Dipropofol dihydrogen pyrophosphate and salt thereof, preparation method and application thereof

A technology of propofol dihydrogen pyrophosphate and propofol pyrophosphate, which is applied in the preparation of water-soluble prodrug dipropofol dihydrogen pyrophosphate and its salt, and preparation of sedative, hypnotic and anesthetic drugs It can solve the problems of unfavorable drug safety and other problems, and achieve the effects of easy large-scale preparation, high yield and good water solubility

Inactive Publication Date: 2012-07-25
HAISCO PHARMA GRP INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two phosphoesterification modifications can improve the water solubility of propofol and improve the pharmacokinetic properties. Fospropofol Disodium (Fospropofol Disodium) will release a molecule of formaldehyde during the metabolism in vivo (European Journal of Pharmaceutical Sciences , 2008, 34:110-117), so it is unfavorable in terms of drug safety

Method used

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  • Dipropofol dihydrogen pyrophosphate and salt thereof, preparation method and application thereof
  • Dipropofol dihydrogen pyrophosphate and salt thereof, preparation method and application thereof
  • Dipropofol dihydrogen pyrophosphate and salt thereof, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1.42g (0.01mol) P 2 o 5and 10ml of anhydrous toluene were added to the reaction flask, heated to 80°C under stirring, and 1.78g (0.01mol) of propofol was added dropwise rapidly. Part of the solvent was dried, and the rest was allowed to stand for cooling. A large amount of white solids were formed. Suction filtration and washing with anhydrous toluene gave 1.86 g of white crystals of dipropofol dihydrogen pyrophosphate, with a yield of 74.69%.

Embodiment 2

[0053] 0.71g (0.005mol) P 2 o 5 and 10ml of anhydrous toluene were added to the reaction flask, and under stirring at room temperature, 1.78g (0.01mol) propofol was quickly added dropwise, and the constant temperature was continued to stir and react for 2 hours after the addition was completed. After standing for cooling, a white solid was formed, which was filtered by suction and washed with anhydrous toluene to obtain 1.17 g of white crystals of dihydrogen pyrophosphate of dipropofol, with a yield of 46.98%.

Embodiment 3

[0055] 11.36g (0.08mol) P 2 o 5 and 50ml of anhydrous toluene were added to the reaction flask, heated to 110°C under stirring, and 1.78g (0.01mol) propofol was quickly added dropwise. Part of the solvent was dried, and the remaining part was allowed to stand for cooling, and a white solid was formed, which was filtered by suction and washed with anhydrous toluene to obtain 1.62 g of white crystals of dipropofol dihydrogen pyrophosphate, with a yield of 65.06%.

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Abstract

The invention discloses dipropofol dihydrogen pyrophosphate and salt thereof, a preparation method and application thereof. Ipropofol serving as a raw material and phosphorus pentoxide undergo reaction in an anhydrous organic solvent, a reaction product is separated and purified to form the dipropofol dihydrogen pyrophosphate of formula (2), and the salt of the dipropofol dihydrogen pyrophosphateis any pharmaceutically acceptable salt. The obtained compound can be used for preparing sedative hypnotic and anaesthetic medicaments. The method of the invention has the advantages of simple and convenient operation, easily obtained raw materials, low cost and higher yield. The obtained compound has stable property and good water solubility, can be prepared into various formulations for clinical application, and overcomes many defects of single propofol administration.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a water-soluble prodrug dipropofol dihydrogen pyrophosphate and its salt, its preparation method and its application in the preparation of sedative hypnotic and anesthetic drugs. Background technique [0002] Propofol (Propofol, Formula 1) has another name called Propofol and Diprivan, and its chemical name is 2,6-diisopropylphenol, which is a widely used systemic intravenous anesthetic. It has the advantages of quick onset, short action time, quick and complete recovery, few adverse reactions, no sequelae, wide application range (can be used for anesthesia induction, maintenance and auxiliary epidural anesthesia), and easy to control dosage. However, propofol is a fat-soluble compound and hardly soluble in water, so its pharmacokinetic properties are not good. At present, the preparation form of fat emulsion is mainly used for intravenous administration. This fat e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/12A61K31/661A61P25/20A61P23/00
CPCC07F9/091C07F9/12A61P23/00A61P25/20
Inventor 邹永孙洪宜魏文刘现可肖春芬
Owner HAISCO PHARMA GRP INC
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