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US4134973A
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Carbohydrate derivatives of milbemycin and processes therefor
Assignee: Merck and Co Inc
•
Filing: 1977-04-11
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Granted: 1979-01-16
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Expires: 1997-04-11
Abstract
Abstract Carbohydrate derivatives of the antibiotic substance milbemycin, also identified as B-41, and of 13-hydroxy milbemycin are prepared. The carbohydrate groups are attached to the available hydroxy groups of milbemycin and to the hydroxy group synthesized at the 13-position. The reactions may be made selectively such that more than one carbohydrate group may be attached to a single position, or that multiple carbohydrate groups may be attached at different positions on the molecule. The described carbohydrate derivatives have antiparasitic activity.
Inventors
- 👤 Michael H. Fisher
- 👤 Richard L. Tolman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 18:38
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/12; C07D493/20; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
133 words
A compound having the formula: ##STR7## wherein R 1 ', R 2 and R 3 have the following definitions: ______________________________________
R'.sub.1 R.sub.2 R.sub.3
______________________________________
H or sugar CH.sub.3 CH.sub.3
H or sugar CH.sub.3 C.sub.2 H.sub.5
CH.sub.3 CH.sub.3 CH.sub.3
CH.sub.3 CH.sub.3 C.sub.2 H.sub.5
H or sugar
##STR8## CH.sub.3
H or sugar
##STR9## C.sub.2 H.sub.5
______________________________________ and independently, R 4 ' is hydrogen, hydroxy or a sugar connected to the substrate molecule through an oxygen atom; and R 5 is hydrogen or a sugar, provided at least one of R 1 ' , R 4 ' or R 5 is a sugar and wherein the sugar is a mono-, di- or trisaccharide selected from glucopyranosyl, galactopyranosyl, mannopyranosyl, maltosyl, arabinopyranosyl, lyxopyranosyl, xylopyranosyl, ribopyranosyl, oleandrosyl, rhamnopyranosyl, fucopyranosyl, lactosyl, ribofuranosyl, mannofuranosyl, glucofuranosyl, arabinofuranosyl, mycarosyl, cladinosyl, desosaminosyl, damnosaminosyl, mycaminosyl.
Claim 2
Dependent Claim
133 words
A compound having the formula: ##STR7## wherein R 1 ', R 2 and R 3 have the following definitions: ______________________________________
R'.sub.1 R.sub.2 R.sub.3
______________________________________
H or sugar CH.sub.3 CH.sub.3
H or sugar CH.sub.3 C.sub.2 H.sub.5
CH.sub.3 CH.sub.3 CH.sub.3
CH.sub.3 CH.sub.3 C.sub.2 H.sub.5
H or sugar
##STR8## CH.sub.3
H or sugar
##STR9## C.sub.2 H.sub.5
______________________________________ and independently, R 4 ' is hydrogen, hydroxy or a sugar connected to the substrate molecule through an oxygen atom; and R 5 is hydrogen or a sugar, provided at least one of R 1 ' , R 4 ' or R 5 is a sugar and wherein the sugar is a mono-, di- or trisaccharide selected from glucopyranosyl, galactopyranosyl, mannopyranosyl, maltosyl, arabinopyranosyl, lyxopyranosyl, xylopyranosyl, ribopyranosyl, oleandrosyl, rhamnopyranosyl, fucopyranosyl, lactosyl, ribofuranosyl, mannofuranosyl, glucofuranosyl, arabinofuranosyl, mycarosyl, cladinosyl, desosaminosyl, damnosaminosyl, mycaminosyl.
Claim 3
Dependent Claim
20 words
The compounds of claim 1 wherein the sugar is a mono or disaccharide selected from glucopyranosyl, rhamnopyranosyl, oleandrosyl and daunosaminosyl.
Claim 4
Dependent Claim
18 words
The compound of claim 2 wherein the sugar is a mono or disaccharide selected from glucopyranosyl and oleandrosyl.
Claim 5
Dependent Claim
12 words
A compound of claim 3 which is 13-(β-D-glucopyranosyloxy) milbemycin B 2 .
Claim 6
Dependent Claim
12 words
A compound of claim 3 which is 5-O-(β-D-glucopyranosyl) milbemycin A 3 .
Claim 7
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.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-15 | 1982-07-17 | 1983-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-15 | 1986-07-17 | 1987-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-15 | 1990-07-17 | 1991-01-16 | $7700.00 | Window Closed / Lapsed |