Esterified cellulose ethers of very high molecular weight

Patent metadata

Field	Value
Publication number	US-9890220-B2
Application number	US-201414766609-A
Country	US
Kind code	B2
Filing date	Feb 28, 2014
Priority date	Mar 7, 2013
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

Esterified cellulose ethers which comprise (i) groups of the formula —C(O)—R—COOA or (ii) a combination of aliphatic monovalent acyl groups and groups of the formula —C(O)—R—COOA, wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation, which have a viscosity of up 50 mPa·s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20° C., and a weight average molecular weight M w of at least 220,000 Dalton, or which have a viscosity of up 100 mPa·s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20° C., and a weight average molecular weight M w of at least 310,000 Dalton are useful for preparing solid dispersions comprising drugs.

First claim

The invention claimed is:

1. An esterified cellulose ether
comprising a combination of aliphatic monovalent acyl groups and groups of the formula —C(O)—R—COOA, wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation,
having a viscosity of up to 50 mPa·s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20 ° C., and
having a weight average molecular weight M w of at least 220,000 Dalton, wherein the esterified cellulose ether has been produced by reacting a cellulose ether with a combination of an aliphatic monocarboxylic acid anhydride and a dicarboxylic acid anhydride in an aliphatic carboxylic acid as a reaction diluent at a molar ratio of aliphatic carboxylic acid to dicarboxylic acid anhydride of up to 12/1 and a molar ratio of [aliphatic carboxylic acid / anhydroglucose units of cellulose etherl from 6.5/1 to 7.7/1.

2. The esterified cellulose of claim 1 having a weight average molecular weight M w of at least 250,000 Dalton.

3. The esterified cellulose ether of claim 1 having a viscosity of up 40 mPa·s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20 ° C.

4. An esterified cellulose ether
comprising a combination of aliphatic monovalent acyl groups and groups of the formula —C(O)—R—COOA, wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation,
having a viscosity of up to 100 mPa·s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20 ° C., and
having a weight average molecular weight M w of at least 310,000 Dalton, wherein the esterified cellulose ether has been produced by reacting a cellulose ether with a combination of an aliphatic monocarboxylic acid anhydride and a dicarboxylic acid anhydride in an aliphatic carboxylic acid as a reaction diluent at a molar ratio of aliphatic carboxylic acid to dicarboxylic acid anhydride of up to 12/1 and a molar ratio of [aliphatic carboxylic acid / anhydroglucose units of cellulose ether] from 6.5/1 to 7.7/1.

5. The esterified cellulose ether of claim 4 having a weight average molecular weight M w of at least 350,000 Dalton.

6. The esterified cellulose ether of claim 4 having a viscosity of up 80 mPa·s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20 ° C.

7. The esterified cellulose ether of claim 1 wherein the aliphatic monovalent acyl groups are acetyl, propionyl or butyryl groups and the groups of the formula —C(O)—R—COOA are —C(O)—CH 2 —CH 2 —COOA , —C(O)—CH═CH—COOA, or —C(O)—C 6 H 4 —COOA groups.

8. The esterified cellulose ether of claim 1 being hydroxypropyl methyl cellulose acetate succinate.

9. A composition comprising a liquid diluent and at least one esterified cellulose ether of claim 1 .

10. The composition of claim 9 comprising from 5 to 20 percent of at least one esterified cellulose ether, from 65 to 94 percent of a liquid diluent, and from 1 to 15 percent of an active ingredient, based on the total weight of the composition.

11. A solid dispersion comprising at least one active ingredient and at least one esterified cellulose ether of claim 1 .

12. A dosage form being coated with at least one esterified cellulose ether of claim 1 .

13. A capsule shell comprising at least one esterified cellulose ether of claim 1 .

14. The esterified cellulose ether of claim 4 wherein the aliphatic monovalent acyl groups are acetyl, propionyl or butyryl groups and the groups of the formula —C(O)—R—COOA are —C(O)—CH 2 —CH 2 —COOA , —C(O)—CH═CH—COOA, or —C(O)—C 6 H 4 —COOA groups.

15. The esterified cellulose ether of claim 4 being hydroxypropyl methyl cellulose acetate succinate.

16. A composition comprising a liquid diluent and at least one esterified cellulose ether of claim 4 .

17. The composition of claim 16 comprising from 5 to 20 percent of at least one esterified cellulose ether, from 65 to 94 percent of a liquid diluent, and from 1 to 15 percent of an active ingredient, based on the total weight of the composition.

18. A solid dispersion comprising at least one active ingredient and at least one esterified cellulose ether of claim 4 .

19. A dosage form being coated with at least one esterified cellulose ether of claim 4 .

20. A capsule shell comprising at least one esterified cellulose ether of claim 4 .

Assignees

• Dow Global Technologies Llc

Inventors

• Petermann Oliver
• Brackhagen Meinolf
• Sprehe Matthias

Classifications

• C08L1/32

  Cellulose ether-esters · CPC title

• C08B13/00 Primary

  Preparation of cellulose ether-esters · CPC title

• C08B11/20

  Post-etherification treatments of chemical or physical type, {e.g. mixed etherification in two steps}, including purification · CPC title

• A61K9/2866

  Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose · CPC title

• A61K9/4816

  Wall or shell material · CPC title