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Water-soluble triethanolamine derivative

A technology of compound and propylamine, which is applied in the fields of drug combination, anesthetic, organic chemistry, etc., can solve the problems of prolonging the time of anesthesia, and achieve the effect of avoiding injection pain and embolism, facilitating absorption, and good anesthesia and analgesia

Active Publication Date: 2012-06-27
CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the compound enters the human body, it can be hydrolyzed to release propofol quickly, prolong the time of anesthesia, and effectively overcome the disadvantage of poor water solubility of propofol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: Preparation of Propofol Chloromethyl Ether

[0024]

[0025] Under argon protection, 10.0 g of propofol was added to a stirred suspension of sodium hydride (2.2 g, 60% dispersion in mineral oil) in anhydrous dimethoxyethane, and the resulting mixture was continuously Stir for 15 minutes, then in 15 minutes, in the homogeneous solution that forms, dropwise add chloroiodomethane 12.3ml, filter after stirring for 3 hours, evaporate solvent and excess chloroiodomethane, residue uses silica gel column chromatography ( Petroleum ether: ethyl acetate = 10:1 (v:v)) to obtain 10.2 g of a white solid.

[0026] Yield: 80.1%, purity: 99%.

[0027] 1 H NMR (300 MHz, CDCl3) δ: 7.08-7.20 (m, 3H), 5.75 (s, 2H), 3.36 (m, 2H), 1.21 (d, 12H).

Embodiment 2

[0028] Embodiment 2: the preparation of three-2-(propofol O-methoxy)ethylamine

[0029]

[0030] Under the protection of nitrogen, add 2.65g sodium hydride (60%) in batches to 50ml tetrahydrofuran solution of 2.0g triethanolamine at 0°C, after stirring for 15 minutes, add dropwise 50ml of tetrahydrofuran solution of 5.0g propofol chloromethyl ether, about After 20 minutes of dripping, heat up to 20°C and stir for 3 hours, cool in an ice bath, add 2ml of water dropwise, concentrate under reduced pressure for 0.5 hours to exhaust the solvent (-90KPa, 35°C), and purify the remaining oil by silica gel column chromatography (petroleum ether : ethyl acetate=5:1 (v:v)) to obtain 7.8 g of white solid.

[0031] Yield: 82.0%, purity greater than 99%.

[0032] 1 H NMR (300MHz, DMSO-d6) δ: 7.10-7.21 (m, 9H), 5.92 (s, 6H), 3.95 (t, 6H), 3.40 (m, 6H), 2.61 (t, 6H), 1.25 ( d, 36H).

Embodiment 3

[0033] Embodiment 3: the preparation of three-2-(propofol O-methoxyl) propylamine

[0034]

[0035] According to the method of Example 2, tri-2-(propofol O-methoxy)propylamine can be prepared with propofol chloromethyl ether and triisopropanolamine under the action of sodium hydride.

[0036] 1 HNMR (300MHz, DMSO-d6) δ: 7.10-7.21 (m, 9H), 5.93 (s, 6H), 4.10 (m, 3H), 3.40 (m, 6H.), 2.52-2.76 (m, 6H), 1.26(d, 36H), 1.15(d, 9H).

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Abstract

The invention discloses a new-brand triethanolamine derivative, namely a propofol prodrug which is high in water solubility and is more suitable for clinic. After entering a human body, the compound can be quickly hydrolyzed, and propofol is released; and the narcotism time is prolonged, and the defect of low water solubility of propofol is effectively overcome.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a water-soluble derivative of propofol triolamine or a pharmaceutically acceptable salt thereof and a preparation method thereof. Background technique [0002] Propofol (2,6-diisopropylphenol, propofol, formula II), is a short intravenous general anesthetic, has the advantages of quick onset, no obvious accumulation, and quick recovery. However, due to the steric hindrance of the isopropyl group, propofol has poor water solubility and can only be administered in the form of emulsion clinically. The disadvantages of emulsions are obvious: injection causes pain, large oil droplets may cause embolism, it is difficult to add other drugs in the preparation, poor stability, etc., all of which limit the clinical use of propofol. [0003] [0004] In view of the above reasons, the inventors have designed a new class of propofol prodrugs with strong water solubility and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/08A61P23/00
Inventor 王颖闫革新李泽林
Owner CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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