US 5,350,742 AGranted

Avermectin difluoro derivatives

AssigneeMerck & Co., Inc.

InventorsPeter T. Meinke, Helmut Mrozik, Michael H. Fisher

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Abstract

Avermectin derivatives are disclosed which incorporate two fluorine atoms at the 4' monosaccharide position, the 4" disaccharide position or the 23 position. Avermectin aglycone derivatives are also disclosed which incorporate two fluorine atoms at position 13 or 23. These difluoro avermectin analogs are derived from corresponding ketones and enones which in turn are prepared by chemical modification of naturally occurring avermectins. These compounds are used as antiparisitic, insecticidal and antihelmintic agents in humans and animals and compositions containing such compounds as the active ingredient thereof are also disclosed.

Claims7

Dependent claims

A compound having the formula:

##STR7## Wherein:
Y is:
--CF.sub.2 --;
R.sup.1 is:
(a) --H, or
(b) --CH.sub.3 ;
R.sup.2 is:
(a) --H,
(b) --C.sub.1 -C.sub.8 alkyl,
(c) --C.sub.3 -C.sub.8 cycloalkyl,
(d) --C.sub.2 -C.sub.8 alkenyl,
(e) --C.sub.3 -C.sub.8 cycloalkenyl, or
(f) --aryl;
Z is:
(a) --CH(OH)--,
(b) --CO--
(c) --CH(OCH.sub.3)--
(d) --C(.dbd.NOH)--, or
(e) --C(.dbd.NOCH.sub.3)--;
R.sup.3 is:
(a) --H,
(b) --(C.sub.1 -C.sub.8 alkoxy).sub.n wherein n=1, 2, or 3;
##STR8## Wherein:
A is:
(a) --CF.sub.2 --,
(b) --CH(OH)--,
(c) --CHNR.sup.5 R.sup.5A --, or
(d) --CHSR.sup.6 --;
R.sup.5 and R.sup.5A are independently;
(a) H,
(b) C.sub.1 -C.sub.8 alkyl
(c) C.sub.1 -C.sub.6 alkenyl, or
(d) C.sub.1 -C.sub.6 alkanoyl;
R.sup.6 is:
(a) C.sub.1 -C.sub.3 alkoxyaminoalkyl, or
(b) C.sub.1 -C.sub.3 alkylNR.sup.5 R.sup.5A ;
R.sup.4 is:
(a) --H, or
(b) --F;
X is:
(a) --CH.sub.2 --,
(b) .dbd.CH--(10, 11 double bond),
(c) --CH(OH)--, or
(d) --CHF--.

41 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/074,763Filed 10 Jun 1993 · division
Priority: 29 Apr 1992
Granted: 27 Sep 1994
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07H 19/01
Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides ; Anhydro-derivatives…
A01N 43/90
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having two or more relevant hetero rings,…
A61P 33/00
Antiparasitic agents
A61P 33/10
Antiparasitic agents: anthelmintics

Family

Serial875,486Parent of this division · filed 29 Apr 1992
US 5,229,416 AParent of this division
US 5,350,742 AThis patent

From the US filing history. Foreign family members aren’t listed.

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