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Alkyl-substituted phenol carboxylate compound, preparation method and application
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A technology of phenol esters and compounds, applied in the field of alkyl substituted phenol carboxylate compounds, preparation and application, capable of solving problems such as drug accumulation, poor stability, and limitations
Inactive Publication Date: 2020-01-07
重庆迈迪生医药科技有限公司
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Another example is propofolsuccinic acid monoester sodium salt described in WO200213810, which is a highly water-soluble 2,6-diisopropylphenol derivative, but its poor stability in aqueous solution also limits its water solubility 2, Development and application of 6-diisopropylphenol prodrug
In addition, the biggest disadvantage of the water-soluble prodrug of propofol is slow onset of action and easy accumulation of the drug. The recovery time after the drug is significantly longer than the direct use of propofol at an effective dose, which will cause a delay in recovery after anesthesia. Increased medical monitoring costs and patient postoperative risk
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Embodiment 1
[0017]
[0018] Dissolve 1.47g of N-methyliminodiacetic acid (CAS: 4408-64-4) and 1.78g of propofol in 30mL of N,N-dimethylformamide, add 2.06g of N,N-dicyclohexyl Carbodiimide (DCC), stirred at room temperature for 2 hours, filtered, evaporated to dryness under reduced pressure of DMF, added 50mL of 2N hydrochloric acid to the residue, filtered, evaporated to dryness of the filtrate under reduced pressure, and obtained 1.92 g of white solid by column chromatography, namely Compound 1, yield: 55.2%.
[0022] Dissolve 1.34g of diglycolic acid (CAS: 110-99-6) and 1.78g of propofol in 30mL of N,N-dimethylformamide, add 2.06g of N,N-dicyclohexylcarbodiimide (DCC), stirred at room temperature for 2 hours, filtered, evaporated to dry DMF under reduced pressure, added 50mL 2N hydrochloric acid to the residue, precipitated, filtered, suspended the precipitate with 10mL water, adjusted the pH value to 8.5 with 0.5N aqueous sodium hydroxide solution, added 20mL of acetone precipitated a white solid and filtered to obtain 1.08g of compound 2 with a yield of 36.6%.
[0026] Dissolve 2.19g of 5-tert-butoxycarbonylamino-3-oxavaleric acid (CAS: 142929-49-5) and 1.78g of propofol in 30mL of N,N-dimethylformamide, add 2.06g of N , N-dicyclohexylcarbodiimide (DCC), stirred at room temperature for 2 hours, filtered, evaporated to dryness in DMF under reduced pressure, added 20mL 20% methanolic hydrochloric acid solution to the residue and stirred at room temperature for 2 hours, filtered, evaporated to dryness, and the residue was Column chromatography yielded 1.21 g of a white solid, namely compound 3, with a yield of 38.4%.
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Abstract
The invention discloses an alkyl-substituted phenolcarboxylate derivative, and a preparation method and application thereof. The structure of the derivative is shown in the specification, wherein X in a formula is O, S and NR, and R is H or C1-5 alkyl; Y is CH2, CH2CH2 or CO; Z is OH, NH2, HSO4, H2PO4, N (CH3) 2, NHCH3, N < + > (CH3) 3, H2NPO3, OCH2COOH or H2NMePO3; L is isopropyl or A pharmaceutically acceptable salt of the alkyl-substituted phenolcarboxylate derivative, such as sodium salt, amino acid salt, hydrochloride and the like. The invention also discloses a pharmaceutically acceptable solvate, such as a hydrate. The compound represented by formula (I) and the pharmaceutically acceptable salt or solvate thereof may have water solubility, are stable in aqueous solution, can rapidly release alkyl substituted phenol and non-toxic and low-toxicity metabolites with sedative-hypnotic and / or anesthetic effects under the action of enzyme after entering body, and are good in safety,so that the compound can be applied to the field of sedative-hypnotic and / or anesthetic drugs for intravenous or extravenous administration.
Description
technical field [0001] Phosphate ester compound of alkyl substituted phenol carboxylate, preparation method and use. The compound can be used as a sedativehypnotic and / or anestheticdrug administered through intravenous route or extravenous route. Background technique [0002] Propofol (Propofol) is an alkyl-substituted phenol derivative. It was developed in the 1970s and used clinically in the 1980s. It has become the most commonly used intravenous general anesthesiadrug in clinical practice. Sedation in maintenance and intensive care. Propofol has the advantages of fast onset of action, short duration of action, and quick recovery after drug withdrawal, but its solubility in water is only 146mg / L, which is an insoluble drug. In order to make propofol convenient for intravenous administration, its solubility problem must be solved. Historically, a large number of preparation methods have been used to improve the water solubility of propofol, and finally the current mai...
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