ANTIPARASITIC AVERMECTIN DERIVATIVES

• Main Authors: DUTTON, CHRISTOPHER JAMES, GIBSON, STEPHEN PAUL, LEE, SHIH-JEN EDWARD
• Format: Patent
• Language: English; French
• Published: 27.07.1999
• Edition: 6
• Subjects: BEER; BIOCHEMISTRY; CHEMISTRY; DERIVATIVES THEREOF; ENZYMOLOGY; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; SPIRITS; SUGARS; VINEGAR; WINE

The invention provides broad spectrum antiparasitic compounds of the formula: (see formula I) . The broken line at the 22-23 position represents an optional double bond wherein either R1 is H or OH and the double bond is absent, or, the double bond is present and R1 is absent. R3 is hydrogen or methyl; and R4 is H or a 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy group of the formula: (see formula II) with the proviso that when R4 and R1 are both H and the double bond is absent, R2 is not H or CH3. Preferred values of R2 include methyl, isopropyl, sec-butyl, thiomethyl, thioethyl and 1-trifluoromethylethyl. formula SR5 wherein R5 is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C5-C8 cycloalkenyl, phenyl or substituted phenyl wherein the substituent is C1-C4 alkyl, C1-C4 alkoxy or halo, 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; end R4 is H or a 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy group of the formula: (see formula III) with the proviso that when R4 and R1 are both H and the double bond is absent, R2 is not H or CH3, are broad spectrum antiparasitic agents having utility as anthelmintics, ectoparasiticides, insecticides and acaricides.