Avermectins and milbemycins to treat parasitic in dogs

Details Avermectins and milbemycins to treat parasitic in dogs Avermectins and milbemycins to treat parasitic in dogs

A - Human Necessities

01

N

A01N 43/90 (2006.01) A61K 31/35 (2006.01) A61K 31/365 (2006.01) A61K 31/71 (1990.01)

Patent

CA 2096345

Avermectins and milbemycins which are useful in the treatment of endo- and ectoparasitic infestations in dogs and have the general formula (I): Image wherein R1 is hydrogen, hydroxy or protected hydroxy; R2 is alkoxy, hydroxy or protected hydroxy, oxo, oximino or O-substituted oximino; R3 is hydrogen, hydroxy or protected hydroxy, or a group 4'-(.alpha.-L-oleandrosyl)-.alpha.-L-oleandrosyloxy, 4'-(.alpha.-L-oleandrosyl)-.alpha.-L-oleandrosyloxy, wherein the terminal hydroxy group is protected, .alpha.-L-oleandrosyloxy; or .alpha.-L-oleandrosyloxy wherein the terminal hydroxy group is protected; R4, R5, R6 and R7 are the same or different and each is hydrogen or an organic radical; and R8 is an amino, or imino group or a substituted amino or imino group with the proviso that: A) if R2 is hydroxy or protected hydroxy; R3 is hydrogen; R4 is hydrogen or methyl; R5 is hydrogen or methyl; and R8 is imino, oxyimino, O-substituted oxyimino, hydrazone, N-substituted hydrazone, semicarbazone, or N-substituted semicarbazone; then i) R1 is hydroxy or protected hydroxy; and further provided that (a) when R6 is hydrogen, R7 is not cis-C(CH3)=CHR n, where R n is selected from the group consisting of methyl, ethyl, and isopropyl; (b) when R7 is hydrogen, R6 is not cis-C (CH3) =CHR n, where R n is selected from the group consisting of methyl, ethyl, and isopropyl; (c) when R6 is hydrogen, R7 is not Image where R n is selected from the group consisting of methyl, ethyl, and isopropyl; (d) when R7 is hydrogen, R6 is not Image where R n is selected from the group consisting of methyl, ethyl, and isopropyl; B) if R2 is hydroxy or protected hydroxy; R3 is hydrogen; R4 is hydrogen or methyl; R5 is hydrogen or methyl; R6 is hydrogen, isopropyl, or sec-butyl; R7 is hydrogen, isopropyl, or sec-butyl; and R8 is imino, oxyimino, O-substituted oxyimino, hydrazone, or N-substituted hydrazone; then i) R1 is hydroxy or protected hydroxy; C) if R2 is oxo, hydroxy, substituted hydroxy having up to 25 carbon atoms; R3 is hydroxy; R4 is methyl; R5 is hydrogen; R6 is hydrogen; R7 is cis-C (CH3) =CHR°, where R° is selected from the group consisting of methyl, ethyl, and isopropyl; and R8 is -C=NOR p, where R P is selected from the group consisting of hydrogen and a C1-8 alkyl group: then i) R1 is hydroxy or protected hydroxy; said compound of forumula (I) being the E or Z isomer, or a mixture thereof.

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