CS243500B2 - Method of antracyclinglycocides production - Google Patents
Method of antracyclinglycocides production Download PDFInfo
- Publication number
- CS243500B2 CS243500B2 CS841254A CS125485A CS243500B2 CS 243500 B2 CS243500 B2 CS 243500B2 CS 841254 A CS841254 A CS 841254A CS 125485 A CS125485 A CS 125485A CS 243500 B2 CS243500 B2 CS 243500B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen atom
- hydrogen
- protected
- formula
- glycosides
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229930182470 glycoside Natural products 0.000 claims description 9
- 150000002338 glycosides Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000008135 α-glycosides Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004280 Sodium formate Substances 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 3
- 235000019254 sodium formate Nutrition 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229940045799 anthracyclines and related substance Drugs 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical class 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 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838317037A GB8317037D0 (en) | 1983-06-23 | 1983-06-23 | 6-deoxyanthracyclines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS243500B2 true CS243500B2 (en) | 1986-06-12 |
Family
ID=10544662
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS841254A CS243500B2 (en) | 1983-06-23 | 1984-06-21 | Method of antracyclinglycocides production |
| CS844740A CS243490B2 (en) | 1983-06-23 | 1984-06-21 | Method of l-deoxyanthracyclinones production |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS844740A CS243490B2 (en) | 1983-06-23 | 1984-06-21 | Method of l-deoxyanthracyclinones production |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4939282A (en, 2012) |
| JP (2) | JPS6013735A (en, 2012) |
| AT (1) | AT390252B (en, 2012) |
| AU (2) | AU561456B2 (en, 2012) |
| BE (1) | BE899963A (en, 2012) |
| CA (1) | CA1234104A (en, 2012) |
| CH (2) | CH665422A5 (en, 2012) |
| CS (2) | CS243500B2 (en, 2012) |
| DK (2) | DK306484A (en, 2012) |
| FI (1) | FI842505A7 (en, 2012) |
| FR (1) | FR2549046B1 (en, 2012) |
| GB (1) | GB8317037D0 (en, 2012) |
| GR (1) | GR82130B (en, 2012) |
| HU (2) | HU194902B (en, 2012) |
| IL (1) | IL72168A (en, 2012) |
| IT (1) | IT1212101B (en, 2012) |
| NL (1) | NL8401957A (en, 2012) |
| SE (2) | SE8403353L (en, 2012) |
| SU (2) | SU1561821A3 (en, 2012) |
| ZA (1) | ZA844719B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8317037D0 (en) * | 1983-06-23 | 1983-07-27 | Erba Farmitalia | 6-deoxyanthracyclines |
| GB2182926B (en) * | 1985-11-19 | 1989-10-04 | Erba Farmitalia | Nitro anthracyclines, process for their preparation and use thereof |
| GB8803301D0 (en) * | 1988-02-12 | 1988-03-09 | Erba Carlo Spa | Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin |
| IT1275953B1 (it) * | 1995-03-22 | 1997-10-24 | Sicor Spa | Procedimento per la preparazione di antibiotici della classe delle antracicline |
| US5948896A (en) * | 1997-08-13 | 1999-09-07 | Gem Pharmaceuticals | Processes for preparing 13-deoxy anthracycline derivatives |
| US5942605A (en) * | 1998-03-03 | 1999-08-24 | Gem Pharmaceuticals, Inc. | 5-imino-13-deoxy anthracycline derivatives, their uses, and processes for preparing them |
| JP4455643B2 (ja) | 2007-10-30 | 2010-04-21 | 東洋エンジニアリング株式会社 | 造粒装置及びそれを用いる造粒方法 |
Family Cites Families (14)
| 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 |
| GB1467383A (en) * | 1974-06-12 | 1977-03-16 | Farmaceutici Italia | Daunomycin analogues |
| GB1509875A (en) * | 1976-06-14 | 1978-05-04 | Farmaceutici Italia | Optically active anthracyclinones and anthracycline glycosides |
| GB1567456A (en) * | 1976-11-16 | 1980-05-14 | Farmaceutici Italia | Daunomycin derivatives |
| GB1573036A (en) * | 1977-05-05 | 1980-08-13 | Farmaceutici Italia | Anthracyclines |
| GB1573037A (en) * | 1977-05-05 | 1980-08-13 | Farmaceutici Italia | Anthracyclines |
| GB1567457A (en) * | 1977-11-11 | 1980-05-14 | Farmaceutici Italia | Daunomycinone derivatives |
| US4370476A (en) * | 1979-07-17 | 1983-01-25 | Usher Thomas C | Dextran polycarboxylic acids, ferric hydroxide complexes |
| US4348388A (en) * | 1980-04-02 | 1982-09-07 | G.D. Searle & Co. | 11-Amino-11-deoxydaunorubicin and analogs |
| US4374979A (en) * | 1981-04-27 | 1983-02-22 | The University Of Kansas Endowment Association | Regiospecific synthesis of anthracyclinone compounds such as daunomycinone |
| GB8317037D0 (en) * | 1983-06-23 | 1983-07-27 | Erba Farmitalia | 6-deoxyanthracyclines |
| IT1210476B (it) * | 1981-05-28 | 1989-09-14 | Erba Farmitalia | Antracicline. |
| EP0087807B1 (en) * | 1982-03-02 | 1985-11-27 | Sumitomo Chemical Company, Limited | Preparation of optically active 4-demethoxydaunomycinone |
| BE896743A (fr) * | 1982-08-13 | 1983-09-16 | Erba Farmitalia | Synthese de naphtacenequinone. |
-
1983
- 1983-06-23 GB GB838317037A patent/GB8317037D0/en active Pending
-
1984
- 1984-06-19 US US06/622,177 patent/US4939282A/en not_active Expired - Fee Related
- 1984-06-19 AT AT0199684A patent/AT390252B/de not_active IP Right Cessation
- 1984-06-19 AU AU29524/84A patent/AU561456B2/en not_active Ceased
- 1984-06-20 FR FR8409680A patent/FR2549046B1/fr not_active Expired
- 1984-06-20 BE BE0/213174A patent/BE899963A/fr not_active IP Right Cessation
- 1984-06-20 FI FI842505A patent/FI842505A7/fi not_active Application Discontinuation
- 1984-06-20 NL NL8401957A patent/NL8401957A/xx not_active Application Discontinuation
- 1984-06-20 GR GR75063A patent/GR82130B/el unknown
- 1984-06-20 IL IL72168A patent/IL72168A/xx unknown
- 1984-06-21 CH CH3510/86A patent/CH665422A5/it not_active IP Right Cessation
- 1984-06-21 JP JP59126567A patent/JPS6013735A/ja active Granted
- 1984-06-21 SE SE8403353A patent/SE8403353L/xx not_active Application Discontinuation
- 1984-06-21 CS CS841254A patent/CS243500B2/cs unknown
- 1984-06-21 CS CS844740A patent/CS243490B2/cs unknown
- 1984-06-21 SU SU843753950A patent/SU1561821A3/ru active
- 1984-06-21 CH CH3007/84A patent/CH661922A5/it not_active IP Right Cessation
- 1984-06-21 ZA ZA844719A patent/ZA844719B/xx unknown
- 1984-06-21 IT IT8421522A patent/IT1212101B/it active
- 1984-06-22 HU HU842436A patent/HU194902B/hu not_active IP Right Cessation
- 1984-06-22 CA CA000457254A patent/CA1234104A/en not_active Expired
- 1984-06-22 HU HU843650A patent/HU196821B/hu not_active IP Right Cessation
- 1984-06-22 DK DK306484A patent/DK306484A/da not_active Application Discontinuation
- 1984-12-13 SU SU843823254A patent/SU1429935A3/ru active
-
1987
- 1987-02-11 AU AU68818/87A patent/AU574599B2/en not_active Ceased
-
1989
- 1989-05-02 SE SE8901572A patent/SE8901572D0/xx not_active Application Discontinuation
-
1990
- 1990-02-13 DK DK037890A patent/DK37890D0/da not_active Application Discontinuation
- 1990-03-28 US US07/501,869 patent/US5037970A/en not_active Expired - Fee Related
-
1992
- 1992-08-19 JP JP4220019A patent/JPH0735392B2/ja not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2651414B2 (ja) | ４−デメントキシ−４−アミノ−アントラサイクリン類 | |
| SU728719A3 (ru) | Способ получени гликозидов антрациклина | |
| US5945518A (en) | Process for the preparation of anthracycline antibiotics | |
| CS243500B2 (en) | Method of antracyclinglycocides production | |
| IE53120B1 (en) | Anthracyclines | |
| KR950004897B1 (ko) | 안트라사이클린 글리코사이드 유도체의 제조방법 | |
| CS202570B2 (en) | Process for preparing aminoglycsidic antibiotics | |
| EP0254484B1 (en) | 6-amino anthracyclines, process for their preparation and use thereof | |
| EP0199920B1 (en) | New antitumor anthracyclines | |
| EP0063776A1 (en) | Novel anthracyclinone glycosides and their preparation method | |
| US4199571A (en) | Substituted anthracyclines, their preparation and use | |
| HU221969B1 (hu) | Eljárás etopozid foszfát és etopozid előállítására | |
| RU2073681C1 (ru) | Антрациклиновый гликозид и способы его получения | |
| JPS6134437B2 (en, 2012) | ||
| EP0475071B1 (en) | 2-acyloxy-4-morpholinyl anthracycline | |
| CS270411B2 (en) | Method of new 4 halogen anthracycline glycosides production | |
| US4496485A (en) | Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones | |
| JPH0778073B2 (ja) | ニトロアントラサイクリン、その製造方法およびその使用 | |
| CS196212B2 (en) | Process for preparing anthracyclines | |
| NL8802721A (nl) | Nieuwe 4-demethoxy antracyclinederivaten. | |
| GB2174387A (en) | 6-Deoxyanthracycline glycosides | |
| SK131092A3 (en) | Method of production of 4-demethylepipodophylotoxinglucoside- -4-phosphates | |
| FI89496B (fi) | Foerfarande foer framstaellning av 4-demetoxi-4-aminoantracykliner | |
| PL182601B1 (pl) | Sposób otrzymywania antybiotyków antracyklinowych | |
| CS235540B2 (cs) | Způsob výroby nových derivátů glykosidů anthracyklinu |