WO2005021565A1 - Method of preparing 4-r-substituted 4-demethoxydaunorubicin - Google Patents
Method of preparing 4-r-substituted 4-demethoxydaunorubicin Download PDFInfo
- Publication number
- WO2005021565A1 WO2005021565A1 PCT/US2004/016739 US2004016739W WO2005021565A1 WO 2005021565 A1 WO2005021565 A1 WO 2005021565A1 US 2004016739 W US2004016739 W US 2004016739W WO 2005021565 A1 WO2005021565 A1 WO 2005021565A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- demethyldaunorubicin
- acyl
- alkyl
- Prior art date
Links
- 0 CC(C(*)C(*C1=CC=*1O)C1)OC1O[C@@](C[C@@](Cc1c(c(C(c2cccc(OS(C)(=O)=O)c22)=O)c3C2=O)O)(C(C)=O)O)c1c3O Chemical compound CC(C(*)C(*C1=CC=*1O)C1)OC1O[C@@](C[C@@](Cc1c(c(C(c2cccc(OS(C)(=O)=O)c22)=O)c3C2=O)O)(C(C)=O)O)c1c3O 0.000 description 2
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE04801954T DE04801954T1 (en) | 2003-05-21 | 2004-05-20 | PROCESS FOR PREPARING 4-R-SUBSTITUTED 4-DEMETHOXYDAUNORUBICIN |
EP04801954.1A EP1625136B1 (en) | 2003-05-21 | 2004-05-20 | Method of preparing 4-r-substituted 4-demethoxydaunorubicin |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US47219203P | 2003-05-21 | 2003-05-21 | |
US60/472,192 | 2003-05-21 | ||
US10/831,448 | 2004-04-23 | ||
US10/831,448 US7053191B2 (en) | 2003-05-21 | 2004-04-23 | Method of preparing 4-R-substituted 4-demethoxydaunorubicin |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005021565A1 true WO2005021565A1 (en) | 2005-03-10 |
Family
ID=33457319
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2004/016739 WO2005021565A1 (en) | 2003-05-21 | 2004-05-20 | Method of preparing 4-r-substituted 4-demethoxydaunorubicin |
Country Status (5)
Country | Link |
---|---|
US (2) | US7053191B2 (en) |
EP (1) | EP1625136B1 (en) |
DE (1) | DE04801954T1 (en) |
RU (1) | RU2336277C2 (en) |
WO (1) | WO2005021565A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1976858A2 (en) | 2005-12-13 | 2008-10-08 | Solux Corporation | Method for preparing 4-demethyldaunorubicin |
JP2014526480A (en) * | 2011-09-19 | 2014-10-06 | ヘレウス プレシャス メタルズ ゲーエムベーハー ウント コンパニー カーゲー | Crystallization of idarubicin hydrochloride |
RU2563453C2 (en) * | 2008-01-08 | 2015-09-20 | Солюкс Корпорейшен | Method of aralkylation of 4'-hydroxyl group of anthracyclines |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7053191B2 (en) * | 2003-05-21 | 2006-05-30 | Solux Corporation | Method of preparing 4-R-substituted 4-demethoxydaunorubicin |
US8802830B2 (en) * | 2005-12-20 | 2014-08-12 | Solux Corporation | Synthesis of epirubicin from 13-dihydrodaunorubicine |
WO2010028667A1 (en) * | 2008-09-11 | 2010-03-18 | W.C. Heraeus Gmbh | Genetically modified strains for biotransformations in anthracycline production |
US8846882B2 (en) * | 2011-04-29 | 2014-09-30 | Synbias Pharma Ag | Method of producing 4-demethoxydaunorubicin |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2215332A (en) * | 1988-02-25 | 1989-09-20 | Erba Carlo Spa | 4-Demethyl-4-0-(p-fluorobenzensulfonyl) anthracycline glycosides |
US5103029A (en) | 1988-04-11 | 1992-04-07 | Farmitalia Carlo Erba S.R.L. | Process for preparing 4-demethoxydaunomycinone |
US5218130A (en) | 1988-07-29 | 1993-06-08 | Farmitalia Carlo Erba S R L | 4-substituted anthracyclinones and their preparation |
US5587495A (en) | 1988-10-25 | 1996-12-24 | Farmitalia Carlo Erba Srl | 4-substituted anthracyclinones and anthracycline glycosides and the process for preparing them |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US448724A (en) * | 1891-03-24 | Adjustable brush-handle | ||
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 |
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 (en) | 1979-04-20 | 1986-06-11 | Hoffmann La Roche | POLYCYCLIC COMPOUNDS AND PROCEDURE FOR THEIR PREPARATION |
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 |
EP0335369A3 (en) | 1988-03-29 | 1990-03-28 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | New anthracycline derivatives and processes for the preparation of the same |
GB8904794D0 (en) | 1989-03-02 | 1989-04-12 | Erba Carlo Spa | Process for preparing anthracyclinones |
FI86293C (en) | 1989-04-28 | 1992-08-10 | Oiva Suutarinen | FOERFARANDE FOER RENING AV EN VAETSKA FRAON FASTA OCH UPPLOESTA FOERORENINGAR MEDELST ETT FLOTATIONSFILTRERINGSFOERFARANDE. |
MA21995A1 (en) | 1989-11-13 | 1991-07-01 | Menarini Farma Ind | NOVEL FLUORONAPHTHACENEDIONES, THEIR GLYCOZYL DERIVATIVES AND THEIR MANUFACTURING METHODS. |
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 (en) | 1995-03-22 | 1997-10-24 | Sicor Spa | PROCEDURE FOR THE PREPARATION OF ANTIBIOTICS OF THE CLASS OF ANTHRACYCLINES |
GB9516349D0 (en) | 1995-08-09 | 1995-10-11 | Pharmacia Spa | Aza-anthracyclinone derivatives |
WO1997023243A1 (en) | 1995-12-22 | 1997-07-03 | Bristol-Myers Squibb Company | Branched hydrazone linkers |
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 |
AUPP060797A0 (en) * | 1997-11-27 | 1998-01-08 | Baramy Engineering Pty Ltd | Filtering apparatus |
AUPQ319799A0 (en) | 1999-10-01 | 1999-10-28 | Institute Of Drug Technology Australia Limited | Chemical methods |
IT1318532B1 (en) | 2000-05-19 | 2003-08-27 | Antibioticos Spa | ANTHRACYCLINIC DERIVATIVES SYNTHESIS PROCEDURE. |
US7053191B2 (en) * | 2003-05-21 | 2006-05-30 | Solux Corporation | Method of preparing 4-R-substituted 4-demethoxydaunorubicin |
-
2004
- 2004-04-23 US US10/831,448 patent/US7053191B2/en not_active Expired - Lifetime
- 2004-05-20 EP EP04801954.1A patent/EP1625136B1/en not_active Not-in-force
- 2004-05-20 DE DE04801954T patent/DE04801954T1/en active Pending
- 2004-05-20 RU RU2005135262/04A patent/RU2336277C2/en not_active IP Right Cessation
- 2004-05-20 WO PCT/US2004/016739 patent/WO2005021565A1/en active Application Filing
-
2006
- 2006-05-29 US US11/420,774 patent/US20060205684A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2215332A (en) * | 1988-02-25 | 1989-09-20 | Erba Carlo Spa | 4-Demethyl-4-0-(p-fluorobenzensulfonyl) anthracycline glycosides |
US5103029A (en) | 1988-04-11 | 1992-04-07 | Farmitalia Carlo Erba S.R.L. | Process for preparing 4-demethoxydaunomycinone |
US5218130A (en) | 1988-07-29 | 1993-06-08 | Farmitalia Carlo Erba S R L | 4-substituted anthracyclinones and their preparation |
US5587495A (en) | 1988-10-25 | 1996-12-24 | Farmitalia Carlo Erba Srl | 4-substituted anthracyclinones and anthracycline glycosides and the process for preparing them |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1976858A2 (en) | 2005-12-13 | 2008-10-08 | Solux Corporation | Method for preparing 4-demethyldaunorubicin |
RU2563453C2 (en) * | 2008-01-08 | 2015-09-20 | Солюкс Корпорейшен | Method of aralkylation of 4'-hydroxyl group of anthracyclines |
JP2014526480A (en) * | 2011-09-19 | 2014-10-06 | ヘレウス プレシャス メタルズ ゲーエムベーハー ウント コンパニー カーゲー | Crystallization of idarubicin hydrochloride |
Also Published As
Publication number | Publication date |
---|---|
RU2336277C2 (en) | 2008-10-20 |
EP1625136A4 (en) | 2011-03-23 |
US20040236086A1 (en) | 2004-11-25 |
US20060205684A1 (en) | 2006-09-14 |
DE04801954T1 (en) | 2011-06-16 |
EP1625136A1 (en) | 2006-02-15 |
RU2005135262A (en) | 2006-05-27 |
EP1625136B1 (en) | 2016-02-24 |
US7053191B2 (en) | 2006-05-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20060205684A1 (en) | Method of preparing 4-r-substituted 4-demethoxydaunorubicin | |
CN101341166B (en) | Synthesis of epirubicin from 13-dihydrodaunorubicine | |
EP2187891A1 (en) | Epimerization of 4'-c bond and modification of 14-ch3-(co)-fragment in anthracyclin antibiotics | |
KR101480376B1 (en) | Crystallization of 4'-epidaunorubicinㆍhcl | |
CA1337762C (en) | Process for preparing 4-demethoxydaunomycinone | |
KR101563939B1 (en) | 4 Method of producing 4demethoxydaunorubicin | |
FI63419B (en) | FOERFARANDE FOER FRAMSTAELLNING AV NYA 4'-0-METYLDERIVAT AV ANHRACYKLINGLYKOSIDER | |
US4322412A (en) | Anthracycline glycosides, their preparation, use and compositions thereof | |
AU624444B2 (en) | New 4-substituted anthracyclinones and anthracycline glycosides and the process for preparing them | |
CA1291122C (en) | 3'-hydroxy-4'-epi-amino anthracyclines | |
CN100379749C (en) | Method of preparing 4-R-substituted 4-demethoxydaunorubicin | |
US8357785B2 (en) | Method of aralkylation of 4′-hydroxyl group of anthracylins | |
HU196821B (en) | Process for producing 6-deoxy-antracyclin-glycoside derivatives | |
UA91349C2 (en) | Compositions and processes for preparing 13-deoxy-anthracyclines | |
TWI331609B (en) | A process for producing 1, 2-trans glycoside compound | |
JPH05163293A (en) | Anthracycline-macrolide complex | |
CA1237714A (en) | Anthracycline glycosides | |
CN107698634B (en) | Preparation method of idarubicin hydrochloride | |
WO1992004362A1 (en) | 2-hydroxy- and 2-acyloxy-4-morpholinyl anthracyclines | |
GB2238540A (en) | 13-deoxy-4'-deoxy-4'-iodoanthracyclines and intermediates therefor | |
US4604381A (en) | 4-demethoxy-13-dihydrodaunorubicin and use thereof | |
RU2024483C1 (en) | 4-substituted anthracyclinones and anthracycline glycoside | |
KR830001612B1 (en) | The production of a selectively protected n-acylated derivative of an amino glycoside | |
JPH0343261B2 (en) | ||
Landells et al. | Synthesis of water soluble O-glycosides of N-(hydroxyalkyl) aminomethylferrocenes |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 20048137475 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004801954 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1374/MUMNP/2005 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2005135262 Country of ref document: RU |
|
WWP | Wipo information: published in national office |
Ref document number: 2004801954 Country of ref document: EP |