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Application of a kind of ethylbenzamide compound in preparation of local anesthetic

A technology of ethylbenzamide and local anesthetics, which is applied in the field of application of ethylbenzamide compounds in the preparation of local anesthetics, and can solve the problems that local anesthetics have not yet been developed

Active Publication Date: 2021-07-30
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no relatively ideal local anesthetic has been developed

Method used

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  • Application of a kind of ethylbenzamide compound in preparation of local anesthetic
  • Application of a kind of ethylbenzamide compound in preparation of local anesthetic
  • Application of a kind of ethylbenzamide compound in preparation of local anesthetic

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0047] The preparation method of compound A1-21

[0048] React substituted benzoyl chloride with 2-bromoethylamine to obtain intermediate A; react piperazine with benzoyl chloride to obtain intermediate C; react intermediate A with intermediate C to obtain the target compound; the reaction formula is as follows:

[0049]

[0050] Synthesis of Intermediate A: Put 0.1mol 2-bromoethylamine in a round-bottomed flask, add 0.2mol triethylamine, then slowly add 0.1mol substituted benzoyl chloride dropwise in an ice bath, react at room temperature overnight, and white crystals precipitate out. Suction filtration, drying, toluene recrystallization, that is.

[0051] Synthesis of intermediate C: phenylalkanoic acid and thionyl chloride were heated under reflux in a round-bottomed flask for 5 hours, excess thionyl chloride was evaporated, and distillation under reduced pressure was carried out to obtain phenylalkanoyl chloride; piperazine hexahydrate and Stir the glacial acetic acid ...

Embodiment 1

[0055] Synthesis of Compound A1: Intermediate A was synthesized using 3-fluorobenzoyl chloride, and Intermediate C was synthesized using phenylacetyl chloride. The yield was 83%, and mp: 176-178°C.

[0056] 1H NMR (300 MHz, CDCl 3 ), δ: 8.84 (s, 1H, -NH-), 7.81 (m, 2H, Ph-H), 6.98 (m, 2H, Ph-H), 3.60 (m, 2H, -CH 2 -), 2.65(m, 4H, -CH 2 -), 2.50(m, 2H, -CH 2 -), 4.54(m, 6H, -CH 2 -), 8.02(m, 3H, Ph-H), 6.73 (m, 2H, Ph-H), 1.07(s, 1H, -NH-); HR-ESI-MS m / z: calcd forC 21 h 24 N 3 o 2 F{[M+H] +} 369.2.

Embodiment 2

[0058] Synthesis of Compound A5: Intermediate A was synthesized using 2-methoxybenzoyl chloride, and Intermediate C was synthesized using phenylacetyl chloride. The yield was 82%, and mp: 167-168°C.

[0059] 1H NMR (300 MHz, CDCl 3 ), δ: 8.84 (s, 1H, -NH-), 7.81 (m, 2H, Ph-H), 6.98 (m, 2H, Ph-H), 3.60 (m, 2H, -CH2 -), 2.65(m, 4H, -CH 2 -), 2.50(m, 2H, -CH 2 -), 4.54(m, 6H, -CH 2 -), 3.81(s, 3H, -CH 3 ), 8.02(m, 3H, Ph-H), 6.73 (m, 2H, Ph-H), 1.07(s, 1H, -NH-); HR-ESI-MS m / z: calcd for C 22 h 27 N 3 o 3 {[M+H] +} 381.3.

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Abstract

The invention provides an application of ethyl benzamide compounds in the preparation of local anesthetics. The compound has the characteristics of less toxic and side effects, short onset time and long action time.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the application of an ethylbenzamide compound in the preparation of local anesthetics. Background technique [0002] Local anesthetic (local anesthesia) drugs are a class of drugs that can reversibly block the generation and transmission of sensory nerve impulses locally, and cause temporary and reversible loss of sensation in the innervated parts under conscious conditions. . Generally, the effect of local anesthetics is limited to the site of administration and disappears rapidly as the drug diffuses from the site of administration. Compared with general anesthesia, local anesthesia can greatly reduce the impact on the patient's physiological function, so local anesthesia is widely used in local infiltration anesthesia, nerve block anesthesia, epidural anesthesia, etc. [0003] With the widespread clinical application of local anesthetics, their toxic and side effects have b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/495A61P23/02C07D295/182
CPCA61K31/495A61P23/02C07D295/182
Inventor 阳慧宋磊
Owner WEST CHINA HOSPITAL SICHUAN UNIV