The enantiomer of tenatoprazole and the use thereof in therapy

Abstract

This invention relates to optically active substances of tenatoprazole, (+) and (−)-5-methoxy-2-{(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}-1H-imidazo[4,5-b]pyridine. The compound and pharmaceutical compositions thereof are useful for anti-ulcer agent.

1 . The compound (−)-tenatoprazole, or (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine, or one of its salts. 
     
     
         2 .- 4 . (canceled) 
     
     
         5 . A pharmaceutical composition comprising (−)-tenatoprazole, or (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine, or one of its salts, and one more pharmaceutically acceptable excipients or substances. 
     
     
         6 . The pharmaceutical composition according to  claim 5 , wherein (−)-tenatoprazole, or (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine is in the form of an alkaline or earth-alkaline metal salt. 
     
     
         7 . The pharmaceutical composition according to  claim 5 , wherein (−)-tenatoprazole, or (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine is in the form of a sodium, potassium, lithium, magnesium or calcium salt. 
     
     
         8 . The pharmaceutical composition according to  claim 5 , comprising unitary doses containing from about 10 to about 80 mg of active ingredient. 
     
     
         9 .- 20 . (canceled) 
     
     
         21 . A method for the treatment of a digestive pathology in a subject, which method comprises administering an effective amount of (+)-tenatoprazole, or (+)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine, or one of its salts, to a subject in need thereof to treat the digestive pathology in the subject. 
     
     
         22 . A method for the treatment of Barrett's syndrome, atypical and oesophageal symptoms of gastro-oesophageal reflux, and digestive bleeding refractory to other proton pump inhibitors in a subject, which method comprises administering an effective amount of (+)-tenatoprazole, or (+)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine, or one of its salts, to a subject in need thereof to treat Barrett's syndrome, atypical and oesophageal symptoms of gastro-oesophageal reflux, and digestive bleeding refractory to other proton pump inhibitors in the subject. 
     
     
         23 . A method for the treatment of a digestive pathology, gastro-oesophageal reflux, or digestive bleeding in a patient receiving multiple drug therapy, which method comprises administering an effective amount of (+)-tenatoprazole, or (+)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine, or one of its salts, to a patient receiving multiple drug therapy in need thereof to treat a digestive pathology, gastro-oesophageal reflux, or digestive bleeding in the patient. 
     
     
         24 . The compound (−)-tenatoprazole, or (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine, or one of its salts, wherein the compound has at least 98.8% chiral purity. 
     
     
         25 . The compound of  claim 24 , wherein the compound is (−)-tenatoprazole or one of its salts. 
     
     
         26 . The compound of  claim 24 , wherein the compound is (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine or one of its salts. 
     
     
         27 . The pharmaceutical composition of  claim 5 , wherein the (−)-tenatoprazole, or (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine, or one of its salts, has at least 98.8% chiral purity. 
     
     
         28 . The pharmaceutical composition of  claim 27 , wherein the pharmaceutical composition comprises (−)-tenatoprazole or one of its salts. 
     
     
         29 . The pharmaceutical composition of  claim 27 , wherein the pharmaceutical composition comprises (−)-5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl}imidazo-[4,5-b]pyridine or one of its salts.