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Novel pyrrolopyridine derivative, method for producing same, and use thereof

A compound, chemical formula technology, applied in the field of antiviral compounds, can solve the problem that AIDS cannot be completely cured

Active Publication Date: 2019-11-15
ST PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, despite these efforts, there is no complete cure for AIDS, and even the development of new therapeutic agents is constantly called for due to drug toxicity issues and the manifestation of drug resistance against existing therapeutic agents

Method used

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  • Novel pyrrolopyridine derivative, method for producing same, and use thereof
  • Novel pyrrolopyridine derivative, method for producing same, and use thereof
  • Novel pyrrolopyridine derivative, method for producing same, and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0072] Preparation Example 1: Preparation of 4-(chloromethyl)-1-methyl-1H-pyrazole hydrochloride

[0073] In (1-methyl-1H-pyrazol-4-yl)methanol (380 mg, 3.39 mmol) and dichloromethane (1.8 mL) and triethylamine (2 drops) were added and cooled to 0°C. A solution obtained by dissolving thionyl chloride (0.62 mL) in toluene (1.8 mL) was slowly added thereto, followed by stirring at 30° C. for 2 hours. For the reaction solution, the solvent and excess thionyl chloride were removed under reduced pressure to obtain the target compound. This material was used in the next reaction without purification.

preparation example 2

[0074] Preparation Example 2: Preparation of 4-(bromomethyl)-5-chloro-1,3-dimethyl-1H-pyrazole

[0075] (5-Chloro-1,3-dimethylmethyl)-1H- Pyrazol-4-yl)methanol (937 mg, 5.8 mmol) was dissolved in dichloromethane (40 mL) and cooled to 0°C. A solution obtained by diluting phosphorus tribromide (0.54 mL, 5.8 mmol) in dichloromethane (5 mL) was slowly added thereto, followed by stirring at room temperature for 1.5 hours. For the reaction liquid, the solvent was removed under reduced pressure to obtain the target compound. This material was used in the next reaction without purification.

Embodiment 1

[0076] Example 1: (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2,3,6-trimethyl-1-((1-methyl-1H -pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid

[0077]

[0078] Step 1: Make methyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3 -b] pyridin-5-yl) acetate (700mg, 1.69mmol) was dissolved in dimethylformamide (14mL), cesium carbonate (2.75g, 8.45mmol) and 10 drops of triethylamine were added, and the temperature was adjusted to 40°C, and then the compound obtained in Preparation 1 (560 mg, 3.39 mmol) was added separately over 1 hour. The reaction was completed by stirring at the same temperature for 18 hours. After cooling the reaction solution with ice water, water (50 mL) was added and stirred for 10 minutes. The resulting solid was filtered and washed with water. The obtained solid was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1 / 2 and 1 / 1) without drying to obtain the target compound (430 mg, 50%...

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Abstract

The present invention relates to a novel pyrrolopyridine derivative represented by chemical formula I, a racemate thereof, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, and a method for producing same. A compound represented by chemical formula I below has high selectivity and biological activity against the human immunodeficiency virus (HIV), while having low toxicity, thereby being useful as a therapeutic agent for a viral infection, particularly an HIV infection.

Description

technical field [0001] The present invention relates to an antiviral compound, especially a compound with high selectivity and physiological activity against human immunodeficiency virus (HIV), its preparation method and use. Background technique [0002] AIDS (Acquired Immuno Deficiency Syndrome; AIDS) is caused by human immunodeficiency virus (Human Immunodeficiency Virus; HIV) infection. There are two types of HIV, HIV-1 and HIV-2, and the type that spreads all over the world is HIV-1. In order to treat AIDS, according to the mechanism of action of HIV, enzyme inhibitors have been developed. According to their action sites, these enzyme inhibitors are classified into Nucleoside Reverse Transcriptase Inhibitor (NRTI), Protease Inhibitor (Protease Inhibitor). Inhibitor: PI), fusion inhibitor (Fusion Inhibitor), Integrase Inhibitor (Integrase Inhibitor). [0003] Integrase inhibitors are classified into catalytic site (catalytic site) inhibitors and non-catalytic site (non...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61K31/4155
CPCA61P31/18C07D471/04A61K31/437A61K31/4155
Inventor 金奉镇李一永金载鹤申洪锡孙锺赞李锺娇金庆镇金旭镒南炛廷
Owner ST PHARM CO LTD