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Triterpene-polypeptide conjugate, drug composition and uses thereof

A technology of compounds and medicinal salts, applied in the direction of fusion of polypeptides, peptides, peptide sources, etc., can solve problems such as low resistance, weak activity, and easy drug resistance

Inactive Publication Date: 2015-09-02
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, T20 itself has some defects and deficiencies
The first is the problem of drug resistance: since T20 is completely derived from the natural HR2 sequence, it has low resistance to target mutations and is prone to drug resistance
In addition, many saponin compounds have broad-spectrum antiviral activity, but the activity is weak

Method used

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  • Triterpene-polypeptide conjugate, drug composition and uses thereof
  • Triterpene-polypeptide conjugate, drug composition and uses thereof
  • Triterpene-polypeptide conjugate, drug composition and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0180] Embodiment 1: the preparation of compound 1

[0181] 1.1 Synthesis of small molecule compound BAc

[0182]

[0183] Synthesis of Intermediate 2:

[0184] Under nitrogen protection, 0.3 g (0.66 mmol) of compound 1, 0.11 g of imidazole and 8 mg of DMAP were dissolved in 2 ml of DMF. TBDPSCl 0.23 mL (0.79 mmol) was added. Stir at reflux overnight. After the reaction was completed, 25 mL of DCM was added, and the organic phase was washed with 1N hydrochloric acid and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Separation and purification by column chromatography gave a white solid with a yield of 72%.

[0185] Synthesis of intermediate 3:

[0186] 0.25 g of Intermediate 2 and 40 mg of DMAP were dissolved in 10 mL of DCM, and 0.11 g of pentynoic acid was added. Add 0.23g DIC under stirring, and continue stirring at room temperature until the reaction is complete. Add 25mL of DCM to dilute, wash with 10% citric acid, saturated sodium...

Embodiment 2－6

[0202] Embodiment 2-6: Preparation of Compound 2-3, 43-45

[0203] The method is the same as in Example 1, except that the BAc conjugated to the N-terminal of the polypeptide is replaced by UAc or OAc, or the N-terminal of the polypeptide is introduced into Ile to obtain compounds 2-3, 43-45.

Embodiment 7

[0204] Embodiment 7: the preparation of compound 4

[0205] 7.1 Synthesis of Small Molecule Compound BAO

[0206]

[0207] Weigh 0.5 g of compound 1 and dissolve it in 10 mL of DMF, add 0.46 g of potassium carbonate and 171 μl of propyne bromide. Stir at room temperature for 4 hours, and monitor the reaction by TLC. After the reaction was completed, the filtrate was filtered to remove salt and the filtrate was evaporated to dryness, followed by separation and purification by column chromatography to obtain a white solid with a yield of 65%.

[0208] 7.2 Preparation of BAc-peptide conjugate (compound 4): The synthesis process was the same as that of compound 1, except that the small molecule at the N-terminal of the peptide chain was replaced with BAo.

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PUM

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Abstract

Provided is a triterpene-polypeptide conjugate, stereoisomer or pharmaceutically acceptable salt thereof. Also provided are a pharmaceutical composition containing the conjugate, stereoisomer or pharmaceutically acceptable salt thereof, and use of the conjugate, stereoisomer or pharmaceutically acceptable salt thereof in treating or preventing related diseases caused by HIV infection, especially the acquired immunodeficiency syndrome (AIDS).

Description

technical field [0001] The invention belongs to the field of biomedicine, and relates to a triterpene-polypeptide conjugate, its pharmaceutical composition and application. Specifically, the present invention relates to the conjugates represented by formula I, derivatives thereof, stereoisomers thereof, or pharmaceutically acceptable salts thereof. The present invention also relates to a pharmaceutical composition containing the above-mentioned conjugates of formula I, derivatives thereof, stereoisomers thereof, or pharmaceutically acceptable salts thereof, conjugates of formula I, derivatives thereof, stereoisomers thereof , or a pharmaceutically acceptable salt thereof in the treatment or prevention of related diseases caused by HIV infection, especially acquired immunodeficiency syndrome (AIDS, namely AIDS). [0002] XA 1 -L 1 –P–K(L 2 -XA 2 ) Formula I. Background technique [0003] AIDS is mainly a fatal infectious disease caused by human immunodeficiency virus ty...

Claims

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Application Information

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IPC IPC(8): C07K14/00A61K38/16A61P31/18
CPCA61K38/00A61P31/18C07K14/005C07K2319/00C12N2740/16122
Inventor 刘克良王潮娜荷芽姜喜凤许笑宇
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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