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

• US 20070027148A1
• Filed: 10/04/2006
• Published: 02/01/2007
• Est. Priority Date: 05/14/2004
• Status: Active Grant

• Current Assignee: Ingo Konetzki, Peter Sieger, Philipp Lustenberger
• Original Assignee: Ingo Konetzki, Peter Sieger, Philipp Lustenberger
• Inventors: Lustenberger, Philipp, Konetzki, Ingo, Sieger, Peter
• Granted Patent: US 7,491,719 B2
• Time in Patent Office: Days
• US Class Current: 514/230.500
• 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. R-6-Hydroxy-8-{1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamino]ethyl}-4H-benzo [1,4] oxazin-3-one hydrochloride.

2. The anhydride of the compound of claim 1.

11. The compound according to one of claims 1 to 10, wherein the compound is in crystalline form, optionally in the form of their crystalline tautomers.

12. A pharmaceutical composition comprising a compound according to one of claims 1 to 10 and a pharmaceutically acceptable excipient.

3. R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

4. The anhydride of the compound of claim 3.

5. R-8-{2-[2-(3,5-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

6. The anhydride of the compound of claim 5.

7. R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

8. The anhydride of the compound of claim 7.

9. R-8-{2-[2-(4-Fluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

10. The anhydride of the compound of claim 9.