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Naphthol derivative compound and application thereof in analgesia

A compound and naphthol technology, applied in the field of medicine, can solve the problems of low toxicity, high analgesic activity, good water solubility, etc., and achieve the effects of good development prospects, low toxicity, and high analgesic activity

Inactive Publication Date: 2021-04-20
武城县人民医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention innovatively synthesizes a naphthol-derived compound, which has high analgesic activity, good water solubility, and low toxicity, in order to obtain a new compound that can be used to prepare analgesic drugs, and no related structures have been seen in the prior art report

Method used

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  • Naphthol derivative compound and application thereof in analgesia
  • Naphthol derivative compound and application thereof in analgesia
  • Naphthol derivative compound and application thereof in analgesia

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, the synthesis of compound II

[0027]

[0028] In the presence of a catalytic amount of N,N-dimethylformamide (0.5ml), 6-methoxy-2-naphthoic acid (10.0g, 49.45mmol) and thionyl chloride (45mL, 62.2mmol) were dissolved in dichloro The reaction was refluxed in methane (60ml) for 4 hours. After the reaction was complete, the system was added to a well-stirred solution of dimethylamine hydrochloride (10.1g, 123.87mmol) and triethylamine (17.4mL, 125.18mmol) in dichloromethane (50ml) while keeping the temperature below 5 ℃. After the addition was complete, stirring was continued at 5-10°C for 0.5 hours. Water (100.0 mL) was added to quench the reaction and the organic layer was separated. The aqueous layer was extracted with dichloromethane (3 x 50.0 mL), and the combined organic phases were washed with water (2 x 50.0 mL). The organic layer was dried over anhydrous sodium sulfate, and the organic layer was concentrated to obtain a crude product. To the...

Embodiment 2

[0039] Embodiment 2, the synthesis of compound 1

[0040]

[0041] At room temperature, 6-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)naphthalene-2-ol (7.73g, 24.66mmol) was gradually added to sodium hydride (1.8g, 75.00 mmol) in DMF (50 mL) suspension. The reaction mixture was stirred at room temperature for 1.5 hours, then 2-chloro-N,N-diethyl-1-amine (8.23 g, 60.67 mmol) was added to the system. Stirring at 100°C for 2 hours, after the completion of the reaction as detected by TLC, the reaction mixture was concentrated under reduced pressure, and the obtained crude product was dissolved in dichloromethane (200mL), extracted with 2mol / L HCl (2×50mL), and the aqueous phase Adjust to pH = 10 with 10% NaOH solution, then extract with dichloromethane (2 x 100 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure to obtain Compound 1 as an off-white solid, 10.74 g, with a yield of 85.1%. LC-MS (ESI, pos, ...

Embodiment 3

[0042] The synthesis of embodiment 3, compound 2

[0043]

[0044] At room temperature, 6-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)naphthalene-2-ol (8.00 g, 25.5 mmol) was gradually added to sodium hydride (1.8 g, 75.00 mmol) in DMF (50 mL) suspension. The reaction mixture was stirred at room temperature for 1.5 hours, then 1-(2-chloroethyl)piperidine (8.93 g, 60.5 mmol) was added to the system. Stirring at 100°C for 2 hours, after the completion of the reaction as detected by TLC, the reaction mixture was concentrated under reduced pressure, and the obtained crude product was dissolved in dichloromethane (200mL), extracted with 2mol / L HCl (2×50mL), and the aqueous phase Adjust to pH = 10 with 10% NaOH solution, then extract with dichloromethane (2 x 100 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure to obtain Compound 2 as an off-white solid, 11.56 g, with a yield of 84.6%. LC-MS (ESI, pos, ...

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Abstract

The invention belongs to the field of medicines, and relates to a naphthol derivative compound and application thereof in analgesia. The structural formula of the naphthol derivative compound is shown as a formula I. Pharmacological research shows that the compound prepared by the invention has good analgesic activity and relatively low biotoxicity, so that the compound can be used for preparing analgesic drugs.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a naphthol derivative compound with analgesic activity and a preparation method thereof Background technique [0002] Neuropathic pain is a pain syndrome caused by primary damage or dysfunction of the nervous system, mainly manifested as hyperalgesia, allodynia and spontaneous pain. The pathogenesis of neurogenic pain is unclear, and it is one of the more serious clinical problems plaguing human beings today. Numerous clinical conditions are associated with or underlie neuropathic pain, such as diabetes mellitus, postoperative pain from amputation, lower back pain, cancer, chemical injury or toxins, other severe surgery, pressure from traumatic lesions Peripheral nerve damage, nutritional deficiencies, infections such as shingles, HIV, etc. [0003] At present, there is no specific drug for the treatment of neurogenic pain. Opioids and central nervous system depressants are commonly used ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/74C07C213/06C07C213/00C07C215/64C07C213/02C07C231/02C07C231/12C07C235/34C07D295/088A61P25/04
Inventor 王志强伏鸿博
Owner 武城县人民医院
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