US 12,391,665 B2
Vaporizable alkaloid compositions and methods of use thereof
Charlotte L. Owen, Seguin, TX (US); Richard Avila, Jr., Prescott Valley, AZ (US); and Geoff W. Habicht, Phoenix, AZ (US)
Assigned to Ready Mix Naturals, LLC, Seguin, TX (US)
Filed by Ready Mix Naturals, LLC, Seguin, TX (US)
Filed on Aug. 16, 2024, as Appl. No. 18/807,086.
Application 18/807,086 is a continuation of application No. 18/238,709, filed on Aug. 28, 2023.
Application 18/238,709 is a continuation in part of application No. 18/227,815, filed on Jul. 28, 2023, granted, now 11,964,958, issued on Apr. 23, 2024.
Claims priority of provisional application 63/439,650, filed on Jan. 18, 2023.
Prior Publication US 2024/0400539 A1, Dec. 5, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/04 (2006.01); A61K 9/00 (2006.01); A61K 47/12 (2006.01); A61K 47/18 (2017.01); C07D 213/72 (2006.01); C07D 401/14 (2006.01); C07D 413/14 (2006.01)
CPC C07D 401/04 (2013.01) [A61K 9/007 (2013.01); A61K 47/12 (2013.01); A61K 47/18 (2013.01); C07D 213/72 (2013.01); C07D 401/14 (2013.01); C07D 413/14 (2013.01)] 23 Claims
 
1. A vaporizable alkaloid composition, comprising:
at least one substituted pyridine compound of Formula (I):

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 or a salt, or mixed salt thereof, wherein:
A is selected from:

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R1, R2, R3, R4 and R5 are independently selected from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, and

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R6 and R7 are independently selected from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl and substituted alkenyl, or R6 and R7 together are ═O;
R8, R9, R10, R11, and R12 are independently selected from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, and substituted alkenyl;
R13 and R14 are independently selected from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, and substituted alkenyl, or R13 and R14 together are ═O;
n is an integer from 1 to 10; and
R15 and R16 are independently selected from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl and substituted alkenyl, or R15 and R16 together with the N atom to which they are bonded form a 3-8 membered substituted heterocyclic ring,
with the proviso that if A is

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 and R5 is methyl, then R1, R2, R3, R4, R6, R7, R8, R9, R10, and R11 cannot all be H;
at least one solvent, and
at least one flavoring agent selected from the group comprising geraniol, geranial, valeric acid, ethyl maltol, ethyl butyrate, ethyl acetate, maltol, ethyl 3-methyl-3-phenylglycidate, furaneol, methyl cyclopentenolone, methyl cyclopentenolone, ethyl cyclopentenolone, δ-decalactone, γ-decalactone, α-nonalactone, β-nonalactone, cis-3-hexanol, iso-amyl acetate, ethyl-2-methyl butyrate, butyric acid, ethyl butyrate, 2-methylbutyric acid, benzyl alcohol, ethyl hexanoate, benzaldehyde, iso-amyl isovalerate, hexanoic acid, ethyl propionate, γ-undecalactone, acetyl propionyl, raspberry ketone, furfural, 5-methylfurfural, maltol, 2-acetylpyrazine, 2,3,5-trimethylpyrazine, 2-acetylpyrrole, 2-isopropyl-4-methylthiazole, 2-isobutylthiazole, furfuryl mercaptan, thiomenthone, p-menthene-8-thiol, tropathiane, hexyl acetate and mixtures thereof, wherein the vaporizable alkaloid composition is entirely devoid of (R) or (S) nicotine.