GB796311A - Improvements in or relating to esters of spiramycins - Google Patents

Improvements in or relating to esters of spiramycins

Info

Publication number
GB796311A
GB796311A GB35916/56A GB3591656A GB796311A GB 796311 A GB796311 A GB 796311A GB 35916/56 A GB35916/56 A GB 35916/56A GB 3591656 A GB3591656 A GB 3591656A GB 796311 A GB796311 A GB 796311A
Authority
GB
United Kingdom
Prior art keywords
spiramycin
complex
triacetylspiramycin
tetrahydrospiramycin
iii
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
GB35916/56A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB796311A publication Critical patent/GB796311A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G11/00—Antibiotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention relates to a tasteless antibiotically active ester of a spiramycin antibiotic with a mono- or di-carboxylic acid of the aliphatic series or with an aromatic monocyclic monocarboxylic acid. The spiramycin antibiotic is (a) spiramycin complex, (b) spiramycin I, (c) spiramycin II, (d) spiramycin III, (e) hydrogenated spiramycin as in (a), (b), (c) or (d) containing at the most four hydrogen atoms due to hydrogenation and particularly tetrahydrospiramycin, dihydrospiramycin I, tetrahydrospiramycin II and tetrahydrospiramycin III. The esters are obtained by acylation, preferably by means of the appropriate acid halide or anhydride. The reaction may take place in the presence of an organic solvent and preferably in the presence of a basic substance such as an alkali metal carbonate or bicarbonate, a tertiary amine or a heterocyclic tertiary base such as pyridine or alkylpiperidines. The temperature should be below 120 DEG C. One or more of the four esterifiable groups of the spiramycin may be esterified. The examples describe the preparation of (a) monoethoxyformylspiramycin from spiramycin complex, sodium bicarbonate and ethylchlorocarbonate in acetone; (b) tetrabenzoylspiramycin from spiramycin complex, sodium carbonate and benzoyl chloride; (c) distearoylspiramycin from spiramycin complex, stearoyl chloride and triethylamine in toluene; (d) monostearoylspiramycin; (e) triacetylspiramycin from spiramycin complex, acetic anhydride and pyridine; (f) triacetyltetrahydrospiramycin; (g) monoethoxyformyltetrahydrospiramycin from tetrahydrospiramycin, ethylchlorocarbonate and triethylamine in toluene; (h) triacetylspiramycin I; (i) triacetylspiramycin II; (j) triacetylspiramycin III; (k) monoethoxyformylspiramycin I; (l) monoethoxyformylspiramycin II; (m) monoethoxyformyl spiramycin III; (n) monosuccinyl spiramycin from spiramycin complex, succinic anhydride in ethyl acetate; (o) disuccinylspiramycin; (p) dimaleylspiramycin from spiramycin complex and maleic anhydride in benzene. Specifications 758,726, 785,098, and 785,191 are referred to.
GB35916/56A 1955-12-01 1956-11-23 Improvements in or relating to esters of spiramycins Expired GB796311A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR796311X 1955-12-01

Publications (1)

Publication Number Publication Date
GB796311A true GB796311A (en) 1958-06-11

Family

ID=9235070

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35916/56A Expired GB796311A (en) 1955-12-01 1956-11-23 Improvements in or relating to esters of spiramycins

Country Status (1)

Country Link
GB (1) GB796311A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3039874A (en) * 1959-04-04 1962-06-19 Rhone Poulenc Sa Compositions for the nutrition of animals
US3472930A (en) * 1966-01-06 1969-10-14 Rhone Poulenc Sa Spiramycin derivative
US4174391A (en) * 1976-12-08 1979-11-13 May & Baker Limited Spiramycin esters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3039874A (en) * 1959-04-04 1962-06-19 Rhone Poulenc Sa Compositions for the nutrition of animals
US3472930A (en) * 1966-01-06 1969-10-14 Rhone Poulenc Sa Spiramycin derivative
US4174391A (en) * 1976-12-08 1979-11-13 May & Baker Limited Spiramycin esters

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