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Cationic lipid compounds and compositions and uses for delivery of nucleic acids

A technology for cationic lipids and nucleic acid delivery, applied in drug combination, liposome delivery, organic chemistry, etc., can solve the problems of difficulty in entering target cells, short circulation time of naked mRNA, easy to be degraded, etc., to improve the clearance rate in vivo , The effect of less residue in the body and low carrier toxicity

Active Publication Date: 2022-07-22
SHENZHEN RHEGEN BIOTECHNOLOGY CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003]However, naked mRNA circulates in the body for a short time, is easily degraded, and is difficult to enter target cells or tissues

Method used

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  • Cationic lipid compounds and compositions and uses for delivery of nucleic acids
  • Cationic lipid compounds and compositions and uses for delivery of nucleic acids
  • Cationic lipid compounds and compositions and uses for delivery of nucleic acids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Synthesis of Compound 2

[0078]

[0079] step 1:

[0080]To a solution of compound 2-1 (3.00 g) in tert-butanol (20 mL) were added 1-decanol (3.23 g) and cesium carbonate (11.1 g) in this order. After the solution was stirred at room temperature for 4 hours, a spot plate (petroleum ether:ethyl acetate=10:1) showed the formation of new spots. The reaction solution was filtered, and the concentrated crude product of the obtained filtrate was purified by column chromatography (silica gel column, eluent was a petroleum ether solution containing 0-10% ethyl acetate (volume percentage)) to obtain compound 2-2 (3.93 g , 69% yield).

[0081] Step 2:

[0082] To a solution of compound 2-2 (3.00 g) in THF (20 mL) and water was added lithium hydroxide (860 mg), and the mixture was stirred at 60° C. for 16 hours. TLC showed the formation of dots with increasing polarity. The reaction mixture was concentrated to remove tetrahydrofuran, diluted with water, extracted once wit...

Embodiment 2

[0093] Synthesis of Compound 3

[0094]

[0095]

[0096] step 1:

[0097] To a solution of compound 3-1 (3.00 g) in tert-butanol (20 mL) were added 1-decanol (4.45 g) and cesium carbonate (15.3 g) in this order. After the mixture was stirred at room temperature for 4 hours, a spot plate (petroleum ether:ethyl acetate=10:1) showed the formation of new spots. The reaction solution was filtered to obtain the crude product after the filtrate was concentrated, and the crude product was purified by column chromatography (silica gel column, eluent was a petroleum ether solution containing 0-10% ethyl acetate (volume percentage)) to obtain compound 3- 2 (3.1 g, 46% yield).

[0098] Step 2:

[0099] To a solution of compound 3-2 (3.00 g) in THF (20 mL) and water was added lithium hydroxide (860 mg), and the mixture was stirred at 60° C. for 16 hours. TLC (petroleum ether:ethyl acetate=10:1) showed the generation of a point with increased polarity. The reaction mixture was c...

Embodiment 3

[0106] Synthesis of compound 4

[0107]

[0108]

[0109] step 1:

[0110] To a solution of compound 4-1 (3.00 g) in tert-butanol (20 mL) were added 1-decanol (4.6 g) and cesium carbonate (16.1 g) in this order. After the mixture was stirred at room temperature for 4 hours, a spot plate (petroleum ether:ethyl acetate=10:1) showed the formation of new spots. The reaction solution was filtered to obtain a crude product after the filtrate was concentrated. The crude product was purified by column chromatography (silica gel column, eluent was a petroleum ether solution containing 0-10% ethyl acetate (volume percentage)) to obtain compound 4- 2 (3.0 g, 47.3% yield).

[0111] Step 2:

[0112]To a solution of compound 4-2 (3.00 g) in THF (20 mL) and water was added lithium hydroxide (860 mg), and the mixture was stirred at 60° C. for 16 hours. TLC (petroleum ether:ethyl acetate=10:1) showed the generation of a point with increased polarity. The reaction mixture was concent...

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Abstract

The present invention provides cationic lipid compounds and compositions and uses for delivering nucleic acids. The compound is shown as a formula (I). The invention also provides application of nano-lipid particles taking the compound as a key component in the aspect of nucleic acid delivery, a component containing a delivery carrier, a preparation method and a use method. (I).

Description

technical field [0001] The present invention relates to the field of lipid delivery carrier, which is a class of cationic lipid compounds, which can form drug-carrying nano-lipid particles after combining with other lipid components, so as to realize the delivery of nucleic acid from extracellular to intracellular in vitro and in vivo. In particular, the present invention relates to cationic lipid compounds and compositions and uses for the delivery of nucleic acids. Background technique [0002] Nucleic acid drugs replace, compensate, block or modify specific genes by introducing foreign genes into target cells or tissues to achieve the purpose of treating and preventing diseases. Its R&D and production process is relatively simple, and has the advantages of short R&D cycle, high clinical development success rate, and better improvement plasticity. Nucleic acid vaccines, as one of the main forces for the prevention of COVID-19 in recent years, have also proved its great po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/12C07C229/16C07C219/06C07D295/13C07C323/52C07C323/12A61K31/713A61K31/7088A61P31/14A61P11/00A61K9/127A61K47/24A61K47/28A61K47/18
CPCC07C229/12C07C229/16C07C219/06C07D295/13C07C323/52C07C323/12A61K31/713A61K31/7088A61P31/14A61P11/00A61K9/127A61K47/24A61K47/28A61K47/18C07D317/28A61K47/543A61K9/0019A61K9/1272
Inventor 胡勇李亚霏胡昭宇
Owner SHENZHEN RHEGEN BIOTECHNOLOGY CO LTD
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