ATE195526T1 - Verfahren zur herstellung von epirubicin oder zusatzsalzen davon, von daunorubicin - Google Patents
Verfahren zur herstellung von epirubicin oder zusatzsalzen davon, von daunorubicinInfo
- Publication number
- ATE195526T1 ATE195526T1 AT96203554T AT96203554T ATE195526T1 AT E195526 T1 ATE195526 T1 AT E195526T1 AT 96203554 T AT96203554 T AT 96203554T AT 96203554 T AT96203554 T AT 96203554T AT E195526 T1 ATE195526 T1 AT E195526T1
- Authority
- AT
- Austria
- Prior art keywords
- daunosamine
- daunomycinone
- daunorubicin
- group
- converted
- Prior art date
Links
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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-VTZDEGQISA-N 0.000 title abstract 3
- 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 title abstract 3
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 title abstract 3
- 229960000975 daunorubicin Drugs 0.000 title abstract 3
- 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 title abstract 3
- 229960001904 epirubicin Drugs 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- WPJRFCZKZXBUNI-HCWXCVPCSA-N daunosamine Chemical compound C[C@H](O)[C@@H](O)[C@@H](N)CC=O WPJRFCZKZXBUNI-HCWXCVPCSA-N 0.000 abstract 5
- YOFDHOWPGULAQF-UHFFFAOYSA-N Daunomycin-Aglycone Natural products C1C(O)(C(C)=O)CC(O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-UHFFFAOYSA-N 0.000 abstract 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 3
- YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 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 2
- 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 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 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 2
- 238000000034 method Methods 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 238000006137 acetoxylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 239000000126 substance Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96203554A EP0848009B1 (de) | 1996-12-16 | 1996-12-16 | Verfahren zur Herstellung von Epirubicin oder Zusatzsalzen davon, von Daunorubicin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE195526T1 true ATE195526T1 (de) | 2000-09-15 |
Family
ID=8224702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT96203554T ATE195526T1 (de) | 1996-12-16 | 1996-12-16 | Verfahren zur herstellung von epirubicin oder zusatzsalzen davon, von daunorubicin |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5874550A (de) |
| EP (1) | EP0848009B1 (de) |
| JP (1) | JP4176845B2 (de) |
| AT (1) | ATE195526T1 (de) |
| CA (1) | CA2224764C (de) |
| DE (1) | DE69609845T2 (de) |
| DK (1) | DK0848009T3 (de) |
| ES (1) | ES2151632T3 (de) |
| GR (1) | GR3034608T3 (de) |
| PT (1) | PT848009E (de) |
| SI (1) | SI0848009T1 (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100785966B1 (ko) * | 2000-08-10 | 2007-12-14 | 동아제약주식회사 | 안트라싸이클린계 항암제인 에피루비신 및 약학적으로허용되는 그 염의 제조방법 |
| KR100850408B1 (ko) * | 2000-08-10 | 2008-08-04 | 동아제약주식회사 | 안트라싸이클린계 항암제인 에피루비신 및 약학적으로허용되는 그 염의 제조방법 |
| CN100412084C (zh) * | 2003-07-02 | 2008-08-20 | 獀洛克斯股份有限公司 | 热稳定的结晶盐酸表柔比星及其制造方法 |
| US20090099346A1 (en) * | 2003-07-02 | 2009-04-16 | Victor Matvienko | Thermally stable crystalline epirubicin hydrochloride |
| US7388083B2 (en) * | 2005-03-07 | 2008-06-17 | Solux Corporation | Epimerization of 4′-C bond and modification of 14-CH3-(CO)-fragment in anthracyclin antibiotics |
| WO2006111561A1 (en) * | 2005-04-21 | 2006-10-26 | Dsm Ip Assets B.V. | Improved microbial production of anthracyclins |
| DE06848583T1 (de) | 2005-12-13 | 2011-03-17 | Solux Corporation, San Diego | Verfahren zur herstellung von 4-demethyldaunorubicin |
| US8802830B2 (en) * | 2005-12-20 | 2014-08-12 | Solux Corporation | Synthesis of epirubicin from 13-dihydrodaunorubicine |
| EP1990405B1 (de) * | 2007-05-08 | 2017-07-26 | Provivo Oy | Genetisch modifizierte Stämme zur Produktion von Anthracyclin-Metaboliten, die als Krebsheilmittel dienen können |
| US8357785B2 (en) * | 2008-01-08 | 2013-01-22 | Solux Corporation | Method of aralkylation of 4′-hydroxyl group of anthracylins |
| WO2010028667A1 (en) * | 2008-09-11 | 2010-03-18 | W.C. Heraeus Gmbh | Genetically modified strains for biotransformations in anthracycline production |
| PL2301943T3 (pl) | 2009-09-08 | 2014-06-30 | Heraeus Precious Metals Gmbh | Krystalizacja epidaunorubicyny x HCI |
| KR101125460B1 (ko) | 2010-03-24 | 2012-03-28 | 동아제약주식회사 | 에피루비신 염산염의 신규한 결정형 |
| DE102011103751A1 (de) | 2011-05-31 | 2012-12-06 | Heraeus Precious Metals Gmbh & Co. Kg | Kristallisierung von Epirubicinhydrochlorid |
| DE102011111991A1 (de) * | 2011-08-30 | 2013-02-28 | Lead Discovery Center Gmbh | Neue Cyclosporin-Derivate |
| US9963479B2 (en) | 2013-07-02 | 2018-05-08 | Zhejiang Hisun Pharmaceutical Co., Ltd. | Method for preparing epirubicin and intermediate thereof |
| TWI712611B (zh) | 2015-03-30 | 2020-12-11 | 日商明治製菓藥業股份有限公司 | 泛艾黴素之製造方法及其新穎之製造中間體 |
| CN104861014B (zh) * | 2015-06-03 | 2017-09-29 | 道中道（菏泽）制药有限公司 | 一种盐酸表阿霉素结晶的制备方法 |
| WO2017120729A1 (zh) * | 2016-01-11 | 2017-07-20 | 浙江海正药业股份有限公司 | 一种盐酸表柔比星的制备方法及其中间体 |
| CN112574267A (zh) * | 2019-09-28 | 2021-03-30 | 鲁南制药集团股份有限公司 | 一种盐酸表柔比星中间体化合物iii |
| CN114149473B (zh) * | 2020-09-08 | 2024-03-15 | 鲁南制药集团股份有限公司 | 一种盐酸表柔比星的合成方法及其中间体 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803124A (en) | 1968-04-12 | 1974-04-09 | Farmaceutici It Soc | Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives |
| GB1457632A (en) | 1974-03-22 | 1976-12-08 | Farmaceutici Italia | Adriamycins |
| FI860683A7 (fi) | 1984-06-14 | 1986-02-14 | Biogal Gyogyszergyar | Menetelmä adriamysiinin ja sen halidisuolojen valmistamiseksi. |
| GB8519452D0 (en) * | 1985-08-02 | 1985-09-11 | Erba Farmitalia | Injectable solutions |
| IT1196503B (it) | 1986-07-16 | 1988-11-16 | Erba Farmitalia | Procedimento continuo per la trasformazione di 4'-cheto-n-trifluoroacetildaunorubicina in 4'-epi-trifluoroacetildaunorubicina,internmedio per la preparazione di un composto |
| IT1230505B (it) * | 1988-10-11 | 1991-10-25 | Sicor Spa | Procedimento per la conversione della daunorubicina in doxorubicina. |
| IT1275953B1 (it) * | 1995-03-22 | 1997-10-24 | Sicor Spa | Procedimento per la preparazione di antibiotici della classe delle antracicline |
-
1996
- 1996-12-16 AT AT96203554T patent/ATE195526T1/de not_active IP Right Cessation
- 1996-12-16 DE DE69609845T patent/DE69609845T2/de not_active Expired - Fee Related
- 1996-12-16 PT PT96203554T patent/PT848009E/pt unknown
- 1996-12-16 ES ES96203554T patent/ES2151632T3/es not_active Expired - Lifetime
- 1996-12-16 DK DK96203554T patent/DK0848009T3/da active
- 1996-12-16 SI SI9630241T patent/SI0848009T1/xx unknown
- 1996-12-16 EP EP96203554A patent/EP0848009B1/de not_active Expired - Lifetime
-
1997
- 1997-01-14 JP JP00494697A patent/JP4176845B2/ja not_active Expired - Fee Related
- 1997-12-04 US US08/985,358 patent/US5874550A/en not_active Expired - Fee Related
- 1997-12-15 CA CA002224764A patent/CA2224764C/en not_active Expired - Fee Related
-
2000
- 2000-10-12 GR GR20000402292T patent/GR3034608T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2224764C (en) | 2006-10-03 |
| DK0848009T3 (da) | 2000-11-20 |
| ES2151632T3 (es) | 2001-01-01 |
| CA2224764A1 (en) | 1998-06-16 |
| EP0848009A1 (de) | 1998-06-17 |
| JP4176845B2 (ja) | 2008-11-05 |
| SI0848009T1 (en) | 2000-12-31 |
| PT848009E (pt) | 2000-11-30 |
| DE69609845D1 (de) | 2000-09-21 |
| JPH10175991A (ja) | 1998-06-30 |
| DE69609845T2 (de) | 2000-12-21 |
| GR3034608T3 (en) | 2001-01-31 |
| US5874550A (en) | 1999-02-23 |
| EP0848009B1 (de) | 2000-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |