You’re using a public version of DrugPatentWatch with 5 free searches available | Register to unlock more free searches. CREATE FREE ACCOUNT

Last Updated: March 28, 2024

Claims for Patent: 4,758,579


✉ Email this page to a colleague

« Back to Dashboard


Summary for Patent: 4,758,579
Title: Fluoroalkoxy substituted benzimidazoles useful as gastric acid secretion inhibitors
Abstract:Dialkoxypyridines of formula I ##STR1## wherein R1 is 1-3C-alkyl which is completely or predominantly substituted by fluorine, or a chlorodifluoromethyl radical and R1' is hydrogen, halo, trifluoromethyl, 1-3C-alkyl, or 1-3C-alkoxy which is optionally completely or predominantly substituted by fluorine, or R1 and R1', together with the oxygen atom to which R1 is bonded, are 1-2C-alkylenedioxy, which is optionally completely or partly substituted by fluorine, or chlorotrifluoroethylenedioxy, R3 is 1-3C-alkoxy, one of R2 and R4 is 1-3C-alkoxy and the other is a hydrogen atom or 1-3C-alkyl and n is 0 or 1, and salts thereof are new compounds with a pronounced protective action on the stomach. Processes for preparing these compounds, medicaments containing them and their use, as well as intermediate compounds and their use for preparing the subject dialkoxypyridines, are disclosed.
Inventor(s): Kohl; Bernhard (Konstanz, DE), Sturm; Ernst (Konstanz, DE), Rainer; Georg (Konstanz, DE)
Assignee: BYK Gulden Lomberg Chemische Fabrik GmbH (Konstanz, DE)
Application Number:07/045,799
Patent Claims: 1. A dialkoxypyridine of formula I ##STR10## wherein R1 is 1-3C-alkyl which is completely or predominantly substituted by fluorine, or chlorodifluoromethyl;

R1' is a hydrogen atom, halo, trifluoromethyl, 1-3C-alkyl, or 1-3C-alkoxy which is unsubstituted or completely or predominatly substituted by fluorine; or

R1 and R1', together with the oxygen atom to which R1 is bonded, is 1-2C-alkylenedioxy which is optionally completely or partly substituted by fluorine, or chlorotrifluoroethylenedioxy;

R3 is 1-3C-alkoxy;

one of R2 and R4 is 1-3C-alkoxy and the other is a hydrogen atom or 1-3C-alkyl; and

n is 0 or 1;

or a salt thereof.

2. A compound according to claim 1 wherein

R1 is 1-3C-alkyl which is completely or predominantly substituted by fluorine, or chlorodifluoromethyl;

R1' is a hydrogen atom, halo, trifluoromethyl, 1-3C-alkyl, or 1-3C-alkoxy which is unsubstituted or completely or predominantly substituted by fluorine;

R3 is 1-3C-alkoxy;

one of R2 and R4 is 1-3C-alkoxy and the other is a hydrogen atom or 1-3C-alkyl; and

n is 0 or 1, or a salt thereof.

3. A compound according to claim 1 wherein,

R1 and R1', together with the oxygen atom to which R1 is bonded, is 1-2C-alkylenedioxy which is unsubstituted or completely or partly substituted by fluorine, or chlorotrifluoroethylenedioxy,

R3 is 1-3C-alkoxy;

one of R2 and R4 is 1-3C-alkoxy and the other is a hydrogen atom or a 1-3C-alkyl radical and

n is 0 or 1, or a salt thereof.

4. A compound according to claim 2, wherein R1' is a hydrogen atom and R1, R2, R3, and R4 and n have their previously-ascribed meanings, or a salt thereof.

5. A compound according to claim 2 wherein R1 is 1,1,2,2-tetrafluoroethyl, trifluoromethyl, 2,2,2-trifluoroethyl, difluoromethyl or chlorodifluoromethyl, R1' is a hydrogen atom, R3 is methoxy, one of R2 and R4 is methoxy and the other is a hydrogen atom or methyl and n is 0 or 1, or a salt thereof.

6. A compound according to claim 2, wherein R1 is 1,1,2,2-tetrafluoroethyl, trifluoromethyl, 2,2,2-trifluoroethyl or difluoromethyl, R1' is a hydrogen atom, R3 is methoxy, one of R2 and R4 is methoxy and the other is a hydrogen atom or methyl and n is 0 or 1, or a salt thereof.

7. A compound according to claim 4, 5, or 6, wherein R2 is a hydrogen atom or methyl and R3 and R4 are methoxy, or a salt thereof.

8. A compound according to claim 4, 5 or 6, wherein R4 is a hydrogen atom and R2 and R3 are methoxy, or a salt thereof.

9. A compound according to claim 3, wherein R1 and R1', together with the oxygen atom to which R1 is bonded, are 1-2C-alkylenedioxy, and R2, R3, R4 and n have the meanings given in claim 3, or a salt thereof.

10. A compound according to claim 3, wherein R1 and R1', together with the oxygen atom to which R1 is bonded, are methylenedioxy or ethylenedioxy, and R2, R3, R4 and n have the meanings given in claim 3, or a salt thereof.

11. A compound according to claim 3, wherein R1 and R1', together with the oxygen atom to which R1 is bonded, are 1-2C-alkylenedioxy which is completely or partly substituted by fluorine and R2, R3, R4 and n have the meanings given in claim 3, or a salt thereof.

12. A compound according to claim 3, wherein R1 and R1', together with the oxygen atom to which R1 is bonded, are difluoromethylenedioxy or 1,1,2-trifluoroethylenedioxy and R2, R3, R4 and n have the meanings given in claim 3, or a salt thereof.

13. A compound according to claim 3 wherein R1 and R1', together with the oxygen atom to which R1 is bonded, are difluoromethylenedioxy or methylenedioxy and R2, R3, R4 and n have the meanings given in claim 3, or a salt thereof.

14. A compound according to claims 9, 10, 11, 12 or 13, wherein R2 is a hydrogen atom or methyl, R3 is methoxy, R4 is methoxy, or a salt thereof.

15. A compound according to claims 9, 10, 11, 12 or 13, wherein R2 is methoxy, R3 is methoxy, and R4 is a hydrogen atom or methyl, or a salt thereof.

16. A compound according to claims 9, 10, 11, 12, or 13, wherein R2 is methoxy, R3 is methoxy and R4 is methyl, or a salt thereof.

17. A compound according to claim 1, wherein n is 0, or an acid addition salt thereof.

18. A compound according to claim 1, wherein n is 1, or a salt thereof with a base.

19. A compound according to claim 1 selected from the group consisting of 2-[(4,5-dimethoxy-2-pyridyl)methylsulfinyl]-5-trifluoromethoxy-1H-benzimid azole, 2-[(4,5-dimethoxy-3-methyl-2-pyridyl)methylsulfinyl]-5-trifluoromethoxy-1H -benzimidazole, 2-[(4,5-dimethoxy-2-pyridyl)methylsulfinyl]-5-(1,1,2,2-tetrafluoroethoxy)- 1H-benzimidazole, 2,2-difluoro-6-[(4,5-dimethoxy-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5- f]benzimidazole and 2,2-difluoro-6-[(4,5-dimethoxy-2-pyridyl)methylsulfinyl]-5H-[1,3]-dioxolo[ 4,5-f]benzimidazole, or a salt thereof.

20. A pharmaceutically-acceptable compound which is a dialkoxypyridine according to claim 1 or a salt thereof.

21. A compound according to claim 1 which is 2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-5-(1,1,2,2-tetrafluoroethoxy)- 1H-benzimidazole or a pharmacologically-compatible salt thereof.

22. A compound according to claim 1 which is 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimida zole or a pharmacologically-compatible salt thereof.

23. A compound according to claim 1 wherein R1 is difluoromethyl, 1,1,2,2-tetrafluoroethyl or 2,2,2-trifluoroethyl; R1' is a hydrogen atom or methoxy; or R1 and R1', together with the oxygen atom to which R1 is bound, is difluoromethylenedioxy or 1,1,2-trifluoroethylenedioxy; R3 is methoxy; one of R2 and R4 is methoxy, and the other is hydrogen; and n is 0 or 1; or a salt thereof.

24. A compound according to claim 1 wherein R1 is difluoromethyl, 1,1,2,2-tetrafluoroethyl or 2,2,2-trifluoroethyl; R1' is a hydrogen atom; R3 is methoxy; one of R2 and R4 is methoxy, and the other is hydrogen; and n is 0 or 1; or a salt thereof.

25. The compound according to claim 1 which is 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimida zole sodium salt.

26. A medicament composition useful to inhibit gastric acid secretion in and to protect the stomach and intestines of warm-blooded animals and comprising an active ingredient and a pharmaceutical auxiliary, the active ingredient comprising from 0.1 to 95 percent by weight of at least one pharmaceutically-acceptable compound according to claim 20.

27. A method for treatment or prophylaxis of illness based on excessive secretion of hydrochloric acid by the stomach which comprises administering an effective amount of a compound according to claim 20 to a mammal suffering from said illness.

28. A method for providing protective action for the stomach and intestines which comprises administering an effective amount of a compound according to claim 20 to a mammal.

Make Better Decisions: Try a trial or see plans & pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.