US4399124A
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Peptides having immunostimulating properties and pharmaceutical compositions containing them
Assignee: Institut Pasteur
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Filing: 1980-10-01
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Granted: 1983-08-16
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Expires: 2000-10-01
Abstract
Abstract PCT No. PCT/FR80/00142 Sec. 371 Date Jun. 1, 1981 Sec. 102(e) Date May 28, 1981 PCT Filed Oct. 1, 1980 PCT Pub. No. WO81/00847 PCT Pub. Date Apr. 2, 1981.Peptides having immunostimulating properties making them applicable to pharmaceutical compositions for the treatment or prevention of infections. They contain the sequence prolyl glycyl.
Inventors
- 👤 Robert M. Fauve
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 14:43
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/18; A; A61; A61K; A61K38/00; Y; Y02; Y02A; Y02A50/00; Y02A50/30; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/14
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
53 words
A method of stimulating macrophages in vivo in a host which comprises administering to said host an immunostimulant effective amount of a biologically active composition which comprises a biologically acceptable carrier and a peptide which is effective for stimulating macrophages in vivo having a prolyl→prolyl→glycyl sequence and a maximum of seven aminoacyl residues.
Claim 2
Independent Claim
53 words
A method of stimulating macrophages in vivo in a host which comprises administering to said host an immunostimulant effective amount of a biologically active composition which comprises a biologically acceptable carrier and a peptide which is effective for stimulating macrophages in vivo having a prolyl→prolyl→glycyl sequence and a maximum of seven aminoacyl residues.
Claim 3
Dependent Claim
12 words
The method of claim 1 wherein said peptide has a prolyl→prolyl→glycyl→phenylalanyl sequence.
Claim 4
Dependent Claim
16 words
The method of claim 2 wherein the phenylalanyl residue carries the C-terminal end of said peptide.
Claim 5
Dependent Claim
28 words
The method of claim 1 wherein the amino group of the first prolyl residue of said prolyl→prolyl→glycyl sequence is linked through a peptide linkage with another aminoacyl residue.
Claim 6
Dependent Claim
20 words
The method of claim 4 wherein said aminoacyl residue is selected from the group consisting of arginyl, lysyl or histidyl.
Claim 7
Independent Claim
29 words
The method of any one of claims 1, 2, 3, 4 or 5 in which all the aminoacyl residues of said peptide, with the exception of glycine, are levorotatory.
Claim 8
Dependent Claim
21 words
The method of claim 1 wherein the peptide is a pentapeptide selected from the group consisting of: Arginyl→prolyl→prolyl→glycyl→phenylalanine; lysyl→prolyl→prolyl→glycyl→phenylalanine; and histidyl→prolyl→prolyl→glycyl→phenylalanine.
Claim 9
Dependent Claim
37 words
The method of claim 7 wherein from 1 to 2 additional aminoacyl residues are linked to the N-terminal aminoacyl residue of said peptides, said additional aminoacyl residue being selected from the group consisting of lysyl and methionyl.
Claim 10
Dependent Claim
24 words
The method of claim 1 wherein the carboxylic acid group of the glycyl residue is linked through a peptide linkage with another aminoacyl residue.
Claim 11
Dependent Claim
66 words
An immunostimulant peptide which peptide has not more than seven amino acid residues, which peptide has the following amino acid sequence: X→prolyl→prolyl→glycyl→phenylalanyl→Y, wherein X is an amino acid residue selected from the group consisting of lysyl and histidyl, and Y is at least one amino acid residue selected from the amino acids consisting of proline and serine, but both residues not being the same, or hydroxyl.
Claim 12
Dependent Claim
66 words
An immunostimulant peptide which peptide has not more than seven amino acid residues, which peptide has the following amino acid sequence: X→prolyl→prolyl→glycyl→phenylalanyl→Y, wherein X is an amino acid residue selected from the group consisting of lysyl and histidyl, and Y is at least one amino acid residue selected from the amino acids consisting of proline and serine, but both residues not being the same, or hydroxyl.
Claim 13
Dependent Claim
20 words
The immunostimulant of claim 10 wherein the peptide is selected from the group consisting of: Lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline; histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; and histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline.
Claim 14
Dependent Claim
16 words
The peptide of claim 10 which is a pentapeptide having the following amino acid sequence: Lysyl→prolyl→prolyl→glycyl→phenylalanyl.
Claim 15
Dependent Claim
16 words
The peptide of claim 10 which is a pentapeptide having the following amino acid sequence: Histidyl→prolyl→prolyl→glycyl→phenylalanyl.
Claim 16
Dependent Claim
23 words
The peptide of any of claims 10, 11, 12 or 13 wherein, with the exception of glycine, all the aminoacyl residues are levorotatory.
Claim 17
Dependent Claim
88 words
A composition for stimulating an immune response in a host which comprises a biologically acceptable carrier and an immunostimulant effective amount of a pharmacologically active peptide, said peptide having a maximum of seven amino acid residues, which peptide has the following acid sequence: x→prolyl→prolyl→glycyl→phenylalanyl→Y, wherein X is an amino acid residue selected from the group consisting of lysyl and histidyl, and Y is at least one amino acid residue selected from the amino acids consisting of proline and serine but both residues not being the same, or hydroxyl.
Claim 18
Dependent Claim
88 words
A composition for stimulating an immune response in a host which comprises a biologically acceptable carrier and an immunostimulant effective amount of a pharmacologically active peptide, said peptide having a maximum of seven amino acid residues, which peptide has the following acid sequence: x→prolyl→prolyl→glycyl→phenylalanyl→Y, wherein X is an amino acid residue selected from the group consisting of lysyl and histidyl, and Y is at least one amino acid residue selected from the amino acids consisting of proline and serine but both residues not being the same, or hydroxyl.
Claim 19
Dependent Claim
20 words
The composition of claim 15 wherein the peptide is selected from the group consisting of: Lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline; histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; and histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline.
Claim 20
Dependent Claim
15 words
The composition of claim 15 wherein the peptide is a pentapeptide having the formula: Lysyl→prolyl→prolyl→glycyl→phenylalanyl.
Claim 21
Dependent Claim
15 words
The composition of claim 15 wherein the peptide is a pentapeptide having the formula: Histidyl→prolyl→prolyl→glycyl→phenylalanyl.
Claim 22
Dependent Claim
17 words
The composition of claim 17 wherein, with the exception of glycine, all the aminoacyl residues are levorotatory.
Claim 23
Independent Claim
89 words
A method for stimulating an immunal response in a host which comprises a administering biologically acceptable carrier and an immunostimulant effective amount of a pharmacologically active peptide, said peptide having a maximum of seven amino acid residues, which peptide has the following acid sequence: X→prolyl→prolyl→glycyl→phenylalanyl→Y, wherein X is an amino acid residue selected from the group consisting of lysyl and histidyl, and Y is at least one amino acid residue selected from the amino acids consisting of proline and serine, but both residues not being the same, or hydroxyl.
Claim 24
Independent Claim
89 words
A method for stimulating an immunal response in a host which comprises a administering biologically acceptable carrier and an immunostimulant effective amount of a pharmacologically active peptide, said peptide having a maximum of seven amino acid residues, which peptide has the following acid sequence: X→prolyl→prolyl→glycyl→phenylalanyl→Y, wherein X is an amino acid residue selected from the group consisting of lysyl and histidyl, and Y is at least one amino acid residue selected from the amino acids consisting of proline and serine, but both residues not being the same, or hydroxyl.
Claim 25
Independent Claim
50 words
A method of stimulating macrophages in vivo in a host which comprises administering to said host an immunostimulant effective amount of a biologically active composition which comprises a biologically acceptable carrier and a hexa or hepta peptide selected from the group consisting of: lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline; Histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; Histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline; arginyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; and arginyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline.
Claim 26
Independent Claim
50 words
A method of stimulating macrophages in vivo in a host which comprises administering to said host an immunostimulant effective amount of a biologically active composition which comprises a biologically acceptable carrier and a hexa or hepta peptide selected from the group consisting of: lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; lysyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline; Histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; Histidyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline; arginyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.serine; and arginyl→prolyl→prolyl→glycyl→phenylalanyl.fwdarw.seryl→proline.
Claim 27
Dependent Claim
21 words
The method of claim 20 wherein all of the aminoacyl residues forming the peptide, with the exception of glycine, are levoratory.
Claim 28
Dependent Claim
24 words
The method of claim 20 wherein the administration is parenterally in an amount which ranges from about 10 -5 to about 10 -3 mole.
Claim 29
Dependent Claim
17 words
The method of claim 23 wherein the dosage administered ranges from 0.25·10 -4 to 1.10 -4 mole.
Claim 30
Dependent Claim
23 words
The method of claim 24 wherein the administration is parenterally in an amount of from about 10 -5 to about 10 -3 mole.
Claim 31
Dependent Claim
19 words
The method of claim 25 wherein the dosage administered ranges from about 0.25·10 -4 to about 1.10 -4 mole.
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) | 1986-08-15 | 1987-02-14 | 1987-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-15 | 1991-02-14 | 1991-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-15 | 1995-02-14 | 1995-08-16 | $7700.00 | Window Closed / Lapsed |