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Compound and applications of compound in preparation of anti-hepatitis C virus drugs

A compound and reaction technology, applied in the application field of preparing anti-hepatitis C virus drugs, can solve problems such as drug failure, high price, and inability to benefit patients

Active Publication Date: 2017-07-14
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, Gilead's sofosbuvir is considered to be a blockbuster drug in the field of HCV, but its high price (the cost of cure is as high as hundreds of thousands of RMB) makes it unable to benefit all patients; on the other hand, the virus is prone to mutation and drug resistance , making existing drugs ineffective

Method used

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  • Compound and applications of compound in preparation of anti-hepatitis C virus drugs
  • Compound and applications of compound in preparation of anti-hepatitis C virus drugs
  • Compound and applications of compound in preparation of anti-hepatitis C virus drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] Embodiment 1, the preparation of compound 1

[0124]

[0125] Get intermediate A1 in 100ml round bottom flask, add 198mg Pd(dppf) 2 .DCM, 2g potassium phosphate and 1.2g p-trifluoromethylthiophenylboronic acid pinacol ester, add 10ml toluene, under the protection of argon, react at 100°C for 12h, spin the solvent, add 100ml water, extract with 20ml dichloromethane Twice, using petroleum ether: ethyl acetate = 30:1 to pass through a silica gel column to obtain 1 g of intermediate A3 (colorless liquid), with a yield of 64%.

[0126] Take 1g of intermediate A3 and 650mg of intermediate A4 in a 25ml round bottom flask, add 240mg of p-toluenesulfonic acid monohydrate and 10ml of n-butanol, react at 130°C for 16h, spin the solvent under reduced pressure, add water, and use 20ml of ethyl acetate Extracted twice, and passed through a silica gel column with ethyl acetate:petroleum ether=1:1 to obtain 320 mg of compound 1 (white solid), with a total yield of 24%.

[0127] Th...

Embodiment 2

[0129] Embodiment 2, the preparation of compound 2

[0130]

[0131] Referring to Example 1 where A1 was replaced by A5, other conditions and subsequent steps were the same to obtain compound 2.

[0132] The characterization data of compound 2 are as follows:

[0133] H-NMR (400MHz, d 6 -DMSO, ppm): 0.93(t, J=6.96Hz, 3H), 2.26(q, J=7.12Hz, 2H), 4.14(s, 1H), 6.91(dd, J=8.12Hz, J=11.28Hz ,1H),7.34(d,J=8.32Hz,1H),7.45–7.54(m,7H),7.67(d,J=7.68Hz,2H),11.52(s,1H).LC-MS: calcd for C 25 h 20 f 4 NOS[M+H] + :458.11, found 458.21.

Embodiment 3

[0134] Embodiment 3, the preparation of compound 3

[0135]

[0136] Take 600mg of intermediate A1 in a 100ml round bottom flask, add 420mg of potassium carbonate and 600mg of p-trifluoromethylthiophenol, add 10ml of N,N-methylformamide DMF, and react at 60°C for 3h under the protection of argon, add 100ml of water was extracted twice with 20ml of dichloromethane and passed through a silica gel column with petroleum ether: ethyl acetate = 20:1 to obtain 918mg of intermediate A6 (colorless liquid) with a yield of 90%.

[0137] Referring to the steps and conditions in Example 1, A3 was replaced by A6, and other conditions were the same to obtain compound 3.

[0138] The characterization data of compound 3 are as follows:

[0139] 1 H-NMR (400MHz, d 6 -DMSO,ppm):11.62(s,1H),7.66(m,4H),7.58(d,J=7.96Hz,2H),7.52(m,1H),7.39(d,J=8.40Hz,1H) ,7.20(d,J=8.56Hz,2H),6.94(dd,J=11.88Hz,J=7.96Hz,1H),5.30(s,2H),1.4(s,3H).LC-MS: calcd for C 24 h 18 f 4 NO 2 S[M+H] + :460.09, found 4...

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Abstract

The present invention discloses a compound and applications of the compound in preparation of anti-hepatitis C virus drugs, wherein the structure formula of the compound is represented by a formula I or II, and the compound represented by the formula I or compound represented by the formula II can be subjected to drug combination with other anti-virus drugs such as interferon (PEG IFN-[alpha]), ribavirin (RBV), boceprevir, telaprevir, simeprevir, sofosbuvir, daclatasvir and the like t prepare anti-HCV products and other anti-virus infection products. According to the present invention, the compound has rich functional group diversity and modificability, and the product is relatively easy to separate and purify; the compounds can well inhibit HCV and other viruses, are obtained through phenotype screening, have different antiviral mechanisms, have extremely novel and innovated structures in the anti-virus field, and are not reported in the prior art; and the compound of the present invention has broad development and application prospect.

Description

technical field [0001] The invention relates to a compound and its application in preparing anti-hepatitis C virus medicine. Background technique [0002] Hepatitis C is caused by hepatitis C virus (HCV) infection and is mainly transmitted by blood / body fluids, including unclean needles, syringes and drug use. The World Health Organization estimates that 170 million people are infected with HCV worldwide. The anti-HCV positive rate of healthy people in my country is 0.7% to 3.1%, about 38 million people. Due to various factors such as the biological characteristics of the virus and the immune function of the host, it is often difficult for the body’s immunity to effectively clear the virus, resulting in 80% of infected patients eventually developing chronic hepatitis C, and 60% of chronic patients eventually developing liver cirrhosis and can only wait for the liver Another 15% to 20% of infected people recover naturally without treatment; from the perspective of the patie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/233C07D401/04A61K31/47A61K31/5377A61K31/4709A61P31/14
CPCC07D215/233C07D401/04
Inventor 饶燏娄智勇杨毅庆曹林彭宗根蒋建东
Owner TSINGHUA UNIV
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