JP2009541291A - 結晶塩酸デュロキセチン - Google Patents
結晶塩酸デュロキセチン Download PDFInfo
- Publication number
- JP2009541291A JP2009541291A JP2009515961A JP2009515961A JP2009541291A JP 2009541291 A JP2009541291 A JP 2009541291A JP 2009515961 A JP2009515961 A JP 2009515961A JP 2009515961 A JP2009515961 A JP 2009515961A JP 2009541291 A JP2009541291 A JP 2009541291A
- 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
- 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 title claims abstract description 95
- 229960002496 duloxetine hydrochloride Drugs 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 claims abstract description 93
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000000243 solution Substances 0.000 claims description 127
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 111
- 239000003960 organic solvent Substances 0.000 claims description 95
- 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 description 58
- 229960002866 duloxetine Drugs 0.000 claims description 57
- 239000012044 organic layer Substances 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 18
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 16
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 235000019270 ammonium chloride Nutrition 0.000 claims description 14
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 11
- -1 heterocyclic organic compound Chemical class 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 6
- 206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 6
- 238000002441 X-ray diffraction Methods 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 208000004296 neuralgia Diseases 0.000 claims description 6
- 208000021722 neuropathic pain Diseases 0.000 claims description 6
- 208000007848 Alcoholism Diseases 0.000 claims description 5
- 208000000044 Amnesia Diseases 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 208000026139 Memory disease Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 201000007930 alcohol dependence Diseases 0.000 claims description 5
- 230000001668 ameliorated effect Effects 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- 230000006984 memory degeneration Effects 0.000 claims description 5
- 208000023060 memory loss Diseases 0.000 claims description 5
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims description 5
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 5
- 230000000391 smoking effect Effects 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000009738 saturating Methods 0.000 claims description 4
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- 238000001757 thermogravimetry curve Methods 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 1
- 239000007854 depigmenting agent Substances 0.000 claims 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940076279 serotonin Drugs 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 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
- 150000001875 compounds Chemical class 0.000 description 1
- 229940029644 cymbalta Drugs 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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 true JP2009541291A (ja) | 2009-11-26 |
| JP2009541291A5 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 |
| US8278463B2 (en) | 2008-04-04 | 2012-10-02 | 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005108386A1 (en) * | 2004-05-11 | 2005-11-17 | Cipla Limited | Crystalline forms of duloxetine free base |
| 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 |
Family Cites Families (13)
| 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 |
| AU2003263585A1 (en) | 2003-08-25 | 2005-03-10 | 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 |
| 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 |
| US20060270859A1 (en) * | 2005-01-27 | 2006-11-30 | Santiago Ini | Duloxetine HCl polymorphs |
| US7534900B2 (en) | 2005-03-14 | 2009-05-19 | Teva Pharmaceutical Industries Ltd | Process for the purification of duloxetine hydrochloride |
| EP1976844A4 (en) * | 2006-01-06 | 2010-11-03 | Msn Lab Ltd | IMPROVED METHOD FOR PURE DULOXETIN 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
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2007
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- 2007-06-21 AU AU2007262800A patent/AU2007262800A1/en not_active Abandoned
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- 2007-06-21 CA CA002655991A patent/CA2655991A1/en not_active Abandoned
- 2007-06-21 JP JP2009515961A patent/JP2009541291A/ja active Pending
- 2007-06-21 EP EP07733320A patent/EP2049512A2/en not_active Withdrawn
- 2007-06-21 WO PCT/GB2007/002324 patent/WO2007148102A2/en not_active Ceased
- 2007-06-21 CN CN200780023170A patent/CN101631783A/zh active Pending
- 2007-06-21 BR BRPI0712372-8A patent/BRPI0712372A2/pt not_active IP Right Cessation
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005108386A1 (en) * | 2004-05-11 | 2005-11-17 | Cipla Limited | Crystalline forms of duloxetine free base |
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| JPN5009008506; ＳＹＮＴＨＯＮ ＢＶ: ＲＥＳＥＡＲＣＨ ＤＩＳＣＬＯＳＵＲＥ Ｖ．ＤＮ４９８０１１, 200510, ｐ．１１２９-１１３２, ＭＡＳＯＮ ＰＵＢＬＩＣＡＴＩＯＮＳ * |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ572919A (en) | 2012-01-12 |
| EP2049512A2 (en) | 2009-04-22 |
| GB0612509D0 (en) | 2006-08-02 |
| CN101631783A (zh) | 2010-01-20 |
| WO2007148102A2 (en) | 2007-12-27 |
| US7795455B2 (en) | 2010-09-14 |
| AU2007262800A1 (en) | 2007-12-27 |
| CA2655991A1 (en) | 2007-12-27 |
| US20080021091A1 (en) | 2008-01-24 |
| GB0700830D0 (en) | 2007-02-21 |
| WO2007148102A3 (en) | 2008-03-13 |
| BRPI0712372A2 (pt) | 2012-06-12 |
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