# US 2014/0155494 A1 · Tri-molecular complexes and their use in drug delivery systems

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- Number: US 2014/0155494 A1
- Document ID: US20140155494A1
- Status: Published application
- Kind: A1
- Application number: 14/175,673
- Filed: 2014-02-07
- Published: 2014-06-05
- Earliest claimed: 2007-11-12
- Assignees: Pharmaceutics International, Inc.
- Applicants: Pharmaceutics International, Inc.
- Inventors: EmadEldin M. Hassan; Sridhar Gumudavelli
- Web page: https://patentgrep.com/patent/US20140155494A1

## CPC

- A61K 47/42: Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein (oligopeptides having up to five amino acids {A61K47/183}; polyamino acids A61K47/34)
- A61K 9/4858: {Organic compounds}
- A61K 9/4866: {Organic macromolecular compounds}
- 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

This invention relates to macromolecular complexes useful in drug delivery systems, specifically tri-molecular complexes made between a water-soluble polymer and an acid-insoluble polymer in presence of a bridging molecule. In one aspect, the invention relates to a tri-molecular complex comprising gelatin, acrylic acid/methacrylic acid copolymers, and arginine for use in a soft capsule dosage form. In another aspect, the invention is directed to a tri-molecular complex a hydrophilic, film-forming, water-soluble polymer, a second water-soluble polymer, and a bridging molecule, wherein the second water-soluble polymer is less water-soluble than the hydrophilic, film-forming, water-soluble polymer.

## Claims

### Claim 1

A tri-molecular complex for use in enteric drug delivery systems comprising:
(a) a hydrophilic, film-forming, water-soluble polymer;
(b) an acid-insoluble polymer; and
(c) an amino acid.

### Claim 2 (depends on 1)

The tri-molecular complex according to claim 1, further comprising an aqueous solvent.

### Claim 3 (depends on 1)

The tri-molecular complex according to claim 1, further comprising a plasticizer.

### Claim 4 (depends on 1)

The tri-molecular complex according to claim 1, wherein the amino acid is arginine.

### Claim 5 (depends on 1)

The tri-molecular complex according to claim 1, wherein the water-soluble polymer is gelatin, the acid-insoluble polymer is acrylate-methacrylate copolymers, and the amino acid is arginine.

### Claim 6 (depends on 3)

The tri-molecular complex according to claim 3, wherein the plasticizer is selected from the group consisting of glycerin, triethylcitrate, and mixtures thereof.

### Claim 7 (depends on 5)

The tri-molecular complex according to claim 5, wherein the amount of acrylate-methacrylate copolymers is at least about 25% by weight of the total amount of acrylate-methacrylate copolymers and gelatin.

### Claim 8 (depends on 6)

The tri-molecular complex according to claim 6, wherein the plasticizer is a mixture of glycerin and triethylcitrate.

### Claim 9 (depends on 5)

The tri-molecular complex according to claim 5, further comprising glycerin.

### Claim 10

A tri-molecular complex for use in controlling the release of a therapeutic or diagnostic agent comprising:
(a) a hydrophilic, film-forming, water-soluble polymer;
(b) acrylate-methacrylate copolymers; and
(c) a bridging molecule,
wherein the acrylate-methacrylate copolymers are less water-soluble than the hydrophilic, film-forming, water-soluble polymer.

### Claim 11 (depends on 1)

A method of preparing the tri-molecular complex according to claim 1 comprising the following steps: (1) suspending the acid-insoluble polymer in an acidic aqueous system with low buffer capacity; (2) mixing the water-soluble polymer with the amino acid; and (3) mixing the product of steps (1) and (2) to yield the tri-molecular complex.

### Claim 12

A tri-molecular complex for use in enteric drug delivery systems comprising:
(a) gelatin;
(b) acrylate-methacrylate copolymers; and
(c) arginine,
wherein the tri-molecular complex further comprises glycerin.

### Claim 13 (depends on 12)

The tri-molecular complex according to claim 12, wherein the amount of acrylate-methacrylate copolymers is at least about 25% by weight of the total amount of acrylate-methacrylate copolymers and gelatin.