GB675422A - Preparation of amino esters of penicillin and salts thereof - Google Patents

Preparation of amino esters of penicillin and salts thereof

Info

Publication number
GB675422A
GB675422A GB14478/50A GB1447850A GB675422A GB 675422 A GB675422 A GB 675422A GB 14478/50 A GB14478/50 A GB 14478/50A GB 1447850 A GB1447850 A GB 1447850A GB 675422 A GB675422 A GB 675422A
Authority
GB
United Kingdom
Prior art keywords
penicillin
benzylpenicillin
ester
ester hydrochloride
melting point
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
GB14478/50A
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.)
KNUD ABILDGAARD ELLING
Original Assignee
KNUD ABILDGAARD ELLING
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
Application filed by KNUD ABILDGAARD ELLING filed Critical KNUD ABILDGAARD ELLING
Publication of GB675422A publication Critical patent/GB675422A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Amino esters of penicillin of general formula <FORM:0675422/IV (b)/1> are prepared by reacting a salt of penicillin with a tertiary amine halide of general formula <FORM:0675422/IV (b)/2> where X is halogen, R1 is divalent alkyl residue, and R2 and R3 are alkyl or aralkyl or in which R2 and R3 together with the nitrogen atom form a heterocyclic ring. The penicillin salt is dissolved or suspended in a diluent such as acetone, dimethylacetamide or tetrahydrofuran and excess of the tertiary amine halide is added with constant agitation for 20 or more hours. The ester may be isolated as such or as a salt with an inorganic or organic acid. Quaternary ammonium salts are prepared by reacting the ester with an alkyl halide, especially the iodide, or an alkyl sulphate, benzene sulphonate or toluenesulphonate. Specified salts of penicillin are sodium penicillin, procaine penicillin and triethylamine penicillin. Specified tertiary amine halides are diethylaminoethyl chloride, methyllaurylaminoethyl chloride, dimethylaminoethyl chloride, dimethylamino - 2 - chloro - propane, benzylethylaminoethylchloride, benzylmethylaminoethyl chloride, dibenzylaminoethyl chloride, N-(b - chloroethyl) - piperidine and N - (b - chloroethyl)-morpholine. The examples relate to the preparation of penicillin diethylaminoethyl ester hydrochloride, melting point 140-150 DEG C.; penicillin diethylaminoethyl ester hydroiodide, melting point 173-174 DEG C.; dimethyllaurylpenicillin-ethyl ester quaternary ammonium iodide; benzylpenicillin dimethylaminoethyl hydrochloride, melting point 156-157 DEG C.; benzylpenicillin dimethylaminoethyl hydroiodide, melting point 189.5 DEG C.; penicillin dimethylaminopropyl ester hydrochloride; penicillin benzylethylaminoethyl ester hydrochloride; benzylpenicillin - benzylmethylaminoethylester hydrochloride; benzylpenicillin - dibenzylaminoethyl ester hydrochloride; benzylpenicillin methyl laurylaminoethyl ester hydrochloride; benzyl penicillin-piperidinoethyl ester hydrochloride and the hydroiodide thereof, melting point 185 DEG C.; benzylpenicillin morpholino-ethyl ester hydrochloride.
GB14478/50A 1949-07-07 1950-06-09 Preparation of amino esters of penicillin and salts thereof Expired GB675422A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DK675422X 1949-07-07

Publications (1)

Publication Number Publication Date
GB675422A true GB675422A (en) 1952-07-09

Family

ID=8152181

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14478/50A Expired GB675422A (en) 1949-07-07 1950-06-09 Preparation of amino esters of penicillin and salts thereof

Country Status (1)

Country Link
GB (1) GB675422A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4081546A (en) * 1976-06-24 1978-03-28 Beecham Group Limited 3-substituted aminocycloalkyl esters of penicillin antibiotics
US4215120A (en) * 1977-07-14 1980-07-29 Beecham Group Limited Penicillin esters and their preparation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4081546A (en) * 1976-06-24 1978-03-28 Beecham Group Limited 3-substituted aminocycloalkyl esters of penicillin antibiotics
US4215120A (en) * 1977-07-14 1980-07-29 Beecham Group Limited Penicillin esters and their preparation

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