AR115475A2 - Método para la síntesis de (1s,2r)-milnaciprán - Google Patents
Método para la síntesis de (1s,2r)-milnacipránInfo
- Publication number
- AR115475A2 AR115475A2 ARP190101513A ARP190101513A AR115475A2 AR 115475 A2 AR115475 A2 AR 115475A2 AR P190101513 A ARP190101513 A AR P190101513A AR P190101513 A ARP190101513 A AR P190101513A AR 115475 A2 AR115475 A2 AR 115475A2
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- previous step
- reaction
- amide
- milnacipran
- Prior art date
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
Reivindicación 1: Un método para sintetizar una sal de adición de ácido farmacéutica aceptable de (1S,2R)-milnaciprán de la fórmula (1), que comprende los siguientes pasos sucesivos: (a) reacción de fenilacetonitrilo y de (R)-epiclorhidrina en presencia de una base que contiene un metal alcalino, seguida por un tratamiento básico, y luego por un tratamiento ácido para obtener la lactona de la fórmula (2); (b) reacción de la lactona de fórmula (2) obtenida en el paso (a) previo con MNEt₂, en donde M representa un metal alcalino, o con NHEt₂ en presencia de un complejo de ácido de Lewis-amina en donde la amina es seleccionada entre dietilamina, trietilamina, diisopropiletilamina, N,N-dietilanilina, N,N-dimetilbencilamina, N-metilpiperidina, N-metilmorfolina, N,N-dimetilpiperazina y hexametilentetramina, para obtener el amida-alcohol de la fórmula (3); (c) reacción del amida-alcohol de fórmula (3) obtenido en el paso (b) previo con cloruro de tionilo para obtener la amida clorada de la fórmula (4); (d) reacción de la amida clorada de fórmula (4) obtenida en el paso (c) previo con una sal de ftalimida, tal como la sal de potasio, para obtener el derivado de ftalimida de la fórmula (5); (e) hidrólisis del grupo ftalimida del derivado de ftalimida de fórmula (5) obtenido en el paso (d) previo, para obtener (1S,2R)-milnaciprán; y (f) salificación del (1S,2R)-milnaciprán obtenido en el paso (e) previo en un sistema adecuado de solventes, en presencia de un ácido farmacéuticamente aceptable, caracterizado porque los pasos (a) a (e) son llevados a cabo en un medio de reacción que comprende un mismo y único solvente que es tolueno.
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 (1)
| Publication Number | Publication Date |
|---|---|
| AR115475A2 true AR115475A2 (es) | 2021-01-20 |
Family
ID=40920574
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100100245A AR077526A1 (es) | 2009-01-29 | 2010-01-29 | Metodo para la sintesis de (1s,2r)- milnacipran |
| ARP190101513A AR115475A2 (es) | 2009-01-29 | 2019-06-04 | Método para la síntesis de (1s,2r)-milnaciprán |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100100245A AR077526A1 (es) | 2009-01-29 | 2010-01-29 | Metodo para la sintesis de (1s,2r)- milnacipran |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US8604241B2 (es) |
| EP (1) | EP2391599B1 (es) |
| JP (1) | JP5646509B2 (es) |
| KR (1) | KR101719011B1 (es) |
| CN (2) | CN102300840A (es) |
| AR (2) | AR077526A1 (es) |
| AU (1) | AU2010209686B2 (es) |
| BR (1) | BRPI1007404B8 (es) |
| CA (1) | CA2750488C (es) |
| ES (1) | ES2472695T3 (es) |
| FR (1) | FR2941454B1 (es) |
| GE (1) | GEP20135903B (es) |
| IL (1) | IL214241A (es) |
| MA (1) | MA33025B1 (es) |
| MX (1) | MX2011007846A (es) |
| NZ (1) | NZ594291A (es) |
| PL (1) | PL2391599T3 (es) |
| RU (1) | RU2521342C2 (es) |
| TN (1) | TN2011000363A1 (es) |
| TW (1) | TWI455911B (es) |
| UA (1) | UA104884C2 (es) |
| WO (1) | WO2010086394A1 (es) |
| ZA (1) | ZA201105414B (es) |
Families Citing this family (14)
| 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 (en) * | 2010-06-16 | 2011-12-22 | Glenmark Generics Limited | Process for preparation of milnacipran intermediate and its use in preparation of pure milnacipran |
| WO2012046247A2 (en) * | 2010-10-06 | 2012-04-12 | Msn Laboratories Limited | Process for the preparation of (±m1r(s), 2srr)l-2-(aminomethyl)-n,n-diethyl-l-phenylcyclopropane carboxamide hydrochloride |
| ES2613709T3 (es) * | 2011-01-24 | 2017-05-25 | Bayer Intellectual Property Gmbh | Procedimiento para la preparación de 2,2-difluoroetilamina a partir de 2,2-difluoro-1-cloroetano |
| US9416109B2 (en) * | 2012-02-17 | 2016-08-16 | Eisai R&D Management Co., Ltd. | Methods and compounds useful in the synthesis of orexin-2 receptor antagonists |
| WO2014009767A1 (en) | 2012-07-07 | 2014-01-16 | Micro Labs Limited | An improved process for the preparation of 1-aryl 2-aminomethyl cyclopropane carboxyamide (z) derivatives, their isomers and salts |
| EP2805936A1 (en) | 2013-05-20 | 2014-11-26 | Cosma S.p.A. | Process for preparing levomilnacipran HCL |
| WO2014203277A2 (en) * | 2013-06-19 | 2014-12-24 | Msn Laboratories Private Limited | Process for the preparation of (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropanearboxamide hydrochloride |
| 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 |
Family Cites Families (12)
| 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 (es) * | 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 |
| WO1995022521A1 (fr) | 1994-02-22 | 1995-08-24 | Asahi Kasei Kogyo Kabushiki Kaisha | Derive d'aminoalkylcyclopropane |
| WO2005118564A2 (en) | 2004-06-01 | 2005-12-15 | 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 |
| CN100579954C (zh) | 2004-06-25 | 2010-01-13 | 住友化学株式会社 | (z)-1-苯基-1-二乙氨基羰基-2-羟甲基环丙烷的制造方法 |
| 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 |
| KR20140068261A (ko) | 2009-12-04 | 2014-06-05 | 인터디지탈 패튼 홀딩스, 인크 | 하이브리드 네트워크에서 통합 게이트웨이에 대한 확장형 로컬 ｉｐ 액세스 |
-
2009
- 2009-01-29 FR FR0950552A patent/FR2941454B1/fr active Active
-
2010
- 2010-01-25 TW TW099101933A patent/TWI455911B/zh active
- 2010-01-29 KR KR1020117019602A patent/KR101719011B1/ko active IP Right Grant
- 2010-01-29 UA UAA201110404A patent/UA104884C2/uk unknown
- 2010-01-29 CA CA2750488A patent/CA2750488C/en active Active
- 2010-01-29 RU RU2011135326/04A patent/RU2521342C2/ru active
- 2010-01-29 GE GEAP201012350A patent/GEP20135903B/en unknown
- 2010-01-29 US US13/146,361 patent/US8604241B2/en active Active
- 2010-01-29 EP EP10701538.0A patent/EP2391599B1/en active Active
- 2010-01-29 MA MA34052A patent/MA33025B1/fr unknown
- 2010-01-29 PL PL10701538T patent/PL2391599T3/pl unknown
- 2010-01-29 AU AU2010209686A patent/AU2010209686B2/en active Active
- 2010-01-29 WO PCT/EP2010/051045 patent/WO2010086394A1/en active Application Filing
- 2010-01-29 AR ARP100100245A patent/AR077526A1/es not_active Application Discontinuation
- 2010-01-29 MX MX2011007846A patent/MX2011007846A/es active IP Right Grant
- 2010-01-29 ES ES10701538.0T patent/ES2472695T3/es active Active
- 2010-01-29 NZ NZ594291A patent/NZ594291A/xx unknown
- 2010-01-29 BR BRPI1007404A patent/BRPI1007404B8/pt active IP Right Grant
- 2010-01-29 JP JP2011546850A patent/JP5646509B2/ja active Active
- 2010-01-29 CN CN2010800057211A patent/CN102300840A/zh active Pending
- 2010-01-29 CN CN201910530393.XA patent/CN110204455A/zh active Pending
-
2011
- 2011-07-21 IL IL214241A patent/IL214241A/en active IP Right Grant
- 2011-07-22 TN TN2011000363A patent/TN2011000363A1/fr unknown
- 2011-07-22 ZA ZA2011/05414A patent/ZA201105414B/en unknown
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2019
- 2019-06-04 AR ARP190101513A patent/AR115475A2/es unknown
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