Anticholinergics which may be used as medicaments as well as processes for preparing them

• US 20040087617A1
• Filed: 10/14/2003
• Published: 05/06/2004
• Est. Priority Date: 10/14/2000
• Status: Abandoned Application

• Current Assignee: Boehringer Ingelheim Pharma GmbH & Company Kg (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim Pharma GmbH & Company Kg (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Pieper, Michael Paul, Meissner, Helmut, Banholzer, Rolf, Speck, Georg, Pohl, Gerald, Morschhaeuser, Gerd, Reichl, Richard
• Application Number:
  US10/684,994
• Publication Number:
  US 20040087617A1
• Time in Patent Office: Days
• US Class Current: 514/304
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 451/10 acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine

Abstract

The present invention relates to new anticholinergics of general formula 1

wherein A, X⁻, and the groups R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ may have the meanings given in the claims and in the specification, processes for preparing them and their use as pharmaceutical compositions.

Claims

1. A compound of formula 1

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

X⁻

is an anion with a single negative charge selected from chloride, bromide, methylsulfate, 4-toluenesulfonate, and methanesulfonate;

R¹ and R², which are identical or different, are each a group selected from methyl, ethyl, n-propyl, and isopropyl, which are optionally substituted by hydroxy or fluorine;

R³, R⁴, R⁵, and R⁶, which are identical or different, are each hydrogen, methyl, ethyl, methyloxy, ethyloxy, hydroxy, fluorine, chlorine, bromine, CN, CF₃, or NO₂; and

R⁷ is methyl, ethyl, methyloxy, ethyloxy, —

CH₂—

F, —

CH₂—

CH₂—

F, —

O—

CH₂—

F, —

O—

CH₂—

CH₂—

F, —

CH₂—

OH, —

CH₂—

CH₂—

OH, CF₃, —

CH₂—

OMe, —

CH₂—

CH₂—

OMe, —

CH₂—

OEt, —

CH₂—

CH₂OEt, —

O—

COMe, —

O—

COEt, —

O—

COCF₃, —

O—

COCF₃, fluorine, chlorine, or bromine.

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

X⁻

is an anion with a single negative charge selected from chloride, bromide, and methanesulfonate;

R¹ and R², which are identical or different, are each methyl or ethyl, which are optionally substituted by hydroxy or fluorine;

R³, R⁴, R⁵, and R⁶, which are identical or different, are each hydrogen, methyl, ethyl, methyloxy, ethyloxy, hydroxy, fluorine, chlorine, or bromine; and

R⁷ is methyl, ethyl, methyloxy, ethyloxy, CF₃, or fluorine.

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

X⁻

is bromide;

R¹ and R², which are identical or different, are each methyl or ethyl;

R³, R⁴, R⁵, and R⁶, which are identical or different, are each hydrogen, methyl, methyloxy, chlorine, or fluorine; and

R⁷ is methyl or fluorine.

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

X⁻

is bromide;

R¹ and R², which are identical or different, are each methyl or ethyl;

R³, R⁴, R⁵, and R⁶, which are identical or different, denote hydrogen or fluorine; and

R⁷ is methyl or fluorine.

6. A method of treating a disease that is responsive to anticholinergic activity, comprising administering to a host in need thereof an effective amount of a compound of formula 1 according to one of claims 1 to 5.

7. A method according to claim 6, wherein the disease is selected from asthma, COPD, vagally induced sinus bradycardia, heart rhythm disorders, spasms in the gastrointestinal tract, spasms in the urinary tract, and menstrual disorders.

8. A pharmaceutical composition comprising one or more compounds of formula 1 according to one of claims 1 to 5, or a physiologically acceptable salt thereof, optionally together with one or more conventional excipients and/or carriers.

9. A pharmaceutical composition according to claim 8, further comprising at least one additional active substance selected from the group consisting of:

betamimetics, antiallergic agents, PAF-antagonists, leukotriene-antagonists, and steroids.

10. A process for preparing a compound of formula 1 according to claim 1

11. A compound of formula 4