SU645588A3 - Способ получени аналога дауномицина или его хлоргидрата - Google Patents
Способ получени аналога дауномицина или его хлоргидратаInfo
- Publication number
- SU645588A3 SU645588A3 SU752141338A SU2141338A SU645588A3 SU 645588 A3 SU645588 A3 SU 645588A3 SU 752141338 A SU752141338 A SU 752141338A SU 2141338 A SU2141338 A SU 2141338A SU 645588 A3 SU645588 A3 SU 645588A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- donosaminyl
- daunomycin
- chlorine
- hydrogen
- donosaminil
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 title claims description 3
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229940101209 mercuric oxide Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2608374A GB1467383A (en) | 1974-06-12 | 1974-06-12 | Daunomycin analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU645588A3 true SU645588A3 (ru) | 1979-01-30 |
Family
ID=10238087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752141338A SU645588A3 (ru) | 1974-06-12 | 1975-06-10 | Способ получени аналога дауномицина или его хлоргидрата |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4046878A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5840557B2 (cg-RX-API-DMAC7.html) |
| AT (1) | AT337363B (cg-RX-API-DMAC7.html) |
| BE (1) | BE830090A (cg-RX-API-DMAC7.html) |
| BG (1) | BG61059B2 (cg-RX-API-DMAC7.html) |
| CH (1) | CH611317A5 (cg-RX-API-DMAC7.html) |
| DE (2) | DE19375027I2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK147304C (cg-RX-API-DMAC7.html) |
| ES (1) | ES438431A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2274629A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1467383A (cg-RX-API-DMAC7.html) |
| HK (1) | HK982A (cg-RX-API-DMAC7.html) |
| MY (1) | MY103666A (cg-RX-API-DMAC7.html) |
| NL (1) | NL173272C (cg-RX-API-DMAC7.html) |
| SE (1) | SE423633B (cg-RX-API-DMAC7.html) |
| SU (1) | SU645588A3 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA753722B (cg-RX-API-DMAC7.html) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1506200A (en) * | 1975-04-30 | 1978-04-05 | Farmaceutici Italia | Glycosides |
| GB1509875A (en) * | 1976-06-14 | 1978-05-04 | Farmaceutici Italia | Optically active anthracyclinones and anthracycline glycosides |
| US4161480A (en) * | 1978-06-05 | 1979-07-17 | G. D. Searle & Co. | Intermediates for the synthesis of 4-demethoxydaunorubicin |
| 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 |
| IL55431A (en) * | 1978-08-24 | 1982-07-30 | Yeda Res & Dev | Anthracycline type antibiotics,their preparation and pharmaceutical compositions comprising them |
| NL8001417A (nl) * | 1979-03-17 | 1980-09-19 | Erba Farmitalia | Antitumorglycosiden. |
| JPS5673039A (en) * | 1979-08-20 | 1981-06-17 | Hoffmann La Roche | Naphthacene derivative |
| ATE1101T1 (de) * | 1979-09-01 | 1982-06-15 | Farmitalia Carlo Erba S.P.A. | Anthracyclin-glycoside, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzung. |
| DE3100968A1 (de) * | 1980-01-16 | 1982-01-14 | Farmitalia Carlo Erba S.p.A., 20159 Milano | Anthracyclinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4348388A (en) * | 1980-04-02 | 1982-09-07 | G.D. Searle & Co. | 11-Amino-11-deoxydaunorubicin and analogs |
| ZA814722B (en) * | 1980-07-18 | 1982-07-28 | Hoffmann La Roche | Novel anthracycline glycosides |
| IT1210476B (it) * | 1981-05-28 | 1989-09-14 | Erba Farmitalia | Antracicline. |
| GB8317037D0 (en) * | 1983-06-23 | 1983-07-27 | Erba Farmitalia | 6-deoxyanthracyclines |
| US5138042A (en) * | 1981-05-28 | 1992-08-11 | Farmitalia Carlo Erba S.P.A. | 6-deoxyanthracyclines |
| US4563444A (en) * | 1982-05-26 | 1986-01-07 | Farmitalia Carlo Erba S.P.A. | Anthracycline glycosides, use and compositions containing same |
| US4604381A (en) * | 1982-07-16 | 1986-08-05 | Farmitalia Carlo Erba S.P.A. | 4-demethoxy-13-dihydrodaunorubicin and use thereof |
| US4562177A (en) * | 1982-08-17 | 1985-12-31 | The Ohio State University Research Foundation | 3'-Amino-2' halo-anthracycline antibiotics |
| US4564674A (en) * | 1983-10-31 | 1986-01-14 | Sagami Chemical Research Center | Process for an anthracycline derivative, and an anthracyclinone derivative useful for the process |
| US4496485A (en) * | 1983-11-25 | 1985-01-29 | G. D. Searle & Co. | Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones |
| US4537882A (en) * | 1984-05-10 | 1985-08-27 | Ohio State University | 4-Demethoxy-3'-desamino-2'-halo-anthracycline and pharmaceutical composition containing same |
| US4697005A (en) * | 1985-03-20 | 1987-09-29 | Ohio State University Research Foundation | 1-fluoro, 4-fluoro, and 1,4-difluoro anthracycline anticancer antibiotics |
| US5124317A (en) * | 1985-08-02 | 1992-06-23 | Farmitalia Carlo Erba S.P.A. | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| NZ224252A (en) * | 1987-04-21 | 1991-09-25 | Erba Carlo Spa | An anthracycline glycoside and its preparation |
| JPS63191263U (cg-RX-API-DMAC7.html) * | 1987-05-29 | 1988-12-09 | ||
| GB2212154B (en) * | 1987-11-10 | 1991-03-27 | Erba Carlo Spa | New 4-demethoxy anthracycline derivatives |
| GB8803301D0 (en) * | 1988-02-12 | 1988-03-09 | Erba Carlo Spa | Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin |
| GB8808475D0 (en) * | 1988-04-11 | 1988-05-11 | Erba Carlo Spa | Process for preparing 4-demethoxydauno-mycinone |
| GB8818167D0 (en) * | 1988-07-29 | 1988-09-01 | Erba Carlo Spa | Novel 4-substituted anthracyclinones & process for their preparation |
| JP2563080B2 (ja) * | 1992-03-02 | 1996-12-11 | フアイザー・インコーポレイテツド | マクロライドの糖誘導体 |
| AU2003299378A1 (en) * | 2002-10-11 | 2004-05-04 | Board Of Regents, The University Of Texas System | Method and compounds for inhibiting hec1 activity for the treatment of proliferative diseases |
| CN101146532B (zh) | 2005-01-21 | 2012-05-09 | 阿斯泰克斯治疗有限公司 | 药物化合物 |
| JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| BRPI0923815A2 (pt) * | 2008-12-23 | 2015-07-14 | Pharmasset Inc | Síntese de nucleosídeos de purina |
| EP2376514A2 (en) * | 2008-12-23 | 2011-10-19 | Pharmasset, Inc. | Nucleoside analogs |
| EA019341B1 (ru) * | 2008-12-23 | 2014-02-28 | Джилид Фармассет, Ллс. | Фосфорамидаты нуклеозидов |
| PL2719708T3 (pl) | 2009-11-13 | 2018-04-30 | Daiichi Sankyo Europe Gmbh | Materiał i sposoby leczenia lub zapobiegania chorobom związanym z HER-3 |
| LT2609923T (lt) | 2010-03-31 | 2017-09-11 | Gilead Pharmasset Llc | (s)-izopropilo 2-(((s)-(perfluorfenoksi)(fenoksi)fosforil)amino)-propanoato kristalinimo būdas |
| WO2012018404A2 (en) | 2010-08-06 | 2012-02-09 | U3 Pharma Gmbh | Use of her3 binding agents in prostate treatment |
| DE102011113652A1 (de) | 2011-09-19 | 2013-03-21 | Heraeus Precious Metals Gmbh & Co. Kg | Kristallisierung von Idarubicinhydrochlorid |
| DK3311827T3 (da) | 2011-10-03 | 2023-04-03 | Canqura Oncology Ab | Nanopartikler, fremgangsmåde til fremstilling og anvendelse deraf som bærere for amfipatiske eller hydrofobe molekyler inden for det medicinske område, inklusiv cancerbehandling, samt fødevarerelaterede forbindelser |
| US9907846B2 (en) | 2013-04-01 | 2018-03-06 | Mx Adjuvac Ab | Nanoparticles, composed of sterol and saponin from Quillaja saponaria Molina for use in pharmaceutical compositions |
| EP3669890A1 (en) | 2018-12-18 | 2020-06-24 | Croda International PLC | Filamentous nanoparticles having vaccine adjuvant effect |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427300A (en) * | 1965-11-12 | 1969-02-11 | Merck & Co Inc | Anti-inflammatory steroid 2'-acetamido-2'-deoxy-glucoside compounds |
| US3803124A (en) * | 1968-04-12 | 1974-04-09 | Farmaceutici It Soc | Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives |
| US3686163A (en) * | 1968-05-14 | 1972-08-22 | Farmaceutici Italia | Dihydrodaunomycin antibiotic and derivatives thereof |
-
1974
- 1974-06-12 GB GB2608374A patent/GB1467383A/en not_active Expired
-
1975
- 1975-05-22 US US05/579,901 patent/US4046878A/en not_active Expired - Lifetime
- 1975-06-06 NL NLAANVRAGE7506745,A patent/NL173272C/xx not_active IP Right Cessation
- 1975-06-09 DE DE1993175027 patent/DE19375027I2/de active Active
- 1975-06-09 DK DK256875A patent/DK147304C/da not_active IP Right Cessation
- 1975-06-09 SE SE7506589A patent/SE423633B/xx not_active IP Right Cessation
- 1975-06-09 AT AT437375A patent/AT337363B/de not_active IP Right Cessation
- 1975-06-09 DE DE19752525633 patent/DE2525633A1/de active Granted
- 1975-06-09 FR FR7517881A patent/FR2274629A1/fr active Granted
- 1975-06-10 SU SU752141338A patent/SU645588A3/ru active
- 1975-06-10 ZA ZA00753722A patent/ZA753722B/xx unknown
- 1975-06-10 JP JP50069250A patent/JPS5840557B2/ja not_active Expired
- 1975-06-11 ES ES438431A patent/ES438431A1/es not_active Expired
- 1975-06-11 BE BE157205A patent/BE830090A/xx not_active IP Right Cessation
- 1975-06-11 CH CH756375A patent/CH611317A5/xx not_active IP Right Cessation
-
1982
- 1982-01-14 HK HK9/82A patent/HK982A/xx unknown
-
1988
- 1988-12-22 MY MYPI88001506A patent/MY103666A/en unknown
-
1993
- 1993-11-11 BG BG098211A patent/BG61059B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS518260A (cg-RX-API-DMAC7.html) | 1976-01-23 |
| JPS5840557B2 (ja) | 1983-09-06 |
| SE423633B (sv) | 1982-05-17 |
| AT337363B (de) | 1977-06-27 |
| DK147304B (da) | 1984-06-12 |
| DE2525633A1 (de) | 1976-01-02 |
| NL173272B (nl) | 1983-08-01 |
| BG61059B2 (bg) | 1996-09-30 |
| CH611317A5 (cg-RX-API-DMAC7.html) | 1979-05-31 |
| SE7506589L (sv) | 1975-12-15 |
| ATA437375A (de) | 1976-10-15 |
| GB1467383A (en) | 1977-03-16 |
| ES438431A1 (es) | 1977-02-01 |
| HK982A (en) | 1982-01-22 |
| DE19375027I2 (de) | 2002-06-13 |
| NL173272C (nl) | 1984-01-02 |
| AU8197975A (en) | 1976-12-16 |
| US4046878A (en) | 1977-09-06 |
| ZA753722B (en) | 1976-09-29 |
| BE830090A (fr) | 1975-12-11 |
| FR2274629B1 (cg-RX-API-DMAC7.html) | 1980-01-11 |
| DK256875A (da) | 1975-12-13 |
| DE2525633B2 (cg-RX-API-DMAC7.html) | 1979-03-01 |
| DE2525633C3 (cg-RX-API-DMAC7.html) | 1979-10-18 |
| NL7506745A (nl) | 1975-12-16 |
| FR2274629A1 (fr) | 1976-01-09 |
| DK147304C (da) | 1984-12-17 |
| MY103666A (en) | 1993-08-28 |
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