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US4200581A
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Alkyl derivatives of C-076 compounds
Assignee: Merck and Co Inc
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Filing: 1978-08-04
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Granted: 1980-04-29
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Expires: 1998-08-04
Abstract
Abstract Derivatives of C-076, a series of macrolides are described, in which the substituents are hydrocarbon groups. The hydrocarbon groups generally are alkyl groups which may be straight or branched and may optionally be substituted with phenyl. The substituted C-076 compounds are prepared by various procedures depending upon the position of the reaction site, and the particular C-076 compound being substituted. The compounds have profound anthelmintic, insecticidal, ectoparasiticidal and acaracidal activity and compositions for such uses are also disclosed.
Inventors
- 👤 Michael H. Fisher
- 👤 Aino Lusi
- 👤 Richard L. Tolman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 16:45
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/01; A; A61; A61P; A61P33/00; A61P33/10
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
187 words
A compound having the formula: ##STR6## wherein the broken line indicates a single or double bond; R 1 is hydroxy, loweralkanoyloxy or a hydrocarbonoxy and is present only when the broken line indicates a single bond; R 2 is iso-propyl or sec-butyl; R 3 is hydrogen, methyl, loweralkanoyl or a hydrocarbon; and R is hydrogen, loweralkanoyl, a hydrocarbon, or ##STR7## wherein R 4 is hydrogen, loweralkanoyl or a hydrocarbon; R 5 is hydrogen or methyl; and said hydrocarbonoxy group of R 1 is an alkoxy of from 1 to 10 carbon atoms or an alkoxy of from 1 to 10 carbon atoms substituted with phenyl and said hydrocarbon group in R, R 1 , and R 4 is an alkyl of from 1 to 10 carbon atoms or an alkyl of from 1 to 10 carbon atoms substituted by phenyl; and said hydrocarbon group in R 3 is an alkyl of from 1 to 10 carbon atoms substituted by phenyl provided that at least one of the R, R 1 , R 3 , or R 4 is or contains a hydrocarbon or R 5 is methyl.
Claim 2
Dependent Claim
187 words
A compound having the formula: ##STR6## wherein the broken line indicates a single or double bond; R 1 is hydroxy, loweralkanoyloxy or a hydrocarbonoxy and is present only when the broken line indicates a single bond; R 2 is iso-propyl or sec-butyl; R 3 is hydrogen, methyl, loweralkanoyl or a hydrocarbon; and R is hydrogen, loweralkanoyl, a hydrocarbon, or ##STR7## wherein R 4 is hydrogen, loweralkanoyl or a hydrocarbon; R 5 is hydrogen or methyl; and said hydrocarbonoxy group of R 1 is an alkoxy of from 1 to 10 carbon atoms or an alkoxy of from 1 to 10 carbon atoms substituted with phenyl and said hydrocarbon group in R, R 1 , and R 4 is an alkyl of from 1 to 10 carbon atoms or an alkyl of from 1 to 10 carbon atoms substituted by phenyl; and said hydrocarbon group in R 3 is an alkyl of from 1 to 10 carbon atoms substituted by phenyl provided that at least one of the R, R 1 , R 3 , or R 4 is or contains a hydrocarbon or R 5 is methyl.
Claim 3
Dependent Claim
70 words
A compounds of claim 1 wherein the broken line indicates a single or a double bond; R 1 is hydroxy or hydrocarbonoxy and is present only when the broken line indicates a single bond; R 2 is iso-propyl or sec-butyl; R 3 is hydrogen, methyl or a hydrocarbon; R is hydrogen, a hydrocarbon or ##STR8## wherein R 4 is hydrogen or a hydrocarbon; and R 5 is hydrogen or methyl.
Claim 4
Dependent Claim
31 words
A compound of claim 2 wherein the hydrocarbonoxy group of R 1 is methoxy or ethoxy, and the hydrocarbon group of R, R 3 and R 4 is methyl or ethyl.
Claim 5
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is iso-propyl.
Claim 6
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is sec-butyl.
Claim 7
Dependent Claim
21 words
The compound of claim 5 wherein R is hydrogen, methyl, ethyl or ##STR9## wherein R 4 is hydrogen, methyl or ethyl.
Claim 8
Dependent Claim
21 words
The compound of claim 6 wherein R is 5 hydrogen, methyl or said disaccharide wherein R 4 is hydrogen or methyl.
Claim 9
Dependent Claim
39 words
A compound of claim 7 wherein R is: ##STR10## R 1 and the broken line indicate a 22, 23 double bond, R 2 is sec-butyl, R 3 is hydrogen and R 5 is hydrogen which is 4"-O-methyl C-076 Bla.
Claim 10
Dependent Claim
40 words
The compound of claim 7 wherein R is methyl, R 1 and the broken line indicates a 22, 23 double bond, R 2 is sec-butyl, R 3 is hydrogen and R 5 is hydrogen which is 13-O-methyl C-076 B1a aglycone.
Claim 11
Dependent Claim
39 words
The compound of claim 7 wherein R is: ##STR11## R 1 and the broken line indicates a 22, 23 double bond, R 2 is sec-butyl, R 3 is acetyl and R 5 is hydrogen, which is 5-O-acetyl-4"-O-methyl C-076 B1a.
Claim 12
Dependent Claim
38 words
The compound of claim 7 wherein R is: ##STR12## R 1 is hydroxy, the broken line indicates a single bond, R 2 is sec-butyl, R 3 is methyl and R 5 is hydrogen which is 4"-O-methyl C-076 A2a.
Claim 13
Dependent Claim
38 words
The compound of claim 7 wherein R is: ##STR13## R 1 is methoxy, the broken line indicates a single bond, R 2 is sec-butyl, R 3 is methyl and R 5 is hydrogen which is 4",23-di-O-methyl C-076 A2a.
Claim 14
Dependent Claim
39 words
The compound of claim 7 wherein R is methyl, R 1 is hydroxy, the broken line indicates a single bond, R 2 is sec-butyl, R 3 is methyl, and R 5 is hydrogen which is 13-O-methyl C-076 A2a aglycone.
Claim 15
Dependent Claim
39 words
The compound of claim 7 wherein R is methyl, R 1 is methoxy, the broken line indicates a single bond, R 2 is sec-butyl, R 3 is methyl, and R 5 is hydrogen, which is 13,23-di-O-methyl C-076 A2a aglycone.
Claim 16
Dependent Claim
39 words
The compound of claim 7 wherein R is: ##STR14## R 1 and the broken line indicates a 22, 23 double bond, R 2 is sec-butyl, R 3 is methyl, and R 5 is hydrogen which is 4"-O-methyl C-076 A1a.
Claim 17
Dependent Claim
13 words
The compound of claim 5 wherein R 1 is 10 methoxy or ethoxy.
Claim 18
Dependent Claim
38 words
The compound of claim 16 wherein R is: ##STR15## R 1 is methoxy, the broken line indicates a single bond, R 2 is sec-butyl, R 3 is methyl and R 5 is hydrogen, which is 23-O-methyl C-076 A2a.
Claim 19
Dependent Claim
32 words
The compound of claim 16 wherein R is hydrogen, R 1 is methoxy, R 2 is sec-butyl, R 3 is methyl, and R 5 is hydrogen which is 23-O-methyl C-076 A2a aglycone.
Claim 20
Dependent Claim
13 words
The compound of claim 5 wherein said broken line indicates a double bond.
Claim 21
Dependent Claim
10 words
The compound of claim 5 wherein R 3 is ethyl.
Claim 22
Dependent Claim
38 words
The compound of claim 20 wherein R is ##STR16## R 1 is hydroxy, the broken line indicates a single bond, R 2 is sec-butyl, R 3 is ethyl and R 5 is hydrogen which is 5-O-ethyl C-076 B2a.
Claim 23
Dependent Claim
39 words
The compound of claim 20 wherein R is: ##STR17## R 1 and the broken line indicates a 22, 23 double bond, R 2 is sec-butyl, R 3 is ethyl and R 5 is hydrogen which is 5-O-ethyl C-076 B1a.
Claim 24
Dependent Claim
27 words
A method for the treatment of parasitic infections which comprises administering to a host infected with parasitic infections, an effective amount of a compound of claim 1.
Claim 25
Dependent Claim
20 words
A composition useful for the treatment of parasitic infections which comprises an inert carrier and a compound of claim 1.
References Cited (Backward Citations)
US3950360A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-29 | 1983-10-29 | 1984-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-29 | 1987-10-29 | 1988-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-29 | 1991-10-29 | 1992-04-29 | $7700.00 | Window Closed / Lapsed |