Topical formulations of resorcinols and cannibinoids and methods of use

A technology of resorcinol and cannabinoids, applied in the field of HIV infection, can solve the problems of increasing the risk of HIV transmission and lack of recognition

Inactive Publication Date: 2005-08-10
IMMUGEN PHARMA INC
View PDF11 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The use of barrier devices such as condoms can prevent STDs, but requires the cooperation of the male partner, and its lack of recognition is undoubtedly its disadvantage
In addition, detergent spermicides such as nonoxynol-9 (N-9) have been shown to actually increase the risk of HIV transmission

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Topical formulations of resorcinols and cannibinoids and methods of use
  • Topical formulations of resorcinols and cannibinoids and methods of use
  • Topical formulations of resorcinols and cannibinoids and methods of use

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0420]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 an oily product (130 g, 96%). Analysis of the substance (MS(FAB) m / z 281(MH) + ; 1 H NMR (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-methoxyphenol (hereinafter referred to as IMG-502):

[0421]

preparation Embodiment 2

[0423] Crude 4-(1,1,5-trimethylhexyl)-2,6-dimethoxyphenol (130 g, 0.46 mol) from Example 1 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 controlled 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 afford 103 g (54%) of product as a colorless waxy oil. Analysis of the substance (M...

preparation Embodiment 3

[0426] 4-(1,1,5-trimethylhexyl)-2,6-methoxyphenyl 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 vessel 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 organic extracts were dried (MgSO 4 ) and concentrated under reduced pressure...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

In one aspect, the invention provides a method for preventing the transmission of HIV from one individual to another. In accordance with the method, a pharmacologicallyacceptable composition including at least one resorcinol derivative compound and / or cannabinoid (e.g., cannabdol derivatives, Delta8-THC derivatives, cannabichromene derivatives, cannabidiol derivatives, cannabigerol derivatives) (including combinations thereof) is administered topically to a first individual harboring HIV, or to a second individual at risk of infection with HIV, proximate in time with contact between the first individual and the second individual. The invention also provides topical formulations of at least one resorcinol and / or cannabinoid and water insoluble polymers as hydrogels.

Description

technical field [0001] The present invention relates to the prevention of human-to-human transmission of HIV infection. Background technique [0002] Sexual transmission is the major form of HIV disease spread globally, with women representing the largest number of individuals exposed to the virus through infected male partners. It is now well established that sexually transmitted diseases (STDs) place people at greater risk of HIV infection, with women suffering the most consequences of unprotected sex with highly promiscuous partners. Clearly, a need exists for a topical agent that a woman can apply prior to intercourse to provide her with protection from HIV infection. Ideally the agent will be able to act within the short time of application without interfering with the normal protective vaginal flora and without any particularly unpleasant properties such as odor, irritation or alteration of the mucosal barrier making it abrasive to microorganisms more sensitive. The...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/00A61K31/35A61K31/353
CPCA61K31/353A61K31/35A61K9/0034
Inventor C·R·特拉维斯
Owner IMMUGEN PHARMA INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap