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Patent US4873224A successfully refreshed from Google Patents.
US4873224A
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Avermectin derivatives
Assignee: Merck and Co Inc
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Filing: 1988-05-23
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Granted: 1989-10-10
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Expires: 2008-05-23
Abstract
Abstract There are disclosed novel avermectin compounds wherein the 4 sec or 4 min hydroxy group is oxidized to an oxo group and replaced with a semicarbazone, carbonyl- or sulfonyl- hydrazone, hydrazone, or oxime, and optionally reduced to the corresponding semicarbazide, carbonyl- or sulfonylhydrazide or hydrazine. The semicarbazones and hydrazones are prepared from the 4 sec or 4 min oxo compound using the corresponding semicarbazides or hydrazines. The compounds have utility as anti-parasitic agents and compositions for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests. Compositions for such uses are also disclosed.
Inventors
- 👤 Bruce O. Linn
- 👤 Helmut Mrozik
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:41
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01; A; A01; A01N; A01N43/00; A01N43/90; A01N47/00; A01N47/08; A01N47/28; A01N47/34; A61; A61P; A61P33/00; A61P33/10
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
151 words
A compound having the formula: ##STR36## wherein m is 0 or 1; R 1 is ##STR37## wherein n is 0 or 1; R is hydrogen, amino, loweralkyl, mono- or di-lower alkyl amino, methoxy-loweralkylamino, diloweralkylaminoloweralkyl, diloweralkylaminoloweralkylamino, loweralkylphenyl, loweralkyl phenylamino, loweralkoxyphenyl, loweralkoxyphenylamino, halophenyl, halophenylamino, sulfamylphenyl, sulfamyl-phenylamino, morpholinyl, N-loweralkyl piperazinyl, N-(loweralkoxy phenyl)piperazinyl, N-(halophenyl)piperazinyl, benzimidazolylamino, pyrimidinylamino, thiazolylamino, benzothiazolylamino or N-(loweralkylphenyl)piperzinyl R' is hydrogen or loweralkyl; X is carbonyl or sulfonyl; A is a double bond or an epoxide; B is a single bond or a double bond; R 2 is hydrogen or hydroxy, R 3 is iso-propyl or sec-butyl, R 4 is hydroxy or methoxy, R 5 and R 6 are present only when B is a single bond and are independently hydrogen, hydroxy or halogen; and the broken line indicates a single or a double bond at the 22,23-position, provided that R 2 is hydroxy only when the broken line indicates a single bond.
Claim 2
Dependent Claim
151 words
A compound having the formula: ##STR36## wherein m is 0 or 1; R 1 is ##STR37## wherein n is 0 or 1; R is hydrogen, amino, loweralkyl, mono- or di-lower alkyl amino, methoxy-loweralkylamino, diloweralkylaminoloweralkyl, diloweralkylaminoloweralkylamino, loweralkylphenyl, loweralkyl phenylamino, loweralkoxyphenyl, loweralkoxyphenylamino, halophenyl, halophenylamino, sulfamylphenyl, sulfamyl-phenylamino, morpholinyl, N-loweralkyl piperazinyl, N-(loweralkoxy phenyl)piperazinyl, N-(halophenyl)piperazinyl, benzimidazolylamino, pyrimidinylamino, thiazolylamino, benzothiazolylamino or N-(loweralkylphenyl)piperzinyl R' is hydrogen or loweralkyl; X is carbonyl or sulfonyl; A is a double bond or an epoxide; B is a single bond or a double bond; R 2 is hydrogen or hydroxy, R 3 is iso-propyl or sec-butyl, R 4 is hydroxy or methoxy, R 5 and R 6 are present only when B is a single bond and are independently hydrogen, hydroxy or halogen; and the broken line indicates a single or a double bond at the 22,23-position, provided that R 2 is hydroxy only when the broken line indicates a single bond.
Claim 3
Dependent Claim
125 words
The compound of claim 1 wherein R 1 is ##STR38## and R is, amino, loweralkyl, mono- or di-lower alkyl amino, methoxy-loweralkylamino, diloweralkylaminolo-weralkylamino, loweralkylphenyl, loweralkyl -phenylamino, halophenyl, halophenylamino, morpholinyl, N-loweralkyl piperazinyl, N-(loweralkoxyphenyl)-piperazinyl, N-(halophenyl)piperazinyl, or N-(loweralkyl phenyl) piperazinyl; or R 1 is --NH--NRR' and R is, loweralkyl, methoxyloweralkyl, diloweralkylamino loweralkyl, loweralkylphenyl, halophenyl, morpholinyl carbonyl, N-loweralkyl piperazinylcarbonyl, or N-(loweralkylphenyl)piperazinylcarbonyl; R 1 is a hydrogen or loweralkyl; A is a double bond B is a single bond or a double bond; R 2 is hydrogen R 3 is iso-propyl or sec-butyl, R 4 is hydroxy R 5 and R 6 are present only when B is a single bond and are independently hydrogen or fluorine. and the broken line indicates a single or a double bond at the 22,23-position.
Claim 4
Dependent Claim
88 words
The compound of claim 2 wherein m=1 R 1 is ##STR39## and R is, mono- or di-loweralkylamino, diloweralkylamino-, loweralkylamino, loweralkylphenyl, halophenyl, N-loweralkyl piperazinyl or N (loweralkylphenyl) piperazinyl; or R 1 is --NH--NRR' and R is loweralkyl, or N-(loweralkylphenyl)piperazinyl; R' is hydrogen or loweralkyl; A is a double bond B is a double bond; R 2 is hydrogen; R 3 is iso-propyl or sec-butyl, R 4 is hydroxy; R 5 and R 6 are hydrogen; and the broken line indicates a single or a double bond at the 22,23-position.
Claim 5
Dependent Claim
10 words
The compound of claim 3 which is 4"-Oxoavermectin B1a/B1b 4,4-dimethylsemicarbazone.
Claim 6
Dependent Claim
9 words
The compound of claim 2 which is 10,11-Dihydro-10-fluoro-4"-oxoavermectin B1a/B1b-semicarbazone.
Claim 7
Dependent Claim
10 words
The compound of claim 3 which is 4-"-Oxoavermectin B1a/B1b 2-[4-(4-chlorophenyl)piperazin-1-yl)carbonyl]hydrazone.
Claim 8
Dependent Claim
10 words
The compound of claim 3 which is 4"-Oxoavermectin B1a/B1b 2-{[4-(4-tolyl)piperazin-1-yl]carbonyl}hydrazone.
Claim 9
Dependent Claim
10 words
The compound of claim 3 which is 4"-epi-(2,2-Dimethylhydrazin-1-yl 4"-deoxyavermectin B1a/B1b.
Claim 10
Dependent Claim
10 words
The compound of claim 3 which is 22,23-Dihydro-4"-epi-(2,2-dimethylhydrazin-1-yl) 4"-deoxyavermectin B1a/B1b.
Claim 11
Dependent Claim
10 words
The compound of claim 1 which is 22,23-Dihydro-4'-epi-(2,2-dimethylhydrazin-1-yl)-4'-deoxyavermectin B1a/B1b monosaccharide.
Claim 12
Dependent Claim
26 words
A method for the treatment of parasitic infections which comprises administering to an animal infected with parasites an effective amount of a compound of claim 1.
Claim 13
Dependent Claim
34 words
A method for the treatment of parasitic infestations of agricultural crops which comprises treating such crops while they are growing or while in storage with an effective amount of a compound of claim 1.
Claim 14
Dependent Claim
29 words
A composition useful for treating animals infected with parasites or areas infested with parasites which comprises an inert carrier and an effective amount of a compound of claim 1.
References Cited (Backward Citations)
US4378353A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-10-09 | 1993-04-10 | 1993-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-10-09 | 1997-04-10 | 1997-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-10-09 | 2001-04-10 | 2001-10-10 | $7700.00 | Window Closed / Lapsed |