Cellulose ethers esterified with dicarboxylic acid

Patent metadata

Field	Value
Publication number	US-2016289344-A1
Application number	US-201414777838-A
Country	US
Kind code	A1
Filing date	May 7, 2014
Priority date	May 14, 2013
Publication date	Oct 6, 2016
Grant date	—

Abstract

Esterified cellulose ethers comprising groups of formula —C(O)—CHR′—CHR″—COOA, wherein, R′ and R″ are hydrogen or (—S)m (—R 1 )n-R 2 , wherein R 1 is a hydrocarbon group having 1 to 4 carbon atoms, R 2 is an optionally substituted 5- or 6-membered cyclic group, m and n each independently are 0 or 1, and A is hydrogen or a cation, with the proviso that in each group CHR′—CHR″ one of R′ and R″ is hydrogen and the other one is (—S)m (—R 1 )n-R′, are useful as excipients for maintaining the concentration of poorly water-soluble drugs in aqueous liquids at supersaturation levels.

First claim

1 . An esterified cellulose ether comprising groups of formula
—C(O)—CHR′—CHR″—COOA,
wherein R′ and R″ are hydrogen or (—S) m (—R′) n —R 2 , wherein R 1 is a hydrocarbon group having 1 to 4 carbon atoms, R 2 is an optionally substituted 5- or 6-membered cyclic group, m and n each independently are 0 or 1, and A is hydrogen or a cation, with the proviso that in each group CHR′—CHR″ one of R′ and R″ is hydrogen and the other one is (—S) m (—R′) n —R 2 .

2 . The esterified cellulose ether of claim 1 wherein R 1 is CH 2 .

3 . The esterified cellulose ether of claim 1 wherein R 2 is non-substituted 5- or 6-membered cyclic group.

4 . The esterified cellulose ether of claim 1 wherein m=1.

5 . The esterified cellulose ether of claim 1 wherein m=0.

6 . The esterified cellulose ether of claim 1 wherein n=0.

7 . The esterified cellulose ether of claim 1 wherein R 2 is cyclohexyl or phenyl.

8 . The esterified cellulose ether of claim 1 being an esterified hydroxyalkyl methylcellulose.

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

10 . The composition of claim 9 additionally comprising at least one active ingredient and optionally one or more adjuvants.

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

12 . The solid dispersion of claim 11 wherein the solid dispersion has been formulated into tablets, pills, granules, pellets, caplets, microparticles, fillings of capsules, or into a paste, cream, suspension or slurry.

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

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

15 . A process for producing the esterified cellulose ether of claim 1 , wherein a cellulose ether is esterified with a substituted succinic anhydride of formula I

wherein R is (—S) m (—R 1 ) n —R 2 , wherein R 1 is a hydrocarbon group having 1 to 4 carbon atoms, R 2 is an optionally substituted 5- or 6-membered cyclic group, and m and n each independently are 0 or 1.

Assignees

• Dow Global Technologies Llc
• Univ Minnesota

Inventors

• Yin Ligeng
• Hillmyer Marc A
• Guillaudeu Steven J
• Schmitt Robert L

Classifications

• A61K47/38

  Cellulose; Derivatives thereof · CPC title

• A61K31/4166

  having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin · CPC title

• C08B13/00 Primary

  Preparation of cellulose ether-esters · CPC title

• A61K9/146

  with organic macromolecular compounds · CPC title

• A61K31/095

  Sulfur, selenium, or tellurium compounds, e.g. thiols · CPC title