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EP0136892A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Avermectin epoxide derivatives

Assignee: Merck and Co Inc
•
Filing: 1984-09-28
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Granted: —
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Expires: 2004-09-28
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Abstract

Abstract Novel avermectin epoxides have the formula: in which the broken line at the 22,23-position indicates a single or a double bond; R, is hydrogen or hydroxy and is present only when the broken line at the 22,23-position indicates a single bond; R 1 is iso-propyl or sec-butyl; R 3 is hydroxy or methoxy; R 4 is hydroxy. a-L-oleandrosyloxy, or 4'-(a-L-oleandrosyl)-a-L-oleandrosyloxy; and the dotted triangular figures at the 8,9 and 14,15 positions indicate a double bond or an epoxide, provided that at least one of the 8,9 and 14,15 positions is epoxidized. The epoxides are prepared by oxidizing an avermectin compound with a mild oxidizing agent. The avermectin epoxide compounds have utility as anti-parasitic agents and can be made into compositions suitable for that use. The compounds are also highly potent insecticides against agricultural pests.

Inventors

  • 👤 Helmut H. Mrozik

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-05 18:51
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01; A; A01; A01N; A01N43/00; A01N43/90; A23; A23K; A23K20/00; A23K20/10; A23K20/195; A61; A61P; A61P33/00; A61P33/10

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 90 words
A compound having the formula: in which the broken line at the 22,23-position indicates a single or a double bond; R is hydrogen or hydroxy and is present only when the broken line at the 22,23-position indicates a single bond; R 2 is iso-propyl or sec-butyl; R 3 is hydroxy or methoxy; R 4 is hydroxy, a-L-oleandrosyloxy, or 4'-(a-L-oleandrosyl)-a-L-oleandrosyloxy; and the dotted triangular figures at the 8,9 and 14,15 positions indicate a double bond or an epoxide, provided that at least one of the 8,9 and 14,15 positions is epoxidized.
Claim 2
Dependent Claim 90 words
A compound having the formula: in which the broken line at the 22,23-position indicates a single or a double bond; R is hydrogen or hydroxy and is present only when the broken line at the 22,23-position indicates a single bond; R 2 is iso-propyl or sec-butyl; R 3 is hydroxy or methoxy; R 4 is hydroxy, a-L-oleandrosyloxy, or 4'-(a-L-oleandrosyl)-a-L-oleandrosyloxy; and the dotted triangular figures at the 8,9 and 14,15 positions indicate a double bond or an epoxide, provided that at least one of the 8,9 and 14,15 positions is epoxidized.
Claim 3
Dependent Claim 25 words
A compound as claimed in Claim 1 in which the triangular figure at 8,9 is an epoxide and that at 14,15 is a double bond.
Claim 4
Dependent Claim 4 words
22,23-Dihydroavermectin (Bla and/or Blb)-8,9-epoxide.
Claim 5
Dependent Claim 4 words
22,23-Dihydroavermectin (Bla and/or Blb)-8,9-epoxide.
Claim 6
Dependent Claim 25 words
A compound as claimed in Claim 1 in which the triangular figure at 8,9 is a double bond and that at 14,15 is an epoxide.
Claim 7
Dependent Claim 4 words
22,23-Dihydroavermectin (Bla and/or Blb)-14,15-epoxide.
Claim 8
Dependent Claim 4 words
22,23-Dihydroavermectin (Bla and/or Blb)-14,15-epoxide.
Claim 9
Dependent Claim 14 words
A compound as claimed in Claim l In which both triangular figures represent epoxides.
Claim 10
Dependent Claim 43 words
A method of preparing a compound as claimed in Claim 1 that comprises treating a compound having the formula set forth in Claim 1, except that both of the triangular figures at 8,9 and 14,15 represent double bonds, with a mild oxidizing agent.
Claim 11
Dependent Claim 25 words
A method as claimed In Claim 7 in which the mild oxidizing agent is m-chloroperbenzoic acid or an alkyl hydroperoxide catalysed with vanadyl acetyl acetonate.
Claim 12
Dependent Claim 22 words
A compound as claimed in any one of Claims 1 to 6 for use in the treatment of parasitic infections in animals.
Claim 13
Dependent Claim 25 words
A composition useful for treating animals infected with parasites comprising an inert carrier and a compound as claimed in any one of Claims 1,to 6.

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