Cytotoxic alkaloid derivatives including Asmarine A and B...

Details Cytotoxic alkaloid derivatives including Asmarine A and B... Cytotoxic alkaloid derivatives including Asmarine A and B...

2001-06-22

2002-07-16

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C540S556000

Reexamination Certificate

active

06420357

ABSTRACT:

PRIORITY CLAIM
This application claims priority under 35 U.S.C. §119 of commonly owned PCT Application No. PCT/GB98/03884, filed Dec. 23, 1998. This application designated the United States and was published in the English language on Jul. 08, 1999 as WO 99/33832. The PCT application claims priority from British Patent Application No. GB 9727301.5, filed Dec. 23, 1997.
The present invention relates to new cytotoxic alkaloids, Asmarine A and B, isolated from the sponge Raspailia sp.
BACKGROUND OF THE INVENTION
Marine organisms, especially soft corals, sponges and tunicates, provide many secondary metabolites and exhibit a varying degree of biological activity (Reference 1). A family of these metabolites is the diterpene-alkaloid family; in 1984 (Reference 2) it was reported the structure of four Agelasines:
We have isolated from the sponge Raspailia sp. new cytotoxic diterpene-alkaloids related to this agelasine family.
SUMMARY OF THE INVENTION
The present invention provides new diterpene-alkaloid having either the formula (I) or the formula (II):
wherein R
1
represents hydrogen or lower alkyl or lower alkanoyl; R
2
represents hydrogen or lower alkyl; R
3
is either an alkyl or a cycloalkyl group containig one or more isoprene units, or a monoterpene or a sesquiterpene or a diterpene group; R
4
and R
5
represent hydrogen or lower alkyl; R
6
represents lower alkyl; X represents F or Cl or Br or I.
In the definitions of the groups in formulas (I) and (II), the lower alkyl and the lower alkyl moiety of the lower alkanoyl mean a straight-chain or branched alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl and hexyl.


REFERENCES:
patent: WO 92/00979 (1992-01-01), None
patent: WO 92/03438 (1992-03-01), None
Hungarian Patent Office Novelty Seach Report Dated Dec. 7, 2001.
Faulkner et al.,Natural Product Rep., (1997), pp. 253-302.
Yosief et al.,Tetrahedron Letters, “Asmarines A-C; Three novel cytotoxic metabolites from the marine sponge Raspailia sp.”, (1998), vol. 39, pp. 3323-3326.
Nakamura et al.,Tetrahedron Letters, “Agelasine-A, -B, -C And Novel Bicyclic Diterpenoids with A 9-Methyladeninium Unit Possessing Inhibitory Effects On Na, K-Atpase From The Okinawan Sea Sponge Agelas Sp”., (1984), vol. 25, pp. 2989-2992.
Bergeron et al.,Biochemical And Biophysical Research Communications, “Sntineopllastic And Antiherpetic Activity Of Spermidine Catecholamide Iron Chelators”, (1984), vol. 121, pp. 848-854.
Draetta, G. and Pagano, M. in “Annual Reports in Medicinal Chemistry, vol. 31”, 1996, Academic Press, San Diego, pp. 241-246.

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