US4289760A
Expired / Lapsed
US
⏱️ 0.0 years remaining
23-Keto derivatives of C-076 compounds
Assignee: Merck and Co Inc
•
Filing: 1980-05-02
•
Granted: 1981-09-15
•
Expires: 2000-05-02
Abstract
Abstract Derivatives of C-076 compounds are described in which the C-076 molecule, a series of macrolides, has the 23-hydroxy group thereof oxidized to the 23-keto group. The 23-keto compounds are prepared by selectively oxidizing the suitably protected 23-hydroxy compound using such oxidizing agents as pyridinium dichromate, chromic acid-dimethyl pyrazole, chromic acid, chromic acid-acetic acid, and the like. Alternatively, selective oxidation of the unprotected 23-hydroxy compound may be accomplished by placing the compound in soil. Further reaction of the oxidized C-076 compounds is also possible. The compounds thus produced have profound anthelmintic, insecticidal, ectoparasiticidal, and acaricidal activity. Compositions containing the described C-076 derivatives as the active ingredient thereof are also disclosed.
Inventors
- 👤 Helmut H. Mrozik
- 👤 John G. MacConnell
- 👤 August J. Kempf
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 08:53
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: 7
Claim 1
Independent Claim
76 words
A compound having the formula: ##STR4## wherein R 1 is iso-propyl or sec-butyl; R 2 is methoxy, hydroxy, lower alkanoyloxy or substituted lower alkanoyloxy wherein the substituent is hydroxy, phenoxy or mono-, di- or tri-halo; and R 3 is hydrogen, α-L-oleandrosyl, 4'-(α-L-oleandrosyl)-α-L-oleandrosyl, 4"-lower alkanoyl-4'-(α-L-oleandrosyl)-α-L-oleandrosyl, 4"-substituted lower alkanoyl)-4'-(α-L-oleandrosyl)-α-L-oleandrosyl wherein the substituent is hydroxy, carboxy, phenoxy or mono-, di- or tri-halo; and the 4"- and/or 5-trisubstituted silyloxyacetyl, acetyl, trifluoroacetyl, trichloroacetyl, chloroacetyl, hydroxyacetyl, carboxyacetyl, and phenoxyacetyl protected derivatives thereof.
Claim 2
Dependent Claim
76 words
A compound having the formula: ##STR4## wherein R 1 is iso-propyl or sec-butyl; R 2 is methoxy, hydroxy, lower alkanoyloxy or substituted lower alkanoyloxy wherein the substituent is hydroxy, phenoxy or mono-, di- or tri-halo; and R 3 is hydrogen, α-L-oleandrosyl, 4'-(α-L-oleandrosyl)-α-L-oleandrosyl, 4"-lower alkanoyl-4'-(α-L-oleandrosyl)-α-L-oleandrosyl, 4"-substituted lower alkanoyl)-4'-(α-L-oleandrosyl)-α-L-oleandrosyl wherein the substituent is hydroxy, carboxy, phenoxy or mono-, di- or tri-halo; and the 4"- and/or 5-trisubstituted silyloxyacetyl, acetyl, trifluoroacetyl, trichloroacetyl, chloroacetyl, hydroxyacetyl, carboxyacetyl, and phenoxyacetyl protected derivatives thereof.
Claim 3
Dependent Claim
28 words
The compound of claim 1 wherein: R 1 is iso-propyl or sec-butyl; R 2 is methoxy, hydroxy or lower alkanoyloxy; and R 3 is 4'-(α-L-oleandrosyl)-α-L-oleandrosyl or 4"-lower alkanoyl-4'-(α-L-oleandrosyl)-α-L-oleandrosyl.
Claim 4
Dependent Claim
26 words
The compound of claim 2 wherein: R 1 is iso-propyl or sec-butyl; R 2 is methoxy, hydroxy or acetyl; and R 3 is 4'-(α-L-oleandrosyl)-α-L-oleandrosyl or 4"-acetyl-4'-(α-L-oleandrosyl)-α-L-oleandrosyl.
Claim 5
Dependent Claim
10 words
The compound of claim 3 which is 23-keto C-076 B2a.
Claim 6
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 7
Dependent Claim
26 words
A composition useful for the treatment of parasitic infections in animals which comprises an inert carrier and an effective amount of a compound of claim 1.
References Cited (Backward Citations)
ZA772345B
Cited
US4156720A
Cited
US4172940A
Cited
US4199569A
Cited
US4201861A
Cited
US4206205A
Cited
US4171314A
Cited
US4203976A
Cited
US4200581A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-14 | 1985-03-16 | 1985-09-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-14 | 1989-03-16 | 1989-09-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-14 | 1993-03-16 | 1993-09-15 | $7700.00 | Window Closed / Lapsed |