# US 7,465,820 B2 · Abiotic heparin antagonists

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- Number: US 7,465,820 B2
- Document ID: US7465820B2
- Status: Granted
- Kind: B2
- Application number: 10/572,387
- Filed: 2004-09-16
- Published: 2007-04-12
- Granted: 2008-12-16
- Earliest claimed: 2003-09-19
- Assignees: Consiglio Nazionale Delle Ricerche
- Inventors: Francesca Cunsolo; Grazia Maria Letizia Consoli; Corrada Geraci; Tommaso Mecca
- Web page: https://patentgrep.com/patent/US7465820B2

## CPC

- C07C 237/04: the carbon skeleton being acyclic and saturated
- A61P 7/04: Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to heparin-binding calixarene compounds of general Formula (I) in which R, R1, L and n have the meanings indicated in the description and their use in the biomedical field.

## Claims

### Claim 1

A heparin-binding calixarene compound of formula (I):
wherein:
groups R are independently an amino acid acyl residue selected from the group consisting of: lysine, β-alanine, γ-amino-butyric acid, 6 -amino-hexanoic acid, 8-amino-octanoic acid, norleucine, and glycine;
R1 is hydrogen, straight or branched C1-C5 alkyl, or benzyl;
L is CH2, CH2OCH2 or S;
n is an integer ranging from 4 to 12; and
salts thereof with physiologically compatible acids.

### Claim 2 (depends on 1)

The heparin-binding calixarene compound according to claim 1, in which n is 8.

### Claim 3 (depends on 1)

The heparin-binding calixarene compound according to claim 1, in which L is CH2.

### Claim 4 (depends on 1)

The heparin-binding calixarene compound according to claim 1, in which R1 is propyl.

### Claim 5 (depends on 1)

The heparin-binding calixarene compound as claimed in claim 1, wherein:
groups R are independently the acyl residue of an amino acid selected from the group consisting of: lysine, β-alanine, γ-amino-butyric acid, 6-amino-hexanoic acid, 8-amino-octanoic acid, norleucine and glycine;
R1 is propyl;
L is CH2; and
n is 8.

### Claim 6 (depends on 5)

The heparin-binding calixarene compound as claimed in claim 5, in which the groups R are lysine acyl residues.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising the heparin-binding calixarene compound of claim 1 in admixture with suitable excipients and/or carriers.

### Claim 8 (depends on 1)

A method of preparing a pharmaceutical composition, said method comprising mixing the heparin-binding calixarene compound of claim 1 with a pharmaceutically acceptable excipient and/or carrier.

### Claim 9 (depends on 1)

A method of preparing a dialysis membrane, said method comprising contacting said dialysis membrane with the heparin-binding calixarene compound of claim 1.

### Claim 10 (depends on 1)

A method of treating biological fluids, said method comprising contacting the heparin-binding calixarene compound of claim 1 with a biological fluid in need of treatment thereof.

### Claim 11

A method of preparing a pharmaceutical composition, said method comprising mixing a pharmaceutically acceptable excipient and/or carrier with a heparin-binding calixarene compound of formula (I):
wherein:
groups R are independently hydrogen or an amino acid acyl residue selected from the group consisting of: lysine, β-alanine, γ-amino-butyric acid, 6-amino-hexanoic acid, 8-amino-octanoic acid, norleucine, and glycine;
R1 is hydrogen, straight or branched C1-C5 alkyl, or benzyl;
L is CH2, CH2OCH2 or S;
n is an integer ranging from 4 to 12; or
salts thereof with physiologically compatible acids.

### Claim 12

A method of preparing a dialysis membrane, said method comprising contacting said dialysis membrane with a heparin-binding calixarene compound of formula (I):
wherein:
groups R are independently hydrogen or an amino acid acyl residue selected from the group consisting of: lysine, β-alanine, γ-amino-butyric acid, 6amino-hexanoic acid, 8-amino-octanoic acid, norleucine, and glycine;
R1 is hydrogen, straight or branched C1-C5 alkyl, or benzyl;
L is CH2, CH2OCH2 or S;
n is an integer ranging from 4 to 12; or
salts thereof with physiologically compatible acids.

### Claim 13

A method of treating biological fluids, said method comprising contacting a biological fluid with a heparin-binding calixarene compound of formula (I):
wherein:
groups R are independently hydrogen or an amino acid acyl residue selected from the group consisting of: lysine, β-alanine, γ-amino-butyric acid , 6-amino-hexanoic acid, 8-amino-octanoic acid, norleucine, and glycine;
R1 is hydrogen, straight or branched C1-C5 alkyl, or benzyl;
L is CH2, CH2OCH2 or S;
n is an integer ranging from 4 to 12; or
salts thereof with physiologically compatible acids.