ES365907A1 - Adriamycin and adriamycinone - Google Patents
Adriamycin and adriamycinoneInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design 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.
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)
| 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 |
-
1969
- 1969-03-28 NL NL696904844A patent/NL145536B/en not_active IP Right Cessation
- 1969-04-07 IL IL31966A patent/IL31966A/en unknown
- 1969-04-07 YU YU858/69A patent/YU34389B/en unknown
- 1969-04-08 DE DE1917874A patent/DE1917874C3/en not_active Expired
- 1969-04-10 DK DK197469AA patent/DK126987B/en unknown
- 1969-04-10 AT AT347269A patent/AT283597B/en not_active IP Right Cessation
- 1969-04-10 SE SE05048/69A patent/SE359293B/xx unknown
- 1969-04-10 NO NO1464/69A patent/NO133271C/no unknown
- 1969-04-10 FR FR6911030A patent/FR2007443A1/fr active Pending
- 1969-04-11 CH CH557169A patent/CH518250A/en not_active IP Right Cessation
- 1969-04-11 BE BE731398D patent/BE731398A/en not_active IP Right Cessation
- 1969-04-11 GB GB08719/69A patent/GB1217133A/en not_active Expired
- 1969-04-11 ES ES365907A patent/ES365907A1/en not_active Expired
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 |