US4229441A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Immunologic adjuvant
Assignee: Merck and Co Inc
•
Filing: 1978-12-01
•
Granted: 1980-10-21
•
Expires: 1998-12-01
Abstract
Abstract Glycolipid compounds of the formulae ##STR1## wherein R is ##STR2## are useful immunologic adjuvants in vaccines.
Inventors
- 👤 Robert L. Bugianesi
- 👤 Mitree M. Ponpipom
- 👤 Tsung-Ying Shen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 04:17
CPC Classifications
A; A61; A61K; A61K39/00; A61K39/39; A61P; A61P37/00; A61P37/02; A61P37/04; C; C07; C07J; C07J31/00; C07J31/006; C07J41/00; C07J41/0033; C07J41/0055; A61K2039/555; A61K2039/55511; Y; Y02; Y02A; Y02A50/00; Y02A50/30
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
25 words
A compound selected from the group consisting of: 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-L-fucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-D-glucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2-acetamido-2-deoxy-1-thio-β-D-galactopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-D-xylopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-α-L-arabinopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-lactoside, and 2-S-[6-(5-cholesten-3β-yloxy)hexyl]-2-thio-β-D-N-acetylneuraminic acid.
Claim 2
Dependent Claim
25 words
A compound selected from the group consisting of: 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-L-fucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-D-glucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2-acetamido-2-deoxy-1-thio-β-D-galactopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-D-xylopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-α-L-arabinopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-lactoside, and 2-S-[6-(5-cholesten-3β-yloxy)hexyl]-2-thio-β-D-N-acetylneuraminic acid.
Claim 3
Dependent Claim
32 words
An intermediate for a compound of claim 1 selected from the group consisting of 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-galactopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside; 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside; 6-(5-cholesten-3β-yloxy)hexyl hepta-O-acetyl-1-thio-β-lactoside; 6-(5-cholesten-3β-yloxy)-hexane-1-thiol, and Methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-2-S-[6-(5-cholesten-3β-yloxy)hexyl]2-thio-D-neuraminate.
Claim 4
Dependent Claim
12 words
A composition comprising an antigenic material and a compound of claim 1.
Claim 5
Dependent Claim
20 words
A composition according to claim 3 wherein the compound is present in an amount effective to exert an adjuvant effect.
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) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |