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US 7,410,981 B2Granted
Prodrugs of imidazole derivatives, for use as proton pump inhibitors in the treatment of e.g. peptic ulcers
AssigneeTakeda Pharmaceutical Company Limited
InventorsKeiji Kamiyama, Hiroshi Banno, Fumihiko Sato
Life of this patent
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Abstract
An imidazole compound represented by the formula (I), a salt thereof and a compound of the formula (V), which is one of the intermediates thereof. wherein each symbol is as defined in the present specification. The compound of the present invention shows a superior anti-ulcer activity, a gastric acid secretion inhibitory action, a mucosa-protecting action, an anti-Helicobacter pylori action and the like. Since it shows low toxicity, the compound is useful as a pharmaceutical product.
Claims13
An imidazole compound represented by the formula (I):
- wherein
- ring A is a pyridine ring optionally having substituents selected from
- (1) C1-6 alkyl group, and
- (2) C1-6 alkoxy group optionally substituted by substituent(s) selected from halogen atom(s) and C1-6 alkoxy group,
- ring B is a benzene ring optionally having substituents selected from
- C1-6 alkoxy group optionally substituted by halogen atom(s),
- X1 and X2 are each an oxygen atom or a sulfur atom,
- W is a C1-6 alkylene group optionally having substituents selected from C1-6 alkyl-carbonyloxy and ethoxycarbonyloxy or a divalent group represented by the formula:
- —W1-Z-W2—
- wherein W1 and W2 are each a C1-6 alkylene group or a bond, Z is C6-14 arene, an oxygen atom, SOn wherein n is 0, 1 or 2, or >N-E wherein E is a hydrogen atom, a lower alkanoyl group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group, a thiocarbamoyl group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a sulfamoyl group, a mono-lower alkylsulfamoyl group, a di-lower alkylsulfamoyl group, an arylsulfamoyl group, an arylsulfinyl group, an arylsulfonyl group, an arylcarbonyl group or a carbamoyl group, and when Z is an oxygen atom, SOn or >N-E, W1 and W2 are each C1-6 alkylene group,
- R is a group selected from
- (1) C1-6 alkyl group optionally substituted by C1-6 alkyl-carbonyloxy,
- (2) C3-10 cycloalkyl group, and
- (3) C6-14 aryl group optionally substituted by a group represented by —CO—NR2R3 (wherein R2 and R3 are each C1-6 alkyl group),
- D1 is an oxygen atom, a sulfur atom or >NR1,
- D2 is a bond, an oxygen atom, a sulfur atom or >NR1 wherein each R1 is independently C1-6 alkyl group, and
- Y is a group selected from
- (1) C1-6 alkyl group optionally having substituent(s) selected from C1-6 alkoxy group, ethoxycarbonyloxy group, C6-14 aryl group and a group represented by —NR2R3 (wherein R2 and R3 are each C1-6 alkyl group),
- (2) C3-10 cycloalkyl group,
- (3) C6-14 aryl group optionally having substituent(s) selected from (i) halogen atom and (ii) C1-6 alkoxy group optionally having halogen atom(s), and
- (4) tetrahydropyran,
- or a salt thereof.
19 more elements
Dependencies are inferred from the claim text.