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

A cationic lipid and nucleic acid delivery technology, applied in the field of cationic lipid compounds and compositions, and cationic lipid compounds, can solve the problems of short circulating time of naked mRNA, easy to be degraded, difficult to enter target cells, etc., and achieve less residue in the body , Improve the clearance rate in the body, and the effect of low carrier toxicity

Active Publication Date: 2022-05-24
SHENZHEN RHEGEN BIOTECHNOLOGY CO LTD
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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

[0061] Example 1 Synthesis of Compound 1

[0062]

[0063]

[0064]

[0065] step 1:

[0066] To a solution of 2-hexyldecanoic acid (1-1, 2.00 g) in DCM (20 mL) was added 4-dimethylaminopyridine (DMAP, 95 mg) followed by 6-bromohexanol (1.68 g). After the mixture was stirred at 25°C for 5 minutes, 1-ethyl-(3-dimethylaminopropyl) (EDCl, 1.45 g) was added and the reaction mixture was stirred at 25°C for 12 hours, then TLC showed complete disappearance of the starting alcohol. The reaction mixture was diluted with DCM (30 mL) and washed with saturated NaHCO 3 (100 mL) and brine (100 mL). The organic layers were combined with Na 2 SO 4 Drying and removal of the solvent in vacuo gave the crude product, which was purified by column chromatography (silica gel column, eluent 0-1% EA (v / v) in n-hexane) and the pure fractions were evaporated, Compound 1-2 was obtained (2.00 g, 58% yield).

[0067] Step 2:

[0068] To a solution of compound 1-2 (2.00 g) in ethanol (20 mL) w...

Embodiment 2

[0077] Example 2 Synthesis of Compound 2

[0078]

[0079]

[0080]

[0081] step 1:

[0082] To a solution of 2-hexyldecanoic acid (1-1, 2.00 g) in DCM (20 mL) was added 4-dimethylaminopyridine (DMAP, 95 mg) followed by 6-bromohexanol (1.68 g). After the mixture was stirred at 25°C for 5 minutes, 1-ethyl-(3-dimethylaminopropyl) (EDCl, 1.45 g) was added and the reaction mixture was stirred at 25°C for 12 hours, then TLC showed complete disappearance of the starting alcohol. The reaction mixture was diluted with DCM (30 mL) and washed with saturated NaHCO 3 (100 mL) and brine (100 mL). The organic layers were combined with Na 2 SO 4 Drying and removal of the solvent in vacuo gave the crude product, which was purified by column chromatography (silica gel column, eluent 0-1% EA (v / v) in n-hexane) and the pure fractions were evaporated, Compound 1-2 was obtained (2.01 g, 56% yield).

[0083] Step 2:

[0084] To a solution of compound 1-2 (2.01 g) in ethanol (20 mL)...

Embodiment 3

[0093] Example 3 Synthesis of Compound 3

[0094]

[0095]

[0096]

[0097] step 1:

[0098] To a solution of compound 3-1 (2.00 g) in DCM (20 mL) were sequentially added 4-dimethylaminopyridine (DMAP, 84 mg) and 7-bromoheptanol (2.05 g). After the mixture was stirred at 25°C for 5 minutes, 1-ethyl-(3-dimethylaminopropyl) (EDCl, 1.29 g) was added and the reaction mixture was stirred at 25°C for 12 hours, then TLC showed complete disappearance of the starting alcohol. The reaction mixture was diluted with DCM (30 mL) and washed with saturated NaHCO 3 (100 mL) and brine (100 mL). The organic layers were combined with Na2 SO 4 Drying and removal of the solvent in vacuo gave the crude product, which was purified by column chromatography (silica gel column, eluent 0-1% EA (v / v) in n-hexane) and the pure fractions were evaporated, Compound 3-2 was obtained (2.06 g, 59% yield).

[0099] Step 2:

[0100] To a solution of compound 3-2 (2.06 g) in ethanol (20 mL) was add...

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Abstract

The present invention provides cationic lipid compounds and compositions and uses for delivering nucleic acids. The compound is represented by the following formula (I). The present invention also provides the use of the nano-lipid particles with the compound as a key component in nucleic acid delivery, including delivery carrier components, preparation methods and use methods. (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 it 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C327/30A61K31/713A61K31/7088A61P31/14A61P11/00A61K47/20A61K9/127A61K39/215A61K39/155A61K39/395A61K39/00
CPCC07C327/30A61K31/713A61K31/7088A61P31/14A61P11/00A61K47/20A61K9/127A61K39/12A61K39/395A61K39/0011A61K2039/53C12N2770/20034C12N2760/18534C07K16/1027C07K2317/24A61K2039/505A61K9/5123A61K9/1271A61K2039/55555A61K2039/575A61K31/7105
Inventor 胡勇李亚霏
Owner SHENZHEN RHEGEN BIOTECHNOLOGY CO LTD
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