Organic anion lithium ionic cocrystal compounds and compositions

Patent metadata

Field	Value
Publication number	US-9840521-B2
Application number	US-201414779774-A
Country	US
Kind code	B2
Filing date	Apr 18, 2014
Priority date	Apr 19, 2013
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

A cocrystal having the formula LiX.aM, or a solvate or hydrate thereof, wherein X is a conjugate base of an organic acid, M is a neutral organic molecule, and a is from 0.5 to 4, pharmaceutical compositions comprising such cocrystals, cocrystal solvates, or cocrystal hydrates, and methods of preparing such cocrystals, cocrystal solvates, or cocrystal hydrates, and such pharmaceutical compositions.

First claim

What is claimed is:

1. A pharmaceutical composition comprising an ionic cocrystal compound or a solvate or hydrate thereof, the ionic cocrystal compound comprising a lithium salt and a neutral organic molecule in a stoichiometric ratio wherein the lithium salt comprises a conjugate base of an organic acid;
wherein the neutral organic molecule is a neutral zwitterionic compound, a polyphenol, or an amino acid; and
wherein the organic acid is benzoic acid, salicylic acid, oxalic acid, or saccharin.

2. The pharmaceutical composition of claim 1 wherein the ionic cocrystal compound or the solvate or hydrate thereof has the formula LiX*aM or LiX*aM*bS wherein X is a conjugate base of an organic acid, M is a neutral organic molecule, a is from 0.5 to 4, b is 0.5, 1, 1.5, 2, 2.5 or 3, and S is solvent or water;
wherein the neutral organic molecule is a neutral zwitterionic compound, a polyphenol, or an amino acid; and
wherein the organic acid is benzoic acid, salicylic acid, oxalic acid, or saccharin.

3. The pharmaceutical composition of claim 2 wherein the pharmaceutical composition comprises a pharmaceutically acceptable carrier or diluent.

4. The pharmaceutical composition of claim 2 wherein the pharmaceutical composition is in a dosage unit form comprising a powder, a tablet, a capsule, or a liquid.

5. The pharmaceutical composition of claim 2 wherein M is a nicotinic acid or an amino acid.

6. The pharmaceutical composition of claim 2 wherein M is alanine, arginine, asparagine, aspartic acid, cysteine, isoleucine, glutamic acid, glutamine, glycine, histidine, leucine, lysine, methionine, phenylalanine, proline, selenocysteine, serine, taurine, threonine, tryptophan, tyrosine, or valine.

7. The pharmaceutical composition of claim 2 wherein X is a conjugate base of an organic acid having a pKa in the range of 0 to 10.

8. The pharmaceutical composition of claim 2 wherein the neutral organic molecule is selected from the group consisting of phenolic acids, flavonoids, stilbenoids; tannins, monophenols, capsaicinoids, and curcumin.

9. The pharmaceutical composition of claim 2 wherein a is 0.5.

10. The pharmaceutical composition of claim 2 wherein a is 1.

11. The pharmaceutical composition of claim 2 wherein a is 1.5.

12. The pharmaceutical composition of claim 2 wherein a is 2.

13. The pharmaceutical composition of claim 2 wherein a is 2.5.

14. The pharmaceutical composition of claim 2 wherein a is 3.

15. The pharmaceutical composition of claim 2 wherein a is 3.5.

16. The pharmaceutical composition of claim 2 wherein a is 4.

Assignees

• Univ South Florida

Inventors

• Zaworotko Michael John
• Duggirala Naga
• Smith Adam John
• Shytle Roland Douglas

Classifications

• A61K33/00

  Medicinal preparations containing inorganic active ingredients · CPC title

• A61K33/14

  Alkali metal chlorides; Alkaline earth metal chlorides · CPC title

• C07D207/16

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07F1/02 Primary

  Lithium compounds · CPC title

• C07C229/08

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title