SU1011051A3 - Способ получени @ -гликозиловых производных антибиотиков из группы антрациклинов - Google Patents
Способ получени @ -гликозиловых производных антибиотиков из группы антрациклинов Download PDFInfo
- Publication number
- SU1011051A3 SU1011051A3 SU802949076A SU2949076A SU1011051A3 SU 1011051 A3 SU1011051 A3 SU 1011051A3 SU 802949076 A SU802949076 A SU 802949076A SU 2949076 A SU2949076 A SU 2949076A SU 1011051 A3 SU1011051 A3 SU 1011051A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- antibiotics
- antibiotic
- residue
- daunorubicin
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 4
- 229940088710 antibiotic agent Drugs 0.000 title abstract description 4
- 230000003115 biocidal effect Effects 0.000 claims abstract description 4
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 10
- 229960000975 daunorubicin Drugs 0.000 claims description 10
- 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 claims description 10
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 6
- 239000008103 glucose Substances 0.000 claims description 6
- 229940097043 glucuronic acid Drugs 0.000 claims description 6
- -1 glucuronic acid methyl ester Chemical class 0.000 claims description 6
- 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 claims description 5
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 4
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 4
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 4
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 3
- 229940009456 adriamycin Drugs 0.000 claims description 2
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 208000007976 Ketosis Diseases 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002584 ketoses Chemical class 0.000 abstract 1
- 150000002772 monosaccharides Chemical class 0.000 abstract 1
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 229920001542 oligosaccharide Polymers 0.000 abstract 1
- 150000002482 oligosaccharides Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1979219049A PL124284B1 (en) | 1979-10-17 | 1979-10-17 | Process for preparing n-glycosyl derivatives of antibiotics from anthracyclines group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1011051A3 true SU1011051A3 (ru) | 1983-04-07 |
Family
ID=19998972
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802949076A SU1011051A3 (ru) | 1979-10-17 | 1980-07-22 | Способ получени @ -гликозиловых производных антибиотиков из группы антрациклинов |
| SU802954187A SU1054352A1 (ru) | 1979-10-17 | 1980-07-30 | N-гликозиловые производные даунорубицина,про вл ющие антибиотическую активность |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802954187A SU1054352A1 (ru) | 1979-10-17 | 1980-07-30 | N-гликозиловые производные даунорубицина,про вл ющие антибиотическую активность |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4351937A (enExample) |
| JP (1) | JPS5914479B2 (enExample) |
| BE (1) | BE884318A (enExample) |
| DE (1) | DE3028148C2 (enExample) |
| DK (1) | DK305880A (enExample) |
| FI (1) | FI67708C (enExample) |
| FR (1) | FR2473524A1 (enExample) |
| GB (1) | GB2060609B (enExample) |
| PL (1) | PL124284B1 (enExample) |
| SE (1) | SE8005099L (enExample) |
| SU (2) | SU1011051A3 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH648327A5 (de) * | 1980-10-16 | 1985-03-15 | Hoffmann La Roche | Anthracycline. |
| JPS6297A (ja) * | 1985-06-24 | 1987-01-06 | Microbial Chem Res Found | アントラサイクリン化合物 |
| US4863739A (en) * | 1987-05-19 | 1989-09-05 | Board Of Regents, The University Of Texas System | Liposome compositions of anthracycline derivatives |
| WO1989006654A1 (en) * | 1988-01-19 | 1989-07-27 | Board Of Regents, The University Of Texas System | Glycosides, liposomal compositions thereof, and methods for their use |
| EP0648503B1 (en) * | 1993-09-22 | 2000-07-26 | Hoechst Aktiengesellschaft | Pro-prodrugs, their production and use |
| GB9727546D0 (en) * | 1997-12-31 | 1998-03-18 | Pharmacia & Upjohn Spa | Anthracycline glycosides |
| WO2000056267A2 (en) * | 1999-03-19 | 2000-09-28 | Waldemar Priebe | Methods and compositions for the manufacture of c-3' and c-4' anthracycline antibiotics |
| EP1278527A4 (en) | 2000-01-14 | 2003-04-09 | Intrabiotics Pharmaceuticals | DERIVATIVES OF POLYEN MACROLIDES, THEIR PRODUCTION AND USE |
| CN104211738B (zh) * | 2014-08-15 | 2016-09-28 | 合肥合源药业有限公司 | 一种伊达比星中的杂质、其制备方法及其应用 |
| RU2642068C1 (ru) * | 2017-04-26 | 2018-01-24 | Федеральное государственное бюджетное учреждение науки Институт элементоорганических соединений им. А.Н. Несмеянова Российской академии наук (ИНЭОС РАН) | N-пиперонильные производные даунорубицина, обладающие антипролиферативными свойствами |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI60877C (fi) * | 1971-08-13 | 1982-04-13 | Politechnika Gdanska | Foerfarande foer framstaellning av terapeutiskt aktiva i vatten laett dispergerbara polyenmakrolidantibiot-n-glykosylderivat |
| JPS5323961A (en) * | 1976-08-16 | 1978-03-06 | Microbial Chem Res Found | Antitumors |
| GB1561507A (en) * | 1976-11-17 | 1980-02-20 | Farmaceutici Italia | Snthracycline disaccharides |
| GB2007645B (en) * | 1977-10-17 | 1982-05-12 | Stanford Res Inst Int | Benzyl anthracyclines and pharmaceutical compositions containing them |
-
1979
- 1979-10-17 PL PL1979219049A patent/PL124284B1/pl unknown
-
1980
- 1980-07-11 SE SE8005099A patent/SE8005099L/xx not_active Application Discontinuation
- 1980-07-15 BE BE0/201411A patent/BE884318A/fr not_active IP Right Cessation
- 1980-07-15 DK DK305880A patent/DK305880A/da not_active Application Discontinuation
- 1980-07-18 GB GB8023586A patent/GB2060609B/en not_active Expired
- 1980-07-22 SU SU802949076A patent/SU1011051A3/ru active
- 1980-07-24 FI FI802332A patent/FI67708C/fi not_active IP Right Cessation
- 1980-07-24 DE DE3028148A patent/DE3028148C2/de not_active Expired
- 1980-07-25 US US06/172,262 patent/US4351937A/en not_active Expired - Lifetime
- 1980-07-30 SU SU802954187A patent/SU1054352A1/ru active
- 1980-08-26 JP JP55118220A patent/JPS5914479B2/ja not_active Expired
- 1980-09-08 FR FR8019344A patent/FR2473524A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2473524B1 (enExample) | 1983-06-03 |
| GB2060609A (en) | 1981-05-07 |
| JPS5914479B2 (ja) | 1984-04-04 |
| JPS5663994A (en) | 1981-05-30 |
| FI67708B (fi) | 1985-01-31 |
| SE8005099L (sv) | 1981-04-18 |
| FR2473524A1 (fr) | 1981-07-17 |
| DK305880A (da) | 1981-04-18 |
| PL219049A1 (enExample) | 1981-05-08 |
| SU1054352A1 (ru) | 1983-11-15 |
| PL124284B1 (en) | 1983-01-31 |
| DE3028148A1 (de) | 1981-04-30 |
| BE884318A (fr) | 1980-11-03 |
| US4351937A (en) | 1982-09-28 |
| DE3028148C2 (de) | 1984-10-25 |
| FI802332A7 (fi) | 1981-04-18 |
| FI67708C (fi) | 1985-05-10 |
| GB2060609B (en) | 1984-09-05 |
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