GB1217133A - Adriamycin and adriamycinone - Google Patents
Adriamycin and adriamycinoneInfo
- Publication number
- GB1217133A GB1217133A GB08719/69A GB1871969A GB1217133A GB 1217133 A GB1217133 A GB 1217133A GB 08719/69 A GB08719/69 A GB 08719/69A GB 1871969 A GB1871969 A GB 1871969A GB 1217133 A GB1217133 A GB 1217133A
- Authority
- GB
- United Kingdom
- 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
1,217,133. Preparing adriamycin. SOC. FARMACEUTICI ITALIA. 11 April, 1969 [12 April, 1968], No. 18719/69. Heading C2A. 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 |
|---|---|
| GB1217133A true GB1217133A (en) | 1970-12-31 |
Family
ID=11146828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08719/69A Expired GB1217133A (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) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB2125030A (en) * | 1982-08-13 | 1984-02-29 | Erba Farmitalia | Naphthacenequinone synthesis |
| 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 |
Families Citing this family (7)
| 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 |
| WO1986000073A1 (en) * | 1984-06-14 | 1986-01-03 | BIOGAL Gyógyszergyár | Process for preparing adriamycine and halide salts thereof |
| JP3112342B2 (en) * | 1992-06-10 | 2000-11-27 | 協和醗酵工業株式会社 | New compound UCE6 |
| EP0648503B1 (en) * | 1993-09-22 | 2000-07-26 | Hoechst Aktiengesellschaft | Pro-prodrugs, their production and use |
| GB9416007D0 (en) * | 1994-08-08 | 1994-09-28 | Erba Carlo Spa | Anthracyclinone derivatives |
| EP2824108B8 (en) * | 2012-03-06 | 2017-07-12 | Tianjin Hemay Oncology Pharmaceutical Co., Ltd. | Tetracyclic anthraquinone derivatives |
-
1969
- 1969-03-28 NL NL696904844A patent/NL145536B/en not_active IP Right Cessation
- 1969-04-07 YU YU858/69A patent/YU34389B/en unknown
- 1969-04-07 IL IL31966A patent/IL31966A/en unknown
- 1969-04-08 DE DE1917874A patent/DE1917874C3/en not_active Expired
- 1969-04-10 NO NO1464/69A patent/NO133271C/no unknown
- 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 FR FR6911030A patent/FR2007443A1/fr active Pending
- 1969-04-10 SE SE05048/69A patent/SE359293B/xx unknown
- 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 ES ES365907A patent/ES365907A1/en not_active Expired
- 1969-04-11 GB GB08719/69A patent/GB1217133A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB2125030A (en) * | 1982-08-13 | 1984-02-29 | Erba Farmitalia | Naphthacenequinone synthesis |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| NO133271B (en) | 1975-12-29 |
| IL31966A0 (en) | 1969-06-25 |
| DK126987B (en) | 1973-09-10 |
| CH518250A (en) | 1972-01-31 |
| ES365907A1 (en) | 1971-03-16 |
| SE359293B (en) | 1973-08-27 |
| IL31966A (en) | 1972-11-28 |
| NL6904844A (en) | 1969-10-14 |
| AT283597B (en) | 1970-08-10 |
| DE1917874B2 (en) | 1980-02-07 |
| NL145536B (en) | 1975-04-15 |
| DE1917874C3 (en) | 1980-10-02 |
| BE731398A (en) | 1969-10-13 |
| YU85869A (en) | 1978-12-31 |
| NO133271C (en) | 1976-04-07 |
| YU34389B (en) | 1979-07-10 |
| DE1917874A1 (en) | 1969-11-06 |
| FR2007443A1 (en) | 1970-01-09 |
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