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Compound for treating respiratory syncytial virus infection and its preparation method and application

A technology of syncytial virus and virus infection, applied in the field of biomedicine, can solve the problems of side effects of patients

Active Publication Date: 2017-10-10
SHANGHAI MEDUSA BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These properties may cause severe side effects in treated patients

Method used

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  • Compound for treating respiratory syncytial virus infection and its preparation method and application
  • Compound for treating respiratory syncytial virus infection and its preparation method and application
  • Compound for treating respiratory syncytial virus infection and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Preparation of a cyclopamine (CPM) analogue S1-2, see appendix figure 1 , attached figure 2 And attached image 3 , the preparation process is as follows:

[0084] 1) Preparation of intermediates. First, cyclopamine (498.06mg, 1.21mmol / L, 1.00eq) and triethylamine (489.76mg, 4.84mmol / L, 4.00eq) were dissolved in dry dichloromethane DCM (4mL); Trifluoroacetic anhydride (762.41 mg, 3.63 mmol, 3.00 eq) dissolved in DCM (1 mL) was added to the solution at °C; third, the reaction mixture was slowly heated to 15 °C and kept stirring for 16 h; fourth, the solution was passed through the liquid Phase chromatography-mass spectrometry (LCMS) showed that the starting material was completely consumed, the target product RT=0.996min, 25%, the by-product pertrifluoroacetic acid RT=1.125min, 47%; the fifth, the reaction mixture was concentrated, the residue Diluted with methanol (15 mL); sixth, the resulting suspension was heated to 70 °C and incubated for 1 hour; seventh, the re...

Embodiment 2

[0135] Preparation of a cyclopamine (CPM) analog S1-4, see appendix figure 1 , attached figure 2 And attached image 3 , the preparation process is as follows:

[0136] 1) Preparation of intermediates. The preparation process is the same as in Example 1.

[0137] 2) Preparation of compound S1-4. The preparation process is the same as in Example 1.

[0138] 3) To test the inhibitory effect of S1-4 on RSV replication. The test process is the same as in Example 1. See attached Figure 4 , it can be seen that the maximum inhibitory ratio of compound S1-4 to the replication ability of respiratory syncytial virus (RSV) is 88%.

[0139] 4) Test the inhibitory effect of S1-4 on the Hn signaling pathway. The test process is the same as in Example 1. See attached Figure 5 , it can be seen that the inhibitory effect of cyclopamine (CPM) analog S1-4 on gene expression is not significant, and the inhibition rate is only 5%. These data suggest that the anti-respiratory syncyti...

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Abstract

The invention discloses a compound for treating respiratory syncytial virus infection, a preparation method and application thereof. The compound is a chemical analogue of cyclopamine, which has the property of inhibiting the replication of respiratory syncytial virus, but does not have the property of inhibiting Hedgehog signaling pathway. The preparation method synthesizes the chemical analogs of the cyclopamine through pharmaceutical chemistry, and screens the analogs through two parallel in vitro tests. The compound can be used to treat respiratory virus infection, paramyxovirus infection, respiratory syncytial virus infection, bronchiolitis caused by respiratory syncytial virus, pneumonia caused by respiratory syncytial virus, otitis media caused by respiratory syncytial virus, It does not have the toxic and side effects of causing fetal malformation, overcomes the teratogenic properties of cyclopamine, and fills in the blank of drugs for treating respiratory syncytial virus infection, especially pediatric drugs.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a compound for treating respiratory syncytial virus infection and its preparation method and application. Background technique [0002] Bronchiolitis is a serious lower respiratory infectious disease mainly caused by viruses of the Paramyxoviridae family. Human respiratory syncytial virus (Human respiratory syncytial virus, hRSV) is the main cause of disease in children under 2 years old, the elderly, immunocompromised and transplant patients. To date, there are no vaccines or approved effective drugs to prevent or treat hRSV infection. The immunological drug Palivizumab is approved for use in high-risk patients, which includes only premature infants and infants with primary disease. The broad-spectrum antiviral drug ribavirin, a small molecule, can be used to treat infections, but has considerable side effects and limited efficacy. Over the past decade, several drug candi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J69/00A61K31/58A61P31/12A61P31/14A61P11/00A61P27/16
CPCC07J69/00C07J71/0005A61K31/4355A61P31/14A61K31/58
Inventor R·艾德铭曹晶晶
Owner SHANGHAI MEDUSA BIOTECHNOLOGY CO LTD
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