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Triazine compound as well as preparation method and application thereof

A compound and triazine technology, applied in the field of preparation of triazine compounds, can solve the problems of single structure, the lack of non-covalent high-efficiency 3CLpro small molecule inhibitors, etc., and achieve small toxic side effects, good inhibitory activity, good effect of treatment

Active Publication Date: 2022-07-26
YAOKANG ZHONGTUO (JIANGSU) PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is to overcome the single structure of existing broad-spectrum antiviral drugs and the lack of non-covalent high-efficiency 3CLpro small molecule inhibitors, and provide a triazine compound, its preparation method, pharmaceutical composition and application

Method used

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  • Triazine compound as well as preparation method and application thereof
  • Triazine compound as well as preparation method and application thereof
  • Triazine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1 Synthesis of compound IV-1

[0070]

[0071] Step 1: Synthesis of Compound 2

[0072] To a solution of compound 2 (100.0 mg, 0.47 mmol) in N,N-dimethylformamide (10 mL), potassium hydroxide (105.5 mg, 1.88 mmol) and iodine (239 mg, 0.94 mmol) were added, and the reaction was carried out at room temperature. After 3 hours, TLC monitored the completion of the reaction. Saturated sodium sulfite solution was added to quench the reaction. The aqueous phase was extracted with ethyl acetate (10 mL*2), washed with water (20 mL*2), and washed with saturated salt (20 mL) with anhydrous sodium sulfate. Dry and concentrate by column chromatography to obtain compound 3 (134.8 mg, 85%). 1 HNMR (300 MHz, CDCl 3 ) δ 8.79 (s, 1H), 7.70 (s, 1H), 3.90 (s, 3H).

[0073] Step 2: Synthesis of Compound 3

[0074] To a solution of compound 3 (120.0 mg, 0.36 mmol) in deuterated acetic acid (8 mL), sodium acetate (97.9 mg, 0.72 mmol) was added, the dropwise addition was complete...

Embodiment 2

[0077] Example 2 Synthesis of compound IV-2

[0078]

[0079] To compound 4 (30 mg, 0.17 mmol) was added deuterated acetic acid (2 mL), refluxed at 120 °C for 25 hours, TLC monitored the completion of the reaction, and concentrated under reduced pressure to obtain compound IV-2 (28 mg, 92%). 1 H NMR (300 MHz, CDCl 3 ) δ 7.44(s, 1H), 5.11 (d, J = 7.1 Hz, 1H), 4.95 (d, J = 7.1 Hz, 1H), 3.85 (s, 3H).

Embodiment 3

[0080] Example 3: Synthesis of Compound S1

[0081]

[0082] Step 1: Synthesis of Compound 6

[0083] Compound 5 (18 g, 78.8 mmol) was dissolved in acetonitrile (240 mL), to the above solution was added compound 11 (26 g, 118.8 mmol) and K 2 CO 3 (16.4 g, 118.8 mol), the reaction solution was heated to reflux for 3 h. The reaction solution was cooled to room temperature, filtered with suction, the filtrate was concentrated, and separated and purified by column chromatography (PE:EA=30:1) to obtain compound 6 (23.5 g, 80%). 1 H NMR (300 MHz, CDCl 3 ) δ 1.33 (3H, t, J = 7.4 Hz), 1.65 (9H, s), 3.15 (2H, q, J =7.4 Hz), 5.03 (2H, s), 6.91−7.01 (2H, m).

[0084] Step 2: Synthesis of Compound 7

[0085] Compound 6 (20 g, 51.9 mmol) was dissolved in TFA (39 mL), the reaction was stirred at room temperature for 6 h, the stirring was stopped, the TFA was evaporated under reduced pressure, slurried with ether, filtered with suction, the filter cake was collected, and dried in vac...

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Abstract

The invention discloses a triazine compound with a structure as shown in a general formula I or pharmaceutically acceptable salt, isomer, metabolite, prodrug, solvate or hydrate, pharmaceutical composition and application thereof. The compound disclosed by the invention overcomes the defects of single structure, lack of non-covalent and non-peptide high-efficiency small-molecule inhibitors and the like of the existing broad-spectrum antiviral drugs, and the compound disclosed by the invention has very good inhibitory activity on 3C-like cysteine protease and has a good treatment effect on infectious diseases.

Description

technical field [0001] The invention belongs to the field of innovative medicinal chemistry, and relates to a triazine compound, its preparation method, pharmaceutical composition and application. Background technique [0002] SARS-CoV-2 is a highly pathogenic, massively prevalent zoonotic virus that belongs to the Coronaviridae family with SARS-CoV-1 and MERS-CoV. These three viruses differ from several other coronaviruses, HCoV-NL63, HCoV-229E, HCoV-OC43 and HCoVHKU1, which are capable of causing severe respiratory disease. Symptoms of SARS-CoV-2 infection range from asymptomatic disease to moderate and severe pneumonia, and life-threatening complications including hypoxic respiratory failure, acute respiratory distress syndrome, multisystem organ failure, and ultimately death. Even more frightening is that the virus is not only highly contagious, but can be spread by asymptomatic infected individuals and those in the symptomatic and pre-symptomatic stages. Although many...

Claims

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Application Information

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IPC IPC(8): C07D403/14C07D231/56A61P31/12A61P31/20A61P31/14A61P31/18A61P31/16A61P11/00A61K31/53
CPCC07D403/14C07D231/56A61P31/12A61P31/20A61P31/14A61P31/18A61P31/16A61P11/00
Inventor 刘春河
Owner YAOKANG ZHONGTUO (JIANGSU) PHARMA TECH CO LTD
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