WO2011006455A3 - Method of preparing desvenlafaxine and its salts - Google Patents

Method of preparing desvenlafaxine and its salts Download PDF

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Publication number
WO2011006455A3
WO2011006455A3 PCT/CZ2010/000074 CZ2010000074W WO2011006455A3 WO 2011006455 A3 WO2011006455 A3 WO 2011006455A3 CZ 2010000074 W CZ2010000074 W CZ 2010000074W WO 2011006455 A3 WO2011006455 A3 WO 2011006455A3
Authority
WO
WIPO (PCT)
Prior art keywords
desvenlafaxine
formula
benzyldesvenlafaxine
derivative
inorganic
Prior art date
Application number
PCT/CZ2010/000074
Other languages
French (fr)
Other versions
WO2011006455A2 (en
Inventor
Petr Hruby
Ludek Ridvan
Stanislav Radl
Lukas Placek
Original Assignee
Zentiva, K.S.
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 Zentiva, K.S. filed Critical Zentiva, K.S.
Publication of WO2011006455A2 publication Critical patent/WO2011006455A2/en
Publication of WO2011006455A3 publication Critical patent/WO2011006455A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A method for the preparation of 4-(2-(dimethylamino)-l-(l-hydroxycyclohexyl)ethyl) phenol of formula (I), known under generic name desvenlafaxine, and its pharmaceutically acceptable salts, which comprises (a) mixing of the starting material O-benzyldesvenlafaxine or its derivative of formula (II), wherein R is H, 4-methyl, 4-methoxy, 3,4-dimethoxy, 2-nitro, 4-nitro, 4-chloro, 4- bromo, 2,6-dichloro or 2,6-difluoro, in an organic solvent or a mixture of solvents, and subsequent dissolving of the starting material by decreasing the pH to a value of 3 to 8 by addition of an inorganic or organic acid, or dissolving of O-benzyldesvenlafaxine or its derivative of formula (II) in an organic solvent or a mixture of solvents, wherein the compound of formula (II) is in the form of a salt with an inorganic or organic acid and the pH of the solution has a value of 3 to 8, (b) converting O-benzyldesvenlafaxine or its derivative of formula (II) to desvenlafaxine I by catalytic hydrogenation on a Raney catalyst, (c) removing the catalyst from the desvenlafaxine solution by filtration and subsequent increasing the pH to a value of 8 to 11 by addition of an inorganic or organic base, (d) isolating the desvenlafaxine base I by filtration, (e) converting the desvenlafaxine base I to a pharmaceutically acceptable salt. Formulae (I), (II)
PCT/CZ2010/000074 2009-07-15 2010-07-08 Method of preparing desvenlafaxine and its salts WO2011006455A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZPV2009-454 2009-07-15
CZ20090454A CZ2009454A3 (en) 2009-07-15 2009-07-15 Process for preparing desvenlafaxine and salts thereof

Publications (2)

Publication Number Publication Date
WO2011006455A2 WO2011006455A2 (en) 2011-01-20
WO2011006455A3 true WO2011006455A3 (en) 2011-05-05

Family

ID=43061354

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CZ2010/000074 WO2011006455A2 (en) 2009-07-15 2010-07-08 Method of preparing desvenlafaxine and its salts

Country Status (2)

Country Link
CZ (1) CZ2009454A3 (en)
WO (1) WO2011006455A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105801439B (en) * 2014-12-30 2019-06-04 深圳翰宇药业股份有限公司 A method of preparing O-Goven Wenfasin
MX367362B (en) 2016-06-29 2019-08-16 Alparis Sa De Cv Solid forms of desvenlafaxine.

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007147564A1 (en) * 2006-06-19 2007-12-27 Krka Process for preparation of 0-desmethylvenlafaxine and its analogues
WO2008103461A2 (en) * 2007-02-21 2008-08-28 Sepracor Inc. Solid forms comprising (-) o-desmethylvenlafaxine and uses thereof
WO2009084039A2 (en) * 2007-12-26 2009-07-09 Matrix Laboratories Limited Process for producing 1-[2-(dimethylamino)-1-(4-phenol)ethyl]cyclohexanol

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4535186A (en) 1983-04-19 1985-08-13 American Home Products Corporation 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives
IE56324B1 (en) * 1982-12-13 1991-06-19 American Home Prod Phenethylamine derivatives and intermediates therefor
CN101671260A (en) 2001-02-12 2010-03-17 惠氏公司 Method for preparing O-desmethyl-venlafaxine
UA80543C2 (en) 2001-12-04 2007-10-10 Wyeth Corp Method for the preparation of o-desmethylvenlafaxine
WO2007071404A1 (en) 2005-12-20 2007-06-28 Synthon B.V. Process for making desvenlafaxine
MX2007016179A (en) 2006-04-17 2008-03-11 Teva Pharma Polymorphic forms of tegaserod maleate.
EP2007708A1 (en) 2006-04-17 2008-12-31 Teva Pharmaceutical Industries Ltd Substantially pure o-desmethylvenlafaxine and processes for preparing it
AU2008211711A1 (en) * 2007-01-31 2008-08-07 Generics [Uk] Limited Process for the preparation of O-desmethyl venlafaxine
CZ2008756A3 (en) * 2008-11-27 2010-03-24 Zentiva, A. S. Process for preparing desvenlafaxine and salts thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007147564A1 (en) * 2006-06-19 2007-12-27 Krka Process for preparation of 0-desmethylvenlafaxine and its analogues
WO2008103461A2 (en) * 2007-02-21 2008-08-28 Sepracor Inc. Solid forms comprising (-) o-desmethylvenlafaxine and uses thereof
WO2009084039A2 (en) * 2007-12-26 2009-07-09 Matrix Laboratories Limited Process for producing 1-[2-(dimethylamino)-1-(4-phenol)ethyl]cyclohexanol

Also Published As

Publication number Publication date
WO2011006455A2 (en) 2011-01-20
CZ302145B6 (en) 2010-11-10
CZ2009454A3 (en) 2010-11-10

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