# US 6,103,699 A · Peptide, a method for its preparation and a pharmaceutical composition containing the peptide

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- Number: US 6,103,699 A
- Document ID: US6103699A
- Status: Granted
- Kind: A
- Application number: 09/032,550
- Filed: 1998-02-26
- Granted: 2000-08-15
- Earliest claimed: 1996-06-07
- Assignees: Immunotech Developments Inc.
- Inventors: Vladislav I. Deigin; Andrei Marxovich Korotkov
- Web page: https://patentgrep.com/patent/US6103699A

## CPC

- C07K 5/0215: {containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu}
- A61K 38/06: Tripeptides
- A61K 38/07: Tetrapeptides
- A61K 38/08: Peptides having 5 to 11 amino acids {(A61K38/043 - A61K38/046 take precedence)}
- C07K 5/0806: {the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala}
- C07K 5/0808: {the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu}
- C07K 5/0812: {and aromatic or cycloaliphatic}
- C07K 5/0819: {with the first amino acid being acidic}
- C07K 5/0821: {with the first amino acid being heterocyclic, e.g. His, Pro, Trp}
- C07K 5/0823: {and Pro-amino acid; Derivatives thereof}
- C07K 5/1008: {the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala}
- C07K 5/101: {the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu}
- C07K 5/1016: {and aromatic or cycloaliphatic}
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

A peptide of the formula I X--A--D--Trp--Y wherein X is hydrogen, glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tryptophan, .gamma.-aminobutyric acid or .xi.-aminocaproic acid; A is D-gluptamic acid or D-iso-glutamic acid; and Y is glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tryptophn, .gamma.-aminobutyric acid, .xi.-aminocaproic acid, hydroxyl, or an amide group.

## Claims

### Claim 1

A method of inhibiting cell proliferation comprising administering an effective amount of a peptide of the formula I:
X--A--D--Trp--Y (I)
wherein X is selected from the group comprising hydrogen, glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tryptophan, .gamma.-aminobutyric acid, and .xi.-aminocaproic acid; A is selected from the group comprising D-glutamic acid and D-iso-glutamic acid; and Y is selected from the group comprising glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tyrptophan, .gamma.-aminobutyric acid, .xi.-aminocaproic acid, hydroxyl and an amide group, to a person or cell in need thereof.

### Claim 2 (depends on 1)

A method according to claim 1 wherein X is hydrogen, A is D-i-glutamic acid, and Y is selected from the group consisting of hydroxyl and an amide group substituted with a C1-C3 alkyl group.

### Claim 3 (depends on 1)

A method according to claim 1 wherein the peptide has the sequence H-D-iGlu-Trp-OH.

### Claim 4 (depends on 1)

A method according to claim 1 wherein the peptide is administered in a dose from about 1 .mu.g to about 10 g per kilogram of weight of the patient.

### Claim 5 (depends on 1)

A method according to claim 1 wherein the peptide is administered in dose from about 0.1 g to about 10 g per kilogram of weight of the patient.

### Claim 6 (depends on 1)

A method according to claim 1 wherein cell proliferation is hematopoietic cell proliferation.

### Claim 7 (depends on 1)

A method according to claim 1 wherein cell proliferation is immune system cell proliferation.