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Arylamide compound based on benzene ring supramolecular interaction, self-assembly morphology, and use

A compound, the technology of dimethylanilinium, is applied in the directions of non-active ingredients medical preparations, medical preparations containing active ingredients, organic chemistry, etc., and can solve problems such as unfavorable clinical use

Pending Publication Date: 2021-09-14
易天奇 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds are inevitably brought about by the structure of the surfactant, which is significantly higher than the local neuropathological toxicity and systemic toxicity of the marketed local anesthetics, which is not conducive to further clinical use.

Method used

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  • Arylamide compound based on benzene ring supramolecular interaction, self-assembly morphology, and use
  • Arylamide compound based on benzene ring supramolecular interaction, self-assembly morphology, and use
  • Arylamide compound based on benzene ring supramolecular interaction, self-assembly morphology, and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058]

[0059] In a 100mL round bottom flask, add 5mmol of sodium hydroxycarboxylate, 5mmol of pyridine, and 30mL of anhydrous acetonitrile, and stir for 0.5h under an ice bath. Slowly add 5mmol of the corresponding organic acid chloride solution in 25mL of anhydrous acetonitrile dropwise, and the drop is completed in 15min. After filtration, 10 mL of 1N ethanol solution of hydrogen chloride was added to the filtrate, and concentrated to dryness under reduced pressure. Dichloromethane-methanol silica gel column chromatography, concentration, vacuum drying, to obtain the corresponding carboxylic acid, as follows:

[0060]

Embodiment 2

[0062]

[0063] method one:

[0064] In a 100 mL round bottom flask, add 5 mmol of sodium hydroxycarboxylate and 30 mL of 1,2-dichloroethane. 2 mmol of trimeric phosgene was added under stirring at room temperature. Pyridine 5mmol was slowly added dropwise, and stirred at room temperature for 1h. Add 5mmol of the corresponding fatty alcohol or fatty amine dropwise, and stir at 50°C for 16h. Cool to room temperature and filter. Add 10 mL of 1N ethanol solution of hydrogen chloride to the filtrate, and concentrate to dryness. Dichloromethane-methanol silica gel column chromatography, concentration, vacuum drying, to obtain the corresponding carboxylic acid, as follows:

[0065]

[0066] Method Two:

[0067] In a 100 mL round bottom flask, add 5 mmol of sodium hydroxycarboxylate and 30 mL of 1,2-dichloroethane. Add 10 mL of 1,2-dichloroethane with 5 mmol of thionyl chloride dropwise under stirring in an ice bath, and drop it in 15 minutes. Remove the ice bath and sti...

Embodiment 3

[0070]

[0071] In a 50mL round bottom flask, add 10mmol of hydroxycarboxylic acid acetamide and 10mmol of fatty alcohol, add 10mL of 70% sulfuric acid with stirring at room temperature, stir and heat at 80°C for 4h. After cooling to room temperature, the residue was poured into a beaker filled with about 100 mL of ice-water mixture, and extracted with 50 mL x 4 dichloromethane. The organic phases were combined, washed with 20 mL x 2 water, dried over anhydrous sodium sulfate, and concentrated. Add 4mmol / L sodium hydroxide aqueous solution to the residue, and stir at reflux for 6h. The residue was acidified with 1N hydrochloric acid to pH=5.0, extracted with 50 mL x 4 dichloromethane, and concentrated. Dichloromethane-methanol silica gel column chromatography, concentrated, vacuum-dried to obtain the corresponding carboxylic acid as follows:

[0072]

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PUM

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Abstract

An arylamide compound based on a benzene ring supramolecular action, a self-assembly morphology, and use. The compound has a structure as shown in formulas (I) and (II), can self-assemble in an aqueous solvent to form spherical micelles and Janus particles having a strong intermolecular pi-pi stacking effect, and can achieve a local anesthetic effect for a long time in an organism, the local anesthetic and / or analgesic effect can last for more than 48 hours, and local neuropathological toxicity and systemic toxicity are significantly lower than a disclosed long-acting local anesthetic molecule. The compound has a good prospect in use as a biological material that can self-assemble in water to form micelles and has a local anesthetic effect, and as a formulation adjuvant for packaging a biological material comprising a pharmacologically active molecule for treating symptoms such as pain and itching and / or a drug carrier, a delivery system, etc.

Description

technical field [0001] The invention relates to an arylamide compound with long-acting anesthetic effect and low toxicity, a preparation method, self-assembly form and application. Background technique [0002] Technical bottleneck in the development of long-acting local anesthetics [0003] Local anesthetics (local anesthetics, local anesthetics) are a class of drugs that can reversibly block the generation and transmission of sensory nerve impulses in the local area of ​​the drug while keeping the patient or animal awake, causing pain loss in local tissues. [0004] The action of local anesthetics is generally localized at the site of administration and rapidly loses effect as the drug diffuses from the site of administration. At present, all clinical local anesthetics can only achieve strong local anesthesia and analgesia for no more than 4 hours, which cannot meet the needs of pain after dental root canal treatment, joint bone pain, herpes zoster pain, postoperative wou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/14C07C69/24C07C69/96C07C271/12C07C59/125C07C69/40C07C233/05C07C237/04C07C255/25C07C301/00C08G83/00A61K9/14A61K9/107A61K47/18A61P29/00A61P17/04A61P23/02
CPCC07C69/14C07C69/24C07C69/96C07C271/12C07C59/125C07C69/40C07C233/05C07C237/04C07C255/25C07C301/00C08G83/008A61K9/14A61K9/1075A61K9/0019A61K47/186A61K47/18A61P29/00A61P23/02A61P17/04A61K31/167A61P25/02A61P25/04
Inventor 易天奇艾春霞
Owner 易天奇
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