Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Reexamination Certificate
2000-07-19
2004-03-23
Celsa, Bennett (Department: 1627)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
C514S002600, C514S008100, C514S011400, C530S322000
Reexamination Certificate
active
06710029
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to dehydrodidemnin B and, in particular, to the isolation of dehydrodidemnin B, a cyclic depsipeptide, from a tunicate of the Ascidiacea class. This novel compound has been shown to have antiviral, antitumoral and cytotoxic activities.
BACKGROUND OF THE INVENTION
The didemnins form a class of cyclic depsipeptides which have been isolated from various species of the Trididemnum genus. They have been shown to have potent activity against viruses and tumor cells (Rinehart, Jr., et al.,
J. Am. Chem. Soc
., 103, 1857-59 (1981). Didemnin B, up to now the most active compound of this class, has been shown to have potent immunosuppressive activity (Montgomery et al.,
Transplantation
, 40, 49-56 (1985) and a more potent inhibition of binding of prolactin to human lymphocytes than other didemnin compounds (Montgomery. et al.,
Fed. Prac
., 44, 634 (1987).
SUMMARY OF THE INVENTION
This invention provides a novel and more active compound of this class, unexpectedly isolated from the Mediterranean tunicate
Alpidium albicans
, namely dehydrodidemnin B (or “DDB”), having the formula:
where R is hydrogen; and derivatives thereof with the same class of biological activity, i.e., where R is Acyl, Alkyl or Aryl.
REFERENCES:
patent: 4493796 (1985-01-01), Rinehart, Jr.
patent: 5294603 (1994-03-01), Rinehart
patent: 5834586 (1998-11-01), Rinehart et al.
K. L. Rinehart, Jr.,J. Am. Chem. Soc.,vol. 103, pp. 1857-1859 (1981).
Montgomery, D. W. Zukoski, C.F.Transplantation,vol. 40, pp. 49-56 (1985).
Montgomery et al.,Fed. Prac.,vol. 44, pp. 634 (1987).
Rinehart, Jr. et al.,Pure and Appl. Chem.,vol. 54, pp. 2409-2424 (1982).
Rinehart,Escom,“Didemnin and its Biological Properties”, pp. 626-631 (1987).
Rinehart et al.,J. Am. Chem. Soc.,vol. 109, pp. 6846-6848 (1987).
Lithgow-Bertelloni Anna M.
Rinehart Kenneth L.
Banner & Witcoff , Ltd.
Celsa Bennett
Linek Ernest V.
Pharma Mar S.A.
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