# US 9,040,033 B2 · Hydroxypropyl methyl cellulose acetate succinate with enhanced acetate and succinate substitution

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- Number: US 9,040,033 B2
- Document ID: US9040033B2
- Status: Granted
- Kind: B2
- Application number: 13/702,331
- Filed: 2011-06-13
- Published: 2013-04-25
- Granted: 2015-05-26
- Earliest claimed: 2010-06-14
- Assignees: Dow Global Technologies LLC
- Applicants: Warren K. Miller; David K. Lyon; Dwayne T. Friesen; William B. Caldwell; David T. Vodak; Daniel E. Dobry
- Inventors: Warren K. Miller; David K. Lyon; Dwayne T. Friesen; William B. Caldwell; David T. Vodak; Daniel E. Dobry
- Web page: https://patentgrep.com/patent/US9040033B2

## CPC

- A61K 47/38: Cellulose; Derivatives thereof
- A61K 9/146: {with organic macromolecular compounds}
- A61K 31/415: 1,2-Diazoles
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- C08B 13/00: Preparation of cellulose ether-esters
- C08L 1/32: Cellulose ether-esters
- 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

Disclosed are polymers of hydroxypropyl methyl cellulose acetate succinate (HPMCAS) with unique degrees of substitution of hydroxypropoxy, methoxy, acetyl, and succinoyl groups. When used in making compositions comprising a low-solubility active agent and such polymers, the polymers provide increased aqueous concentrations and/or improved physical stability of the active agent.

## Claims

### Claim 1

A composition comprising:
an active agent; and
hydroxypropyl methyl cellulose acetate succinate (HPMCAS) having a degree of substitution of methoxy groups (DSM) of ≦1.45, a degree of substitution of acetyl groups (DSAc) of from 1.0 to 1.5, and a combined degree of substitution of acetyl groups (DSAc) and succinoyl groups (DSS) of (DSAc+DSS)≧1.25.

### Claim 2 (depends on 1)

The composition of claim 1 wherein (DSAc+DSS) 1.35.

### Claim 3 (depends on 1)

The composition of claim 1, wherein 1.25≦(DSAc+DSS)≦1.9.

### Claim 4 (depends on 1)

The composition of claim 1, wherein 1.5≦(DSAc+DSS)≦1.7.

### Claim 5 (depends on 1)

The composition of claim 1, wherein:
DSAc is from 1.0 to 1.5,
DSS≧0.20, and
1.25≦(DSAc+DSS)≦1.9.

### Claim 6 (depends on 1)

The composition of claim 1, wherein a ratio of acetyl groups to succinoyl groups is between 0.8 and 6.5.

### Claim 7 (depends on 1)

The composition of claim 1 wherein the ratio of acetyl groups to succinoyl groups is between 1.0 and 6.0.

### Claim 8 (depends on 1)

The composition of claim 1 wherein the ratio of acetyl groups to succinoyl groups is between 1.2 and 5.6.

### Claim 9 (depends on 8)

The composition of claim 8, wherein:
1.0≦DSAc≦1.5, and
0.20≦DSS≦0.7.

### Claim 10

A composition comprising:
an active agent; and
hydroxypropyl methyl cellulose acetate succinate (HPMCAS) having a degree of substitution of methoxy groups (DSM) of ≦1.45, a degree of substitution of acetyl groups (DSAc) of from 1.0 to 1.5, and a degree of substitution of succinoyl groups (DSS) of ≧0.20.

### Claim 11 (depends on 1)

The composition of claim 1 wherein said composition is in the form of a solid amorphous dispersion.

### Claim 12 (depends on 11)

The composition of claim 11 which contains from 1 to 60 weight percent active ingredient and from 40 to 99 weight percent HPMCAS.

### Claim 13 (depends on 12)

The composition of claim 12 wherein at least 90 wt % of the active agent is amorphous.

### Claim 14 (depends on 11)

The composition of claim 11 wherein the active ingredient is a low solubility active ingredient.

### Claim 15 (depends on 11)

The composition of claim 11 wherein the active ingredient is hydrophobic.

### Claim 16 (depends on 1)

The composition of claim 1 which contains from 1 to 60 weight percent active ingredient and from 40 to 99 weight percent HPMCAS.