FR2941454B1 - Proced de synthese du (1s,2r)-milnacipran - Google Patents

Proced de synthese du (1s,2r)-milnacipran

Info

Publication number
FR2941454B1
FR2941454B1 FR0950552A FR0950552A FR2941454B1 FR 2941454 B1 FR2941454 B1 FR 2941454B1 FR 0950552 A FR0950552 A FR 0950552A FR 0950552 A FR0950552 A FR 0950552A FR 2941454 B1 FR2941454 B1 FR 2941454B1
Authority
FR
France
Prior art keywords
give
milnacipran
amide
reacting
phthalimide
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
FR0950552A
Other languages
English (en)
Other versions
FR2941454A1 (fr
Inventor
Marc Nicolas
Paul Hellier
Catherine Diard
Laurent Subra
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pierre Fabre Medicament SA
Original Assignee
Pierre Fabre Medicament SA
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 Pierre Fabre Medicament SA filed Critical Pierre Fabre Medicament SA
Priority to FR0950552A priority Critical patent/FR2941454B1/fr
Priority to TW099101933A priority patent/TWI455911B/zh
Priority to RU2011135326/04A priority patent/RU2521342C2/ru
Priority to PCT/EP2010/051045 priority patent/WO2010086394A1/fr
Priority to ES10701538.0T priority patent/ES2472695T3/es
Priority to MA34052A priority patent/MA33025B1/fr
Priority to US13/146,361 priority patent/US8604241B2/en
Priority to PL10701538T priority patent/PL2391599T3/pl
Priority to CN201910530393.XA priority patent/CN110204455A/zh
Priority to JP2011546850A priority patent/JP5646509B2/ja
Priority to GEAP201012350A priority patent/GEP20135903B/en
Priority to AU2010209686A priority patent/AU2010209686B2/en
Priority to UAA201110404A priority patent/UA104884C2/uk
Priority to KR1020117019602A priority patent/KR101719011B1/ko
Priority to BRPI1007404A priority patent/BRPI1007404B8/pt
Priority to CN2010800057211A priority patent/CN102300840A/zh
Priority to CA2750488A priority patent/CA2750488C/fr
Priority to EP10701538.0A priority patent/EP2391599B1/fr
Priority to ARP100100245A priority patent/AR077526A1/es
Priority to NZ594291A priority patent/NZ594291A/xx
Priority to MX2011007846A priority patent/MX2011007846A/es
Publication of FR2941454A1 publication Critical patent/FR2941454A1/fr
Application granted granted Critical
Publication of FR2941454B1 publication Critical patent/FR2941454B1/fr
Priority to IL214241A priority patent/IL214241A/en
Priority to ZA2011/05414A priority patent/ZA201105414B/en
Priority to TN2011000363A priority patent/TN2011000363A1/fr
Priority to ARP190101513A priority patent/AR115475A2/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Steroid Compounds (AREA)

Abstract

La présente invention concerne un procédé de synthèse d'un sel d'addition d'acide pharmaceutiquement acceptable du (1S,2R)-milnacipran comprenant les étapes successives suivantes : (a) réaction du phénylacétonitrile et de la (R)-épichlorhydrine en présence d'une base contenant un métal alcalin, suivie d'un traitement basique, puis d'un traitement acide pour donner une lactone (b) réaction de ladite lactone avec MNEt , où M représente un métal alcalin, ou avec NHEt en présence d'un complexe acide de Lewis-amine, pour donner un amide-alcool (c) réaction dudit amide-alcool avec du chlorure de thionyle pour donner un amide chloré (d) réaction dudit amide chloré avec un sel de phtalimide pour donner un dérivé phtalimide (e) hydrolyse du groupement phtalimide dudit dérivé phtalimide pour donner le (1S, 2R)-milnacipran, et (f) salification du (1S,2R)-milnacipran dans un système de solvant approprié en présence d'un acide pharmaceutiquement acceptable.
FR0950552A 2009-01-29 2009-01-29 Proced de synthese du (1s,2r)-milnacipran Active FR2941454B1 (fr)

Priority Applications (25)

Application Number Priority Date Filing Date Title
FR0950552A FR2941454B1 (fr) 2009-01-29 2009-01-29 Proced de synthese du (1s,2r)-milnacipran
TW099101933A TWI455911B (zh) 2009-01-29 2010-01-25 用以合成（１ｓ，２ｒ）－米那普侖（ｍｉｌｎａｃｉｐｒａｎ）的方法
CN2010800057211A CN102300840A (zh) 2009-01-29 2010-01-29 (1s,2r)-米那普仑的合成方法
ES10701538.0T ES2472695T3 (es) 2009-01-29 2010-01-29 Procedimiento para la síntesis de (1S,2R)-milnacipr�n
MA34052A MA33025B1 (fr) 2009-01-29 2010-01-29 Procede pour la synthese de (1s.2r)-milnacipran
US13/146,361 US8604241B2 (en) 2009-01-29 2010-01-29 Method for synthesis of (1S, 2R)-milnacipran
PL10701538T PL2391599T3 (pl) 2009-01-29 2010-01-29 Sposób syntezy (1S,2R)-milnacipranu
CN201910530393.XA CN110204455A (zh) 2009-01-29 2010-01-29 (1s,2r)-米那普仑的合成方法
JP2011546850A JP5646509B2 (ja) 2009-01-29 2010-01-29 （１ｓ，２ｒ）−ミルナシプランの合成方法
GEAP201012350A GEP20135903B (en) 2009-01-29 2010-01-29 Method of (1s, 2r)-milnacipran synthesis
AU2010209686A AU2010209686B2 (en) 2009-01-29 2010-01-29 Method for synthesis of (1S, 2R)-milnacipran
UAA201110404A UA104884C2 (uk) 2009-01-29 2010-01-29 Спосіб синтезу (1s,2r)-мілнаципрану
RU2011135326/04A RU2521342C2 (ru) 2009-01-29 2010-01-29 Способ синтеза (1s,2r)-милнаципрана
BRPI1007404A BRPI1007404B8 (pt) 2009-01-29 2010-01-29 método para síntese de (1s,2r)-milnaciprano
PCT/EP2010/051045 WO2010086394A1 (fr) 2009-01-29 2010-01-29 Procédé pour la synthèse de (1s,2r)-milnacipran
CA2750488A CA2750488C (fr) 2009-01-29 2010-01-29 Procede pour la synthese de (1s,2r)-milnacipran
EP10701538.0A EP2391599B1 (fr) 2009-01-29 2010-01-29 Procédé pour la synthèse de (1s,2r)-milnacipran
ARP100100245A AR077526A1 (es) 2009-01-29 2010-01-29 Metodo para la sintesis de (1s,2r)- milnacipran
NZ594291A NZ594291A (en) 2009-01-29 2010-01-29 Stereoselective method for synthesis of (1s,2r)-milnacipran
MX2011007846A MX2011007846A (es) 2009-01-29 2010-01-29 Metodo para la sintesis de (1s, 2r)-milnacipran.
KR1020117019602A KR101719011B1 (ko) 2009-01-29 2010-01-29 (1ｓ, 2ｒ)-밀나시프란 합성 방법
IL214241A IL214241A (en) 2009-01-29 2011-07-21 METHOD FOR SYNTHESIS OF (s1, r2) - MILLENCIPER
ZA2011/05414A ZA201105414B (en) 2009-01-29 2011-07-22 Method for synthesis of (1s,2r)-milnacipran
TN2011000363A TN2011000363A1 (en) 2009-01-29 2011-07-22 Method for synthesis of (1s,2r)-milnacipran
ARP190101513A AR115475A2 (es) 2009-01-29 2019-06-04 Método para la síntesis de (1s,2r)-milnaciprán

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0950552A FR2941454B1 (fr) 2009-01-29 2009-01-29 Proced de synthese du (1s,2r)-milnacipran

Publications (2)

Publication Number Publication Date
FR2941454A1 FR2941454A1 (fr) 2010-07-30
FR2941454B1 true FR2941454B1 (fr) 2011-04-01

Family

ID=40920574

Family Applications (1)

Application Number Title Priority Date Filing Date
FR0950552A Active FR2941454B1 (fr) 2009-01-29 2009-01-29 Proced de synthese du (1s,2r)-milnacipran

Country Status (23)

Country Link
US (1) US8604241B2 (fr)
EP (1) EP2391599B1 (fr)
JP (1) JP5646509B2 (fr)
KR (1) KR101719011B1 (fr)
CN (2) CN110204455A (fr)
AR (2) AR077526A1 (fr)
AU (1) AU2010209686B2 (fr)
BR (1) BRPI1007404B8 (fr)
CA (1) CA2750488C (fr)
ES (1) ES2472695T3 (fr)
FR (1) FR2941454B1 (fr)
GE (1) GEP20135903B (fr)
IL (1) IL214241A (fr)
MA (1) MA33025B1 (fr)
MX (1) MX2011007846A (fr)
NZ (1) NZ594291A (fr)
PL (1) PL2391599T3 (fr)
RU (1) RU2521342C2 (fr)
TN (1) TN2011000363A1 (fr)
TW (1) TWI455911B (fr)
UA (1) UA104884C2 (fr)
WO (1) WO2010086394A1 (fr)
ZA (1) ZA201105414B (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2944011B1 (fr) * 2009-04-03 2011-05-20 Pf Medicament Derives d'aminocyclobutane ou d'aminocyclobutene, leur procede de preparation et leur utilisation a titre de medicaments.
WO2011158249A1 (fr) * 2010-06-16 2011-12-22 Glenmark Generics Limited Méthode de préparation d'un intermédiaire de milnacipran et son utilisation dans la préparation de milnacipran pur
WO2012046247A2 (fr) * 2010-10-06 2012-04-12 Msn Laboratories Limited Procédé de préparation de chlorhydrate de (±m1r(s), 2srr)l-2-(aminométhyl)-n,n-diéthyl-l-phénylcyclopropane carboxamide
WO2012101044A1 (fr) * 2011-01-24 2012-08-02 Bayer Cropscience Ag Procédé de préparation de 2,2-difluoroéthylamine à partir de 2,2-difluoro-1-chloroéthane
MX352881B (es) 2012-02-17 2017-12-13 Eisai R&D Man Co Ltd Metodos y compuestos utiles en la sintesis de antagonistas del receptor de orexina 2.
WO2014009767A1 (fr) 2012-07-07 2014-01-16 Micro Labs Limited Procédé perfectionné pour la préparation de dérivés de 1-aryl-2-aminométhylcyclopropanecarboxamide (z), de leurs isomères et de leurs sels
EP2805936A1 (fr) 2013-05-20 2014-11-26 Cosma S.p.A. Procédé de préparation de levomilnacipran HCL
WO2014203277A2 (fr) * 2013-06-19 2014-12-24 Msn Laboratories Private Limited Procédé de préparation de chlorhydrate de (1s-2r)-2-(aminométhyl)-n-n'-diéthyl-1-phénylcyclopropanecarboxamide
CN103694162B (zh) * 2014-01-03 2015-09-02 上海现代制药股份有限公司 (1s,2r)-1-苯基2-(酞酰亚胺)甲基-n,n-二乙基-环丙甲酰胺的制备方法
CN104058992A (zh) * 2014-06-13 2014-09-24 上海现代制药股份有限公司 左旋米那普仑盐酸盐的晶型
JP2017533892A (ja) * 2014-10-03 2017-11-16 ピュラック バイオケム ビー． ブイ． Ｎ，ｎ−ジアルキルラクトアミドの製造法
ES2746081T3 (es) 2014-11-04 2020-03-04 Quim Sintetica S A Procedimiento para la preparación de (1S,2R)-milnaciprán
CN106083638A (zh) * 2016-07-07 2016-11-09 佛山市隆信医药科技有限公司 一种盐酸左旋米那普仑的制备方法
CN111175387B (zh) * 2018-11-13 2022-06-07 成都康弘药业集团股份有限公司 一种米那普仑异构体的检测方法

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Publication number Priority date Publication date Assignee Title
FR2508035A1 (fr) 1981-06-23 1982-12-24 Fabre Sa Pierre Derives d'aryl-1-aminomethyl-2 cyclopropanes carboxamides (z), leur preparation et leur application en tant que medicaments utiles dans le traitement des troubles du systeme nerveux central
FR2581059B1 (fr) 1985-04-25 1988-04-22 Pf Medicament Procede de preparation du chlorhydrate de phenyl-1 diethyl amino carbonyl-1 aminomethyl-2 cyclopropane (z)
FR2640972B1 (fr) * 1988-12-28 1991-04-19 Pf Medicament
JPH0834765A (ja) * 1994-02-22 1996-02-06 Asahi Chem Ind Co Ltd アミノアルキルシクロプロパン誘導体
US5621142A (en) 1994-02-22 1997-04-15 Asahi Kasei Kogyo Kabushiki Kaisha Aminoalkylcyclopropane derivatives
US7309799B2 (en) 2004-06-01 2007-12-18 Collegium Pharmaceutical, Inc. Methods for the synthesis of milnacipran and congeners thereof
JP4712320B2 (ja) 2004-06-16 2011-06-29 住友化学株式会社 ２−オキソ−１−フェニル−３−オキサビシクロ［３．１．０］ヘキサンの製造方法
JP4418717B2 (ja) * 2004-06-24 2010-02-24 住友化学株式会社 （ｚ）−１−フェニル−１−ジエチルアミノカルボニル−２−アミノメチルシクロプロパン塩酸塩の製造方法
KR101070721B1 (ko) 2004-06-25 2011-10-07 스미또모 가가꾸 가부시키가이샤 (ｚ)-1-페닐-1-디에틸아미노카르보닐-2-히드록시메틸시클로프로판의 제조 방법
JP4828863B2 (ja) 2005-01-28 2011-11-30 住友化学株式会社 （ｚ）−１−フェニル−１−（ｎ，ｎ−ジエチルアミノカルボニル）−２−フタルイミドメチルシクロプロパンの製造方法
KR100772244B1 (ko) * 2005-07-20 2007-11-01 안국약품 주식회사 밀나시프란염산염의 제조방법
TWI549455B (zh) 2009-12-04 2016-09-11 內數位專利控股公司 混合網路匯聚閘道延伸區域ip存取

Also Published As

Publication number Publication date
RU2011135326A (ru) 2013-03-10
BRPI1007404B1 (pt) 2020-10-13
AU2010209686B2 (en) 2014-06-05
TW201031623A (en) 2010-09-01
TN2011000363A1 (en) 2013-03-27
BRPI1007404B8 (pt) 2021-05-25
UA104884C2 (uk) 2014-03-25
CN110204455A (zh) 2019-09-06
GEP20135903B (en) 2013-08-12
AU2010209686A1 (en) 2011-08-18
JP2012516307A (ja) 2012-07-19
MA33025B1 (fr) 2012-02-01
BRPI1007404A2 (pt) 2016-02-16
AR115475A2 (es) 2021-01-20
RU2521342C2 (ru) 2014-06-27
US20110295036A1 (en) 2011-12-01
CA2750488C (fr) 2016-12-13
ZA201105414B (en) 2012-03-28
EP2391599A1 (fr) 2011-12-07
JP5646509B2 (ja) 2014-12-24
PL2391599T3 (pl) 2014-09-30
IL214241A0 (en) 2011-09-27
WO2010086394A1 (fr) 2010-08-05
US8604241B2 (en) 2013-12-10
TWI455911B (zh) 2014-10-11
KR20110108409A (ko) 2011-10-05
EP2391599B1 (fr) 2014-04-09
CA2750488A1 (fr) 2010-08-05
FR2941454A1 (fr) 2010-07-30
NZ594291A (en) 2012-11-30
ES2472695T3 (es) 2014-07-02
CN102300840A (zh) 2011-12-28
KR101719011B1 (ko) 2017-03-22
AR077526A1 (es) 2011-09-07
MX2011007846A (es) 2011-12-14
IL214241A (en) 2015-03-31

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