WO2000015647A3 - Synthetic method for the preparation of the antineoplastic agent etoposide - Google Patents

Synthetic method for the preparation of the antineoplastic agent etoposide Download PDF

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Publication number
WO2000015647A3
WO2000015647A3 PCT/CA1999/000820 CA9900820W WO0015647A3 WO 2000015647 A3 WO2000015647 A3 WO 2000015647A3 CA 9900820 W CA9900820 W CA 9900820W WO 0015647 A3 WO0015647 A3 WO 0015647A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
etoposide
synthetic method
dichloroacetyl
ethylidene
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.)
Ceased
Application number
PCT/CA1999/000820
Other languages
French (fr)
Other versions
WO2000015647A2 (en
Inventor
Ragina Naidu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Phytogen Life Sciences Inc
Original Assignee
Phytogen Life Sciences Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Phytogen Life Sciences Inc filed Critical Phytogen Life Sciences Inc
Priority to EP99942666A priority Critical patent/EP1117671A2/en
Priority to AU56123/99A priority patent/AU5612399A/en
Priority to CA002343803A priority patent/CA2343803A1/en
Publication of WO2000015647A2 publication Critical patent/WO2000015647A2/en
Publication of WO2000015647A3 publication Critical patent/WO2000015647A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins

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  • 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)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A synthetic method for the preparation of the anti-tumor drug Etoposide. In one embodiment, the method includes the direct condensation of 4'-demethyl epipodophylloxin with 2,3-di-O-dichloroacetyl-(4,6-O-ethylidene)-β-D-glucopyranose in the presence of trimethylsilyl trifluoromethane sulfonate (TMSOTf) to yield 4'-demethylepipodophyllotoxin-4-(2,3-di-O-dichloroacetyl-4,6-0-ethylidene)-β-D-glucopyranoside, followed by conversion of the same to etoposide. Other methods include use of different Lewis acids as catalyst, as well as different substituted glucopyranosides. This method provides enhanced yields over existing synthetic techniques, reduced reaction times and permits more favorable isolation reaction procedures.
PCT/CA1999/000820 1998-09-10 1999-09-10 Synthetic method for the preparation of the antineoplastic agent etoposide Ceased WO2000015647A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99942666A EP1117671A2 (en) 1998-09-10 1999-09-10 Synthetic method for the preparation of the antineoplastic agent etoposide
AU56123/99A AU5612399A (en) 1998-09-10 1999-09-10 Synthetic method for the preparation of the antineoplastic agent etoposide
CA002343803A CA2343803A1 (en) 1998-09-10 1999-09-10 Synthetic method for the preparation of the antineoplastic agent etoposide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15087998A 1998-09-10 1998-09-10
US09/150,879 1998-09-10

Publications (2)

Publication Number Publication Date
WO2000015647A2 WO2000015647A2 (en) 2000-03-23
WO2000015647A3 true WO2000015647A3 (en) 2000-07-20

Family

ID=22536399

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1999/000820 Ceased WO2000015647A2 (en) 1998-09-10 1999-09-10 Synthetic method for the preparation of the antineoplastic agent etoposide

Country Status (6)

Country Link
US (1) US6384201B1 (en)
EP (1) EP1117671A2 (en)
CN (1) CN1376159A (en)
AU (1) AU5612399A (en)
CA (1) CA2343803A1 (en)
WO (1) WO2000015647A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030158532A1 (en) 2002-02-20 2003-08-21 Magee Luke R. Disposable absorbent article designed to facilitate an easy intuitive change
US8716548B2 (en) 2002-02-20 2014-05-06 The Procter & Gamble Company Disposable absorbent article designed to facilitate an easy change
US20080004585A1 (en) 2006-06-30 2008-01-03 The Procter & Gamble Company Disposable article with serviceable indicia
CN105566412A (en) * 2016-01-18 2016-05-11 江西师范大学 Preparation method of etoposide, teniposide and analogues thereof
CN108129525B (en) * 2017-12-28 2019-11-22 山东铂源药业有限公司 A kind of preparation method of Etoposide intermediate
CN112079879B (en) * 2020-08-21 2022-01-14 华润双鹤药业股份有限公司沧州分公司 Novel synthesis method of teniposide intermediate and synthesis method of teniposide

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993002094A1 (en) * 1991-07-23 1993-02-04 Sicor Societa' Italiana Corticosteroidi S.P.A. A process for the preparation of demethylepypodophyllotoxin
US5206350A (en) * 1990-06-07 1993-04-27 Shanghai Institute Of Pharmaceutical Industry Synthetic process for the preparation of anti-tumor agent-etoposide

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL6613143A (en) 1965-09-21 1967-03-22
CH464957A (en) 1965-12-14 1968-11-15 Sandoz Ag Process for the preparation of a new glucoside
EP0111058B1 (en) 1982-11-26 1987-11-04 Nippon Kayaku Kabushiki Kaisha Process for producing 4'-demethyl-epipodophyllotoxin-beta-d-ethylidene-glucoside and acyl-derivative thereof
JPS60246393A (en) 1984-05-22 1985-12-06 Nippon Kayaku Co Ltd Novel preparation of etoposide
US4791207A (en) 1985-03-29 1988-12-13 Merck & Co., Inc. Enantioselective process for producing 1-betamethylcarbapenem antibiotic intermediates
US4997931A (en) 1990-06-11 1991-03-05 Bristol-Myers Squibb Company Epipodophyllotoxin glycosides
US5459248A (en) 1993-11-04 1995-10-17 Bristol-Myers Squibb Company Process of preparing etoposide phosphate and etoposide
ES2191733T3 (en) 1995-12-04 2003-09-16 Nippon Kayaku Kk PROCEDURE TO PRODUCE ETOPOSIDE.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5206350A (en) * 1990-06-07 1993-04-27 Shanghai Institute Of Pharmaceutical Industry Synthetic process for the preparation of anti-tumor agent-etoposide
WO1993002094A1 (en) * 1991-07-23 1993-02-04 Sicor Societa' Italiana Corticosteroidi S.P.A. A process for the preparation of demethylepypodophyllotoxin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ALLEVI, PIETRO ET AL: "Stereoselective glucosidation of podophyllum lignans. A new simple synthesis of etoposide", J. ORG. CHEM. (1993), 58(15), 4175-8, XP002137372 *

Also Published As

Publication number Publication date
US6384201B1 (en) 2002-05-07
WO2000015647A2 (en) 2000-03-23
CA2343803A1 (en) 2000-03-23
CN1376159A (en) 2002-10-23
EP1117671A2 (en) 2001-07-25
AU5612399A (en) 2000-04-03

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