US4259324A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Immunologic adjuvant thio glycoside compounds and compositions
Assignee: Merck and Co Inc
•
Filing: 1979-07-31
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Granted: 1981-03-31
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Expires: 1999-07-31
Abstract
Abstract Compounds of the formulae Y--R wherein Y is 1-thio-β-L-fucose, 1-thio-β-D-galactose or 1-thio-β-lactose and R is 2-(1-adamantyl)ethyl, 3-[(p-tetrafluorophenethyl)phenyl]propyl, 6-(5-cholesten-3β-yloxy)hex-3-ynl, oleyl, or hexadecyl are useful immunologic adjuvants in vaccines.
Inventors
- 👤 Mitree M. Ponpipom
- 👤 Tsung-Ying Shen
- 👤 Robert L. Bugianesi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 06:36
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/14; C07C; C07C17/00; C07C17/093; C07C29/00; C07C29/36; C07C29/38; C07C29/40; C07H15/18; C07J; C07J17/00; C07J17/005; C07J9/00
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
33 words
A compound of the formula ##STR1## wherein R is ##STR2## ##STR3## --CH 2 (CH 2 ) 7 --CH═CH--(CH 2 ) 7 CH 3 or --CH 2 (CH 2 ) 14 CH 3 .
Claim 2
Dependent Claim
33 words
A compound of the formula ##STR1## wherein R is ##STR2## ##STR3## --CH 2 (CH 2 ) 7 --CH═CH--(CH 2 ) 7 CH 3 or --CH 2 (CH 2 ) 14 CH 3 .
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein Y is 1-thio-β-L-fucose.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein Y is 1-thio-β-D-galactose.
Claim 5
Dependent Claim
9 words
A compound of claim 1 wherein Y is 1-thio-β-lactose.
Claim 6
Dependent Claim
38 words
A compound of claim 1 having the name 2-(1-adamantyl)ethyl 1-thio-β-L-fucopyranoside, 2-(1-adamantyl)ethyl 1-thio-β-D-galactopyranoside, 2-(1-adamantyl)ethyl 1-thio-β-lactoside, 3-[(p-tetrafluorophenethyl)phenyl]propyl 1-thio-β-L-fucopyranoside, 3-[(p-tetrafluorophenethyl)phenyl]propyl 1-thio-β-D-galactopyranoside, 3-[(p-tetrafluorophenethyl)phenyl]propyl 1-thio-β-lactoside, 6-(5-cholesten-3β-yloxy)hex-3-ynl 1-thio-β-L-fucopyranoside, 6-(5-cholesten-3β-yloxy)hex-3-ynl 1-thio-β-D-galactopyranoside, 6-(5-cholesten-3β-yloxy)hex-3-ynl 1-thio-β-lactoside, Oleyl 1-thio-β-L-fucopyranoside, Oleyl 1-thio-β-D-galactopyranoside, Oleyl 1-thio-β-lactoside, Hexadecyl 1-thio-β-L-fucopyranoside, Hexadecyl 1-thio-β-L-galactopyranoside, Hexadecyl 1-thio-β-lactoside.
Claim 7
Dependent Claim
6 words
A per-O-acetylated compound of claim 1.
Claim 8
Dependent Claim
23 words
An immunologic adjuvant composition comprising an antigenic material and a compound of claim 1 in an amount effective to exert an adjuvant effect.
Claim 9
Dependent Claim
24 words
An immunologic adjuvant composition comprising a compound of claim 1 in an amount effective to exert an adjuvant effect and a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
US4189471A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-03-30 | 1984-09-29 | 1985-03-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-03-30 | 1988-09-29 | 1989-03-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-03-30 | 1992-09-29 | 1993-03-31 | $7700.00 | Window Closed / Lapsed |