JP2009541291A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009541291A5 JP2009541291A5 JP2009515961A JP2009515961A JP2009541291A5 JP 2009541291 A5 JP2009541291 A5 JP 2009541291A5 JP 2009515961 A JP2009515961 A JP 2009515961A JP 2009515961 A JP2009515961 A JP 2009515961A JP 2009541291 A5 JP2009541291 A5 JP 2009541291A5
- Authority
- JP
- Japan
- Prior art keywords
- solution
- organic solvent
- organic
- duloxetine
- duloxetine hydrochloride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 68
- 239000000243 solution Substances 0.000 claims 54
- 239000003960 organic solvent Substances 0.000 claims 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 36
- JFTURWWGPMTABQ-UHFFFAOYSA-N n,n-dimethyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1OC(CCN(C)C)C1=CC=CS1 JFTURWWGPMTABQ-UHFFFAOYSA-N 0.000 claims 35
- 229960002496 duloxetine hydrochloride Drugs 0.000 claims 34
- 239000012044 organic layer Substances 0.000 claims 24
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 19
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 claims 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 18
- 229960002866 duloxetine Drugs 0.000 claims 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 235000019270 ammonium chloride Nutrition 0.000 claims 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 6
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 238000001035 drying Methods 0.000 claims 6
- 238000002156 mixing Methods 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 239000012458 free base Substances 0.000 claims 5
- 239000010410 layer Substances 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 4
- 238000005406 washing Methods 0.000 claims 4
- -1 C 6 ester Chemical class 0.000 claims 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002148 esters Chemical group 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 238000009738 saturating Methods 0.000 claims 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 238000005292 vacuum distillation Methods 0.000 claims 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010066218 Stress Urinary Incontinence Diseases 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000006984 memory degeneration Effects 0.000 claims 1
- 208000023060 memory loss Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims 1
- 230000000391 smoking effect Effects 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0612509.0A GB0612509D0 (en) | 2006-06-23 | 2006-06-23 | Crystalline duloxetine hydrochloride |
| GBGB0700830.3A GB0700830D0 (en) | 2006-06-23 | 2007-01-16 | Crystalline duloxetine hydrochloride |
| PCT/GB2007/002324 WO2007148102A2 (en) | 2006-06-23 | 2007-06-21 | Crystalline duloxetine hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009541291A JP2009541291A (ja) | 2009-11-26 |
| JP2009541291A5 true JP2009541291A5 (enExample) | 2010-05-13 |
Family
ID=38510285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009515961A Pending JP2009541291A (ja) | 2006-06-23 | 2007-06-21 | 結晶塩酸デュロキセチン |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7795455B2 (enExample) |
| EP (1) | EP2049512A2 (enExample) |
| JP (1) | JP2009541291A (enExample) |
| CN (1) | CN101631783A (enExample) |
| AU (1) | AU2007262800A1 (enExample) |
| BR (1) | BRPI0712372A2 (enExample) |
| CA (1) | CA2655991A1 (enExample) |
| GB (2) | GB0612509D0 (enExample) |
| NZ (1) | NZ572919A (enExample) |
| WO (1) | WO2007148102A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0612509D0 (en) | 2006-06-23 | 2006-08-02 | Arrow Int Ltd | Crystalline duloxetine hydrochloride |
| EP2107057A1 (en) * | 2008-04-04 | 2009-10-07 | Ranbaxy Laboratories Limited | Process for the preparation of pure duloxetine hydrochloride |
| CZ304602B6 (cs) * | 2009-09-02 | 2014-07-30 | Zentiva, K. S. | Způsob krystalizace hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (hydrochloridu duloxetinu) |
| CN103172610B (zh) * | 2011-12-23 | 2015-11-25 | 石药集团中奇制药技术（石家庄）有限公司 | 一种盐酸度洛西汀的制备方法 |
| CN103626735A (zh) * | 2012-08-28 | 2014-03-12 | 石药集团中奇制药技术（石家庄）有限公司 | 一种盐酸度洛西汀晶型及其制备方法 |
| CN104478849A (zh) * | 2014-02-14 | 2015-04-01 | 广东东阳光药业有限公司 | 制备去甲肾上腺素再摄取双重抑制剂的方法 |
| CN113603673B (zh) * | 2020-11-16 | 2024-08-06 | 上海中西三维药业有限公司 | 一种盐酸度洛西汀的晶型、其制备方法及其应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4956388A (en) * | 1986-12-22 | 1990-09-11 | Eli Lilly And Company | 3-aryloxy-3-substituted propanamines |
| US5362886A (en) * | 1993-10-12 | 1994-11-08 | Eli Lilly And Company | Asymmetric synthesis |
| WO2005019199A1 (en) | 2003-08-25 | 2005-03-03 | Hetero Drugs Limited | Amorphous duloxetine hydrochloride |
| US20050197503A1 (en) * | 2004-03-05 | 2005-09-08 | Boehringer Ingelheim International Gmbh | Process for the preparation of N-alkyl-N-methyl-3-hydroxy-3-(2-thienyl)-propylamines |
| GB0410470D0 (en) * | 2004-05-11 | 2004-06-16 | Cipla Ltd | Pharmaceutical compound and polymorphs thereof |
| US7550605B2 (en) | 2004-08-05 | 2009-06-23 | Sun Pharmaceutical Industries Ltd. | Process for preparation of an anitdepressant compound |
| CZ297560B6 (cs) | 2004-10-26 | 2007-02-07 | Zentiva, A. S. | Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (duloxetinu) |
| EP1812428A2 (en) | 2004-11-19 | 2007-08-01 | Teva Pharmaceutical Industries Ltd | Zolmitriptan crystal forms |
| WO2006058121A1 (en) | 2004-11-23 | 2006-06-01 | Bristol-Myers Squibb Company | Crystalline forms of 3'-tert-butyl-3'-n-tert-butyloxycarbonyl-4-deacetyl-3'-dephenyl-3'-n-debenzoyl-4-o-methoxycarbonyl-paclitaxel |
| JP2007523213A (ja) * | 2004-12-23 | 2007-08-16 | テバ ファーマシューティカル インダストリーズ リミティド | 医薬的に許容できるデュロキセチンの塩及びその中間体の調製方法 |
| EP1776049A2 (en) * | 2005-01-27 | 2007-04-25 | Teva Pharmaceutical Industries Ltd. | Duloxetine hcl polymorphs |
| CA2599475A1 (en) | 2005-03-14 | 2006-09-21 | Teva Pharmaceutical Industries Ltd. | Pure duloxetine hydrochloride |
| WO2007077580A2 (en) * | 2006-01-06 | 2007-07-12 | Msn Laboratories Limited | Improved process for pure duloxetine hydrochloride |
| EP1820800A1 (en) * | 2006-02-17 | 2007-08-22 | KRKA, tovarna zdravil, d.d., Novo mesto | Crystalline forms of duloxetine hydrochloride and processes for their preparation |
| GB0612509D0 (en) | 2006-06-23 | 2006-08-02 | Arrow Int Ltd | Crystalline duloxetine hydrochloride |
-
2006
- 2006-06-23 GB GBGB0612509.0A patent/GB0612509D0/en not_active Ceased
-
2007
- 2007-01-16 GB GBGB0700830.3A patent/GB0700830D0/en not_active Ceased
- 2007-06-21 NZ NZ572919A patent/NZ572919A/en not_active IP Right Cessation
- 2007-06-21 CA CA002655991A patent/CA2655991A1/en not_active Abandoned
- 2007-06-21 JP JP2009515961A patent/JP2009541291A/ja active Pending
- 2007-06-21 BR BRPI0712372-8A patent/BRPI0712372A2/pt not_active IP Right Cessation
- 2007-06-21 CN CN200780023170A patent/CN101631783A/zh active Pending
- 2007-06-21 EP EP07733320A patent/EP2049512A2/en not_active Withdrawn
- 2007-06-21 AU AU2007262800A patent/AU2007262800A1/en not_active Abandoned
- 2007-06-21 WO PCT/GB2007/002324 patent/WO2007148102A2/en not_active Ceased
- 2007-06-22 US US11/821,460 patent/US7795455B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009541291A5 (enExample) | ||
| JP6386171B2 (ja) | 新規なアミノアルキルベンゾチアゼピン誘導体及びその用途 | |
| CN101993406B (zh) | 光学活性的吲哚啉化合物及其制备方法 | |
| CN102762535B (zh) | 合成和分离n-(溴乙酰基)-3, 3-二硝基氮杂环丁烷的方法和包括其的组合物 | |
| CN101440079B (zh) | 制备外消旋西酞普兰和/或s-或r-西酞普兰的方法 | |
| JP5247687B2 (ja) | 結晶塩酸デュロキセチン | |
| JP2009541292A5 (enExample) | ||
| JP5390617B2 (ja) | アデホビルジピボキシルの精製方法 | |
| JP2009541290A5 (enExample) | ||
| JP2009541291A (ja) | 結晶塩酸デュロキセチン | |
| JP2009541292A (ja) | 結晶塩酸デュロキセチン | |
| CN108947989B (zh) | 氘代光学异构体及其医药用途 | |
| CN100379736C (zh) | 恩替卡韦的制备方法 | |
| FR2959509A1 (fr) | Phase precurseur et son utilisation pour preparer le sel de magnesium tetrahydrate d'un enantiomere d'omeprazole | |
| CN105152954B (zh) | 一种无溶剂回收3-异丁基戊二酸单酰胺的方法 | |
| WO2006024890A1 (en) | Improved process for rabeprazole sodium in amorphous form | |
| CN101514163B (zh) | 光学纯西布曲明及其衍生盐的制备工艺 | |
| WO2015137407A1 (ja) | ヘテロアリールカルボン酸エステル誘導体の製造方法、その製造中間体及び結晶 | |
| CN102827080A (zh) | 一种伊伐布雷定新的合成方法及其新的中间产物 | |
| CN112645829B (zh) | 麻黄碱关键中间体(s)-2-甲胺基-1-苯基-1-丙酮的手性合成方法 | |
| CN110041294A (zh) | 2,2-二氯-n-[2-(2-呋喃基)-2-羟基乙基]乙酰胺的合成方法及其应用 | |
| US11111208B2 (en) | Process for the preparation of safinamide mesylate intermediate | |
| CN115232038A (zh) | 一种单氟一溴代亚磺酰亚胺衍生物及其制备与应用 | |
| CN120943795A (zh) | 一种n-(4-(叔丁基)噻唑-2-基)-3-氟苯甲酰胺的制备方法 | |
| WO1998003498A1 (fr) | Derives du thienylcyclohexane pour la synthese de thienylcyclohexyles |