Dual functioning ionic liquids and salts thereof

Patent metadata

Field	Value
Publication number	US-9278134-B2
Application number	US-200913142559-A
Country	US
Kind code	B2
Filing date	Dec 29, 2009
Priority date	Dec 29, 2008
Publication date	Mar 8, 2016
Grant date	Mar 8, 2016

Abstract

Disclosed herein are ionic liquid compositions comprising active pharmaceutical, biological, and nutritional compounds, and methods of use. Further disclosed are compositions of matter including liquid ion pairs alone or in solution and their use; compositions of ionic liquids that are ‘solvated,’ for example, ‘hydrated’ and their uses.

First claim

What is claimed is:

1. A method for preparing a bioactive co-ionic ionic liquid composition comprising:
combining two pharmaceutical actives selected from single charged cations, cation precursors, and combinations thereof, represented as B 1 and B 2 , with one anion having a single negative charge, represented as A, or
combining two pharmaceutical actives selected from single charged anions, anion precursors, and combinations thereof, represented as A 1 and A 2 , with one cation having a single positive charge, represented as B,
thereby producing a co-ionic liquid [B 1 HB 2 ]A or B[A 1 HA 2 ], where H is hydrogen, that is liquid at a temperature at or below about 150° C.,
wherein B 1 and B 2 are selected from choline, lidocaine, tramadolium, caffeine, cetylpyridinium, ephedrinium, propantheline, acetaminophen derivative, procainamide, promethazine, and combinations thereof, and
wherein A 1 and A 2 are selected from salicylate, ibuprofenate, lactate, camphorsulfonate, trans-cinnamate, docusate, niacinate, clofibrate, and combinations thereof.

2. The method of claim 1 wherein from about 75% to about 100% of the composition comprises an ion pair.

3. The method of claim 1 , wherein the cations and anions or the cation precursors and anion precursors are combined in the presence of one or more solvents, thereby producing a solvated ionic liquid; wherein at least a portion of the solvent provides direct solvation.

4. The method according to claim 1 , wherein combining two anions or anion precursors, represented as A 1 and A 2 , with one cation, represented as B, is by adding acid HA 2 to a non-protic ionic liquid having the formula BA 1 .

5. The method according to claim 1 , wherein combining two cations or cation precursors, represented as B 1 and B 2 , with one anion, represented as A, is by adding base B 2 to an ionic liquid having the formula [B 1 H]A.

6. The method according to claim 1 , wherein combining the two cation precursor with one anion or two anion precursor with one cation is accomplished by an acid-base neutralization reaction.

7. The method according to claim 1 , wherein the cation B comprises tetrabutylphosphonium and the anion A comprises salicylate and ibuprofenate, cinnamate, camphorsulfonate, lactate or thiosalicylate.

8. The method according to claim 1 , wherein the cation B is tetrabutylphosphonium and the anions A 1 and A 2 are ibuprofenate or niacinate.

9. The method according to claim 1 , wherein the cation B is cetylpyridinium and the anions A 1 and A 2 are salicylate and ibuprofenate, cinnamate, or clofibrate.

10. The method according to claim 1 , wherein the cation B is lidocaine and the anions A 1 and A 2 are salicylate and Ibuprofenate.

11. The method according to claim 1 , wherein the cation B is tramadolium and the anions A 1 and A 2 are salicylate and ibuprofenate.

12. The method according to claim 1 , wherein the cations B 1 and B 2 are ephedrinium and lidocaine and the anion A is ibuprofenate.

13. The method according to claim 1 , wherein the cations B 1 and B 2 are tramadolium and lidocaine and the anion A is salicylate or ibuprofenate.

14. The method according to claim 1 , wherein the cations B 1 and B 2 are promethazine and ephedrine and the anion A is docusate or salicylate.

Assignees

• Rogers Robin D
• Daly Daniel T
• Macfarlane Douglas
• Scott Janet L
• Seddon Kenneth R
• Gurau Gabriela
• Bica Katharina
• Turanjanin Jelena
• Dean Pamela M
• Univ Alabama
• Univ Monash
• Queen S University Belfast

Inventors

• Rogers Robin D
• Daly Daniel T
• Macfarlane Douglas
• Scott Janet L
• Seddon Kenneth R
• Gurau Gabriela
• Bica Katharina
• Turanjanin Jelena
• Dean Pamela M

Classifications

• A61K47/4803 Primary

  Human Necessities · mapped topic

• A61K47/541 Primary

  Organic ions forming an ion pair complex with the pharmacologically or therapeutically active agent · CPC title