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Nicotine Salt With M Eta-salicylic Acid

A salicylic acid, nicotine technology, applied in the field of aerosol nicotine delivery device, condensed nicotine aerosol, film of nicotine m-salicylate, nicotine interruption control, nicotine m-salicylate

Active Publication Date: 2017-08-18
ALEXZA PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the known devices and methods are not particularly suitable for the preparation of nicotine aerosols using liquid medicines

Method used

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  • Nicotine Salt With M Eta-salicylic Acid
  • Nicotine Salt With M Eta-salicylic Acid
  • Nicotine Salt With M Eta-salicylic Acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0214] Synthesis of nicotine m-salicylate: 1.385 g m-salicylic acid (Sigma Aldrich) was dissolved in 25 ml ethanol. 1.62 g of nicotine was added dropwise at room temperature and mixed well for about 30 minutes. The solution was rotevaporated slowly to reduce the volume to about 10ml. Then 5 ml of ethyl acetate was added and stirred for 3-5 minutes. The solution was placed on dry ice for about 1.5 hours, which resulted in a viscous solid mass. After the solvent was evaporated, 20 mL of ethanol was added to dissolve the sticky solid, which was then evaporated. Such recrystallization for purification of crystals is well known in the art. A crystalline solid remained in the flask. The powder was removed from the flask and dried in a vacuum oven at 40°C. 2.6 g were recovered (about 87% yield). The melting point of the solid is 125°C.

Embodiment 2

[0216] Synthesis of nicotine m-salicylate: liquid nicotine (Alfa Aesar, batch #10150504, 99% pure) and m-salicylic acid (3-hydroxybenzoic acid, Sigma Aldrich, batch #STBB7747, 99% pure) A 1:1 nicotine:acid ratio is used to synthesize nicotine m-salicylate. The following synthetic route gives a typical yield of 60-70% and a purity of 99.7%.

[0217] Sample synthesis:

[0218] 1. Dissolve 0.03 molar meta-salicylic acid (-4.16 g) in 65 ml ethanol (200 proof) and mix well for about 20 minutes.

[0219] 2. Add 0.03 molar liquid nicotine (-4.86 g) dropwise to the above solution and mix on a stir plate for 30-40 minutes with periodic shaking. Seed crystals of nicotine m-salicylate were then added and the solution was stirred for an additional 40 minutes and then placed on dry ice for about 40 minutes.

[0220] 3. Filter and wash nicotine m-salicylate with 100% acetone and air dry for ~20 minutes; to homogenize the salt, use a mortar and pestle, then dry the salt in a vacuum oven a...

Embodiment 3

[0223] API evaluation:

[0224]Nicotine m-salicylate raw material (API) was characterized using various analytical methods. The result proves that the synthesized nicotine m-salicylate has high purity.

[0225] A typical calorimetric scan of nicotine m-salicylate powder is shown in figure 2 middle. The melting point is 125°C. The powders were subjected to thermogravimetric analysis in both scanning and isothermal modes. Figure 7 Displays scan data from room temperature to 500°C. It is noteworthy that the flat baseline was approximately (actually, slightly below) 0%, indicating that little or no residue was left. Weighing the pans before and after external equilibration left only ~0.2%. This result suggests minimal carbonization of the acid after exposure to high temperature. Isothermal data were also obtained for API powder (-10 mg per run) at 40°C, 50°C, and 60°C over a period of at least 3 days. In all cases, the mass change was essentially a linear decrease with t...

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Abstract

The present relates to a nicotine salt with an m eta-salicylic acid, disclosure relates generally to the field of nicotine delivery. The disclosure teaches a nicotine meta-salicylate. More specifically, the disclosure teaches a condensation nicotine aerosol, wherein nicotine meta-salicylate is vaporized. This disclosure relates to aerosol nicotine delivery devices. The delivery devices can be activated by actuation mechanisms to vaporize thin films comprising a nicotine meta-salicylate. More particularly, this disclosure relates to thin films of nicotine salt with meta salicylic acid for the treatment of nicotine craving and for effecting smoking cessation.

Description

[0001] This application is a divisional application of the Chinese patent application 201480050267.X filed on July 11, 2014 with the title of "nicotine salt formed with m-salicylic acid". [0002] related application [0003] This application claims priority to U.S. Provisional Application Serial No. 61 / 845,333, filed July 11, 2013, by Myers, entitled "Nicotine Salt with Meta-Salicylic Acid." This application claims priority to U.S. Provisional Application Serial No. 62 / 020,766, filed July 3, 2014, entitled "Drug Delivery and Cessation System, Apparatus, and Method," by Cassella. The entire entire disclosure content thereof is hereby incorporated by reference. Any waiver incurred during the prosecution of the above application is expressly revoked and reconsideration of all related art is kindly requested. technical field [0004] The present invention relates generally to the field of nicotine delivery. The present invention teaches nicotine m-salicylate. More specificall...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/72A61K31/60C07D401/04A61P25/34A61K31/465A24F40/20A24F40/46F24V30/00
CPCA61M15/0081A61M15/0083A61K9/0004A61K9/007A61K31/465A61K31/60A61M11/041A61M15/0065A61M15/06C07D401/04A61K2300/00A61K9/7007A61M11/001A61M15/002A61M5/00A61M35/00A61M2016/0015A61M2205/276A61M2205/3368A61M2205/3553A61M2205/3569A61M2205/3584A61M2205/3592A61M2205/364A61M2205/3653A61M2205/368A61M2205/52A61M2205/8206A61M2209/06A61M2230/06A61M2230/205A61M2230/30A61M2230/42A61M11/042A61M11/047A61M15/0066A24B15/167C07C2601/16A61M31/00A61P25/34A24F40/46A24F40/20A61M2230/005A61M37/00C07C63/08H05B1/025A61M2205/3576A61M2205/50C07C65/10
Inventor D·J·迈尔斯J·卡塞拉
Owner ALEXZA PHARMA INC
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