ES365907A1 - Adriamycin and adriamycinone - Google Patents

Adriamycin and adriamycinone

Info

Publication number
ES365907A1
ES365907A1 ES365907A ES365907A ES365907A1 ES 365907 A1 ES365907 A1 ES 365907A1 ES 365907 A ES365907 A ES 365907A ES 365907 A ES365907 A ES 365907A ES 365907 A1 ES365907 A1 ES 365907A1
Authority
ES
Spain
Prior art keywords
adriamycin
group
acid
aglycone
alkali
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
ES365907A
Other languages
Spanish (es)
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.)
FARMACEUTII ITALIA SOC
Original Assignee
FARMACEUTII ITALIA SOC
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 FARMACEUTII ITALIA SOC filed Critical FARMACEUTII ITALIA SOC
Publication of ES365907A1 publication Critical patent/ES365907A1/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/24Condensed ring systems having three or more rings
    • C07H15/252Naphthacene radicals, e.g. daunomycins, adriamycins
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

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

Abstract

The antibiotic adriamycin or its aglycone adriamycinone having the Formula I and non-toxic acid-addition salts of adriamycin are prepared by reacting daunomycin or an N- protected derivative thereof or the aglycone with bromine or iodine to convert the 14-CH 3 group to a 14-CH 2 Br or a 14-CH 2 I group and either reacting with alkali metal acetate to give the 14-acetoxy derivative which is then hydrolysed with alkali to the required 14-CH 2 OH group of adriamycin or, in the ease of the 14-CH 2 Br group, hydrolysing this directly with alkali to the 14-CH 2 OH group, then removing the N-protecting gtoup and optionally converting the adriamycin to an acid-addition salt. N-protecting groups may be the trifluoroacetyl group or the Schiff base with salicaldehyde, which are removed by treatment with ethyl chloroformate and p-toluene-sulphonic acid followed by alkaline hydrolysis in the case of the acyl group or acid hydrolysis when the Schiff base is used. The initial halogenation is carried out in an inert solvent, preferably in the presence of CaO when the halogen is iodine, in an inert atmosphere. Pharmaceutical compositions comprise the antibiotic adriamycin or its aglycone, of Formula I above, or a non-toxic acid-addition salt of adriamycin, when prepared by the aforesaid process, together with a pharmaceutical diluent or carrier.
ES365907A 1968-04-12 1969-04-11 Adriamycin and adriamycinone Expired ES365907A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT1515968 1968-04-12

Publications (1)

Publication Number Publication Date
ES365907A1 true ES365907A1 (en) 1971-03-16

Family

ID=11146828

Family Applications (1)

Application Number Title Priority Date Filing Date
ES365907A Expired ES365907A1 (en) 1968-04-12 1969-04-11 Adriamycin and adriamycinone

Country Status (13)

Country Link
AT (1) AT283597B (en)
BE (1) BE731398A (en)
CH (1) CH518250A (en)
DE (1) DE1917874C3 (en)
DK (1) DK126987B (en)
ES (1) ES365907A1 (en)
FR (1) FR2007443A1 (en)
GB (1) GB1217133A (en)
IL (1) IL31966A (en)
NL (1) NL145536B (en)
NO (1) NO133271C (en)
SE (1) SE359293B (en)
YU (1) YU34389B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2160716A1 (en) * 1971-11-23 1973-07-06 Rhone Poulenc Sa Antibiotics duborimycin and 27706rp - by reduction of daunorubicin and adriamycin
FR2135221A1 (en) * 1971-05-04 1972-12-15 Farmaceutici Italia Doxorubicin 14-esters prepn - by treating 14-bromodaunomycin with a salt of the corresp acid
US4201773A (en) * 1978-07-26 1980-05-06 The United States Of America As Represented By The Department Of Health, Education And Welfare 7-O-(2,6-Dideoxy-α-L-lyxo-hexopyranosyl)-daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone
US4348388A (en) * 1980-04-02 1982-09-07 G.D. Searle & Co. 11-Amino-11-deoxydaunorubicin and analogs
GB2125030B (en) * 1982-08-13 1986-11-26 Erba Farmitalia Naphthacenequinone synthesis
JPS61502956A (en) * 1984-06-14 1986-12-18 ビオガル ジヨジセルジヤ−ル Method for preparing adriamycin and its halide salts
GB2169285A (en) * 1985-01-05 1986-07-09 Erba Farmitalia 4'-Deoxydoxorubicin-14-esters
GB2169284A (en) * 1985-01-05 1986-07-09 Erba Farmitalia 4'-Epidoxorubicin-14-esters
GB2169286A (en) * 1985-01-05 1986-07-09 Erba Farmitalia 4'-Deoxy-4'-halodoxorubicin-14-esters
JP3112342B2 (en) * 1992-06-10 2000-11-27 協和醗酵工業株式会社 New compound UCE6
DK0648503T3 (en) * 1993-09-22 2000-10-02 Hoechst Ag Pro-prodrugs, their manufacture and use
GB9416007D0 (en) * 1994-08-08 1994-09-28 Erba Carlo Spa Anthracyclinone derivatives
CN104125962B (en) * 2012-03-06 2016-06-22 天津和美生物技术有限公司 Fourth Ring anthraquinone derivative

Also Published As

Publication number Publication date
NL6904844A (en) 1969-10-14
YU34389B (en) 1979-07-10
DK126987B (en) 1973-09-10
BE731398A (en) 1969-10-13
DE1917874A1 (en) 1969-11-06
NO133271C (en) 1976-04-07
NL145536B (en) 1975-04-15
CH518250A (en) 1972-01-31
IL31966A0 (en) 1969-06-25
IL31966A (en) 1972-11-28
GB1217133A (en) 1970-12-31
DE1917874C3 (en) 1980-10-02
NO133271B (en) 1975-12-29
DE1917874B2 (en) 1980-02-07
YU85869A (en) 1978-12-31
SE359293B (en) 1973-08-27
AT283597B (en) 1970-08-10
FR2007443A1 (en) 1970-01-09

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19900227