# US 8,772,227 B2 · Glucosamine pro-drug

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- Number: US 8,772,227 B2
- Document ID: US8772227B2
- Status: Granted
- Kind: B2
- Application number: 13/622,516
- Filed: 2012-09-19
- Published: 2013-08-01
- Granted: 2014-07-08
- Earliest claimed: 2011-03-02
- Applicants: Fahkreddin Jamali; Kamalijit Kaur; Mohammadhossien Gilzad
- Inventors: Fahkreddin Jamali; Kamalijit Kaur; Mohammadhossien Gilzad
- Web page: https://patentgrep.com/patent/US8772227B2

## CPC

- A61K 47/64: Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent (peptidic linkers A61K47/65)
- A61K 47/542: {Carboxylic acids, e.g. a fatty acid or an amino acid}
- 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

To develop glucosamine (GlcN) pro-drugs with properties superior to the presently available GlcN products, we have synthesized derivatives with improved pharmaceutical properties. The synthesized derivatives include peptide-GlcN ester and amide conjugates where the peptide portion consists of one or more amino acids. One such compound is (5-amino-3,4,6-trihydroxyoxan-2-yl)methyl 2-(2-aminoacetamido)-3-methylbutanoate or glycine-valine-COO-GlcN (GV-GlcN).7.

## Claims

### Claim 1

A composition comprising a pharmaceutically acceptable salt or base of compounds chemically containing glucosamine (GlcN) with one or more amino acids attached at the amino or alcohol groups to form amide or ester of the amino-sugar with no ether linkage, wherein said compound is selected from the group consisting of a pharmaceutically accepted salt or base of (5-amino-3,4,6-trihydroxyoxan-2-yl)methyl 2-(2-aminoacetamido)-3-methylbutanoate; a pharmaceutically accepted salt or base of glycine-valine-COO-GlcN (GV-GlcN); and combinations thereof.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1 wherein the acidic salts are hydrochloride and sulfate.

### Claim 3

A method of treating any disease or condition for which glucosamine has been previously prescribed comprising administering an effective amount of a glucosamine pro-drug comprising a pharmaceutically accepted salt or base of (5-amino-3,4,6-trihydroxyoxan-2-yl)methyl 2-(2-aminoacetamido)-3-methylbutanoate or a pharmaceutically accepted salt or base of glycine-valine-COO-GlcN (GV-GlcN); or combinations thereof.

### Claim 4 (depends on 3)

The method of claim 3 wherein the disease or condition is selected from the group consisting of osteoarthritis, rheumatoid arthritis, and adjuvant arthritis.