Immune agonist and composition, applications of immune agonist and composition, and preparation method of composition

A technology of agonist and composition, which is applied in the field of hepatitis B vaccine prevention and treatment, can solve the problem that hepatitis B vaccine cannot prevent and eliminate chronic infection of hepatitis B virus at the same time, and achieves enhanced immune cytokine induction, strong immune activation effect, and significant innovation and practical effects

Pending Publication Date: 2017-10-24
SHENZHEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The object of the present invention is to provide immune stimulant and composition and its application and composition preparation method, which solves the problem that the hepatitis B vaccine in the prior art cannot simultaneously prevent and clear the chronic infection of hepatitis B virus

Method used

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  • Immune agonist and composition, applications of immune agonist and composition, and preparation method of composition
  • Immune agonist and composition, applications of immune agonist and composition, and preparation method of composition
  • Immune agonist and composition, applications of immune agonist and composition, and preparation method of composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the synthesis of the immunostimulant (SZU-103) represented by structural formula I

[0055] Such as figure 1 As indicated, weigh 344mg (1mmol) SZU-008T and 341mg (1.125mmol) diuretic acid and dissolve in 8mL DMF, add HBTU (427mg, 1.125mmol), triethylamine (416μL, 3mmol) and catalytic amount of DMAP, room temperature The reaction was stirred overnight. The reaction solution was poured into 100 mL of water, filtered with suction, and the filter residue was washed with water and dried to obtain a crude product. After separation by column chromatography (DCM:MeOH=20:1), 475 mg of white solid was obtained with a yield of 75.5%. Such as figure 2 Shown, ESI-MS: m / z=629.1[M+H] + .

Embodiment 2

[0056] Embodiment 2: the synthesis of the immunostimulant (SZU-117) represented by structural formula II

[0057] Such as image 3 As shown, in anhydrous DMF solution of SZU-101 (1 g, 0.002 mol), add EDCI (0.0025 mol), HOBT (0.0025 mol) and stir at room temperature for half an hour. DIEA (0.004mol) was added dropwise at 0°C, followed by N-Boc-piperazine (0.0025mol), and reacted overnight at room temperature. The reaction was monitored by TLC until the end of the reaction, and the reaction solution was poured into water, filtered with suction, washed with water and dried, then added with a 1:4 TFA / DCM mixed solvent and stirred overnight. After the reaction was completed, the solvent was removed under reduced pressure, redissolved with a small amount of ethanol, and 2N hydrochloric acid was added to form a salt. After spin-drying, diethyl ether was added to triturate and filtered to obtain SZU-130 with a yield of 56%.

[0058] SZU-130 (100 mg), acryloyl chloride and triethyla...

Embodiment 3

[0059] Embodiment 3: the synthesis of the immunostimulant (SZU-114) represented by structural formula III

[0060] Such as Figure 5 As indicated, SZU-008T (350 mg), EDCI (172 mg), and HOBT (172 mg) were dissolved in anhydrous DMF, and DIEA (0.35 mL) was added dropwise at 0°C. After the dripping was completed, the reaction was continued at room temperature for 30 minutes, and 117 mg of trans-4-dimethylaminocroton hydrochloride was added, and the reaction was carried out overnight at room temperature. LCMS monitoring, after the reaction was completed, the reaction solution was poured into water, filtered with suction, and the filter residue was washed with water and dried to obtain the crude product. After preparative liquid phase separation, 130 mg of white solid was obtained with a yield of 33%. Such as Figure 6 Shown, ESI-MS: m / z=456.2[M+H] + .

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Abstract

The invention relates to an immune agonist and a composition, applications of the immune agonist and the composition, and a preparation method of the composition. The immune agonist and the composition keep hepatitis B virus specific antibodies of original prophylactic vaccines in animal bodies and human bodies, can inactivate and clear cells infected with hepatitis B viruses, and have double effects of prevention and treatment; and the immune agonist and the composition have stronger immune activation effects than the original HBsAg (Hepatitis B surface antigen), show reinforced immune cell factor induction, higher antibody generating effect and especially high-level mark Th1 type immune generation of gamma-interferon and IgG2a antibodies, and have remarkable innovation and practicability for clearing hepatitis B viruses.

Description

technical field [0001] The invention relates to the technical field of hepatitis B vaccine prevention and treatment, and more specifically, to an immune stimulant, a composition, an application thereof, and a preparation method of the composition. Background technique [0002] Hepatitis B vaccine is a medicine used to prevent hepatitis B. After vaccination, the immune system can be stimulated to produce protective antibodies, so that the human body has the immunity to prevent hepatitis B and achieve the purpose of preventing hepatitis B infection. However, there are 90 million people infected with hepatitis B virus (HBV) in my country, of which 20 million are chronic hepatitis B patients. For chronic hepatitis B infection patients and patients, preventive hepatitis B vaccine is basically ineffective. Therefore, there is a great need for a "therapeutic hepatitis B vaccine" that can both prevent and eliminate the chronic infection of hepatitis B virus. Contents of the inve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K39/39A61K39/29A61K39/385A61P1/16A61P31/20A61P37/02C07D473/18A61K31/52
Inventor 靳广毅王竹林胡云龙唐黎刘冰
Owner SHENZHEN UNIV
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