US4186194A
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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: 1974-10-22
•
Granted: 1980-01-29
•
Expires: 1994-10-22
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
2026-11-03 13:08
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: 104
Claim 1
Independent Claim
134 words
The method for enhancing the immunization of a host which comprises administering to a host subject to an immune response caused by administration of an antigen capable of increasing the immune response of the host, a composition which comprises a biologically acceptable carrier and a compound defined by having an N-Acmuramyl, wherein -Ac is acetyl or glycolyl, to the carboxyl of the N-Acmuramyl there being linked a peptide chain which comprises 2 to 8 residues of aminoacids, the first aminoacid residue comprising alanyl, seryl or glycyl, and the second aminoacid residue comprising glutamyl or aspartyl, one of the carboxyl of this second aminoacid residue being either free or substituted, or when there are more than two aminoacid residues, the carboxyl of this second aminoacid being either free, substituted or linked to another aminoacid residue.
Claim 2
Independent Claim
134 words
The method for enhancing the immunization of a host which comprises administering to a host subject to an immune response caused by administration of an antigen capable of increasing the immune response of the host, a composition which comprises a biologically acceptable carrier and a compound defined by having an N-Acmuramyl, wherein -Ac is acetyl or glycolyl, to the carboxyl of the N-Acmuramyl there being linked a peptide chain which comprises 2 to 8 residues of aminoacids, the first aminoacid residue comprising alanyl, seryl or glycyl, and the second aminoacid residue comprising glutamyl or aspartyl, one of the carboxyl of this second aminoacid residue being either free or substituted, or when there are more than two aminoacid residues, the carboxyl of this second aminoacid being either free, substituted or linked to another aminoacid residue.
Claim 3
Dependent Claim
11 words
The method of claim 1 wherein there is administered, N-acetylmuramyl-L-alanyl-D-glutamic acid.
Claim 4
Dependent Claim
10 words
The method of claim 1 wherein there is administered, N-acetylmuramyl-L-alanyl-D-isoglutamine.
Claim 5
Dependent Claim
111 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of a water-soluble peptidoglycan which is a disaccharide of linked N-acetylglucosamine and N-acylmuramyl, wherein the -acyl is acetyl or glycolyl, to the carboxyl of the N-acylmuramyl there being linked a peptide chain which comprises 2 to 8 residues of aminoacids, the first aminoacid residue comprising alanyl, seryl or glycyl, and the second aminoacid residue comprising glutamyl or aspartyl, one of the carboxyl of this second aminoacid residue being either free, substituted or when there are more than two amino acid residues, the carboxyl of this second aminoacid residue being either free, substituted or linked to another aminoacid residue.
Claim 6
Dependent Claim
111 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of a water-soluble peptidoglycan which is a disaccharide of linked N-acetylglucosamine and N-acylmuramyl, wherein the -acyl is acetyl or glycolyl, to the carboxyl of the N-acylmuramyl there being linked a peptide chain which comprises 2 to 8 residues of aminoacids, the first aminoacid residue comprising alanyl, seryl or glycyl, and the second aminoacid residue comprising glutamyl or aspartyl, one of the carboxyl of this second aminoacid residue being either free, substituted or when there are more than two amino acid residues, the carboxyl of this second aminoacid residue being either free, substituted or linked to another aminoacid residue.
Claim 7
Dependent Claim
16 words
The composition of claim 4 wherein the peptide chain is of 2 to 5 aminoacid residues.
Claim 8
Dependent Claim
40 words
The composition of claim 5 wherein the peptide chain comprises two aminoacid residues and, in addition to said first two residues, an aminoacid residue selected from the group consisting of the following aminoacid residues: meso-DAP, lysyl, gamma-amino-butyryl and beta-hydroxy-diaminopimelic acid.
Claim 9
Dependent Claim
38 words
The composition of claim 5 wherein the peptide chain comprises two aminoacid residues and, in addition to said first two residues, an aminoacid residue selected from the group consisting of the following aminoacid residues: L-threonyl, L-lysyl and D-alanyl.
Claim 10
Dependent Claim
29 words
The composition of claim 5 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 11
Dependent Claim
13 words
The composition of claim 4 wherein the peptide chain comprises two aminoacid residues.
Claim 12
Dependent Claim
24 words
The composition of claim 9 wherein the peptide chain comprises two aminoacid residues, the second being glutamyl whose carboxyl is either free or substituted.
Claim 13
Dependent Claim
18 words
The composition of claim 10 wherein it is the alpha-carboxyl of the glutamyl which is free or substituted.
Claim 14
Dependent Claim
13 words
The composition of claim 11 wherein the substitution on the alpha-carboxyl is amido.
Claim 15
Dependent Claim
10 words
The composition of claim 10 wherein the glutamyl is D-glutamyl.
Claim 16
Dependent Claim
15 words
The composition of claim 13 wherein the first of the two aminoacid residues is L-alanyl.
Claim 17
Dependent Claim
17 words
The composition of claim 9 wherein the first and second aminoacid residue is respectively, alanyl and glutamyl.
Claim 18
Dependent Claim
18 words
The composition of claim 15 wherein the aminoacid residue is in its L- form or its D- form.
Claim 19
Dependent Claim
12 words
The composition of claim 15 wherein the first aminoacid residue is L-alanyl.
Claim 20
Dependent Claim
17 words
A composition which comprises an antigen and a biologically effective amount of the saccharide of claim 15.
Claim 21
Dependent Claim
17 words
A composition which comprises an immunogen and a biologically effective amount of the saccharide of claim 15.
Claim 22
Dependent Claim
16 words
A serum which comprises antibodies and a biologically effective amount of the saccharide of claim 15.
Claim 23
Dependent Claim
27 words
A method for providing an immune response in a host which comprises administering an amount effective to promote an immune response of the composition of claim 15.
Claim 24
Dependent Claim
12 words
The composition of claim 15 wherein the carrier is a water-in-oil emulsion.
Claim 25
Dependent Claim
24 words
A vaccine of bacterial or viral origin and in amounts effective to enhance the effect of the vaccine, the saccharide defined in claim 15.
Claim 26
Dependent Claim
26 words
The method of vaccination of a human or animal host which comprises administering to that host an amount effective for vaccination, the vaccine of claim 23.
Claim 27
Dependent Claim
18 words
The composition of claim 4 wherein the peptidoglycan is of recurring disaccharides which are linked to each other.
Claim 28
Dependent Claim
12 words
The composition of claim 25 wherein the peptidoglycan is of two disaccharides.
Claim 29
Dependent Claim
35 words
The composition of claim 26 wherein one of the disaccharides has a linked peptide chain of seven aminoacid residues which are ##STR8## in which a D-Ala is optionally linked to one of the meso-DAP residues.
Claim 30
Dependent Claim
26 words
The composition of claim 4 wherein the peptidoglycan is of recurring disaccharides linked to each other, the peptide chain being linked to at least one disaccharide.
Claim 31
Dependent Claim
38 words
The composition of claim 4 wherein the peptidoglycan is of recurring disaccharides which are linked to each other by their disaccharides or through the peptide chains of another adjoining disaccharide, or through both the disaccharide and the peptide.
Claim 32
Dependent Claim
32 words
The composition of claim 4 wherein the peptide chain which has more than two aminoacid residues is selected from the group consisting of the following aminoacid residues: meso-DAP, D-alanyl, D-glutamyl and L-alanyl.
Claim 33
Dependent Claim
61 words
The composition of claim 4 wherein the N-acylmuramyl, the N-acetylglucosamine, and the aminoacid residues L-alanyl, D-glutamyl, meso-alpha-epsilon-diaminopimelyl and D-alanyl residues are present in the following respective molar ratios: ______________________________________
1:1:1:1:1 (disaccharide-tripeptide)
1:1:1:1:1:1 (disaccharide-tetrapeptide)
1:1:2:2:2:1 (disaccharide-heptapeptide)
1:1:2:2:2:2 (disaccharide-octapeptide)
2:2:2:2:2:1 (tetrasaccharide-heptapeptide)
2:2:2:2:2:2 (tetrasaccharide-octapeptide),
______________________________________ wherein the absence of the sixth figure in the ratios signifies that the corresponding peptidoglycan is free of D-alanyl.
Claim 34
Dependent Claim
11 words
The composition of claim 4 wherein the peptide chain is ##STR9##
Claim 35
Dependent Claim
11 words
The composition of claim 4 wherein the peptide chain is ##STR10##
Claim 36
Dependent Claim
28 words
The composition of claim 4 wherein the disaccharide is at least one of the following tetrasaccharides: ##STR11## wherein N-Ac-Glc defines the N-acetylglucosamine and N-Acyl-Mur defines the N-acylmuramyl saccharide.
Claim 37
Dependent Claim
30 words
The composition of claim 34 wherein the peptide chain of the tetrasaccharides of formula VIII and IX comprises D-alanyl linked to one of the meso-DAP group of the peptide chain.
Claim 38
Dependent Claim
16 words
The composition of claim 4 wherein in the peptide chain, the first aminoacid residue is alanyl.
Claim 39
Dependent Claim
10 words
The composition of claim 36 wherein the alanyl is L-alanyl.
Claim 40
Dependent Claim
11 words
The composition of claim 36 wherein the alanyl residue is D-alanyl.
Claim 41
Dependent Claim
16 words
The composition of claim 4 wherein in the peptide chain, the second aminoacid residue is glutamyl.
Claim 42
Dependent Claim
10 words
The composition of claim 39 wherein the glutamyl is D-glutamyl.
Claim 43
Dependent Claim
12 words
The composition of claim 4 wherein the first amonoacid residue is seryl.
Claim 44
Dependent Claim
12 words
The composition of claim 4 wherein in the N-Acmuramyl, -Ac is acetyl.
Claim 45
Dependent Claim
12 words
The composition of claim 4 wherein in the N-Acmuramyl, -Ac is glycolyl.
Claim 46
Dependent Claim
12 words
The composition of claim 41 wherein the first aminoacid residue is glycyl.
Claim 47
Dependent Claim
29 words
The composition of claim 4 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 48
Dependent Claim
17 words
A composition which comprises an antigen and a biologically effective amount of the saccharide of claim 4.
Claim 49
Dependent Claim
17 words
A composition which comprises an immunogen and a biologically effective amount of the saccharide of claim 4.
Claim 50
Dependent Claim
16 words
A serum which comprises antibodies and a biologically effective amount of the saccharide of claim 4.
Claim 51
Dependent Claim
27 words
A method for providing an immune response in a host which comprises administering an amount effective to promote an immune response of the composition of claim 4.
Claim 52
Dependent Claim
14 words
The method of claim 49 wherein the host is man or a warm-blooded animal.
Claim 53
Dependent Claim
12 words
The composition of claim 4 wherein the carrier is a water-in-oil emulsion.
Claim 54
Dependent Claim
24 words
A vaccine of bacterial or viral origin and in amounts effective to enhance the effect of the vaccine, the saccharide defined in claim 4.
Claim 55
Dependent Claim
15 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of N-acetylmuramyl-L-alanyl-D-isoglutamine.
Claim 56
Dependent Claim
15 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of N-acetylmuramyl-L-alanyl-D-isoglutamine.
Claim 57
Dependent Claim
17 words
A composition which comprises an antigen and a biologically effective amount of the saccharide of claim 53.
Claim 58
Dependent Claim
17 words
A composition which comprises an immunogen and a biologically effective amount of the saccharide of claim 53.
Claim 59
Dependent Claim
16 words
A serum which comprises antibodies and a biologically effective amount of the saccharide of claim 53.
Claim 60
Dependent Claim
27 words
A method for providing an immune response in a host which comprises administering an amount effective to promote an immune response of the composition of claim 53.
Claim 61
Dependent Claim
14 words
The method of claim 57 wherein the host is man or a warm-blooded animal.
Claim 62
Dependent Claim
12 words
The composition of claim 53 wherein the carrier is a water-in-oil emulsion.
Claim 63
Dependent Claim
24 words
A vaccine of bacterial or viral origin and in amounts effective to enhance the effect of the vaccine, the saccharide defined in claim 53.
Claim 64
Dependent Claim
26 words
The method of vaccination of a human or animal host which comprises administering to that host an amount effective for vaccination, the vaccine of claim 60.
Claim 65
Dependent Claim
49 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of water-soluble N-acetylmuramyl, wherein to its carboxyl group, there is linked a peptide chain constituted by a first aminoacid residue linked to a second aminoacid residue, L-alanyl and D-glutamyl respectively, wherein the carboxylic groups are free.
Claim 66
Dependent Claim
49 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of water-soluble N-acetylmuramyl, wherein to its carboxyl group, there is linked a peptide chain constituted by a first aminoacid residue linked to a second aminoacid residue, L-alanyl and D-glutamyl respectively, wherein the carboxylic groups are free.
Claim 67
Dependent Claim
17 words
A composition which comprises an antigen and a biologically effective amount of the saccharide of claim 62.
Claim 68
Dependent Claim
17 words
A composition which comprises an immunogen and a biologically effective amount of the saccharide of claim 62.
Claim 69
Dependent Claim
16 words
A serum which comprises antibodies and a biologically effective amount of the saccharide of claim 62.
Claim 70
Dependent Claim
27 words
A method for providing an immune response in a host which comprises administering an amount effective to promote an immune response of the composition of claim 62.
Claim 71
Dependent Claim
14 words
The method of claim 66 wherein the host is man or a warm-blooded animal.
Claim 72
Dependent Claim
24 words
A vaccine of bacterial or viral origin and in amounts effective to enhance the effect of the vaccine, the saccharide defined in claim 62.
Claim 73
Dependent Claim
26 words
The method of vaccination of a human or animal host which comprises administering to that host an amount effective for vaccination, the vaccine of claim 68.
Claim 74
Dependent Claim
100 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of water-soluble saccharide, N-Acmuramyl wherein -Ac is acetyl or glycolyl, to the carboxyl of the N-Acylmuramyl there being linked a peptide chain which comprises 2 to 8 residues of aminoacids, the first aminoacid residue comprising alanyl, seryl or glycyl, and the second aminoacid residue comprising glutamyl or aspartyl residue, one of the carboxyl of this second aminoacid residue being either free, substituted or when there are more than two aminoacid residues, the carboxyl of this second aminoacid being either free, substituted or linked to another aminoacid residue.
Claim 75
Dependent Claim
100 words
A composition which comprises a biologically acceptable carrier and a biologically effective amount of water-soluble saccharide, N-Acmuramyl wherein -Ac is acetyl or glycolyl, to the carboxyl of the N-Acylmuramyl there being linked a peptide chain which comprises 2 to 8 residues of aminoacids, the first aminoacid residue comprising alanyl, seryl or glycyl, and the second aminoacid residue comprising glutamyl or aspartyl residue, one of the carboxyl of this second aminoacid residue being either free, substituted or when there are more than two aminoacid residues, the carboxyl of this second aminoacid being either free, substituted or linked to another aminoacid residue.
Claim 76
Dependent Claim
15 words
The composition of claim 70 wherein the peptide chain comprises 2 to 5 aminoacid residues.
Claim 77
Dependent Claim
16 words
The composition of claim 71 wherein the second aminoacid residue of the peptide chain is glutamyl.
Claim 78
Dependent Claim
10 words
The composition of claim 72 wherein the glutamyl is D-glutamyl.
Claim 79
Dependent Claim
16 words
The composition of claim 71 wherein the first aminoacid residue of the peptide chain is alanyl.
Claim 80
Dependent Claim
12 words
The composition of claim 71 wherein the first aminoacid residue is L-alanyl.
Claim 81
Dependent Claim
24 words
The composition of claim 71 wherein the peptide chain comprises two aminoacid residues, the second being glutamyl whose carboxyl is either free or substituted.
Claim 82
Dependent Claim
18 words
The composition of claim 76 wherein it is the alpha-carboxyl or the glutamyl which is free or substituted.
Claim 83
Dependent Claim
13 words
The composition of claim 77 wherein the substitution on the alpha-carboxyl is amido.
Claim 84
Dependent Claim
10 words
The composition of claim 78 wherein the glutamyl is D-glutamyl.
Claim 85
Dependent Claim
15 words
The composition of claim 79 wherein the first of the two aminoacid residues is L-alanyl.
Claim 86
Dependent Claim
29 words
The composition of claim 71 wherein the peptide chain comprises as the first aminoacid residue L-alanyl, as the second aminoacid residue D-glutamyl and as the third aminoacid residue, lysyl.
Claim 87
Dependent Claim
14 words
The composition of claim 81 wherein the peptide chain comprises a fourth aminoacid residue.
Claim 88
Dependent Claim
12 words
The composition of claim 82 wherein the fourth aminoacid residue is alanyl.
Claim 89
Dependent Claim
11 words
The composition of claim 83 wherein the alanyl residue is D-alanyl.
Claim 90
Dependent Claim
13 words
The composition of claim 70 wherein the peptide chain comprises two aminoacid residues.
Claim 91
Dependent Claim
20 words
The composition of claim 85 wherein in the N-Acmuramyl, the first and second aminoacid residue is alanyl and glutamyl, respectively.
Claim 92
Dependent Claim
18 words
The composition of claim 86 wherein the aminoacid residue is in its L- or in its D- forms.
Claim 93
Dependent Claim
17 words
A composition which comprises an antigen and a biologically effective amount of the saccharide of claim 86.
Claim 94
Dependent Claim
17 words
A composition which comprises an immunogen and a biologically effective amount of the saccharide of claim 86.
Claim 95
Dependent Claim
16 words
A serum which comprises antibodies and a biologically effective amount of the saccharide of claim 86.
Claim 96
Dependent Claim
24 words
A vaccine of bacterial or viral origin and in amounts effective to enhance the effect of the vaccine, the saccharide defined in claim 86.
Claim 97
Dependent Claim
26 words
The method of vaccination of a human or animal host which comprises administering to that host an amount effective for vaccination, the vaccine of claim 91.
Claim 98
Dependent Claim
12 words
The composition of claim 70 wherein in the N-Acmuramyl, -Ac is acetyl.
Claim 99
Dependent Claim
12 words
The composition of claim 70 wherein in the N-Acmuramyl, -Ac is glycolyl.
Claim 100
Dependent Claim
17 words
A composition which comprises an antigen and a biologically effective amount of the saccharide of claim 70.
Claim 101
Dependent Claim
17 words
A composition which comprises an immunogen and a biologically effective amount of the saccharide of claim 70.
Claim 102
Dependent Claim
16 words
A serum which comprises antibodies and a biologically effective amount of the saccharide of claim 70.
Claim 103
Dependent Claim
24 words
A vaccine of bacterial or viral origin and in amounts effective to enhance the effect of the vaccine, the saccharide defined in claim 70.
Claim 104
Dependent Claim
26 words
The method of vaccination of a human or animal host which comprises administering to that host an amount effective for vaccination, the vaccine of claim 98.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-01-28 | 1983-07-30 | 1984-01-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-28 | 1987-07-30 | 1988-01-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-28 | 1991-07-30 | 1992-01-29 | $7700.00 | Window Closed / Lapsed |