Quaternary 6,11-dihydro-dibenzo-[b,e]-thiepine-11-N-alkylnorscopine ethers having spasmolytic activity

• US 4,608,377 A
• Filed: 06/25/1984
• Issued: 08/26/1986
• Est. Priority Date: 03/26/1982
• Status: Expired due to Fees

• Current Assignee: Boehringer Ingelheim KG D-6507 Ingelheim Am Rhein
• Original Assignee: Boehringer Ingelheim Promeco SA de CV (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Bauer, Rudolf, Banholzer, Rolf
• Primary Examiner(s): Rotman, Alan L.
• Application Number:
  US06/623,963
• Time in Patent Office: 792 Days
• Field of Search: 546/91, 546/126, 546/124, 514/291
• US Class Current: 514/291
• CPC Class Codes: A61P 1/06 Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/08 Bronchodilators
• CPC Class Codes: A61P 25/02 for peripheral neuropathies
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 451/06 Oxygen atoms
• CPC Class Codes: C07D 451/08 Diarylmethoxy radicals

Abstract

The invention herein relates to novel quaternary 6,11-dihydro-dibenzo-[b,e]-thiepine-11-N-alkylnorscopine ethers, the preparation thereof, and their use as spasmolytics or bronchospasmolytics.

Claims

1. A compound of the formula ##STR6## wherein R is a linear or branched alkyl having from 1 to 10 carbon atoms and

X.sup.(-) is a non-toxic, pharmacologically acceptable anion.

2. The compound of claim 1, wherein R is a linear alkyl having from 1 to 3 carbon atoms or a branched alkyl having 3 carbon atoms.

3. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-11-scopine ether methomethanesulfonate.

4. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-11-scopine ether methobromide.

5. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-11-N-ethylnorscopine ether methobromide.

6. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-11-N-ethylnorscopine ether methomethanesulfonate.

7. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-N-n-propylnorscopine ether methobromide.

8. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-N-n-propylnorscopine ether methomethanesulfonate.

9. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-N-isopropylnorscopine ether methobromide.

10. The compound of claim 1 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-N-isopropylnorscopine ether methomethanesulfonate.

17. A pharmaceutical composition for the treatment of spasms or bronchospasms consisting essentially of an effective amount of a compound of claim 1 and conventional galenic excipients and/or pharmaceutical carrier.

18. A method of treating spasms or bronchospasms which comprises administering perorally, parenterally, or rectally to a host in need of such treatment an effective amount of a compound of claim 1.

11. A compound of the formula ##STR7## or an acid addition salt thereof with an inorganic or organic acid.

12. A compound of claim 11, wherein the acid addition salt is a non-toxic, pharmacologically acceptable acid addition salt.

13. The compound of claim 11 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-11-scopine ether.

14. The compound of claim 11 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-N-ethylnorscopine ether.

15. The compound of claim 11 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-N-n-propylnorscopine ether.

16. The compound of claim 11 which is 6,11-dihydro-dibenzo-[b,e]-thiepine-N-isopropylnorscopine ether.