# US 11,433,082 B2 · Composition containing sulfoalkyl ether cyclodextrin and latanoprost

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- Number: US 11,433,082 B2
- Document ID: US11433082B2
- Status: Granted
- Kind: B2
- Application number: 16/672,170
- Filed: 2019-11-01
- Published: 2020-06-11
- Granted: 2022-09-06
- Earliest claimed: 2019-11-01
- Assignees: CyDex Pharmaceuticals, Inc.
- Applicants: CyDex Pharmaceuticals, Inc.
- Inventors: Naomi Esaki; James D. Pipkin
- Web page: https://patentgrep.com/patent/US11433082B2

## CPC

- A61K 31/557: Eicosanoids, e.g. leukotrienes {or prostaglandins}
- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 31/74: Synthetic polymeric materials
- A61K 47/40: Cyclodextrins; Derivatives thereof
- A61P 27/02: Ophthalmic agents
- 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

## Abstract

An aqueous composition of latanoprost and SAE-CD is provided. The composition possesses improved stability over otherwise similar compositions excluding SAE-CD. Methods of and systems for treating disease, disorders, conditions or symptoms of the eye that are therapeutically responsive to latanoprost are also provided.

## Claims

### Claim 1

An aqueous composition comprising: aqueous carrier; SAE-β-CD; and latanoprost, wherein the pH of the composition ranges from 6.6 to 7, and wherein the composition does not comprise hyaluronate.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the molar ratio of SAE-β-CD to latanoprost ranges from 2:1 to 40:1.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the molar ratio of SAE-β-CD to latanoprost ranges from 4:1 to 21:1.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the concentration of latanoprost ranges from 10 to 500 μg/mL.

### Claim 5 (depends on 4)

The composition of claim 4, wherein the concentration of latanoprost ranges from 25 to 150 μg/mL.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the concentration of SAE-β-CD ranges from 1 to 100 mg/mL.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the concentration of SAE-β-CD ranges from 1 to 50 mg/mL.

### Claim 8 (depends on 1)

The aqueous composition of claim 1, wherein at least 98% wt. of the latanoprost is dissolved in the composition.

### Claim 9 (depends on 1)

The aqueous composition of claim 1, wherein the composition is a liquid, syrup, cream or gel.

### Claim 10 (depends on 1)

The aqueous composition of claim 1, wherein a dose of latanoprost comprises a therapeutically effective amount thereof in a volume of composition of 15 to 150 μL.

### Claim 11 (depends on 1)

The aqueous composition of claim 1, wherein SAE-β-CD comprises a compound, or mixture of compounds, of the Formula 1:
wherein:
p is 5;
R1 is independently selected at each occurrence from —OH or -SAET;
-SAE is a —O—(C2-C6 alkylene)-SO3− group, wherein at least one SAE is independently a —O—(C2-C6 alkylene)-SO3— group, a —O—(CH2)gSO3− group, wherein g is 2 to 6; and
T is independently selected at each occurrence from the group consisting of pharmaceutically acceptable cations, provided that at least one R1 is a hydroxyl moiety and at least one R1 is -SAET.

### Claim 12 (depends on 11)

The aqueous composition of claim 11, wherein average degree of substitution for the SAE-β-CD ranges from 5 to 7.

### Claim 13 (depends on 11)

The aqueous composition of claim 11, wherein g is 2 to 4.

### Claim 14 (depends on 1)

The aqueous composition of claim 1, wherein the aqueous carrier is selected from water, aqueous alcohol, aqueous organic solvent, or any combinations thereof.

### Claim 15 (depends on 1)

The composition of claim 1, wherein the composition does not comprise a preservative.

### Claim 16 (depends on 1)

The composition of claim 1, wherein the composition does not comprise benzalkonium chloride.

### Claim 17 (depends on 1)

A system for treating a disease, disorder, condition or symptom of the eye in a subject in need thereof, the system comprising:
the aqueous composition of claim 1; and
an administration device for ophthalmic administration of the aqueous composition to the subject, wherein the composition is provided in the device.

### Claim 18 (depends on 17)

The system according to claim 17, wherein the administration device is a dropper, drop-dispensing package, tube, eye spray device, or eye wash unit.

### Claim 19 (depends on 17)

The system according to claim 17, wherein the administration device comprises plural unit doses of latanoprost.

### Claim 20

A unit dose of an aqueous composition comprising:
aqueous carrier;
SAE-β-CD;
latanoprost; and
potassium sorbate;
wherein the concentration of latanoprost is about 50 μg/mL; the concentration of the potassium sorbate is about 0.05 to about 0.2% by weight of the unit dose; and wherein the solution is suitable for ophthalmic administration to a subject in need thereof;
wherein the composition does not comprise hyaluronate; and
wherein the pH of the composition ranges from 6.6 to 7.

### Claim 21 (depends on 20)

The unit dose of claim 20, wherein the molar ratio of SAE-β-CD to latanoprost ranges from 2:1 to 40:1.

### Claim 22 (depends on 21)

The unit dose of claim 21, wherein the molar ratio of SAE-β-CD to latanoprost ranges from 4:1 to 21:1.

### Claim 23 (depends on 20)

The unit dose of claim 20, wherein the concentration of latanoprost ranges from 10 to 500 μg/mL.

### Claim 24 (depends on 23)

The unit dose of claim 23, wherein the concentration of latanoprost ranges from 25 to 150 μg/mL.

### Claim 25 (depends on 20)

The unit dose of claim 20, wherein the concentration of SAE-β-CD ranges from 1 to 100 mg/mL.

### Claim 26 (depends on 25)

The unit dose of claim 25, wherein the concentration of SAE-β-CD ranges from 1 to 50 mg/mL.

### Claim 27 (depends on 20)

The unit dose of claim 20, wherein at least 98% wt. of the latanoprost is dissolved in the composition.

### Claim 28 (depends on 20)

The unit dose of claim 20, wherein the composition is a liquid, syrup, cream or gel.

### Claim 29 (depends on 20)

The unit dose of claim 20, wherein a dose of latanoprost comprises a therapeutically effective amount thereof in a volume of composition of 15 to 150 μL.

### Claim 30 (depends on 20)

The unit dose of claim 20, wherein SAE-β-CD comprises a compound, or mixture of compounds, of the Formula 1:
wherein:
p is 5;
R1 is independently selected at each occurrence from —OH or -SAET;
-SAE is a —O—(C2-C6 alkylene)-SO3− group, wherein at least one SAE is independently a —O—(C2-C6 alkylene)-SO3− group, a —O—(CH2)gSO− group, wherein g is 2 to 6; and
T is independently selected at each occurrence from the group consisting of pharmaceutically acceptable cations, provided that at least one R1 is a hydroxyl moiety and at least one R1 is -SAET.

### Claim 31 (depends on 30)

The unit dose of claim 30, wherein average degree of substitution for the SAE-β-CD ranges from 5 to 7.

### Claim 32 (depends on 30)

The unit dose of claim 30, wherein g is 2 to 4.

### Claim 33 (depends on 30)

The unit dose of claim 30, wherein the aqueous carrier is selected from water, aqueous alcohol, aqueous organic solvent, or any combinations thereof.

### Claim 34

An aqueous composition comprising:
aqueous carrier;
SAE-β-CD,
latanoprost; and
one or more agents selected from one or more viscosity modifiers, one or more tonicity modifiers, one or more buffering agents, one or more buffers, one or more suspending agents, one or more gelling agents, or a combination thereof;
wherein the composition is preservative-free; and
wherein the pH of the composition ranges from 6.6 to 7.

### Claim 35 (depends on 34)

The composition of claim 34, wherein the molar ratio of SAE-β-CD to latanoprost ranges from 2:1 to 40:1.

### Claim 36 (depends on 35)

The composition of claim 35, wherein the molar ratio of SAE-β-CD to latanoprost ranges from 4:1 to 21:1.

### Claim 37 (depends on 34)

The composition of claim 34, wherein the concentration of latanoprost ranges from 25 to 150 μg/mL.

### Claim 38 (depends on 37)

The composition of claim 37, wherein the concentration of SAE-β-CD ranges from 1 to 50 mg/mL.

### Claim 39 (depends on 34)

The composition of claim 34, wherein the viscosity of the composition is in the range of 1-20,000 cps.

### Claim 40 (depends on 39)

The composition of claim 39, wherein the viscosity of the composition is less than 1000 cps.

### Claim 41 (depends on 34)

The composition of claim 34, wherein SAE-β-CD comprises a compound, or mixture of compounds, of the Formula 1:
wherein:
p is 5;
R1 is independently selected at each occurrence from —OH or -SAET;
-SAE is a —O—(C2-C6 alkylene)-SO3− group, wherein at least one SAE is independently a —O—(C2-C6 alkylene)-SO3− group, a —O—(CH2)gSO− group, wherein g is 2 to 6; and
T is independently selected at each occurrence from the group consisting of pharmaceutically acceptable cations, provided that at least one R1 is a hydroxyl moiety and at least one R1 is -SAET.

### Claim 42 (depends on 41)

The composition of claim 41, wherein average degree of substitution for the SAE-β-CD ranges from 5 to 7.

### Claim 43 (depends on 41)

The composition of claim 41, wherein g is 2 to 4.

### Claim 44 (depends on 34)

The composition of claim 34, wherein the aqueous carrier is selected from water, aqueous alcohol, aqueous organic solvent, or any combinations thereof.