# US 6,051,683 A · Immune regulating peptides and method of obtaining them

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- Number: US 6,051,683 A
- Document ID: US6051683A
- Status: Granted
- Kind: A
- Application number: 08/894,963
- Filed: 1998-08-17
- Granted: 2000-04-18
- Earliest claimed: 1995-03-02
- Assignees: Immunotech Developments Inc.
- Inventors: Vladislav Isakovich Deigin; Andrei Marxovich Korotkov
- Web page: https://patentgrep.com/patent/US6051683A

## CPC

- C07K 5/0821: {with the first amino acid being heterocyclic, e.g. His, Pro, Trp}
- A61P 37/02: Immunomodulators
- C07K 5/0205: {containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof}
- C07K 5/021: {containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds}
- C07K 5/06104: {with the first amino acid being acidic}
- C07K 5/0804: {and aliphatic}
- C07K 5/0812: {and aromatic or cycloaliphatic}
- C07K 5/0815: {with the first amino acid being basic}
- C07K 5/0819: {with the first amino acid being acidic}
- C07K 5/0823: {and Pro-amino acid; Derivatives thereof}
- C07K 5/1005: {and aliphatic}
- C07K 5/1016: {and aromatic or cycloaliphatic}
- C07K 5/1021: {with the first amino acid being acidic}
- C07K 5/1024: {with the first amino acid being heterocyclic}
- A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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

The invention relates to medicine, specifically, to methods of obtaining biologically active substances with immuno-regulating properties, and can be used in medicine and veterinary science and in experimental biochemistry. The fundamental problem addressed by the invention is that of producing a noval synthetic biologically active peptide with immuno-regulating properties and of the formula: X-Glu-Trp-Y, in which X is H or Gly, Ala, Leu, Ile, Val, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, .gamma.-aminobutyric acid, .zeta.-aminocapronic acid; Y is Gla, Ala, Leu, Ile, Val, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, .gamma.-aminobutyric acid .zeta.-aminocapronic acid, --OH, NH.sub.2,N.sub.2 H.sub.3, mono- or di-substituted amide (C.sub.1 -C.sub.3). Peptide synthesis takes place in a solution by successive growth of a chain from the C termination of the molecules, using a strategy of maximum blocking of functional groups, starting from amino acid alkyl ether, using the method of activating the ethers and the method of mixed anhydrides using tributyloxicarbonyl amino acid, with the proviso when X is H, Y is not OH.

## Claims

### Claim 1

A peptide of the formula I
X-Glu-Trp-Y, I
wherein X is H, Gly, Ala, Leu, Ile, Val, NVal, Pro, Try, Phe, Trp, D-Ala, D-Leu, D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, His, Lys, Arg, .gamma.-aminobutyric acid, or .zeta.-aminocaproic acid; Y is Gly, Ala, Leu, Ile, Val, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, Arg, .gamma.-aminobutyric acid, .zeta.-aminocaproic acid, --OH, NH.sub.2, N.sub.2 H.sub.3, or a mono- or di-substituted amide (C.sub.1 -C.sub.3); with the proviso that when X is H, Y is not OH.

### Claim 2

A peptide consisting of the sequence H-Ile-Glu-Trp-OH, His-Glu-Trp-OH, H-Glu-Trp-NH.sub.2, H-Glu-Trp-Arg, Lys-Glu-Trp-OH, Arg-Glu-Trp-OH, H-Glu-Trp-Tyr, Lys-Glu-Trp-Tyr, H-Glu-Trp-N.sub.2 H.sub.3, H-Glu-Trp-Gly, or Val-Glu-Trp-OH.

### Claim 3

A peptide consisting of the sequence H-Ile-Glu-Trp-OH.

### Claim 4 (depends on 1)

A pharmaceutical composition comprising at least one peptide of the formula I as claimed in claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A method for modulating immune system response of a subject comprising administering to a subject an amount effective for modulating immune system response of a peptide of the formula I as claimed in claim 1 in an amount effective for modulating said immune system response.

### Claim 6 (depends on 3)

A pharmacological composition comprising the peptide of claim 3 and the pharmaceutically acceptable carrier.

### Claim 7 (depends on 3)

A method for stimulating the immune system of a subject comprising administering to the subject an immune stimulating effective amount of the peptide of claim 3.