KR870007912A - Benzo heterocyclic compound and preparation method thereof - Google Patents

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Benzo heterocyclic compound and preparation method thereof

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Claims (77)

Wherein R 'is cyclopropyl which may be substituted by 1 to 3 substituents selected from the group consisting of (lower) alkyl and halogen atoms, and R ² is a 5-9 membered saturated or unsaturated heterocyclic ring which may be substituted , R ³ is composed of 5-6 membered saturated heterocyclic, (low) alkylthio, amino, (low) alkylamino, (low) alkanoyloxy, hydroxy, (low) alkoxy and halogen atoms The preparation of a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein (low) alkyl may be substituted by 1-3 substituents selected from the group, X is a halogen atom. The compound of claim 1, wherein R ′ is unsubstituted cyclopropyl, and R ² is 1-piperidinyl (1-pyrrolidinyl, 1-homopiperazinyl, thiomorpholino, 1,4-diazabicyclo (4,3,0) nona-4-yl, thiomorpholino-4-oxide, thiomorpholino-4,4-dioxide, 1-hexahydropyridazinyl, 2-thiazolidinyl, 1-imi Is a substituted or unsubstituted heterocyclic group selected from the group consisting of dazolidinyl and 3,7-diazabicyclo (4,3,0) nona-3-yl, and R ³ is unsubstituted C ₁ -C ₆ alkyl And X is a fluorine atom or a pharmaceutically acceptable preparation thereof. The compound of claim 1, wherein R ′ is unsubstituted cyclopropyl, R ² is a substituted or unsubstituted unsaturated heterocyclic group in the 5-9 position, and R ³ is an unsubstituted C ₁ -C ₆ alkyl group And X is a fluorine atom, or a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein R ′ is unsubstituted cyclopropyl, N is a fluorine atom, and R ² is a group of the general formula: Wherein R ^A is a hydrogen atom, a C ₁ -C ₆ alkyl group, a phenyl (C ₁ -C ₆ ) alkyl group, wherein the phenyl group is substituted by a C ₁ -C ₆ alkoxy group, nitro group or amino group May be Or a C ₁ -C ₆ alkyl group wherein this group has 1 to 3 substituents selected from the group consisting of a hydroxy group and a C ₁ -C ₆ alkoxy group. And R ³ is an unsubstituted C ₁ -C ₆ alkyl group and a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein R ′ is unsubstituted cyclopropyl, X is a fluorine atom, and R ² is a group of the general formula: Wherein R ^B is a C ₃ -C ₈ cycloalkyl group: phenyl group, wherein the phenyl ring may be substituted by 1-3 of the halogen atoms or may be substituted by halogen atoms. Pyridyl group C₁-C ₆ Alkyl group, which has 1-3 substituents selected from the group consisting of an amino group and a halogen atom, wherein the amino group is C₁-C ₆ alkyl group, C₁-C ₆ alkanoyl group, C₃-C ₈ cycloalkyl And optionally 1 or 2 substituents selected from the group consisting of a group and a C₁-C ₆ alkoxycarbonyl group. C ₂ -C ₆ alkynyl group: C₁-C ₆ alkanoyl group, which may be substituted by halogen atoms 1-7. C₂-C ₆ alkenylbonyl group, substituted by halogen atom or carboxy group 1-3. C₁-C ₆ alkoxycarbonyl group: aminocarbonyl group, which may be substituted by 1 or 2 of C₁-C ₆ alkyl group. Phenylalkoxycarbonyl group, wherein the alkoxy moiety is a C₁-C ₆ alkoxy group. C ₂ -C ₆ aminoalkanoyl group, which may be substituted by a phenylalkoxycarbonyl group wherein the alkoxy moiety is a C₁-C ₆ alkoxy group. Alkoxycarbonylalkyl group, wherein the alkoxy moiety and alkyl moiety are C₁-C ₆ alkoxy and C₁-C ₆ alkyl group, respectively: carboxyalkyl group wherein the alkyl moiety is a C₁-C ₆ alkyl group: anilinocarbonylalkyl group Wherein the alkyl moiety is a C ₁ -C ₆ amino group, wherein this group is a C₁-C ₆ alkyl group, a phenyl (C₁-C ₆ ) alkyl group, a C₁-C ₆ alkoxycarbonyl group or a C₁-C ₆ alkanoyl group It may be substituted by one or two substituents selected from the group consisting of: hydroxy group: C₁-C ₆ alkylsulfonyl group wherein this group may be substituted by halogen atoms of 1-3. Phthalide group: 2 (5H) -furanone group, which may be substituted by a halogen atom. Sulfoalkyl groups, wherein the alkyl moiety is a C ₁ -C ₆ alkyl group: C ₁ -C ₆ alkoxy group: C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkanoyloxy group: 2-oxo-1, 3-dioxolenemethyl group, which may be substituted by phenyl group or C ₁ -C ₆ alkyl group: C ₃ -C ₈ cycloalkyl amino group: and C ₁ -C ₆ alkyl thio group) And R ³ is an unsubstituted C ₁ -C ₆ alkyl group or a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein R ′ is unsubstituted cyclopropyl, X is a fluorine atom, R ² is a 4-substituted or unsubstituted 1-piperazinyl group, which is 2-3-5-and And has 1-3 substituents selected from the group consisting of the groups listed below in the 6-position. C ₃ -C ₈ cycloalkyl group: phenyl (C ₁ -C ₆ ) alkyl group: wherein the phenyl ring may be substituted with a C ₁ -C ₆ alkoxy group, nitro group or amino group. Pyridyl group: C ₁ -C ₆ alkyl group, which has 1-3 of substituents selected from the group consisting of hydroxy group, amino group, C ₁ -C ₆ alkoxy group and halogen atom. Optionally substituted by 1 or 2 substituents selected from the group consisting of _1- C ₆ alkyl group, C ₁ -C ₆ alkanoyl group C ₃ -C ₈ cycloalkyl group and C ₁ -C ₆ alkoxycarbonyl group : C ₁ -C ₆ alkynyl group: C ₂ -C ₆ alkanoyl group, which group may be substituted by 1-7 of halogen atom. C ₂ -C ₆ alkenyl carbonyl group, which is substituted by halogen atom and 1-4 of carboxy group: aminocarbonyl group wherein this group is to be substituted by 1 or 2 of C ₁ -C ₆ alkyl group May also be a phenylalkoxycarbonyl group wherein the alkoxy moiety is a C ₁ -C ₆ alkoxy group: C ₂ -C ₆ amino alkanoyl group wherein this group is a phenylalkoxycarbonyl wherein the alkoxy moiety is a C ₁ -C ₆ alkoxy group It may be substituted by a group: an alkoxycarbonylalkyl group, wherein the alkoxy moiety and the alkyl moiety are each a C ₁ -C ₆ alkoxy group and a C ₁ -C ₆ alkyl group: a carboxyalkyl group: wherein the alkyl moiety is C _1- C ₆ alkyl group. Anilinocarbonylalkyl group, wherein the alkyl moiety is a C ₁ -C ₆ alkyl group: an amino group, where this group is a C ₁ -C ₆ alkyl group, a phenyl (C ₁ -C ₆ ) alkyl group, C ₁ -C It may be substituted by 1 or 2 substituents selected from the group consisting of ₆ alkoxycarbonyl groups, or C ₁ -C ₆ alkanoyl groups: Hydroxy group: C ₁ -C ₆ alkylsulfonyl group, which group may be substituted by 1-3 of halogen atom. 2 (5H) -furanone group wherein this group may be substituted by one or two of the halogen atoms: a sulfoalkyl group, wherein the alkyl moiety is a C ₁ -C ₆ alkyl group: oxo group: C ₁ -C ₆ Alkoxy group: C ₁ -C ₆ alkenyl group: Halogen atom: C ₂ -C ₆ Alkanoyloxy group: 2-oxo-1,3-dioxorenmethyl group, wherein this group is a phenyl group or C ₁ -C ₆ It may be substituted by an alkyl group. C ₁ -C ₆ cycloalkylamino group: C ₁ -C ₆ alkylthio group: thio group: and 2-oxo-1,3-dioxorenmethyl amino group wherein this group is a phenyl group or C ₁ -C ₆ It may be substituted by an alkyl group. (If the number of substituents in the piperazinyling is not greater than 3) and R ³ is an unsubstituted C ₁ -C ₆ alkyl group and the preparation of a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein R ′ is unsubstituted cyclopropyl, X is a fluorine atom, and R ² is a 1-piperazinyl group, which is a group consisting of a C ₁ -C ₆ alkyl group and a phenyl group. Having 1-3 substituents selected at 2-, 3-, 5- and 6-positions where the phenyl ring in the phenyl group is a C ₁ -C ₆ alkyl group which may be substituted by a halogen atom or 1-3 of a halogen atom It may be substituted by, and furthermore, this phenyl ring is C ₁ -C ₆ alkyl, C ₁ -C ₆ alkanoyl, phenyl (C ₁ -C ₆ ) alkyl and 2-oxo-1,3-dioxorenmethyl It may also have a substituent selected from the group consisting of at the 4-position. In this case, the 2-oxo-1,3-dioxolenmethyl group may be substituted by a phenyl group or a C ₁ -C ₆ alkyl group. (If the number of substituents in piperazinyling is not greater than 3), and R ³ is an unsubstituted C₁-C ₆ alkyl group or a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein R ′ is unsubstituted cyclopropyl, X is a fluorine atom, R ² is a pyrrolidinyl group which has 1-3 substituents selected from the group consisting of: C ₁ -C ₆ alkyl group: C ₃ -C ₈ cyclo alkyl group: phenyl (C ₁ -C ₆ ) alkyl group, wherein the phenyl ring may be substituted by a C₁-C ₆ alkoxy group, a nit group or an amino group Phenyl group wherein the phenyl ring may be substituted by a halogen atom or may be substituted by a C₁-C ₆ alkyl group which may be substituted by 1-3 of a halogen atom. Pyridyl group: C₁-C ₆ alkyl group, which has 1-3 of substituents selected from the group consisting of hydroxy group, amino group, C₁-C ₆ alkoxy group and halogen atom. Optionally substituted by 1 or 2 substituents selected from the group consisting of a C ₆ alkyl group, a C₁-C ₆ alkanoyl group, a C ₃ -C ₈ cycloalkyl group and a C₁-C ₆ alkoxycarbonyl group. C₁-C ₆ alkynyl group: C₁-C ₆ alkanoyl group, which may be substituted by 1-7 of halogen atom: C ₂ -C ₆ alkenylcarbonyl group which is a halogen atom or carboxyl group Is a group substituted by 1-3: a C₁-C ₆ alkoxy carbonyl group: an aminocarbonyl group, where this group may be substituted by 1 or 2 of a C₁-C ₆ alkyl group. Phenylalkoxycarbonyl group, wherein the alkoxy moiety is a C₁-C ₆ alkoxy group: C ₂ -C ₆ aminoalkanoyl group, which may be substituted by a phenylalkoxycarbonyl group, which is an alkoxy of the phenylalkoxycarbonyl group The part is a C₁-C ₆ alkoxy group. Alkoxycarbonylalkyl groups, wherein the alkoxy moiety and the alkyl moiety are C₁-C ₆ alkoxy groups and C₁-C ₆ alkyl groups, respectively: a carboxyalkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group. Anilinocarbonylalkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group. Amino group: wherein the group is selected from the group consisting of a C₁-C ₆ alkyl group, a phenyl (C₁-C ₆ ) alkyl group, a C₁-C ₆ alkoxycarbonyl group, or a C 알 -C ₆ alkanoyl group; It may be substituted by a disubstituent. Hydroxy group: C₁-C ₆ alkylsulfonyl group, which may be substituted by 1-3 of halogen atom: phthalide group: 2 (5H) -furanone group, wherein this group is It may be substituted by 1 or 2. Sulfoalkyl groups, wherein the alkyl moiety is a C₁-C ₆ alkyl group: oxo group: C₁-C ₆ alkoxy group: C ₂ -C ₆ alkenyl group: halogen atom: C ₂ -C ₆ alkanoyloxy group: 2- Oxo-1,3-dioxolenemethyl group, which is a phenyl group. It may be substituted by a C₁-C ₆ alkyl group: C₁-C ₆ cycloalkylamino: C₁-C ₆ alkylthio group: thio group: and 2-oxo-1,3-dioxolenmethylamino group, wherein This group may be substituted with a phenyl group or a C₁-C ₆ alkyl group. And R ³ is an unsubstituted C₁-C ₆ alkyl group or a pharmaceutically acceptable salt thereof. The compound of claim 8, wherein R ² is a 1-pyrrolidinyl group, which may have a 1-3 substituent selected from the group consisting of a hydroxy group, a C₁-C ₆ alkyl group, and a C₁-C ₆ alkyl group. The latter C₁-C ₆ alkyl group has substituents 1-3 selected from the group consisting of a hydroxy group and an amino group. Wherein the amino group is optionally substituted by C₁-C ₆ alkyl group 1 or 2. And 1-pyrrolidinyl may have 1-3 substituents selected from amino groups, wherein the amino group may be substituted by C₁-C ₆ alkyl group 1 or 2. Wherein R 'is unsubstituted cyclopropyl, X is a fluorine atom, and R² is a morpholino group, wherein 1-3 is selected from the group consisting of a C₁-C ₆ alkyl group and a phenyl group A method of preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof, which may have a substituent, and R ³ is an unsubstituted C₁-C ₆ alkyl group. Wherein R 'is unsubstituted cyclopropyl, X is a fluorine atom, and R2 is a morpholino, wherein this group has 1-3 substituents selected from the group consisting of: C ₃ -C ₈ cycloalkyl group: phenyl (C₁-C ₆ ) alkyl group wherein the phenyl ring may be substituted with a C₁-C ₆ alkoxy group, nitro group or amino group: phenyl group, wherein the phenyl ring is a halogen atom Is substituted by a C₁-C ₆ alkyl group which may be substituted by or by 3-3 of a halogen atom: a pyridyl group: a C₁-C ₆ alkyl group which is a hydroxy group, an amino group, a C₁- It has 1-3 of the substituents selected from the group consisting of a C ₆ alkoxy group and a halogen atom. The amino group mentioned above is a C₁-C ₆ alkyl group, a C₁-C ₆ alkanoyl group, a C ₃ -C ₈ cycloalkyl group And optionally substituted by 1 or 2 substituents selected from the group consisting of C₁-C ₆ alkoxycarbonyl groups: C ₂ -C ₆ alkynyl groups: C₁-C ₆ alkanoyl groups, wherein this group is 1 To be substituted by -7 It may also be a C ₂ -C ₆ alkenylcarbonyl group, which is a group substituted by one to three of the halogen atoms or carboxy groups: C₁-C ₆ alkoxycarbonyl group: aminocarbonyl group, where this group May be substituted by 1 or 2 of the C₁-C ₆ alkyl group: a phenylalkoxycarbonyl group, wherein the alkoxy moiety is a C₁-C ₆ alkoxy group: a C ₂ -C ₆ aminoalkanoyl group, wherein It may also be substituted by a phenylalkoxycarbonyl group wherein the alkoxy moiety of the phenylalkoxycarbonyl group is a C₁-C ₆ alkoxy group: an alkoxycarbonylalkyl group, wherein the alkoxy moiety and the alkyl moiety are each C₁-C ₆ alkoxy group and C₁ -C ₆ alkyl group: carboxyalkyl group wherein the alkyl part is a C₁-C ₆ alkyl group: anilino-carbonyl-alkyl group, wherein the alkyl part is a C₁-C ₆ alkyl group, amino group, where this group is C₁ -C ₆ alkyl group, phenyl ( C₁-C ₆ ) may be substituted by one or two substituents selected from the group consisting of an alkyl group, a C₁-C ₆ alkoxycarbonyl group or a C₁-C ₆ alkanoyl group: hydroxy group: C₁-C ₆ alkylsulphur Ponyl group, where this group may be substituted by 1-3 of halogen atom: Phthalide group: 2 (5H) -furanone group, where this group may be substituted by 1 or 2 of halogen atom: Sulfoalkyl groups, wherein the alkyl moiety is a C₁-C ₆ alkyl group. Oxo group: C₁-C ₆ alkoxy group: C ₂ -C ₆ alkenyl group: halogen atom: C ₂ -C ₆ alkanoyloxy group: 2-oxo-1,3-dioxorenmethyl group, wherein this group is phenyl It may be substituted by a group or a C₁-C ₆ alkyl group: C ₃ -C ₈ cyclochalkylamino group: C₁-C ₆ alkylthio group: thio group: and 2-oxo-1,3-dioxorenmethyl Amino group, where this group may be substituted by phenyl group or C 또는 -C ₆ alkyl group. And R 3 is an unsubstituted C₁-C ₆ alkyl group and a pharmaceutically acceptable salt thereof. The preparation method of a compound according to claim 4, wherein R ^A is a C₁-C ₆ alkyl group. 13. The method of claim 12, wherein R < 3 > is methyl. 13. The method of claim 12, wherein R < 3 > is ethyl. The process of claim 5 wherein R ^B is a 2-oxo-1,3-dioxorenmethyl group, wherein this group may be substituted by a phenyl or C₁-C ₆ alkyl group. The method for preparing a compound according to claim 5, wherein R ^B is a group other than a 2-oxo-1,3-dioxorenmethyl group which may be substituted by a phenyl or a C₁-C ₆ alkyl group. The preparation of a compound of claim 15 wherein R 3 is methyl. The preparation of a compound according to claim 15, wherein R 3 is ethyl. In paragraph 7, R² is a group of the formula: Wherein R ^L and R ^E are each a C₁-C ₆ alkyl group, and R ^D is a 2-oxo-1,3 which may be substituted by a hydrogen atom, a C₁-C ₆ alkyl group or a phenyl or C₁-C ₆ alkyl group Preparation of the compound which is a dioxoren methyl group. In paragraph 7, R² is a group of the formula: Wherein R ^F is a C₁-C ₆ alkyl group. In claim 7, R² is a group of the following general formula: Wherein R ^G is a C₁-C ₆ alkyl group, and R ⁷ is a C 소 -C ₆ alkyl group or a 2-oxo-1,3-dioxorenmethyl group which may be substituted by a phenyl or C₁-C ₆ alkyl group Recipe. The preparation of a compound according to claim 19, wherein R 3 is methyl. The preparation of a compound according to claim 19, wherein R3 is ethyl. The preparation of a compound according to claim 20, wherein R 3 is methyl. The preparation of a compound according to claim 20, wherein R 3 is ethyl. The method of claim 26, wherein R 3 is methyl. The preparation of a compound according to claim 21, wherein R 3 is ethyl. 10. The compound of claim 9, wherein R² is a 1-pyrrolidinyl group of the formula: Wherein R ^I is a C₁-C ₆ alkyl group which has one amino group which is optionally substituted by 1 or 2 of the C₁-C ₆ alkyl group. Or R ^I is an amino group which may be optionally substituted by 1 or 2 of the C₁-C ₆ alkyl group. And R ^J is a hydrogen atom or a C₁-C ₆ alkyl group. The method of claim 28, wherein R ^I is an amino group which may be substituted by one C 하나 -C ₆ alkyl group. 29. The compound of claim 28, wherein R ^I is C R-C ₆ alkyl having one amino group, wherein the amino group may be optionally substituted by one C₁-C ₆ alkyl group. And R ^J is a hydrogen atom. The method of claim 29, wherein R 3 is methyl. 31. The preparation of a compound of claim 30, wherein R < 3 > is methyl. 11. The compound of claim 10 wherein R² is a group of the formula: Wherein R ^K is a hydrogen atom or a C₁-C ₆ alkyl group. The preparation of a compound according to claim 33, wherein R 3 is methyl. The preparation of a compound according to claim 11, wherein R 3 is methyl. 2. The unsubstituted cyclopropyl of claim 1, X is a fluorine atom, R 2 is a 1-piperidinyl group, wherein the group is substituted with 1-3 substituents selected from the group consisting of Have C₁-C ₆ alkyl group: C ₃ -C ₈ cycloalkyl group: phenyl (C₁-C ₆ ) alkyl group, wherein the phenyl ring may be substituted by a C₁-C ₆ alkoxy group, nitro group or amino group: Phenyl group, wherein phenyl ring may be substituted by C 할로겐 -C ₆ alkyl group which may be substituted by halogen atom or may be substituted by 1-3 of halogen atom. Pyridyl groups: C₁-C ₆ alkyl group, the group also inde Hyde of hydroxy group, amino group, C₁-C ₆ alkoxy group and Amano group mentioned above there have 1-3 substituents selected from the group which consists of halogen atoms, C₁ Optionally substituted by 1 or 2 substituents selected from the group consisting of a -C ₆ alkyl group, a C₁-C ₆ alkanoyl group, a C ₃ -C ₈ cyclo alkyl group and a C₁-C ₆ alkoxycarbonyl group: C ₂ -C ₆ alkynyl group: C₁-C ₆ alkanoyl group, which may be substituted by 1-7 of halogen atom: C ₂ -C ₆ alkenyl carbonyl group, which is a halogen atom Substituted by 1-3 of the carboxy group: aminocarbonyl group, which may be substituted by 1 or 2 of the C₁-C ₆ alkyl group: phenylalkoxy carbonyl group, wherein the alkoxy moiety is C₁-C _61, or the alkyl group 2 There C ₂ -C ₆ alkanoyl-amino group, wherein the group is optionally substituted by phenyl alkoxycarbonyl group: may be optionally substituted: phenyl-alkoxy-carbonyl group, wherein the alkoxy part is C₁-C ₆ alkoxy group, a Wherein the alkoxy moiety of the phenylalkoxy carbonyl group is a CC-C ₆ alkoxy group: an alkoxycarbonyl alkyl group, wherein the alkoxy moiety and the alkyl moiety are each C₁-C ₆ alkoxy and a C₁-C ₆ alkyl group: a carboxyalkyl group, Wherein the alkyl moiety is a C₁-C ₆ alkyl group: an anilinocarbonylalkyl group, wherein the alkyl moiety is also a C₁-C ₆ alkyl group: an amino group, where this group is a C₁-C ₆ alkyl group, phenyl (C₁-C ₆ ) may be substituted by 1 or 2 of the alkyl group C₁-C ₆ alkoxycarbonyl group, or C₁-C ₆ alkanoyl group: hydroxy group: C₁-C ₆ alkylsulfonyl group, wherein this group is halogen Chi by 1-3 of atoms May be: 2 (5H) - Pew ranon group, where this group may be substituted by one or two of a halogen atom: a sulfo-alkyl group, wherein the alkyl part is C₁-C ₆ alkyl group: oxo groups: C₁ -C ₆ alkoxy group: C₁-C ₆ alkenyl group: halogen atom: C ₂ -C ₆ alkanoyloxy group: 2-oxo-1,3-dioxorenmethyl group, wherein this group is a phenyl group or C₁-C _It may also be substituted by a ₆ alkyl group: C ₃ -C ₈ cycloalkylamino: C₁-C ₆ alkylthio group: thio group: Grego 2-oxo-1,3-dioxorenmethylamino group, wherein The group may be substituted by a phenyl group or a C₁-C ₆ alkyl group. And R ³ is an unsubstituted C₁-C ₆ alkyl group and a pharmaceutically acceptable salt thereof. The preparation of a compound according to claim 36, wherein R3 is methyl. 37. The preparation of a compound according to claim 36, wherein R < 2 > is a 1-piperidinyl group, which group may have 1-3 substituents selected from the group consisting of oxo group, halogen atom and C₁-C ₆ alkyl group. The process of claim 38, wherein R 2 is 1-piperadinyl, wherein this group is substituted by one halogen atom. 40. The method of claim 39, wherein R is methyl. 40. The method of claim 39, wherein R < 3 > is ethyl. The preparation of a compound according to claim 38, wherein R2 is a 1-piperadinyl group which has a substituent selected from a hydroxy group and an oxo group. The preparation of a compound of claim 2 wherein R 2 is a group of the formula: The method of claim 2, wherein R 2 is 1-homopiperazinyl or thiopoly, which group may be substituted by a C₁-C ₆ alkyl group. 45. The method of claim 44, wherein R is methyl. 4. The process according to claim 3, wherein R2 is unsubstituted 1,2,5,6-tetrahydropyridyl, unsubstituted imidazolyl, unsubstituted pyridyl. 47. The preparation of a compound of claim 46, wherein R < 3 > is methyl. The compound of claim 1, wherein R 'is cyclopropyl, wherein the compound is composed of a C₁-C ₆ alkyl group and a halogen atom, and thus has substituents 1-3 selected from the group. And X is a fluorine atom, and a pharmaceutically acceptable salt thereof. X is a fluorine atom, and R2 is a heterocyclic group selected from the group consisting of the following compounds. 1-piperazinyl, 1-piperidinyl, 1-pyrrolidinyl, 1-homopiperazinyl, morpholino, thiomorpholino, 1,2,5,6-tetrahydropyrio-1-yl , 1-imidazolyl, 1,4-diazabicyclo (4,3,0) nona-4-yl, thiomorpholin-4-oxide, thiomorpholino-4,4-dioxide, 1-pyra Zolidinyl, 1-hexahydropyridazinyl, pyridyl, 2-thiazolidinyl, 2-thio-1-imadazolidinyl, 2-oxo-1-imidazolidinyl or 3,7-diazabicyclo (4,3,0) nona-3 days wherein the heterocyclic group described above is optionally substituted by 1-3 substituents selected from the group consisting of the groups listed below. C₁-C ₆ alkyl group: C ₃ -C ₈ -cycloalkyl group: phenyl (C₁-C ₆ ) alkyl group wherein the phenyl ring may be substituted by a C₁-C ₆ alkoxy group, nitro group or amino group: pyenil group wherein the phenyl ring may be substituted by a halogen atom may be substituted by C₁-C ₆ alkyl group which may be substituted with 1 to 3 of halogen atoms inde C₁-C ₆ alkyl group, a hydroxyl group A group having 1-3 of substituents selected from oxy group, amino group, C₁-C ₆ alkoxy group and halogen atom group, wherein amino group is C₁-C ₆ alkyl group, C₁-C ₆ alkanoyl group Optionally substituted by 1 or 2 substituents selected from the group consisting of a C ₃ -C ₈ cycloalkyl group and a C₁-C ₆ alkoxycarbonyl group: C ₂ -C ₆ alkynyl group: C₁-C ₆ alkanoyl Group, where this group is the halo It may be substituted by 1-7 of the gen atom. C ₂ -C ₆ alkenylcarbonyl group, which is a group substituted by halogen atom or 1-3 of carboxy group: C₁-C ₆ alkoxycarbonyl group: aminocarbonyl group, wherein this group is C₁- May be substituted by 1 or 2 of the C ₆ alkyl group: a phenylalkoxycarbonyl group, wherein the alkoxy moiety is a C₁-C ₆ alkoxy group: a C ₂ -C ₆ amino alkanoyl group, wherein this group is a phenylalkoxycarbo It may also be substituted by a silyl group wherein the alkoxy moiety of the phenylalkoxy carbonyl group is a C₁-C ₆ alkoxy group: an alkoxycarbonyl alkyl group, wherein the alkoxy moiety and the alkyl moiety are each C₁-C ₆ alkoxy group and C₁-C ₆ alkyl group is a carboxyalkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group: an anilinocarbonyl alkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group: an amino group, where this group is C₁-C ₆ alkyl group, Carbonyl (C₁-C ₆₎ alkyl group, C₁-C ₆ alkoxycarbonyl group or a C₁-C ₆ optionally substituted by one or two of the alkanoyl group: hydroxyl group: C₁-C ₆ alkylsulfonyl group, At this time, this group may be substituted by 1-3 of halogen atom. Phthalite group: 2 (5H) -furanone group, which may be substituted by one or two of halogen atoms: sulfoalkyl group, wherein the alkyl moiety is also a C₁-C ₆ alkyl group: oxo group: C₁ -C ₆ alkoxy group: C ₂ -C ₆ alkenyl group: halogen atom: C ₂ -C ₆ alkanoyloxy group: 2-oxo-1,3-dioxorenmethyl group, wherein this group is a phenyl group or C₁- It may be substituted by a C ₆ alkyl group: C ₃ -C ₈ cycloalkylamino group: C₁-C ₆ alkylthio group: thio group: and 2-oxo-1,3-dioxorenmethyl amino group, wherein This group may be substituted by a phenyl group or a C₁-C ₆ alkyl group. And R 3 is an unsubstituted C₁-C ₆ alkyl group and a pharmaceutically acceptable salt thereof. The method of claim 49, wherein R 2 is 1-piperazinyl. 51. The R² of claim 50 is a group of the formula: Wherein R ^L and R ^N are each a hydrogen atom or a C₁-C ₆ alkyl group and R ^M is a hydrogen atom or a C₁-C ₆ alkyl group. The method of claim 51, wherein R 3 is methyl. The group of claim 49 wherein R² is a group of the formula: Wherein R ^O is a hydrogen atom or a C₁-C ₆ alkyl group. 54. The method of claim 53, wherein R is methyl. 49th inde R² is 1-pyrrolidinyl group in the term, where the group is C₁-C ₆ C₁-C with an amino group which may be substituted by 1 or 2 of alkyl groups ₆ alkyl group and C₁-C ₆ Preparation of the compound which may have in 3-4- position by the amino group which may be substituted by 1 or 2 of an alkyl group. The method of claim 55, wherein R 3 is methyl. 13. The compound of claim 12, wherein R² is a 1-piperidinyl group, wherein the group is selected from the group consisting of a halogen atom, an oxo group, a hydroxy group and a C₁-C ₆ alkyl group. quite. The method of claim 57, wherein R 3 is methyl. The compound of claim 1, wherein R 'is unsubstituted cyclopropyl, X is a fluorine atom, and R² is a 1-piperazinyl group, wherein the group is 1- selected from the group consisting of a C₁-C ₆ alkyl group and a phenyl group. A group having three substituents in the 2-, 3-, 5-, and 6-positions wherein the phenyl ring in the phenyl group may be substituted for a halogen atom or substituted with 1-3 of a halogen atom; It may also be substituted by a C 그룹 -C ₆ alkyl group. Furthermore, this 1-piperazinyl group has a substituent selected at 4-position from the group consisting of the following groups. C ₃ -C ₈ cyclo alkyl group: phenyl (C₁-C ₆ ) alkyl group, wherein the phenyl ring may be substituted by a C₁-C ₆ alkoxy group, nitro group, inaamino group: phenyl group, where phenyl ring May be substituted by a halogen atom, or may be substituted by a C₁-C ₆ alkyl group which may be substituted by 1-3 of a halogen atom: a pyridyl group: a C₁-C ₆ alkyl group which is amino A group having 1-3 of substituents selected from the group consisting of a group and a halogen atom, wherein the amino group is a C₁-C ₆ alkyl group, a C₁-C ₆ alkanoyl group, a C ₃ -C ₈ cycloalkyl group, Optionally substituted by 1 or 2 substituents selected from the group consisting of C₁-C ₆ alkoxycarbonyl groups: C ₂ -C ₆ alkynyl groups: C₁-C ₆ alkanoyl groups, wherein this group is a halogen atom By 1-3 It may be substituted: a C ₂ -C ₆ alkenylcarbonyl group, which is a group substituted by 1-3 of a halogen atom or a carboxy group: C₁-C ₆ alkoxy carbonyl group: aminocarbonyl group, wherein This group may be substituted by 1 or 2 of the C₁-C ₆ alkyl group: a furanalkoxycarbonyl group, wherein the alkoxy moiety is a C₁-C ₆ alkoxy group C₁-C ₆ aminoalkanoyl group, wherein this group is phenyl It may also be substituted by an alkoxy-carbonyl group wherein the alkoxy moiety of the phenylalkoxy carbonyl group is a C₁-C ₆ alkoxy group: an alkoxycarbonyl alkyl group, wherein the alkoxy moiety and the alkyl moiety are each C₁-C ₆ alkoxy group C ₁ -C ₆ alkyl group: a carboxyalkyl group, wherein the alkyl moiety is a C ₁ -C ₆ alkyl group: an amino group, where this group is a C₁-C ₆ alkyl group phenyl (C₁-C ₆ ) alkyl group, C₁ -C ₆ alkoxycarbonyl group or C₁-C ₆ egg May be substituted by 1 or 2 of the canoyl group: hydroxy group: C₁-C ₆ alkylsulfonyl group, where this group may be substituted by 1-3 of halogen atoms: 2 (5H) -fu A lanone group, which may be substituted by one or two of the halogen atoms: a sulfoalkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group: oxo group: C₁-C ₆ alkoxy group: C₂-C ₅ Alkenyl group: halogen atom: C ₂ -C ₆ alkanoyloxy group: 2-oxo-1,3-dioxorenmethyl group, which may be substituted by a phenyl group or a C₁-C ₆ alkyl group: C₁-C ₆ alkylthio group: and 2-oxo-1,3-dioxolenmethyl amino group, which may be substituted by phenyl group or C₁-C ₆ alkyl group: and R³ is unsubstituted. Preparation of a compound which is a C-C ₆ alkyl group and a pharmaceutically acceptable salt thereof. The method of claim 29, wherein R 3 is ethyl. 31. The method of claim 30, wherein R < 3 > is ethyl. The compound of claim 1 wherein R ₃ is C₁-C ₆ alkyl, wherein the compound is a 5- or 6-saturated heterocyclic group, a C₁-C ₆ alkylthio group, an amino group, a C₁-C ₆ alkylamino group , by C₁-C ₆ Al Keno one oxy group, hydroxyl group, C₁-C ₆ 1-3 substituents selected from an alkoxy group, and the group that consists of its yeomdeung to accept the or halogen source, or a pharmaceutically Preparation of a compound which may be substituted. 63. The heterocyclic group of claim 62, wherein the heterocyclic group is 1-pyrrolidinyl, 1-piperazinyl, 1-piperidinyl, morpholino, thiomorpholino, thiomorpholino-4-oxide, thiomorphoyl Preparation of a compound consisting of a composition selected from the group consisting of no-4,4-dioxide, 1-hexahydropyridazinyl, 2-thiazolidinyl and 1-imidazolidinyl. 64. The heterocyclic group is optionally substituted by 1-3 substituents selected from the group consisting of the following groups: C₁-C ₆ alkyl group, C ₃ -C ₈ cycloalkyl group, phenyl (C₁-C ₆ ) alkyl group, wherein the phenyl ring may be substituted with a C₁-C ₆ alkoxy group, nitro group or amino group: phenyl Group, wherein the phenyl ring may be substituted by a halogen atom, or may be substituted by a C₁-C ₆ alkyl group which may be substituted by 1-3 of a halogen atom: pyridyl group: C₁-C ₆ alkyl Which is a group containing 1-3 of substituents selected from the group consisting of a hydroxy group, an amino group, a C₁-C ₆ alkoxy group, and a halogen atom, wherein the amino group described above is C₁-C ₆ Optionally substituted by one or two substituents selected from the group consisting of an alkyl group, a C₁-C ₆ alkanoyl group, a C ₃ -C ₈ cycloalkyl group and a C₁-C ₆ alkoxycarbonyl group: C ₂ -C ₆ alkynyl group: C₁-C ₆ Alkanoyl groups, which may be substituted by 1-7 of a halogen atom: a CC-C ₆ alkenyl carbonyl group which is substituted by 1-3 of a halogen atom or a carboxy group: Aminocarbonyl groups, which may be substituted by 1 or 2 of the C₁-C ₆ alkyl group: a phenylalkoxycarbonyl group, wherein the alkoxy moiety is a C₁-C ₆ alkoxy group: C ₂ -C ₆ amino An alkanoyl group, which may be substituted by a phenylalkoxycarbonyl group, wherein the alkoxy moiety in the phenylalkoxycarbonyl group is a C₁-C ₆ alkoxy group: an alkoxycarbonylalkyl group, where the alkoxy moiety and the alkyl moiety are respectively A C₁-C ₆ alkoxy group and a C₁-C ₆ alkyl group: a carboxyalkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group: an anilinocarbonylalkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group: army Group wherein the group may be substituted by C₁-C ₆ alkyl group, a phenyl (C₁-C ₆₎ alkyl group, C₁-C ₆ alkoxycarbonyl group or C₁-C ₆ 1 or 2 alkanoylamino groups: hydroxy Roxy group: C₁-C ₆ alkylsulfonyl group, where this group may be substituted by 1-3 of halogen atom: Phthalide group: 2 (5H) -furanone group, where this group is 1 of halogen atom Or substituted by 2: a sulfoalkyl group, wherein the alkyl moiety is a C₁-C ₆ alkyl group: oxo group: C₁-C ₆ alkoxy group: C ₂ -C ₆ alkenyl group: halogen atom: C _2- C ₆ alkanoyloxy group: 2-oxo-1,3-dioxorenmethyl group, which may be substituted by phenyl group or C₁-C ₆ alkyl group: C ₃ -C ₈ cycloalkylamino group: C₁-C ₆ alkylthio group: thio group: 2-oxo-1, 3-dioxane Soren methyl-amino group, wherein the group Carbonyl group or is C₁-C ₆ optionally substituted by alkyl group: and X is a fluorine atom in the formula compound. 7- (4- (5-methyl-2-oxo-1,3-dioxoren-4-yl) methyl-1-piperazinyl) -1-cyclopropyl-6-fluoro-8-methyl-1, Preparation of 4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 7- (3-methyl-1-piperazinyl) -1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 7- (3-amino-1-pyrrolidinyl) -1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 1-cyclopropyl-7- (3-aminomethyl-1-pyrrolidinyl) -6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 1-cyclopropyl-7- (3-methylamino-1-pyrrolidinyl) -6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 1-cyclopropyl-7- (3-ethylaminomethyl-1-pyrrolidinyl) -6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 1-cyclopropyl-7- (3-amino-4-methyl-1-pyrrolidinyl) -6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid . Preparation of 1-cyclopropyl-7- (4-fluoro-1-piperidinyl) -6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 1-cyclopropyl-7-morpholino-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Preparation of 1-cyclopropyl-7- (3-methylmorpholino) -6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. The method of claim 1, (a) subjecting the compound of formula 1 to a cyclization reaction to form a compound of formula 2; Wherein R 1, R ² , R ³ , and X are as defined in claim 1, X 2 is a halogen atom, and R ⁵ is low alkyl. Where R 1, R ² , R ³ and X are as defined in claim 1 and R ⁵ is as defined above, optionally followed by hydrolysis of the above compounds. (b) reacting a compound of the first general formula with a compound R 2 H as defined in claim 1 to form a compound of the second general formula. Where R ', R³ and X are as defined in claim 1, X is a halogen atom, R ¹³ is a hydrogen atom or a group of the formula: Where R ¹⁴ and R ¹⁵ are each alkyl Wherein R¹, R², R³ and X are as defined in claim 1 and R ¹³ is as defined above, where R ¹³ is a compound of the formula: It is optionally followed by the conversion of the phosphorus compound to a compound of R ¹³ hydrogen. (c) reacting a compound of the first formula with a compound of the second formula to form a compound of the third formula. Where R¹, R³ and X are as defined in claim 1, one of Z or W is -CH ² -and the other is And n is an integer of 1-3. R ¹⁶ X ¹⁵ Wherein R ¹⁶ is (low) alkyl: cycloalkyl: phenyl (low) alkyl, wherein the phenyl ring is (low) alkoxy, nitro or amino and the compound is a halogen atom (low) alkyl, or halogen atom 1-3 It may also be substituted by (low) alkyl substituted by: pyridyl: (low) alkyl which has 1-3 substituents selected from the group consisting of hydroxy, amino, (low) alkoxy and halogen atoms The amino mentioned above is optionally substituted by (low) alkyl, (low) alkanoyl, cyclo alkyl or (low) alkoxycarbonyl: (low) alkanoyl, wherein this compound is to be substituted by halogen atoms 1-3 It may be: (low) alkenylcarbonyl, which is a compound having 1-3 substituents selected from the group consisting of halogen atoms and carboxy: (low) alkoxy carbonyl: aminocarbonyl, wherein The mixture may be substituted by (low) alkyl: amino (low) alkanoyl, wherein the compound may be substituted by phenyl (low) alkoxycarbonyl: (low) alkoxycarbonyl (low) alkyl: carboxy (Low) Alkyl: Anilinocarbonyl (Low) Alkyl: (Low) Alkylsulfonyl, where the compound may be substituted by halogen atoms 1-3: Sulfo (Low) Alkyl: (Low) Alkenyl or ( Alkynyl and X ⁵ are halogen atoms. Where R¹, R³ and X are as defined in claim 1, n is as defined above, and either Z 'or W' is -CH _2- , and the other is to be. (d) reacting a compound of the first formula with a compound of the second formula to form a compound of the third formula. Where R 1, R 3 and X are as defined in claim 1 and W, Z and n are as defined above. Where R ¹⁷ and R ¹⁸ are each hydrogen or low alkyl. Where R¹, R³ and X are as defined in claim 1, n is as defined above, one of Z "or W" is -CH ₂ -and the other is to be. (e) reacting with a compound of the first formula and a compound of the second formula to form a compound of the third formula. Where R¹, R³ and X are as defined in claim 1 and W, Z and X are as defined above. Wherein R ²³ is phenyl, low alkyl or hydrogen atom and X ⁸ is a halogen atom. Where R¹, R³ and X are as defined in claim 1, n is as defined above, one of Z "or W" is -CH ₂ -and the other is to be. (R ₂₃ is as defined above.) (f) cyclizing the first compound of formula to form a second compound of formula. Where R 'and X are as defined in claim 1, R ²¹ is of the same type as or is a halogen atom, and R ³¹ is (Where R ¹⁹ and R ²⁰ are as defined above) or R ³ (where R ³ is as defined in claim 1), and R ²⁶ and R ²⁷ are each lower alkyl. Where R 'and X are as defined in claim 1 and R ²¹ and R ³¹ are as defined above. (g) Making a compound of the second general formula with a compound of the first general formula. Wherein R 'and X are as defined in claim 1, R ²¹ and R ³¹ are as defined above and R ²⁴ is low alkyl. Wherein R ′ and X are as defined in claim 1, and R ²¹ , R ²³ and R ²⁴ are as defined above, and wherein the hydrolysis thereof is optionally followed. An effective amount of the compound of the formula is included as an essential active ingredient. Wherein R ¹ is cyclopropyl, wherein the compound may be substituted by 1-3 of a substituent selected from the group consisting of (low) alkyl and halogen atoms. R ² is a 5-9 saturated or unsaturated heterocyclic ring which may be substituted, R ³ is (low) alkyl wherein the compound is a 5 or 6 saturated heterocyclic ring, (low) alkylthio And may be substituted by 1-3 of a substituent selected from the group consisting of amino, (low) alkylamino, (low) alkanoyloxy, hydroxy, (low) alkoxy and halogen atoms. X is an antimicrobial composition consisting of a compound which is a halogen atom and a mixture with a pharmaceutically acceptable diluent or carrier or a pharmaceutically acceptable salt thereof. A method of using sulfur compounds of the compound of claim 1. ※ Note: The disclosure is based on the initial application.