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9-sulfonyl-9H-purine derivatives, and preparation method and use thereof

A sulfonyl and derivative technology, applied in the field of chemical medicine, can solve the problems of high treatment cost, serious toxic and side effects, and decreased replication ability of clemizole hydrochloride-resistant virus strains.

Active Publication Date: 2015-02-11
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional standard regimen approved by the FDA for the treatment of chronic hepatitis C is the combined application of PEG-interferon-α and ribavirin, which has the following problems: ①. Low effective rate; ②. Long treatment cycle and high treatment cost ; ③. Toxic and side effects are more serious
By inducing drug-resistant mutations, the replication ability of clemizole hydrochloride-resistant virus strains is greatly reduced, which means that the drug resistance of this type of NS4B inhibitor may be slower than that of protease inhibitors such as Boceprevir.

Method used

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  • 9-sulfonyl-9H-purine derivatives, and preparation method and use thereof
  • 9-sulfonyl-9H-purine derivatives, and preparation method and use thereof
  • 9-sulfonyl-9H-purine derivatives, and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] The synthesis of embodiment 1 intermediate 6-dimethylaminopurine

[0086]

[0087] Dissolve 0.465g (3mmol) of 6-chloropurine in ethanol, then add 1.25g (9mmol) of potassium carbonate and 0.725g (9mmol) of dimethylamine hydrochloride successively, and then heat to reflux for 12h. After the reaction is completed, the solvent is distilled off under reduced pressure. The remaining solid was suspended in water and stirred for 2 hours, and then filtered to obtain the product 6-dimethylaminopurine with a net weight of 0.392 g and a yield of 80.05%. Purity (HPLC) ≥ 94%

[0088] 1 H-NMR (400MHz, DMSO-D6) δ: 2.47(s, 6H, N(CH 3 ) 2 ), 7.96(s, 1H), 8.38(s, 1H), 13.71(s, 1H).

Embodiment 2

[0089] The synthesis of embodiment 2 intermediate 6-diethylaminopurine

[0090]

[0091] According to the preparation method of the intermediate 6-dimethylaminopurine, the raw materials were replaced with 6-chloropurine and diethylamine, washed and filtered after reaction to directly obtain 6-diethylaminopurine with a yield of 85.37%. Purity (HPLC) > 95%.

[0092] 1 H-NMR (400MHz, DMSO-D6) δ: 1.33(t, 6H, -CH 3 ), 1.33 (m, 2H, -CH 2 -), 7.97(s, 1H), 8.40(s, 1H), 13.66(s, 1H).

Embodiment 3

[0093] The synthesis of embodiment 3 intermediate 6-morpholino purine

[0094]

[0095] According to the preparation method of the intermediate 6-dimethylaminopurine, the raw materials were replaced with 6-chloropurine and morpholine, washed and filtered after reaction to directly obtain 6-morpholinopurine with a yield of 89.42%. Purity (HPLC) > 96%.

[0096] 1 H-NMR (400MHz, DMSO-D6) δ: 3.71(s, 4H, O(CH 2 ) 2 ), 4.21(s, 4H, -N(CH 2 ) 2 ), 8.14(s, 1H), 8.23(s, 1H), 13.07(s, 1H).

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Abstract

Disclosed are a 9-sulfonyl-9H-purine derivative as represented by Formula (I), a preparation method and use thereof. The compound represented by Formula (I) is provided with anti-chronic hepatitis C virus activity. [Formula I]

Description

technical field [0001] The invention relates to a 9-sulfonyl-9H-purine derivative, a preparation method and application thereof, and belongs to the field of chemical medicine. Background technique [0002] Chronic hepatitis C, a chronic liver disease caused by the hepatitis C virus (HCV), is the leading cause of cirrhosis and liver cancer, and is currently the leading cause of liver transplantation. According to the survey of the World Health Organization (WHO) in 1999, about 3% of people (170 million people) in the world are infected with HCV (J.Viral.Hepat.1999, 6: 35-47), and the infection rate in China is about 3.2% (40 million people) (Lancet Infect. Dis. 2005.5: 558-67), and the number of infected people tends to increase year by year. After the incubation period of 10-20 years, about 80% of these HCV-infected people will develop into chronic hepatitis C, 20% will further develop into liver cirrhosis, and 1%-4% will eventually develop into liver cirrhosis. Progressio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/40C07D473/38C07D473/34C07D473/30A61K31/52A61K31/5377A61P31/14A61P1/16
CPCC07D473/30C07D473/40C07D473/38C07D473/34A61P1/16A61P31/14
Inventor 余洛汀魏于全
Owner SICHUAN UNIV
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