# US 6,168,784 A · N-terminal modifications of RANTES and methods of use

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- Number: US 6,168,784 A
- Document ID: US6168784A
- Status: Granted
- Kind: A
- Application number: 09/141,833
- Filed: 1998-08-28
- Granted: 2001-01-02
- Earliest claimed: 1997-09-03
- Assignees: Gryphon Sciences
- Inventors: Robin E. Offord; Darren Thompson; Jill Wilken
- Web page: https://patentgrep.com/patent/US6168784A

## CPC

- C07K 14/523: {Beta-chemokines, e.g. RANTES, I-309/TCA-3, MIP-1alpha, MIP-1beta/ACT-2/LD78/SCIF, MCP-1/MCAF, MCP-2, MCP-3, LDCF-1, LDCF-2}
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 17/00: Drugs for dermatological disorders
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/18: for HIV
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- 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

N-terminally modified RANTES derivatives are disclosed. The derivatives effectively block the inflammatory effects of RANTES, and are useful for the treatment of asthma, allergic rhinitis, atopic dermatitis, atheroma/atherosclerosis, and rheumatoid arthritis. Additionally, the compounds are useful for the treatment of HIV infection.

## Claims

### Claim 1

A compound of the formula:
R1-RANTES (2-68) (SEQ ID NO:2)
where R1 is CH3—(CH2)n—X—; in which
X is —C(O)—NH—CH2—C(O)—, —NHCH2—C(O)—, —ONH—CH2—C(O)—, —OCH2—CH2—C(O)—, —CH═CH—C(O)—, —C(O)—, or a covalent bond; and
n is an integer of 4-8;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein n is 4 and X is —C(O)—NH—CH2—C(O)—.

### Claim 3 (depends on 1)

The compound of claim 1, wherein n is 5 and X is —NH—CH2—C(O)—.

### Claim 4 (depends on 1)

The compound of claim 1, wherein n is 7 and X is —C(O)—.

### Claim 5 (depends on 1)

The compound of claim 1, wherein n is 8 and X is a covalent bond.

### Claim 6 (depends on 1)

The compound of claim 1, wherein n is 4 and X is —ONH—CH2—C(O)—.

### Claim 7 (depends on 1)

The compound of claim 1, wherein n is 5 and X is —CH═CH—C(O)—.

### Claim 8 (depends on 1)

The compound of claim 1, wherein n is 4 and X is —OCH2—CH2—C(O)—.

### Claim 9

A composition which comprises of a compound of the formula:
R1-RANTES (2-68)
where R1 is CH3—(CH2)n—X—; in which
X is —C(O)—NH—CH2—C(O)—, —NHCH2—C(O)—, —ONH—CH2—C(O)—, —OCH2—CH2—C(O)—, —CH═CH—C(O)—, —C(O)—, or a covalent bond; and
n is an integer of 4-8;
or a pharmaceutically acceptable salt thereof; in admixture with one or more pharmaceutically acceptable excipients.