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Novel antiviral pyrrolopyridine derivative and a production method for same

A drug and compound technology, applied in the field of new antiviral pyrrolopyridine derivatives and their preparation, can solve the problems of toxicity and inability to completely cure AIDS

Active Publication Date: 2014-09-24
ST PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they are not a complete cure for AIDS, and the drugs have sometimes shown toxicity and persistent variants against current therapeutic agents

Method used

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  • Novel antiviral pyrrolopyridine derivative and a production method for same
  • Novel antiviral pyrrolopyridine derivative and a production method for same
  • Novel antiviral pyrrolopyridine derivative and a production method for same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0101] Preparation Example 1: 2-tert-butoxy-2-(4-(4-chlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine-5- Base) Preparation of methyl acetate (1n and 1o)

[0102]

[0103]

[0104] Step 1: Preparation of 2-amino-1-(4-methoxybenzyl)-4,5-dimethyl-1H-pyrrole-3-carboxylic acid isopropyl ester (1b)

[0105] Acetoin (88 g, 1.0 mol) and 4-methoxybenzylamine (132 mL, 1.0 mol) were dissolved in cyclohexane (500 mL), and after installing a dean-stark still, the mixture was refluxed for 2 hours. Next, the reaction mass was cooled to 0° C., isopropyl cyanoacetate (126 mL, 1.0 mol) was slowly added thereto, and then the resulting material was refluxed for 2 hours in the same manner as above. The reaction mass was cooled to room temperature, and the solvent was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane / ethyl acetate=5 / 1), and 112 g (35%) of the target compound 1b were obtained as a brown solid.

[0106] 1 H-...

preparation Embodiment 2

[0147] Preparation Example 2: 4-(4-chlorophenyl)-1-(4-methoxybenzyl)-2,3,6-trimethyl-1H-pyrrolo[2, Another preparation method of 3-b]pyridin-5-yl)methanol (1g)

[0148]

[0149] Step 1: Preparation of (2-amino-1-(4-methoxybenzyl)-4,5-dimethyl-1H-pyrrol-3-yl)(4-chlorophenyl)methanone (1p)

[0150] Acetoin (17.3 g, 196.3 mmol) and p-methoxybenzylamine (25.5 mL, 196.3 mmol) were dissolved in toluene (400 mL), and after installing a dean-stark trap, the mixture was heated at reflux for 2 hours . It was believed that water produced in the reaction was quantitatively received in a distiller, and the reaction solution was cooled to 0°C. 2-Cyano-4-chloro-acetophenone (35.2 g, 196.3 mmol) was added to the reaction solution, and the resultant was stirred at the same temperature for 30 minutes, followed by heating to reflux for 2 hours. After the reaction solution was cooled to room temperature and concentrated under reduced pressure, dichloromethane (100 mL) was added thereto, and...

preparation Embodiment 3

[0158] Preparation Example 3: 2-tert-butoxy-2-(4-(4-chlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine-5- base) methyl acetate (1y) and (S)-2-tert-butoxy-2-(4-chloro-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine- Preparation of 5-yl)methyl acetate (1x)

[0159]

[0160] Step 1: Preparation of 4-chloro-1-(4-methoxybenzyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1r)

[0161] After compound 1f (34.9 g, 114.25 mmol) was dissolved in dimethylsulfoxide (230 mL), triethylamine (65 mL, 466.3 mmol) was added thereto, and the mixture was cooled to 10°C. Sulfur trioxide pyridine complex (55 g, 345.5 mmol) dissolved in dimethyl sulfoxide (120 mL) was added to the above solution within 1 hour. Thereafter, the resulting material was stirred at 25° C. for 3 hours to complete the reaction, and the reaction solution was poured into ice water (1500 mL). The resulting solid was filtered and washed well with water. The obtained solid was dissolved in ethyl acetate, dried...

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PUM

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Abstract

The present invention relates to a pyrrolopyridine derivative represented by chemical formula I below and to the racemic form or stereoisomeric form of same or a pharmaceutically acceptable salt of same, and to an antiviral composition comprising same as an active ingredient. The compound of chemical formula I below has outstanding physiological activity and selectively with respect to wild type and resistant HIV-1 and is useful as a therapeutic agent for acquired immune deficiency syndrome (AIDS).

Description

technical field [0001] The present invention relates to a compound with high selectivity and antiviral activity to viruses, especially to human immunodeficiency virus (HIV), its preparation method and its use. Background technique [0002] Acquired immunodeficiency syndrome (AIDS) is caused by human immunodeficiency virus (HIV) infection. There are two types of HIV: HIV-1 and HIV-2, and the most prevalent type globally is HIV-1. As the main drugs approved for AIDS, zidovudine, didanosine, zalcitabine, stavudine, lamivudine, Bacavir, tenofovir, and emtricitabine, and nevirapine, delavirdine, efavirenz, etravirine, and rilpivir that have been developed as non-nucleoside reverse transcriptase inhibitors (NNRTIs) Forest. As protease inhibitors (PIs), saquinavir, indinavir, ritonavir, nelfinavir, amprenavir, lopinavir, atazanavir, Fosamprenavir, tipranavir, and darunavir have been developed as fusion inhibitors with enfuviride (fuzeon), and as an entry inhibitor (entry inhibi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P31/18
CPCC07D471/04A61P31/12A61P31/18A61K31/437
Inventor 孙钟赞金奉镇金载鹤李一永尹昌洙李尚浩李钟娇
Owner ST PHARM CO LTD
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