Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Cyclopentanohydrophenanthrene ring system doai
Reexamination Certificate
1997-04-21
2001-01-23
Wu, Shean C. (Department: 1756)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Cyclopentanohydrophenanthrene ring system doai
C514S172000, C514S182000, C514S729000, C514S738000, C514S766000
Reexamination Certificate
active
06177415
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
All of the nonsteroidal anti-inflammatory drugs in current use inhibit both 5-lipoxygenase activity and 15-lipoxygenase activity. These enzymes are involved in prostaglandin biosynthesis and in lipoxin biosynthesis, respectively. Thus, these drugs effect a broad range of activities. In addition, most have side-effects related to irritation of the stomach. This invention relates to compounds which inhibit only the lipoxin biosynthetic pathway. This degree of specificity is very useful in treating atherosclerosis and asthma since the etiology of both pathological conditions involve a 15-lipoxygenase.
2. Description of the Related Art
Hopanoids are lipids which are pentacyclic triterpene derivatives of hopane. The compounds are cyclic and branched and are therefore generally considered very stable. They have been found preserved in the organic matter of sedimentary material with only small structural changes. They have thus been successfully utilized as biomarkers in geological sediments (Ourisson et al. 1984.
Annu. Rev. Microbiol.
vol 47, pp. 301-333; Ourisson et al. 1979.
Pure Appl. Chem.
vol. 51, pp. 709-729).
Hopanoids are also found in numerous species of bacteria and cyanobacteria (Rohmer et al. 1984.
J. Gen. Microbiol.
vol. 130, pp. 1137-1150), some species of fungi (Tsuda and Isobe. 1965.
Tetrahedron Lett.
vol. 27, pp. 709-729; van Eijk et al. 1986.
Tetrahedron Lett.
vol. 27, pp. 2522-2534), lichens (Ejiri and Shibata. 1974.
Phytochemistry.
vol. 13, p. 2871) and a few species of higher plants (Ourisson et al. 1979, supra). They are localized in bacterial membranes and, since they possess some structural similarity to sterols which are known membrane stabilizers in eukaryotes (Ourisson et al. 1984, supra), they have been implicated in both prokaryotic and eukaryotic membrane stabilization.
In addition, some hopanoids have been reported to show anti-tumor cell effects. Nagumo et al. (1991.
Toxicol. Lett.
vol. 58, pp. 309-313) tested the cytotoxicity of a hopanoid isolated from
Rhodopseudomonas palustris
against mouse leukemia cells, and Chen et al. (1995.
Biol. Pharm. Bull.,
vol. 18, no. 3, pp. 421-423) investigated cytotoxic effects of a number of hopanoids isolated from
Acetobacter aceti,
also against mouse leukemia cells.
Heretofore, there have been no reports or suggestions of anti-inflammatory activity exhibited by hopanoid compounds.
SUMMARY OF THE INVENTION
We have discovered that naturally-occurring hopanoids possess unique properties in that they block only one biochemical pathway, i.e. that of lipoxin biosynthesis.
In accordance with this discovery, it is an object of the invention to provide a composition comprising hopanoids effective for blocking lipoxygenases and lipoxin biosynthesis thus serving as an effective anti-inflammatory agent.
Other objects and advantages will become readily apparent from the following description.
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Parthasarathy et al.,Prog. Lipid Res., vol. 31, No. 2, p. 127-143 (1992).
Nagumo et al.,Toxicology Letters, vol. 58, p. 309-313 (1991).
Chen et al.,Biol. Pharm. Bull., vol. 18(3), p. 421-423 (1995).
Roth et al.,Analytical Biochemistry, vol. 224, p. 302-308 (1995).
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Safayhi, H., et al. “Anti-Inflammatory Actions of Pentacyclic Triterpenes”,Planta Med., vol. 63, pp. 487-493, 1997.
Hicks Kevin B.
Moreau Robert A.
Fado John D.
Graeter Jaenelle S.
Silverstein M. Howard
The United States of America as represented by the Secretary of
Wu Shean C.
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