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publicationDate 2014-10-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-089950-A2
titleOfInvention COMPOUND 2,3-DIHIDRO-6-NITROIMIDAZO [2,1-B] OXAZOL
abstract Its composition pharmaceutically, its production method and its use as a bactericide. Claim 1: A 2,3-dihydro-6-nitroimidazo [2,1-b] oxazole compound characterized in that it is represented by the general formula (1), the optically active form thereof, or a pharmaceutically acceptable salt thereof, in where R¹ represents a hydrogen atom or C₁₋₆ alkyl group, n represents an integer of value 0 to 6, and R² represents a phenoxy group represented by the general formula (2), wherein X represents a halogen atom or C₁ alkyl group ₋₆ substituted by amino which may have a C₁₋₆ alkyl group as a substituent, m represents an integer from 0 to 3, and R¹¹ represents: E1) hydrogen atom; E2) C₁₋₆ alkyl group unsubstituted or substituted by halogen; E3) C₁₋₆ alkoxy group substituted or unsubstituted by halogen; E4) a group represented by the general formula: - (W) ₒ-NR¹²R¹³ where W represents a group -CO- or an alkylene group C₁₋₆, or represents an integer of value 0 or 1, and R¹² and R¹³ are equal or different and each represents any of: (Ea1) hydrogen atom; (Ea2) C₁₋₆ alkyl group; (Ea3) C₁₋₆ alkanoyl group; (Ea4) C₁₋₆ alkoxycarbonyl group; (Ea5) C₁₋₆ phenylalkyl group (which may be substituted on the phenyl ring by at least one group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, a C₁ alkoxy group ₋₆ unsubstituted or substituted by halogen, and a phenoxy group (which may be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen , and a C₁₋₆ alkoxy group unsubstituted or substituted by halogen as a substituent), and a C₁₋₆ alkoxyimino group may be substituted by the alkyl portion); (Ea6) phenyl group (which can be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and a C₁₋₆ alkoxy group not substituted or substituted by halogen); (Ea7) benzoyl group (which may be substituted on the phenyl ring at least by a group selected from a group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and a C₁₋ alkoxy group ₆ unsubstituted or substituted by halogen); (Ea8) pyridyl group (which can be substituted on the pyridine ring at least by a halogen atom as a substituent); (Ea9) C₁₋₆ phenylalkyl group (which can be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and an alkoxy group C₁₋₆ unsubstituted or substituted by halogen); (Ea10) C₁₋₆ phenoxyalkyl group (which can be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and an alkoxy group C₁₋₆ unsubstituted or substituted by halogen); and (Ea11) benzoyl-C₁₋₆ alkyl group (which may be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and a C₁₋₆ alkoxy group unsubstituted or substituted by halogen), E5) imidazolyl group; E6) triazolyl group; E7) morpholino group; E8) thiomorpholino group; E9) thiomorpholino s-oxide group; E10) piperidyl group represented by the general formula (3), wherein W i are equal to those indicated above, R¹⁴A represents a hydrogen atom, hydroxyl group, C₁₋₆ alkoxy group, or phenyl group (which can be substituted by halogen in the phenyl ring), the dashed line represents a bond that can be a double bond, and when the dashed line represents a double bond, it means that only R¹⁴ is substituted, R¹⁴ and R¹⁴A can be linked together with atoms carbon adjacent thereto to form a C₁₋₄ alkylenedioxy group, and R¹⁴ represents: (Eaa1) hydrogen atom; (Eaa2) C₁₋₆ alkoxycarbonyl group; (Eaa3) phenoxy group (which can be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, an unsubstituted C₁₋₆ alkyl group, an unsubstituted or substituted C₁₋₆ alkoxy group by halogen, a C₁₋₄ alkylenedioxy group, a C₁₋₆ alkoxycarbonyl group, cyano group, C₂₋₆ alkenyl group, a nitro group, phenyl group, amino group which may have, as a substituent, a group selected from the group consisting of a phenyl group, a C₁₋₆ alkyl group, a carbamoyl group and a C₁₋₆ alkanoyl group, a C₁₋₆ alkyl group substituted by C₁₋₆ alkanoyl group, a hydroxyl group, a C₁₋₆ alkyl group substituted by C₁ alkoxycarbonyl ₋₆, a C₁₋₆ phenylalkyl group, a C₁₋₆ alkanoyl group, a C₁₋₆ alkylthio group, a 1,2,4-triazolyl group, an isoxazolyl group, an imidazolyl group, a benzothiazolyl group, a 2H- group benzotriazolyl, a gr upo pyrrolyl, a benzoxazolyl group, a piperazinyl group (which can be substituted in the piperazine ring at least by a group selected from the group consisting of a C₁₋₆ alkoxycarbonyl group and a C₁₋₆ phenylalkyl group (which can be substituted in the phenyl ring at least one group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and a C₁₋₆ alkoxy group unsubstituted or substituted by halogen) as a substituent), a piperidinyl group (which can be substituted in the piperidine ring at least by a group selected from the group consisting of an amino group (which can be substituted in the amino group at least by a group selected from the group consisting of a group C₁₋₆ alkyl and a phenyl group (which can be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, a C alkyl group ₋₆ unsubstituted or substituted by halogen, C₁₋₆ alkoxyl group and an unsubstituted or substituted by halogen) as a substituent) and carbamoyl group)); (Eaa4) hydroxyl group; (Eaa5) carboxyl group; (Eaa6) phenyl group (which can be substituted on the phenyl ring at least by a group selected from the group consisting of a phenoxy group (which can be substituted on the phenyl ring at least by a group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and a C₁₋₆ alkoxy group unsubstituted or substituted by halogen as a substituent), a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen , and a C₁₋₆ alkoxy group unsubstituted or substituted by halogen as substituent); (Eaa7) C₁₋₆ alkoxy group; (Eaa8) C₃₋₈-C₁₋₆ alkoxycycloalkyl group; (Eaa9) phenylcarbamoyl group (which may be substituted on the phenyl ring by at least one group selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group unsubstituted or substituted by halogen, and a C₁₋₆ alkoxy group not substituted or substituted by halogen); (Eaa10) tetrahydropyranyloxy group; (Eaa11) 1,3-dioxolanyl group; (Eaa12) oxo group; (Eaa13) naphthyloxy group (which can be substituted on the naphthalene ring at least by a C₁₋₆ alkyl group as a substituent); (Eaa14) 2,3-dihydrobenzofuryloxy group (which may be substituted on the 2,3-dihydrobenzofuran ring at least by a group selected from the group consisting of a C₁₋₆ alkyl group and an oxo group); (Eaa15) benzothiazolyloxy group (which can be substituted on the benzothiazole ring at least by a C₁₋₆ alkyl group); (Eaa16) 1,2,3,4-tetrahydronaphthyloxy group (which may be substituted on the 1,2,3,4-tetrahydronaphthalene ring at least by an oxo group as a substituent); (Eaa17) 1,3-benzoxathiolanyloxy group (which can be substituted on the 1,3-benzoxathiolane ring at least by an oxo group as a substituent); (Eaa18) isoquinoliloxyl group; (Eaa19) pyridyloxy group; (Eaa20) quinolyloxy group (which can be substituted in the quinoline ring at least by a C₁₋₆ alkyl group as a substituent); (Eaa21) dibenzofuryloxy group; (Eaa22) 2H-chromenyloxy group (which can be substituted on the 2H-chromenyl ring at least by an oxo group as a substituent); (Eaa23) benzisoxazolyloxy group; (Eaa24) quinoxalyloxy group; (Eaa25) 2,3-dihydro-1H-indenyloxy group (which can be substituted in the
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