AU2007262801B2 - Crystalline duloxetine hydrochloride - Google Patents
Crystalline duloxetine hydrochloride Download PDFInfo
- Publication number
- AU2007262801B2 AU2007262801B2 AU2007262801A AU2007262801A AU2007262801B2 AU 2007262801 B2 AU2007262801 B2 AU 2007262801B2 AU 2007262801 A AU2007262801 A AU 2007262801A AU 2007262801 A AU2007262801 A AU 2007262801A AU 2007262801 B2 AU2007262801 B2 AU 2007262801B2
- Authority
- AU
- Australia
- Prior art keywords
- organic solvent
- duloxetine
- solution
- duloxetine hydrochloride
- crystalline
- 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.)
- Ceased
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 50
- 229960002496 duloxetine hydrochloride Drugs 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 39
- 229960002866 duloxetine Drugs 0.000 claims description 26
- 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 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 7
- 206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 7
- 230000001668 ameliorated effect Effects 0.000 claims description 7
- 208000007848 Alcoholism Diseases 0.000 claims description 6
- 208000000044 Amnesia Diseases 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 201000007930 alcohol dependence Diseases 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 231100000863 loss of memory Toxicity 0.000 claims description 6
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims description 6
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims description 6
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 6
- 230000000391 smoking effect Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- -1 C 6 ester Chemical class 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 3
- 229940079593 drug Drugs 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
- 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
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 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
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000012058 sterile packaged powder 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
- 238000001757 thermogravimetry curve Methods 0.000 description 1
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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0612506.6 | 2006-06-23 | ||
| GBGB0612506.6A GB0612506D0 (en) | 2006-06-23 | 2006-06-23 | Crystalline duloxetine hydrochloride |
| PCT/GB2007/002325 WO2007148103A1 (en) | 2006-06-23 | 2007-06-21 | Crystalline duloxetine hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2007262801A1 AU2007262801A1 (en) | 2007-12-27 |
| AU2007262801B2 true AU2007262801B2 (en) | 2013-01-31 |
Family
ID=36803801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007262801A Ceased AU2007262801B2 (en) | 2006-06-23 | 2007-06-21 | Crystalline duloxetine hydrochloride |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7799935B2 (enExample) |
| EP (1) | EP2035404A1 (enExample) |
| JP (1) | JP2009541292A (enExample) |
| CN (1) | CN101627026A (enExample) |
| AU (1) | AU2007262801B2 (enExample) |
| BR (1) | BRPI0711954A2 (enExample) |
| CA (1) | CA2656035A1 (enExample) |
| GB (1) | GB0612506D0 (enExample) |
| NZ (1) | NZ573212A (enExample) |
| WO (1) | WO2007148103A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0612506D0 (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 |
| CA2754141A1 (en) | 2009-03-13 | 2010-09-16 | Alembic Pharmaceuticals Limited | A process for the preparation of duloxetine hydrochloride |
| 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 |
| CN106265528A (zh) * | 2015-05-12 | 2017-01-04 | 法德生技药品股份有限公司 | 制备药物凝集体的方法 |
| JP2016222628A (ja) * | 2015-06-03 | 2016-12-28 | 株式会社トクヤマ | デュロキセチン塩酸塩の製造方法 |
| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006081515A2 (en) * | 2005-01-27 | 2006-08-03 | Teva Pharmaceutical Industries Ltd. | Duloxetine hydrochloride polymorphs |
Family Cites Families (10)
| 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 |
| GB0410470D0 (en) * | 2004-05-11 | 2004-06-16 | Cipla Ltd | Pharmaceutical compound and polymorphs thereof |
| 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 |
| 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 |
| GB0612506D0 (en) | 2006-06-23 | 2006-08-02 | Arrow Int Ltd | Crystalline duloxetine hydrochloride |
-
2006
- 2006-06-23 GB GBGB0612506.6A patent/GB0612506D0/en not_active Ceased
-
2007
- 2007-06-21 CN CN200780023171A patent/CN101627026A/zh active Pending
- 2007-06-21 JP JP2009515962A patent/JP2009541292A/ja active Pending
- 2007-06-21 NZ NZ573212A patent/NZ573212A/en not_active IP Right Cessation
- 2007-06-21 CA CA002656035A patent/CA2656035A1/en not_active Abandoned
- 2007-06-21 WO PCT/GB2007/002325 patent/WO2007148103A1/en not_active Ceased
- 2007-06-21 EP EP07733321A patent/EP2035404A1/en not_active Withdrawn
- 2007-06-21 BR BRPI0711954-2A patent/BRPI0711954A2/pt not_active IP Right Cessation
- 2007-06-21 AU AU2007262801A patent/AU2007262801B2/en not_active Ceased
- 2007-06-22 US US11/821,278 patent/US7799935B2/en not_active Expired - Fee Related
-
2010
- 2010-09-10 US US12/879,616 patent/US8093407B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006081515A2 (en) * | 2005-01-27 | 2006-08-03 | Teva Pharmaceutical Industries Ltd. | Duloxetine hydrochloride polymorphs |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007148103A1 (en) | 2007-12-27 |
| BRPI0711954A2 (pt) | 2011-12-20 |
| GB0612506D0 (en) | 2006-08-02 |
| US20100331388A1 (en) | 2010-12-30 |
| CN101627026A (zh) | 2010-01-13 |
| EP2035404A1 (en) | 2009-03-18 |
| CA2656035A1 (en) | 2007-12-27 |
| NZ573212A (en) | 2012-01-12 |
| US8093407B2 (en) | 2012-01-10 |
| US7799935B2 (en) | 2010-09-21 |
| US20080021089A1 (en) | 2008-01-24 |
| AU2007262801A1 (en) | 2007-12-27 |
| JP2009541292A (ja) | 2009-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |