Therapeutic compounds for pain and synthesis thereof

Patent metadata

Field	Value
Publication number	US-10358448-B2
Application number	US-201816043829-A
Country	US
Kind code	B2
Filing date	Jul 24, 2018
Priority date	Sep 4, 2015
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

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.

First claim

What is claimed is:

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.

Assignees

• Janssen Pharmaceutica Nv

Inventors

• Decorte Bart
• Russcher Jacob Cornelis
• Monnee Menno Cornelis Franciscus

Classifications

• A61P29/02

  without antiinflammatory effect · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• A61P25/04

  Centrally acting analgesics, e.g. opioids · CPC title

• A61P25/02

  for peripheral neuropathies · CPC title

• C07D451/00

  Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof · CPC title