Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai
Reexamination Certificate
2001-11-27
2004-09-07
Badio, Barbara P. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ketone doai
C552S296000
Reexamination Certificate
active
06787571
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention generally relates to compounds having anti-inflammatory, anti-proliferative and analgesic activity and methods for using these compounds to reduce inflammation, cell proliferation and pain in mammals. Specifically, the present invention relates to natural and synthetic pseudopterosins, seco-pseudopterosins, diterpene aglycones, and tricyclic diterpenes which exhibit anti-inflammatory, anti-proliferative and analgesic activity when administered to a subject.
2. Description of the Related Art
Gorgonians (O. Gorgonacea, Ph. Cnidaria) are a diverse group of marine animals which are commonly known as sea feathers, sea whips and sea fans. Many species of gorgonians are found in abundance in the shallow-water reefs of the tropical Atlantic including regions of the Caribbean Sea. A few of the Caribbean gorgonians have been analyzed for their chemical content and found to be a source of many diverse organic substances such as steroids, prostaglandins, lactones, sesquiterpenoid derivatives and diterpenoid metabolites. Some of these substances have been found to be biologically active.
Since only a small percentage of the total number of gorgonian species have been examined for natural chemical products, there has been a continuing effort by a number of researchers to examine additional species in order to isolate possible novel natural products.
Recently, novel pseudopterosins, seco-pseudopterosins, diterpene aglycones, and tricyclic diterpenes were derived from
Pseudopterogorgia elisabethae
which was collected from the Florida Keys at a depth of 25 meters during August 1999 and identified by Frederick M. Bayer of the Department of Invertebrate Zoology, National Museum of Natural History, Smithsonian, Washington, D.C. 20560-0163. A voucher specimen, USNM 100430, was deposited with the Smithsonian.
SUMMARY OF THE INVENTION
In some embodiments, the present invention relates to a compound having the structural formula:
wherein R
1
is a hydrogen, alkyl, aryl, hydroxyalkyl, cycloalkyl, cycloalkenyl, carboxylic acid, alkylamino or amide group having from 2 to 20 carbon atoms, R
2
, R
3
, and R
4
are each independently hydrogen or an acyl residue having from 1 to 6 carbon atoms, R
5
is hydrogen, CH
3
, or CH
2
OH, and R
6
is an organo group such as a hydrocarbon having from 1 to 10 carbon atoms.
In some embodiments, the present invention relates to a compound having the structural formula:
wherein R
1
is a hydrogen, alkyl, aryl, hydroxyalkyl, cycloalkyl, cycloalkenyl, carboxylic acid, alkylamino or amide group having from 2 to 20 carbon atoms, R
2
, R
3
, and R
4
are each independently hydrogen or an acyl residue having from 1 to 6 carbon atoms, R
5
is hydrogen, CH
3
, or CH
2
OH, and R
6
is an organo group such as a hydrocarbon having from 1 to 10 carbon atoms.
In some embodiments, the present invention relates to a compound having the structural formula:
wherein R
1
is a hydrogen, or an alkyl or acyl residue having from 1 to 6 carbon atoms, and R
2
is an organo group such as a hydrocarbon having from 1 to 10 carbon atoms.
In some embodiments, the present invention relates to a pharmaceutical composition comprising a therapeutically effective amount of at least one of the above compounds or pharmaceutically acceptable prodrug or active metabolite thereof and a pharmaceutically acceptable excipient.
In some embodiments, the present invention relates a method of treating, preventing or inhibiting a disease or disorder associated with inflammation, cell-proliferation, or pain, comprising administering to a subject a therapeutically effective amount of one or more of the compounds or pharmaceutical compositions above.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed. The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute part of this specification, illustrate several embodiments of the invention and together with the description serve to explain the principles of the invention.
REFERENCES:
patent: 4447445 (1984-05-01), Jacobs et al.
patent: 4745104 (1988-05-01), Jacobs et al.
patent: 4849410 (1989-07-01), Jacobs et al.
patent: 5624911 (1997-04-01), Fenical et al.
Rodriguez et al., “Serrulatane Diterpenes with Antimycobacterial Activity Isolated from teh West Indian Sea WhipPseudopterogorgia elisabethae.” J, Nat. Prod., vol. 64, pp. 100-102, 2001, Published on Web Nov. 17, 2000.*
Coleman, AC, et al. (2000) “Radioactivity-Guided Isolation and Characterization of the Bicyclic Psuedopterosin Diterpene Cyclase Product fromPseudopterogorgia elisabethae” Tetrahedron 56:9569-9574.
Corey, EJ, et al. (1998) “A Direct and Efficient Stereocontrolled Synthetic Route to the Pseudopterosins, Potent Marine Antiinflammatory Agents” J. Am. Chem. Soc. 120:12777-12782.
Geller, T, et al. (1998) “Preparation of Helioporin D from the seco-Pseudopterosin Aglygonic: Revision of the Stereostructure of Helioporin D” Tetrahedron 39(15):1541-1544.
Harvis, CA, et al. (1988) “New Marine Diterpenoids, Including A Unique Hydroperoxide From A Caribbean Gorgonian Coral of the Genus Pseudopterogorgia” Tetrahedron Letters 29:35:4361-4364.
Lazerwith, SE, et al. (2000) “Syntheses and Stereochemical Revision of Pseudopterosin G-J Aglycon and Helioporin E” Am. Chem. Soc. Organic Letters 2:15:2389-2392.
Rodriguez, AD, et al. (2001) “Serrulatane Diterpenes with Antimycobacterial Activity Isolated from the West Indian Sea WhipPseudopterogorgia elisabethae” J. Nat. Prod. 64:100-1-2.
Rodriguez, AD; et al, et al. (2000) “Structually Diverse Terpenoids from the Sea WhipPseudopterogorgia elisabethae(Bayer)” Tetrahedron 56:9015-9023.
Look, SA, et al. (1986) “The Pseudopterosins: Anti-Inflammatory and Analgesic Natural Products from the Sea WhipPseudopterogorgia elisabethae” PNAS USA 83:6238-6240.
Look, SA, et al. (1986) “The Pseudoterosins: A New Class of Antiinflammatory and Analgesic Diterpene Pentosides from the Marine Sea WhipPseudopterogrgia elisabethae(Octocorallia)” J. Org. Chem. 51:5140-5145.
Look, SA, and W. Fenical (1987) “The Seco-Pseudopterosins, New Anti-Inflammatory Diterpene-Glycosides from a Caribbean Gorgnian Octocoral of the Genus Psuedopterogorgia” Tetrahedron 43(15):3363-3370.
Roussis, V, et al. (1990) “New Antiinflammatory Pseudopterosins from the Marine OctocoralPseudopterogorgia elisabethae” J. Org. Chem. 55:4916-4922.
Jacobs Robert S.
Kerr Russell G.
Badio Barbara P.
Smith Gambrell & Russell
Sundby Suzannah K.
LandOfFree
Anti-inflammatory compounds derived from Pseudopterorgorgia... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Anti-inflammatory compounds derived from Pseudopterorgorgia..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Anti-inflammatory compounds derived from Pseudopterorgorgia... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3231781