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
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 title abstract 14
- 229940009456 adriamycin Drugs 0.000 title abstract 7
- IBZGBXXTIGCACK-CWKPULSASA-N Adriamycinone Chemical compound C1[C@@](O)(C(=O)CO)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O IBZGBXXTIGCACK-CWKPULSASA-N 0.000 title abstract 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 abstract 3
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 abstract 3
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000002262 Schiff base Substances 0.000 abstract 2
- 150000004753 Schiff bases Chemical class 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 230000003115 biocidal effect Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal acetate Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 abstract 1
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 |
| EP0183691A1 (en) * | 1984-06-14 | 1986-06-11 | Biogal Gyogyszergyar | Process for preparing adriamycine and halide salts thereof |
| GB2169285A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Deoxydoxorubicin-14-esters |
| GB2169286A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Deoxy-4'-halodoxorubicin-14-esters |
| GB2169284A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Epidoxorubicin-14-esters |
| JP3112342B2 (en) * | 1992-06-10 | 2000-11-27 | 協和醗酵工業株式会社 | New compound UCE6 |
| DE69425356T2 (en) * | 1993-09-22 | 2002-04-18 | Hoechst Ag | Pro-prodrugs, their manufacture and use |
| GB9416007D0 (en) * | 1994-08-08 | 1994-09-28 | Erba Carlo Spa | Anthracyclinone derivatives |
| US9670242B2 (en) * | 2012-03-06 | 2017-06-06 | 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 SE SE05048/69A patent/SE359293B/xx unknown
- 1969-04-10 DK DK197469AA patent/DK126987B/en unknown
- 1969-04-10 FR FR6911030A patent/FR2007443A1/fr active Pending
- 1969-04-10 AT AT347269A patent/AT283597B/en not_active IP Right Cessation
- 1969-04-11 CH CH557169A patent/CH518250A/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
- 1969-04-11 BE BE731398D patent/BE731398A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE1917874A1 (en) | 1969-11-06 |
| CH518250A (en) | 1972-01-31 |
| YU34389B (en) | 1979-07-10 |
| DK126987B (en) | 1973-09-10 |
| IL31966A0 (en) | 1969-06-25 |
| NO133271C (en) | 1976-04-07 |
| AT283597B (en) | 1970-08-10 |
| DE1917874B2 (en) | 1980-02-07 |
| YU85869A (en) | 1978-12-31 |
| SE359293B (en) | 1973-08-27 |
| IL31966A (en) | 1972-11-28 |
| BE731398A (en) | 1969-10-13 |
| NL6904844A (en) | 1969-10-14 |
| NL145536B (en) | 1975-04-15 |
| DE1917874C3 (en) | 1980-10-02 |
| GB1217133A (en) | 1970-12-31 |
| NO133271B (en) | 1975-12-29 |
| FR2007443A1 (en) | 1970-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19900227 |