Mono- and diepoxide derivatives of .DELTA.22-LL-F28249 compounds

Details Mono- and diepoxide derivatives of .DELTA.22-LL-F28249 compounds Mono- and diepoxide derivatives of .DELTA.22-LL-F28249 compounds

1987-03-06

1989-07-25

Hollrah, Glennon H.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

549264, 549214, 549215, A61K 3135

Patent

active

048514284

ABSTRACT:
The present invention relates to novel derivatives of LL-F28249 compounds wherein the 23-hydroxyl group is eliminated to form a double bond at the C(22,23)-position (.DELTA..sup.22), and the double bond at the C(26,27)-position is epoxidized concomitant with or without epoxidation of the double bond at the C(14,15)-position. These LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession number NRRL 15773. The compounds of the present invention are derived by regioselective epoxidation of 5,23-O,O-bissilylated LL-F28249 compounds at low temperature, desilylation, re-silylation of the 5-hydroxyl group, thiocarbonylation of the 23-hydroxyl group, desilylation and thermalization. The novel compounds of the invention have anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these described derivatives as active ingredients thereof are described herein.

REFERENCES:
Sutherland et al., "Preparation of Epoxymilbemycins as Pesticides and Antibacterial Agents", CA 108, 112076j (1988).

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