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WO2011073997A3 - Process for preparing paliperidone and pharmaceutically acceptable salts thereof - Google Patents

Process for preparing paliperidone and pharmaceutically acceptable salts thereof Download PDF

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Publication number
WO2011073997A3
WO2011073997A3 PCT/IN2010/000794 IN2010000794W WO2011073997A3 WO 2011073997 A3 WO2011073997 A3 WO 2011073997A3 IN 2010000794 W IN2010000794 W IN 2010000794W WO 2011073997 A3 WO2011073997 A3 WO 2011073997A3
Authority
WO
WIPO (PCT)
Prior art keywords
hydroxy
pharmaceutically acceptable
acceptable salts
pyrimidin
paliperidone
Prior art date
Application number
PCT/IN2010/000794
Other languages
French (fr)
Other versions
WO2011073997A2 (en
Inventor
Shriprakash Dhar Dwivedi
Dhimant Jasubhai Patel
Rushikesh Udaykumar Roy
Mayur Ramnikbhai Patel
Original Assignee
Cadila Healthcare Limited
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 Cadila Healthcare Limited filed Critical Cadila Healthcare Limited
Publication of WO2011073997A2 publication Critical patent/WO2011073997A2/en
Publication of WO2011073997A3 publication Critical patent/WO2011073997A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention discloses the process for the preparation of paliperidone and its pharmaceutically acceptable salts comprising (a) condensing 2-amino-3-hydroxy- pyridine with 2-acetylbutyro lactone in the presence of an acid catalyst to isolate 9- hydroxy-3-(2-hydroxyethyl)-2-rnethyl-4H-pyrido[l, 2-a] pyrimidin-4-one; treating 9- hydroxy-3-(2-hydroxyethyl)-2-methyl-4H-pyrido[l, 2-a] pyrimidin-4-one with a chlorinating agent; hydrogenating the product in the presence of one or more lewis acids to obtain 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrrido[l,2-a]- pyrimidin-4-one; and condensing3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2- methyl-4H-pyrrido[l,2-a]-pyrimidin-4-one. The present invention also discloses processes for the preparation of intermediates useful in the preparation of paliperidone and its pharmaceutically acceptable salts.
PCT/IN2010/000794 2009-12-14 2010-12-08 Process for preparing paliperidone and pharmaceutically acceptable salts thereof WO2011073997A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2882MU2009 2009-12-14
IN2882/MUM/2009 2009-12-14

Publications (2)

Publication Number Publication Date
WO2011073997A2 WO2011073997A2 (en) 2011-06-23
WO2011073997A3 true WO2011073997A3 (en) 2011-12-22

Family

ID=44022832

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2010/000794 WO2011073997A2 (en) 2009-12-14 2010-12-08 Process for preparing paliperidone and pharmaceutically acceptable salts thereof

Country Status (1)

Country Link
WO (1) WO2011073997A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104557915B (en) * 2014-12-01 2017-01-11 浙江京新药业股份有限公司 Method for preparing high-purity paliperidone II crystal form

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104292226B (en) * 2013-07-16 2016-12-28 江苏恩华药业股份有限公司 9-hydroxy-risperidone amino acid derivatives and application thereof
CN104502466B (en) * 2014-11-20 2021-01-26 万全万特制药（厦门）有限公司 Method for separating and measuring paliperidone raw material and preparation thereof by liquid chromatography

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014691A1 (en) * 1993-11-23 1995-06-01 Janssen Pharmaceutica N.V. NOVEL 9-HYDROXY-PYRIDO[1,2-a]PYRIMIDIN-4-ONE ETHER DERIVATIVES
WO2006027370A1 (en) * 2004-09-09 2006-03-16 Janssen Pharmaceutica N.V. PREPARATION OF 9-HYDROXY-3- (2-HYDROXYETHYL) -2-METHYL-4H-PYRID0[1, 2-a] PYRIMIDIN-4-ONE AND CRYSTALS THEREOF
WO2008024415A2 (en) * 2006-08-23 2008-02-28 Teva Pharmaceutical Insustries Ltd. Process for the synthesis of cmhtp and intermediates thereof
WO2008087557A2 (en) * 2007-01-08 2008-07-24 Actavis Group Ptc Ehf An improved process for preparation of 9-hydroxy-3-(2-chloroethyl)- 2-methyl-4h-pyrido[1,2-a]pyrimidin-4-one hydrochloride
WO2008140646A2 (en) * 2007-05-10 2008-11-20 Teva Pharmaceutical Industries Ltd. Process for the synthesis of cmhtp and intermediates thereof
US20090048272A1 (en) * 2007-08-16 2009-02-19 Pratap Reddy Padi Preparation of paliperidone
WO2009047499A2 (en) * 2007-10-09 2009-04-16 Cipla Limited Processes for the preparation of paliperidone and pharmaceutically acceptable salts thereof and intermediates for use in the processes
WO2009116071A2 (en) * 2008-02-05 2009-09-24 Watson Pharma Private Limited An improved process for preparation of paliperidone
WO2009144288A1 (en) * 2008-05-29 2009-12-03 Inke, S.A. Process to prepare paliperidone and intermediates thereof
WO2010064134A2 (en) * 2008-12-05 2010-06-10 Cadila Pharmaceuticals Ltd. Process of synthesis of paliperidone

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5158952A (en) 1988-11-07 1992-10-27 Janssen Pharmaceutica N.V. 3-[2-[4-(6-fluoro-1,2-benzisoxozol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9 tetrahydro-9-hydroxy-2-methyl-4H-pyrido [1,2-a]pyrimidin-4-one, compositions and method of use
US20080171876A1 (en) 2007-05-10 2008-07-17 Santiago Ini Pure paliperidone and processes for preparing thereof

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014691A1 (en) * 1993-11-23 1995-06-01 Janssen Pharmaceutica N.V. NOVEL 9-HYDROXY-PYRIDO[1,2-a]PYRIMIDIN-4-ONE ETHER DERIVATIVES
WO2006027370A1 (en) * 2004-09-09 2006-03-16 Janssen Pharmaceutica N.V. PREPARATION OF 9-HYDROXY-3- (2-HYDROXYETHYL) -2-METHYL-4H-PYRID0[1, 2-a] PYRIMIDIN-4-ONE AND CRYSTALS THEREOF
WO2008024415A2 (en) * 2006-08-23 2008-02-28 Teva Pharmaceutical Insustries Ltd. Process for the synthesis of cmhtp and intermediates thereof
WO2008087557A2 (en) * 2007-01-08 2008-07-24 Actavis Group Ptc Ehf An improved process for preparation of 9-hydroxy-3-(2-chloroethyl)- 2-methyl-4h-pyrido[1,2-a]pyrimidin-4-one hydrochloride
WO2008140646A2 (en) * 2007-05-10 2008-11-20 Teva Pharmaceutical Industries Ltd. Process for the synthesis of cmhtp and intermediates thereof
US20090048272A1 (en) * 2007-08-16 2009-02-19 Pratap Reddy Padi Preparation of paliperidone
WO2009047499A2 (en) * 2007-10-09 2009-04-16 Cipla Limited Processes for the preparation of paliperidone and pharmaceutically acceptable salts thereof and intermediates for use in the processes
WO2009116071A2 (en) * 2008-02-05 2009-09-24 Watson Pharma Private Limited An improved process for preparation of paliperidone
WO2009144288A1 (en) * 2008-05-29 2009-12-03 Inke, S.A. Process to prepare paliperidone and intermediates thereof
WO2010064134A2 (en) * 2008-12-05 2010-06-10 Cadila Pharmaceuticals Ltd. Process of synthesis of paliperidone

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DE SMET K ET AL: "Selectivity Control by Use of Near-IR for a Hydrogenation Process", ORGANIC PROCESS RESEARCH AND DEVELOPMENT,, vol. 9, no. 3, 1 January 2005 (2005-01-01), pages 344 - 347, XP002477069, DOI: DOI:10.1021/OP049782X *
ZHANG H ET AL: "A blue-emitting organic compound 9-hydroxyl-3-hydroxyethyl-2-methyl-4 H-pyrido[1,2-a]pyrimidin-4-one: Synthesis, crystal structure and luminescent properties", SPECTROCHIMICA ACTA. PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, ELSEVIER, AMSTERDAM, NL, vol. 76, no. 5, 1 September 2010 (2010-09-01), pages 464 - 469, XP027066683, ISSN: 1386-1425, [retrieved on 20100306], DOI: 10.1016/J.SAA.2010.02.036 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104557915B (en) * 2014-12-01 2017-01-11 浙江京新药业股份有限公司 Method for preparing high-purity paliperidone II crystal form

Also Published As

Publication number Publication date
WO2011073997A2 (en) 2011-06-23

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