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Deuterium-containing azacyclo-dione compound for treatment of influenza

A compound and technology of nitrogen heterocycle, applied in the field of deuterium-containing nitrogen heterocycle diketone compound and its preparation for the treatment of influenza, can solve problems such as shortages

Inactive Publication Date: 2020-06-09
维清生物科技(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] At present, there is still a lack of a drug or its composition clinically used as an anti-influenza drug

Method used

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  • Deuterium-containing azacyclo-dione compound for treatment of influenza
  • Deuterium-containing azacyclo-dione compound for treatment of influenza
  • Deuterium-containing azacyclo-dione compound for treatment of influenza

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0187]

[0188] 1'-(1,2,3,4-tetradeutero-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-5'-hydroxyl -1",2'-dihydrospiro[cyclobutane-1,3'-pyrido[1,2,2-b]pyridazine]-4',6'-dione

[0189] The specific reaction equation is as follows:

[0190]

[0191] Step A: 5'-(Benzyloxy)-1'-(7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl-1,2,3 ,4-D4)-1',2'-dihydrospiro[cyclobutane-1,3'-pyrido[1,2-b]pyridazine]-4',6'-dione (compound 1.1)

[0192] Intermediate D (130mg, 0.42mmol) was dissolved in N,N-dimethylformamide (0.5mL), then Intermediate J (102.7mg, 1.52mmol) and T3P / DMF (50%) solution (5mL ) into the reaction solution, and the reaction was stirred at 100°C for 1 hour. The reaction was quenched with saturated sodium bicarbonate solution (5 mL), the aqueous phase was extracted twice with ethyl acetate (15 mL), and the organic phases were combined. The organic phase was dried over anhydrous sodium sulfate. Filtered, spin-dried, and purified to obtain yellow solid compoun...

Embodiment 2

[0196] Using the same reaction conditions as in Example 1, Compound Example 2 was obtained from Intermediate A and Intermediate I through a two-step reaction.

[0197]

[0198] 1-(7,8-difluoro-1,2,3,4-tetradeuterium-6,11-dihydrodibenzo[b,e]thieheptin-11-yl)-5-hydroxyl-2, 3-Dihydro-1H-pyrido[1,2-b]pyridazine-4,6dione

[0199] LCMS ESI(+) m / z: 431.1(M+1).

Embodiment 3

[0202]

[0203] 1-(7,8-Difluoro-1,2,3,4-tetradeuterium-6,11-dihydrodibenzo[b,e]thiepin-11-yl-1,2,3,4 -d4)-5-Hydroxy-3,3-dimethyl-2,3-dihydro-1H-pyrido[1,2b]pyridazine-4,6-dione

[0204] LCMS ESI(+) m / z: 459.1(M+1).

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Abstract

The invention provides a deuterium-containing azacyclo diketone compound, which is a compound represented by the following structural formula or a pharmaceutically acceptable salt thereof, has proliferation inhibition activity on influenza (influenza) viruses, and particularly inhibits influenza virus proliferation by inhibiting influenza-related cap-dependent endonuclease, so that influenza is treated.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a deuterium nitrogen-containing heterocyclic diketone compound for treating influenza and a preparation method thereof. [0002] Background of the invention [0003] Influenza viruses belong to the Orthomyxoviridae family of viruses and are negative-sense single-stranded RNA viruses. There are three known influenza viruses: Influenza A, Influenza B, and Influenza C. The acute respiratory infection that the infection of influenza virus can cause, can cause other respiratory tract viral infection simultaneously, comprises upper respiratory tract and lower respiratory tract viral infection. Upper respiratory tract viral infection involving the nose, sinuses, pharynx and / or larynx. Viral infections of the lower respiratory tract involve the respiratory system below the vocal cords, including the trachea, main bronchi, and lungs. Infection with influenza viruses is the leading cause...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61P31/16A61K31/5025
CPCA61P31/16C07B2200/05C07D471/04Y02P20/55
Inventor 沈旺党奎峰刘劲强蔡雨婷陈春明韩巧靡佳晨沈家磊孙亚波王鑫张超马随军赖新忠
Owner 维清生物科技(上海)有限公司