# US 11,298,368 B2 · Efficient tobramycin compound conjugate compositions

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- Number: US 11,298,368 B2
- Document ID: US11298368B2
- Status: Granted
- Kind: B2
- Application number: 17/516,670
- Filed: 2021-11-01
- Published: 2022-02-24
- Granted: 2022-04-12
- Earliest claimed: 2020-05-22
- Assignees: Somerset Therapeutics, LLC
- Applicants: Somerset Therapeutics, LLC
- Inventors: Mandar V. Shah; Veerappan Subramanian; Ilango Subramanian
- Web page: https://patentgrep.com/patent/US11298368B2

## CPC

- A61K 31/7036: having at least one amino group directly attached to the carbocyclic ring, e.g. streptomycin, gentamycin, amikacin, validamycin, fortimicins
- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 31/573: substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/183: {Amino acids, e.g. glycine, EDTA or aspartame}
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 47/542: {Carboxylic acids, e.g. a fatty acid or an amino acid}
- A61K 47/545: {Heterocyclic compounds (A61K47/558 takes precedence)}
- A61K 47/58: obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K 47/60: the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
- A61P 27/02: Ophthalmic agents
- A61P 31/04: Antibacterial agents
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Disclosed herein are compositions comprising tobramycin or a tobramycin derivative that exhibit improvements in permeation of corneal cells, retention in corneal cells, or both. Such compositions can comprise tobramycin or tobramycin derivative(s) complexed to an agent which facilitates improved permeation of corneal cells, retention in corneal cells, or both. The invention also relates to a process of preparing such compositions.

## Claims

### Claim 1

A pharmaceutically acceptable composition for treating an infection caused by a bacteria in a mammalian eye comprising an effective amount of an ophthalmologically suitable complex, the complex comprising:
(a) tobramycin at 0.3-3% w/v and
(b) polyvinyl caprolactam-polyvinyl acetate-polyethylene glycol graft co-polymer (PCL-PVAc-PEG) at 0.3-3% w/v, wherein the PCL-PVAc-PEG forms a stable complex with tobramycin and the PCL-PVAc-PEG detectably promotes the uptake of tobramycin by corneal cells, the retention of tobramycin by corneal cells, or both, as compared to the free (noncomplexed) tobramycin.

### Claim 2 (depends on 1)

The pharmaceutically acceptable composition of claim 1, wherein the composition comprises tobramycin in an amount of about 1% w/v to about 3% w/v.

### Claim 3 (depends on 1)

The pharmaceutically acceptable composition of claim 1, wherein the composition comprises PCL-PVAc-PEG in an amount of about 1% w/v to about 3% w/v.

### Claim 4 (depends on 1)

The pharmaceutically acceptable composition of claim 1, wherein the composition is effective in treating the infection caused by the bacteria when administered no more than two times per day.

### Claim 5 (depends on 4)

The pharmaceutically acceptable composition of claim 4, wherein the composition is effective in treating the infection caused by the bacteria when administered no more than once per day.

### Claim 6 (depends on 4)

The pharmaceutically acceptable composition of claim 4, wherein the composition is provided as a solution, and a single administration comprises no more than two drops of the composition to the infected eye.

### Claim 7 (depends on 6)

The pharmaceutically acceptable composition of claim 6, wherein the composition is provided as a solution, and a single administration comprises no more than one drop of the composition to the infected eye.

### Claim 8 (depends on 5)

The pharmaceutically acceptable composition of claim 5, wherein the composition is provided as a solution, and a single administration comprises no more than two drops of the composition to the infected eye.

### Claim 9 (depends on 8)

The pharmaceutically acceptable composition of claim 8, wherein the composition is provided as a solution, and a single administration comprises no more than one drop of the composition to the infected eye.