EP0002615A2
Expired / Lapsed
EP
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13-Halo and 13-deoxy derivatives of modified milbemycin compounds and their preparation
Assignee: Merck and Co Inc
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Filing: 1978-12-15
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Granted: —
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Expires: 1998-12-15
Abstract
Abstract The invention provides novel compounds having the formula: where the broken line indicates a single or a double bond; R, is hydrogen or halogen; R 2 is hydrogen, methyl or loweralkanoyl; R 3 is n-propyl or sec-butyl; and R 4 is present only when the broken line indicates a single bond and represents hydrogen, hydroxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxy. These compounds are derivatives of C-076 compounds in which the 13-position is unsubstituted or halogen-substituted. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis, followed by halogenation and, if desired, by subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaricidal agents and their use as such also forms part of the invention.
Inventors
- 👤 John Clifford Chabala
- 👤 Michael Herbert Fisher
- 👤 Helmut Hugo Mrozik
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 12:13
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01; A; A01; A01N; A01N43/00; A01N43/90; A61; A61P; A61P33/00; A61P33/02; A61P33/10; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C12; C12N; C12N1/00; C12N1/20; C12N1/205; C12P; C12P19/00; C12P19/44; C12P19/60; C12P19/62; C12P19/623; C12R; C12R2001/00; C12R2001/01; C12R2001/465
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
59 words
A compound having the formula: where the broken line indicates a single or a double bond; R 1 is hydrogen or halogen; R 2 is hydrogen, methyl or loweralkanoyl; R 3 is n-propyl or sec-butyl; and R 4 is present only when the broken line indicates a single bond and represents hydrogen, hydroxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxy.
Claim 2
Dependent Claim
59 words
A compound having the formula: where the broken line indicates a single or a double bond; R 1 is hydrogen or halogen; R 2 is hydrogen, methyl or loweralkanoyl; R 3 is n-propyl or sec-butyl; and R 4 is present only when the broken line indicates a single bond and represents hydrogen, hydroxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxy.
Claim 3
Dependent Claim
10 words
The compound of Claim 1 wherein R 3 is n-propyl.
Claim 4
Dependent Claim
10 words
The compound of Claim 1 wherein R 3 is sec-butyl.
Claim 5
Dependent Claim
9 words
The compound of Claim 3 wherein R is hydrogen.
Claim 6
Dependent Claim
9 words
The compound of Claim 3 wherein R is chlorine.
Claim 7
Dependent Claim
17 words
The compound of Claim 3 wherein the broken line indicates'a single bond and R 4 is hydrogen.
Claim 8
Dependent Claim
11 words
The compound of Claim 3 wherein R 2 is a loweralkanoyl.
Claim 9
Dependent Claim
10 words
The compound of Claim 3 wherein R 4 is loweralkanoyloxy.
Claim 10
Dependent Claim
160 words
A process for the preparation of a compound having the formla : where the broken line indicates a single or a double bond; R 1 is hydrogen or halogen; R 2 is hydrogen, methyl or loweralkanoyl; R 3 is n-propyl or sec-butyl; and R 4 is present only when the broken line indicates a single bond and represents hydrogen, hydroxy, loweralkanoyloxy, loweralkylthio, loveralkylsulfinyl, loweralkylsulfonyl or loweralkoxy; which comprises treating a compound of the above structural formula in which R 1 is hydroxy and the other variables are as defined above with a benzenesulfonyl halide in the presence of a base to prepare the corresponding compound in which R 1 is a halogen and the other variables are as defined above, and optionally treating the compound in which R 1 is halogen with a trialkyltinhydride in the presence of a free radical initiator to prepare the compound in which R 1 is hydrogen and the other variables are as defined above.
Claim 11
Dependent Claim
160 words
A process for the preparation of a compound having the formla : where the broken line indicates a single or a double bond; R 1 is hydrogen or halogen; R 2 is hydrogen, methyl or loweralkanoyl; R 3 is n-propyl or sec-butyl; and R 4 is present only when the broken line indicates a single bond and represents hydrogen, hydroxy, loweralkanoyloxy, loweralkylthio, loveralkylsulfinyl, loweralkylsulfonyl or loweralkoxy; which comprises treating a compound of the above structural formula in which R 1 is hydroxy and the other variables are as defined above with a benzenesulfonyl halide in the presence of a base to prepare the corresponding compound in which R 1 is a halogen and the other variables are as defined above, and optionally treating the compound in which R 1 is halogen with a trialkyltinhydride in the presence of a free radical initiator to prepare the compound in which R 1 is hydrogen and the other variables are as defined above.
Claim 12
Dependent Claim
16 words
The use in the treatment of parasitic infections of a compound as claimed in Claim 1.
References Cited (Backward Citations)
No citation records indexed.
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