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Dihydropyridine compounds and application thereof on preparing drugs for curing and/or preventing virus diseases

A technology of dihydropyridine and compounds, applied in antiviral agents, medical preparations containing active ingredients, organic chemistry, etc.

Active Publication Date: 2009-11-11
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no relevant report on the anti-hepatitis B virus of 1,4-dihydropyridine compounds

Method used

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  • Dihydropyridine compounds and application thereof on preparing drugs for curing and/or preventing virus diseases
  • Dihydropyridine compounds and application thereof on preparing drugs for curing and/or preventing virus diseases
  • Dihydropyridine compounds and application thereof on preparing drugs for curing and/or preventing virus diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0195] Example 1: 2-Methyl-4-phenyl-5-nitro-6-(4-methylphenyl)-1,4-dihydropyridine -3-Carboxylic acid ethyl ester

[0196]

[0197] Step 1: Synthesis of 2-nitro-p-tolyl ketone

[0198] 5.68g (94mmol) of nitromethane was slowly dropped into 20ml of anhydrous THF solution of 0.96g NaH (24mmol), the dropwise addition was completed, stirred at room temperature until no more bubbles emerged, and set aside for later use.

[0199] 2.72 g of p-toluic acid (20 mmol) and 3.89 g of carbonyldiimidazole (24 mmol) were refluxed in 50 ml of anhydrous THF for 1 h, and the reaction was complete as detected by TLC. The reaction solution was slowly added dropwise to the above-mentioned standby solution, the dropwise addition was completed, and the mixture was refluxed for 16 h. Cool, filter, dissolve in 150 ml of water, and adjust the pH to about 3.0 with hydrochloric acid. Extracted several times with ethyl acetate, combined organic layers and concentrated to give crude product. The...

Embodiment 2

[0204] Example 2: 2-Methyl-4-(2-chlorophenyl)-5-nitro-6-(4-methylphenyl)-1,4-dihydro Ethyl pyridine-3-carboxylate

[0205]

[0206] Using the method of Example 1, the benzaldehyde was changed to 2-chlorobenzaldehyde to obtain 0.25 g of yellow crystals, the yield was 12.1%, m.p. 205-206°C. 1 H NMR (DMSO-d6) (ppm): 1.107-1.143 (3H, t, CH 3 ), 2.494 (3H, s, CH 3 ), 2.498 (3H, s, ArCH 3 ), 4.002-4.019 (2H, m, CH 2 ), 5.689 (1H, s, CH), 7.226-7.353 (8H, m, ArH), 9.750 (1H, s, NH). MS(FAB)413.1(M + ).

Embodiment 3

[0207] Example 3: 2-Methyl-4-(3-chlorophenyl)-5-nitro-6-(4-methylphenyl)-1,4-dihydro Ethyl pyridine-3-carboxylate

[0208]

[0209] Using the method of Example 1, the benzaldehyde in it was changed to 2-chlorobenzaldehyde to obtain 0.21 g of yellow crystals, the yield was 10.2%, and the m.p. was 141-142°C. 1 H NMR (DMSO-d6) (ppm): 1.171-1.207 (3H, t, CH 3 ), 2.328 (3H, s, CH 3 ), 2.376 (3H, s, ArCH 3 ), 4.061-4.092 (2H, m, CH 2 ), 5.299 (1H, s, CH), 7.280-7.316 (8H, m, ArH), 9.818 (1H, s, NH). MS(FAB)413.0(M + ).

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Abstract

The invention relates to dihydropyridine compound and application thereof on preparing drugs for curing and / or preventing virus diseases, in particular to a compound shown as general formula (1) and isomers, salts for medicinal purpose or hydrate thereof, and each variable is defined in a specification. The invention also relates to a preparing method of a compound shown as general formula (1), and an application of compound shown as general formula (1) and isomers, salts for medicinal purpose or hydrate thereof, in particular to application in preparing drugs for curing and / or preventing hepatitis B.

Description

technical field [0001] The present invention relates to dihydropyridine compounds of general formula (I) and preparation methods thereof, pharmaceutical compositions comprising the above compounds, and such compounds or isomers or pharmaceutically acceptable salts or hydrates thereof as medicines such as antiviral Use of a medicament, especially as a medicament for the treatment and / or prevention of hepatitis B. Background technique [0002] Chronic hepatitis B is caused by hepatitis B virus (HBV). my country is a high-incidence area of ​​hepatitis B. The 1992-1995 national viral hepatitis seroepidemiological survey showed that the carrier rate of hepatitis B virus surface antigen (HBsAg) in Chinese population was 9.7%, and it was estimated that about 130 million people were HBV carriers. The research on the epidemic situation of viral hepatitis in my country found that the annual reported incidence of hepatitis B increased from 21.9 / 100,000 in 1990 to 53.3 / 100,000 in 2003,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/90C07D409/04A61K31/4422A61K31/4436A61P31/12A61P31/20
CPCC07D409/04C07D211/90A61P31/12A61P31/20
Inventor 李松郭真赵国明王莉莉关华肖军海钟武郑志兵谢云德李行舟王晓奎周辛波刘洪英
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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