US4301152A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Immunologic adjuvant
Assignee: Merck and Co Inc
•
Filing: 1979-10-26
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Granted: 1981-11-17
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Expires: 1999-10-26
Abstract
Abstract Immunologic adjuvants are obtained by the synthesis of 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside and its 6-deoxy-6-oleamido derivative.
Inventors
- 👤 Mitree M. Ponpipom
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 12:50
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/14; C07H19/00; C07H19/02; C07H19/04; C07H19/044; C07J; C07J41/00; C07J41/0033; C07J41/0055; C07J41/0088; C07J43/00; C07J43/003
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
21 words
An intermediate in the preparation of 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside selected from the group consisting of 1,2,3,4-tetra-O-acetyl-6-deoxy-6-phthalimido-D-galactopyranose; 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-α-D-galactopyranosyl bromide; 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranose; or 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranoside.
Claim 2
Dependent Claim
21 words
An intermediate in the preparation of 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside selected from the group consisting of 1,2,3,4-tetra-O-acetyl-6-deoxy-6-phthalimido-D-galactopyranose; 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-α-D-galactopyranosyl bromide; 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranose; or 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranoside.
Claim 3
Dependent Claim
9 words
A compound of claim 1 having the name 1,2,3,4-tetra-O-acetyl-6-deoxy-6-phthalimido-D-galactopyranose.
Claim 4
Dependent Claim
10 words
A compound of claim 1 having the name 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-α-D-galactopyranosyl bromide.
Claim 5
Dependent Claim
9 words
A compound of claim 1 having the name 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranose.
Claim 6
Dependent Claim
10 words
A compound of claim 1 having the name 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranoside.
Claim 7
Dependent Claim
15 words
An immunologic adjuvant compound selected from 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside and the corresponding oleic acid amide thereof.
Claim 8
Dependent Claim
15 words
An immunologic adjuvant compound selected from 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside and the corresponding oleic acid amide thereof.
Claim 9
Dependent Claim
11 words
A compound according to claim 6 having the name 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside.
Claim 10
Dependent Claim
11 words
A compound according to claim 6 having the name 6-(5-cholesten-3β-yloxy)hexyl 6-deoxy-6-oleamido-1-thio-β-D-galactopyranoside.
Claim 11
Dependent Claim
22 words
A composition comprising a compound of claim 6 in an amount effective to exert an adjuvant effect and a pharmaceutically acceptable carrier.
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) | 1984-11-16 | 1985-05-18 | 1985-11-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-16 | 1989-05-18 | 1989-11-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-16 | 1993-05-18 | 1993-11-17 | $7700.00 | Window Closed / Lapsed |