Avermectin compounds with a 6,5-spiroketal ring system
AssigneeMerck & Co., Inc.
InventorPeter T. Meinke
Life of this patent
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Abstract
Avermectin analogs are disclosed wherein the 6,6-spiroketal ring system has been reduced in size to a 6,5-spiroketal ring system by the deletion of the 25-position carbon atom and the 25-alkyl substituent. This is accomplished by opening the outer spiroketal ring with the elimination of ring carbon atoms 23, 24 and 25 and the alkyl substituent at the 25-position and incorporation a new component, reclosing the spiroketal to a 5-membered ring with new substituents at the 24-position. The compounds are used as anti-parasitic insecticidal and anti-helmintic agents in humans and animals and compositions containing such compounds as the active ingredient thereof are also disclosed.
Claims14
The compounds having the following structural formula:
- ##STR9## where R is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl or phenyl;
- R.sub.1 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, C.sub.1 -C.sub.10 alkoxy-C.sub.1 -C.sub.10 alkyl or C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.10 alkyl group;
- a C.sub.3 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkenyl group, either of which may optionally be substituted by methylene or from 1 to 3 of C.sub.1 -C.sub.4 alkyl groups or halo atoms;
- phenyl, phenoxy, C.sub.1 -C.sub.10 alkyl phenyl, C.sub.2 -C.sub.10 alkenyl phenyl, C.sub.2 -C.sub.10 alkynyl phenyl, substituted C.sub.1 -C.sub.10 alkyl wherein the substituents independently are 1 to 3 of C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.8 cycloalkyl or substituted C.sub.1 -C.sub.10 alkyl wherein the substitutents are independently 1 to 3 of hydroxy, halogen, cyano, C.sub.1 -C.sub.5 alkyl thio, C.sub.1 -C.sub. 5 alkyl sulfinyl, C.sub.1 -C.sub.5 alkyl sulfonyl, amino, C.sub.1 -C.sub.5 mono or dialkyl amino, C.sub.1 -C.sub.5 alkanoyl amino or C.sub.1 -C.sub.5 alkanoylthio;
- R.sub.2 is hydroxy, C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 alkanoyloxy, oxo or oxime;
- R.sub.3 is hydrogen, hydroxy, C.sub.1 -C.sub.10 alkyloxy, C.sub.1 -C.sub.8 alkanoyloxy, C.sub.1 -C.sub.5 alkoxy-C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5
- alkoxy-C.sub.1 -C.sub.5 -alkoxy-C.sub.1 -C.sub.5 -alkoxy, halogen, ##STR10## wherein R.sub.4 is attached to C-4" or C-4' by a single bond and is hydroxy, amino, N-C.sub.1 -C.sub.8 alkylamino, N,N-C.sub.1 -C.sub.8 -dialkylamino, N-C.sub.1 -C.sub.8 alkanoylamino, N-C.sub.1 -C.sub.5 alkyl C.sub.1 -C.sub.5 alkanoylamino, tri C.sub.1 -C.sub.8 alkylsilyloxy, C.sub.1 -C.sub.8 alkylthio, C.sub.1 -C.sub.8 alkyl sulfinyl, C.sub.1 -C.sub.8 alkyl sulfonyl or substituted C.sub.1 -C.sub.8 alkyl thio, sulfinyl or sulfonyl where the substituents are from 1 to 5 of hydroxy, halogen, amino or mono or di-C.sub.1 -C.sub.3 alkylamino;
- or R.sub.4 is attached to C-4" or C-4' by a double bond and is ketone, oxime, semicarbazono, N-C.sub.1 -C.sub.8 alkylsemicarbazono, N,N-C.sub.1 -C.sub.8 diloweralkylsemicarbazono, C.sub.1 -C.sub.8 alkanoylhydrazono, benzoylhydrazono, or C.sub.1 -C.sub.8 alkylbenzoyl-hydrazono;
- and each R.sub.5 is independently hydroxy or C.sub.1 -C.sub.10 alkoxy.
Dependencies are inferred from the claim text.