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A compound with analgesic effect and preparation method thereof

A technology of compounds and target compounds, applied in the field of compounds with analgesic effect and their preparation, can solve the problems of clinical reference restrictions, addiction and dependence

Inactive Publication Date: 2016-05-18
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have good analgesic activity, but can all lead to serious addiction and dependence
Therefore, these drugs are the highest-level controlled drugs in various countries, and their clinical use is restricted.

Method used

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  • A compound with analgesic effect and preparation method thereof
  • A compound with analgesic effect and preparation method thereof
  • A compound with analgesic effect and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of Example 1 Compound (I-1)

[0036]

[0037] (1) Synthesis of p-dimethylaminobenzaldehyde

[0038]In a 100mL three-necked flask, add 4.9g (0.032mol) of phosphorus oxychloride, and slowly add 2.5g (0.031mol) of DMF dropwise under ice bath. N-dimethylaniline, after dropping, move the reaction solution to a boiling water bath for 2-4 hours (monitor the end point of the reaction with thin-layer chromatography), after the reaction is completed, pour the reaction solution into 20 mL of ice water, and use 30% hydrogen The sodium oxide solution was used to adjust the pH to 4-4.5, left to stand for crystallization for 24 hours, and suction filtered to obtain a light yellow or nearly colorless solid, which was recrystallized with 30 mL of ethanol-water (1:2.5) to obtain the product p-dimethylaminobenzaldehyde.

[0039]

[0040] (2) Synthesis of 2,4-methoxyacetophenone

[0041] Into a 100mL three-necked flask equipped with a condenser, a stirrer, and a thermom...

Embodiment 2

[0049] The synthesis of embodiment 2 compound (I-2)

[0050]

[0051] Add 15mL of propionic acid and 0.7g (0.014mol) of 80% hydrazine hydrate to a 100mL three-necked flask, stir and heat for 0.5h, then add 1.09g (0.0035mol) of 4-dimethylamino-2,4-dimethoxy Chichalcone, stirred and heated to 80°C for 6-8 hours (monitor the end point of the reaction with thin-layer chromatography), after the reaction is complete, adjust the pH of the obtained solution to 7-8 with dilute sodium hydroxide solution, and then dilute the solution with 20mL×3 Methyl chloride was extracted three times, and the obtained organic phase was washed three times with 20 mL×3 water, dried over anhydrous sodium sulfate, filtered, and the solvent was removed to obtain a brown oil. The crude product was separated with a silica gel column (10 g of 200-300 mesh silica gel was loaded into a silica gel column for 1 g of sample). The eluent volume ratio is v (acetone): v (petroleum ether) = 7:3. A yellow solid wa...

Embodiment 3

[0052] The synthesis of embodiment 3 compound (I-3)

[0053]

[0054] Add 15 mL of butyric acid and 0.7 g (0.014 mol) of 80% hydrazine hydrate to a 100 mL three-necked flask, stir and heat for 0.5 h, then add 1.09 g (0.0035 mol) of 4-dimethylamino-2,4-dimethoxy Chilchalcone, stirred and heated to 80°C for 5-7 hours (monitor the end point of the reaction with thin-layer chromatography), after the reaction is complete, adjust the pH of the obtained solution to 7-8 with dilute sodium hydroxide solution, and then use 20ml×3 Methyl chloride was extracted three times, and the obtained organic phase was washed three times with 20ml×3 water, dried over anhydrous sodium sulfate, filtered, and the solvent was removed to obtain a brown oil. The crude product was separated with a silica gel column (10 g of 200-300 mesh silica gel was loaded into a silica gel column for 1 g of sample). The eluent volume ratio is v (acetone): v (petroleum ether) = 7:3. A yellow oil was obtained, which ...

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Abstract

The invention discloses a compound with an analgesic effect and a preparation method thereof. Structural formulas of the compound are shown in the following formulas I, II, III or IV in the specification, wherein R is a straight-chain alkyl group with a chemical formula of CnH2n+1, and n is equal to 1 to 7. The invention also discloses a preparation method of the compound with different structural formulas, and an application of the compound in preparing capsaicin receptor inhibitors. The compound disclosed by the invention has relatively strong analgesic activities, and part of the analgesic activities can exceed that of demerol; and moreover, by virtue of pharmacological experiments, a phenomenon that the compounds have addictive side effects cannot be discovered. The compound and pharmaceutically acceptable carriers disclosed by the invention can be prepared into medicine compositions and medicine preparations, and can be developed and prepared into analgesic medicines without addiction.

Description

technical field [0001] The invention relates to the technical fields of chemistry and medicine, in particular to a class of non-addictive compounds with analgesic effect and a preparation method thereof. Background technique [0002] Both disease and external injury can cause pain, and pain is the body's natural response to these injuries. Pain, however, can also cause discomfort, distress, depression, and severe pain can even lead to shock and death. Purposefully suppressing or eliminating pain is a major advance in modern medicine. Because of this, surgical operations can be carried out smoothly, and the pain of patients such as cancer patients can be relieved. However, the analgesics currently used clinically are mainly opioid receptor agonists, such as morphine, pethidine and the like. These drugs have good analgesic activity, but all can lead to serious addiction and dependence. Therefore, these drugs are the highest-level controlled drugs in various countries, and t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/06A61P29/00
CPCC07D231/06
Inventor 戴康梅之南方华万青
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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