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Cannabinol derivatives and pharmaceutical use thereof

A derivative, the technology of cannabinol, is applied in the field of treatment of diseases related to immune dysfunction, and can solve the problems of death, recurrence of malignant tumors, etc.

Inactive Publication Date: 2007-04-04
IMMUGEN PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, patients with multiple types of malignancies remain at high risk of recurrence and death

Method used

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  • Cannabinol derivatives and pharmaceutical use thereof
  • Cannabinol derivatives and pharmaceutical use thereof
  • Cannabinol derivatives and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0296] This example demonstrates the synthesis of compounds of formula I.

[0297] A mixture of 2,6-dimethoxyphenol (73.4 g, 0.48 mol), 2,6-dimethyl-2-heptanol (69.0 g, 0.48 mol) and methanesulfonic acid (95 mL) was stirred at 50 °C 3 hours, then stirred overnight at room temperature. The mixture was poured into ice water (600 mL) with stirring. The mixture was extracted with dichloromethane (2 x 200 mL). The extract was washed with water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure to obtain the product as an oil (130 g, 96%). Analysis of the substance (MS(FAB) m / z 281(MH) + ; 1 HNMR (CDCl 3 )δ0.80(d, 6H), 1.0-1.1(m, 4H), 1.27(s, 6H), 1.40-1.60(m, 3H), 3.89(s, 6H), 5.36(s, 1H), 6.54 (s,2H)) is shown to be 4-(1,1,5-trimethylhexyl)-2,6-dimethoxyphenol:

[0298]

Embodiment 2

[0300] This example demonstrates the synthesis of compounds of formula I.

[0301] The crude 4-(1,1,5-trimethylhexyl)-2,6-dimethoxyphenol obtained from Example 1 (130 g, 0.46 mol) was dissolved in anhydrous CCl 4 (100 mL) was cooled in an ice bath, and diethyl phosphite (70 mL, 0.54 mol) was added. To this stirred mixture was added triethylamine (75 mL, 0.54 mol) dropwise at a rate to maintain the temperature of the reaction mixture below 10 °C. The reaction mixture was stirred in the ice bath for 2 hours and at room temperature overnight. The mixture was then diluted with dichloromethane (200 mL), washed with water, 4N aqueous sodium hydroxide solution (100 mL), 1N aqueous hydrochloric acid solution (125 mL), water and saturated aqueous sodium chloride solution. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica column chromatography eluting with cyclohexane:EtOAc (7:1-3:1 gradient) to affo...

Embodiment 3

[0304] This example demonstrates the synthesis of compounds of formula I.

[0305] 4-(1,1,5-trimethylhexyl)-2,6-dimethoxyphenyl diethylphosphate (82 g, 0.197 mol) from Example 2 was dissolved in Et 2 A solution in O (175 mL) and THF (35 mL) was slowly added to liquid ammonia (450 mL) contained in a three-necked flask equipped with a mechanical stirrer, thermometer, dry ice condenser, and pressure-balanced addition funnel, while Small pieces of freshly cut lithium wire (2.8 g, 0.40 g-atom) were added at a rate to maintain the blue color. The reaction mixture was stirred for an additional 1 h, then the reaction mixture was stirred by adding saturated NH 4 Cl aqueous solution (22 mL) was used to quench the reaction. Diethyl ether (220 mL) was added and the ammonia was evaporated overnight. The residue was treated with water (220 mL). The layers were separated and the ether layer was washed with 4N NaOH (200 mL), water (2 x 200 mL) and saturated aqueous sodium chloride. The o...

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Abstract

The invention discloses a cannabinoid derivative and its medicinal application.

Description

[0001] This application is a divisional application of the patent application whose application number is 200410062002.X and the application date is March 22, 2000. [0002] invention technical field [0003] The present invention relates to the treatment of diseases associated with immune dysfunction, especially HIV diseases and neoplastic diseases. Background of the invention [0004] The retroviruses human immunodeficiency virus 1 and 2 (HIV) are the most common AIDS causative agents. Through a part of the viral envelope protein (gp120), HIV specifically binds with high affinity to the CD4 molecule on T-lymphocytes. After binding, the virus fuses with the cell membrane and internalizes. Inside the cell, viruses produce reverse transcriptase, which transcribes genomic RNA into DNA. This retro HIV transcript then integrates into the cellular DNA where it exists as a "provirus" for cell survival. Proviruses can be latent for ...

Claims

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Application Information

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IPC IPC(8): C07D413/06C07D409/06C07D407/06C07C39/12A61K31/05A61K31/135A61K31/19A61K31/352A61K31/535A61K31/661A61P31/18A61P37/02A61K
Inventor C·R·特拉维斯
Owner IMMUGEN PHARMA INC
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