WO2008035358A3 - Process for preparing dapoxetine - Google Patents

Process for preparing dapoxetine Download PDF

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Publication number
WO2008035358A3
WO2008035358A3 PCT/IN2007/000225 IN2007000225W WO2008035358A3 WO 2008035358 A3 WO2008035358 A3 WO 2008035358A3 IN 2007000225 W IN2007000225 W IN 2007000225W WO 2008035358 A3 WO2008035358 A3 WO 2008035358A3
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WO
WIPO (PCT)
Prior art keywords
dapoxetine
dimethyl
ethyl
chiral acid
acid
Prior art date
Application number
PCT/IN2007/000225
Other languages
French (fr)
Other versions
WO2008035358A2 (en
Inventor
Axay Mukundray Dave
Dhimat Jasubhai Patel
Rajiv Kumar
Shriprakash Dhar Dwivedi
Original Assignee
Cadila Healthcare Ltd
Axay Mukundray Dave
Dhimat Jasubhai Patel
Rajiv Kumar
Shriprakash Dhar Dwivedi
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 Ltd, Axay Mukundray Dave, Dhimat Jasubhai Patel, Rajiv Kumar, Shriprakash Dhar Dwivedi filed Critical Cadila Healthcare Ltd
Publication of WO2008035358A2 publication Critical patent/WO2008035358A2/en
Publication of WO2008035358A3 publication Critical patent/WO2008035358A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • 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
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Reproductive Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Gynecology & Obstetrics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Endocrinology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

This invention relates to a new process for preparation of enantiomerically pure dapoxetine or an acid addition salt thereof i.e. S(+)-N,N-dimethyl-2-[2-(naphthalenyl oxy)ethyl]benzenemethanamine hydrochoride, a potent serotonin re-uptake inhibitor (SSRI), which comprises resolving racemic (±)-dapoxetine i.e. (±)- N,N-dimethyl-2-[2- (naphthalenyloxy)ethyl] benzene methanamine with a chiral acid so as to obtain salt of the chiral acid and (+)-dapoxetine, substantially free from (-)-dapoxetine.
PCT/IN2007/000225 2006-06-05 2007-06-05 Process for preparing dapoxetine WO2008035358A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB862/MUM/2006 2006-06-05
IN862MU2006 2006-06-05

Publications (2)

Publication Number Publication Date
WO2008035358A2 WO2008035358A2 (en) 2008-03-27
WO2008035358A3 true WO2008035358A3 (en) 2008-05-15

Family

ID=39100800

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000225 WO2008035358A2 (en) 2006-06-05 2007-06-05 Process for preparing dapoxetine

Country Status (1)

Country Link
WO (1) WO2008035358A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102942496A (en) * 2012-11-28 2013-02-27 扬州工业职业技术学院 Method for preparing (S)-N, N-dimethyl-3-(naphthol-1-oxygroup)-1- phenyl propyl group-1-amine

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101367739B (en) * 2008-09-24 2013-02-13 台州职业技术学院 Preparation of N,N-dimethyl-1-phenyl-3-(1-naphthoxy) propanamine
DE102009015702A1 (en) * 2009-03-31 2010-10-07 Ratiopharm Gmbh Tablets containing dapoxetine and dry processing for their preparation
KR101122558B1 (en) 2009-11-11 2012-03-16 한국화학연구원 Asymmetric synthesis of intermediates for preparing dapoxetine
WO2011058572A2 (en) 2009-11-13 2011-05-19 Symed Labs Limited Solid dapoxetine
CN101955436B (en) * 2010-08-10 2013-07-24 漆又毛 Naphthyloxy benzedrine derivatives and preparation method thereof
CN103130658A (en) * 2011-11-22 2013-06-05 重庆医药工业研究院有限责任公司 Dapoxetine hydrochlorate crystal form A and preparation method thereof
CN103145569A (en) * 2011-11-22 2013-06-12 重庆医药工业研究院有限责任公司 Crystal form B of dapoxetine hydrochloride, and preparation method thereof
CN103130660B (en) * 2011-11-25 2014-09-17 厦门福满药业有限公司 Acidic salt and crystal of dapoxetine and preparation method of crystal
CN103130661B (en) * 2011-11-25 2014-09-17 厦门福满药业有限公司 Crystal and amorphous substance of dapoxetine hydrochloride and preparation method thereof
CN103130659B (en) * 2011-11-25 2015-01-28 厦门福满药业有限公司 Crystal of acidic salt of dapoxetine and preparation method thereof
KR101382102B1 (en) * 2012-01-31 2014-04-04 주식회사 파마코스텍 A preparation method of (S)-dapoxetine hydrochloride
WO2014024205A1 (en) * 2012-08-07 2014-02-13 R L Fine Chem A method for preparing (s)-(+)-n, n-dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine or its salt and intermediate thereof
WO2014042416A1 (en) * 2012-09-13 2014-03-20 주식회사 씨티씨바이오 Oral composition containing dapoxetin-free base
EP2749553A1 (en) 2012-12-31 2014-07-02 Deva Holding Anonim Sirketi Process for preparation of enantiomerically pure S-(+)-N, N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine
CN103113292A (en) * 2013-03-04 2013-05-22 中国药科大学 Novel dapoxetine nicotinamide eutectic crystal form
CN103396320A (en) * 2013-08-21 2013-11-20 南京海融医药科技有限公司 (S)-3-chloro-N, N-dimethyl-1-phenyl-1-propylamine and method for preparing dapoxetine by using same as intermediate
CN104628584B (en) * 2013-11-08 2017-03-08 广州朗圣药业有限公司 A kind of preparation method for being suitable for industrialized high-purity Dapoxetine hydrochloride
CN104610076B (en) * 2015-01-08 2016-11-23 湖南中医药大学 A kind of S-dapoxetine and the synthetic method of salt thereof
CN106748817A (en) * 2016-12-06 2017-05-31 安徽省金楠医疗科技有限公司 A kind of dapoxetine hydrochloride preparation method
CN109400490A (en) * 2017-08-17 2019-03-01 扬子江药业集团江苏紫龙药业有限公司 A kind of preparation method of dapoxetine hydrochloride free alkali
CN108083991A (en) * 2017-11-29 2018-05-29 东北制药集团股份有限公司 It is a kind of to prepare 3-（1- naphthoxys）The method of -1- phenyl propanols
CN108276299B (en) * 2018-03-23 2020-08-14 苏州大学张家港工业技术研究院 Synthesis method of dapoxetine related substances
CN110903203B (en) * 2018-09-14 2022-11-18 天津药物研究院有限公司 Dapoxetine hydrochloride crystal and preparation method and application thereof
KR102323561B1 (en) * 2020-01-06 2021-11-09 (주)분자와물질 Aminoalcohol-boron-binol complexes and a method for preparing optically active aminoalcohol derivatives using the same
CN113801027A (en) * 2020-06-16 2021-12-17 扬子江药业集团江苏紫龙药业有限公司 Synthesis process of dapoxetine hydrochloride
CN112159328A (en) * 2020-06-28 2021-01-01 石家庄市度智医药科技有限公司 Resolution method of dapoxetine
CN113072466A (en) * 2021-04-01 2021-07-06 湖南普道医药技术有限公司 Synthetic method of dapoxetine impurity
CN114621107A (en) * 2022-04-01 2022-06-14 广药白云山化学制药(珠海)有限公司 Method for recycling product from dapoxetine hydrochloride mother liquor
CN114989046A (en) * 2022-06-22 2022-09-02 苏州开元民生科技股份有限公司 Synthetic method of dapoxetine oxidized impurities

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EP0288188A1 (en) * 1987-04-09 1988-10-26 Eli Lilly And Company 1-Phenyl-3-naphthalenyloxy-propanamines
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CN1709859A (en) * 2005-06-22 2005-12-21 曹丽 Method for preparing dextroa-[2-(naphthoxy, ethyl] phenyl methylamine derivatives
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Patent Citations (5)

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EP0288188A1 (en) * 1987-04-09 1988-10-26 Eli Lilly And Company 1-Phenyl-3-naphthalenyloxy-propanamines
US5135947A (en) * 1987-04-09 1992-08-04 Eli Lilly And Company 1-phenyl-3-naphthalenyloxypropanamines and their use as selective serotonin reuptake inhibitors
US5292962A (en) * 1992-12-11 1994-03-08 Eli Lilly And Company Intermediates to 1-phenyl-3-naphthalenyloxy-propanamines
CN1709859A (en) * 2005-06-22 2005-12-21 曹丽 Method for preparing dextroa-[2-(naphthoxy, ethyl] phenyl methylamine derivatives
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DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; CHEN, PINGANG ET AL: "Preparation of (+)-.alpha.-(2-(naphthalen-1-yloxy)ethyl)benzylamine derivatives for treatment of premature ejaculation", XP002472309, retrieved from STN Database accession no. 2006:1013880 *
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102942496A (en) * 2012-11-28 2013-02-27 扬州工业职业技术学院 Method for preparing (S)-N, N-dimethyl-3-(naphthol-1-oxygroup)-1- phenyl propyl group-1-amine
CN102942496B (en) * 2012-11-28 2014-06-11 扬州工业职业技术学院 Method for preparing (S)-N, N-dimethyl-3-(naphthol-1-oxygroup)-1- phenyl propyl group-1-amine

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