Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-04-16
2001-10-09
Rotman, Alan L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S450000, C549S298000, C549S348000
Reexamination Certificate
active
06300371
ABSTRACT:
TECHNICAL FIELD
This invention relates to a chemical compound, and more particularly to diterpene derivative, rameswaralide, derived from coral.
BACKGROUND OF THE INVENTION
Inflammatory disorders are a leading cause of mortality and morbidity in the United States and affect people worldwide. Steroids and non-steroidal anti-inflammatory drugs (NSAIDs) are the most widely used therapeutic modalities. Steroids have been associated with a number of additional disorders associated with long term use, such as liver dysfunction.
Soft corals are a rich source of terpenoids with diverse structures and various biological activities. Prior studies have shown that members of the genus Sinularia produce unusual sesquiterpenes, cembrane diterpenes and sterols.
SUMMARY OF THE INVENTION
It has been discovered that rameswaralide and various derivatives of rameswaralide can function as effective anti-inflammatory agents.
In a first aspect, the invention features a diterpene molecule according to the structure of formula I:
and tautomers, anhydrides, and salts thereof. In a another embodiment, the compound according to formula I has a double bond between C
3
and C
4
, a double bond between C
12
and C
13
, a double bond between C
15
and C
16
, and wherein C
3
is further bonded to a R
1
, C
8
is further bonded to R
2
, and C
18
is a short chain alkoxy carbonyl and has a general structure as set forth in formula II:
wherein R
1
is a hydrogen, hydroxyl group or a short chain alkanoyloxy group, and R
2
is a hydrogen, hydroxyl group or a short chain alkanoyloxy group.
Additionally, the diterpene molecule can have a structure as set forth in formula III:
referred to herein as “rameswaralide”. The diterpene molecule may be designed to be capable of traversing a biological membrane.
In one aspect, the invention features a pharmaceutical composition in unit dosage form suitable for the treatment of an inflammatory disorder. The composition consists essentially of about 40 mg to about 480 mg of the compound of formula I, II, or III (rameswaralide) or a derivative thereof. The unit dosage of the composition may be, for example, from about 175 mg to about 315 mg or from about 240 mg to about 280 mg. The composition is useful for the treatment of a wide variety of inflammatory disorders, including, for example, arthritis, psoriasis, and inflammatory bowel disease.
The invention also features an article of manufacture including packaging material and a pharmaceutical agent contained therein that is therapeutically effective for inhibiting an inflammatory disorder in a mammal. The packaging material may include a label that indicates that the pharmaceutical agent can be used for suppressing an inflammatory disorder in a mammal. The pharmaceutical agent includes rameswaralide or a derivative thereof.
In another embodiment, the present invention provides a method of obtaining the compound of formula I, II, or III. The method includes extracting the compound from coral, such as a soft coral, for example, the soft coral
Sinularia dissecta.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.
Other features and advantages of the invention will be apparent from the following detailed description, and from the claims.
REFERENCES:
patent: 4906794 (1990-03-01), Umezu et al.
patent: 5276217 (1994-01-01), Tius
Chan et al., “The Structure of Crotofolin A, a Diterpene with a New Skeleton”, J. Am. Chem. Soc. vol. 97, No. 15, pp. 4437-4439.*
P. Ramesh et al., “Rameswaralide, A Novel Diterpenoid from the Soft CoralSinularia dissecta” Tetrahedron Letters 39 (1998) 8217-8220.
Eisch, J.J., et al., The structure of Crotofolin A, a Diterpene with a New Skeleton, J. Am. Chem. Soc. vol. 97, No. 15 pp. 4437-4439.
Faulkner D. John
Raghavan K. V.
Venkateswarlu Y.
Yadav J. S.
Fish & Richardson P.C.
Indian Institute of Chemical Technology
Robinson Binta
Rotman Alan L.
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