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Lipid compound and composition thereof

A compound, selected technology, applied in the direction of organic chemistry, medical preparations of non-active ingredients, capsule delivery, etc., to achieve the effect of not easy to accumulate, cheap and easy to obtain raw materials, and simple synthesis

Active Publication Date: 2021-07-30
GUANGZHOU RIBOBIO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

mRNA is a class of highly negatively charged biomolecules that must overcome the barrier of cell membranes before being translated into proteins to perform biological functions. Therefore, the efficient delivery of such biomolecules in vivo is an important challenge

Method used

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  • Lipid compound and composition thereof
  • Lipid compound and composition thereof
  • Lipid compound and composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Embodiment 1 - the synthesis of A1

[0112]

[0113] Hexadecane bromide (2.22g, 7.28mmol) was dissolved in 50ml of absolute ethanol, DIEA (1.17g, 9.10mmol) and aminoalcohol compound (2g, 6.07mmol) were added, reacted at 80°C for 18h, after the reaction was complete , concentrated to remove solvent, diluted with 200ml of EA, washed once with 200ml of water, extracted and separated, dried the organic phase, concentrated to dryness, separated and purified by silica gel column (DCM: MeOH=3%--5%), and obtained 1.2g of oily product . MS(ES): m / z(M+H) + 553.54. 1 HNMR (CDCl3) δ: ppm: 4.06(t, 2H), 3.57(t, 2H), 2.62(bs, 2H), 2.50(br, 4H), 2.29(m, 2H), 1.68- 1.25(m, 52H ), 0.88 (m, 6H).

[0114] The subsequent synthesis ideas of A5-A7, A9-A13, and A15-A32 can be designed with reference to this example, basically as follows: through brominated compounds or ketoene compounds and primary / secondary amine compounds (such as alcohol amine compounds) A substitution reaction occu...

Embodiment 2

[0115] Embodiment 2 - the synthesis of A5

[0116]

[0117] Referring to the method of Example 1, A5 was prepared to obtain 0.75 g of an oily product. MS(ES): m / z(M+H) + 835.80. 1 HNMR (CDCl 3 )δ: ppm: 4.87(m, 2H), 3.79(t, 2H), 2.67(br, 2H), 2.45(br, 4H), 2.27(t, 4H), 1.70-1.25(m, 78H), 0.90 (m, 12H).

Embodiment 3

[0118] Embodiment 3 - the synthesis of A6

[0119]

[0120] Referring to the method of Example 1, A6 was prepared to obtain 0.51 g of an oily product. MS(ES): m / z(M+H) + 611.55. 1 HNMR (CDCl 3 )δ: ppm: 4.05(t, 4H), 3.78(m, 2H), 2.65(t, 2H), 2.43(br, 4H), 2.29(m, 4H), 1.69-1.31(m, 50H), 0.90 (m, 6H).

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PUM

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Abstract

The invention relates to a lipid compound and a composition thereof, a lipid nanoparticle containing the composition, a preparation method of the composition and application of the composition in drug delivery.

Description

technical field [0001] The invention belongs to the fields of biomedicine and biotechnology, and relates to a therapeutic drug delivery system of a lipid compound. Background technique [0002] It is difficult for exogenous biomolecules and some drug molecules to penetrate the cell membrane and reach the cytoplasm to achieve therapeutic effects. mRNA is a class of highly negatively charged biomolecules that must overcome the barrier of cell membranes before being translated into proteins to perform biological functions. Therefore, the efficient delivery of such biomolecules in therapeutic applications in vivo is an important challenge. [0003] Lipid nanoparticle (LNP) is a new type of nucleic acid biomolecule delivery technology. LNP is usually composed of four components: (1) ionizable lipid, which can self-assemble with mRNA into virus-sized particles, and can transfer mRNA from Endosomes are released into the cytoplasm; (2) PEGylated lipids, which increase LNP half-life...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/12C07C229/16C07D249/04C07D401/06C07D295/088C07C237/10A61K9/51A61K47/24A61K47/28A61K47/22A61K47/18
CPCC07C229/12C07C229/16C07D249/04C07D401/06C07D295/088C07C237/10A61K9/5146A61K9/5123C07C2601/04
Inventor 张必良赵浩廷温剑
Owner GUANGZHOU RIBOBIO
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