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

• US 7,220,742 B2
• Filed: 05/12/2005
• Issued: 05/22/2007
• 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:
  US11/128,032
• Publication Number:
  US 20050267106A1
• Time in Patent Office: 740 Days
• Field of Search: 544/105, 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

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. A compound of formula 1

2. The compound of formula 1 according to claim 1, wherein:

R¹ is hydrogen or halogen;

R² is hydrogen or halogen;

R³ is hydrogen, C₁–

C₄-alkoxy, or halogen;

R⁴ is hydrogen or halogen; and

X⁻

is an anion with a single negative charge,

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

3. The compound of formula 1 according to claim 1, wherein:

R¹ is hydrogen, fluorine, or clorine;

R² is hydrogen, fluorine, or clorine;

R³ is hydrogen, methoxy, ethoxy, fluorine, or chlorine;

R⁴ is hydrogen, fluorine, or chlorine; and

X⁻

is an anion with a single negative charge,

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

4. The compound of formula 1 according to claim 1, wherein:

R¹ is hydrogen or fluorine;

R² is hydrogen;

R³ is methoxy, ethoxy, or fluorine;

R⁴ is hydrogen; and

X⁻

is chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzote, citrate, salicylate, trifluroacetate, fumarate, tartrate, or succinate;

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

5. The compound of formula 1 according to claim 1, wherein:

R¹ is hydrogen;

R² is hydrogen, fluorine, or chlorine;

R³ is hydrogen;

R⁴ is hydrogen, fluorine, or chlorine;

X⁻

is chloride, bromide, sulphate, methanesulphonate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, or succinate;

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

6. The compound of formula 1 according to claim 1, wherein the compound is in crystalline form, optionally in the form of their crystalline tautomers, crystalline hydrates, or crystalline solvates.

7. A pharmaceutical composition comprising the compound of formula 1 according to claim 1 and a pharmaceutically acceptable carrier.

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

11. The compound according to claim 1, wherein the anion with the single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, malcate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

12. The compound according to claim 2, wherein the anion with the single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

13. The compound according to claim 3, wherein the anion with the single negative charge is chloride, bromide, iodide, sulphate, phosphate, methanesuiphonate, nitrate, maleate, acetate, benzoate, citrate, salicylate, trifluoroacetate, fumarate, tartrate, oxalate, succinate, or p-toluenesulphonate.

14. A method for the treatment of respiratory complaints comprising administering to a patient in need thereof a therapeutically effective amount of the compound of formula 1 according to claim 2.

15. A method for the treatment of respiratory complaints comprising administering to a patient in need thereof a therapeutically effective amount of the compound of formula 1 according to claim 3.

16. A method for the treatment of respiratory complaints comprising administering to a patient in need thereof a therapeutically effective amount of the compound of formula 1 according to claim 4.

17. A method for the treatment of respiratory complaints comprising administering to a patient in need thereof a therapeutically effective amount of the compound of formula 1 according to claim 5.

18. A method for the treatment of respiratory complaints comprising administering to a patient in need thereof a therapeutically effective amount of the compound of formula 1 according to claim 6.

9. A compound of formula 5

10. A compound of formula 7