4"-and 4'-alkylthio avermectin derivatives

Details 4"-and 4'-alkylthio avermectin derivatives 4"-and 4'-alkylthio avermectin derivatives

1991-03-28

1993-05-04

Ivy, C. Warren

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

514210, 514320, 514321, 514337, 514338, 514422, 514430, 514432, 514444, 514450, 548525, 548526, 548950, 548962, 546196, 546197, 546269, 546270, 549 13, 549 60, 549 88, 549 90, 536 71, A61K 3170, A61K 31365

Patent

active

052082229

ABSTRACT:
Avermectin derivatives are disclosed wherein the 4"-hydroxy group is replaced by a substituted alkylthio or acylthio group or an iodo group. These avermectin derivatives can be further derivatized at the 5- and 23-positions as ketoximes or O-substituted ketoximes. The 4"-substituted avermectin derivatives are prepared from the 4"- and 4'-trifluoromethanesulfonyl avermectin derivatives with halo- or sulfur-containing nucleophiles. The 4"- and 4'-.alpha.- and .beta.-trifluoromethane sulfonates are prepared selectively and converted into 4"- or 4'-alkyl- or acylsulfides, or iodides using the appropriate sulfur-containing or iodine nucleophile. Substituted sulfoxy and sulfonyl substituents at the 4"- and 4'-positions are prepared from oxidation of the corresponding substituted sulfides. The new compounds are potent anti-parasitic agents; in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.

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