Chlorhexidine-cyclamate complexes and oral care compositions comprising the same

Patent metadata

Field	Value
Publication number	US-11278481-B2
Application number	US-201716955308-A
Country	US
Kind code	B2
Filing date	Dec 19, 2017
Priority date	Dec 19, 2017
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

The present disclosure provides a chlorhexidine-cyclamate complex having a formula [C22H32Cl2N10][C6H12NO3S]2 having antibacterial and antiplaque properties, together with oral care compositions comprising the complex, and methods of making and using these complexes and compositions.

First claim

What is claimed is:

1. An oral care composition comprising the chlorhexidine-cyclamate complex having a formula [C 22 H 32 Cl 2 N 10 ][C 6 H 12 NO 3 S 2 ] 2 in combination with an orally acceptable carrier.

2. The oral care composition of claim 1 wherein the chlorhexidine-cyclamate complex is formed, in whole or in part, in situ from chlorhexidine and sodium cyclamate.

3. The oral care composition of claim 1 wherein the wherein the chlorhexidine-cyclamate complex forms as a precipitate in aqueous solution.

4. The oral care composition of claim 1 wherein the chlorhexidine-cyclamate complex is present in an amount of 0.01 to 40% by weight of the composition.

5. The oral care composition of claim 1 wherein the composition is in the form of a dentifrice, gel or mouthwash.

6. A method of killing bacteria comprising contacting the bacteria with the oral care composition of claim 1 .

7. A method of treating, reducing or preventing plaque comprising contacting the plaque with the oral care composition of claim 1 .

8. The oral care composition of claim 1 , wherein the chlorhexidine-cyclamate complex is in crystalline form.

9. The oral care composition of claim 1 , wherein the chlorhexidine-cyclamate complex is anhydrous.

10. The oral care composition of claim 1 , wherein the chlorhexidine-cyclamate complex is in the form of a hydrate, hemi-hydrate or polyhydrate.

11. The oral care composition of claim 10 , wherein the chlorhexidine-cyclamate complex has the formula [C 22 H 32 Cl 2 N 10 ][C 6 H 12 NO 3 S] 2 .H 2 O.

12. The oral care composition of claim 1 , wherein the chlorhexidine-cyclamate complex is formed from a mixture of chlorhexidine and sodium cyclamate in a molar ratio of chlorhexidine:sodium cyclamate of 1:1 to 1:3.

13. The oral care composition of claim 1 , the chlorhexidine-cyclamate complex is in crystalline form in a P2 1 /c space group.

14. The oral care composition of claim 1 , the chlorhexidine-cyclamate complex comprises a structure wherein a biguanide moiety of the chlorhexidine cation is coordinated by two cyclamate ligands and a water ligand as shown in FIG. 9 .

15. The oral care composition of claim 1 , wherein the chlorhexidine-cyclamate complex is crystallized in an aqueous solution.

16. The oral care composition of claim 15 , wherein the aqueous solution contains 84 wt % water, 3 wt. % ethanol, and 10 wt. % glycerin.

Assignees

• Colgate Palmolive Co

Inventors

• Hao Zhigang
• Cheng Chi-Yuan
• Pan Long
• Subramanyam Ravi

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• A61K8/43 Primary

  Guanidines · CPC title

• A61K47/541

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

• A61K8/0295

  Liquid crystals · CPC title

• C07C279/265

  containing two or more biguanide groups · CPC title