Gastric acid secretion inhibiting substituted 2-(2-benzimidazolyl)-pyridines, pharmaceutical preparations containing same, and method for inhibiting gastric acid secretion
AssigneeAktiebolaget Hassle
InventorsUlf K. Junggren, Sven E. Sjostrand
Life of this patent
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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.
Claims29
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.
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.
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.
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.
Dependencies are inferred from the claim text.