Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-09-16
2000-07-11
O'Sullivan, Peter
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
424 58, 4241951, 426606, 426607, 554115, 554183, 554185, 514547, 514567, 514570, 514648, 514690, 514725, 514728, 514734, A61K 31355, A61K 3107, A61K 3112, A61K 3578
Patent
active
060873914
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a method of rendering organic compounds containing hydrophilic groups soluble in fatty systems. The invention further relates to a group of novel chemical complexes formed in the method and to the use of these complexes for various purposes to be defined more specifically below.
More specifically the present invention concerns a method of making compounds containing hydrophilic groups more lipophilic, i.e. fat soluble. This is achieved due to the fact that according to the invention hydrophilic compounds form stable, fat soluble complexes with a lipophilic carrier.
Traditionally compounds are rendered fat soluble by derivatization, i.e. the compounds are modified chemically. This involves e.g. addition of an aliphatic side chain which is capable of rendering the compounds more lipophilic. In the textbook "Drug Formulation" (I. Racz, Chapter 4, John Wiley and Sons, 1989) esterification with a suitable fatty acid is mentioned as a method to make compounds more lipophilic. However, derivatization entails several problems. After the chemical modification the compounds often exhibit another degree of biological activity, whereby the desired activity may be lost. Further, the derivatization of a known harmless compound may lead to a new compound, the toxicity of which most be evaluated fundamentally, which is comprehensive and also expensive.
In the 1960's the discovery of liposomes called for attention. Liposomes consist of one or more concentric spheres of lipid bilayers surrounding aqueous compartments. Typically liposomes are used to encapsulate hydrophilic compounds in aqueous solution to obtain improved stability or biological uptake, i.e. in cosmetics. If liposomes are incorporated in a fatty phase, the hydrophilic compounds remain separated from the fatty phase, because in fact the hydrophilic compounds are present as a heterogeneous dispersion. Technically, and also with a view to the formulation of pharmaceuticals, the success of liposomes has been rather limited (see "Drug Targeting and Delivery", Chapter 6, edited by H. E. Junginger, Ellis Horwood 1992).
Liposomes do not represent an alternative to the present invention, since liposomes do not render the hydrophilic compounds lipophilic. The incorporation of compounds in liposomes may further give rise to problems and thus necessitate a derivatization of the compounds.
Complex formation is mentioned in the pharmaceutical literature, but only in connection with the improvement of the water solubility of the coupounds and as a problem related to sedimentation in certain combination pharmaceuticals.
A number of naturally occurring phenolic compounds, i.a. many flavones, flavone glycosides, phenolic di- and tri-terpenes, gingerols and other substances, exhibit a limited solubility in fatty as well as in aqueous systems. In spite of very interesting chemical and pharmacological properties many compounds, therefore, only find limited use as active agents in e.g. pharmaceuticals, foodstuffs and cosmetic products. Thus ginger (zingiber officinale) contains a number of 4-hydroxy-3-methoxyphenyl (HMP) compounds having interesting chemical and pharmacological effects, such as a potent antioxidant effect and a modulating effect on the functions of certain immune cells, which effects, however, are only sparsely exploitable due to the low solubility.
Spice plants of the labiatae family, such as sage, rosemary and thyme, contain phenolic diterpenes (Schwarz and Ternes, Z. Lebensmitteluntersuch. und Forsch. 195, 99 (1992) which can be extracted to yield an antioxidant with a strength comparable to that of the common antioxidant BHA (butylated hydroxyanisole). The above-mentioned phenolic compounds can be obtained from the resin by extraction of the oleoresins (mixture of ethereal oils and resins) of the plants. Traditionally, the oleoresins are extracted with an organic solvent, such as ethanol or methanol, which is subsequently distilled off. A more gentle way to extract the oleoresins is to use supercritical extraction with CO.sub.
REFERENCES:
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Japanese patent 57022681, published Feb. 5, 1982 (abstract only).
Japanese patent 58208383, published Dec. 5, 1983 (abstract only).
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Japanese patent 63174912, published Sep. 19, 1988 (abstract only).
Japanese patent 02204417, published Aug. 14, 1990 (abstract only).
Japanese patent 06113742, published Apr. 26, 1994 (abstract only).
Tesko et al., Chem. Abst. 72:131284, 1970.
Tateo et al., Chem. Abst. 110:22543, 1989.
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