# US 4,395,412 A · 7.alpha.-Methoxycephalosporins > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,395,412 A - Document ID: US4395412A - Status: Granted - Kind: A - Application number: 06/221,622 - Filed: 1980-12-31 - Granted: 1983-07-26 - Earliest claimed: 1977-07-23 - Assignees: Toyama Chemical Co., Ltd. - Inventors: Isamu Saikawa; Shuntaro Takano; Hiroyuki Imaizumi; Isamu Takakura; Hirokazu Ochiai; Takashi Yasuda; Hideo Taki; Masaru Tai; Yutaka Kodama - Web page: https://patentgrep.com/patent/US4395412A ## CPC - C07D 295/20: by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof - Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract A 7.alpha.-methoxycephalosporin represented by the general formula: ##STR1## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group; R.sup.2 represents an organic group linked to the carbon atom through an oxygen or sulfur atom; R.sup.3 represents a lower alkyl group; n is 0, 1 or 2; A represents a hydrogen atom or a substituted or unsubstituted alkyl group; and B represents a substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl or heterocyclic group, and a salt thereof. These compounds have a broad antibacterial spectrum, high resistance to .beta.-lactamase produced from bacteria, and an effective antibacterial activity against clinical isolates of bacteria. ## Claims ### Claim 1 A 7.alpha.-methoxy-cephalosporin or a salt thereof, said 7.alpha.-methoxy-cephalosporin being represented by the formula ##STR90## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group; R.sup.2 represents a substituted or unsubstituted lower alkoxy, lower alkylthio, or C.sub.1-10 acyloxy group, the substituent of the substituted group being selected from halogen, lower alkyl, phenyl, C.sub.2-5 alkenyl, hydroxyl, lower alkoxy, lower alkylthio, nitro, cyano, lower alkylamino, di-lower alkylamino, C.sub.1-10 acylamino, C.sub.1-10 acyl, C.sub.1-10 acyloxy, C.sub.1-10 acyl-lower alkyl, carboxyl, carbamoyl, amino-lower alkyl, N-lower alkylamino-lower alkyl, N,N-di-lower alkylamino-lower alkyl, hydroxy-lower alkyl, hydroxyimino-lower alkyl, lower alkoxy-lower alkyl, carboxyl-lower alkyl, sulfo-lower alkyl, sulfo, sulfamoyl-lower alkyl, sulfamoyl, carbamoyl-lower alkyl, carbamoyl-C.sub.2-5 alkenyl, and N-hydroxycarbamoyl-lower alkyl; R.sup.3 represents a lower alkyl group; n is 0, 1 or 2; A represents a hydrogen atom or a substituted or unsubstituted straight or branched chain C.sub.1-14 alkyl group, the substituent of the substituted group being selected from halogen, lower alkoxy, cyano, nitro, carboxyl, lower alkoxycarbonyl, lower alkylthio, and C.sub.1-10 acyl; and B represents a substituted or unsubstituted C.sub.5-6 cycloalkyl, C.sub.5-6 cycloalkenyl, C.sub.5-6 cycloalkadienyl or heterocyclic group, said heterocyclic group being composed of a 5 or 6 membered aromatic heterocyclic ring which is composed of carbon and at least one hetero atom selected from S, O and N, or of said aromatic heterocyclic ring fused to a benzene ring, the substituent of the substituted group being selected from halogen, lower alkyl, lower alkoxy, hydroxyl, C.sub.1-10 acyl, C.sub.1-10 acyloxy, mercapto, lower alkylthio, nitro, amino, protected amino, imino, protected imino, and carboxyl. ### Claim 2 (depends on 1) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 1, wherein B represents a heterocyclic group. ### Claim 3 (depends on 2) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 2, wherein B represents a thienyl group. ### Claim 4 (depends on 3) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 3, wherein A represents a lower alkyl group and n is 0. ### Claim 5 (depends on 4) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 4, wherein B represents a 2-thienyl group. ### Claim 6 (depends on 3, 4) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 3 or 4, wherein R.sup.2 represents an acetoxy group. ### Claim 7 (depends on 2) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 2, wherein B represents a furyl group. ### Claim 8 (depends on 7) A 7.alpha.-methoxycephalosporin or a salt thereof at its acidic group according to claim 7, wherein A represents a lower alkyl group and n is 0. ### Claim 9 (depends on 7, 8) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 7 or 8, wherein R.sup.2 represents an acetoxy group. ### Claim 10 (depends on 2) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 2, wherein B represents ##STR91## or its tautomer, ##STR92## where R.sup.4 represents an amino group or protected amino group and R.sup.5 represents an imino group or protected imino group. ### Claim 11 (depends on 10) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 10, wherein A represents a lower alkyl group and n is 0. ### Claim 12 (depends on 10, 11) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 10 or 11, wherein R.sup.2 represents an acetoxy group. ### Claim 13 (depends on 1) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 1, wherein B represents 1,4-cyclohexadienyl group. ### Claim 14 (depends on 13) A 7.alpha.-methoxycephalosporin or a salt thereof at its acidic group according to claim 13, wherein A represents a lower alkyl group and n is 0. ### Claim 15 (depends on 13, 14) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 13 or 14, wherein R.sup.2 represents an acetoxy group. ### Claim 16 (depends on 1) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 1, wherein A represents a lower alkyl group, n is 0, B represents a thienyl, furyl or 2-aminothiazolyl group, and R.sup.2 represents an acetoxy group. ### Claim 17 (depends on 16) A 7.alpha.-methoxycephalosporin or a pharmaceutically acceptable salt thereof according to claim 16, wherein A represents ethyl group and B represents 2-thienyl group. ### Claim 18 (depends on 1) A 7.alpha.-methoxycephalosporin or a salt thereof according to claim 1, wherein A represents a hydrogen atom, n is 0, B represents a thienyl, furyl or 2-aminothiazolyl group, and R.sup.2 represents an acetoxy group. ### Claim 19 (depends on 1) A pharmaceutical composition useful for treating bacterial infections in humans and mammals which comprises an antibacterially effective amount of a compound or its pharmaceutically acceptable salt as claimed in claim 1, in combination with a pharmaceutically acceptable inert diluent or carrier. ### Claim 20 7.bet a.-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(2-thi enyl)-acetamido]-7.alpha.-methoxy-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid, or a pharmaceutically acceptable salt thereof. ### Claim 21 7.beta.-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-.alph a.-(1,4-cyclohexadienyl)-acetamido]-7.alpha.-methoxy-3-acetoxymethyl-.DELTA ..sup.3 -cephem-4-carboxylic acid, or a pharmaceutically acceptable salt thereof. ### Claim 22 7.bet a.-[D-.alpha.-(2-amino-4-thiazolyl)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazine carboxamido)-acetamido]-7.alpha.-methoxy-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid, or a pharmaceutically acceptable salt thereof. ### Claim 23 7.beta.-[D(-)-.alpha.-(2,3-dioxo-1-piperazinecarboxamido)-.alpha.-(2-th ienyl)-acetamido]-7.alpha.-methoxy-3-acetoxymethyl-.DELTA..sup.3 -cephen-4-carboxylic acid, or a pharmaceutically acceptable salt thereof.