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Propofol phosphamide derivative, preparation method and medical application thereof

A pharmaceutical and pharmaceutical technology, applied in the field of propofol phosphoramide derivatives and their intermediates and preparation, can solve the problems of poor water solubility and poor stability of propofol, and achieve good oral absorption characteristics

Active Publication Date: 2021-02-23
XPISCORIC INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After this type of drug enters the body orally, it can release 2,6-diisopropylphenol derivatives at a certain hydrolysis rate according to the design requirements, producing anesthetic, sedative and hypnotic effects, thereby overcoming the poor water solubility and poor stability of propofol Shortcomings

Method used

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  • Propofol phosphamide derivative, preparation method and medical application thereof
  • Propofol phosphamide derivative, preparation method and medical application thereof
  • Propofol phosphamide derivative, preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] (S)-2-[[(R)-(2,6-Diisopropyl)phenoxy-ethoxycarbonyl-phosphoryl]amino]propanoic acid isopropyl ester (1)

[0062] (S)-isopropyl 2-[[(R)-(2,6-diisopropylphenoxy)-(ethoxycarbonyl)phosphoryl]amino]propanoate(1)

[0063]

[0064]

[0065] first step

[0066] Ethoxycarbonylphosphonic acid (1b)

[0067] Ethoxycarbonylphosphonic acid

[0068] Ethyl diethoxyphosphoroformate 1a (210.0 g, 1.0 mol) was dissolved in 800 mL of acetonitrile, trimethylbromosilane (460.0 g, 3.0 mol) was added dropwise, and reacted at 65°C for 2 hours. After the reaction, it was concentrated under reduced pressure to obtain ethoxycarbonylphosphonic acid 1b as a yellow liquid (154.0 g, 1.0 mol, yield 100%).

[0069] second step

[0070] Ethyl dichlorophosphoroformate (1c)

[0071] Ethyl dichlorophosphorylformate

[0072] Dissolve methoxycarbonylphosphonic acid 1b (154.0g, 1.0mol) in 650mL of dichloromethane, under nitrogen protection, add oxalyl chloride (510.0g, 4.0mol) dropwise at 0°C, DMF (...

Embodiment 2

[0090] (S)-2-[[(R)-(2,6-diisopropyl)phenoxy-methoxycarbonyl-phosphoryl]amino]propanoic acid isopropyl ester (2)

[0091] (S)-isopropyl 2-[[(R)-(2,6-diisopropylphenoxy)-(methoxycarbonyl)phosphoryl]amino]propanoate(2)

[0092]

[0093]

[0094] first step

[0095] Methyl diethoxyphosphoroformate (2b)

[0096] Methyldiethoxyphosphorylformate

[0097] Triethyl phosphite 2a (50.0 g, 0.3 mol) was dissolved in 250 mL of dichloromethane, methyl chloroformate (28.4 g, 0.3 mol) was added dropwise at 0°C, and slowly raised to room temperature to react overnight. After the reaction, it was concentrated under reduced pressure to obtain methyl diethoxyphosphoroformate 2b as a colorless liquid (59.0 g, 0.3 mol, yield 100%).

[0098] second step

[0099] Methoxycarbonylphosphonic acid (2c)

[0100] Methoxycarbonylphosphonic acid

[0101] Methyl diethoxyphosphoroformate 2b (59.0 g, 0.3 mol) was dissolved in 250 mL of acetonitrile, trimethylbromosilane (138.2 g, 0.9 mol) was added d...

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Abstract

The invention discloses a propofol phosphamide derivative, a preparation method and medical application thereof, and relates to a compound represented by a general formula (I), a stereoisomer or a pharmaceutically acceptable salt thereof, and applications in medicine, wherein the structure of the compound represented by the general formula (I) is represented by the following formula, and the groupdefinition is consistent with the definition in the specification.

Description

technical field [0001] The invention relates to a propofol phosphoramide derivative, its intermediate, its preparation method, and its use in the preparation of medicines. Background technique [0002] Propofol, whose chemical name is 2,6-diisopropylphenol, is an alkyl acid short-acting intravenous general anesthetic widely used clinically, and is in a leading and dominant position in the intravenous anesthetic market at home and abroad . After intravenous injection, it is quickly distributed throughout the body, and can produce a sleep state within 40 seconds, and enter anesthesia quickly and smoothly. In clinical use, compared with other anesthetic drugs, propofol has a rapid onset of effect, rapid recovery, fully controllable pharmacokinetics and pharmacodynamics, a wide range of applicable diseases, and few contraindications. It is suitable for both ordinary patients and high-risk patients. It is safe to use. [0003] The phenolic hydroxyl group of propofol is prone t...

Claims

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Application Information

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IPC IPC(8): C07F9/44A61P25/00A61P25/20A61P25/22A61P25/24A61P25/06A61P25/08A61P25/18A61P23/00A61P9/10A61P1/08A61K31/664
CPCA61P1/08A61P9/10A61P23/00A61P25/00A61P25/06A61P25/08A61P25/18A61P25/20A61P25/22A61P25/24C07B2200/07C07B2200/13C07F9/443C07F9/4449C07F9/4465
Inventor 林其先宫爱申刘建余盛首一方健赵伟
Owner XPISCORIC INC
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