IP Library › Granted Patent US 12,324,801
Granted Patent B2
US 12,324,801 · App. 17/352,071 · Granted Jun 10, 2025

Water soluble compositions comprising purified cannabinoids

Inventor: Kurt Aron Levy (Superior, CO)
Assignee: CANOPY GROWTH CORPORATION
A61K31/353A61K9/08A61K9/107A61K31/01A61K31/015A61K31/045A61K31/05A61K31/065A61K31/105A61K31/122A61K31/192A61K31/352A61K31/355A61K36/185A61K45/06A61K47/22
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,324,801
App. No.
17/352,071
Granted
Jun 10, 2025
Kind
B2
Abstract

This disclosure relates to new compositions and methods for making cannabinoid formulations. In one embodiment, this disclosure provides water soluble compositions comprising a first purified cannabinoid and Vitamin E TPGS. In one embodiment, the disclosure herein comprises a method of making powders comprising heatings material to a first temperature and a second temperature.

Claims (34)

1. A liquid composition, comprising:

one or more purified cannabinoids selected from the group consisting of D9-THC, D8-THC, THCA, THCV, D8-THCV, D9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, and CBLVA;

Vitamin E TPGS; and

water,

wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:10 based on mass percent.

2. The liquid composition of claim 1 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:8.

3. The liquid composition of claim 1 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:6.

4. The liquid composition of claim 1 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:4.

5. The liquid composition of claim 1 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:2.

6. The liquid composition of claim 1 , wherein the one or more purified cannabinoids comprise THCA, CBC, THC, CBN, CBD, CBG, CBGA, CBDA, or a combination thereof.

7. The liquid composition of claim 1 , wherein the one or more purified cannabinoids comprise CBD, THC, or a combination thereof.

8. The liquid composition of claim 1 , wherein the one or more purified cannabinoids comprise a combination of THC and CBD.

9. The liquid composition of claim 1 , further comprising one or more purified terpenes.

10. The liquid composition of claim 9 , wherein the one or more purified terpenes is Alpha-terpineol, Bergamotene (a-cis-Bergamotene) (a-trans-Bergamotene), Bisabolol (13-Bisabolol), Borneol, Camphor, Capsaicin, Carvacrol, Caryophyllene (13-Caryophyllene), Caryophyllene oxide, Cineole, Cinnamaldehyde (a-amyl-Cinnamaldehyde) (a-hexyl-Cinnamaldehyde), Cinnamyl Alcohol, Citronella!, Citronellol, Ethyl, Cinnamate, Eucalyptol/1,8-Cineole, Farnesol, Fenchel (13-Fenchol), Geranyl acetate, Germacrene B, Guaiene (a-Guaiene), Humulene (a-Humulene) (13-Humulene), lonol (3-oxo-a-ionol) (13-lonol), lonone (a-lonone) (13-lonone), Isoamyl acetate, Isoprene, Kahweol, Laevo-Carvone, Lavandulol, Limonene, Linalool, Linalyl acetate, Luteolin, Lycopene, Menthol, Myrcene (13-Myrcene), Nerol, Nerolidol, Neryl acetate, P-cymene, Phytol, Pinene, Pristimerin, Retinol, Terpin hydrate, Terpineol, Terpinol-4-ol, Terpinolene, Thujone, Thymol, or Vanillin.

11. The liquid composition of claim 1 , wherein the liquid composition is a juice, a soft drink, a wine, a cocktail, a medicinal preparation, coffee, or tea.

12. A liquid composition, comprising:

a first purified cannabinoid selected from the group consisting of D9-THC, D8-THC, THCA, THCV, D8-THCV, D9-THCV, THCVA, CBD, CBDA, CBDV, CBDVA, CBC, CBCA, CBCV, CBCVA, CBG, CBGA, CBGV, CBGVA, CBN, CBNA, CBNV, CBNVA, CBND, CBNDA, CBNDV, CBNDVA, CBE, CBEA, CBEV, CBEVA, CBL, CBLA, CBLV, and CBLVA;

Vitamin E TPGS; and

water,

wherein the liquid composition comprises a ratio of the first purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:10 based on mass percent.

13. A liquid composition, comprising:

one or more purified cannabinoids;

Vitamin E TPGS; and water,

wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:10 based on mass percent and the liquid composition does not comprise a TPGS coprecipitate.

14. The liquid composition of claim 13 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:8.

15. The liquid composition of claim 13 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:6.

16. The liquid composition of claim 13 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:4.

17. The liquid composition of claim 13 , wherein the liquid composition comprises a ratio of total purified cannabinoid content to Vitamin E TPGS of about 1:1 to about 1:2.

18. The liquid composition of claim 13 , wherein the one or more purified cannabinoids comprise THCA, CBC, THC, CBN, CBD, CBG, CBGA, CBDA, or a combination thereof.

19. The liquid composition of claim 13 , wherein the one or more purified cannabinoids comprise CBD, THC, or a combination thereof.

20. The liquid composition of claim 13 , wherein the one or more purified cannabinoids comprise a combination of THC and CBD.

21. The liquid composition of claim 13 , further comprising one or more purified terpenes.

22. The liquid composition of claim 21 , wherein the one or more purified terpenes is Alpha-terpineol, Bergamotene (a-cis-Bergamotene) (a-trans-Bergamotene), Bisabolol (13-Bisabolol), Borneol, Camphor, Capsaicin, Carvacrol, Caryophyllene (13-Caryophyllene), Caryophyllene oxide, Cineole, Cinnamaldehyde (a-amyl-Cinnamaldehyde) (a-hexyl-Cinnamaldehyde), Cinnamyl Alcohol, Citronella!, Citronellol, Ethyl, Cinnamate, Eucalyptol/1,8-Cineole, Farnesol, Fenchel (13-Fenchol), Geranyl acetate, Germacrene B, Guaiene (a-Guaiene), Humulene (a-Humulene) (13-Humulene), lonol (3-oxo-a-ionol) (13-lonol), lonone (a-lonone) (13-lonone), Isoamyl acetate, Isoprene, Kahweol, Laevo-Carvone, Lavandulol, Limonene, Linalool, Linalyl acetate, Luteolin, Lycopene, Menthol, Myrcene (13-Myrcene), Nerol, Nerolidol, Neryl acetate, P-cymene, Phytol, Pinene, Pristimerin, Retinol, Terpin hydrate, Terpineol, Terpinol-4-ol, Terpinolene, Thujone, Thymol, or Vanillin.

23. The liquid composition of claim 13 , wherein the liquid composition is a juice, a soft drink, a wine, a cocktail, a medicinal preparation, coffee, or tea.

Assignments (6)
SECURITY INTEREST Recorded Jan 20, 2026
From: CANOPY GROWTH CORPORATION; TWEED INC.
To: JGB COLLATERAL LLC
Reel/Frame 073521/0250 →
RELEASE OF SECURITY INTEREST IN PATENT INTELLECTUAL PROPERTY Recorded Jan 9, 2026
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: CANOPY GROWTH CORPORATION
Reel/Frame 074281/0925 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2025
From: LEVY, KURT ARON
To: EBBU, LLC
Reel/Frame 070900/0654 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2025
From: EBBU INC.
To: CANOPY GROWTH CORPORATION
Reel/Frame 070900/0716 →
CHANGE OF NAME Recorded Apr 21, 2025
From: EBBU LLC
To: EBBU INC.
Reel/Frame 071410/0618 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Oct 16, 2023
From: CANOPY GROWTH CORPORATION
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 065239/0156 →
Continuity (6)
Continuation 17024601 · Sep 17, 2020
Continuation 16860589 · Apr 28, 2020
Continuation 16700678 · Dec 2, 2019
Continuation 16328833
Provisional Application 62380954 · Aug 29, 2016
Related Publication 20210308098A1 · Oct 7, 2021
References Cited (79)
US 4837228A · Elsohly et al. · 1989 [cited by applicant]
US 5891469A · Amselem · 1999 [cited by applicant]
US 6982282B2 · Elsohly et al. · 2006 [cited by applicant]
US 7923026B2 · Moschwitzer · 2011 [cited by applicant]
US 8790719B2 · Parolaro et al. · 2014 [cited by applicant]
US 10568865B2 · Levy · 2020 [cited by applicant]
US 10722490B2 · Levy · 2020 [cited by applicant]
US 20030101902A1 · Reitnauer et al. · 2003 [cited by applicant]
US 20060257463A1 · Elsohly et al. · 2006 [cited by applicant]
US 20080193725A1 · Saint-Romain · 2008 [cited by applicant]
US 20090098192A1 · Fuisz · 2009 [cited by applicant]
US 20090133704A1 · Strickland et al. · 2009 [cited by applicant]
US 20100298579A1 · Steup et al. · 2010 [cited by applicant]
US 20110052694A1 · Stinchcomb et al. · 2011 [cited by applicant]
US 20110306660A1 · Goskonda et al. · 2011 [cited by applicant]
US 20120004251A1 · Whalley et al. · 2012 [cited by applicant]
US 20130059018A1 · Parolaro et al. · 2013 [cited by applicant]
US 20130276779A1 · Hale et al. · 2013 [cited by applicant]
US 20140100269A1 · Goskonda et al. · 2014 [cited by applicant]
US 20140221469A1 · Ross et al. · 2014 [cited by applicant]
US 20140243405A1 · Whalley et al. · 2014 [cited by applicant]
US 20140271940A1 · Wurzer et al. · 2014 [cited by applicant]
US 20140356420A1 · Huang · 2014 [cited by applicant]
US 20150064250A1 · Ghebre-Sellassie et al. · 2015 [cited by applicant]
US 20150126595A1 · Smith et al. · 2015 [cited by applicant]
US 20150258040A1 · Lynch et al. · 2015 [cited by applicant]
US 20150297556A1 · Smith · 2015 [cited by applicant]
US 20160029658A1 · Segawa et al. · 2016 [cited by applicant]
US 20160081976A1 · Bromley · 2016 [cited by applicant]
US 20160250270A1 · Cooper et al. · 2016 [cited by applicant]
US 20160256395A1 · De Bries et al. · 2016 [cited by applicant]
US 20160279073A1 · Donsky et al. · 2016 [cited by applicant]
US 20170049754A1 · Diederich et al. · 2017 [cited by applicant]
US 20170266153A1 · Levy et al. · 2017 [cited by applicant]
US 20190030101A1 · Cooper et al. · 2019 [cited by applicant]
US 20190090527A1 · Levy · 2019 [cited by applicant]
US 20190183853A1 · Levy · 2019 [cited by applicant]
US 20190388384A1 · Segal et al. · 2019 [cited by applicant]
US 20200000766A1 · Reid et al. · 2020 [cited by applicant]
US 20200121637A1 · Levy · 2020 [cited by applicant]
CA 2684562 · 2008 [cited by applicant]
CA 3030535 · 2018 [cited by applicant]
CN 100482657 · 2005 [cited by applicant]
CN 102869356 · 2013 [cited by applicant]
CN 103826621 · 2014 [cited by applicant]
GB 2495118 · 2013 [cited by applicant]
WO WO2008024408 · 2008 [cited by applicant]
WO WO2011135591 · 2011 [cited by applicant]
WO WO2014100231 · 2014 [cited by applicant]
WO WO2014159688 · 2014 [cited by applicant]
WO WO2015068052 · 2015 [cited by applicant]
WO WO2015200049 · 2015 [cited by applicant]
WO WO2016109624 · 2016 [cited by applicant]
WO WO2018011808 · 2018 [cited by applicant]
Office Action dated Nov. 22, 2022, for EP App No. 17847412.8, 4 pgs. [cited by applicant]
Ansel et al., “Pharmaceutical Dosage Forms and Drug Delivery Systems, 7th Edition,” Lippincott, Williams, & Wilkins, 1999 , pp. 48-53. [cited by applicant]
Chen, “Some of the Parts: Is Marijuana's ‘Entourage Effect’ Scientifically Valid?” Scientific American, Apr. 20, 2017, retrieved from www.scientificamerican.com/article/some-of-the-parts-is-marijuana-rsquo-s-ldquo-entou… [cited by applicant]
Extended European Search Report for European Patent Application No. 1784 7 412.8, dated May 26, 2020, 7 pages. [cited by applicant]
Haibo et al., “Research Progress on Chemical ingredient and Pharmacological activity of Fructus Cannabis,” Chinese Journal of Ethnomedicine and Ethnophamacy, vol. 19, No. 8, 2010, pp. 56-57. [cited by applicant]
International Search Report and Written Opinion for International (PCT) Application No. PCT/US2017/049219, dated Nov. 3, 2017, 7 pages. [cited by applicant]
Izzo et al., “Inhibitory effect of cannabichromene, a major non-psychotropic cannabinoid extracted from [cited by applicant]
Klauke et al., “The cannabinoid CB2 receptor-selective phytocannabinoid beta-cryophyllene exerts analgesic effects in mouse models of inflammatory and neuropathic pain,” European Neuropsychopharmacoloav, vol. 24. 2014. … [cited by applicant]
Maione et al., “Non-psychoactive cannabinoids modulate the descending pathway of antinociception in anaesthetized rats through several mechanisms of action,” British Journal of Pharmacoloav. vol. 162. 2011. pp. 584-596. [cited by applicant]
Marriot et al., “Pharmaceutical Compounding and Dispensing, 2nd Edition,” Pharmaceutical Press, 2010, 305 pages. [cited by applicant]
McPartland et al., “Cannabis and Cannabis Extracts: Greater than the Sum of Their Parts?,” The Haworth Press, Inc., 2001, pp. 103-132. [cited by applicant]
McPartland et al., “Side Effects of Pharmaceuticals Not Elicited by the Comparable Herbal Medicines: The Case of Tetrahydrocannabinol and Marijuana,” Alternative Therapies in Health and Medicine, vol. 5, No. 4, Jul. 199… [cited by applicant]
Mosely, “Ebbu Announces Groundbreaking Production Scale Purification Process,” Business Wire, Jun. 13, 2016, retrieved from www.businesswire.com/news/home/20160613006490/en/Ebbu-Announces-Groundbreaking-Production-Scal … [cited by applicant]
Omar et al., “Optimisation and characterisation of marihuana extracts obtained by supercritical fluid extraction and focused ultrasound extraction and retention time locking GC-MS,” Journal of Separate Science, vol. 36,… [cited by applicant]
Ross et al., “The Volatile Oil Composition of Fresh and Air-Dried Buds of [cited by applicant]
Russo et al., “Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entouraae effects,” British Journal of Pharmacoloav, vol. 163, 2011, DD. 1344-1364. [cited by applicant]
Tomic et al., “Antihyperalgesic and Antiedematous Activities of Bisabolol-Oxides-Rich Matricaria Oil in a Rat Model of Inflammation,” Phytotheraov Research, vol. 28, 2014, pp. 759-766. [cited by applicant]
Non-Final Office Action dated Jan. 28, 2020 in U.S. Appl. No. 16/700,678. [cited by applicant]
Non-Final Office Action dated May 14, 2019 in U.S. Appl. No. 16/328,833. [cited by applicant]
Non-Final Office Action dated Jun. 8, 2020 U.S. Appl. No. 16/860,589. [cited by applicant]
Notice of Allowance dated Jan. 27, 2020 in U.S. Appl. No. 16/328,833. [cited by applicant]
Notice of Allowance dated Apr. 24, 2020 in U.S. Appl. No. 16/700,678. [cited by applicant]
Notice of Allowance dated Sep. 16, 2020 U.S. Appl. No. 16/860,589. [cited by applicant]
Wirth et al., “Anti-Inflammatory Properties of Cannabichromene,” Life Sciences, vol. 26, No. 23, 1980, 5 pages. [cited by applicant]
Wright et al., “Cannabinoid CB2 receptors in the gastrointestinal tract: a regulatory system in states of inflammation,” British Journal of Pharmacoloi: iv, vol. 153, 2008, pp. 263-270. [cited by applicant]