Patent US3724867A successfully refreshed from Google Patents.
US4094971A
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Immunological adjuvant agents active in aqueous solution
Assignee: Bpifrance Financement SA
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Filing: 1976-08-25
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Granted: 1978-06-13
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Expires: 1996-08-25
Abstract
Abstract Immunological adjuvants obtainable from already-known water-soluble adjuvants containing peptidoglycane fragments, which include saccharide units formed from N-acetylglucosamine and from an N-acyl-muramic acid wherein the acyl group is a glycolyl or acetyl group and to the muramyl group there are attached peptide chains, by modification of said already-known water-soluble adjuvants so that they bear acylating groups derived from physiologically-acceptable carboxylic polyacids, especially carboxylic diacids, and wherein preferably the acylating groups themselves include free carboxylic acid groups, for instance being derived from phthalic acid or succinic acid.
Inventors
- 👤 Louis A. Chedid
- 👤 Francoise Marguerite Audibert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:29
CPC Classifications
A; A61; A61K; A61K39/00; A61K39/39; C; C07; C07K; C07K14/00; C07K14/195; C07K14/355; A61K2039/555; A61K2039/55511; A61K2039/5555; A61K38/00
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
76 words
A compound, a water-soluble adjuvant which has immunological activity in-vivo when administered to a host in an oil-free aqueous solution, which adjuvant is an acylated peptidoglycane fragment having saccharide units of N-acetylglucosamine and N-acylmuramyl, the acyl radical being glycolyl or acetyl, and the muramyl group having peptide chains linked thereto, wherein the acyl groups of the peptidoglycane are of a physiologically acceptable polycarboxylic acid, or its anhydride, and the physiologically acceptable salts of the acylated compound.
Claim 2
Dependent Claim
76 words
A compound, a water-soluble adjuvant which has immunological activity in-vivo when administered to a host in an oil-free aqueous solution, which adjuvant is an acylated peptidoglycane fragment having saccharide units of N-acetylglucosamine and N-acylmuramyl, the acyl radical being glycolyl or acetyl, and the muramyl group having peptide chains linked thereto, wherein the acyl groups of the peptidoglycane are of a physiologically acceptable polycarboxylic acid, or its anhydride, and the physiologically acceptable salts of the acylated compound.
Claim 3
Dependent Claim
14 words
The immunological adjuvant according to claim 1, wherein the carboxylic polyacids are carboxylic diacids.
Claim 4
Dependent Claim
14 words
The immunological adjuvant according to claim 1 wherein the acyl group is a glycolyl.
Claim 5
Dependent Claim
17 words
The immunological adjuvant according to claim 1, wherein the acylating groups themselves include free carboxylic acid groups.
Claim 6
Dependent Claim
17 words
The immunological adjuvant according to claim 3, wherein the acylating groups themselves include free carboxylic acid groups.
Claim 7
Dependent Claim
19 words
The immunological adjuvant according to claim 1, wherein the acylating groups are derived from phthalic acid or its anhydride.
Claim 8
Dependent Claim
39 words
The immunological adjuvant according to claim 6, wherein the phthalyl groups are present in the modified adjuvant in a weight ratio lying within the range of from 50% to about 70% of the total weight of the modified adjuvant.
Claim 9
Dependent Claim
22 words
The immunological adjuvant according to claim 7, wherein the phthalyl groups are present in a weight ratio of the order of 67%.
Claim 10
Dependent Claim
16 words
The immunological adjuvant according to claim 1, wherein the acylating groups are derived from succinic acid.
Claim 11
Dependent Claim
39 words
The immunological adjuvant according to claim 9, wherein the succinyl groups are present in the modified adjuvant in a weight ratio lying within the range of from 30% to about 50% of the total weight of the modified adjuvant.
Claim 12
Dependent Claim
22 words
The immunological adjuvant according to claim 10, wherein the succinyl groups are present in a weight ratio of the order of 50%.
Claim 13
Dependent Claim
20 words
An immunological adjuvant composition comprising the immunological adjuvant according to claim 1 and a pharmacologically-acceptable solvent vehicle free from oil.
Claim 14
Dependent Claim
18 words
The immunological adjuvant composition according to claim 12 wherein the vehicle is an isotonic, sterile and injectable medium.
Claim 15
Dependent Claim
14 words
The immunological adjuvant composition according to claim 12 which comprises also a vaccinating antigen.
Claim 16
Dependent Claim
27 words
Process for preparing immunological adjuvants according to claim 1, wherein the acylating agent is selected from the group consisting of a physiologically-acceptable polycarboxylic acic and its anhydride.
Claim 17
Dependent Claim
27 words
The process according to claim 15 wherein the polycarboxylic acid or anhydride employed cause the introduction into said adjuvants of acylating groups containing free carboxylic acid groups.
Claim 18
Dependent Claim
26 words
The process according to claim 15, wherein the diacid used in selected from the group consisting of phthalic acid, phthalic anhydride, succinic acid and succinic anhydride.
Claim 19
Dependent Claim
33 words
The process according to claim 15, wherein the acylation is affected with the anhydride in an anhydrous basic solvent in which the immunological adjuvant containing peptidoglycane fragment used as starting material is soluble.
Claim 20
Dependent Claim
29 words
The process according to claim 18, wherein the basic solvent employed is one which when in contact with water will give a basic pH between 7 and about 10.
Claim 21
Dependent Claim
21 words
The process according to claim 18, wherein the acylation is carried out at a temperature at most equal to 50° C.
Claim 22
Dependent Claim
12 words
The process according to claim 18, wherein the solvent used is formamide.
Claim 23
Dependent Claim
12 words
The process according to claim 18, wherein the solvent used is pyridine.
Claim 24
Dependent Claim
16 words
The process according to claim 18, wherein one operates with an excess of the acylating agent.
Claim 25
Dependent Claim
12 words
The immunological adjuvant of claim 1 wherein the acyl group is acetyl.
Claim 26
Dependent Claim
21 words
The adjuvant of claim 1 wherein the peptidoglycan fragments contain neutral sugars selected from the group consisting of galactone and arabinose.
Claim 27
Dependent Claim
13 words
The adjuvant of claim 1 wherein the acyl group is phthalyl or succinyl.
Claim 28
Dependent Claim
15 words
The immunological adjuvant of claim 1 which is antigenically distinct from the corresponding unacylated compound.
Claim 29
Dependent Claim
18 words
The immunological adjuvant composition of claim 12 wherein the adjuvant is antigenically distinct from the corresponding unacylated compound.
Claim 30
Dependent Claim
20 words
The immunological adjuvant of claim 1 immunologically effective against an antigen and a serum containing antibodies effective against the antigen.
Claim 31
Dependent Claim
25 words
The method of promoting the immunization of a host which comprises administering to the host, a therapeutically effective amount of the composition of claim 12.
Claim 32
Dependent Claim
17 words
The method of claim 30 wherein the adjuvant composition is administered in an isotonic, sterile, injectable medium.
Claim 33
Dependent Claim
16 words
The method of claim 30 wherein the vaccine is administered in an isotonic, sterile, injectable medium.
Claim 34
Dependent Claim
16 words
The method of claim 30 wherein the serum is administered in an isotonic, sterile, injectable medium.
Claim 35
Dependent Claim
63 words
An immunological adjuvant which is a water-soluble compound which is a saccharide having N-acetyl-glucosamine group and an N-acetyl muramic acid group, wherein the acyl is glycolyl or acetyl and having a peptide chain linked to the muramyl radical, which compound is acylated, the cylating radical being selected from the group consisting of phthalyl or succinyl thereof, in an isotonic, sterile, injectable aqueous medium.
Claim 36
Dependent Claim
63 words
An immunological adjuvant which is a water-soluble compound which is a saccharide having N-acetyl-glucosamine group and an N-acetyl muramic acid group, wherein the acyl is glycolyl or acetyl and having a peptide chain linked to the muramyl radical, which compound is acylated, the cylating radical being selected from the group consisting of phthalyl or succinyl thereof, in an isotonic, sterile, injectable aqueous medium.
Claim 37
Dependent Claim
9 words
The metallic salt of the compounds of claim 34.
Claim 38
Dependent Claim
12 words
The salt of the compounds of claim 34 and an organic base.
Claim 39
Dependent Claim
91 words
A modified, water-soluble immunological adjuvant which is formed of break down fragments of cell-wall peptidoglycans containing saccharide units formed from N-acetyl glucosaminyl and N-acetylmuramyl groups, wherein the acyl groups is glycolyl or acetyl, and a peptide is linked to the muramyl group, which water-soluble immunological adjuvant carries modification-acylation groups fixed thereon and derived from physiologically-acceptable polycarboxylic acids of the type and in a proportion such as to enable said peptidoglycane break-down fragments to exert their adjuvant immunological activity in vivo when administered in the form of an oil-free, aqueous saline solution.
Claim 40
Dependent Claim
91 words
A modified, water-soluble immunological adjuvant which is formed of break down fragments of cell-wall peptidoglycans containing saccharide units formed from N-acetyl glucosaminyl and N-acetylmuramyl groups, wherein the acyl groups is glycolyl or acetyl, and a peptide is linked to the muramyl group, which water-soluble immunological adjuvant carries modification-acylation groups fixed thereon and derived from physiologically-acceptable polycarboxylic acids of the type and in a proportion such as to enable said peptidoglycane break-down fragments to exert their adjuvant immunological activity in vivo when administered in the form of an oil-free, aqueous saline solution.
Claim 41
Dependent Claim
21 words
The modified, water-soluble immunological adjuvant according to claim 37 wherein said peptidoglycan fragments also contain neutral sugar groups other than amino-sugars.
Claim 42
Dependent Claim
16 words
The modified, water-soluble immunological adjuvant according to claim 38 wherein said neutral sugar form arabino-galactane groups.
Claim 43
Dependent Claim
19 words
A modified, water-soluble immunological adjuvant according to claim 37 which is antigenically distinct from the non-modified water-soluble immunological adjuvant.
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) | 1981-06-12 | 1981-12-12 | 1982-06-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-12 | 1985-12-12 | 1986-06-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-12 | 1989-12-12 | 1990-06-13 | $7700.00 | Window Closed / Lapsed |