NL7216568A - Antibiotic 8-hydroxy-erythromycin A - prepd. by oxidn. of 8,9-anhydroerythro-mycin A 6,9-hemiketal and redn. of the prod. - Google Patents

Antibiotic 8-hydroxy-erythromycin A - prepd. by oxidn. of 8,9-anhydroerythro-mycin A 6,9-hemiketal and redn. of the prod.

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Publication number
NL7216568A
NL7216568A NL7216568A NL7216568A NL7216568A NL 7216568 A NL7216568 A NL 7216568A NL 7216568 A NL7216568 A NL 7216568A NL 7216568 A NL7216568 A NL 7216568A NL 7216568 A NL7216568 A NL 7216568A
Authority
NL
Netherlands
Prior art keywords
erythromycin
hemiketal
alkyl
oxide
prepd
Prior art date
Application number
NL7216568A
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 filed Critical
Priority to NL7216568A priority Critical patent/NL7216568A/en
Publication of NL7216568A publication Critical patent/NL7216568A/en

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Classifications

    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

8-Hydroxy-erythromycin A (I). its monohydrate, and its 1-4 C alkyl 6,9-ketals and 6911-spiroketals, as well as salts and esters of these cpds., are prepd. by reacting 8,9-anhydroerythromycin A 6,9-hemiketal (II) with a preacid in the presence of (a) a mixt. of ethyl acetate and H2O to form the N-oxide of I 6,9-hemiketal, or (b) of a 1-4 C alkanol to form the N-oxide of a 1-4 C alkyl 6,9-ketal of I, or (c) of an anhydrous aprotic solvent to form the N-oxide of I 6911-spiroketal, and then the desired reaction prod. of (a), (b) or (c) is reduced with H2 in the presence of a heavy metal catalyst to give I (or I 1-4C alkyl, 6,9-ketal or I 6911-spiroketal which are opt. acidically hydrolysed to I). Reaction of I with >= equiv. amt. of 2-4 C alkanoic acid anhydride gives 2"-(2-4 C alkanoate) or 2',4",11-tri(2-4 C alkanoate) of I, resp. Antimicrobial spectrum of I is comparable to that of erythromycin A. It gives antibiotically effective blood levels in mammals and is more stable towards acids than erythromycin A.
NL7216568A 1972-12-06 1972-12-06 Antibiotic 8-hydroxy-erythromycin A - prepd. by oxidn. of 8,9-anhydroerythro-mycin A 6,9-hemiketal and redn. of the prod. NL7216568A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NL7216568A NL7216568A (en) 1972-12-06 1972-12-06 Antibiotic 8-hydroxy-erythromycin A - prepd. by oxidn. of 8,9-anhydroerythro-mycin A 6,9-hemiketal and redn. of the prod.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL7216568A NL7216568A (en) 1972-12-06 1972-12-06 Antibiotic 8-hydroxy-erythromycin A - prepd. by oxidn. of 8,9-anhydroerythro-mycin A 6,9-hemiketal and redn. of the prod.

Publications (1)

Publication Number Publication Date
NL7216568A true NL7216568A (en) 1974-06-10

Family

ID=19817493

Family Applications (1)

Application Number Title Priority Date Filing Date
NL7216568A NL7216568A (en) 1972-12-06 1972-12-06 Antibiotic 8-hydroxy-erythromycin A - prepd. by oxidn. of 8,9-anhydroerythro-mycin A 6,9-hemiketal and redn. of the prod.

Country Status (1)

Country Link
NL (1) NL7216568A (en)

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