US4505853A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Enzyme-resistant immunomodulatory peptides
Assignee: Ortho Pharmaceutical Corp
•
Filing: 1983-11-18
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Granted: 1985-03-19
•
Expires: 2003-11-18
Abstract
Abstract Peptides which have thymopoeitin-like or splenin-like activity combined with greatly increased resistance to degradation by enzymes. The peptides are useful for treatment of immunoregulatory disorders. Also provided are methods of treating immunoregulatory disorders and compositions used in these methods.
Inventors
- 👤 Gideon Goldstein
- 👤 George Heavner
- 👤 Daniel Kroon
- 👤 Tapan Audhya
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:54
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/10; C07K14/00; C07K14/435; C07K14/575; C07K14/66; C07K14/662; A; A61; A61P; A61P37/00; A61P5/00; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/18
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
180 words
A peptide having the formula: R--V--W--X--Y--Z--R.sup.1 or a pharmaceutically acceptable acid- or base-addition salt thereof, wherein: R is H, NH 2 , acyl-NH, CH 3 NH, or pyro-GLU-NH; ##STR5## W is PRO, dehydro PRO, or ##STR6## A individually is C 2 -C 6 loweralkyl; B individually is C 1 -C 3 loweralkyl; A and B taken together are --(CH 2 ) 4 --or --(CH 2 ) 5 --; X is D-ASP, ASP, D-GLU, or GLU; Y is GLY, VAL, LEU, nor-LEU, PHE, ILE, LYS, GLN, GLU, ALA, D-VAL, D-LEU, D- nor LEU, D-PHE, D-ILE, D-LYS, D-GLN, D-GLU, or D-ALA; Z is ##STR7## D is H or 1 or 2 substituents which increase or do not substantially decrease the acidity of the phenol proton; E is H or C 1 -C 3 loweralkyl; R 1 is OH, NHR", ##STR8## and R" and R'" are individually H or lower alkyl; provided that V may be D- or L-isomer if R is other than H, and further provided that no more than one of V, X, and Y is a D amino acid.
Claim 2
Dependent Claim
180 words
A peptide having the formula: R--V--W--X--Y--Z--R.sup.1 or a pharmaceutically acceptable acid- or base-addition salt thereof, wherein: R is H, NH 2 , acyl-NH, CH 3 NH, or pyro-GLU-NH; ##STR5## W is PRO, dehydro PRO, or ##STR6## A individually is C 2 -C 6 loweralkyl; B individually is C 1 -C 3 loweralkyl; A and B taken together are --(CH 2 ) 4 --or --(CH 2 ) 5 --; X is D-ASP, ASP, D-GLU, or GLU; Y is GLY, VAL, LEU, nor-LEU, PHE, ILE, LYS, GLN, GLU, ALA, D-VAL, D-LEU, D- nor LEU, D-PHE, D-ILE, D-LYS, D-GLN, D-GLU, or D-ALA; Z is ##STR7## D is H or 1 or 2 substituents which increase or do not substantially decrease the acidity of the phenol proton; E is H or C 1 -C 3 loweralkyl; R 1 is OH, NHR", ##STR8## and R" and R'" are individually H or lower alkyl; provided that V may be D- or L-isomer if R is other than H, and further provided that no more than one of V, X, and Y is a D amino acid.
Claim 3
Dependent Claim
120 words
A peptide having the formula: R--V--W--X--Y--Z--R.sup.1 or a pharmaceutically acceptable acid- or base-addition salt thereof, wherein: R--V is acyl-ARG or acyl-D-ARG; W is PRO or AIB X is D-ASP, ASP, D-GLU, or GLU; Y is GLY, VAL, LEU, norLEU, PHE, ILE, LYS, GLN, GLU, ALA, D-VAL, D-LEU, D-norLEU, D-PHE, D-ILE, D-LYS, D-GLN, D-GLU, or D-ALA; Z is ##STR9## D is H or 1 or 2 substituents which increase or do not substantially decrease the acidity of the phenol proton; E is H or C 1 -C 3 loweralkyl; R 1 is OH, NHR", ##STR10## and R" and R'" are individually H or lower alkyl; provided that no more than one of V, X, and Y is a D amino acid.
Claim 4
Dependent Claim
120 words
A peptide having the formula: R--V--W--X--Y--Z--R.sup.1 or a pharmaceutically acceptable acid- or base-addition salt thereof, wherein: R--V is acyl-ARG or acyl-D-ARG; W is PRO or AIB X is D-ASP, ASP, D-GLU, or GLU; Y is GLY, VAL, LEU, norLEU, PHE, ILE, LYS, GLN, GLU, ALA, D-VAL, D-LEU, D-norLEU, D-PHE, D-ILE, D-LYS, D-GLN, D-GLU, or D-ALA; Z is ##STR9## D is H or 1 or 2 substituents which increase or do not substantially decrease the acidity of the phenol proton; E is H or C 1 -C 3 loweralkyl; R 1 is OH, NHR", ##STR10## and R" and R'" are individually H or lower alkyl; provided that no more than one of V, X, and Y is a D amino acid.
Claim 5
Dependent Claim
78 words
A peptide having the formula: R--V--W--X--Y--Z--R.sup.1 or a pharmaceutically acceptable acid- or base-addition salt thereof, wherein: R--V is acyl-ARG; W is PRO or AIB; X is ASP or GLU; Y is GLY, VAL, LEU, norLEU, PHE, ILE, LYS, GLN, GLU, or ALA; Z is ##STR11## D is H or 1 or 2 substituents which increase the acidity of the phenol proton; E is H or C 1 -C 3 loweralkyl; R 1 is OH or NH 2 .
Claim 6
Dependent Claim
78 words
A peptide having the formula: R--V--W--X--Y--Z--R.sup.1 or a pharmaceutically acceptable acid- or base-addition salt thereof, wherein: R--V is acyl-ARG; W is PRO or AIB; X is ASP or GLU; Y is GLY, VAL, LEU, norLEU, PHE, ILE, LYS, GLN, GLU, or ALA; Z is ##STR11## D is H or 1 or 2 substituents which increase the acidity of the phenol proton; E is H or C 1 -C 3 loweralkyl; R 1 is OH or NH 2 .
Claim 7
Dependent Claim
16 words
The peptide of claim 3 wherein R--V is acetyl-ARG and R 1 is NH 2 .
Claim 8
Dependent Claim
10 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP-VAL-TYR-NH 2 .
Claim 9
Dependent Claim
8 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP-GLU-TYR-OH.
Claim 10
Dependent Claim
8 words
The peptide of claim 3 which is N-α-succinoyl-ARG-PRO-ASP-VAL-TYR-OH.
Claim 11
Dependent Claim
8 words
The peptide of claim 3 which is N-α-formyl-ARG-PRO-ASP-VAL-TYR-OH.
Claim 12
Dependent Claim
8 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP-ILE-TYR-OH.
Claim 13
Dependent Claim
8 words
The peptide of claim 2 which is N-α-acetyl-D-ARG-PRO-ASP-VAL-TYR-OH.
Claim 14
Dependent Claim
8 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP-PHE-TYR-OH.
Claim 15
Dependent Claim
8 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP-GLN-TYR-OH.
Claim 16
Dependent Claim
8 words
The peptide of claim 2 which is N-α-acetyl-ARG-PRO-ASP-VAL-D-TYR-OH.
Claim 17
Dependent Claim
9 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP- VAL-TYR-OH.
Claim 18
Dependent Claim
10 words
The peptide of claim 1 which is NH 2 -ARG-D-PRO-ASP-VAL-TYR-OH.
Claim 19
Dependent Claim
8 words
The peptide of claim 2 which is ##STR12##
Claim 20
Dependent Claim
8 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP-ALA-TYR-OH.
Claim 21
Dependent Claim
10 words
The peptide of claim 2 which is N-α-acetyl-ARG-PRO-ASP-VAL-TYR-NH-CH 3 .
Claim 22
Dependent Claim
10 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-GLU-VAL-TYR-NH 2 .
Claim 23
Dependent Claim
10 words
The peptide of claim 2 which is N-α-acetyl-D-ARG-PRO-ASP-VAL-TYR-NH 2 .
Claim 24
Dependent Claim
10 words
The peptide of claim 2 which is N-α-acetyl-ARG-AIB-ASP-VAL-TYR-NH 2 .
Claim 25
Dependent Claim
10 words
The peptide of claim 1 which is N-α-acetyl-ARG-3,4-dehydro-PRO-ASP-VAL-TYR-NH 2 .
Claim 26
Dependent Claim
12 words
The peptide of claim 1 which is NH 2 -ARG-PRO-ASP-VAL-TYR-NH 2 .
Claim 27
Dependent Claim
8 words
The peptide of claim 3 which is N-α-acetyl-ARG-AIB-ASP-VAL-TYR-OH.
Claim 28
Dependent Claim
10 words
The peptide of claim 1 which is NH 2 -ARG-CLE-ASP-VAL-TYR-OH.
Claim 29
Dependent Claim
10 words
The peptide of claim 1 which is N-α-acetyl-ARG-PRO-ASP-VAL-TYR-GLY-NH 2 .
Claim 30
Dependent Claim
8 words
The peptide of claim 3 which is N-α-acetyl-ARG-PRO-ASP-VAL-N-α-methyl-TYR-OH.
Claim 31
Dependent Claim
10 words
The peptide of claim 1 which is NH 2 -ARG-4-methyl-LEU-ASP-VAL-TYR-OH.
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) | 1988-03-18 | 1988-09-17 | 1989-03-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-03-18 | 1992-09-17 | 1993-03-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-03-18 | 1996-09-17 | 1997-03-19 | $7700.00 | Window Closed / Lapsed |