IP Library Granted Patent US 10,351,566
Granted Patent B2
US 10,351,566 · App. 16/043,813 · Granted Jul 16, 2019

Therapeutic compounds for pain and synthesis thereof

Inventors: Bart DeCorte (Raritan, NJ); Jacob Cornelis Russcher (Nijmegen, NL); Menno Cornelis Franciscus Monnee (Nijmegen, NL)
Assignee: Janssen Pharmaceutica NV
C07D471/18C07D451/00C07D451/04C07D451/06C07D451/10C07D451/12
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Quick Facts
Patent No.
US 10,351,566
App. No.
16/043,813
Granted
Jul 16, 2019
Kind
B2
Abstract

The invention provides compounds of Formula 1: and stereoisomers, pharmaceutically acceptable salts and derivatives thereof; and methods of making and using such compounds. The invention includes pharmaceutical compositions containing such compounds, and the use of such compounds in methods of treating conditions, diseases, or disorders.

Claims (24)

1. A method of making a compound of Formula 1,

or stereoisomers thereof, wherein the method comprises reacting scopolamine with a reducing agent.

2. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 2,

3. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 3,

4. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 4,

5. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 5,

6. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 6.b,

7. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 7,

8. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 8,

9. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 9,

10. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 10,

11. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 11,

12. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 12,

13. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 12.a,

14. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 13,

15. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 14,

16. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 15,

17. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 16,

18. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 17,

19. The method of claim 1 , wherein the method further comprises reacting a compound of Formula 18,

20. A method of making a compound of Formula 1,

or stereoisomers thereof, comprising reacting scopolamine with sodium borohydrate to form the compound of Formula 1.

21. The method of claim 1 , wherein the method comprises reacting scopolamine with a reducing agent and HCL in isopropyl alcohol.

22. The method of claim 20 , wherein the method comprises reacting scopolamine with sodium borohydrate and HCL in isopropyl alcohol.

Continuity (4)
Continuation 15254952 · Sep 1, 2016
Provisional Application 62214727 · Sep 4, 2015
Provisional Application 62214734 · Sep 4, 2015
Related Publication 20180327405A1 · Nov 15, 2018