IE861057L - Preparation of midalcipran - Google Patents
Preparation of midalcipranInfo
- Publication number
- IE861057L IE861057L IE861057A IE105786A IE861057L IE 861057 L IE861057 L IE 861057L IE 861057 A IE861057 A IE 861057A IE 105786 A IE105786 A IE 105786A IE 861057 L IE861057 L IE 861057L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- phenyl
- see diagramm
- phthalimidomethylcyclopropane
- diethylaminocarbonyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 title 1
- 229960000600 milnacipran Drugs 0.000 title 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- JOTWZGIFEGRKFM-UHFFFAOYSA-N 2-[(1,3-dioxoisoindol-2-yl)methyl]-n,n-diethyl-1-phenylcyclopropane-1-carboxamide Chemical compound C1C(CN2C(C3=CC=CC=C3C2=O)=O)C1(C(=O)N(CC)CC)C1=CC=CC=C1 JOTWZGIFEGRKFM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 238000007038 hydrochlorination reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1. Process for the industrial preparation of (Z)-1-phenyl-1-diethylaminocarbonyl-2- aminomethylcyclopropane of formula I : see diagramm : EP0200638,P7,F2 characterized by the use of the following successive reaction steps : i) 1-phenyl-2-oxo-3-oxa(3: 1: 0) bicyclohexane of formula II : see diagramm : EP0200638,P8,F1 is opened by treatment with a phthalimide salt in an organic solvent ; ii) (Z)-1-phenyl-2-phthalimidomethylcyclopropane-carboxylic acid of formula III thus obtained see diagramm : EP0200638,P8,F2 is treated with an acid chloride, and then the acid chloride thus formed is amidified by condensation with diethylamine in an organic solvent ; and iii) (Z)-1-phenyl-1-diethylaminocarbonyl-2- phthalimidomethylcyclopropane of formula IV thus obtained : see diagramm : EP0200638,P8,F3 is then treated with an alkylamine or a primary hydroxyalkylamine by itself or in the presence of a solvent to obtain, after hydrochlorination, the compound of abovementioned formula I.
[EP0200638A1]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8506335A FR2581059B1 (en) | 1985-04-25 | 1985-04-25 | PROCESS FOR THE PREPARATION OF PHENYL-1 HYDROCHLORIDE DIETHYL AMINO CARBONYL-1 AMINOMETHYL-2 CYCLOPROPANE (Z) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE861057L true IE861057L (en) | 1986-10-25 |
| IE59015B1 IE59015B1 (en) | 1993-12-15 |
Family
ID=9318686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE105786A IE59015B1 (en) | 1985-04-25 | 1986-04-21 | Process for preparing (z)-1-phenyl-1-diethyl amino carbonyl-2-aminomethylcyclopropanehydrochloride |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0200638B1 (en) |
| JP (1) | JPS61251650A (en) |
| KR (1) | KR940006764B1 (en) |
| AR (1) | AR240695A1 (en) |
| AT (1) | ATE42273T1 (en) |
| AU (1) | AU587613B2 (en) |
| CA (1) | CA1266486A (en) |
| DE (1) | DE3662877D1 (en) |
| DK (1) | DK170888B1 (en) |
| ES (1) | ES8704449A1 (en) |
| FI (1) | FI87196C (en) |
| FR (1) | FR2581059B1 (en) |
| GE (1) | GEP19970789B (en) |
| GR (1) | GR860980B (en) |
| HU (1) | HU195182B (en) |
| IE (1) | IE59015B1 (en) |
| MX (1) | MX162896B (en) |
| NO (1) | NO165143C (en) |
| OA (1) | OA08241A (en) |
| PT (1) | PT82461B (en) |
| SU (1) | SU1443797A3 (en) |
| YU (1) | YU44915B (en) |
| ZA (1) | ZA862929B (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2640972B1 (en) * | 1988-12-28 | 1991-04-19 | Pf Medicament | |
| EP0747348A4 (en) * | 1994-02-22 | 1999-07-07 | Asahi Chemical Ind | Aminoalkylcyclopropane derivative |
| FR2752732B1 (en) * | 1996-08-28 | 1998-11-20 | Pf Medicament | EXTENDED RELEASE GALENIC FORM OF MILNACIPRAN |
| JP4418717B2 (en) * | 2004-06-24 | 2010-02-24 | 住友化学株式会社 | Process for producing (Z) -1-phenyl-1-diethylaminocarbonyl-2-aminomethylcyclopropane hydrochloride |
| JP4828863B2 (en) | 2005-01-28 | 2011-11-30 | 住友化学株式会社 | Process for producing (Z) -1-phenyl-1- (N, N-diethylaminocarbonyl) -2-phthalimidomethylcyclopropane |
| US8309128B2 (en) | 2005-06-10 | 2012-11-13 | Pierre Fabre Medicament | Stabilized milnacipran formulation |
| KR100772244B1 (en) * | 2005-07-20 | 2007-11-01 | 안국약품 주식회사 | Method for preparing Milnacifranine |
| CN101415677B (en) * | 2006-04-17 | 2012-05-23 | 住友化学株式会社 | Method for producing polycyclic lactams |
| JP5338035B2 (en) * | 2006-04-17 | 2013-11-13 | 住友化学株式会社 | Process for producing polycyclic lactams |
| WO2008104957A2 (en) * | 2007-02-28 | 2008-09-04 | Ranbaxy Laboratories Limited | Novel polymorphic forms of milnacipran hydrochloride |
| FR2941454B1 (en) | 2009-01-29 | 2011-04-01 | Pf Medicament | PROCESS FOR THE SYNTHESIS OF (1S, 2R) -MILNACIPRAN |
| US20100274050A1 (en) * | 2009-04-23 | 2010-10-28 | Glenmark Generics Limited | Solid milnacipran and process for the preparation of the same |
| US20140045936A1 (en) | 2011-04-21 | 2014-02-13 | Wake Forest University Health Sciences | Cyclopropyl derivatives and methods of use |
| CN103242289B (en) * | 2012-02-03 | 2015-01-07 | 暨明医药科技（苏州）有限公司 | Preparation method of N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thienyl)cyclopropanecarboxamide hydrochloride |
| 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 |
| WO2014058744A2 (en) | 2012-10-09 | 2014-04-17 | California Institute Of Technology | In vivo and in vitro olefin cyclopropanation catalyzed by heme enzymes |
| FR2998892B1 (en) * | 2012-12-04 | 2015-01-02 | Pf Medicament | AMINOCYCLOBUTANE DERIVATIVES, PROCESS FOR PREPARING THEM AND THEIR USE AS MEDICAMENTS |
| CN103613513B (en) * | 2013-12-09 | 2016-01-20 | 上海现代制药股份有限公司 | Milnacipran hydrochloride intermediate and its preparation method and application |
| US9399762B2 (en) | 2014-02-18 | 2016-07-26 | California Institute Of Technology | Methods and systems for sulfimidation or sulfoximidation of organic molecules |
| CN104058992A (en) * | 2014-06-13 | 2014-09-24 | 上海现代制药股份有限公司 | Crystal form of levomilnacipran hydrochloride |
| WO2016071303A1 (en) | 2014-11-04 | 2016-05-12 | Quimica Sintetica, S.A. | Process for the preparation of (1s,2r)-milnacipran |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508035A1 (en) * | 1981-06-23 | 1982-12-24 | Fabre Sa Pierre | ARYL-1-AMINOMETHYL-2 CYCLOPROPANES CARBOXAMIDE (Z) DERIVATIVES, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS USEFUL IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS |
-
1985
- 1985-04-25 FR FR8506335A patent/FR2581059B1/en not_active Expired
-
1986
- 1986-04-14 GR GR860980A patent/GR860980B/en unknown
- 1986-04-17 AU AU56343/86A patent/AU587613B2/en not_active Expired
- 1986-04-18 ZA ZA862929A patent/ZA862929B/en unknown
- 1986-04-21 IE IE105786A patent/IE59015B1/en not_active IP Right Cessation
- 1986-04-22 YU YU655/86A patent/YU44915B/en unknown
- 1986-04-22 NO NO861573A patent/NO165143C/en unknown
- 1986-04-22 EP EP86400873A patent/EP0200638B1/en not_active Expired
- 1986-04-22 DE DE8686400873T patent/DE3662877D1/en not_active Expired
- 1986-04-22 AT AT86400873T patent/ATE42273T1/en not_active IP Right Cessation
- 1986-04-23 CA CA000507320A patent/CA1266486A/en not_active Expired - Lifetime
- 1986-04-23 KR KR1019860003133A patent/KR940006764B1/en not_active Expired - Lifetime
- 1986-04-24 DK DK191286A patent/DK170888B1/en not_active IP Right Cessation
- 1986-04-24 SU SU864027356A patent/SU1443797A3/en active
- 1986-04-24 PT PT82461A patent/PT82461B/en unknown
- 1986-04-24 JP JP61095850A patent/JPS61251650A/en active Granted
- 1986-04-24 ES ES554321A patent/ES8704449A1/en not_active Expired
- 1986-04-24 MX MX2307A patent/MX162896B/en unknown
- 1986-04-24 HU HU861711A patent/HU195182B/en unknown
- 1986-04-25 AR AR30375986A patent/AR240695A1/en active
- 1986-04-25 FI FI861755A patent/FI87196C/en not_active IP Right Cessation
- 1986-04-25 OA OA58846A patent/OA08241A/en unknown
-
1993
- 1993-03-04 GE GEAP1993566A patent/GEP19970789B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |