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Anti-hepatitis C virus nucleoside compound and application thereof

A compound, anti-hepatitis C technology, applied in antiviral agents, medical preparations containing active ingredients, drug combinations, etc., can solve the problems of drug resistance, toxic side effects, different responses, and high recurrence rate

Inactive Publication Date: 2019-07-30
SHANGHAI TANGRUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently recognized as an effective antiviral drug for hepatitis C is interferon (IFN), but HCV-infected patients have different responses to interferon therapy, with an average response rate of less than 50%, and a high recurrence rate after drug withdrawal
However, the emergence of drug resistance and toxic side effects makes the treatment of HCV virus still need new drugs

Method used

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  • Anti-hepatitis C virus nucleoside compound and application thereof
  • Anti-hepatitis C virus nucleoside compound and application thereof
  • Anti-hepatitis C virus nucleoside compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054]

[0055] Step 1: Synthesis of intermediate 1A (2-hydroxyphenylglycine isopropyl ester)

[0056] 2-hydroxyphenylglycine 2g (0.01197mol, 1eq) was dissolved in 40mL of isopropanol, and 2eq of SOCl was added dropwise 2 (2.8g, 0.239mol) was heated and refluxed overnight. Spin the mother liquor to dryness, add 1mol / L dilute hydrochloric acid and methyl tert-butyl ether to extract twice, adjust the pH of the aqueous phase to alkaline with saturated sodium bicarbonate, extract three times with ethyl acetate, wash the ethyl acetate layer with brine, It was dried over anhydrous sodium sulfate, concentrated to obtain 1.1 g of crude product, and purified by column chromatography to obtain 500 mg of Intermediate 1A.

[0057] 1 H NMR (400MHz, CDCl 3 ) 7.211(td, J=7.2Hz, J=1.2Hz, 1H), 7.068(dd, J=7.2Hz, J=1.2Hz, 1H), 6.874(dd, J=8.0Hz, J=0.8Hz, 1H) , 6.827(td, J=7.6 Hz, J=1.2Hz, 1H), 5.072~5.134(m, 1H), 4.802(s, 1H), 1.282(d, J=6.4Hz, 3H), 1.191(d, J=6.4Hz, 3H).

[0058] St...

Embodiment 2

[0064]

[0065] The raw material isobutanol was used instead of isopropanol, and the others were the same as in Example 1 to obtain compound 2 (yield 50%).

[0066] 1 HNMR (400MHz, CDCl 3 ) 9.1-9.2(m, 1H), 7.67-7.64(m, 1H), 7.40-7.32(m, 3H), 7.20-7.16(m, 1H), 7.11-7.07(m, 1H), 6.22-6.19(m , 1H), 5.60-5.47(m, 1H), 5.42-5.32(m, 1H), 5.19-5.10(m, 1H), 4.73-4.42(m, 2H), 4.19-4.05(m, 2H), 3.96 (d, J=8.0Hz, 2H), 1.89-1.95 (m, 1H), 1.44-1.34 (dd, 3H), 0.84-0.91 (m, 6H); ES-LC / MS: m / z 528.2 (M +H).

Embodiment 3

[0068]

[0069] The raw material 2-amino-3-(2-hydroxyphenyl)propionic acid was used instead of 2-hydroxyphenylglycine, and the others were the same as in Example 1 to obtain compound 3 (yield: 70%)

[0070] ES-LC / MS: m / z 528.2 (M+H).

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Abstract

The invention discloses a compound represented by general formula (I) and a pharmaceutically acceptable salt thereof, A is O or C=CH 2 ; B is a nucleoside base; Z is a link or CHR 4 ; When W is a link or C (O), R is CH (R') C (Y) OR 5 ; when W is CHC(Y)OR 5 When, R is H; Y is O or S; R 1 is H, D or CN; R 2 For H, D, X, CN, CH=CH 2 , CCH or N 3 ; Each R 3 independently H, D, X, OH, N 3 , NR" 2 or C that is unsubstituted or substituted by 1 to 5 halogens 1‑6 Alkyl, C 2‑6 Alkenyl or C 2‑6 Alkynyl; each R a independently H, X, CN, R", NR" 2 , OR" or CO 2 R", or R on two adjacent carbon atoms a Form a 3-8 membered carbon ring with the connected carbon atom; each R" is independently D, C 1‑6 Alkyl, C 3‑8 Cycloalkyl, C 1‑6 Acyl or C 1‑6 Sulfonamide group; or two R "can form a 4-8 membered ring with the connected nitrogen atom. The compound represented by the general formula (I) of the present invention has excellent anti-hepatitis C virus effect.

Description

technical field [0001] The invention belongs to the field of antiviral compounds, and in particular relates to a class of anti-hepatitis C virus nucleoside compounds and applications thereof. Background technique [0002] A virus is a parasitic living organism in a non-cellular form composed of a nucleic acid molecule (DNA or RNA) and protein or only composed of protein. Hepatitis C virus (HCV), a single-stranded positive-sense RNA virus, is the main cause of post-transfusion and sporadic hepatitis. At present, it is recognized that interferon (IFN) is an effective drug for antiviral treatment of hepatitis C, but HCV-infected patients have different responses to interferon therapy, with an average response rate of less than 50%, and a high recurrence rate after drug withdrawal. FDA approved two NS3 / 4A serine protease inhibitors Telaprevir and Boceprevir in 2011, providing a new effective method for the treatment of hepatitis C. In 2013, the FDA approved the listing of Sofo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/11C07H19/213C07H19/23A61K31/7072A61K31/7076A61K31/7068A61K31/706A61P1/16A61P31/14
CPCA61P1/16A61P31/14C07H19/11C07H19/213C07H19/23
Inventor 张所明
Owner SHANGHAI TANGRUN PHARMA
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