.

Pharmaceutical Business Intelligence

  • Anticipate P&T budget requirements
  • Evaluate market entry opportunities
  • Find generic sources and suppliers
  • Predict branded drug patent expiration

► Plans and Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

DrugPatentWatch Database Preview

Details for Patent: 4,337,257

« Back to Dashboard

Details for Patent: 4,337,257

Title: Gastric acid secretion inhibiting substituted 2-(2-benzimidazolyl)-pyridines, their preparation, 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)
Filing Date:May 19, 1980
Application Number:06/150,965
Claims:1. A compound of formula III ##STR13## 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, alkyl having from 1-7 carbon atoms, halogen, carbomethoxy, carboethoxy, alkoxy having up to 5 carbon atoms, and alkanoyl having up to 4 carbon atoms 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 hydrogen or methyl 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.

2. A compound selected from the group consisting of

2-[2-(3,4-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(4,6-dimethyl)-benzimidazole,

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

2-[2-(4,5-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(4,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,4-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(3,4,5-trimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimida zole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,4,5-trimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-ben zimidazole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy)-benzimidazole.

3. A pharmaceutical preparation for inhibiting gastric acid secretion which contains as an active agent a compound of the formula III ##STR14## 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, alkyl having from 1-7 carbon atoms, halogen, carbomethoxy, carboethoxy, alkoxy having up to 5 carbon atoms, and alkanoyl having up to 4 carbon atoms 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 hydrogen or methyl, 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, said compound being associated with a pharmaceutically acceptable carrier.

4. A pharmaceutical preparation according to claim 3, in a form suitable for administration by injection wherein the compound comprises about 0.5% to about 20% by weight of the preparation.

5. A pharmaceutical preparation according to claim 3, 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.

6. A pharmaceutical preparation according to claim 3, in a form suitable for oral administration wherein the active ingredient comprises about 2% to about 50% by weight of the preparation.

7. A pharmaceutical preparation according to claim 3, in dosage unit form suitable for oral administration wherein the dosage of active ingredient is in the range to 100 to 400 milligrams.

8. A pharmaceutical preparation according to claim 3, in dosage unit form suitable for intravenous administration wherein the dosage of active ingredient is in the range 5 to 20 milligrams.

9. A pharmaceutical preparation according to claim 3, wherein the active ingredient is selected from the group consisting of

2-[2-(3,4-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(4,6-dimethyl)-benzimidazole,

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

2-[2-(4,5-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(4,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,4-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(3,4,5-trimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimida zole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,4,5-trimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-ben zimidazole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy)-benzimidazole.

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

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

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

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

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

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

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

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

18. A pharmaceutical preparation according to claim 3, wherein the active ingredient is 2-[2-(3,4,5-trimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimid azole or a pharmaceutically acceptable, non-toxic acid addition salt thereof in a therapeutically effective amount.

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

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

21. 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 ##STR15## 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, alkyl having from 1-7 carbon atoms, halogen, carbomethoxy, carboethoxy, alkoxy having up to 5 carbon atoms, and alkanoyl having up to 4 carbon atoms 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 hydrogen or methyl 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.

22. A method according to claim 21, wherein a compound of formula III selected from the group consisting of

2-[2-(3,4-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(4,6-dimethyl)-benzimidazole,

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

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

2-[2-(4,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,4-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimidazol e,

2-[2-(3,4,5-trimethyl)-pyridylmethylsulfinyl]-(5-acetyl-6-methyl)-benzimida zole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-benzim idazole,

2-[2-(3,4,5-trimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy-6-methyl)-ben zimidazole,

2-[2-(3,5-dimethyl)-pyridylmethylsulfinyl]-(5-carbomethoxy)-benzimidazole.

23. An intermediate of the formula ##STR16## wherein R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, alkyl having from 1-7 carbon atoms, halogen, carbomethoxy, carboethoxy, alkoxy having up to 5 carbon atoms, and alkanoyl having up to 4 carbon atoms, R.sup.6 is selected from the group consisting of hydrogen, methyl and ethyl, and R.sup.3 and R.sup.5 are the same or different and are selected from the group consisting of hydrogen, methyl, methoxy, ethoxy, methoxyethoxy, and ethoxyethoxy, and R.sup.4 is hydrogen or methyl, 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.
« Back to Dashboard

For more information try a trial or see the database preview and plans and pricing

How are People Using DrugPatentWatch?

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 verifification 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.

`abc