Bicyclic compounds

Patent metadata

Field	Value
Publication number	US-10975035-B2
Application number	US-201916379487-A
Country	US
Kind code	B2
Filing date	Apr 9, 2019
Priority date	Sep 17, 2014
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

Disclosed herein are compounds of Formulae (I) and (II), methods of synthesizing compounds of Formulae (I) and (II), and methods of using compounds of Formulae (I) and (II) as an analgesic.

First claim

What is claimed is:

1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

wherein:
R 1 is selected from the group consisting of H, D, an unsubstituted C 1-6 alkyl and an unsubstituted C 1-6 haloalkyl;
R 2 is C(═O)R 2A ;
R 2A is an unsubstituted C 6-30 alkyl or an unsubstituted C 6-30 alkenyl;
R 3 is selected from the group consisting of H, D, halo, a substituted or unsubstituted C 1-8 alkyl, an unsubstituted C 3-4 cycloalkyl, an unsubstituted C 1-8 haloalkyl and an unsubstituted sulfonyl; and
m is 0.

2. The compound of claim 1 , wherein R 1 is H.

3. The compound of claim 1 A, wherein R 2A is an unsubstituted C 6-30 alkyl.

4. The compound of claim 3 , wherein R 2A is selected from the group consisting of —(CH 2 ) 6 CH 3 , —(CH 2 ) 8 CH 3 , —(CH 2 ) 10 CH 3 , —(CH 2 ) 12 CH 3 , —(CH 2 ) 14 CH 3 , —(CH 2 ) 16 CH 3 , —(CH 2 ) 18 CH 3 , —(CH 2 ) 20 CH 3 , —(CH 2 ) 22 CH 3 and —(CH 2 ) 24 CH 3 O.

5. The compound of claim 2 , wherein R 2A is an unsubstituted C 6-30 alkenyl.

6. The compound of claim 2 , wherein R 2A is selected from the group consisting of —(CH 2 ) 7 CH═CH(CH 2 ) 3 CH 3 , —(CH 2 ) 7 CH═CHCH 2 CH═CH(CH 2 ) 4 CH 3 , —(CH 2 ) 7 CH═CH(CH 2 ) 7 CH 3 , —(CH 2 ) 7 CH═CHCH 2 CH═CH(CH 2 ) 4 CH 3 , —(CH 2 ) 7 CH═CH(CH 2 ) 7 CH 3 , —(CH 2 ) 7 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH 3 , —(CH 2 ) 9 CH═CH(CH 2 )CH 3 , —(CH 2 ) 3 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH═CH(CH 2 ) 4 CH 3 , —(CH 2 )CH═CH(CH 2 ) 7 CH 3 , —(CH 2 ) 3 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH 3 , —(CH 2 ) 4 CH═CHCH(CH 3 ) 2 and —(CH 2 ) 2 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH═CHCH 2 CH 3 .

7. The compound of claim 2 , wherein R 3 is H.

8. The compound of claim 2 , wherein R 3 is an unsubstituted C 1-8 alkyl.

9. The compound of claim 8 , wherein R 3 is CH 3 , CH(CH 3 ) 2 or C(CH 3 ) 3 .

10. The compound of claim 2 , wherein R 3 is halo.

11. The compound of claim 10 , wherein R 3 is F or Cl.

12. The compound of claim 2 , wherein R 3 is unsubstituted sulfonyl.

13. The compound of claim 12 , wherein R 3 is S(O) 2 CH 3 .

14. The compound of claim 2 , wherein R 3 is an unsubstituted C 1-8 haloalkyl.

15. The compound of claim 14 , wherein R 3 is CF 3 , CHF 2 or CF 2 CH 3 .

16. The compound of claim 6 , wherein R 3 is H.

17. The compound of claim 6 , wherein R 3 is an unsubstituted C 1-8 alkyl.

18. The compound of claim 17 , wherein R 3 is CH 3 , CH(CH 3 ) 2 or C(CH 3 ) 3 .

19. The compound of claim 6 , wherein R 3 is halo.

20. The compound of claim 19 , wherein R 3 is F or Cl.

21. The compound of claim 6 , wherein R 3 is unsubstituted sulfonyl.

22. The compound of claim 21 , wherein R 3 is S(O) 2 CH 3 .

23. The compound of claim 6 , wherein R 3 is an unsubstituted C 1-8 haloalkyl.

24. The compound of claim 23 , wherein R 3 is CF 3 , CHF 2 or CF 2 CH 3 .

25. The compound of claim 1 , wherein the compound of Formula (I) is selected from the group consisting of:

or a pharmaceutically acceptable salt of any of the foregoing.

Assignees

• Recurium Ip Holdings Llc

Inventors

• Bunker Kevin Duane
• Guo Chuangxing
• Grier Mark Charles
• Hopkins Chad Daniel
• Pinchman Joseph Robert
• Slee Deborah Helen
• Huang Peter Qinhua
• Kahraman Mehmet

Classifications

• C07C233/09

  with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton · CPC title

• C07C233/05

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C215/42

  having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton · CPC title

• C07C211/38

  containing condensed ring systems · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title