US4420424A
Expired / Lapsed
US
⏱️ 0.0 years remaining
New peptides and a process for their preparation
Assignee: Hoechst AG
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Filing: 1981-11-09
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Granted: 1983-12-13
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Expires: 2001-11-09
Abstract
Abstract What are disclosed are pentapeptides, useful for influencing the maturing of T-lymphocytes, of the formula G--K--Q--X--M wherein G is arginine, lysine, ornithine, or homoarginine, or is an unsubstituted or substituted ω-aminoalkanoyl, ω-guanidinoalkanoyl, or ω-dimethylaminoalkanoyl; K is a basic amino acid such as lysine, arginine, homoarginine, or ornithine; Q is L- or D-glutamic acid, d-aspartic acid, or D-α-aminoadipic acid; X is L-valine or L-isoleucine; and M is an L- or D-aminoacid having a hydrophobic side chain, or an ester or amide of such an acid.
Inventors
- 👤 Rolf Geiger
- 👤 Wolfgang Konig
- 👤 Gerd Johnscher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 07:18
CPC Classifications
C; C07; C07K; C07K14/00; C07K14/435; C07K14/575; C07K14/66; C07K14/662; A; A61; A61P; A61P37/00; A61K; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/18
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
185 words
A peptide of the formula G--K--Q--X--M wherein G is arginine, lysine, ornithine, or homoarginine, all in the L- or their D-configuration, or is unsubstituted ω-aminoalkanoyl, ω-guanidinoalkanoyl, or ω-dimethylaminoalkanoyl having 3-6 C atoms, or is such ω-aminoalkanoyl, ω-guanidinoalkanoyl, or ω-dimethylaminoalkanoyl substituted with an d amino group in the L- or D-configuration, which amino group in turn may carry alkanoyl having 1-6 C atoms, aroyl having 7-11 C atoms, cycloalkanoyl having up to 2 alkyl C atoms and 5-7 cycloalkyl C atoms, aralkanoyl having up to a total of 9 C atoms and wherein a --CH 2 -- group can be replaced by --O-- or --S--, alkoxycarbonyl or aralkyloxycarbonyl having up to 7 carbon atoms, or succinoyl, succinamoyl, glutaroyl, glutaminyl, pyroglutamyl, phthaloyl, phthalamidyl, or 2-carboxybenzoyl; K is a basic amino acid; Q is L- or D-glutamic acid, D-aspartic acid, or D-α-aminoadipic acid; X is L-valine or L-isoleucine; and M is an L- or D-aminoacid having a hydrophobic side chain, or is an ester, amide, alkylamide, or alkylester having 1-6 C atoms of such an acid, or is an aralkylester having 7-10 C atoms of such an acid.
Claim 2
Dependent Claim
185 words
A peptide of the formula G--K--Q--X--M wherein G is arginine, lysine, ornithine, or homoarginine, all in the L- or their D-configuration, or is unsubstituted ω-aminoalkanoyl, ω-guanidinoalkanoyl, or ω-dimethylaminoalkanoyl having 3-6 C atoms, or is such ω-aminoalkanoyl, ω-guanidinoalkanoyl, or ω-dimethylaminoalkanoyl substituted with an d amino group in the L- or D-configuration, which amino group in turn may carry alkanoyl having 1-6 C atoms, aroyl having 7-11 C atoms, cycloalkanoyl having up to 2 alkyl C atoms and 5-7 cycloalkyl C atoms, aralkanoyl having up to a total of 9 C atoms and wherein a --CH 2 -- group can be replaced by --O-- or --S--, alkoxycarbonyl or aralkyloxycarbonyl having up to 7 carbon atoms, or succinoyl, succinamoyl, glutaroyl, glutaminyl, pyroglutamyl, phthaloyl, phthalamidyl, or 2-carboxybenzoyl; K is a basic amino acid; Q is L- or D-glutamic acid, D-aspartic acid, or D-α-aminoadipic acid; X is L-valine or L-isoleucine; and M is an L- or D-aminoacid having a hydrophobic side chain, or is an ester, amide, alkylamide, or alkylester having 1-6 C atoms of such an acid, or is an aralkylester having 7-10 C atoms of such an acid.
Claim 3
Dependent Claim
14 words
A peptide as in claim 1 wherein K is L-lysine, L-arginine, L-homoarginine, or L-ornithine.
Claim 4
Dependent Claim
21 words
The method of influencing the maturing of thymus-dependent lymphocytes which comprises treating said lymphocytes with a peptide as in claim 1.
Claim 5
Dependent Claim
9 words
A peptide as in claim 1 which is Arg-Lys-Glu-Val-Tyr-OMe.
Claim 6
Dependent Claim
9 words
A peptide as in claim 1 which is D-Lys-Arg-Glu-Val-Tyr-OMe.
Claim 7
Dependent Claim
9 words
A peptide as in claim 1 which is Arg-Lys-D-Aad-Val-Tyr-OMe.
Claim 8
Dependent Claim
9 words
A peptide as in claim 1 which is Arg-Lys-D-Glu-Val-Tyr-OMe.
Claim 9
Dependent Claim
9 words
A peptide as in claim 1 which is Arg-Lys-Glu-Val-Trp-OMe.
Claim 10
Dependent Claim
107 words
A peptide as in claim 1 wherein K is L-lysine, L-arginine, L-homoarginine, or L-ornithine and M is an amino acid selected from the group consisting of Ala, Val, Leu, Ile, Met, Phe, Pro, Tyr, Phg (C-phenylglycine), Ser(Bu t ), Thr(Bu t ), Cys(Bu t ), Cys(Et), Cys(Bzl), Glu(OBu t ), Asp(OBu t ), Glu(NH-Bu t ), Glu(NH-Et), Lys(Z), Lys(Boc), Orn(Boc), Tyr(Bu t ), Tyr(Me), Phe(Cl), Tyr(Cl), tryptophan, and tryptophan substituted by alkyl, halogen, or methoxy, or is an amide, alkyl amide, or alkyl ester having 1-6 carbon atoms of such an amino acid, or is an aralkyl ester having 7-10 carbon atoms of such an amino acid.
Claim 11
Dependent Claim
10 words
A peptide as in claim 1 wherein Q is L-Glu.
Claim 12
Dependent Claim
13 words
A peptide as in claim 1 wherein Q is D-Glu, D-Asp, or D-Aad.
References Cited (Backward Citations)
US29595A
Cited
US124959A
Cited
FR2408580B1
Cited
FR2408581B1
Cited
GB1565032A
Cited
GB1585736A
Cited
US4261886A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-12-12 | 1987-06-13 | 1987-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-12 | 1991-06-13 | 1991-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-12 | 1995-06-13 | 1995-12-13 | $7700.00 | Window Closed / Lapsed |