US4427659A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Muramyl peptide substituted on a peptide nitrogen and medicaments containing the same
Assignee: Bpifrance Financement SA
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Filing: 1982-01-06
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Granted: 1984-01-24
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Expires: 2002-01-06
Abstract
Abstract The invention relates to novel compounds of the muramyl-peptide type and to their uses. The muramyl-peptides according to the invention comprise at least two aminoacyl residues in the peptide chain, the second of these aminoacyl residues being D-glutamyl, and they are characterized in that the nitrogen of the first amino-acyl, and forming part of the pepetide linkage connecting the muramyl group to the peptide residue, is substituted by an alkyl group. These compounds are useful notably for the preparation of pharmaceutical compositions, in particular by reason of their regulatory properties on the immune responses of the organism.
Inventors
- 👤 Pierre Le Francier
- 👤 Francoise Audibert
- 👤 Jean Choay
- 👤 Louis Chedid
- 👤 Edgar Lederer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 11:22
CPC Classifications
C; C07; C07K; C07K9/00; C07K9/001; C07K9/005; A; A61; A61P; A61P37/00; A61P37/02; A61P37/04
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
18 words
A compound which is selected from the group consisting of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine, the methyl ester of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine and N-acetyl-Nor-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 2
Dependent Claim
18 words
A compound which is selected from the group consisting of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine, the methyl ester of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine and N-acetyl-Nor-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 3
Dependent Claim
6 words
The compound of claim 1, N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 4
Dependent Claim
12 words
The compound of claim 1, which is the methyl ester of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 5
Dependent Claim
6 words
The compound of claim 1, N-acetyl-Nor-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 6
Dependent Claim
49 words
A therapeutic composition of high and improved therapeutic index which composition is virtually apyrogenic while concurrently being an effective immunostimulant, which composition comprises a biologically acceptable carrier and in a biologically effective amount, a compound selected from the group consisting of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine, the methyl ester of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine and N-acetyl-Nor-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 7
Dependent Claim
49 words
A therapeutic composition of high and improved therapeutic index which composition is virtually apyrogenic while concurrently being an effective immunostimulant, which composition comprises a biologically acceptable carrier and in a biologically effective amount, a compound selected from the group consisting of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine, the methyl ester of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine and N-acetyl-Nor-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 8
Dependent Claim
10 words
The composition of claim 5 wherein the compound is N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 9
Dependent Claim
14 words
The composition of claim 5 wherein the compound is the methyl ester of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 10
Dependent Claim
10 words
The composition of claim 5 wherein the compound is N-acetyl-Nor-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 11
Dependent Claim
8 words
The composition of claim 5 which is liposome.
Claim 12
Dependent Claim
10 words
The compound of claim 5 wherein the carrier is aqueous.
Claim 13
Dependent Claim
15 words
The compound of claim 5 wherein the composition is adapted for oral, parenteral intradermal administration.
Claim 14
Dependent Claim
129 words
A therapeutic method which comprises administering to a host and stimulating the host's immunological response virtually without increasing the temperature of the host's body, a biological active composition of high and improved therapeutic index, which composition is virtually apyrogenic and effective to stimulate the host's immunological response and which composition is administered in an immunostimulating amount and comprises a biologically acceptable carrier and a compound of the formula ##STR7## wherein Y is hydroxyl, amino or alkoxy of 1 to 10 carbon atoms, Z is hydroxyl, amino or alkoxy of 1 to 10 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms, R 2 is hydrogen or succinyl and X is N-alkyl.sub.(1-4) -L-alanyl, N-alkyl.sub.(1-4) -L-seryl, N-alkyl.sub.(1-4) -L-valyl or glycyl, the second aminoacid residue being of the D-series.
Claim 15
Dependent Claim
129 words
A therapeutic method which comprises administering to a host and stimulating the host's immunological response virtually without increasing the temperature of the host's body, a biological active composition of high and improved therapeutic index, which composition is virtually apyrogenic and effective to stimulate the host's immunological response and which composition is administered in an immunostimulating amount and comprises a biologically acceptable carrier and a compound of the formula ##STR7## wherein Y is hydroxyl, amino or alkoxy of 1 to 10 carbon atoms, Z is hydroxyl, amino or alkoxy of 1 to 10 carbon atoms, R 1 is alkyl of 1 to 4 carbon atoms, R 2 is hydrogen or succinyl and X is N-alkyl.sub.(1-4) -L-alanyl, N-alkyl.sub.(1-4) -L-seryl, N-alkyl.sub.(1-4) -L-valyl or glycyl, the second aminoacid residue being of the D-series.
Claim 16
Dependent Claim
27 words
The therapeutic method of claim 12 wherein in the compound of the composition, Y is alkoxy selected from methoxy butoxy, decanoxy, or NHC 4 H 3 .
Claim 17
Dependent Claim
31 words
The therapeutic method of claim 12 wherein in the compound of the composition, Y is alkoxy selected from methoxy butoxy, decanoxy, or NHC 4 H 3 and X is N-alkyl.sub.(1-4) -L-alanyl.
Claim 18
Dependent Claim
12 words
The therapeutic method of claim 12 wherein there is administered N-acetyl-muramyl-L -(N-methyl)-alanyl-D-isoglutamine.
Claim 19
Dependent Claim
15 words
The therapeutic method of claim 12 wherein there is administered the methyl ester of N-acetyl-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 20
Dependent Claim
11 words
The therapeutic method of claim 12 wherein there is administered N-acetyl-Nor-muramyl-L-(N-methyl)-alanyl-D-isoglutamine.
Claim 21
Dependent Claim
27 words
The therapeutic method of claim 12 wherein the amount administered is a dosage in the range from about 10 to 1,000 microgram per kilogram of body weight.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-01-23 | 1987-07-25 | 1988-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-01-23 | 1991-07-25 | 1992-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-01-23 | 1995-07-25 | 1996-01-24 | $7700.00 | Window Closed / Lapsed |