R 1 NH 2 For n-propylamine.

[0157] Melting point: 226-228°C.

[0158] MS (+Q): 324.9 (M+1), 327.0 (M+3).

[0159] 1 H-NMR (δ): 8.52 (1H, s, ArH), 7.75 (1H, s, ArH), 7.56 (1H, s, ArH), 4.93 (2H, s, CH 2 ), 3.50 (2H, t, CH 2 ), 1.68 (2H, m, CH 2 ), 0.93 (3H, t, CH 3 )

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Abstract

The present invention relates to 1-methylol imidazole [1, 2-alpha] quinolxaline compounds and their medicinal salts. These compounds and their medicinal compositions may be used as adenosine acceptor antagonist in preventing and treating depression, dysgosia, kidney failure, asthma, acute respiratory distress, arrhythmia and other symptoms.

Description

field of invention [0001] The present invention relates to imidazo 1-hydroxymethyl imidazo [1,2-a] quinoxaline compounds, their preparation process, their pharmaceutical composition and as adenosine A 1 Use of receptor antagonists in the prevention or treatment of depression, cognitive deficits, renal failure, asthma, acute respiratory distress, arrhythmia, cardiac arrest and other diseases. Background technique [0002] Adenosine is an important neurotransmitter and / or neuromodulator, which inhibits neurotransmission by inhibiting the release of certain neurotransmitters, causing neuronal hyperpolarization to reduce neuronal excitability, and changing axonal transmission. selective adenosine A 1 Receptor antagonists have been developed to treat conditions such as depression, cognitive deficits, renal failure, cardiac arrhythmias, and cardiac arrest. Adenosine receptor antagonists can also be used in the treatment of allergic inflammatory reactions and asthma. Adenosine A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4985A61P9/00A61P9/06A61P11/00A61P13/12A61P25/24C07D487/04
Inventor 恽榴红刘春河李伟章李锦苏瑞斌王勃刘英
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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