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US 4,906,619 AGranted
Alkyl avermectin derivatives
AssigneeMerck & Co., Inc.
InventorsPhilip Eskola, Thomas L. Shih, Helmut Mrozik
Life of this patent
Estimating the term…
Abstract
There are disclosed avermectin derivatives with a hydroxy and hydrocarbon substituents at the 5, 10, 13, 23, 4' and 4" positions which are prepared by the reaction of the 5, 10, 13, 23, 4' or 4" ketone compound with an organo-metallic Grignard reagent. The compounds are potent antiparasitic and anthelmintic agents in human and animal therapy and are potent pesticidical agents against agricultural pests. Compositions containing such compounds as the active agent are also disclosed.
Claims14
A compound having the formula:
- ##STR11## wherein A and B are independently single or double bonds;
- wherein R.sub.1 is hydroxy, R.sub.2 is loweralkyl, cycloloweralkyl, loweralkenyl or substituted loweralkyl;
- or when R.sub.1 is hydrogen, R.sub.2 is hydroxy or methoxy;
- when A is a double bond R.sub.4 is not present and R.sub.3 is hydrogen or loweralkyl;
- when A is a single bond R.sub.3 is hydroxy and R.sub.4 is loweralkyl, cycloloweralkyl, loweralkenyl or substituted loweralkyl;
- when R.sub.5 is hydroxy, R.sub.6 is loweralkyl, cycloloweralkyl, loweralkenyl or substituted loweralkyl;
- or when R.sub.5 is hydrogen R.sub.6 is hydrogen, halogen, hydroxy, ##STR12## when R.sub.7 is hydroxy and R.sub.8 is loweralkyl, cycloloweralkyl, loweralkenyl, cycloloweralkyl, or substituted loweralkyl;
- or when R.sub.7 is hydrogen, R.sub.8 is hydroxy, amino, loweralkylamino, diloweralkylamino, loweralkanoylamino, or loweralkenoyl (loweralkyl) amino;
- when B is a single bond, R.sub.9 is hydroxy and R.sub.10 is loweralkyl, cycloloweralkyl, loweralkenyl, or substituted loweralkyl;
- or R.sub.9 is hydrogen and R.sub.10 is hydrogen or hydroxy;
- when B is a double bond R.sub.1 is not present and R.sub.9 is hydrogen;
- and
- R.sub.11 is methyl, ethyl, isopropyl, sec. butyl, or C(CH.sub.3).dbd.C.HCH.sub.3, --C(CH.sub.3).dbd.C.HCH.sub.2 CH.sub.3 or --C(CH.sub.3).dbd.C.HCH(CH.sub.3).sub.2 ;
- provided that when R.sub.1, R.sub.5, R.sub.7 and R.sub.9 are all hydrogen and A is a double bond, R.sub.4 is not present and R.sub.3 is loweralkyl or provided that at the disubstituted positions 5, 10, 13, 23, 4 and 4" the combination is present whereby at least one of R.sub.1, R.sub.3, R.sub.5, R.sub.7, and R.sub.9 is hydroxy and the corresponding R.sub.2, R.sub.4, R.sub.6, R.sub.8, and R.sub.10 is loweralkyl, cycloloweralkyl, loweralkenyl or substituted loweralkyl and the substituent on the substituted lower alkyl groups are one or more of hydroxy, loweralkoxy or halogen.
11 more elements
Dependencies are inferred from the claim text.