US4153684A
Expired / Lapsed
US
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Immunizing and anti-infectious adjuvant agents constituted by N-acetyl-muramyl-L-alanyl-D-glutamic acid derivatives
Assignee: Bpifrance Financement SA
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Filing: 1977-03-07
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Granted: 1979-05-08
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Expires: 1997-03-07
Abstract
Abstract The invention relates to new water-soluble agents which are effective as immunizing adjuvants. These adjuvant agents are the methyl, ethyl or propyl esters of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-isoglutamine and of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid, the 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-(.alpha.-methylamide)-glutamic and 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-isoglutamine, the 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-glutamic acid and their derivatives. They are particularly useful to prepare adjuvant medicinal compositions, used for increasing the efficiency of vaccines.
Inventors
- 👤 Francoise Audibert
- 👤 Louis Chedid
- 👤 Pierre LeFrancier
- 👤 Jean Choay
- 👤 Edgar Lederer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 22:21
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; A; A61; A61K; A61K39/00; A61K39/39; A61K2039/555; A61K2039/55511; A61K2039/5555
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
58 words
Esters of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid and of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-isoglutamine corresponding to the formula ##STR5## in which R 1 is --OC n H 2n+1 , with n=1, 2 or 3, or --NH 2 , R 2 is --OC p H 2p+1 , with p=0, 1, 2 or 3, p being not equal to 0 when R 1 is --NH 2 .
Claim 2
Dependent Claim
58 words
Esters of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid and of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-isoglutamine corresponding to the formula ##STR5## in which R 1 is --OC n H 2n+1 , with n=1, 2 or 3, or --NH 2 , R 2 is --OC p H 2p+1 , with p=0, 1, 2 or 3, p being not equal to 0 when R 1 is --NH 2 .
Claim 3
Dependent Claim
14 words
The α-methyl ester of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid, corresponding to the abridged formula Mur-NAc-L-Ala-D-Glu-α-OCH 3 .
Claim 4
Dependent Claim
14 words
The α-methyl ester of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid, corresponding to the abridged formula Mur-NAc-L-Ala-D-Glu-α-OCH 3 .
Claim 5
Dependent Claim
16 words
The methyl diester of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid corresponding to the abridged formula Mur-NAc-L-Ala-D-Glu-(OCH 3 ) 2 .
Claim 6
Dependent Claim
16 words
The methyl diester of 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-glutamic acid corresponding to the abridged formula Mur-NAc-L-Ala-D-Glu-(OCH 3 ) 2 .
Claim 7
Dependent Claim
14 words
The methyl ester of the 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-isoglutamine corresponding to the abridged formula Mur-NAc-L-Ala-D-iso-Gln-(OCH 3 ).
Claim 8
Dependent Claim
14 words
The methyl ester of the 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-isoglutamine corresponding to the abridged formula Mur-NAc-L-Ala-D-iso-Gln-(OCH 3 ).
Claim 9
Dependent Claim
8 words
2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-(α-methylamide)-glutamic acid, which corresponds to the formula ##STR6##
Claim 10
Dependent Claim
8 words
2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-alanyl-D-(α-methylamide)-glutamic acid, which corresponds to the formula ##STR6##
Claim 11
Dependent Claim
34 words
2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-isoglutamine, which corresponds to the formula ##STR7## and 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-glutamic acid corresponding to the formula ##STR8## their mono and di methyl, ethyl, propyl ester derivatives and their amide derivatives possibly N substituted by methyl rests.
Claim 12
Dependent Claim
34 words
2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-isoglutamine, which corresponds to the formula ##STR7## and 2-(2-acetamido-2-deoxy-3-O-D-glucopyranosyl)-D-propionyl-L-seryl-D-glutamic acid corresponding to the formula ##STR8## their mono and di methyl, ethyl, propyl ester derivatives and their amide derivatives possibly N substituted by methyl rests.
Claim 13
Dependent Claim
3 words
The compound, 2-(2-acetamido-2-deoxy-3-O-D-glycopyranosyl)-D-propionyl-L-seryl-D-isoglutamine.
Claim 14
Dependent Claim
3 words
The compound, 2-(2-acetamido-2-deoxy-3-O-D-glycopyranosyl)-D-propionyl-L-seryl-D-isoglutamine.
Claim 15
Dependent Claim
19 words
The therapeutic composition which comprises a therapeutically acceptable carrier and in a therapeutic amount, the compound of claim 7.
Claim 16
Dependent Claim
18 words
A pharmaceutical composition which comprises an innert carrier and, in an effective amount, an ester of claim 1.
Claim 17
Dependent Claim
18 words
The pharmaceutical composition which comprises an innert carrier and, in an effective amount, an ester of claim 2.
Claim 18
Dependent Claim
18 words
The pharmaceutical composition which comprises an innert carrier and, in an effective amount, an ester of claim 3.
Claim 19
Dependent Claim
18 words
The pharmaceutical composition which comprises an innert carrier and, in an effective amount, an ester of claim 4.
Claim 20
Dependent Claim
16 words
An anti-infectious medicinal composition which comprises a pharmaceutically acceptable carrier and an ester of claim 1.
Claim 21
Dependent Claim
16 words
An anti-infectious medicinal composition which comprises a pharmaceutically acceptable carrier and an ester of claim 2.
Claim 22
Dependent Claim
16 words
An anti-infectious medicinal composition which comprises a pharmaceutically acceptable carrier and an ester of claim 3.
Claim 23
Dependent Claim
16 words
An anti-infectious medicinal composition which comprises a pharmaceutically acceptable carrier and an ester of claim 4.
Claim 24
Dependent Claim
19 words
The composition of claim 13 wherein the ester is in an amount of about 50 to about 2000 ug.
Claim 25
Dependent Claim
10 words
The composition of claim 9 wherein the carrier is oil-containing.
Claim 26
Dependent Claim
15 words
The composition of claim 9 wherein the carrier is an aqueous carrier free of oil.
Claim 27
Dependent Claim
15 words
The composition of claim 10 wherein the carrier is an aqueous carrier free of oil.
Claim 28
Dependent Claim
15 words
The composition of claim 11 wherein the carrier is an aqueous carrier free of oil.
Claim 29
Dependent Claim
15 words
The composition of claim 12 wherein the carrier is an aqueous carrier free of oil.
Claim 30
Dependent Claim
15 words
The composition of claim 19 wherein the carrier is an isotonic saline or glucose solution.
Claim 31
Dependent Claim
27 words
The method of controlling a pathogenic infection which comprises administering to a warm blooded animal in an amount effective to control bacteria, an ester of claim 1.
Claim 32
Dependent Claim
27 words
The method of controlling a pathogenic infection which comprises administering to a warm blooded animal in an amount effective to control bacteria, an ester of claim 2.
Claim 33
Dependent Claim
27 words
The method of controlling a pathogenic infection which comprises administering to a warm blooded animal in an amount effective to control bacteria, an ester of claim 3.
Claim 34
Dependent Claim
27 words
The method of controlling a pathogenic infection which comprises administering to a warm blooded animal in an amount effective to control bacteria, an ester of claim 4.
Claim 35
Dependent Claim
10 words
The method of claim 24 wherein the administration is oral.
Claim 36
Dependent Claim
10 words
The method of claim 25 wherein the administration is oral.
Claim 37
Dependent Claim
10 words
The method of claim 26 wherein the administration is oral.
Claim 38
Dependent Claim
10 words
The method of claim 27 wherein the administration is oral.
Claim 39
Dependent Claim
11 words
The pharmaceutical composition of claim 9 which comprises an immunising agent.
Claim 40
Dependent Claim
11 words
The pharmaceutical composition of claim 10 which comprises an immunising agent.
Claim 41
Dependent Claim
11 words
The pharmaceutical composition of claim 11 which comprises an immunising agent.
Claim 42
Dependent Claim
11 words
The pharmaceutical composition of claim 12 which comprises an immunising agent.
Claim 43
Dependent Claim
20 words
The therapeutical composition which comprises a therapeutically acceptable carrier and in a therapeutically acceptable amount, the compound of claim 5.
Claim 44
Dependent Claim
15 words
The therapeutical composition of claim 36 wherein the carrier is aqueous and free of oil.
Claim 45
Dependent Claim
11 words
The therapeutical composition of claim 36 wherein the carrier contains oil.
Claim 46
Dependent Claim
20 words
The therapeutical composition which comprises a therapeutically acceptable carrier and in a therapeutically acceptable amount, the compound of claim 6.
Claim 47
Dependent Claim
15 words
The therapeutical composition of claim 39 wherein the carrier is aqueous and free of oil.
Claim 48
Dependent Claim
11 words
The therapeutical composition of claim 38 wherein the carrier contains oil.
References Cited (Backward Citations)
FR2160326A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-07 | 1982-11-06 | 1983-05-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-07 | 1986-11-06 | 1987-05-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-07 | 1990-11-06 | 1991-05-08 | $7700.00 | Window Closed / Lapsed |