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Claims for Patent: 7,491,719

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Claims for Patent: 7,491,719

Title:Enantiomerically pure beta agonists, process for the manufacture thereof, and use thereof as medicaments
Abstract: Enantiomerically pure compounds of general formula 1 ##STR00001## wherein the groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, and X.sup.- 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.
Inventor(s): Lustenberger; Philipp (Basel, CH), Konetzki; Ingo (Warthausen, DE), Sieger; Peter (Mittelbiberach, DE)
Assignee: Boehringer Ingelheim International GmbH (Ingelheim, DE)
Application Number:11/543,168
Patent 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.

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-h- ydroxy-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-h- ydroxy-4H-benzo[1,4]oxazin-3-one hydrochloride.

10. The anhydride of the compound of claim 9.

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.

13. R-6-Hydroxy-8-{1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamin- o]ethyl}-4H-benzo [1,4]oxazin-3-one in the form of an acid addition salt with an acid HX, wherein X.sup.- denotes an anion with a single negative charge.

14. R-6-Hydroxy-8-{1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamin- o]ethyl}-4H-benzo [1,4]oxazin-3-one according to claim 13, wherein the anion with a single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

15. R-6-Hydroxy-8-{1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamin- o]ethyl}-4H-benzo [1,4]oxazin-3-one according to claim 14, wherein the anion with a single negative charge is chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzote, citrate, salicylate, trifluroacetate, fumarate, tartrate, or succinate.

16. R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl- }-6-hydroxy-4H-benzo [1,4]oxazin-3-one in the form of an acid addition salt with an acid HX, wherein X.sup.- denotes an anion with a single negative charge.

17. R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl- }-6-hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 16, wherein the anion with a single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

18. R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl- }-6-hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 17, wherein the anion with a single negative charge is chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzote, citrate, salicylate, trifluroacetate, fumarate, tartrate, or succinate.

19. R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl- }-6-hydroxy-4H-benzo [1,4]oxazin-3-one in the form of an acid addition salt with an acid HX, wherein X.sup.- denotes an anion with a single negative charge.

20. R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl- }-6-hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 19, wherein the anion with a single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

21. R-8-{2-[2-(2,4-Difluorophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl- }-6-hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 20, wherein the anion with a single negative charge is chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzote, citrate, salicylate, trifluroacetate, fumarate, tartrate, or succinate.

22. R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-- hydroxy-4H-benzo [1,4]oxazin-3-one in the form of an acid addition salt with an acid HX, wherein X.sup.- denotes an anion with a single negative charge.

23. R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-- hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 22, wherein the anion with a single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

24. R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-- hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 23, wherein the anion with a single negative charge is chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzote, citrate, salicylate, trifluroacetate, fumarate, tartrate, or succinate.

25. R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-- hydroxy-4H-benzo [1,4]oxazin-3-one in the form of an acid addition salt with an acid HX, wherein X.sup.- denotes an anion with a single negative charge.

26. R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-- hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 25, wherein the anion with a single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

27. R-8-{2-[2-(4-Ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-- hydroxy-4H-benzo [1,4]oxazin-3-one according to claim 26, wherein the anion with a single negative charge is chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzote, citrate, salicylate, trifluroacetate, fumarate, tartrate, or succinate.
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