Long acting bronchodilators for the treatment of respiratory diseases

• US 7,745,621 B2
• Filed: 05/10/2005
• Issued: 06/29/2010
• 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: Grauert, Matthias, Bouyssou, Thierry, Schnapp, Andreas, Breitfelder, Steffen, Lustenberger, Philipp, Pieper, Michael P., Rudolf, Klaus, Speck, Georg
• Primary Examiner(s): Andres; Janet L
• Assistant Examiner(s): Mabry; John
• Application Number:
  US11/125,744
• Publication Number:
  US 20050256114A1
• Time in Patent Office: 1,876 Days
• Field of Search: 514/230.5, 514/304, 544/105
• US Class Current: 544/105
• CPC Class Codes: C07D 265/36 condensed with one six-membered ring

Abstract

The invention relates to compounds of general formula 1

wherein n, A, B, D, L, R¹, R², R³ and R⁴ may have the meanings given in the claims and in the specification, processes for preparing them, and their use 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 n denotes 1, optionally in the form of the individual enantiomers or optionally diastereomers, mixtures of the individual enantiomers or optionally diastereomers or racemates, optionally in the form of the acid addition salts thereof with pharmacologically acceptable acids.

3. The compound of formula 1 according to claim 1, wherein A denotes O (oxygen) or N (nitrogen), optionally in the form of the individual enantiomers or optionally diastereomers, mixtures of the individual enantiomers or optionally diastereomers or racemates, optionally in the form of the acid addition salts thereof with pharmacologically acceptable acids.

4. The compound of formula 1 according to claim 1, wherein B denotes —

CH₂—

O—

, optionally in the form of the individual enantiomers or optionally diastereomers, mixtures of the individual enantiomers or optionally diastereomers or racemates, optionally in the form of the acid addition salts thereof with pharmacologically acceptable acids.

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

L denotes a double-bonded group selected from among —

CO—

(CH₂)_1-6—

, —

CO—

(CH₂)_1-6—

NH—

CO—

(CH₂)_1-4—

, —

CO—

(CH₂)_1-6—

CO—

NH—

(CH₂)_1-4—

, —

CO—

(CH₂)_1-6—

O—

(CH₂)_2-6—

, —

(CH₂)_2-6—

, —

(CH₂)_2-6—

O—

(CH₂)_2-6—

, —

(CH₂)_2-6—

NH—

CO—

(CH₂)_1-4—

, optionally in the form of the individual enantiomers or optionally diastereomers, mixtures of the individual enantiomers or optionally diastereomers or racemates, optionally in the form of the acid addition salts thereof with pharmacologically acceptable acids.

6. The compound of formula 1 according to claim 1, characterised in that they are in the form of one of the acid addition salts thereof with pharmacologically acceptable acids, which is selected from among the hydrochloride, hydrobromide, hydroiodide, hydrosulphate, hydrophosphate, hydromethanesulphonate, hydronitrate, hydromaleate, hydroacetate, hydrobenzoate, hydrocitrate, hydrofumarate, hydrotartrate, hydrooxalate, hydrosuccinate, hydrobenzoate and hydro-p-toluenesulphonate.

7. The compound of formula 1 according to claim 1, characterised in that they are in the form of the R-enantiomers of general formula R-1

8. The compound of formula 1 according to claim 1, characterised in that they are in the form of the regioisomers of general formula Regio-1a

9. The compound of formula 1 according to claim 1, characterised in that they are in the form of the regioisomers of general formula Regio-1b

10. A pharmaceutical composition comprising a compound of formula 1 according to claim 1 and a pharmaceutically acceptable carrier or excipient thereof.

11. A pharmaceutical formulation, characterised in that it contains a compound of formula 1 according to claim 1.

12. An intermediate product of formula 7