DK170888B1 - Fremgangsmåde til fremstilling af hydrochloridt af 1-phenyl-1-di-ethylaminocarbonyl-2-aminomethyl-cyclopropan (Z) - Google Patents
Fremgangsmåde til fremstilling af hydrochloridt af 1-phenyl-1-di-ethylaminocarbonyl-2-aminomethyl-cyclopropan (Z) Download PDFInfo
- Publication number
- DK170888B1 DK170888B1 DK191286A DK191286A DK170888B1 DK 170888 B1 DK170888 B1 DK 170888B1 DK 191286 A DK191286 A DK 191286A DK 191286 A DK191286 A DK 191286A DK 170888 B1 DK170888 B1 DK 170888B1
- Authority
- DK
- Denmark
- Prior art keywords
- process according
- formula
- phenyl
- carried out
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 11
- GJJFMKBJSRMPLA-UHFFFAOYSA-N milnacipran Chemical compound C=1C=CC=CC=1C1(C(=O)N(CC)CC)CC1CN GJJFMKBJSRMPLA-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- XWJCCJTWOLBUSW-UHFFFAOYSA-N 2-[(1,3-dioxoisoindol-2-yl)methyl]-1-phenylcyclopropane-1-carboxylic acid Chemical compound C1C(CN2C(C3=CC=CC=C3C2=O)=O)C1(C(=O)O)C1=CC=CC=C1 XWJCCJTWOLBUSW-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 230000009435 amidation Effects 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 150000002596 lactones Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 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 description 6
- 229960000600 milnacipran Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- ATTLDOZXPZCOGK-UHFFFAOYSA-N (2-phenylcyclopropyl)methanamine Chemical compound NCC1CC1C1=CC=CC=C1 ATTLDOZXPZCOGK-UHFFFAOYSA-N 0.000 description 1
- IYHBDOQALHCIIA-UHFFFAOYSA-N 2-[(1,3-dioxoisoindol-2-yl)methyl]-n,n-diethylcyclopropane-1-carboxamide Chemical compound CCN(CC)C(=O)C1CC1CN1C(=O)C2=CC=CC=C2C1=O IYHBDOQALHCIIA-UHFFFAOYSA-N 0.000 description 1
- FCVIWMMSEWILOP-UHFFFAOYSA-N 2-n,2-n-dimethylbenzene-1,2-dicarboxamide Chemical compound CN(C)C(=O)C1=CC=CC=C1C(N)=O FCVIWMMSEWILOP-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8506335 | 1985-04-25 | ||
| FR8506335A FR2581059B1 (fr) | 1985-04-25 | 1985-04-25 | Procede de preparation du chlorhydrate de phenyl-1 diethyl amino carbonyl-1 aminomethyl-2 cyclopropane (z) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK191286D0 DK191286D0 (da) | 1986-04-24 |
| DK191286A DK191286A (da) | 1986-10-26 |
| DK170888B1 true DK170888B1 (da) | 1996-03-04 |
Family
ID=9318686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK191286A DK170888B1 (da) | 1985-04-25 | 1986-04-24 | Fremgangsmåde til fremstilling af hydrochloridt af 1-phenyl-1-di-ethylaminocarbonyl-2-aminomethyl-cyclopropan (Z) |
Country Status (23)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2640972B1 (enrdf_load_stackoverflow) * | 1988-12-28 | 1991-04-19 | Pf Medicament | |
| EP0747348A4 (en) * | 1994-02-22 | 1999-07-07 | Asahi Chemical Ind | AMINOALKYLCYCLOPROPAN DERIVATIVES |
| FR2752732B1 (fr) * | 1996-08-28 | 1998-11-20 | Pf Medicament | Forme galenique a liberation prolongee de milnacipran |
| 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 |
| 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 |
| EP1894565B1 (en) | 2005-06-10 | 2013-10-30 | Pierre Fabre Médicament S.A. | Stabilized milnacipran formulation |
| KR100772244B1 (ko) * | 2005-07-20 | 2007-11-01 | 안국약품 주식회사 | 밀나시프란염산염의 제조방법 |
| SG160363A1 (en) * | 2006-04-17 | 2010-04-29 | Sumitomo Chemical Company Limt | Ester of cyclic carboxylic acid |
| JP5338035B2 (ja) * | 2006-04-17 | 2013-11-13 | 住友化学株式会社 | 多環式ラクタム類の製造方法 |
| US20100145099A1 (en) * | 2007-02-28 | 2010-06-10 | Ranbaxy Laboratories Limited | Novel polymorphic forms of milnacipran hydrochloride |
| FR2941454B1 (fr) | 2009-01-29 | 2011-04-01 | Pf Medicament | Proced de synthese du (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 (zh) * | 2012-02-03 | 2015-01-07 | 暨明医药科技（苏州）有限公司 | N,n-二烯丙基-(1r, 2r)-2-胺甲基-1-(2-噻吩)环丙烷酰胺盐酸盐的制备方法 |
| 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 |
| JP2015534464A (ja) | 2012-10-09 | 2015-12-03 | カリフォルニア インスティチュート オブ テクノロジー | ヘム酵素によって触媒されるインビボおよびインビトロオレフィンシクロプロパン化 |
| FR2998892B1 (fr) * | 2012-12-04 | 2015-01-02 | Pf Medicament | Derives d'aminocyclobutane, leur procede de preparation et leur utilisation a titre de medicaments |
| CN103613513B (zh) * | 2013-12-09 | 2016-01-20 | 上海现代制药股份有限公司 | 盐酸米那普仑中间体及其制备方法和应用 |
| US9399762B2 (en) | 2014-02-18 | 2016-07-26 | California Institute Of Technology | Methods and systems for sulfimidation or sulfoximidation of organic molecules |
| 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 |
| US10131624B2 (en) | 2014-11-04 | 2018-11-20 | 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 (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 |
-
1985
- 1985-04-25 FR FR8506335A patent/FR2581059B1/fr not_active Expired
-
1986
- 1986-04-14 GR GR860980A patent/GR860980B/el unknown
- 1986-04-17 AU AU56343/86A patent/AU587613B2/en not_active Expired
- 1986-04-18 ZA ZA862929A patent/ZA862929B/xx unknown
- 1986-04-21 IE IE105786A patent/IE59015B1/en not_active IP Right Cessation
- 1986-04-22 NO NO861573A patent/NO165143C/no unknown
- 1986-04-22 DE DE8686400873T patent/DE3662877D1/de not_active Expired
- 1986-04-22 EP EP86400873A patent/EP0200638B1/fr not_active Expired
- 1986-04-22 YU YU655/86A patent/YU44915B/xx unknown
- 1986-04-22 AT AT86400873T patent/ATE42273T1/de not_active IP Right Cessation
- 1986-04-23 KR KR1019860003133A patent/KR940006764B1/ko not_active Expired - Lifetime
- 1986-04-23 CA CA000507320A patent/CA1266486A/fr not_active Expired - Lifetime
- 1986-04-24 SU SU864027356A patent/SU1443797A3/ru active
- 1986-04-24 ES ES554321A patent/ES8704449A1/es not_active Expired
- 1986-04-24 MX MX2307A patent/MX162896B/es unknown
- 1986-04-24 JP JP61095850A patent/JPS61251650A/ja active Granted
- 1986-04-24 HU HU861711A patent/HU195182B/hu unknown
- 1986-04-24 PT PT82461A patent/PT82461B/pt unknown
- 1986-04-24 DK DK191286A patent/DK170888B1/da not_active IP Right Cessation
- 1986-04-25 AR AR30375986A patent/AR240695A1/es active
- 1986-04-25 FI FI861755A patent/FI87196C/fi not_active IP Right Cessation
- 1986-04-25 OA OA58846A patent/OA08241A/xx unknown
-
1993
- 1993-03-04 GE GEAP1993566A patent/GEP19970789B/en unknown
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