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Last Updated: December 19, 2025

Claims for Patent: 9,309,234


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Summary for Patent: 9,309,234
Title:Opioid receptor ligands and methods of using and making same
Abstract:This application describes compounds that can act as opioid receptor ligands, which compounds can be used in the treatment of, for example, pain and pain related disorders.
Inventor(s):Dennis Yamashita, Dimitar Gotchev, Philip Pitis, Xiao-Tao Chen, Guodong Liu, Catherine C. K. Yuan
Assignee:Trevena Inc
Application Number:US14/712,974
Patent Claims: 1. A compound having a formula of or a pharmaceutically acceptable salt thereof, wherein: R21 and R22 are independently H or CH3; D1 is an optionally substituted aryl; B3 is H or optionally substituted alkyl; and B5 is an optionally substituted thiophenyl.

2. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein D1 is an optionally substituted phenyl or an optionally substituted pyridyl.

3. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein D1 is pyridyl.

4. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein D1 is 2-pyridyl.

5. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein B5 is an optionally substituted thiophenyl selected from the group consisting of

6. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein B5 is wherein R23, R24, and R30 are each independently H, OH, cycle, aryl, branched or unbranched alkyl alcohol, halo, branched or unbranched alkyl, amide, cyano, alkoxy, haloalkyl, aklylsulfonyl, nitrite, alkylsulfanyl; or R23 and R24 together form an aryl or cycle that is attached to one or more of the atoms of B5.

7. The compound of claim 6, or a pharmaceutically acceptable salt thereof, wherein R23, R24, and R30 are each independently H, NH2, OH, Cl, Br, F, I, OMe, CN, CH3, phenyl, C3-C6 carbocycle, methanesulfonyl, CF3, wherein R29 is H or an optionally substituted branched or unbranched alkyl.

8. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein B5 is wherein R23 and R24 are each independently H, OH, cycle, aryl, branched or unbranched alkyl alcohol, halo, branched or unbranched alkyl, amide, cyano, alkoxy, haloalkyl, aklylsulfonyl, nitrite, alkylsulfanyl; or R23 and R24 together form an aryl or cycle that is attached to one or more of the atoms of B5.

9. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein B5 is wherein R23 is H, OH, cycle, aryl, branched or unbranched alkyl alcohol, halo, branched or unbranched alkyl, amide, cyano, alkoxy, haloalkyl, aklylsulfonyl, nitrite, or alkylsulfanyl.

10. The compound of claim 9, or a pharmaceutically acceptable salt thereof, wherein R23 is alkoxy.

11. The compound of claim 10, or a pharmaceutically acceptable salt thereof, wherein R23 is methoxy.

12. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein B3 is H or C1-C5 alkyl.

13. The compound of claim 1 having a formula of or a pharmaceutically acceptable salt thereof, wherein D1 is an optionally substituted aryl; B3 is H or optionally substituted alkyl B5 is an optionally substituted thiophenyl.

14. The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein D1 is an optionally substituted phenyl or an optionally substituted pyridyl.

15. The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein D1 is pyridyl.

16. The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein D1 is 2-pyridyl.

17. The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein B5 is wherein R23 and R24 are each independently H, OH, cycle, aryl, branched or unbranched alkyl alcohol, halo, branched or unbranched alkyl, amide, cyano, alkoxy, haloalkyl, aklylsulfonyl, nitrite, alkylsulfanyl; or R23 and R24 together form an aryl or cycle that is attached to one or more of the atoms of B5.

18. The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein B5 is wherein R23 is H, OH, cycle, aryl, branched or unbranched alkyl alcohol, halo, branched or unbranched alkyl, amide, cyano, alkoxy, haloalkyl, aklylsulfonyl, nitrite, or alkylsulfanyl.

19. The compound of claim 18, or a pharmaceutically acceptable salt thereof, wherein R23 is alkoxy.

20. The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein B3 is H or C1-C5 alkyl.

21. The compound of claim 15, or a pharmaceutically acceptable salt thereof, wherein B3 is H or C1-C5 alkyl.

22. The compound of claim 21, or a pharmaceutically acceptable salt thereof, wherein B5 is wherein R23 is H, OH, cycle, aryl, branched or unbranched alkyl alcohol, halo, branched or unbranched alkyl, amide, cyano, alkoxy, haloalkyl, aklylsulfonyl, nitrite, or alkylsulfanyl.

23. The compound of claim 22, or a pharmaceutically acceptable salt thereof, wherein R23 is alkoxy.

24. The compound of claim 23, or a pharmaceutically acceptable salt thereof, wherein R23 is methoxy.

25. A pharmaceutically acceptable salt of a compound having a formula of

26. The pharmaceutically acceptable salt of claim 25, wherein the salt is a pharmaceutically acceptable salt of a compound having a formula of

27. A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof, and pharmaceutically acceptable carrier.

28. A pharmaceutical composition comprising a compound of claim 13, or a pharmaceutically acceptable salt thereof, and pharmaceutically acceptable carrier.

29. A method of treating pain comprising administering to a subject the compound of claim 1, or a pharmaceutically acceptable salt thereof.

30. A method of treating pain comprising administering to a subject the compound of claim 13, or a pharmaceutically acceptable salt thereof.

31. A method of treating pain comprising administering to a subject or a subject in need thereof the pharmaceutically acceptable salt of claim 25.

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