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

Patent metadata

Field	Value
Publication number	US-11136305-B2
Application number	US-202016739427-A
Country	US
Kind code	B2
Filing date	Jan 10, 2020
Priority date	May 27, 2014
Publication date	Oct 5, 2021
Grant date	Oct 5, 2021

Abstract

The invention provides certain nicotine salts, co-crystals, and salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, nicotine salts with mucic acid, 3,5-dihydroxybenzoic acid, and 2,3-dihydroxybenzoic acid, and crystalline polymorphic forms of nicotine 4-acetamidobenzoate, nicotine gentisate, and nicotine 1-hydroxy-2-naphthoate are described. The invention further provides methods of preparation and characterization of such nicotine salts, co-crystals, and salt co-crystals and polymorphic forms thereof. 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 of nicotine and 2,3-dihydroxybenzoic acid, characterized by an X-ray powder diffraction pattern having peaks at one or more of the following 2-theta diffraction angles: 12.4, 12.5, 15.2, 18.3, 19.7, 20.3, 20.9, 24.9, 25.2, 26.5, and 30.4.

2. The salt of claim 1 , wherein about 50% or more of the salt is in crystalline form.

3. The salt of claim 1 , having a stoichiometry of about 1:1 nicotine:acid.

4. The salt of claim 1 , wherein the salt is in the form of irregular plates up to about 150 μm in size.

5. The salt of claim 1 , wherein the salt exhibits a melting point onset of about 157° C.

6. The salt of claim 1 , wherein about 70% or more of the salt is in crystalline form.

7. The salt of claim 1 , wherein about 80% or more of the salt is in crystalline form.

8. The salt of claim 1 , wherein about 90% or more of the salt is in crystalline form.

9. The salt of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at two or more of the following 2-theta diffraction angles: 12.4, 12.5, 15.2, 18.3, 19.7, 20.3, 20.9, 24.9, 25.2, 26.5, and 30.4.

10. The salt of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at three or more of the following 2-theta diffraction angles: 12.4, 12.5, 15.2, 18.3, 19.7, 20.3, 20.9, 24.9, 25.2, 26.5, and 30.4.

11. The salt of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at five or more of the following 2-theta diffraction angles: 12.4, 12.5, 15.2, 18.3, 19.7, 20.3, 20.9, 24.9, 25.2, 26.5, and 30.4.

12. The salt of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at eight or more of the following 2-theta diffraction angles: 12.4, 12.5, 15.2, 18.3, 19.7, 20.3, 20.9, 24.9, 25.2, 26.5, and 30.4.

13. The salt of claim 1 , characterized by an X-ray powder diffraction pattern having peaks at all of the following 2-theta diffraction angles: 12.4, 12.5, 15.2, 18.3, 19.7, 20.3, 20.9, 24.9, 25.2, 26.5, and 30.4.

Assignees

• Reynolds Tobacco Co R

Inventors

• Dull Gary M
• Carr Andrew
• Sharp Emma

Classifications

• A24B15/30

  by organic substances {(A24B15/281 takes precedence)} · CPC title

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• A61P25/26

  Psychostimulants, e.g. nicotine, cocaine · CPC title

• C07D401/04 Primary

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

• C07C65/11

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