# US 9,750,822 B2 · Sulfoalkyl ether cyclodextrin compositions

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- Number: US 9,750,822 B2
- Document ID: US9750822B2
- Status: Granted
- Kind: B2
- Application number: 15/233,748
- Filed: 2016-08-10
- Published: 2016-12-01
- Granted: 2017-09-05
- Earliest claimed: 2008-04-28
- Assignees: CyDex Pharmaceuticals, Inc.
- Applicants: CyDex Pharmaceuticals, Inc.
- Inventors: Vincent D. Antle
- Web page: https://patentgrep.com/patent/US9750822B2

## CPC

- A61K 47/40: Cyclodextrins; Derivatives thereof
- A61K 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/58: containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin (digitoxin {A61K31/7048})
- A61K 31/724: Cyclodextrins
- A61K 47/61: the organic macromolecular compound being a polysaccharide or a derivative thereof
- A61K 47/6951: {using cyclodextrin (cyclodextrins used as simple excipients A61K47/40)}
- C08B 31/00: Preparation of derivatives of starch (derivatives of amylose C08B33/00; derivatives of amylopectin C08B35/00)
- C08B 37/0012: {Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof}
- C08L 5/16: Cyclodextrin; Derivatives thereof
- A61K 9/205: {Polysaccharides, e.g. alginate, gums; Cyclodextrin}
- 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)
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

SAE-CD compositions are provided, along with methods of making and using the same. The SAE-CD compositions comprise a sulfoalkyl ether cyclodextrin having an absorption of less than 0.5 A.U. due to a drug-degrading agent, as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 300 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

## Claims

### Claim 1

A sulfoalkyl ether cyclodextrin (SAE-CD) composition comprising a sulfoalkyl ether cyclodextrin having less than 200 ppm of a phosphate, wherein the SAE-CD composition has an absorption of less than 0.2 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 300 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 2 (depends on 1)

The SAE-CD composition of claim 1, wherein the SAE-CD composition has an absorption of less than 0.15 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 500 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 3 (depends on 1)

The SAE-CD composition of claim 1, wherein the SAE-CD composition has an absorption of less than 0.1 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 500 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 4 (depends on 1)

The SAE-CD composition of claim 1, wherein the SAE-CD composition has an absorption of less than 0.05 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 500 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 5 (depends on 1)

The SAE-CD composition of claim 1, wherein the SAE-CD is a compound of Formula (I):
wherein:
p is 4, 5, or 6; and
R1 is independently selected at each occurrence from —OH or —O—(C2-C6 alkylene)-SO3−-T, wherein T is independently selected at each occurrence from pharmaceutically acceptable cations, provided that at least one R1 is —OH and at least one R1 is —O—(C2-C6 alkylene)-SO3−-T.

### Claim 6 (depends on 5)

The SAE-CD composition of claim 5, wherein the SAE-CD has an average degree of substitution of 4.5 to 7.5.

### Claim 7 (depends on 5)

The SAE-CD composition of claim 5, wherein R1 is independently selected at each occurrence from —OH or —O—(C4 alkylene)-SO3−-T, and -T is Na+ at each occurrence.

### Claim 8 (depends on 5)

The SAE-CD composition of claim 5, wherein the SAE-CD is sulfobutyl ether β-cyclodextrin having the structure:
wherein:
each R is independently —H or —(CH2)4SO3Na; and
the average degree of substitution of —(CH2)4SO3Na is 6.0 to 7.1 per cyclodextrin molecule.

### Claim 9 (depends on 1)

The SAE-CD composition of claim 1 further comprising an active agent.

### Claim 10 (depends on 1)

The SAE-CD composition of claim 1, wherein the SAE-CD composition comprises:
less than 10 ppm of a sulfoalkylating agent;
less than 0.2% wt. of an underivatized cyclodextrin;
less than 0.5% wt. of an alkali metal halide salt; and
less than 0.1% wt. of a hydrolyzed sulfoalkylating agent.

### Claim 11 (depends on 1)

The SAE-CD composition of claim 1, wherein the SAE-CD composition comprises:
less than 250 ppb of a sulfoalkylating agent;
less than 0.1% wt. of an underivatized cyclodextrin;
less than 0.1% wt. of an alkali metal halide salt; and
less than 0.08% wt. of a hydrolyzed sulfoalkylating agent.

### Claim 12

A sulfoalkyl ether cyclodextrin (SAE-CD) composition comprising a sulfoalkyl ether cyclodextrin having less than 150 ppm of a phosphate, wherein the SAE-CD composition has an absorption of less than 0.2 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 300 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 13 (depends on 12)

The SAE-CD composition of claim 12, wherein the SAE-CD composition has an absorption of less than 0.2 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 500 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 14 (depends on 12)

The SAE-CD composition of claim 12, wherein the SAE-CD composition has an absorption of less than 0.15 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 500 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 15 (depends on 12)

The SAE-CD composition of claim 12, wherein the SAE-CD composition has an absorption of less than 0.1 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 500 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 16 (depends on 12)

The SAE-CD composition of claim 12, wherein the SAE-CD composition has an absorption of less than 0.05 A.U., as determined by UV/vis spectrophotometry at a wavelength of 245 nm to 270 nm for an aqueous solution containing 500 mg of the SAE-CD composition per mL of solution in a cell having a 1 cm path length.

### Claim 17 (depends on 12)

The SAE-CD composition of claim 12, wherein the sulfoalkyl ether cyclodextrin is a compound of Formula (I):
wherein:
p is 4, 5, or 6;
R1 is independently selected at each occurrence from —OH or —O—(C2-C6 alkylene)-SO3−-T, wherein T is independently selected at each occurrence from pharmaceutically acceptable cations, provided that at least one R1 is —OH and at least one R1 is —O—(C2-C6 alkylene)-SO3−-T.

### Claim 18 (depends on 17)

The SAE-CD composition of claim 17, wherein the SAE-CD has an average degree of substitution of 4.5 to 7.5.

### Claim 19 (depends on 17)

The SAE-CD composition of claim 17, wherein R1 is independently selected at each occurrence from —OH or —O—(C4 alkylene)-SO3−-T, and -T is Na+ at each occurrence.

### Claim 20 (depends on 17)

The SAE-CD composition of claim 17, wherein the SAE-CD is sulfobutyl ether β-cyclodextrin having the structure:
wherein:
each R is independently —H or —(CH2)4SO3Na; and
the average degree of substitution of —(CH2)4SO3Na is 6.0 to 7.1 per cyclodextrin molecule.

### Claim 21 (depends on 12)

The SAE-CD composition of claim 12 further comprising an active agent.

### Claim 22 (depends on 12)

The SAE-CD composition of claim 12, wherein the SAE-CD composition comprises:
less than 10 ppm of a sulfoalkylating agent;
less than 0.2% wt. of an underivatized cyclodextrin;
less than 0.5% wt. of an alkali metal halide salt; and
less than 0.1% wt. of a hydrolyzed sulfoalkylating agent.

### Claim 23 (depends on 12)

The SAE-CD composition of claim 12, wherein the SAE-CD composition comprises:
less than 250 ppb of a sulfoalkylating agent;
less than 0.1% wt. of an underivatized cyclodextrin;
less than 0.1% wt. of an alkali metal halide salt; and
less than 0.08% wt of a hydrolyzed sulfoalkylating agent.