Nicotine salts, co-crystals, and salt co-crystal complexes

Patent metadata

Field	Value
Publication number	US-10508096-B2
Application number	US-201715695227-A
Country	US
Kind code	B2
Filing date	Sep 5, 2017
Priority date	May 27, 2014
Publication date	Dec 17, 2019
Grant date	Dec 17, 2019

Abstract

The invention provides certain nicotine salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, certain nicotine salt-co-crystals are described, including nicotine and two different coformers. The invention further provides methods of preparation and characterization of nicotine salts, co-crystals, and salt co-crystals. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.

First claim

What is claimed:

1. A salt-co-crystal of nicotine, L-malic acid, and succinic acid, characterized by an X-ray powder diffraction pattern having peaks at one or more of the following 2-theta diffraction angles: 17.1, 18.7, 20.0, 21.6, 25.1, and 25.4
wherein the salt-co-crystal has a stoichiometry of about 2:0.1:0.9 nicotine malate:L-malic acid:succinic acid.

2. The salt-co-crystal of claim 1 , wherein the nicotine is (S)-nicotine.

3. The salt-co-crystal of claim 1 , wherein at least about 50% of the salt or salt-co-crystal is in crystalline form.

4. The salt-co-crystal of claim 1 , wherein at least about 80% of the salt is in crystalline form.

5. The salt-co-crystal of claim 1 , wherein at least about 90% of the salt is in crystalline form.

6. The salt-co-crystal of claim 1 , wherein the salt-co-crystal exhibits a melting point onset around 107° C.

7. The salt-co-crystal of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at two or more of the following 2-theta diffraction angles: 17.1, 18.7, 20.0, 21.6, 25.1, and 25.4.

8. The salt-co-crystal of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at three or more of the following 2-theta diffraction angles: 17.1, 18.7, 20.0, 21.6, 25.1, and 25.4.

9. The salt-co-crystal of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at four or more of the following 2-theta diffraction angles: 17.1, 18.7, 20.0, 21.6, 25.1, and 25.4.

10. The salt-co-crystal of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at five or more of the following 2-theta diffraction angles: 17.1, 18.7, 20.0, 21.6, 25.1, and 25.4.

11. The salt-co-crystal of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at all six of the following 2-theta diffraction angles: 17.1, 18.7, 20.0, 21.6, 25.1, and 25.4.

12. A method of preparing the salt-co-crystal of claim 1 , comprising combining the nicotine, L-malic acid, and succinic acid to form the salt-co-crystal, and isolating the salt-co-crystal.

13. The method of claim 12 , wherein the method comprises combining 1 equivalent of each of nicotine L-malate and succinic acid.

14. The method of claim 12 , wherein the combining is done in a solvent.

15. The method of claim 14 , wherein the solvent comprises acetone.

Assignees

• Reynolds Tobacco Co R

Inventors

• Dull Gary M
• Del Rio Gancedo Susana
• Julia Judit Galcera

Classifications

• C07C65/11

  with carboxyl groups on a condensed ring system containing two rings · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• A61M11/042

  electrical · CPC title

• A24B13/00

  Tobacco for pipes, for cigars, e.g. cigar inserts, or for cigarettes; Chewing tobacco; Snuff (reconstituted tobacco products A24B3/14) · CPC title

• A61M2205/8206

  battery-operated · CPC title