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US5057499A
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Avermectin derivatives
Assignee: Merck and Co Inc
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Filing: 1989-06-02
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Granted: 1991-10-15
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Expires: 2009-06-02
Abstract
Abstract There are disclosed novel avermectin derivatives wherein the outer oleandrose ring of avermectin or avermectin monosaccharide is homologated by addition of diazomethane to 4"- or 4'-oxo-avermectin to afford the perhydrooxepine derivatives. The homologated avermectins can then be further derivatized to afford additional novel avermectins. The new compounds are potent antiparasitic agents, in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.
Inventors
- 👤 Helmut Mrozik
- 👤 Peter J. Sinclair
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:30
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01; A; A01; A01N; A01N43/00; A01N43/90; A61; A61P; A61P33/00; A61P33/10
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
112 words
A compound having the formula ##STR12## wherein the broken line at the 22,23 position represents a single bond and wherein R 1 is hydrogen or hydroxy or oxo, or the broken line represents a double bond and R 1 is absent; R 2 is methyl, ethyl, or an alpha-branched C 3 -C 8 alkyl or alkenyl group; R 3 is hydrogen, loweralkyl or loweralkanoyl; R 4 is ##STR13## R 5 is ##STR14## R 6 is hydrogen or loweralkoxy; R 7 is hydroxy, amino, N-loweralkylamino, N,N-diloweralkylamino, or loweralkanoylamino; and R 8 is hydrogen; or R 7 and R 8 together are oxo, methylene, --CH 2 O--, hydroxyimino or semicarbazono; R 9 is loweralkyl.
Claim 2
Dependent Claim
112 words
A compound having the formula ##STR12## wherein the broken line at the 22,23 position represents a single bond and wherein R 1 is hydrogen or hydroxy or oxo, or the broken line represents a double bond and R 1 is absent; R 2 is methyl, ethyl, or an alpha-branched C 3 -C 8 alkyl or alkenyl group; R 3 is hydrogen, loweralkyl or loweralkanoyl; R 4 is ##STR13## R 5 is ##STR14## R 6 is hydrogen or loweralkoxy; R 7 is hydroxy, amino, N-loweralkylamino, N,N-diloweralkylamino, or loweralkanoylamino; and R 8 is hydrogen; or R 7 and R 8 together are oxo, methylene, --CH 2 O--, hydroxyimino or semicarbazono; R 9 is loweralkyl.
Claim 3
Dependent Claim
106 words
A compound of claim 1 wherein the broken line at the 22,23 position represents a single bond and wherein R 1 is hydrogen or hydroxy or oxo, or the broken line represents a double bond and R 1 is absent; R 2 is iso-propyl, sec-butyl, or an alpha-branched C 3 -C 8 alkenyl group; R 3 is hydrogen; R 4 is ##STR15## R 5 is ##STR16## R 6 is hydrogen or methoxy; R 7 is hydroxy, amino, N-loweralkylamino, N,N-diloweralkylamino, or loweralkanoylamino; and R 8 is hydrogen; or R 7 and R 8 together are oxo, methylene, --CH 2 O--, hydroxyimino or semicarbazono; R 9 is methyl.
Claim 4
Dependent Claim
106 words
A compound of claim 1 wherein the broken line at the 22,23 position represents a single bond and wherein R 1 is hydrogen or hydroxy or oxo, or the broken line represents a double bond and R 1 is absent; R 2 is iso-propyl, sec-butyl, or an alpha-branched C 3 -C 6 alkenyl group; R 3 is hydrogen; R 4 is ##STR17## R 5 is ##STR18## R 6 is hydrogen or methoxy; R 7 is hydroxy, amino, N-loweralkylamino, N,N-diloweralkylamino, or loweralkanoylamino; and R 8 is hydrogen; or R 7 and R 8 together are oxo, methylene, --CH 2 O--, hydroxyimino or semicarbazono; R 9 is methyl.
Claim 5
Dependent Claim
10 words
A compound of claim 1 which is 4'-O-[2-(4-methoxy-7-methyloxepin-5-onyl)]-avermectin B1a/B1b monosaccharide.
Claim 6
Dependent Claim
10 words
A compound of claim 1 which is 4'-O-[2-(5-exomethylene-4-methoxy-7-methyl-5,5a-oxo-oxepinyl)]-avermectin B1a/B1b monosaccharide.
Claim 7
Dependent Claim
15 words
A compound of claim 1 which is 4'-O-[2-(5-hydroxy-4-methoxy-7-methyl-oxepinyl)]-avermectin B1a/B1b monosaccharide isomer a or isomer b.
Claim 8
Dependent Claim
14 words
A compound of claim 1 which is 22,23-dihydro-4"-O-[2-(5-hydroxy-4-methoxy-7-methyl-oxepinyl)]-avermectin B1a/B1b monosaccharide isomer a or b.
Claim 9
Dependent Claim
10 words
A compound of claim 1 which is 4'-O-[2-(7-methyl-oxepin-5-onyl)]-avermectin B1a/B1b monosaccharide.
Claim 10
Dependent Claim
10 words
A compound of claim 1 which is 22,23-dihydro-4'-O-[2-(4-methoxy-7-methyl-oxepin-5-onyl)]-avermectin B1a/B1b monosaccharide.
Claim 11
Dependent Claim
10 words
A compound of claim 1 which is 4'-O-[2-(4-methoxy-7-methyloxepin-5-onyl)]-avermectin B2a/B2b monosaccharide.
Claim 12
Dependent Claim
10 words
A compound of claim 1 which is 4'-O-[2-(5-acetylamino-4-methoxy-7-methyl-oxepinyl)]-avermectin B1a/B1b monosaccharide.
Claim 13
Dependent Claim
28 words
A method for the treatment of parasitic diseases of animals which comprises administering to an animal infected with parasites an effective amount of a compound of claim 1.
Claim 14
Dependent Claim
28 words
A method for the treatment of parasitic diseases of plants which comprises administering to a plant infected with parasites an effective amount of a compound of claim 1.
Claim 15
Dependent Claim
28 words
A composition useful for the treatment of parasitic diseases of plants or animals which comprises an inert carrier and an effective amount of a compound of claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-10-14 | 1995-04-15 | 1995-10-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-10-14 | 1999-04-15 | 1999-10-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-10-14 | 2003-04-15 | 2003-10-15 | $7700.00 | Window Closed / Lapsed |