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

• US 20050267106A1
• Filed: 05/12/2005
• Published: 12/01/2005
• 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
• Granted Patent: US 7,220,742 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

The present invention relates to 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. ) An enantiomerically pure compounds of formula 1

2. ) The enantiomerically pure compounds of formula 1 according to claim 1, wherein

R¹ denotes hydrogen or halogen;

R² denotes hydrogen or halogen;

R³ denotes hydrogen, C₁-C₄-alkoxy or halogen;

R⁴ denotes hydrogen or halogen;

X⁻

denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate,

optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.

3. ) The enantiomerically pure compounds of formula 1 according to claim 1, wherein

R¹ denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;

R² denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;

R³ denotes hydrogen, methoxy, ethoxy, fluorine or chlorine, preferably hydrogen, methoxy, ethoxy or fluorine;

R⁴ denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;

X⁻

denotes an anion with a single negative charge, preferably an anion with a single negative charge selected from among chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, benzoate and p-toluenesulphonate,

optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.

4. ) The enantiomerically pure compounds of formula 1 according to claim 1, wherein

R¹ denotes hydrogen or fluorine;

R² denotes hydrogen;

R³ denotes methoxy, ethoxy or fluorine;

R⁴ denotes hydrogen;

X⁻

denotes an anion with a single negative charge selected from among chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate and succinate;

optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.

5. ) The enantiomerically pure compounds of formula 1 according to claim 1, wherein

R¹ denotes hydrogen;

R² denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;

R³ denotes hydrogen;

R⁴ denotes hydrogen, fluorine or chlorine, preferably hydrogen or fluorine;

X⁻

denotes an anion with a single negative charge selected from among chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate and succinate;

optionally in the form of the tautomers, mixtures of the tautomers, hydrates or solvates thereof.

6. ) The enantiomerically pure compounds of formula 1 according to claim 1, characterised in that they are in crystalline form, optionally in the form of their crystalline tautomers, crystalline hydrates or crystalline solvates.

7. ) A pharmaceutical composition comprising the enantiomerically pure compounds of formula 1 according to claim 1.

8. ) A method for the treatment of respiratory complaints comprising administering to a patient in need thereof a therapeutically effective amount of the enantiomerically pure compounds of formula 1 according to claim 1.

10. ) A compound of formula 7

11. ) A compound of formula 1′

9. ) A compound of formula 5