WO2011113476A3 - Method for producing 2'-deoxyadenosine compounds - Google Patents

Method for producing 2'-deoxyadenosine compounds Download PDF

Info

Publication number
WO2011113476A3
WO2011113476A3 PCT/EP2010/053352 EP2010053352W WO2011113476A3 WO 2011113476 A3 WO2011113476 A3 WO 2011113476A3 EP 2010053352 W EP2010053352 W EP 2010053352W WO 2011113476 A3 WO2011113476 A3 WO 2011113476A3
Authority
WO
WIPO (PCT)
Prior art keywords
compound
beta
mixture
organic solvent
deoxyadenosine
Prior art date
Application number
PCT/EP2010/053352
Other languages
French (fr)
Other versions
WO2011113476A2 (en
Inventor
Oliver Jungmann
Adrian Thaler
Rolf HÄNSELER
Original Assignee
Cilag Ag
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 Cilag Ag filed Critical Cilag Ag
Priority to PCT/EP2010/053352 priority Critical patent/WO2011113476A2/en
Publication of WO2011113476A2 publication Critical patent/WO2011113476A2/en
Publication of WO2011113476A3 publication Critical patent/WO2011113476A3/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

Abstract

(A) reacting the alkali metal salt of 2, 6-dichlorpurine with a 2-desoxy-3, 5 -di-O-p-toluoyl-alpha-D-erythro-pentofuranose or a derivative thereof, in a suitable organic solvent, said reaction optionally being carried out in the presence of a Lewis-acid, whereby a mixture comprising the intermediate N (9) -beta-compound, the N (7) -beta-regio- isomer, and the N (9) -alpha-stereoisomer is formed; (B) isolating from said reaction mixture formed the crude reaction product comprising the intermediate N (9) -beta- compound by a purification method, preferably by precipitation or crystallization, using a suitable organic solvent or a mixture of such organic solvents or a mixture of one or more of such organic solvents with water, without using a chromatographic purification method, and (C) subjecting the isolated intermediate N (9 ) -beta-compound to ammonolysis, where upon the 2 '-deoxyadenosine compound is formed, and (D) precipitating or crystallizing the 2 '-deoxyadenosine compound as formed in step (C) from a suitable organic solvent.
PCT/EP2010/053352 2010-03-16 2010-03-16 Method for producing 2'-deoxyadenosine compounds WO2011113476A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2010/053352 WO2011113476A2 (en) 2010-03-16 2010-03-16 Method for producing 2'-deoxyadenosine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2010/053352 WO2011113476A2 (en) 2010-03-16 2010-03-16 Method for producing 2'-deoxyadenosine compounds

Publications (2)

Publication Number Publication Date
WO2011113476A2 WO2011113476A2 (en) 2011-09-22
WO2011113476A3 true WO2011113476A3 (en) 2012-09-07

Family

ID=44624814

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/053352 WO2011113476A2 (en) 2010-03-16 2010-03-16 Method for producing 2'-deoxyadenosine compounds

Country Status (1)

Country Link
WO (1) WO2011113476A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0173059A2 (en) * 1984-08-06 1986-03-05 Brigham Young University Method for the production of 2'-deoxyadenosine compounds
US4760137A (en) * 1984-08-06 1988-07-26 Brigham Young University Method for the production of 2'-deoxyadenosine compounds
EP1253154A1 (en) * 2001-04-12 2002-10-30 Mitsui Chemicals, Inc. Method for purifying 5'-protected 2'-deoxypurine nucleosides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5208327A (en) 1991-12-18 1993-05-04 Ortho Pharmaceutical Corporation Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0173059A2 (en) * 1984-08-06 1986-03-05 Brigham Young University Method for the production of 2'-deoxyadenosine compounds
US4760137A (en) * 1984-08-06 1988-07-26 Brigham Young University Method for the production of 2'-deoxyadenosine compounds
EP1253154A1 (en) * 2001-04-12 2002-10-30 Mitsui Chemicals, Inc. Method for purifying 5'-protected 2'-deoxypurine nucleosides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KAZIMIERCZUK Z ET AL: "Synthesis of 2'-Deoxytubercidin, 2'-Deoxyadenosine, and Related 2'-deoxynucleosides via a Novel direct Stereospecific Sodium Salt Glycosylation Procedure", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, ACS, US, vol. 106, 1 January 1984 (1984-01-01), pages 6379 - 6382, XP002422906, ISSN: 0002-7863, DOI: 10.1021/JA00333A046 *

Also Published As

Publication number Publication date
WO2011113476A2 (en) 2011-09-22

Similar Documents

Publication Publication Date Title
WO2011123668A3 (en) Stereoselective synthesis of phosphorus containing actives
WO2014089385A3 (en) Methods of synthesizing a prostacyclin analog
WO2008089984A3 (en) Process for the preparation of ezetimibe and derivatives thereof
WO2011071314A3 (en) Processes for preparing crystalline forms a and b of ilaprazole and process for converting the crystalline forms
WO2009143369A3 (en) Method of preparing nucleosides and analogs thereof without using chromatography
WO2013043009A3 (en) Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same
WO2011024192A3 (en) Novel polymorphs of raltegravir
MD20120129A2 (en) Process for the preparation of perindopril L-arginine salt
WO2012031045A3 (en) Phosphonate ester derivatives and methods of synthesis thereof
WO2010030132A3 (en) Purification method for adefovir dipivoxil
CN102348706A (en) Process for producing pyripyropene derivative
WO2010004578A3 (en) Novel and improved processes for the preparation of paliperidone
BR112017013025A2 (en) palm mud oil recovery
WO2009137192A3 (en) Purification of sucralose containing feed streams for sucralose crystallization
WO2007088558A3 (en) A process for purification of valsartan
CA2471730A1 (en) Process for preparing and purifying 1,7'-dimethyl-2'-propyl-2,5'-bi-1h-benzimidazole
WO2006098855A3 (en) Processes for preparing morphinans and intermediates thereof
ATE442371T1 (en) COMPLETELY SOLVENT-FREE CEFOTETAN ACID AND METHOD FOR THE PRODUCTION THEREOF.
WO2013016557A3 (en) Methods of isolating 4-chloro-2-fluoro-3-substituted-phenylboronic acids
WO2011113476A3 (en) Method for producing 2'-deoxyadenosine compounds
WO2011108009A3 (en) Process for the preparation of fampridine
WO2006084941A3 (en) Process for the preparation of irinotecan hydrochloride
WO2012012391A3 (en) Process for preparing pyrano - [2,3-c]pyridine derivatives
WO2016105107A3 (en) Efficient method for producing and purifying anhydrous sugar alcohol
WO2012115402A3 (en) Crystalline form of docetaxel and process for preparation thereof

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10708225

Country of ref document: EP

Kind code of ref document: A2