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Water-soluble amino acid ester derivative of propofol and application thereof

A technology of amino acid esters and derivatives of propofol, which can be used in drug combination, cyanide reaction preparation, organic compound preparation, etc., and can solve problems such as unfavorable drug safety

Inactive Publication Date: 2012-03-28
CHENGDU YIPING MEDICAL SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, fospropofol will release a molecule of formaldehyde during metabolism in the body (Europ.J Pharm.Sci.2008, 31:110-117), so it is relatively unfavorable in terms of drug safety

Method used

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  • Water-soluble amino acid ester derivative of propofol and application thereof
  • Water-soluble amino acid ester derivative of propofol and application thereof
  • Water-soluble amino acid ester derivative of propofol and application thereof

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment approach

[0062] The present invention can be further described by the following examples, however, the scope of the present invention is not limited to the following examples.

[0063] Those skilled in the art can understand that various changes and modifications can be made in the present invention without departing from the spirit and scope of the present invention. The present invention provides general and / or specific descriptions of the materials and test methods used in the tests. While many of the materials and methods of manipulation which are employed for the purposes of the invention are well known in the art, the invention has been described here in as much detail as possible.

[0064] The protected amino acids and condensation reagents used in the examples are products of Shanghai Jier Biochemical Company; conventional solvents and reagents are commercial products.

Embodiment 1

[0066] Synthesis of 2-L-lysine-1,3-diisopropyl-phenyl ester dihydrochloride (compound 1)

[0067]

[0068] Compound 1

[0069] Under water bath conditions, N α -tert-butoxycarbonyl-N ε -tert-butoxycarbonyl-lysine (2.2mmol, 0.76g), N, N'-dicyclohexylcarbodiimide (4.4mmol, 0.91g), 4-dimethylaminopyridine (0.22mmol, 0.03g ), stirred and dissolved with anhydrous dichloromethane (30ml). Then propofol (2.6mmol, 0.46g) was added and stirred overnight at room temperature. The reaction was monitored by HPLC until the raw material was completely reacted. The insoluble solid was removed by filtration, and the filtrate was evaporated to dryness; ether was added to the residue, and insoluble impurities in the solution were removed by filtration. The filtrate was concentrated and quickly passed through the column with diethyl ether as the developing solvent to collect product fractions. Concentrate under reduced pressure to obtain the product. The obtained product was directly a...

Embodiment 2

[0073] Synthesis of 2-L-arginine-1,3-diisopropyl-phenyl ester dihydrochloride (compound 2)

[0074]

[0075] Compound 2

[0076] Synthetic method with reference to embodiment 1, with N α - tert-butoxycarbonyl-arginine hydrochloride replaces N α -tert-butoxycarbonyl-N ε - tert-butoxycarbonyl-lysine. Compound 2 was obtained with a yield of 62.1%.

[0077] ESI-MS m / z: 335 (M+1 + ).

[0078] 1 H NMR (D 2 O)δ0.98(d,12H,-C H 3 ), 1.6-1.7 (m, 2H, CH 2 -C H 2 -CH 2 - δ NH-), 1.8-2.0 (m, 1H, C H ), 2.2-2.2 (m, 1H, C H ), 2.99(t, 2H, C H 2 -CH 2 -CH 2 - δ NH-), 3.2-3.3 (m, 2H, CH 2 -C H 2 - δ NH-), 4.41 (dd, 1H, C H - α NH 2 ), 7.1-7.3 (m, 3H, Ar H ).

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Abstract

The invention relates to a water-soluble amino acid ester derivative of propofol and application thereof. Amino acid ester of the propofol has a structure with a formula (I), wherein R is shown in the description. The invention also relates a preparation method for a compound with the formula (I), a medicinal salt thereof, a compound-containing medicinal composition and application of the compound serving as narcotic medicines.

Description

technical field [0001] The invention relates to amino acid ester water-soluble derivatives of propofol and their non-toxic pharmaceutically acceptable salts, their preparation methods, their pharmaceutical compositions and their use as anesthetics. Background technique [0002] Propofol (chemical name: 2,6-diisopropylphenol, also known as propofol), is a quick-acting, short-acting systemic intravenous anesthetic, with the characteristics of fast onset and quick recovery, and no accumulation , has been widely used clinically. However, due to its poor water solubility, it is mainly used clinically in fat emulsion. The emulsion of propofol has poor physical stability, and it is easy to cause pain at the injection site and inflammatory reaction during clinical use, and it is difficult to be compatible with other preparations. [0003] [0004] Propofol Chemical Structure [0005] In December 2008, the U.S. FDA approved a water-soluble derivative of propofol—fospropofol sod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/20C07C229/26C07C229/08C07C279/14C07C277/08A61K31/223A61P25/20A61P23/00
Inventor 梁远军李思成
Owner CHENGDU YIPING MEDICAL SCI & TECH
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