KR880005141A - 3-propenyl cefem derivative - Google Patents

Abstract

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Description

3-propenyl cefem derivative

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Claims (22)

3-propenyl cefem derivative represented by the following general formula or a pharmaceutically acceptable salt thereof. Wherein R ₁ is a fluorine-substituted lower alkyl group or a cyano-substituted lower alkyl group, and A is a cyclic or acyclic amino group. The compound according to claim 1, wherein A is an cyclic ammonium group represented by the following structural formula {Wherein R ₂ , R ₃ and R ₄ are the same or different from each other, lower alkyl, hydroxyl substituted lower alkyl, carbamoyl substituted lower alkyl, cyano substituted lower alkyl, amino, (lower alkyl) carbonylamino substituted lower Alkyl, aminosulfonylcarbonyl substituted lower alkyl, (lower alkyl) sulfonylaminocarbonyl substituted lower alkyl, (lower alkyl) aminocarbonyl substituted lower alkyl, hydroxyl and carbamoyl substituted lower alkyl, hydroxyl- and hydroxyl Hydroxy (lower alkyl) aminocarbonyl substituted lower alkyl, (lower alkyloxy) aminocarbonyl substituted lower alkyl, hydroxy aminocarbonyl substituted lower alkyl, carbonyl (lower alkyl) aminocarbonyl substituted lower alkyl, hydroxy (lower Alkyl) aminocarbonyl substituted lower alkyl, (lower alkyl) amino substituted lower alkyl, carboxylate (lower alkyl) di (lower alkyl) amino substituted lower alkyl, (lower alkyl) Mino substituted lower alkyl, (lower alkyl) amino and hydroxyl substituted lower alkyl, ureido, hydroxyl, carboxyl substituted lower alkyl, hydroxyl and carbamoyl substituted lower alkyl, lower alkyloxy substituted lower alkyl, di (lower alkyl ) Amino carbonyl substituted lower alkyl, dicarbamoyl substituted lower alkyl, bis [hydroxyl (lower alkyl)] aminocarbonyl substituted lower alkyl, dihydroxy substituted lower alkyl, trihydroxy chihon lower alkyl, bis [hydroxy ( Lower alkyl) amino substituted lower alkyl, amino substituted lower alkyl, oxosubstituted lower alkyl, di lower alkyl substituted lower alkyl, 5-membered heterocycle substituted lower alkyl (where heterocycle is pyrazolyl, imidazolyl, oxadizolyl or tetra Each group selected from the group consisting of zolyl), or A is a cyclic ammonio group represented by the following structural formula Wherein R ₅ is lower alkyl, carbamoyl substituted lower alkyl, amino substituted lower alkyl, hydroxyl substituted lower alkyl, carboxyl substituted lower alkyl, cyano substituted lower alkyl, dihydroxy substituted lower alkyl and ureido substituted Lower alkyl group, hydroxyl, formyl, sulfonic, carbonyl substituted lower alkyl, carbamoyl, sulfamoyl, carboxyl, or hydroxyl group in the ring. Mino substituted lower alkyl, imino substituted lower alkyl, bis [hydroxy (lower alkyl)] aminocarbamoyl, hydroxy (lower alkyl) aminocarbamoyl, amino, morpholino carbonyl, carboxy (lower alkyloxy) 3-propenyl cefem derivative optionally having at least one substituent selected from the group consisting of substituted lower alkyl, carboxy (lower alkylthio) substituted lower alkyl and lower alkyl group; Pharmaceutically acceptable salts thereof. The 3-propenyl cefem derivative according to claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein R ₁ is a fluoromethyl group. The 3-propenyl cefem derivative according to claim 1 or 2, wherein R ₁ is a cyanomethyl group or a pharmaceutically acceptable salt thereof. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3- (carbamoylmethylethylmethylammonio) -1-propen-1-yl] -3-cefe-4-carboxylate. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3- (1- (2-hydroxyethyl) -4-carbamoyl-1-piperidino) -1-propen-1-yl] -3-cepem-4-carboxylate Phosphorus compounds. The method of claim 3, wherein 7 β -[-2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3 -[(E) -3-[(1S-carbamoylethyl) dimethylammonio] -1-propen-1-yl] -3-cepem-4-carboxylate. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3-[(1R-carbamoylethyl) dimethylammonio] -1-propen-1-yl] -3-cepem-4-carboxylate. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3-[(1R-carbamoyl-2-hydroxyethyl) dimethylammonio] -1-propen-1-yl] -3-cepem-4-carboxylate. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3- (5-Aza-1-methyl 2,8-dioxabicyclo [3,3,1] nona-1-io) -1-propen-1-yl] -3-cepem Compound that is -4-carboxylate. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3- (carbamoylmethylethylmethylammonio) -1-propen-1-yl] -3-cefe-4-carboxylate. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E)-[(2-oxopropyl) dimethylammonio] -1-propen-1-yl] -3-cefe-4-carboxylate. The compound according to claim 3, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3-yl)-(Z) -2-cyanomethoxyiminoacetamido] -3-[(E) -3-[(2-oxopropyl) dimethylammonio] -1-prop Phen-1-yl] -3-cefe-4-carboxylate. The method of claim 4, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3-[(1S-carbamoylethyl) dimethylammonio] -1-propen-1-yl] -3-cepem-4-carboxylate. The method of claim 4, wherein 7 β- [2- (5-amino-1,2,4-thiadiazol-3-yl)-(Z) -2-fluoromethoxyiminoacetamido] -3- [(E) -3-[(1R-carbamoylethyl) dimethylammonio] -1-propen-1-yl] -3-cepem-4-carboxylate. General formula Wherein R ₁ is a fluorine-substituted lower alkyl group or a cyano-substituted lower alkyl group, X is a halogen atom, a compound wherein the amino and / or carboxyl groups are protected by a protecting group or a salt thereof A ¹ (Wherein A ¹ is an amine corresponding to A) The following general formula by which the compound and functional group of react with the compound or its salt protected by a protecting group, and then removes a protecting group arbitrarily. Wherein R ₁ is as defined above and A is a cyclic or acyclic ammonium group; or a process for preparing a pharmaceutically acceptable salt thereof. General formula Wherein R ₁ is a fluorine substituted lower alkyl group or a cyano substituted lower alkyl group, A is a cyclic or acyclic amino group, or a pharmaceutically acceptable salt effective amount thereof and optionally pharmacologically Pharmaceutical compositions of acceptable carriers. The following general formula with antibacterial action Wherein R ₁ is a fluorine-substituted lower alkyl group or a cyano-substituted lower alkyl group, and A is a cyclic or acyclic amino group, or a pharmaceutically acceptable salt thereof. General formula Wherein R ₁ is a fluorine-substituted lower alkyl group or a cyano-substituted lower alkyl group, X is a halogen atom, a compound in which an amino group and / or a carboxyl group is protected by a protecting group, or a salt thereof. General formula (Wherein R ₁ is a fluorine-substituted lower alkyl group or a cyano-substituted lower alkyl group), a reactive acid derivative thereof, a compound whose amino group is protected by a protecting group or a salt thereof Wherein X is a halogen atom, a carboxyl group is reacted with a compound protected by a protecting group or a salt thereof, followed by optional removal of the protecting group and / or conversion of the halogen atom to another halogen atom (Wherein R_One And X is as defined above, wherein the compound of the amino group and / or the carboxyl group is protected by a protecting group or a salt thereof. The compound of the following general formula, the compound whose amino and / or carboxyl group was protected by the protecting group, or its salt. Wherein R ₆ is a carboxyl, halogenocarbonyl, carbamoyl or cyano group. (1) the following structural formula Wherein the compound of formula (amino and carboxyl groups are protected by a protecting group) or a salt thereof is reacted with halogenofluoromethane, and then the protecting group is optionally removed, or (2) Structural formula which hydrolyzes the compound of this, the compound whose amino group was protected by the protecting group, or its salt in presence of a base, and then removes a protecting group arbitrarily. A method for producing a compound or a salt thereof, wherein the compound, amino, and / or carboxyl group is protected by a protecting group. ※ Note: The disclosure is based on the initial application.