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5,6-dimethylthieno(2,3-DI) pyrimidine derivatives, the preparation method thereof and the pharmaceutical composition comprising the same for anti-virus

A technology of dimethylthiophene and pyrimidine derivatives, which is applied in drug combinations, antiviral agents, digestive system, etc., and can solve the problems of ineffective therapeutic methods, no effective drugs for HCV development, and low cure rate.

Inactive Publication Date: 2008-09-17
依柯斯制药
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also, although an attempt was made to treat HCV with α-IFN, the response to α-IFN varied significantly according to the genotype of HCV, and the effect of this treatment was very insignificant
In particular, the therapeutic effect of α-IFN was least pronounced in the case of genotype 1b, which many infected people have
[0006] Since the RNA genome of HCV was first isolated by cloning in 1989, many studies on HCV have been conducted, but effective therapeutic drugs against HCV have not yet been developed
As a therapeutic agent against HCV infection, interferon combined with antiviral drug ribavirin is currently used, but it has insignificant effects because it has a low cure rate and shows side effects

Method used

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  • 5,6-dimethylthieno(2,3-DI) pyrimidine derivatives, the preparation method thereof and the pharmaceutical composition comprising the same for anti-virus
  • 5,6-dimethylthieno(2,3-DI) pyrimidine derivatives, the preparation method thereof and the pharmaceutical composition comprising the same for anti-virus
  • 5,6-dimethylthieno(2,3-DI) pyrimidine derivatives, the preparation method thereof and the pharmaceutical composition comprising the same for anti-virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: 4-[5,6-Dimethyl-4-(4-morpholin-4-yl-phenylamino)-thieno[2,3-d]pyrimidine Preparation of -2-yl]-piperazin-1-yl-pyridin-2-yl-methanone

[0039]220.20 mg (1.23 mmol) of 4-(4- Morpholino) aniline and 130.90 mg (1.23 mmol) of aniline, and then the mixture was stirred under reflux. After the reaction was complete, the reaction solvent ethanol was evaporated under reduced pressure, and the residue was crystallized from ethanol and filtered to yield 430 mg (quantitative) 2-chloro-5,6-dimethyl-thieno[2,3-d ] pyrimidin-4-yl-4-morpholin-4-yl-aniline. 220 mg (0.53 mmol) of the obtained product was dissolved in 20 ml of 1-butanol in a sealed tube, and 223 μl (1.59 mmol) of triethylamine and 45.9 mg of piperazine were added thereto, and the mixture was stirred at 120° C. . After the reaction was complete, the resulting solid was filtered and the filtrate was concentrated under reduced pressure, then crystallized from ethyl acetate to yield 30 mg (15% yield) of 5,6-di...

Embodiment 2

[0041] Example 2: 4-[5,6-Dimethyl-4-(4-morpholin-4-yl-phenylamino)-thieno[2,3-d]pyrimidine-2- Base]-piperazin-1-yl-pyridin-3-yl-methanone

[0042] The title product (45% yield) was obtained in the same manner as in Example 1 except that nicotinoyl chloride hydrochloride was used instead of picolinoyl hydrochloride.

[0043] 1 H NMR (CDCl 3 )ppm: 9.20 (s, 1H), 8.99-9.05 (m, 1H), 8.88-8.99 (m, 1H), 8.11-8.30 (m, 1H), 7.25-7.38 (d, 2H), 6.85-6.95 ( d, 2H), 3.92-3.76 (m, 10H), 3.42 (br, 2H), 3.18-3.14 (t, J=3.4Hz, 4H), 2.53 (s, 3H), 2.39 (s, 3H).

Embodiment 3

[0044] Example 3: 4-[5,6-Dimethyl-4-(4-morpholin-4-yl-phenylamino)-thieno[2,3-d]pyrimidine-2- Base]-piperazin-1-yl-pyridin-4-yl-methanone

[0045] The title product (48% yield) was obtained in the same manner as in Example 1 except that isonicotinoyl chloride hydrochloride was used instead of picolinoyl hydrochloride.

[0046] 1 H NMR (CDCl 3 )ppm: 8.75(d, J=5.6Hz, 2H), 7.46(d, J=9.0Hz, 2H), 7.34(d, J=1.6Hz, 2H), 7.04(s, 1H), 6.93(d, J=8.8Hz, 2H), 3.92-3.76(m, 10H), 3.41(br, 2H), 3.19-3.14(t, J=3.4Hz, 4H), 2.51(s, 3H), 2.39(s, 3H )

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Abstract

Disclosed herein are 5, ss-dimethylthieno [2, 3- d]pyrimidine derivatives useful as antiviral agents. More particularly, disclosed are 5, ss-dimethylthieno [2, 3- djpyrimidine derivatives represented by Formula 1, having an excellent inhibitory effect on the proliferation of hepatitis C virus (HCV) , pharmaceutically acceptable salts thereof, a preparation method thereof, and a pharmaceutical composition for the prevention and treatment of hepatitis C virus (HCV) , containing, as active ingredients, these compounds. The 5, 6-dimethylthieno [2, 3-d] pyrimidine derivatives represented by Formula 1 have an excellent effect of inhibiting the proliferation of hepatitis C virus and also have low toxicity. Thus, these compounds are available as agents for the prevention and treatment of hepatitis C.

Description

【Technical field】 [0001] The present invention relates to 5,6-dimethylthieno[2,3-d]pyrimidine derivatives useful as antiviral agents, and more particularly to pharmaceutical compositions for the prevention and treatment of hepatitis C, which The product contains as an active ingredient a novel 5,6-dimethylthieno[2,3-d]pyrimidine derivative having an excellent inhibitory effect on the proliferation of hepatitis C virus. 【Background technique】 [0002] Hepatitis C virus (HCV) is an enveloped virus belonging to the flavivirus family. Its genome is (+)-RNA (positive strand RNA), which is 9.6 kb in length and expresses a poly-protein consisting of 3,010 amino acids. The polyprotein is divided into 3 structural proteins and 6 nonstructural proteins by its host cell and viral enzymes. [0003] The 5' and 3' ends of the HCV genome have untranslated regions, in which the base sequences of almost all genotypes are highly conserved. The 330-341 nucleotides at the 5' end, and 98 nucl...

Claims

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Application Information

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IPC IPC(8): C07D495/04
CPCC07D495/04A61P1/16A61P31/12A61P31/14
Inventor 韩哲奎尹正赫金南斗金振婀
Owner 依柯斯制药
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