Compound, preparation method thereof and purpose of compound in preparing drug

A compound and hydrate technology, which is applied in the field of medicine, can solve the problem of undeveloped drugs for influenza, and achieve the effects of being suitable for a wide range of use, improving medication compliance, and being convenient to use.

Active Publication Date: 2017-07-07
WWHS BIOTECH INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, current drugs to treat influenza remain to be developed

Method used

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  • Compound, preparation method thereof and purpose of compound in preparing drug
  • Compound, preparation method thereof and purpose of compound in preparing drug
  • Compound, preparation method thereof and purpose of compound in preparing drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] The compound represented by formula (I-1) was synthesized according to the following route.

[0108]

[0109]

Embodiment 2

[0111] The single crystal diffraction results of compound 9 obtained in Example 1 confirmed the correctness of the structure of compound (I-1): the ethylene glycol component was successfully connected to the -OH position of the five-membered ring skeleton ( figure 1 ). The NMR data of compound 9 are: 1 H NMR (CDCl 3 ,500MHz): δ=7.72-7.70(d,J=10.3Hz,1H),4.67-4.66(d,J=9.2Hz,1H),4.33-4.30(t,J=9.3Hz,1H),4.17- 4.10(m,1H),3.56-3.51(m,5H),3.40-3.36(m,1H),3.19-3.14(m,1H),2.19-2.14(m,1H),2.10-2.07(m,1H ),1.99(s,3H),1.82-1.78(m,1H),1.41(s,9H),1.35-1.28(m,3H),1.18-1.10(m,3H),0.85(s,9H), 0.83-0.77(m,6H),0.01(s,6H); 13 C NMR (CDCl 3 ,125MHz): δ=170.3,156.2,85.9,80.1,77.6,77.2,76.7,73.6,71.3,65.1,51.6,50.6,47.7,45.2,42.9,33.5,28.4,25.9,23.6,22.2,21.6,18.3, 11.4, 10.8, -5.4, -5.5; HRMS (ESI) Calcd.forC 27 h 55 N 2 o 6 Si + [M + h + ] 531.3824, found 531.3822.

[0112] The final target molecular prodrug (compound (I-1)) was confirmed by NMR and HRMS ( Figure 2~4 ). Its NMR da...

Embodiment 3

[0115] MDCK cells were seeded on 12-well tissue culture plates (1.2 × 10 5 cells / well, DMEM containing 10% FBS), and incubated for 48 hours at 37°C in a humidified 5% carbon dioxide incubator. Cells were infected with virus (100 PFU, Udorn-4) for 1 hour in the incubator. After adsorption of virus, the virus suspension was removed and the cells were washed with DMEM. The infected cell monolayer was flattened in DMED solid medium (containing 1% agar, 1‰TCPK-trypsin and 1% antibiotics), and the medium contained 2-fold serially diluted compound (I-1), a total of 6 gradients with 2 wells per concentration. 48 hours after infection, monolayer cells were fixed and stained with 0.5% crystal violet solution to count the number of virus-induced plaques.

[0116] The result is as Figure 5 As shown, the compound (I-1) has strong anti-influenza virus activity, and its in vitro anti-influenza virus activity EC50 is about 1nM.

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Abstract

The invention provides a compound, a preparation method thereof and a purpose of the compound in preparing a drug. The compound is a compound shown in a formula (I) or a stereoisomer, a geometric isomer, a tautomer, a nitrogen oxide, a hydrate, a solvate, a metabolite or a pharmaceutically acceptable salt of the compound shown in the formula (I). The compound provided by the invention can transform peramivir in an injection dosage form into an inhalant dosage form, improves the medication compliance of the peramivir and enables the peramivir to have the characteristics of convenience in use and suitability for use in a wide range; and in addition, the drug directly acts on a respiratory tract and a lung infected with an influenza virus after being inhaled, so that single administration is hopefully realized, and the drug can effectively have double actions of prevention and treatment to the influenza. A chemical formula is described in the description.

Description

technical field [0001] The present invention relates to the field of medicine. In particular, the present invention relates to compounds, processes for their preparation and their use in the preparation of medicaments. Background technique [0002] Influenza is an acute respiratory infectious disease caused by influenza virus. It has the characteristics of continuous outbreak and high infectivity, and can seriously endanger human health and life. From the beginning of the last century to the present, humans have experienced six influenza outbreaks, such as the 1918 H1N1 virus pandemic, which killed about 40 million people worldwide, the Hong Kong H3N2 influenza virus in 1968 and the Hong Kong H5N1 influenza virus in 1997 Both caused widespread panic. In the past ten years, the highly lethal H5N1 influenza virus broke out in 2003-2005, the H1N1 influenza virus epidemic in 2009 had a wide impact, and the H7N9 epidemic with a relatively high fatality rate appeared in my count...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C277/08C07C279/16A61K31/23A61P31/16
CPCC07C279/16
Inventor 王国新廖滔唐梅杰
Owner WWHS BIOTECH INC
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