SU886748A3 - Способ получени антрациклиновых гликозидов - Google Patents
Способ получени антрациклиновых гликозидов Download PDFInfo
- Publication number
- SU886748A3 SU886748A3 SU772439103A SU2439103A SU886748A3 SU 886748 A3 SU886748 A3 SU 886748A3 SU 772439103 A SU772439103 A SU 772439103A SU 2439103 A SU2439103 A SU 2439103A SU 886748 A3 SU886748 A3 SU 886748A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- metal
- derivatives
- glycosides
- glycoside
- parent
- Prior art date
Links
- 229930182470 glycoside Natural products 0.000 title claims abstract description 20
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 17
- 239000002184 metal Substances 0.000 claims abstract description 41
- 229910052751 metal Inorganic materials 0.000 claims abstract description 41
- 150000001768 cations Chemical class 0.000 claims abstract description 11
- 229940045799 anthracyclines and related substance Drugs 0.000 claims abstract description 8
- 239000003446 ligand Substances 0.000 claims abstract description 7
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 230000003285 pharmacodynamic effect Effects 0.000 claims description 2
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 claims 1
- 239000007998 bicine buffer Substances 0.000 claims 1
- 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 abstract description 36
- 229960004679 doxorubicin Drugs 0.000 abstract description 19
- 241000699670 Mus sp. Species 0.000 abstract description 7
- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 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 description 3
- 230000009920 chelation Effects 0.000 abstract description 3
- 229960000975 daunorubicin Drugs 0.000 abstract description 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 abstract description 3
- 231100000419 toxicity Toxicity 0.000 abstract description 3
- 230000001988 toxicity Effects 0.000 abstract description 3
- 206010048610 Cardiotoxicity Diseases 0.000 abstract description 2
- 231100000259 cardiotoxicity Toxicity 0.000 abstract description 2
- 241000699666 Mus <mouse, genus> Species 0.000 abstract 1
- 230000000118 anti-neoplastic effect Effects 0.000 abstract 1
- 230000001079 digestive effect Effects 0.000 abstract 1
- 230000003292 diminished effect Effects 0.000 abstract 1
- 230000002489 hematologic effect Effects 0.000 abstract 1
- 231100001274 therapeutic index Toxicity 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 15
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 5
- 239000013522 chelant Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 239000010949 copper Substances 0.000 description 4
- 230000006820 DNA synthesis Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910001447 ferric ion Inorganic materials 0.000 description 1
- 231100000226 haematotoxicity Toxicity 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000004313 potentiometry Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES444380A ES444380A1 (es) | 1976-01-16 | 1976-01-16 | Un procedimiento para preparar derivados metalicos antraci- clinicos. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU886748A3 true SU886748A3 (ru) | 1981-11-30 |
Family
ID=8470743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772439103A SU886748A3 (ru) | 1976-01-16 | 1977-01-14 | Способ получени антрациклиновых гликозидов |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4138480A (enExample) |
| JP (1) | JPS52111555A (enExample) |
| AR (1) | AR218620A1 (enExample) |
| AT (1) | AT349634B (enExample) |
| AU (1) | AU513698B2 (enExample) |
| BE (1) | BE850438A (enExample) |
| CA (1) | CA1070680A (enExample) |
| CH (1) | CH629219A5 (enExample) |
| DD (1) | DD129452A5 (enExample) |
| DE (1) | DE2701405C2 (enExample) |
| DK (1) | DK11877A (enExample) |
| EG (1) | EG12735A (enExample) |
| ES (1) | ES444380A1 (enExample) |
| FI (1) | FI770115A7 (enExample) |
| FR (1) | FR2338285A1 (enExample) |
| GB (1) | GB1568263A (enExample) |
| GR (1) | GR70696B (enExample) |
| HU (1) | HU177832B (enExample) |
| IE (1) | IE44689B1 (enExample) |
| IL (1) | IL51264A (enExample) |
| NL (1) | NL7700379A (enExample) |
| NO (1) | NO770122L (enExample) |
| NZ (1) | NZ183084A (enExample) |
| PH (1) | PH16582A (enExample) |
| PL (1) | PL108660B1 (enExample) |
| PT (1) | PT66067B (enExample) |
| SE (1) | SE7700398L (enExample) |
| SU (1) | SU886748A3 (enExample) |
| YU (1) | YU5477A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2336277C2 (ru) * | 2003-05-21 | 2008-10-20 | Солакс Корпорейшн | Способ получения 4-r-замещенного 4-деметоксидаунорубицина |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2959798A (en) * | 1958-03-24 | 1960-11-15 | Champlin Oil & Refining Co | Pipe line cleaner |
| US4337335A (en) * | 1978-05-18 | 1982-06-29 | Schering Corporation | Transition metal salt complexes of polyamino organic compounds |
| IT1184161B (it) * | 1985-03-14 | 1987-10-22 | Franco Conti | Derivati del chitosano costituiti da complessi di coordinazione con ioni ferrosi |
| JPS63310830A (ja) * | 1987-06-10 | 1988-12-19 | Meiji Seika Kaisha Ltd | 抗レトロウイルス剤 |
| GB9613182D0 (en) * | 1996-06-24 | 1996-08-28 | Nycomed Imaging As | Method |
| NL1009226C2 (nl) * | 1998-05-20 | 1999-11-24 | Faculteit Geneeskunde Universi | Toepassing van een nucleïnezuur-bindend chemotherapeutisch agens, een farmaceutisch preparaat en een geneesmiddelcombinatie. |
| US20060198882A1 (en) * | 2003-03-21 | 2006-09-07 | Yechezkel Barenholz | Stable liposomes or micelles comprising a sphinolipid and a peg-lipopolymer |
| US20080058274A1 (en) * | 2004-11-15 | 2008-03-06 | Yechezkel Barenholz | Combination Therapy |
| US20100087370A1 (en) * | 2007-02-14 | 2010-04-08 | The General Hospital Corporation | Modulation of nitric oxide signaling to normalize tumor vasculature |
| DK2582847T3 (en) | 2010-06-18 | 2016-12-19 | Myriad Genetics Inc | METHODS AND MATERIALS TO ASSESS loss of heterozygosity |
| WO2012027224A1 (en) | 2010-08-24 | 2012-03-01 | Dana-Farber Cancer Institute, Inc. | Methods for predicting anti-cancer response |
| EP4563709A3 (en) | 2011-06-17 | 2025-09-03 | Myriad Genetics, Inc. | Methods and materials for assessing allelic imbalance |
| EP2794907B2 (en) | 2011-12-21 | 2022-11-23 | Myriad Genetics, Inc. | Methods and materials for assessing loss of heterozygosity |
| CA2864481C (en) | 2012-02-23 | 2020-07-14 | Dana-Farber Cancer Institute, Inc. | Methods for predicting anti-cancer response |
| WO2013182645A1 (en) | 2012-06-07 | 2013-12-12 | Institut Curie | Methods for detecting inactivation of the homologous recombination pathway (brca1/2) in human tumors |
| US10308986B2 (en) | 2013-03-14 | 2019-06-04 | Children's Medical Center Corporation | Cancer diagnosis, treatment selection and treatment |
| EP3693475A1 (en) | 2013-04-05 | 2020-08-12 | Myriad Genetics, Inc. | Methods and materials for assessing homologous recombination deficiency |
| CA2931181C (en) | 2013-12-09 | 2023-01-24 | Institut Curie | Methods for detecting inactivation of the homologous recombination pathway (brca1/2) in human tumors |
| JP6877334B2 (ja) | 2014-08-15 | 2021-05-26 | ミリアド・ジェネティックス・インコーポレイテッド | 相同組換え欠損を評価するための方法および材料 |
| EP4141127B1 (en) | 2021-08-30 | 2024-10-09 | Zentrum Familiärer Brust- und Eierstockkrebs Universitätsklinik Köln | Method for assessing homologous recombination deficiency in ovarian cancer cells |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3074927A (en) * | 1960-04-12 | 1963-01-22 | Paul D Saltman | Metallic complexes of reducing sugars |
| YU33730B (en) * | 1967-04-18 | 1978-02-28 | Farmaceutici Italia | Process for preparing a novel antibiotic substance and salts thereof |
| GB1469430A (en) * | 1974-12-24 | 1977-04-06 | Farmaceutici Italia | Daunomycin derivatives |
-
1976
- 1976-01-16 ES ES444380A patent/ES444380A1/es not_active Expired
-
1977
- 1977-01-08 EG EG12/77A patent/EG12735A/xx active
- 1977-01-11 US US05/758,446 patent/US4138480A/en not_active Expired - Lifetime
- 1977-01-11 HU HU77GO1361A patent/HU177832B/hu unknown
- 1977-01-12 AR AR266173A patent/AR218620A1/es active
- 1977-01-13 PT PT66067A patent/PT66067B/pt unknown
- 1977-01-13 DK DK11877A patent/DK11877A/da not_active Application Discontinuation
- 1977-01-13 AU AU21319/77A patent/AU513698B2/en not_active Expired
- 1977-01-14 NZ NZ183084A patent/NZ183084A/xx unknown
- 1977-01-14 FI FI770115A patent/FI770115A7/fi not_active Application Discontinuation
- 1977-01-14 SU SU772439103A patent/SU886748A3/ru active
- 1977-01-14 DE DE2701405A patent/DE2701405C2/de not_active Expired
- 1977-01-14 CH CH48477A patent/CH629219A5/de not_active IP Right Cessation
- 1977-01-14 JP JP252277A patent/JPS52111555A/ja active Granted
- 1977-01-14 AT AT19677A patent/AT349634B/de not_active IP Right Cessation
- 1977-01-14 NO NO770122A patent/NO770122L/no unknown
- 1977-01-14 IL IL51264A patent/IL51264A/xx unknown
- 1977-01-14 PH PH19347A patent/PH16582A/en unknown
- 1977-01-14 CA CA269,807A patent/CA1070680A/en not_active Expired
- 1977-01-14 FR FR7701034A patent/FR2338285A1/fr active Granted
- 1977-01-14 SE SE7700398A patent/SE7700398L/xx unknown
- 1977-01-14 NL NL7700379A patent/NL7700379A/xx not_active Application Discontinuation
- 1977-01-15 PL PL1977195344A patent/PL108660B1/pl not_active IP Right Cessation
- 1977-01-15 GR GR52580A patent/GR70696B/el unknown
- 1977-01-17 GB GB2367/77A patent/GB1568263A/en not_active Expired
- 1977-01-17 DD DD7700196969A patent/DD129452A5/xx unknown
- 1977-01-17 IE IE87/77A patent/IE44689B1/en unknown
- 1977-01-17 BE BE174119A patent/BE850438A/xx not_active IP Right Cessation
- 1977-03-21 YU YU00054/77A patent/YU5477A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2336277C2 (ru) * | 2003-05-21 | 2008-10-20 | Солакс Корпорейшн | Способ получения 4-r-замещенного 4-деметоксидаунорубицина |
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