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Antiretroviral pyridine and quinoline derivatives

A technology of pyridine and sulfonylpyridine, applied in the field of pyridine and quinoline derivatives

Inactive Publication Date: 2005-03-09
UNIROYAL CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, there is considerable cross-tolerance between drugs acting on the same target

Method used

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  • Antiretroviral pyridine and quinoline derivatives
  • Antiretroviral pyridine and quinoline derivatives
  • Antiretroviral pyridine and quinoline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of 2-[[1-(5-amino-2-methylphenyl)ethyl]sulfonyl]-pyridine-N-oxide

[0045]

[0046] (compound 1)

[0047] Add 0.12 g Na 2 WO 4 , followed by the addition of 35% hydrogen peroxide over 20 minutes. The exothermic reaction was cooled using a room temperature water bath. The mixture was stirred for 20 min, then an additional 1.3 g of 35% H 2 o 2 . The mixture was allowed to warm to 35-43°C for 2 hours, then stirred at room temperature overnight. The mixture was then treated with 5 ml ethanol, 10 ml water and 5 ml cone. HCl and heated on a steam cone for 1 hour. The mixture was cooled, diluted with 20ml of water and filtered to remove solids. The filtrate was made basic with concentrated aqueous ammonium hydroxide to give a sticky solid. The solid was dissolved in 30 ml of water and 3 ml of cone. HCl and some insoluble material was filtered off. The filtrate was basified and a solid precipitated which was filtered off, washed with water and dried ov...

Embodiment 2

[0049] Preparation of 1,4-xylyl-bis-2-sulfonylpyridine-N-oxide

[0050]

[0051] (compound 23)

[0052] To a mixture of 14 g 1,4-xylyl-bis-2-thio-pyridine-N-oxide in 175 ml glacial acetic acid was added 20 ml H 2 o 2 (30% aqueous solution). The mixture was stirred over the weekend before adding another 8 ml of 30% H 2 o 2 , and the mixture was heated to 50-60 °C for 2 hours. The mixture was cooled and evaporated to dryness. Chloroform was then added and the mixture was boiled, then cooled and left overnight. The insoluble product was filtered off, washed with ethanol and then with chloroform. 13.6 g of final product were obtained, melting point 233-235°C. C 18 h 16 N 2 S 2 Anal. Calcd. for: C = 51.42; H = 3.84; N = 6.66. Found values: C=47.39, H=4.10; N=6.74.

Embodiment 3

[0054] Preparation of 1,4-[1,2,4,5-tetramethylbenzyl]-bis-(2'-sulfonylpyridine-N-oxide)

[0055]

[0056] (compound 25)

[0057] To a mixture of 1,4-[1,2,4,5-tetramethylbenzyl]-bis-(2'-thiopyridine-N-oxide) in 175 ml of glacial acetic acid was added 25 ml of 30% H 2 o 2 aqueous solution. The reaction mixture was stirred overnight, then an additional 25 ml of 30% H 2 o 2 aqueous solution, the mixture was heated at 50-60°C for 4 hours. Then 600ml of water and 100g of ice were added. The white solid was filtered off and dried at room temperature, melting point 242-244°C. The recovery rate was 2.2 g. Infrared spectra were consistent with this structure.

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Abstract

Certain pyridine and quinoline derivatives which inhibit replication of the retroviruses HIV-1, HIV-2 and human cytomegalovirus (HCMV) are provided. Pharmaceutical compositions useful in methods of treating or inhibiting certain retrovirus infections are described.

Description

field of invention [0001] The present invention relates to compounds useful as antiretroviral agents. More specifically, the present invention relates to pyridine and quinoline derivatives which inhibit the replication of the retroviruses HIV-1, HIV-2 and human cytomegalovirus (HCMV). Background of the invention [0002] There are currently about seven nucleoside reverse transcriptase (RT) inhibitors (NRTIs), about three non-nucleoside RT inhibitors (NNRTIs), and about six protease inhibitors (PIs) officially approved for use in HIV-infected individuals Treatment. Reverse transcriptase and protease are enzymes encoded by viruses. The clinical efficacy of individual drugs varies according to the properties and molecular targets of the drug. [0003] US Patent No. 5,268,389 describes certain thiocarboxylate compounds which are said to inhibit HIV replication. The paper asserts that the selectivity of these compounds for HIV-1 results from a highly specific interaction with...

Claims

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Application Information

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IPC IPC(8): A61K31/44A61K31/444A61K31/47A61P31/00A61P31/14A61P31/18C07D213/70C07D213/71C07D213/89C07D215/36C07D401/12
CPCC07D213/70C07D401/12C07D213/89C07D215/36C07D213/71A61P31/00A61P31/14A61P31/18
Inventor A·D·布鲁尔S·坎托M·A·德克瑟A·M·P·多维科J·W·哈里斯J·A·拉克迪J·B·皮尔斯H·L·普兰特W·A·哈里森
Owner UNIROYAL CHEM CO INC
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