IP Library Granted Patent US 12,419,872
Granted Patent B2
US 12,419,872 · App. 17/670,264 · Granted Sep 23, 2025

Low-temperature synthesis of thymoquinone and harmaline compounds

Inventors: Gene H. Zaid (Hutchinson, KS); Beth Ann Wolf (Hutchinson, KS); Rachel Elizabeth Ropp (Hutchinson, KS); Krishna Mohan Donavalli (Sterling, KS); Rajni Verma (Sterling, KS)
Assignee: Ankh Life Sciences Limited
A61K31/437
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Quick Facts
Patent No.
US 12,419,872
App. No.
17/670,264
Granted
Sep 23, 2025
Kind
B2
Abstract

Low-temperature syntheses of thymoquinone/harmaline compounds which are useful for the treatment of human diabetes and cancers, and the derivatives, solvates, prodrugs, isomers, and tautomers of such compounds.

Claims (11)

1. A composition comprising one or more of the following compounds, and the isomers, tautomers, solvates, esters, metal complexes, and salts thereof:

2. The composition of claim 1 , said compound having a molecular weight of about 360 or about 378.

3. A method of treating a human suffering from cancer and/or diabetes, said method comprising administering a therapeutically-effective amount of a composition according to claim 1 to a human in need thereof.

4. The method of claim 3 , said human being a diabetic patient.

5. The method of claim 3 , said human being a cancer patient.

6. The method of claim 5 , wherein said cancer patient is suffering from lymphoma.

7. A process for preparing a composition according to claim 1 , said method comprising reacting harmaline and thymoquinone in a non-interfering solvent and carrying out the reaction between said thymoquinone and harmaline at a temperature of less than about 10° C. for at least 4 hours.

8. The process of claim 7 , said reacting step comprises mixing together thymoquinone and harmaline in a noninterfering solvent to yield a reaction mixture and allowing said reaction mixture to stand at a temperature of less than about 10° C. for a time period of at least 4 hours.

9. The process of claim 8 , wherein said reaction is carried out a temperature of less than about 0° C. for a time period from about 6 hours to about 100 hours.

10. The process of claim 8 , wherein said thymoquinone and harmaline are mixed together in a weight ratio of from about 1:0.1 to about 1:2.

11. The process of claim 8 , wherein said reaction is carried out a temperature of from about −18° C. to about −100° C. for a time period from about 6 hours to about 100 hours.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2022
From: ZAID, GENE H.; WOLF, BETH ANN; ROPP, RACHEL ELIZABETH
To: ANKH LIFE SCIENCES LIMITED
Reel/Frame 058994/0175 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2022
From: DONAVALLI, KRISHNA MOHAN; VERMA, RAJNI
To: ANKH LIFE SCIENCES LIMITED
Reel/Frame 058994/0192 →
Continuity (2)
Continuation In Part 16810291 · Mar 5, 2020
Related Publication 20220160685A1 · May 26, 2022
References Cited (21)
US 2616893A · Newby · 1952 [cited by applicant]
US 5304658A · Terao et al. · 1994 [cited by applicant]
US 9630899B1 · Huang et al. · 2017 [cited by applicant]
US 10875859B2 · Zaid · 2020 [cited by examiner]
US 11358963B2 · Zaid · 2022 [cited by examiner]
US 11452715B2 · Zaid · 2022 [cited by examiner]
US 11453664B2 · Zaid · 2022 [cited by examiner]
US 11453665B2 · Zaid · 2022 [cited by examiner]
US 20150037308A1 · Ikemoto et al. · 2015 [cited by applicant]
US 20190315742A1 · Zaid et al. · 2019 [cited by applicant]
US 20200101050A1 · Zaid et al. · 2020 [cited by applicant]
US 20200102305A1 · Zaid et al. · 2020 [cited by applicant]
US 20200102306A1 · Zaid et al. · 2020 [cited by applicant]
WO 2016064676A1 · 2016 [cited by applicant]
WO 2019200107A1 · 2019 [cited by applicant]
International Search Report and Written Opinion in PCT/US2021/020847, filed Mar. 4, 2021. [cited by applicant]
Office Action dated Apr. 1, 2020 in U.S. Appl. No. 16/380,279, now U.S. Pat. No. 10,875,859 issued Dec. 29, 2020. [cited by applicant]
Office Action dated Aug. 27, 2020 in U.S. Appl. No. 16/380,279, now U.S. Pat. No. 10,875,859 issued Dec. 29, 2020. [cited by applicant]
Office Action dated Dec. 17, 2021 in U.S. Appl. No. 16/701,554, now U.S. Pat. No. 11,453,664 issued Sep. 27, 2022. [cited by applicant]
Office Action dated Dec. 17, 2021 in U.S. Appl. No. 16/701,581, now U.S. Pat. No. 11,453,665 issued Sep. 27, 2022. [cited by applicant]
Office Action dated Dec. 16, 2021 in U.S. Appl. No. 16/701,597, now U.S. Pat. No. 11,452,715 issued Sep. 27, 2022. [cited by applicant]