CN102757470B - 生产4-脱甲氧柔红霉素的方法 - Google Patents
生产4-脱甲氧柔红霉素的方法 Download PDFInfo
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- CN102757470B CN102757470B CN201210074569.3A CN201210074569A CN102757470B CN 102757470 B CN102757470 B CN 102757470B CN 201210074569 A CN201210074569 A CN 201210074569A CN 102757470 B CN102757470 B CN 102757470B
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- daunorubicin
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- demethylation
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- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 36
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- 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 24
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 22
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- GUGHGUXZJWAIAS-QQYBVWGSSA-N Daunorubicin hydrochloride Chemical compound Cl.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 GUGHGUXZJWAIAS-QQYBVWGSSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
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- 229960001904 epirubicin Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 229940073589 magnesium chloride anhydrous Drugs 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229960001221 pirarubicin Drugs 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000011476 stem cell transplantation Methods 0.000 description 1
- DGCFCIXSJPYNLX-UHFFFAOYSA-N trichloromethylsulfonyl trichloromethanesulfonate Chemical compound ClC(Cl)(Cl)S(=O)(=O)OS(=O)(=O)C(Cl)(Cl)Cl DGCFCIXSJPYNLX-UHFFFAOYSA-N 0.000 description 1
- PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/097,131 US8846882B2 (en) | 2011-04-29 | 2011-04-29 | Method of producing 4-demethoxydaunorubicin |
| US13/097,131 | 2011-04-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102757470A CN102757470A (zh) | 2012-10-31 |
| CN102757470B true CN102757470B (zh) | 2015-07-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210074569.3A Active CN102757470B (zh) | 2011-04-29 | 2012-03-20 | 生产4-脱甲氧柔红霉素的方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8846882B2 (enExample) |
| EP (1) | EP2518077B1 (enExample) |
| JP (1) | JP5524262B2 (enExample) |
| KR (1) | KR101563939B1 (enExample) |
| CN (1) | CN102757470B (enExample) |
| DK (1) | DK2518077T3 (enExample) |
| ES (1) | ES2562328T3 (enExample) |
| PL (1) | PL2518077T3 (enExample) |
| RU (1) | RU2540968C2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107698634B (zh) * | 2017-09-22 | 2020-03-10 | 南京正大天晴制药有限公司 | 一种盐酸伊达比星的制备方法 |
| CN107669693B (zh) * | 2017-09-22 | 2020-03-31 | 南京正大天晴制药有限公司 | 一种稳定安全的伊达比星药物组合物及其制备方法 |
| CN112010913B (zh) * | 2019-05-31 | 2022-06-21 | 南京正大天晴制药有限公司 | 4-脱氧柔红霉素的制备方法 |
| CN115785168B (zh) * | 2022-08-22 | 2023-11-07 | 浙江亚瑟医药有限公司 | 一种制备4-脱甲氧柔红霉素盐酸盐的方法 |
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| CN1037152A (zh) * | 1988-02-12 | 1989-11-15 | 法米塔利亚·卡洛·埃巴公司 | 4-脱甲氧基道诺霉素酮，即4-脱甲氧基道诺红菌素的糖苷配基的制备方法 |
| US5103029A (en) * | 1988-04-11 | 1992-04-07 | Farmitalia Carlo Erba S.R.L. | Process for preparing 4-demethoxydaunomycinone |
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| CN101909439A (zh) * | 2008-01-08 | 2010-12-08 | 苏洛克股份有限公司 | 蒽环化合物的4′-羟基的芳烷基化方法 |
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-
2011
- 2011-04-29 US US13/097,131 patent/US8846882B2/en not_active Expired - Fee Related
-
2012
- 2012-03-20 CN CN201210074569.3A patent/CN102757470B/zh active Active
- 2012-03-20 DK DK12160375.7T patent/DK2518077T3/en active
- 2012-03-20 PL PL12160375T patent/PL2518077T3/pl unknown
- 2012-03-20 EP EP12160375.7A patent/EP2518077B1/en active Active
- 2012-03-20 ES ES12160375.7T patent/ES2562328T3/es active Active
- 2012-03-20 RU RU2012110492/04A patent/RU2540968C2/ru active
- 2012-03-20 KR KR1020120028353A patent/KR101563939B1/ko active Active
- 2012-03-21 JP JP2012063036A patent/JP5524262B2/ja active Active
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| US4188377A (en) * | 1977-02-01 | 1980-02-12 | Farmitalia Carlo Erba S.P.A. | Carminomycin derivatives, their preparation and use |
| CN1037152A (zh) * | 1988-02-12 | 1989-11-15 | 法米塔利亚·卡洛·埃巴公司 | 4-脱甲氧基道诺霉素酮，即4-脱甲氧基道诺红菌素的糖苷配基的制备方法 |
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| US7053191B2 (en) * | 2003-05-21 | 2006-05-30 | Solux Corporation | Method of preparing 4-R-substituted 4-demethoxydaunorubicin |
| CN101331147A (zh) * | 2005-12-13 | 2008-12-24 | 苏洛克股份有限公司 | 用于制备4-脱甲基柔红霉素的方法 |
| CN101909439A (zh) * | 2008-01-08 | 2010-12-08 | 苏洛克股份有限公司 | 蒽环化合物的4′-羟基的芳烷基化方法 |
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Also Published As
| Publication number | Publication date |
|---|---|
| US8846882B2 (en) | 2014-09-30 |
| EP2518077B1 (en) | 2016-01-06 |
| RU2012110492A (ru) | 2013-09-27 |
| RU2540968C2 (ru) | 2015-02-10 |
| KR101563939B1 (ko) | 2015-10-29 |
| CN102757470A (zh) | 2012-10-31 |
| ES2562328T3 (es) | 2016-03-03 |
| DK2518077T3 (en) | 2016-01-18 |
| JP2012232971A (ja) | 2012-11-29 |
| KR20120122886A (ko) | 2012-11-07 |
| JP5524262B2 (ja) | 2014-06-18 |
| HK1178170A1 (en) | 2013-09-06 |
| PL2518077T3 (pl) | 2016-05-31 |
| EP2518077A1 (en) | 2012-10-31 |
| US20120277415A1 (en) | 2012-11-01 |
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