Enantiomerically pure beta agonists, process for the manufacture thereof and use thereof as medicaments

• US 8,034,809 B2
• Filed: 12/15/2008
• Issued: 10/11/2011
• Est. Priority Date: 05/14/2004
• Status: Active Grant

• Current Assignee: Boehringer Ingelheim International GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim International GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Lustenberger, Philipp, Konetzki, Ingo, Sieger, Peter
• Primary Examiner(s): HABTE, KAHSAY
• Application Number:
  US12/335,076
• Publication Number:
  US 20090137578A1
• Time in Patent Office: 1,030 Days
• Field of Search: 514/230.5
• US Class Current: 514/230.5
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: C07D 265/36 condensed with one six-membered ring
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond

Abstract

Enantiomerically pure compounds of general formula 1

wherein the groups R¹, R², R³, R⁴, and X⁻ may have the meanings given in the claims and in the specification, processes for preparing them and the use thereof as pharmaceutical compositions, particularly as pharmaceutical compositions for the treatment of respiratory complaints.

Claims

1. A method for the treatment of respiratory complaints comprising administering to a patient a therapeutically effective amount of R-6-Hydroxy-8-{1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamino]ethyl}-4H-benzo[1,4]oxazin-3-one hydrochloride.

2. The method according to claim 1, wherein the treatment is once-a-day.

3. The method according to claim 1, wherein said respiratory complaint is COPD (chronic obstructive pulmonary disease).

4. The method according to claim 3, wherein the treatment is once-a-day.

5. The method according to claim 1, wherein said respiratory complaint is asthma.

6. The method according to claim 5, wherein the treatment is once-a-day.

7. The method according to claim 1, wherein said respiratory complaints are selected from the group consisting of bronchial asthma, paediatric asthma, severe asthma, acute asthma attacks and chronic bronchitis.

8. The method according to claim 7, wherein the treatment is once-a-day.

9. A method for the treatment of respiratory complaints comprising administering to a patient a therapeutically effective amount of R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

10. The method according to claim 9, wherein the treatment is once-a-day.

11. The method according to claim 9, wherein said respiratory complaint is COPD (chronic obstructive pulmonary disease).

12. The method according to claim 11, wherein the treatment is once-a-day.

13. The method according to claim 9, wherein said respiratory complaint is asthma.

14. The method according to claim 13, wherein the treatment is once-a-day.

15. The method according to claim 9, wherein said respiratory complaints are selected from the group consisting of bronchial asthma, paediatric asthma, severe asthma, acute asthma attacks and chronic bronchitis.

16. The method according to claim 15, wherein the treatment is once-a-day.

17. A method for the treatment of respiratory complaints comprising administering to a patient a therapeutically effective amount of R-8-{2-[2-(3,5-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

18. The method according to claim 17, wherein the treatment is once-a-day.

19. The method according to claim 17, wherein said respiratory complaint is COPD (chronic obstructive pulmonary disease).

20. The method according to claim 19, wherein the treatment is once-a-day.

21. The method according to claim 17, wherein said respiratory complaint is asthma.

22. The method according to claim 21, wherein the treatment is once-a-day.

23. The method according to claim 17, wherein said respiratory complaints are selected from the group consisting of bronchial asthma, paediatric asthma, severe asthma, acute asthma attacks and chronic bronchitis.

24. The method according to claim 23, wherein the treatment is once-a-day.

25. A method for the treatment of respiratory complaints comprising administering to a patient a therapeutically effective amount of R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

26. The method according to claim 25, wherein the treatment is once-a-day.

27. The method according to claim 25, wherein said respiratory complaint is COPD (chronic obstructive pulmonary disease).

28. The method according to claim 27, wherein the treatment is once-a-day.

29. The method according to claim 25, wherein said respiratory complaint is asthma.

30. The method according to claim 29, wherein the treatment is once-a-day.

31. The method according to claim 25, wherein said respiratory complaints are selected from the group consisting of bronchial asthma, paediatric asthma, severe asthma, acute asthma attacks and chronic bronchitis.

32. The method according to claim 31, wherein the treatment is once-a-day.

33. A method for the treatment of respiratory complaints comprising administering to a patient a therapeutically effective amount of R-8-{2-[2-(4-Fluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

34. The method according to claim 33, wherein the treatment is once-a-day.

35. The method according to claim 33, wherein said respiratory complaint is COPD (chronic obstructive pulmonary disease).

36. The method according to claim 35, wherein the treatment is once-a-day.

37. The method according to claim 33, wherein said respiratory complaint is asthma.

38. The method according to claim 37, wherein the treatment is once-a-day.

39. The method according to claim 33, wherein said respiratory complaints are selected from the group consisting of bronchial asthma, paediatric asthma, severe asthma, acute asthma attacks and chronic bronchitis.

40. The method according to claim 39, wherein the treatment is once-a-day.