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US4201861A
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Acyl derivatives of C-076 compounds
Assignee: Merck and Co Inc
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Filing: 1978-04-17
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Granted: 1980-05-06
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Expires: 1998-04-17
Abstract
Abstract Derivatives of C-076, a series of macrolides, are described in which the substituents are acyl groups. The acyl substituents may be aromatic of non-aromatic. The acyl derivatives are prepared by various procedures depending upon the particular C-076 compound being substituted. The compounds thus produced have profound anthelmintic, insecticidal, ectoparasiticidal and acaracidal activity and compositions for such uses are also disclosed.
Inventors
- 👤 Helmut H. Mrozik
- 👤 Michael H. Fisher
- 👤 Peter Kulsa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 02:43
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/22; A; A01; A01N; A01N43/00; A01N43/90; C07H; C07H17/00; C07H17/04; C07H17/08; C12; C12P; C12P17/00; C12P17/18; C12P17/181; C12P19/00; C12P19/44; C12P19/60; C12P19/62; C12P19/623
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
152 words
A compound having the formula: ##STR5## wherein the broken line indicates a single or a double bond; R 1 is hydroxy or acyloxy 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 acyl; and R is hydrogen, acyl, α-L-oleandrosyl, 4'-acyl-α-L-oleandrosyl, 4'-(α-L-oleandrosyl)-α-L-oleandrosyl, 4"-acyl-4'-(α-L-oleandrosyl)-α-L-oleandrosyl; provided that at least one of the R, R 1 or R 3 groups contains an acyl group, and further that said acyl and the acyl portion of said acyloxy group is selected from loweralkanoyl; substituted loweralkanoyl wherein the substituents are halogen, carboxy, loweralkoxycarbonyl, amino, mono- or di-loweralkylamino, or loweralkanoylamino; unsaturated loweralkanoyl, loweralkoxycarbonyl, halogenated loweralkoxycarbonyl, benzoyl, or substituted benzoyl in which the substituents are halogen, nitro, alkyl, amino, hydroxy or alkoxy; carbamoyl, and N-substituted and N,N-disubstituted carbamoyl wherein the substitution is loweralkyl, benzyl, hydroxyloweralkyl or the carbamoyl nitrogen may be incorporated into a morpholine heterocycle.
Claim 2
Dependent Claim
152 words
A compound having the formula: ##STR5## wherein the broken line indicates a single or a double bond; R 1 is hydroxy or acyloxy 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 acyl; and R is hydrogen, acyl, α-L-oleandrosyl, 4'-acyl-α-L-oleandrosyl, 4'-(α-L-oleandrosyl)-α-L-oleandrosyl, 4"-acyl-4'-(α-L-oleandrosyl)-α-L-oleandrosyl; provided that at least one of the R, R 1 or R 3 groups contains an acyl group, and further that said acyl and the acyl portion of said acyloxy group is selected from loweralkanoyl; substituted loweralkanoyl wherein the substituents are halogen, carboxy, loweralkoxycarbonyl, amino, mono- or di-loweralkylamino, or loweralkanoylamino; unsaturated loweralkanoyl, loweralkoxycarbonyl, halogenated loweralkoxycarbonyl, benzoyl, or substituted benzoyl in which the substituents are halogen, nitro, alkyl, amino, hydroxy or alkoxy; carbamoyl, and N-substituted and N,N-disubstituted carbamoyl wherein the substitution is loweralkyl, benzyl, hydroxyloweralkyl or the carbamoyl nitrogen may be incorporated into a morpholine heterocycle.
Claim 3
Dependent Claim
11 words
The compound of claim 1 in which R 2 is iso-propyl.
Claim 4
Dependent Claim
11 words
The compound of claim 1 in which R 2 is sec-butyl.
Claim 5
Dependent Claim
12 words
The compound of claim 3 in which the acyl substituent is loweralkanoyl.
Claim 6
Dependent Claim
14 words
The compound of claim 4 in which the loweralkanoyl group is acetyl or propionyl.
Claim 7
Dependent Claim
17 words
The compound of claim 5 in which the acetyl or propionyl group is at the 4" position.
Claim 8
Dependent Claim
19 words
The compound of claim 5 in which the acetyl or propionyl group is at the 4" and 23 positions.
Claim 9
Dependent Claim
19 words
The compound of claim 5 in which the acetyl or propionyl group is at the 4" and 5 positions.
Claim 10
Dependent Claim
31 words
The compound of claim 6 which is C-076 A1a 4"-O-acetate wherein R is 4"-O-acetate-4'-(α-L-oleandrosyl)-α-L-oleandrosyl; R 1 is a 22,23 double bond; R 2 is sec butyl; and R 3 is methoxy.
Claim 11
Dependent Claim
28 words
The compound of claim 6 which is C-076 A2a 4"-O-acetae wherein R is 4"-O-acetate-4'-(α-L-oleandrosyl)-α-L-oleandrosyl; R 1 is hydroxy; R 2 is sec butyl; and R 3 is methoxy.
Claim 12
Dependent Claim
32 words
The compound of claim 6 which is C-076 B1a 4"-O-acetate wherein R is 4"-O-acetate 4'-(α-L-oleandrosyl)-α-L-oleanrosyl; R 1 is a 22,23 double bond; R 2 is sec butyl; and R 3 is hydroxy.
Claim 13
Dependent Claim
29 words
The compound of claim 6 which is C-076 B2a 4"-O-acetate wherein R is 4"-O-acetate 4'-(α-L-oleandrosyl)-α-L-oleandrosyl; R 1 is hydroxy; R 2 is sec butyl; and R 3 is hydroxy.
Claim 14
Dependent Claim
30 words
The compound of claim 7 which is C-076 A2a 4",23, di-O-acetate wherein R is 4"-O-acetate 4'-(α-L-oleandrosyl)-α-L-oleandrosyl; R 1 is acetoxy; R 2 is sec butyl; and R 3 is methoxy.
Claim 15
Dependent Claim
31 words
The compound of claim 8 which is C-076 B1a 4",5-di-O-acetate wherein R is 4"-O-acetate-4'-(α-L-oleandrosyl)-α-L-oleandrosyl; R 1 is a 22,23 double bond, R 2 is sec butyl; and R 3 is acetoxy.
Claim 16
Dependent Claim
28 words
The compound of claim 8 which is C-076 B2a 4",5-di-O-acetate wherein R is 4"-O-acetate-4'-(α-L-oleandrosyl)-α-L-oleandrosyl; R 1 is hydroxy; R 2 is sec butyl and R 3 is acetoxy.
Claim 17
Dependent Claim
31 words
The compound of claim 8 which is C-076 B1a-5-O-acetate wherein R is 4'-(α-L-oleandrosyl)-α-L-oleandrosyl; R 1 is a 22,23 double bond; R 2 is sec butyl; R and R 3 is acetoxy.
References Cited (Backward Citations)
US3950360A
Cited
US4093629A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-05-06 | 1983-11-05 | 1984-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-05-06 | 1987-11-05 | 1988-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-05-06 | 1991-11-05 | 1992-05-06 | $7700.00 | Window Closed / Lapsed |