US4156720A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Carbohydrate derivatives of milbemycin and processes therefor
Assignee: Merck and Co Inc
•
Filing: 1977-11-17
•
Granted: 1979-05-29
•
Expires: 1997-11-17
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
2026-11-03 23:44
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/12; C07D493/20; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
253 words
A compound having the formula: ##STR17## wherein R is hydrogen or a sugar moiety and R 1 , R 2 , R 3 and R' are defined as follows:R 1 R 2 R 3 R 4 R'______________________________________H H CH 3 CH 3 H or sugarH H CH 3 CH 3 CH 3 H H C 2 H 5 CH 3 H or sugarH H C 2 H 5 CH 3 CH 3 OH or sugar ##STR18## CH 3 CH 3 H or sugarOH or sugar ##STR19## CH 3 CH 3 CH 3 OH or sugar ##STR20## C 2 H 5 CH 3 H or sugarOH or sugar ##STR21## C 2 H 5 CH 3 CH 3 H H CH 3 ##STR22## H or sugarH H CH 3 ##STR23## H or sugar______________________________________ or ##STR24## wherein R is hydrogen or a sugar moiety and R 2 , R' and R" are defined as follows: ______________________________________
R.sub.2 R' R"
______________________________________
CH.sub.3 CH.sub.3 --OH or --O-sugar
C.sub.2 H.sub.5
CH.sub.3 --OH or --O-sugar
CH.sub.3 H or sugar H
______________________________________ provided that in the first of the above structural formulae at least one of R, R 1 and R' is a sugar moiety and in the second of the above structural formulae at least one of R, R', and R" is or contains a sugar moiety, wherein said sugar moiety 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, daunosaminosyl, mycaminosyl.
Claim 2
Dependent Claim
253 words
A compound having the formula: ##STR17## wherein R is hydrogen or a sugar moiety and R 1 , R 2 , R 3 and R' are defined as follows:R 1 R 2 R 3 R 4 R'______________________________________H H CH 3 CH 3 H or sugarH H CH 3 CH 3 CH 3 H H C 2 H 5 CH 3 H or sugarH H C 2 H 5 CH 3 CH 3 OH or sugar ##STR18## CH 3 CH 3 H or sugarOH or sugar ##STR19## CH 3 CH 3 CH 3 OH or sugar ##STR20## C 2 H 5 CH 3 H or sugarOH or sugar ##STR21## C 2 H 5 CH 3 CH 3 H H CH 3 ##STR22## H or sugarH H CH 3 ##STR23## H or sugar______________________________________ or ##STR24## wherein R is hydrogen or a sugar moiety and R 2 , R' and R" are defined as follows: ______________________________________
R.sub.2 R' R"
______________________________________
CH.sub.3 CH.sub.3 --OH or --O-sugar
C.sub.2 H.sub.5
CH.sub.3 --OH or --O-sugar
CH.sub.3 H or sugar H
______________________________________ provided that in the first of the above structural formulae at least one of R, R 1 and R' is a sugar moiety and in the second of the above structural formulae at least one of R, R', and R" is or contains a sugar moiety, wherein said sugar moiety 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, daunosaminosyl, 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 α 2 .
Claim 6
Dependent Claim
12 words
A compound of claim 3 which is 5-O-(β-D-glucopyranosyl) milbemycin α 1 .
Claim 7
Dependent Claim
10 words
The compound of claim 3 wherein the sugar is L-oleandrosyl-α-L-oleandrosyl.
Claim 8
Dependent Claim
12 words
A compound of claim 6 which is 13-(L-oleandrosyl-α-L-oleandrosyl) milbemycin α 1 .
Claim 9
Dependent Claim
12 words
A compound of claim 6 which is 5-O-(L-oleandrosyl-α-L-oleandrosyl) milbemycin α 1 .
Claim 10
Dependent Claim
12 words
A compound of claim 6 which is 13-(L-oleandrosyl-α-L-oleandrosyl) milbemycin α 2 .
Claim 11
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) | 1982-05-28 | 1982-11-27 | 1983-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-28 | 1986-11-27 | 1987-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-28 | 1990-11-27 | 1991-05-29 | $7700.00 | Window Closed / Lapsed |