WO2001016089A1 - A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride - Google Patents

A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride Download PDF

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Publication number
WO2001016089A1
WO2001016089A1 PCT/IB2000/001182 IB0001182W WO0116089A1 WO 2001016089 A1 WO2001016089 A1 WO 2001016089A1 IB 0001182 W IB0001182 W IB 0001182W WO 0116089 A1 WO0116089 A1 WO 0116089A1
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WO
WIPO (PCT)
Prior art keywords
formula
cis
hydrochloride
dichlorophenyl
compound
Prior art date
Application number
PCT/IB2000/001182
Other languages
English (en)
French (fr)
Inventor
Sharad Kumar Vyas
Original Assignee
Sharad Kumar Vyas
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 Sharad Kumar Vyas filed Critical Sharad Kumar Vyas
Priority to AU65875/00A priority Critical patent/AU6587500A/en
Publication of WO2001016089A1 publication Critical patent/WO2001016089A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen

Definitions

  • This invention relates to a process for the preparation of N-methyl-4-
  • sertraline hydrochloride which is cis-(l S,4S)-N-methyl-4-(3 ,4-
  • serotonin resides in the cis-1 S,4S isomer i.e. cis-(l S, 4S)-N-methyl-4-
  • hydrochloride (I) commonly known as sertraline hydrochloride.
  • hydrochloride (II) are known in the literature.
  • the inline was hydrogenated using 10% Pd/C as catalyst to give the
  • a metal hydride reagent e.g. sodium
  • titanium tetrachloride is crucial, as the reagent is moisture sensitive and
  • the first object of the invention is to produce sertraline hydrochloride
  • Another object of the present invention is to produce cis-N-methyl-4-
  • Yet another object of the present invention is to produce the said
  • the present invention provides a process for preparation
  • naphthalenearnine hydrochloride i.e. sertraline hydrochloride of the
  • metal catalyst such as Raney Nickel
  • the invention also provides for preparation of intermediate cis-N-
  • hydrochloride of formula - VI which comprises the process steps (a), (b)
  • Solvent for the reaction is protic polar in the nature.
  • Protic polar solvent is protic polar solvent
  • lower alcohol such as C 1 -C 3 alcohols may be used.
  • C 1 -C 3 alcohols may be used.
  • the temperature as one of the preferred
  • parameters may be varied over the range of room temperature to 100°C.
  • Preferred solvent is methanol.
  • Preferred hydrogen pressure is 450-500 psi
  • isomer is carried out by separating all cis-isomers from the said isomeric
  • naphthalenone (15.0 gm) is taken, followed by addition of 250 ml.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/IB2000/001182 1999-09-01 2000-08-28 A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride WO2001016089A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU65875/00A AU6587500A (en) 1999-09-01 2000-08-28 A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahyd ro-1-naphthaleneamine hydrochloride

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN748/CAL/99 1999-09-01
IN748CA1999 IN185109B (cs) 1999-09-01 1999-09-01

Publications (1)

Publication Number Publication Date
WO2001016089A1 true WO2001016089A1 (en) 2001-03-08

Family

ID=11084493

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2000/001182 WO2001016089A1 (en) 1999-09-01 2000-08-28 A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride

Country Status (4)

Country Link
AR (1) AR025461A1 (cs)
AU (1) AU6587500A (cs)
IN (1) IN185109B (cs)
WO (1) WO2001016089A1 (cs)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002096860A1 (en) * 2001-05-31 2002-12-05 Orion Corporation Fermion Process for preparing sertraline intermediates
US6723878B2 (en) 2001-06-15 2004-04-20 Orion Corporation Fermion Method for preparing sertraline
US6809221B2 (en) 2000-03-14 2004-10-26 Teva Pharmaceutical Industries Ltd. Process for preparing (+)-cis-sertraline
US6897340B2 (en) 2002-04-29 2005-05-24 Teva Pharmaceutical Industries Ltd. Processes for preparation of polymorphic form II of sertraline hydrochloride
WO2006091732A1 (en) * 2005-02-23 2006-08-31 Teva Pharmaceutical Industries Ltd. Processes for preparing sertraline
WO2006129324A2 (en) 2005-06-03 2006-12-07 Hetero Drugs Limited A highly stereoselective synthesis of sertraline
US7262327B2 (en) 2003-09-05 2007-08-28 Teva Pharmaceutical Industries Ltd. Recycling process for preparing sertraline
US7276629B2 (en) 2003-04-14 2007-10-02 Teva Pharmaceutical Industries Ltd. Hydrogenation of imine intermediates of sertraline with catalysts
WO2007119247A2 (en) * 2006-04-17 2007-10-25 Unichem Laboratories Limited Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride)
US7345201B2 (en) 2005-02-23 2008-03-18 Teva Pharmaceutical Industries, Ltd. Processes for preparing sertraline

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030081A1 (en) * 1979-11-01 1981-06-10 Pfizer Inc. Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine and pharmaceutical compositions thereof
WO1999036394A1 (en) * 1998-01-16 1999-07-22 Pfizer Products Inc. Novel process for preparing a ketimine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0030081A1 (en) * 1979-11-01 1981-06-10 Pfizer Inc. Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine and pharmaceutical compositions thereof
WO1999036394A1 (en) * 1998-01-16 1999-07-22 Pfizer Products Inc. Novel process for preparing a ketimine

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6809221B2 (en) 2000-03-14 2004-10-26 Teva Pharmaceutical Industries Ltd. Process for preparing (+)-cis-sertraline
WO2002096860A1 (en) * 2001-05-31 2002-12-05 Orion Corporation Fermion Process for preparing sertraline intermediates
US6723878B2 (en) 2001-06-15 2004-04-20 Orion Corporation Fermion Method for preparing sertraline
US6897340B2 (en) 2002-04-29 2005-05-24 Teva Pharmaceutical Industries Ltd. Processes for preparation of polymorphic form II of sertraline hydrochloride
US7276629B2 (en) 2003-04-14 2007-10-02 Teva Pharmaceutical Industries Ltd. Hydrogenation of imine intermediates of sertraline with catalysts
US7262327B2 (en) 2003-09-05 2007-08-28 Teva Pharmaceutical Industries Ltd. Recycling process for preparing sertraline
WO2006091732A1 (en) * 2005-02-23 2006-08-31 Teva Pharmaceutical Industries Ltd. Processes for preparing sertraline
US7345201B2 (en) 2005-02-23 2008-03-18 Teva Pharmaceutical Industries, Ltd. Processes for preparing sertraline
US7518018B2 (en) 2005-02-23 2009-04-14 Teva Pharmaceutical Industries Ltd. Processes for preparing sertraline
WO2006129324A2 (en) 2005-06-03 2006-12-07 Hetero Drugs Limited A highly stereoselective synthesis of sertraline
WO2007119247A2 (en) * 2006-04-17 2007-10-25 Unichem Laboratories Limited Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride)
WO2007119247A3 (en) * 2006-04-17 2009-05-14 Unichem Lab Ltd Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride)

Also Published As

Publication number Publication date
AR025461A1 (es) 2002-11-27
IN185109B (cs) 2000-11-18
AU6587500A (en) 2001-03-26

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