GB957570A - Heterocyclic antimicrobial agents and processes for their preparation - Google Patents

Heterocyclic antimicrobial agents and processes for their preparation

Info

Publication number
GB957570A
GB957570A GB1691862A GB1691862A GB957570A GB 957570 A GB957570 A GB 957570A GB 1691862 A GB1691862 A GB 1691862A GB 1691862 A GB1691862 A GB 1691862A GB 957570 A GB957570 A GB 957570A
Authority
GB
United Kingdom
Prior art keywords
acid
carboxyamido
reaction
phenylthiophene
prepared
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1691862A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US162573A external-priority patent/US3131184A/en
Priority claimed from US162572A external-priority patent/US3252971A/en
Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB957570A publication Critical patent/GB957570A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds of the structure: <FORM:0957570/C2/1> wherein R 1 has the structure: <FORM:0957570/C2/2> <FORM:0957570/C2/3> <FORM:0957570/C2/4> <FORM:0957570/C2/5> <FORM:0957570/C2/6> in which B is hydrogen, alkanoyl or benzoyl, A is a quaternary amine, M is hydrogen or a pharmaceutically acceptable non-toxic cation, and Y is the residue of pyrrole, furan, thiophene, indole, benzofuran, thionaphthene, pyrazole, imidazole, isothiazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyridazine, pyrimidine, pyrazine or quinoxaline, are prepared by treating a compound of the formula: <FORM:0957570/C2/7> with an acid chloride or bromide of an acid of the formula: <FORM:0957570/C2/8> The Specification describes the production of many compounds of the above formula of which the following are typical: 6-(2-phenylthianaphthene-3-carboxyamido) penicillanic acid, 6-(3-phenyl-benzofuran -2-carboxyamido)-penicillanic acid, 7-(3-phenylthianaphthene-2-carboxyamido)-cephalosporanic acid and 7-(2-phenylbenzofuran-3-carboxyamido) cephalosporanic acid. In the cephalosporanic acid derivatives the acetoxy group in the 3-position may be modified to form a lactone by hydrolysis and internal esterification may be removed by treatment with citrus acetylesterase and the resulting free hydroxyl group re-esterified, may be removed by hydrogenation to form a methyl group or by treatment with a tertiary amine to form a quaternary inner salt. The compounds of the invention may be made up into pharmaceutical compositions in conjunction with a pharmaceutical carrier. 3-phenylindole-2-carboxylic acid is prepared by hydrolysis of ethyl 3-phenylindole-2-carboxylate which is obtained by the reaction of concentrated sulphuric acid and ethanol on the phenylhydrazone of phenylpyruvic acid. 2-phenylthiophene-3-carboxylic acid is prepared by the reaction of an aqueous solution of silver nitrate and sodium hydroxide on 2-phenyl-3-thienaldehyde which is obtained by the reaction of hexamethylene tetramine and water on 3-bromomethyl-2-phenylthiophene which is obtained by the reaction of N-bromosuccinimide on 3-methyl-2-phenylthiophene. Specifications 953,695 and 957,569 are referred to.
GB1691862A 1961-05-03 1962-05-02 Heterocyclic antimicrobial agents and processes for their preparation Expired GB957570A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11398161A 1961-05-03 1961-05-03
US162573A US3131184A (en) 1961-12-27 1961-12-27 Derivatives of 7-aminocephalosporanic acid
US162572A US3252971A (en) 1961-12-27 1961-12-27 Fused benzoheterocyclic derivatives of 6-aminopenicillanic acid

Publications (1)

Publication Number Publication Date
GB957570A true GB957570A (en) 1964-05-06

Family

ID=27381423

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1691862A Expired GB957570A (en) 1961-05-03 1962-05-02 Heterocyclic antimicrobial agents and processes for their preparation

Country Status (1)

Country Link
GB (1) GB957570A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3284446A (en) * 1964-11-24 1966-11-08 R & L Molecular Research Ltd Ortho-(5-tetrazolyl) phenylpenicillins
US3311611A (en) * 1965-12-20 1967-03-28 R & L Molecular Research Ltd Derivatives of 6-aminopenicillanic acid
US3499909A (en) * 1966-05-18 1970-03-10 Koninklijke Gist Spiritus Process for production of 6-aminopenicillanic acid
FR2102209A1 (en) * 1970-08-12 1972-04-07 Chinoin Gyogyszer Es Vegyeszet

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3284446A (en) * 1964-11-24 1966-11-08 R & L Molecular Research Ltd Ortho-(5-tetrazolyl) phenylpenicillins
US3311611A (en) * 1965-12-20 1967-03-28 R & L Molecular Research Ltd Derivatives of 6-aminopenicillanic acid
US3499909A (en) * 1966-05-18 1970-03-10 Koninklijke Gist Spiritus Process for production of 6-aminopenicillanic acid
FR2102209A1 (en) * 1970-08-12 1972-04-07 Chinoin Gyogyszer Es Vegyeszet

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