Antiparasitic agents and process for their preparation

Details Antiparasitic agents and process for their preparation Antiparasitic agents and process for their preparation

C - Chemistry, Metallurgy

12

P

195/107, 167/180

C12P 19/62 (2006.01) A01N 43/90 (2006.01) A23K 1/17 (2006.01) A61K 31/365 (2006.01) C07D 493/20 (2006.01) C07H 17/08 (2006.01) C07H 19/01 (2006.01) C12P 17/18 (2006.01)

Patent

CA 1339480

The invention provides novel compounds having the formula: (see fig. I) wherein the broken line at the 22-23 position represents an optional double bond and wherein R1 is H or OH and the double bond is absent, or, the double bond is present and R1 is absent; R2 is an alpha-branched C3-C8 alkyl group, an alpha-branched C3-C8 alkenyl group, an alpha-branched C3-C8 alkoxy-alkyl group, an alpha-branched C3-C8 alkylthioalkyl group; a C5-C8 cycloalkylalkyl group wherein the alkyl group is an alpha-branched C2-C5 alkyl group; a C3-C8 cycloalkyl or C5-C8 cycloalkenyl group, either of which may optionally be substituted by methylene or one or more C1-C4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be saturated, or fully or partially unsaturated and which may optionally be substituted by one or more C1-C4 alkyl groups or halo atoms; R3 is hydrogen or methyl; R4 is H or 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy, with the proviso that when R2 is alkyl it is not isopropyl or sec-butyl; and when R4 is H, R1 is OH, and the double bond is absent, R2 is not 2-buten-2-yl, 2-pentene-2-yl or 4-methyl-2-pentene-2-yl. The compounds are broad spectrum antiparasitic agents having utility as anthelmintics, ectoparasiticides, insecticides and acaricides. The invention also provides a process for producing the novel avermectin and milbemycin derivatives by adding a carboxylic acid or derivative thereof to a fermentation of an avermectin or milbemycin producing organism.

514661

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