# US 7,745,547 B1 · Multi-arm cyclic or cubic siloxane-based formulations for drug delivery

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- Number: US 7,745,547 B1
- Document ID: US7745547B1
- Status: Granted
- Kind: B1
- Application number: 11/500,175
- Filed: 2006-08-07
- Granted: 2010-06-29
- Earliest claimed: 2005-08-05
- Assignees: Becton, Dickinson and Company; Research Foundation of the City University of NY
- Inventors: Andrew Auerbach; Bhanu P. S. Chauhan; Richard P. Clarke; M. Ishaq Haider; Umar Latif
- Web page: https://patentgrep.com/patent/US7745547B1

## CPC

- C08G 65/336: containing silicon
- A61K 47/52: the modifying agent being an inorganic compound, e.g. an inorganic ion that is complexed with the active ingredient
- A61K 47/60: the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
- C08L 2203/02: for biomedical use
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention provides multi-arm siloxane-based molecules suitable for use as a drug delivery vehicle comprising a central core molecule that comprises a cyclic or cubic siloxane, and a plurality of arms attached to the central core molecule, wherein each arm comprises an organic moiety. The multi-arm siloxane-based molecules described herein are suitable for encapsulation of a therapeutic agent. The invention further includes pharmaceutical compositions comprising the claimed multi-arm siloxane-based molecules and an encapsulated therapeutic agent in combination with a pharmaceutically acceptable carrier. Methods of making and using the multi-arm siloxane-based molecules are also provided.

## Claims

### Claim 1

A multi-arm siloxane-based molecule for use as a drug delivery vehicle comprising a central core molecule that comprises a cyclic siloxane and a plurality of arms attached to the central core molecule, wherein each arm comprises an organic moiety, and wherein one or more of insulin, cisplatin, or paclitaxel is encapsulated in the molecule.

### Claim 2 (depends on 1)

The multi-arm siloxane-based molecule of claim 1, wherein the central core molecule is tetramethylcyclotetrasiloxane or pentamethylcyclopentasiloxane.

### Claim 3 (depends on 1)

The multi-arm siloxane-based molecule of claim 1, wherein the central core molecule is attached to about 3 to about 10 arms.

### Claim 4 (depends on 3)

The multi-arm siloxane-based molecule of claim 3, wherein the central core molecule is attached to about 4 to about 8 arms.

### Claim 5 (depends on 1)

The multi-arm siloxane-based molecule of claim 1, wherein the organic moiety of each arm comprises a polyethylene glycol (PEG).

### Claim 6 (depends on 5)

The multi-arm siloxane-based molecule of claim 5, wherein the PEG has a molecular weight of about 400 Da to about 1500 Da.

### Claim 7 (depends on 5)

The multi-arm siloxane-based molecule of claim 5, wherein the PEG has a molecular weight of about 400 Da.

### Claim 8 (depends on 5)

The multi-arm siloxane-based molecule of claim 5, wherein the PEG has a molecular weight of about 1000 Da.

### Claim 9 (depends on 5)

The multi-arm siloxane-based molecule of claim 5, wherein the PEG is selected from the group consisting of PEG-tetrahydrofurfuryl ether, PEG-methyl ether 350, and PEG-methyl ether 550.

### Claim 10 (depends on 1)

The multi-arm siloxane-based molecule of claim 1, wherein the molecule is selected from the group consisting of (PEG400)4D4M, (PEG1000)4D4M, (PEG400)5D5M, (PEG-THF ether)4D4M, DA4D4M, BE4D4M, [PEGMetEt(350)]4D4M, and [PEGMetEt(550)]4D4M.

### Claim 11 (depends on 1)

A composition comprising a plurality of the multi-arm siloxane-based molecule of claim 1.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the plurality of multi-arm siloxane based molecules form a micellar structure in a solution.

### Claim 13 (depends on 1)

A pharmaceutical composition comprising the multi-arm siloxane-based molecule of claim 1 and a pharmaceutically acceptable carrier.

### Claim 14

A pharmaceutical composition comprising:
a multi-arm siloxane-based molecule for use as a drug delivery vehicle comprising a central core molecule that comprises a cyclic siloxane and a plurality of arms attached to the central core molecule, wherein each arm comprises a PEG selected from the group consisting of PEG-tetrahydrofurfuryl ether, PEG-methyl ether 350, and PEG-methyl ether 550;
a therapeutic agent selected from the group consisting of anticancer agents, diabetes-controlling agents, antibiotics, antifungal agents, antiviral agents, anti-inflammatory drugs, migraine drugs, anti-anxiety agents, hormones, growth factors, steroidal agents, cardiovascular agents, and combinations thereof; and
a pharmaceutically acceptable carrier.

### Claim 15 (depends on 14)

The multi-arm siloxane-based molecule of claim 14, wherein the central core molecule is tetramethylcyclotetrasiloxane or pentamethylcyclopentasiloxane.

### Claim 16 (depends on 14)

The multi-arm siloxane-based molecule of claim 14, wherein the central core molecule is attached to about 3 to about 10 arms.

### Claim 17 (depends on 14)

The multi-arm siloxane-based molecule of claim 14, wherein the central core molecule is attached to about 4 to about 8 arms.

### Claim 18 (depends on 14)

A composition comprising a plurality of the multi-arm siloxane-based molecule of claim 14.

### Claim 19 (depends on 14)

A pharmaceutical composition comprising the multi-arm siloxane-based molecule of claim 14 having at least one therapeutic went encapsulated within the molecule and a pharmaceutically acceptable carrier.

### Claim 20

A pharmaceutical composition comprising
a plurality of siloxane-based molecules for use as a drug delivery vehicle comprising a central core molecule that comprises a cyclic siloxane and a plurality of arms attached to the central core molecule, wherein each arm comprises an organic moiety, wherein the plurality of multi-arm siloxane based molecules forms a micellar structure in a solution;
a therapeutic agent selected from the group consisting of anticancer agents, diabetes-controlling agents, antibiotics, antifungal agents, antiviral agents, anti-inflammatory drugs, migraine drugs, anti-anxiety agents, hormones, steroidal agents, cardiovascular agents, and combinations thereof; and
a pharmaceutically acceptable carrier.
