IP Library › Granted Patent US 12,365,661
Granted Patent B2
US 12,365,661 · App. 18/371,935 · Granted Jul 22, 2025

Advantageous benzofuran compositions for mental disorders or enhancement

Inventor: Matthew Baggott (Redwood City, CA)
Assignee: Tactogen Inc
C07D307/81A61P25/18A61P25/24
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Quick Facts
Patent No.
US 12,365,661
App. No.
18/371,935
Granted
Jul 22, 2025
Kind
B2
Abstract

Pharmaceutically active benzofuran compositions for the treatment of mental disorders or for mental enhancement, including for entactogenic therapy. The present invention also includes benzofuran compounds, compositions, and methods for generally modulating central nervous system activity and treating central nervous system disorders.

Claims (81)

1. A compound of formula

or a pharmaceutically acceptable salt or mixed salt thereof,

wherein:

R 1 and R 2 are taken together as —OCH═CH— or —CH═CHO—;

R 5A and R 5G are independently selected from the group consisting of —CH 2 OH, —CH 2 X, —CHX 2 , —CX 3 , —CH 2 CH 2 OH, —CH 2 CH 2 X, —CH 2 CHX 2 , —CH 2 CX 3 , C 3 -C 4 cycloalkyl, and C 3 -C 4 alkyl;

R 5F is —CH 2 OH, —CH 2 X, —CHX 2 , —CX 3 , —CH 2 CH 2 OH, —CH 2 CH 2 X, —CH 2 CHX 2 , —CH 2 CX 3 , C 3 -C 4 cycloalkyl, or C 2 -C 4 alkyl;

R 6A , R 6F , and R 6G are independently selected from the group consisting of —H and —CH 3 ;

R A is —CH 3 , —CH 2 Y, —CHY 2 , —CY 3 , —CH 2 CH 3 , —CH 2 CH 2 Y, —CH 2 CHY 2 , —CH 2 CY 3 , —CH 2 OH, or —CH 2 CH 2 OH;

Q is

Y is —F, —Cl, or —Br;

X is —F, —Cl, or —Br; and

Z is O or CH 2 .

2. The compound of claim 1 , wherein the compound is of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

3. The compound of claim 1 , wherein the compound is of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

4. The compound of claim 1 , wherein the compound is of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

5. The compound of claim 1 , wherein the compound is of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

6. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt or mixed salt thereof; wherein R 6A is —H or —CH 3 .

7. The compound of claim 3 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable sat or mixed sat thereof.

8. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt or mixed salt thereof; wherein R 6G is —H or —CH 3 .

9. The compound of claim 6 wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt or mixed salt thereof.

10. The compound of claim 9 wherein the compound is

or a pharmaceutically acceptable salt or mixed salt thereof.

11. The compound of claim 9 wherein the compound is

or a pharmaceutically acceptable salt or mixed salt thereof.

12. The compound of claim 5 , wherein the compound is

or a pharmaceutically acceptable salt or mixed salt thereof.

13. The compound of claim 5 , wherein the compound is

or a pharmaceutically acceptable salt or mixed salt thereof.

14. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt or mixed salt thereof.

15. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt or mixed salt thereof.

16. The compound of claim 15 , wherein the compound is

or a pharmaceutically acceptable salt or mixed salt thereof.

17. The compound of claim 15 , wherein the compound is

or a pharmaceutically acceptable salt or mixed salt thereof.

18. An isolated enantiomerically enriched mixture of formula

or a pharmaceutically acceptable salt or mixed salt thereof,

wherein the isolated enantiomerically enriched mixture comprises between 55% and 90% R-enantiomer or between 55% and 90% S-enantiomer,

wherein:

R 1 and R 2 are taken together as —OCH═CH— or —CH═CHO—;

R 5A and R 5G are independently selected from the group consisting of —CH 2 OH, —CH 2 X, —CHX 2 , —CX 3 , —CH 2 CH 2 OH, —CH 2 CH 2 X, —CH 2 CHX 2 , —CH 2 CX 3 , C 3 -C 4 cycloalkyl, and C 3 -C 4 alkyl;

R 5F is —CH 2 OH, —CH 2 X, —CHX 2 , —CX 3 , —CH 2 CH 2 OH, —CH 2 CH 2 X, —CH 2 CHX 2 , —CH 2 CX 3 , C 3 -C 4 cycloalkyl, or C 2 -C 4 alkyl;

R 6A , R 6F , and R 6G are independently selected from the group consisting of —H and —CH 3 ;

R A is —CH 3 , —CH 2 Y, —CHY 2 , —CY 3 , —CH 2 CH 3 , —CH 2 CH 2 Y, —CH 2 CHY 2 , —CH 2 CY 3 , —CH 2 OH, or —CH 2 CH 2 OH;

Q is;

Y is —F;

X is —F; and

Z is O or CH 2 .

19. The isolated enantiomerically enriched mixture of claim 18 , wherein the isolated enantiomerically enriched mixture has between 55% and 90% S-enantiomer selected from those in a) through e) below:

or a pharmaceutically acceptable salt or a mixed salt thereof.

20. The isolated enantiomerically enriched mixture of claim 18 , wherein the isolated enantiomerically enriched mixture has between 55% and 90% R-enantiomer selected from those in a) through e) below:

or a pharmaceutically acceptable salt or a mixed salt thereof.

21. The isolated enantiomerically enriched mixture of claim 18 of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

22. The isolated enantiomerically enriched mixture of claim 18 of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

23. The isolated enantiomerically enriched mixture of claim 18 of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

24. The isolated enantiomerically enriched mixture of claim 18 of formula

or a pharmaceutically acceptable salt or mixed salt thereof.

25. An isolated enantiomerically enriched mixture of formula:

or a pharmaceutically acceptable salt or mixed salt thereof; wherein R 6A is —H or —CH 3 .

26. The isolated enantiomerically enriched mixture of claim 22 of formula:

or a pharmaceutically acceptable salt or mixed salt thereof.

27. An isolated enantiomerically enriched mixture of formula:

or a pharmaceutically acceptable salt or mixed salt thereof; wherein R 6G is —H or —CH 3 .

28. The isolated enantiomerically enriched mixture of claim 25 of formula:

or a pharmaceutically acceptable salt or mixed salt thereof.

29. The isolated enantiomerically enriched mixture of claim 26 of formula:

or a pharmaceutically acceptable salt or mixed salt thereof.

30. The isolated enantiomerically enriched mixture of claim 27 of formula:

or a pharmaceutically acceptable salt or mixed salt thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 3, 2025
From: BAGGOTT, MATTHEW
To: TACTOGEN INC
Reel/Frame 070729/0596 →
Continuity (10)
Continuation 18077966 · Dec 8, 2022
Continuation PCTUS2021036479 · Jun 8, 2021
Provisional Application 63165731 · Mar 24, 2021
Provisional Application 63149223 · Feb 13, 2021
Provisional Application 63062434 · Aug 6, 2020
Provisional Application 63055897 · Jul 23, 2020
Provisional Application 63048616 · Jul 6, 2020
Provisional Application 63046496 · Jun 30, 2020
Provisional Application 63036382 · Jun 8, 2020
Related Publication 20240083864A1 · Mar 14, 2024
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