WO2007004230A3 - A novel process for the preparation of didanosine using novel intermediates - Google Patents

A novel process for the preparation of didanosine using novel intermediates Download PDF

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Publication number
WO2007004230A3
WO2007004230A3 PCT/IN2005/000229 IN2005000229W WO2007004230A3 WO 2007004230 A3 WO2007004230 A3 WO 2007004230A3 IN 2005000229 W IN2005000229 W IN 2005000229W WO 2007004230 A3 WO2007004230 A3 WO 2007004230A3
Authority
WO
WIPO (PCT)
Prior art keywords
dideoxy
novel
didehydroinosine
didanosine
preparation
Prior art date
Application number
PCT/IN2005/000229
Other languages
French (fr)
Other versions
WO2007004230A2 (en
Inventor
Reddy Bandi Parthasaradhi
Reddy Kura Rathnakar
Reddy Rapolu Raji
Reddy Dasari Muralidhara
Chander Reddy Kesireddy Subash
Original Assignee
Hetero Drugs Ltd
Reddy Bandi Parthasaradhi
Reddy Kura Rathnakar
Reddy Rapolu Raji
Reddy Dasari Muralidhara
Chander Reddy Kesireddy Subash
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 Hetero Drugs Ltd, Reddy Bandi Parthasaradhi, Reddy Kura Rathnakar, Reddy Rapolu Raji, Reddy Dasari Muralidhara, Chander Reddy Kesireddy Subash filed Critical Hetero Drugs Ltd
Priority to EP05783970A priority Critical patent/EP1910393A2/en
Priority to PCT/IN2005/000229 priority patent/WO2007004230A2/en
Priority to US11/570,358 priority patent/US7750153B2/en
Publication of WO2007004230A2 publication Critical patent/WO2007004230A2/en
Publication of WO2007004230A3 publication Critical patent/WO2007004230A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical

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

Abstract

The present invention relates to novel crystalline alkali metal and alkaline earth metal salts of 2',3'-dideoxy-2',3'-didehydroinosine. The present invention also provides a novel process for preparation of didanosine in high yield and purity using novel intermediates. Thus, for example, 5'-O-acetyl-2',3'-dideoxy-2',3'-didehydroinosine is reacted with monomethyl amine to give 2',3'-dideoxy-2',3'-didehydro inosine, which is then reacted with sodium hydroxide and crystallized to give crystalline 2',3'-dideoxy-2',3'-didehydroinosine sodium salt. 2',3'-Dideoxy-2',3'-didehydroinosine sodium salt is hydrogenated using raney nickel catalyst in aqueous medium and then neutralized with hydrochloric acid to yield didanosine.
PCT/IN2005/000229 2005-07-05 2005-07-05 A novel process for the preparation of didanosine using novel intermediates WO2007004230A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05783970A EP1910393A2 (en) 2005-07-05 2005-07-05 A novel process for the preparation of didanosine using novel intermediates
PCT/IN2005/000229 WO2007004230A2 (en) 2005-07-05 2005-07-05 A novel process for the preparation of didanosine using novel intermediates
US11/570,358 US7750153B2 (en) 2005-07-05 2005-07-05 Process for the preparation of didanosine using novel intermediates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2005/000229 WO2007004230A2 (en) 2005-07-05 2005-07-05 A novel process for the preparation of didanosine using novel intermediates

Publications (2)

Publication Number Publication Date
WO2007004230A2 WO2007004230A2 (en) 2007-01-11
WO2007004230A3 true WO2007004230A3 (en) 2008-04-10

Family

ID=37604888

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2005/000229 WO2007004230A2 (en) 2005-07-05 2005-07-05 A novel process for the preparation of didanosine using novel intermediates

Country Status (3)

Country Link
US (1) US7750153B2 (en)
EP (1) EP1910393A2 (en)
WO (1) WO2007004230A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007004230A2 (en) 2005-07-05 2007-01-11 Hetero Drugs Limited A novel process for the preparation of didanosine using novel intermediates

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0291096A (en) * 1988-09-28 1990-03-30 Sanyo Kokusaku Pulp Co Ltd Production of 2',3'-dideoxypurine nucleosides
WO1992015598A1 (en) * 1991-03-07 1992-09-17 University Of Georgia Research Foundation, Inc. Process for the deoxygenation of nucleosides
WO1993023413A1 (en) * 1992-05-13 1993-11-25 Ribozyme Pharmaceuticals, Inc. Synthesis of nucleotide monomers
WO2006128328A1 (en) * 2005-05-30 2006-12-07 Shanghai Aurisco International Trading Co., Ltd. A process for preparing didanosine

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CA1314875C (en) 1985-05-15 1993-03-23 George Walter Koszalka Therapeutic nucleosides
US5455339A (en) * 1986-05-01 1995-10-03 University Of Georgia Research Foundation, Inc. Method for the preparation of 2',3'-dideoxy and 2',3'-dideoxydide-hydro nucleosides
US5466793A (en) * 1988-03-01 1995-11-14 Ajinomoto Co., Inc. Process for preparing 2', 3'- dideoxyinosine
US5290927A (en) * 1988-03-01 1994-03-01 Ajinomoto Co., Inc. Process for preparing 2',3'-dideoxyadenosine
US6207650B1 (en) * 1989-05-15 2001-03-27 Bristol-Myers Squibb Company Antiviral, highly water soluble, stable, crystalline salts of 2′, 3′-dideoxyinosine, 2′, 3′-dideoxy-2′, 3′-didehydrothymidine and 2′, 3′-dideoxy-2′-fluoroinosine
US5451671A (en) * 1992-07-27 1995-09-19 Ajinomoto Co., Inc. Method of purifying 2',3'-dideoxynucleosides
GB9807354D0 (en) * 1998-04-07 1998-06-03 Glaxo Group Ltd Antiviral compound
US7141593B1 (en) * 1999-06-04 2006-11-28 Abbott Laboratories Pharmaceutical formulations
HUP0400446A2 (en) * 2001-05-22 2004-09-28 Pfizer Products Inc. Crystal forms of azithromycin
US6821502B2 (en) * 2002-06-12 2004-11-23 Chevron U.S.A. Inc. Method of making aluminum-containing zeolite with IFR structure
JP4656604B2 (en) * 2003-06-16 2011-03-23 味の素株式会社 Inosine derivative and method for producing the same
AR047541A1 (en) * 2004-02-13 2006-01-25 Sandoz Ag PHOSPHATE OF 5 - [[4- [2-METHYL-2-PYRIDINYL-AMINO-ETOXI] PHENYL] METHYL] -2,4 THYZOLIDINADION (ROSIGLITAZONE) AND ITS POLYMORPHIC FORMS
US7351833B2 (en) * 2004-07-23 2008-04-01 Abbott Laboratories (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate
US7723309B2 (en) * 2005-05-03 2010-05-25 Boehringer Ingelheim International Gmbh Crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments
UA91546C2 (en) * 2005-05-03 2010-08-10 Бьорінгер Інгельхайм Інтернаціональ Гмбх Crystalline form of 1-chloro-4-(я-d-glucopyranos-1-yl)-2-[4-((s)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments
WO2007004230A2 (en) 2005-07-05 2007-01-11 Hetero Drugs Limited A novel process for the preparation of didanosine using novel intermediates
US7837978B2 (en) * 2006-10-13 2010-11-23 Chevron U.S.A. Inc. Process for preparing aluminum-containing molecular sieve SSZ-26
WO2008143500A1 (en) * 2007-05-22 2008-11-27 Ultimorphix Technologies B.V. Tenofovir disoproxil hemi-fumaric acid co-crystal

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0291096A (en) * 1988-09-28 1990-03-30 Sanyo Kokusaku Pulp Co Ltd Production of 2',3'-dideoxypurine nucleosides
WO1992015598A1 (en) * 1991-03-07 1992-09-17 University Of Georgia Research Foundation, Inc. Process for the deoxygenation of nucleosides
WO1993023413A1 (en) * 1992-05-13 1993-11-25 Ribozyme Pharmaceuticals, Inc. Synthesis of nucleotide monomers
WO2006128328A1 (en) * 2005-05-30 2006-12-07 Shanghai Aurisco International Trading Co., Ltd. A process for preparing didanosine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE CASREACT [online] CHU C.K. ET AL.: "General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides", XP008113835, accession no. STN Database accession no. (110:193313) *
JOURNAL OF ORGANIC CHEMISTRY, vol. 54, no. 9, 1989, pages 2217 - 2225 *

Also Published As

Publication number Publication date
EP1910393A2 (en) 2008-04-16
US20080293938A1 (en) 2008-11-27
WO2007004230A2 (en) 2007-01-11
US7750153B2 (en) 2010-07-06

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