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Cationic lipid compound, composition containing same and application

A technology of cationic lipids and compounds, applied in medical preparations containing active ingredients, liposome delivery, and medical preparations with non-active ingredients, etc., can solve problems such as high sensitivity and low cell permeability, and achieve rich Kind of effect

Active Publication Date: 2021-06-25
SUZHOU ABOGEN BIOSCIENCES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, nucleic acid therapeutics still face several challenges, including low cell permeability and high susceptibility to degradation of certain nucleic acid molecules, including RNA

Method used

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  • Cationic lipid compound, composition containing same and application
  • Cationic lipid compound, composition containing same and application
  • Cationic lipid compound, composition containing same and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] The synthetic route of compound 1:

[0084]

[0085]

[0086] Step 1: Synthesis of compound 1-1

[0087] To 2-hexyldecanol (2.0 g, 8.26 mmol, 1.0 eq) and 6-bromohexanoic acid (1.92 g, 10.0 mmol, 1.2 eq) in dichloromethane (30 mL) was added diisopropylethylamine ( 266.9mg, 2.08mmol, 0.25eq) and DMAP (201.8mg, 1.67mmol, 0.2eq). After the mixture was stirred at room temperature for 5 minutes, EDCI (2.85 g, 14.87 mmol, 1.8 eq) was added and the reaction mixture was stirred at room temperature overnight, then TLC showed complete disappearance of the starting alcohol. The reaction mixture was diluted with DCM (300 mL) and washed with saturated NaHCO 3 (100mL), water (100mL) and brine (100mL) for washing. The combined organic layers were washed with Na 2 SO 4 Drying and removal of the solvent in vacuo afforded the crude product, which was purified by column chromatography (silica gel column, eluent 0-1% EA (volume percent) in n-hexane) and the pure product fractions...

Embodiment 2

[0096] The synthetic route of compound 2:

[0097]

[0098]

[0099] Step 1: Synthesis of compound 2-2

[0100] A mixture of 1,2-epoxytetradecane (500 mg, 2.36 mmol, 1.0 eq) and compound 2-1 (411.1 mg, 3.54 mmol, 1.5 eq) in EtOH (10 mL) was stirred overnight at room temperature. The mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (gradient elution, DCM:MeOH=1:0~10:1, volume ratio) to obtain compound 2-2 (720 mg, 92.7%) as a yellow oil. LCMS: Rt: 0.74 min; MS m / z (ESI): 329.3[M+H] + .

[0101] Step 2: Synthesis of compound 2

[0102] Contains compound 2-1 (300 mg, 0.91 mmol, 1.0eq), compound 1-1 (460.1 mg, 1.10 mmol, 1.2eq), K 2 CO 3 (377.5 mg, 2.73 mmol, 2.7 eq), Cs 2 CO 3 (80.05 mg, 0.245 mmol, 0.27eq) and a catalytic amount of NaI (36.7 mg, 0.245 mmol, 0.27eq) in acetonitrile (4 mL) were stirred at 80°C overnight. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was purifie...

Embodiment 3

[0106] Synthetic route of compound 3

[0107]

[0108]

[0109] Step 1: Synthesis of Compound 3-2

[0110] A mixture of 1,2-epoxytetradecane (353 mg, 1.67 mmol, 1.0 eq) and compound 3-1 (300 mg, 2.08 mmol, 1.24 eq) in EtOH (10 mL) was stirred overnight at room temperature. The mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (gradient elution, DCM:MeOH=1:0~10:1, volume ratio) to obtain compound 3-2 (500 mg, 84.0%) as a yellow oil. LCMS: Rt: 0.730 min; MS m / z (ESI): 357.4[M+H] + .

[0111] Step 2: Synthesis of Compound 3

[0112] Contains compound 3-2 (500 mg, 1.4 mmol, 1.0eq), compound 1-1 (704.1 mg, 1.69 mmol, 1.2eq), K 2 CO 3 (483 mg, 3.5 mmol, 2.5 eq), Cs 2 CO 3 (136.8 mg, 0.42 mmol, 0.3 eq) and a catalytic amount of NaI (62.9 mg, 0.42 mmol, 0.3 eq) in acetonitrile (5 mL) were stirred at 80 °C overnight. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by PREP-...

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Abstract

The invention provides a cationic lipid compound, a composition containing the cationic lipid compound and application. In order to provide more choices for delivery of preparations such as nucleic acid drugs, gene vaccines, small molecule drugs and the like, the invention provides a cationic lipid compound shown in the general formula or pharmaceutically available salts thereof. The cationic lipid compound provided by the invention can be used for delivering DNA, RNA or small molecule drugs, enriches the types of cationic lipid compounds, and has important significance for the development and application of nucleic acid preventive and therapeutic agents.

Description

technical field [0001] The present invention specifically relates to a cationic lipid compound, its composition and application. Background technique [0002] Therapeutic nucleic acids have the potential to revolutionize vaccination, gene therapy, protein replacement therapy, and other genetic disease treatments. Since the first clinical studies of therapeutic nucleic acids began in the 2000s, research into the design of nucleic acid molecules and their delivery methods has made significant progress. However, nucleic acid therapeutics still face several challenges, including low cell permeability and high susceptibility to degradation of certain nucleic acid molecules, including RNA. Therefore, it is necessary to develop more lipid compounds capable of delivering therapeutic or preventive agents, especially for the delivery of nucleic acid therapeutic agents, and related methods and compositions, so as to facilitate the extracellular or intracellular delivery of various the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/18A61K47/54A61K47/60A61K9/127A61K39/00A61K45/00B82Y5/00C07C229/16C07C229/22C07C237/10C07D295/13
CPCA61K9/127A61K39/00A61K45/00A61K47/18A61K47/543A61K47/60B82Y5/00C07C229/16C07C229/22C07C237/10C07D295/13
Inventor 英博王秀莲
Owner SUZHOU ABOGEN BIOSCIENCES CO LTD
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