JP2012232971A5 - - Google Patents
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- Publication number
- JP2012232971A5 JP2012232971A5 JP2012063036A JP2012063036A JP2012232971A5 JP 2012232971 A5 JP2012232971 A5 JP 2012232971A5 JP 2012063036 A JP2012063036 A JP 2012063036A JP 2012063036 A JP2012063036 A JP 2012063036A JP 2012232971 A5 JP2012232971 A5 JP 2012232971A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- daunorubicin
- prot
- group
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 16
- 229960000975 daunorubicin Drugs 0.000 claims 13
- 238000000034 method Methods 0.000 claims 13
- 230000015572 biosynthetic process Effects 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 5
- 239000003153 chemical reaction reagent Substances 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 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 claims 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 4
- NAALWFYYHHJEFQ-ZASNTINBSA-N (2s,5r,6r)-6-[[(2r)-2-[[6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)C(C(N1)=O)=CC=C1C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 NAALWFYYHHJEFQ-ZASNTINBSA-N 0.000 claims 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000001540 azides Chemical class 0.000 claims 3
- 229960003109 daunorubicin hydrochloride Drugs 0.000 claims 3
- 229960000908 idarubicin Drugs 0.000 claims 3
- 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 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 2
- 229930188550 carminomycin Natural products 0.000 claims 2
- XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin 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=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 0.000 claims 2
- XREUEWVEMYWFFA-UHFFFAOYSA-N carminomycin I Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XREUEWVEMYWFFA-UHFFFAOYSA-N 0.000 claims 2
- 229950001725 carubicin Drugs 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 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 2
- 230000017858 demethylation Effects 0.000 claims 2
- 238000010520 demethylation reaction Methods 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 2
- NQPHMXWPDCSHTE-UHFFFAOYSA-N trifluoromethanesulfonyl azide Chemical compound FC(F)(F)S(=O)(=O)N=[N+]=[N-] NQPHMXWPDCSHTE-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
- 241001120493 Arene Species 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 230000001335 demethylating effect Effects 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- VOASREXNXKOKBP-WBKQXHNWSA-N CC(C(C(C1)NC(C(F)(F)F)=O)O)OC1O[C@@H](C[C@@](Cc1c(c(C(c2cccc(OC)c22)=O)c3C2=O)O)(C(C)=O)O)c1c3O Chemical compound CC(C(C(C1)NC(C(F)(F)F)=O)O)OC1O[C@@H](C[C@@](Cc1c(c(C(c2cccc(OC)c22)=O)c3C2=O)O)(C(C)=O)O)c1c3O VOASREXNXKOKBP-WBKQXHNWSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/097,131 | 2011-04-29 | ||
| US13/097,131 US8846882B2 (en) | 2011-04-29 | 2011-04-29 | Method of producing 4-demethoxydaunorubicin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012232971A JP2012232971A (ja) | 2012-11-29 |
| JP2012232971A5 true JP2012232971A5 (enExample) | 2013-12-26 |
| JP5524262B2 JP5524262B2 (ja) | 2014-06-18 |
Family
ID=45894256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012063036A Active JP5524262B2 (ja) | 2011-04-29 | 2012-03-21 | ４−デメトキシダウノルビシンを生成する方法 |
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 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012284A (en) | 1962-11-16 | 1977-03-15 | Societa' Farmaceutici Italia, S.p.A. | Process of preparation of antibiotic F.I. 1762 derivatives |
| GB1461190A (en) | 1974-09-20 | 1977-01-13 | Farmaceutici Italia | Anthracycline preparation |
| GB1551334A (en) | 1976-02-21 | 1979-08-30 | Newalls Insulation Co Ltd | Manufacture of insulation products |
| GB1509875A (en) * | 1976-06-14 | 1978-05-04 | Farmaceutici Italia | Optically active anthracyclinones and anthracycline glycosides |
| GB1555401A (en) | 1977-02-01 | 1979-11-07 | Farmaceutici Italia | Carminomycin derivatives |
| US4116981A (en) | 1977-05-02 | 1978-09-26 | Yuh-Geng Tsay | 5,12-epoxy-naphthacene-6,11-dione derivatives |
| US4161480A (en) | 1978-06-05 | 1979-07-17 | G. D. Searle & Co. | Intermediates for the synthesis of 4-demethoxydaunorubicin |
| IT1130074B (it) | 1979-04-20 | 1986-06-11 | Hoffmann La Roche | Composti policiclici e procedimento per la loro preparazione |
| US4471052A (en) | 1982-01-18 | 1984-09-11 | Adria Laboratories, Inc. | Biosynthesis of simplified anthracyclines |
| US5162512A (en) | 1982-03-09 | 1992-11-10 | Cytogen Corporation | Amine derivatives of anthracycline antibodies |
| US4448724A (en) | 1982-12-20 | 1984-05-15 | The Trustees Of The University Of Pennsylvania | Synthesis of 4-demethoxydaunomycinone |
| US4489206A (en) | 1983-05-13 | 1984-12-18 | Adria Laboratories, Inc. | Synthesis of (+)-4-demethoxydaunomycinone |
| 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 |
| US4697005A (en) | 1985-03-20 | 1987-09-29 | Ohio State University Research Foundation | 1-fluoro, 4-fluoro, and 1,4-difluoro anthracycline anticancer antibiotics |
| GB8708927D0 (en) | 1987-04-14 | 1987-05-20 | Erba Farmitalia | Chiral synthesis of anthracyclines |
| NZ224252A (en) | 1987-04-21 | 1991-09-25 | Erba Carlo Spa | An anthracycline glycoside and its preparation |
| 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 |
| GB8824947D0 (en) | 1988-10-25 | 1988-11-30 | Erba Carlo Spa | New 4-substituted anthracyclinones & process for preparing them |
| GB8904794D0 (en) | 1989-03-02 | 1989-04-12 | Erba Carlo Spa | Process for preparing anthracyclinones |
| MA21995A1 (fr) | 1989-11-13 | 1991-07-01 | Menarini Farma Ind | Nouvelles fluoronaphthacenediones,leurs derives glycozyles et leurs procedes de fabrication . |
| GB9019934D0 (en) | 1990-09-12 | 1990-10-24 | Erba Carlo Spa | 2-hydroxy-and 2-acyloxy-4-morpholinyl anthracyclines |
| US5776458A (en) | 1990-12-05 | 1998-07-07 | Pharmacia & Upjohn S.P.A. | Anthracycline-conjugates |
| GB9416007D0 (en) | 1994-08-08 | 1994-09-28 | Erba Carlo Spa | Anthracyclinone derivatives |
| IT1275953B1 (it) | 1995-03-22 | 1997-10-24 | Sicor Spa | Procedimento per la preparazione di antibiotici della classe delle antracicline |
| GB9516349D0 (en) | 1995-08-09 | 1995-10-11 | Pharmacia Spa | Aza-anthracyclinone derivatives |
| JP2000503639A (ja) | 1995-12-22 | 2000-03-28 | ブリストル―マイヤーズ スクイブ カンパニー | 分枝ヒドラゾンのリンカー類 |
| WO1997034612A1 (en) | 1996-03-22 | 1997-09-25 | Waldemar Priebe | Bis-anthracyclines with high activity against doxorubicin resistant tumors |
| US6218519B1 (en) | 1996-04-12 | 2001-04-17 | Pro-Neuron, Inc. | Compounds and methods for the selective treatment of cancer and bacterial infections |
| GB9701628D0 (en) | 1997-01-27 | 1997-03-19 | Pharmacia & Upjohn Spa | Imino-aza-anthracyclinone derivatives |
| AUPQ319799A0 (en) | 1999-10-01 | 1999-10-28 | Institute Of Drug Technology Australia Limited | Chemical methods |
| IT1318532B1 (it) | 2000-05-19 | 2003-08-27 | Antibioticos Spa | Procedimento di sintesi di derivati antraciclinici. |
| JP4688315B2 (ja) * | 2001-02-28 | 2011-05-25 | メルシャン株式会社 | ４−デメトキシダウノマイシノンの製造 |
| US7053191B2 (en) | 2003-05-21 | 2006-05-30 | Solux Corporation | Method of preparing 4-R-substituted 4-demethoxydaunorubicin |
| US9053181B2 (en) | 2003-11-03 | 2015-06-09 | James W. Wieder | Adaptive personalized playback or presentation using count |
| RU2260011C1 (ru) * | 2004-02-27 | 2005-09-10 | ОЛСУФЬЕВА Евгения Николаевна | Способ получения антибиотика карминомицина или его гидрохлорида |
| US7388083B2 (en) * | 2005-03-07 | 2008-06-17 | Solux Corporation | Epimerization of 4′-C bond and modification of 14-CH3-(CO)-fragment in anthracyclin antibiotics |
| US9035032B2 (en) * | 2005-12-13 | 2015-05-19 | Solux Corporation | Method for preparing 4-demethyldaunorubicin |
| KR20100029764A (ko) * | 2007-05-16 | 2010-03-17 | 케이티비 투머포슝스케쉘샤프트 엠비에이치 | 저점성 안트라사이클린 제제 |
| US8357785B2 (en) * | 2008-01-08 | 2013-01-22 | Solux Corporation | Method of aralkylation of 4′-hydroxyl group of anthracylins |
-
2011
- 2011-04-29 US US13/097,131 patent/US8846882B2/en not_active Expired - Fee Related
-
2012
- 2012-03-20 PL PL12160375T patent/PL2518077T3/pl unknown
- 2012-03-20 CN CN201210074569.3A patent/CN102757470B/zh active Active
- 2012-03-20 DK DK12160375.7T patent/DK2518077T3/en 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
- 2012-03-20 EP EP12160375.7A patent/EP2518077B1/en active Active
- 2012-03-21 JP JP2012063036A patent/JP5524262B2/ja active Active
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