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 29, 2024

Claims for Patent: 4,255,431


✉ Email this page to a colleague

« Back to Dashboard


Summary for Patent: 4,255,431
Title: Gastric acid secretion inhibiting substituted 2-(2-benzimidazolyl)-pyridines, pharmaceutical preparations containing same, and method for inhibiting gastric acid secretion
Abstract:The present invention relates to novel compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are each hydrogen, alkyl, halogen, carbomethoxy, carbethoxy, alkoxy, or alkanoyl, R.sup.6 is hydrogen, methyl or ethyl, R.sup.3, R.sup.4 and R.sup.5 are the same or different and are each hydrogen, methyl, methoxy, ethoxy, methoxyethoxy or ethoxyethoxy whereby R.sup.3, R.sup.4 and R.sup.5 are not all hydrogen, and whereby when two of R.sup.3, R.sup.4 and R.sup.5 are hydrogen the third of R.sup.3, R.sup.4 and R.sup.5 is not methyl. The compounds are potent gastric acid secretion inhibitors.
Inventor(s): Junggren; Ulf K. (Molnlycke, SE), Sjostrand; Sven E. (Kungsbacka, SE)
Assignee: Aktiebolaget Hassle (Molndal, SE)
Application Number:06/027,277
Patent Claims: 1. A method of inhibiting gastric acid secretion by administering to mammals, including man, suffering from gastric acid secretion disturbances a compound of the formula III ##STR13## or a pharmaceutically acceptable salt thereof in a therapeutically effective amount in which R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, lower alkyl, halogen, carbomethoxy, carbethoxy, lower alkoxy, and lower alkanoyl in any position, R.sup.6 is selected from the group consisting of hydrogen, methyl, and ethyl, R.sup.3, and R.sup.5 are the same or different and are each selected from the group consisting of hydrogen, methyl, methoxy, ethoxy, methoxyethoxy, and ethoxyethoxy; and R.sup.4 is methoxy, ethoxy, methoxyethoxy and ethoxyethoxy.

2. A method according to claim 1, wherein a compound of formula III or a pharmaceutically acceptable salt thereof in a therapeutically effective amount in which R.sup.1 is hydrogen, chloro, methyl, ethyl, methoxy, acetyl, carbethoxy or carbomethoxy, R.sup.2 is hydrogen, or methyl, R.sup.6 is hydrogen, methyl or ethyl, R.sup.3 and R.sup.5 are methyl, and R.sup.4 is methoxy, is administered.

3. A method according to claim 1, wherein a compound of formula III or a pharmaceutically acceptable salt thereof is a therapeutically effective amount in which R.sup.1 is hydrogen, chloro, methyl, ethyl, acetyl, methoxy, carbethoxy or carbomethoxy, and R.sup.2 is hydrogen, methyl, or ethyl, R.sup.6 is hydrogen, methyl or ethyl, R.sup.4 is methoxy and R.sup.3 is hydrogen and R.sup.5 is methyl, or R.sup.3 is methyl and R.sup.5 is hydrogen.

4. A method according to claim 1, wherein a compound of formula III selected from the group consisting of

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazole,

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(4,6-dimethyl)-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-be nzimidazole,

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzimida zole,

2-[2-(4-ethoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzimidaz ole,

2-[2-(3-methyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)- benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-meth yl)-benzimidazole,

2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-carbomethyoxy-6-methyl) -benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-5-carbomethoxy)-benzim idazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl)-benzimidazo le,

2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-methoxy)-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methoxy)-benzimidaz ole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methyl)-benzimidazo le,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-chloro)-benzimidazo le or a pharmaceutically acceptable salt thereof in a therapeutically effective amount is administered for inhibiting gastric acid secretion.

5. A compound of formula III ##STR14## or a pharmaceutically acceptable salt thereof in which R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, lower alkyl, halogen, carbomethoxy, carbethoxy, lower alkoxy and lower alkanoyl in any position, R.sup.6 is selected from the group consisting of hydrogen, methyl, and ethyl, R.sup.3, and R.sup.5 are the same or different and are each selected from the group consisting of hydrogen, methyl, methoxy, ethoxy, methoxyethoxy, and ethoxyethoxy, and R.sup.4 is methoxy, ethoxy, methoxyethoxy and ethoxyethoxy, whereby R.sup.3, R.sup.4, and R.sup.5 are not all hydrogen.

6. A compound according to claim 5 or a pharmaceutically acceptable salt thereof in which R.sup.1 is hydrogen, chloro, methyl, ethyl, methoxy, acetyl, carbethoxy or carbomethoxy, R.sup.2 is hydrogen, or methyl, R.sup.6 is hydrogen, methyl, or ethyl, R.sup.3 and R.sup.5 are methyl, and R.sup.4 is methoxy, is administered.

7. A compound according to claim 5 or a pharmaceutically acceptable salt thereof in which R.sup.1 is hydrogen, chloro, methyl, ethyl, acetyl, methoxy, carbethoxy or carbomethoxy, and R.sup.2 is hydrogen, methyl, or ethyl, R.sup.6 is hydrogen, methyl or ethyl, R.sup.4 is methoxy and R.sup.3 is hydrogen and R.sup.5 is methyl, or R.sup.3 is methyl and R.sup.5 is hydrogen.

8. A compound selected from the group consisting of

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazole,

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(4,6-dimethyl)-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-be nzimidazole,

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzimida zole,

2-[2-(4-ethoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzimidaz ole,

2-[2-(3-methyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)- benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-meth yl)-benzimidazole,

2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)- benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy)-benzi midazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl)-benzimidazo le,

2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-methoxy)-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methoxy)-benzimidaz ole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methyl)-benzimidazo le,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-chloro)-benzimidazo le.

9. A pharmaceutical preparation for inhibiting a gastric acid secretion which contains as an active agent a compound of the formula III ##STR15## or a pharmaceutically acceptable non-toxic acid addition salt thereof in an amount effective to inhibit gastric acid secretion in a mammal in which R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, lower alkyl, halogen, carbomethoxy, carbethoxy, lower alkoxy, and lower alkanoyl in any position, R.sup.6 is selected from the group consisting of hydrogen, methyl, and ethyl, R.sup.3, and R.sup.5 are the same or different and are each selected from the group consisting of hydrogen, methyl, methoxy, ethoxy, methoxyethoxy, and ethoxyethoxy, and R.sup.4 is methoxy, ethoxy, methoxyethoxy and ethoxyethoxy.

10. A pharmaceutical preparation according to claim 9, in a form suitable for administration by injection wherein the compound comprises about 0.5% to 20% by weight of the preparation.

11. A pharmaceutical preparation according to claim 9 for parenteral application which comprises an aqueous solution of a water soluble salt of said active ingredient in an amount of about 0.5 to 10% by weight of the preparation.

12. A pharmaceutical preparation according to claim 9 in a form suitable for oral administration wherein the active ingredient comprises about 2% to about 50% by weight of the preparation.

13. A pharmaceutical preparation according to claim 9 in dosage unit form suitable for oral administration wherein the dosage of active ingredient is in the range to 100 to 400 milligrams.

14. A pharmaceutical preparation according to claim 9 in dosage unit form suitable for intravenous administration wherein the dosage of active ingredient is in the range 5 to 20 milligrams.

15. A pharmaceutical preparation according to claim 9 wherein the active ingredient is selected from the group consisting of

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-5-acetyl-6-methyl)-benzimidazole,

2-[2-(4-methoxy)-pyridylmethylsulfinyl]-4,6-dimethyl)-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-be nzimidazole,

[ 2-(4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzimidaz ole,

2-[2-(4-ethoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzimidaz ole,

2-[2-(3-methyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)- benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-meth yl)-benzimidazole,

2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)b enzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy)-benzi midazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl)-benzimidazo le,

2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-methoxy)-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methoxy)-benzimidaz ole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methyl)-benzimidazo le,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-benzimidazole,

2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-chloro)-benzimidazo le, or a pharmaceutically acceptable non-toxic addition salt thereof in a therapeutically effective amount.

16. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy)-benz imidazole or a pharmaceutically acceptable non-toxic acid addition salt thereof in a therapeutically effective amount.

17. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-met hyl)-benzimidazole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

18. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl)-benzimidaz ole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

19. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-b enzimidazole or a pharmaceutically acceptable non-toxic addition salt thereof in a therapeutically effective amount.

20. A pharmaceutical parparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methoxy)-benzimida zole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

21. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-methyl)-benzimidaz ole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

22. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-benzimidazole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

23. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3-methyl-4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl) -benzimidazole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

24. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(3,5-dimethyl-4-methoxy)-pyridylmethylsulfinyl]-(5-chloro)-benzimidaz ole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

25. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl) -benzimidazole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

26. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(4-methoxy-5-methyl)-pyridylmethylsulfinyl]-(5-methoxy)-benzimidazole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

27. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzimid azole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

28. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazole or a pharmaceutically acceptable non-toxic addition salt thereof in a therapeutically effective amount.

29. A pharmaceutical preparation according to claim 9, wherein the active ingredient is 2-[2-(4-methoxy)-pyridylmethylsulfinyl]-(4,6-dimethyl)-benzimidazole or a pharmaceutically acceptable, non-toxic addition salt thereof in a therapeutically effective amount.

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.