Quaternary N-.beta.-substituted N-alkyl-nortropine benzilates

• US 4,042,700 A
• Filed: 09/03/1976
• Issued: 08/16/1977
• Est. Priority Date: 09/12/1975
• Status: Expired due to Term

• Current Assignee: Boehringer Ingelheim GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Bauer, Rudolf, Schulz, Werner, Banholzer, Rolf, Heusner, Alex
• Primary Examiner(s): Rotman, Alan L.
• Application Number:
  US05/720,245
• Time in Patent Office: 347 Days
• Field of Search: 260/292, 424/265
• US Class Current: 514/304
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/08 Bronchodilators
• CPC Class Codes: C07D 451/02 containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
• CPC Class Codes: C07D 451/10 acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine

Abstract

Compounds of the formula ##STR1## wherein ONE OF R and R'"'"' is alkyl of 1 to 4 carbon atoms,

The other of R and R'"'"' is β-haloethyl or β-hydroxyethyl, and

X is a pharmacologically acceptable anion, preferably halogen;

The compounds as well as the salts are useful as spasmolytics, bronchospasmolytics and inhibitors of excessive stomach juice secretion.

Claims

1. A compound of the formula ##STR4## wherein one of R and R'"'"' is alkyl of 1 to 4 carbon atoms,

the other of R and R'"'"' is β

-haloethyl or β

-hydroxyethyl, and

3. A compound of claim 1, where

one of R and R'"'"' is alkyl of 1 to 4 carbon atoms,

the other of R and R'"'"' is β

-haloethyl or β

-hydroxyethyl, and

X is halogen.

4. A compound of claim 1, where

R is alkyl of 1 to 4 carbon atoms,

R'"'"' is β

-haloethyl or β

-hydroxyethyl, and

X is halogen.

5. A compound of claim 1, where

R is alkyl of 1 to 4 carbon atoms,

R'"'"' is β

-fluoroethyl, and

X is halogen.

6. The compound of claim 1 which is N-β

-fluoroethyl-nortropine benzilate methobromide.

8. A compound of claim 1, which is N-β

-fluoroethyl-nortropine benzilate or a non-toxic, pharmacologically acceptable acid addition salt thereof.

9. A spasmolytic or bronchospasmolytic pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective spasmolytic or bronchospasmolytic amount of a compound of claim 1.

10. A spasmolytic pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective spasmolytic amount of a compound of claim 6.

11. The method of alleviating spasms or bronchospasms in a warm-blooded animal, which comprises administering to said animal an effective spasmolytic or bronchospasmolytic amount of a compound of claim 1.

12. The method of alleviating spasms in a warm-blooded animal, which comprises administering to said animal an effective spasmolytic amount of a compound of claim 6.

2. X is a pharmacologically acceptable anion.

7. A compound of the formula ##STR5## wherein R₁ is β

-hydroxyethyl or β

-haloethyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.