US4235771A
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US
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Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents
Assignee: Bpifrance Financement SA
•
Filing: 1978-05-15
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Granted: 1980-11-25
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Expires: 1998-05-15
Abstract
Abstract Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens, comprising an acyl-muramic acid group, wherein acyl means acetyl or glycolyl, and a short peptide chain linked to said acyl-muramic acid group, the first and second amino acids of said peptide chain being preferentially alanine and glutamic acid respectively.
Inventors
- 👤 Arlette Adam
- 👤 Francoise Audibert
- 👤 Louis Chedid
- 👤 Jean Choay
- 👤 Rita Ciorbaru
- 👤 Fabrielle Ellouz
- 👤 Dominique Juy
- 👤 Pierre LeFrancier
- 👤 Claude Merser
- 👤 Jean-Francois Petit
- 👤 Pierre Sinay
- 👤 Edgar Lederer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:59
CPC Classifications
A; A61; A61K; A61K39/00; A61K39/39; A61K35/00; A61K35/66; A61K35/74; C; C07; C07K; C07K9/00; C07K9/001; C07K9/005; A61K2039/555; A61K2039/55511; A61K2039/5555; A61K2039/55583; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/19; Y10S930/27
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
98 words
A peptidoglycan, N-Acmuramyl of the formula ##STR8## to which carboxyl group there is linked a peptide chain which comprises two to eight aminoacid residues, the first aminoacid residues comprising alanyl, seryl, or glycyl, and the second aminoacid residues comprising glutamic or aspartic acid residues, the carboxyls of this second aminoacid residue being either free or substituted, or when there are more than two aminoacid residues, the carboxyls of the second aminoacid being either free, substituted or linked to another aminoacid residue, with the proviso that both carboxyls of the second aminoacid are not free and Ac methyl, concurrently.
Claim 2
Dependent Claim
98 words
A peptidoglycan, N-Acmuramyl of the formula ##STR8## to which carboxyl group there is linked a peptide chain which comprises two to eight aminoacid residues, the first aminoacid residues comprising alanyl, seryl, or glycyl, and the second aminoacid residues comprising glutamic or aspartic acid residues, the carboxyls of this second aminoacid residue being either free or substituted, or when there are more than two aminoacid residues, the carboxyls of the second aminoacid being either free, substituted or linked to another aminoacid residue, with the proviso that both carboxyls of the second aminoacid are not free and Ac methyl, concurrently.
Claim 3
Dependent Claim
1 words
N-acetylmuramyl-L-alanyl-D-alpha-isoglutamine.
Claim 4
Dependent Claim
1 words
N-acetylmuramyl-L-alanyl-D-alpha-isoglutamine.
Claim 5
Dependent Claim
14 words
The Acmuramyl of chain 1 wherein the peptide chain comprises 2 to 5 aminoacids.
Claim 6
Dependent Claim
14 words
The Acmuramyl of chain 1 wherein the peptide chain comprises 2 to 5 aminoacids.
Claim 7
Dependent Claim
12 words
The Acmuramyl of claim 3 wherein the peptide chain comprises 2 aminoacids.
Claim 8
Dependent Claim
16 words
The Acmuramyl of claim 3 wherein the second aminoacid residue of the peptide chain is glutamic.
Claim 9
Dependent Claim
11 words
The Acmuramul of claim 5 wherein the glutamic residue is D-glutamic.
Claim 10
Dependent Claim
16 words
The Acmuramyl of claim 3 wherein the first aminoacid residue of the peptide chain is alanine.
Claim 11
Dependent Claim
17 words
The Acmuramyl of claim 3 wherein the first and second aminoacid residue is alanine and glutamic, respectively.
Claim 12
Dependent Claim
18 words
The Acmuramyl of claim 3 wherein the aminoacid residue is in its L- or in its D- forms.
Claim 13
Dependent Claim
12 words
The Acmuramyl of claim 7 wherein the second aminoacid residue is L-aspartic.
Claim 14
Dependent Claim
18 words
The Acmuramyl of claim 5 wherein the second aminoacid being glutamic, the carboxyls are either free or substituted.
Claim 15
Dependent Claim
15 words
The Acmuramyl of claim 11 wherein the first of the two aminoacid residues is L-alanine.
Claim 16
Dependent Claim
18 words
The Acmuramyl of claim 11 wherein it is the alpha-carboxyl of the glutamic which is free or substituted.
Claim 17
Dependent Claim
13 words
The Acmuramyl of claim 13 wherein the substitution in the alpha-carboxyl is amido.
Claim 18
Dependent Claim
10 words
The Acmuramyl of claim 11 wherein the glutamic is D-glutamic.
Claim 19
Dependent Claim
40 words
The Acmuramyl of claim 8 wherein the peptide which has more than two aminoacid residues is selected from the group consisting of the following aminoacid residues: meso-DAP, D-alanine, D-glutamic and L-alanine, the first two residues being of D-glutamic and L-alanine.
Claim 20
Dependent Claim
30 words
The Acmuramyl of claim 3 wherein the peptide which has more than three aminoacid residues is selected from the group consisting of the following aminoacid residues: L-threonine, L-lysine and D-alanine.
Claim 21
Dependent Claim
12 words
The Acmuramyl of claim 3 wherein the first aminoacid residue is serine.
Claim 22
Dependent Claim
29 words
The Acmuramyl of claim 3 wherein the peptide chain comprises more than two aminoacid residues, the additional aminoacid residue being linked to the gamma-carboxyl of the second aminoacid residue.
Claim 23
Dependent Claim
40 words
A compound of the formula ##STR9## wherein R 6 is methyl, R and R 1 are each hydrogen, R 2 is methyl or hydroxymethyl, X is selected from the group consisting of L-alanyl, L-seryl or glycyl, and Y is D-isoglutamine.
Claim 24
Dependent Claim
40 words
A compound of the formula ##STR9## wherein R 6 is methyl, R and R 1 are each hydrogen, R 2 is methyl or hydroxymethyl, X is selected from the group consisting of L-alanyl, L-seryl or glycyl, and Y is D-isoglutamine.
Claim 25
Dependent Claim
11 words
The compound of claim 20 wherein X is L-alanyl or L-seryl.
Claim 26
Dependent Claim
10 words
The compound of claim 20 wherein R 2 is methyl.
Claim 27
Dependent Claim
10 words
The compound of claim 20 wherein R 2 is hydroxymethyl.
Claim 28
Dependent Claim
24 words
The compound of claim 20 wherein R and R 1 are both hydrogen, R 2 is methyl, X is L-alanyl and Y is D-isoglutamine.
Claim 29
Dependent Claim
24 words
The compound of claim 20 wherein R and R 1 are both hydrogen, R 2 is methyl, X is L-seryl and Y is D-isoglutamine.
Claim 30
Dependent Claim
24 words
The compound of claim 20 wherein R and R 1 are both hydrogen, R 2 is hydroxymethyl, X is L-alanyl and Y is D-isoglutamine.
Claim 31
Dependent Claim
24 words
The compound of claim 20 wherein R and R 1 are both hydrogen, R 2 is hydroxymethyl, X is L-seryl and Y is D-isoglutamine.
Claim 32
Dependent Claim
21 words
The peptidoglycan of claim 1 wherein -Ac is acetyl, the first aminoacid residue being L-alanine and the second residue being D-glutamic.
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) | 1983-11-25 | 1984-05-26 | 1984-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-25 | 1988-05-26 | 1988-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-25 | 1992-05-26 | 1992-11-25 | $7700.00 | Window Closed / Lapsed |