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Therapeutic compositions and methods of treatment with capsianoside-type compounds

Inactive Publication Date: 2008-05-01
BMB PATENT HLDG CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007] The present invention is directed to certain compounds and their use as therapeutic agents, and in particular as analgesics and anti-inflammatory agents. Such compounds include, for example, various diterpene monoglycosides and diterpene diglycosides which may be synthetically or semi-synthetically produced, or which may be isolated from the fruit of the genus Capsicum, and in particular may be isolated from sweet bell peppers (C. annuum). Pharmaceutically-acceptable salts, enantiomers, diasteriomers, racemic mixtures, enantiomerically-enriched mixtures, solvates, and prodrugs of such compounds are also included in the present invention. Pharmaceutical compositions, combinations of compounds of the present invention and other therapeutic ingredients, such as analgesics and anti-inflammatory agents, are also provided by the present invention, as are methods of using such pharmaceutical compositions, compounds and combinations. Objects of the present invention include providing pharmaceutical compositions, compounds, and combinations for the treatment of pain, discomfort and inflammation, in a safe and effective manner.

Problems solved by technology

As such, although anesthetics can be used for pain management, their utility is limited by their inhibition of these other sensory pathways.
Narcotic analgesics primarily act on the central nervous system and carry potentially life-threatening side-effects such as addiction, impaired higher cortical function and depressed respiration.
Such non-narcotic analgesics can be limited in their ability to control pain and may have the side effects of chemical irritation, anticoagulation, myocardial infarction and stroke.
However, the therapeutic usefulness of capsaicin is limited due to an adverse side effects profile that includes burning sensations and erythema, and such side effects may persist over time.
Furthermore, as such extracts must be derived from naturally-occurring fruit, their production and practical use is limited.
However, no experimental or clinical data is known to have been reported that establishes the therapeutic utility of such compounds.

Method used

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  • Therapeutic compositions and methods of treatment with capsianoside-type compounds
  • Therapeutic compositions and methods of treatment with capsianoside-type compounds
  • Therapeutic compositions and methods of treatment with capsianoside-type compounds

Examples

Experimental program
Comparison scheme
Effect test

example 1

Analgesic Bioassay Protocol

[0062] A rat hindpaw assay was used to determine the therapeutic effectiveness of various extracts / compounds as analgesics in the present invention.

[0063] Sprague-Dawley rats (225-250 g, male) were anesthetized with urethane and placed on their sides on a disposable Chux pad. Both hindpaws for each rat were blackened with India ink which was allowed to dry for 10 minutes. An ELH projector lamp calibrated to a standard mW / cm2 was used as a pain stimulus and was condensed into an area of 5×15 mm on each hindpaw and placed perpendicular to, and 72 mm from, each hindpaw.

[0064] Multiple baseline hindpaw withdrawal latency times were recorded (in seconds) for each medial and each lateral surface of each hindpaw. Subsequently, 100 μl of 1 μmolar capsaicin was applied with a pipette to cover one hindpaw of each animal and allowed to dry for 10 minutes, rendering the capsaicin-treated hindpaw hypersensitive to pain stimulus relative to the non-capsaicin treated ...

example 2

Isolation of Analgesic Compounds

[0067] Twelve (12) sweet green bell peppers (Capsicum anuum ssp. grossum) with stems, seeds and septae removed were put through a juice extractor (Panasonic model # MJ66PR) to yield 1200 ml liters of unfiltered juice. The juice was suction filtered with coarse filter paper through a Buchner funnel to yield 1.0 liters of filtered green pepper juice.

[0068] 500 ml of filtered juice was partitioned with 500 ml of diethyl ether to remove waxes and chlorophylls. This partitioning was performed for a total of three times. Three layers were separated, the aqueous layer, the ether layer and an intermediate flocculent layer. Aliquots of each layer were tested by the Analgesic Bioassay (Example 1). Only the aqueous layer exhibited analgesic activity.

[0069] The aqueous layer was rotary evaporated at room temperature to 10 ml of a light brown gel which was triturated with two successive volumes of 100 ml methanol at room temperature to precipitate out long chai...

example 3

Sub-Fractionation of Fraction E

[0072] 1.0 g of the original concentrated methanolic extract was fractionated by column chromatography with a stationary phase of C-18 reverse phase silica gel (Sep-Pak 35 cc C-18 10 g, Waters, Chicago, Ill.). 20 ml fractions were eluted with a gravity-fed, gradient solvent system of 0:1 to 1:0 methanol / water (mobile phase) in increments of 20% methanol per step.

[0073] 1.0 g of the concentrated 80% methanol fraction was re-fractionated by column chromatography with a stationary phase of C-18 reverse phase silica gel (Sep-Pak 35 cc C-18 10 g, Waters, Chicago, Ill.). 20 ml fractions were eluted with a gravity-fed, gradient solvent system of 0:1 to 1:0 methanol / water (mobile phase) in increments of 20% methanol per step. The 80% methanol fractions were collected in 5 ml aliquots labeled EEa, EEb, EEc and EEd. All of these sub-fractions exhibited analgesic activity with the greatest analgesic activity noted in fraction EEa.

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Abstract

The present invention discloses the use of certain compounds as therapeutic agents, and in particular as analgesics and anti-inflammatory agents. Such compounds include, for example, certain diterpene monoglycosides and diterpene diglycosides. The compounds of the present invention may be synthesized or isolated from the fruit of the genus Capsicum, and in particular may be isolated from sweet bell peppers (C. annuum). Pharmaceutically-acceptable salts, enantiomers, diasteriomers, racemic mixtures, enantiomerically-enriched mixtures, solvates, and prodrugs of such compounds are also disclosed. Pharmaceutical compositions and methods of using such compounds, including pharmaceutical compositions and methods of using such compounds in combination with one or more active ingredients, are also disclosed.

Description

RELATED APPLICATION DATA [0001] This application claims priority to U.S. Provisional Patent Application No. 60 / 863,302, filed on Oct. 27, 2006, the entirety of which is hereby incorporated by reference.FIELD OF THE INVENTION [0002] The present invention relates to analgesic compositions and methods with compounds known as capsianosides and related compounds. The compounds may be synthesized or they may be isolated from the fruit of the genus Capsicum, in particular Capsicum annuum. This invention further relates to the therapeutic uses of such compounds as analgesics and as anti-inflammatory agents. BACKGROUND OF RELATED TECHNOLOGY [0003] A primary focus of drug research is the development of analgesics for pain management. Analgesics render sensory pathways insensible or less sensible to pain, whereas anesthetics act on all sensory pathways rendering them insensible to pain, temperature, touch, proprioception and skeletal muscle tone. As such, although anesthetics can be used for p...

Claims

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Application Information

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IPC IPC(8): A61K31/70A61K31/7016A61P25/04A61P29/00
CPCA61K31/70A61K31/7016A61K31/7028C07H15/10A61K45/06C07H3/04A61K36/81A61P25/04A61P29/00A61P43/00
Inventor BELGOROD, BARRY MILES
Owner BMB PATENT HLDG CORP
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