JP5247687B2 - 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
- JP5247687B2 JP5247687B2 JP2009515959A JP2009515959A JP5247687B2 JP 5247687 B2 JP5247687 B2 JP 5247687B2 JP 2009515959 A JP2009515959 A JP 2009515959A JP 2009515959 A JP2009515959 A JP 2009515959A JP 5247687 B2 JP5247687 B2 JP 5247687B2
- Authority
- JP
- Japan
- Prior art keywords
- duloxetine
- solution
- organic solvent
- duloxetine hydrochloride
- crystallized
- 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.)
- Expired - Fee Related
Links
- 229960002496 duloxetine hydrochloride Drugs 0.000 title claims description 43
- 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 description 43
- 239000000243 solution Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
- 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 26
- 229960002866 duloxetine Drugs 0.000 claims description 25
- 239000003960 organic solvent Substances 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
- -1 C 6 ester Chemical class 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 206010066218 Stress Urinary Incontinence Diseases 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 208000004296 neuralgia Diseases 0.000 description 4
- 208000021722 neuropathic pain Diseases 0.000 description 4
- 208000007848 Alcoholism Diseases 0.000 description 3
- 208000000044 Amnesia Diseases 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- 208000026139 Memory disease Diseases 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- 201000007930 alcohol dependence Diseases 0.000 description 3
- 230000001668 ameliorated effect Effects 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000006984 memory degeneration Effects 0.000 description 3
- 208000023060 memory loss Diseases 0.000 description 3
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 3
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 229940076279 serotonin Drugs 0.000 description 3
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 3
- 230000000391 smoking effect Effects 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
- 239000000969 carrier Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 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
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000007787 solid 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
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003158 alcohol group 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
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940029644 cymbalta Drugs 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
- 239000012458 free base 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
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 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
- 238000001228 spectrum Methods 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
- 238000001757 thermogravimetry curve Methods 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (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 |
|---|---|---|---|
| GB0612508.2 | 2006-06-23 | ||
| GBGB0612508.2A GB0612508D0 (en) | 2006-06-23 | 2006-06-23 | Crystalline duloxetine hydrochloride |
| PCT/GB2007/002317 WO2007148096A1 (en) | 2006-06-23 | 2007-06-21 | Crystalline duloxetine hydrochloride |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009541290A JP2009541290A (ja) | 2009-11-26 |
| JP2009541290A5 JP2009541290A5 (OSRAM) | 2010-05-13 |
| JP5247687B2 true JP5247687B2 (ja) | 2013-07-24 |
Family
ID=36803803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009515959A Expired - Fee Related JP5247687B2 (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) | US7795454B2 (OSRAM) |
| EP (1) | EP2035403A1 (OSRAM) |
| JP (1) | JP5247687B2 (OSRAM) |
| CN (1) | CN101595099B (OSRAM) |
| AU (1) | AU2007262794B2 (OSRAM) |
| BR (1) | BRPI0712454A2 (OSRAM) |
| CA (1) | CA2655962A1 (OSRAM) |
| GB (1) | GB0612508D0 (OSRAM) |
| NZ (1) | NZ572918A (OSRAM) |
| WO (1) | WO2007148096A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0612508D0 (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) |
| 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 |
| JP6178817B2 (ja) * | 2015-04-27 | 2017-08-09 | 株式会社豊田中央研究所 | 光輝性塗料組成物、光輝性樹脂膜、及び、積層塗膜 |
| 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 |
| JP7491934B2 (ja) | 2019-01-03 | 2024-05-28 | ディーエヌエー スクリプト | オリゴヌクレオチドセットのワンポット合成 |
| 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 (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 |
| 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 |
| WO2006071868A2 (en) * | 2004-12-23 | 2006-07-06 | Teva Pharmaceutical Industries Ltd. | Process for preparing pharmaceutically acceptable salts of duloxetine and intermediates thereof |
| WO2006081515A2 (en) * | 2005-01-27 | 2006-08-03 | Teva Pharmaceutical Industries Ltd. | Duloxetine hydrochloride polymorphs |
| TW200639161A (en) | 2005-03-14 | 2006-11-16 | Teva Pharma | Process for the purification of 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 |
| GB0612508D0 (en) | 2006-06-23 | 2006-08-02 | Arrow Int Ltd | Crystalline duloxetine hydrochloride |
-
2006
- 2006-06-23 GB GBGB0612508.2A patent/GB0612508D0/en not_active Ceased
-
2007
- 2007-06-21 CN CN2007800231697A patent/CN101595099B/zh not_active Expired - Fee Related
- 2007-06-21 CA CA002655962A patent/CA2655962A1/en not_active Abandoned
- 2007-06-21 WO PCT/GB2007/002317 patent/WO2007148096A1/en not_active Ceased
- 2007-06-21 JP JP2009515959A patent/JP5247687B2/ja not_active Expired - Fee Related
- 2007-06-21 AU AU2007262794A patent/AU2007262794B2/en not_active Ceased
- 2007-06-21 EP EP07733313A patent/EP2035403A1/en not_active Withdrawn
- 2007-06-21 BR BRPI0712454-6A patent/BRPI0712454A2/pt not_active IP Right Cessation
- 2007-06-21 NZ NZ572918A patent/NZ572918A/en not_active IP Right Cessation
- 2007-06-22 US US11/821,290 patent/US7795454B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101595099A (zh) | 2009-12-02 |
| JP2009541290A (ja) | 2009-11-26 |
| AU2007262794A1 (en) | 2007-12-27 |
| CN101595099B (zh) | 2013-03-06 |
| US20080021090A1 (en) | 2008-01-24 |
| EP2035403A1 (en) | 2009-03-18 |
| CA2655962A1 (en) | 2007-12-27 |
| GB0612508D0 (en) | 2006-08-02 |
| NZ572918A (en) | 2011-12-22 |
| WO2007148096A1 (en) | 2007-12-27 |
| BRPI0712454A2 (pt) | 2012-10-02 |
| US7795454B2 (en) | 2010-09-14 |
| AU2007262794B2 (en) | 2012-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5247687B2 (ja) | 結晶塩酸デュロキセチン | |
| CN101440079B (zh) | 制备外消旋西酞普兰和/或s-或r-西酞普兰的方法 | |
| JP2009541292A (ja) | 結晶塩酸デュロキセチン | |
| WO2008062460A2 (en) | Crystalline forms of pregabalin | |
| JP2009541291A (ja) | 結晶塩酸デュロキセチン | |
| WO2007119114A2 (en) | Improved synthesis and preparations of duloxetine salts | |
| JP2009541291A5 (OSRAM) | ||
| EP2358369A1 (en) | Process for the preparation of substantially optically pure repaglinide and precursors thereof | |
| US20100261775A1 (en) | Polymorphic form of duloxetine hydrochloride | |
| WO2009080469A1 (en) | Process for the preparation of clopidogrel bisulphate form i | |
| WO2009118758A2 (en) | Novel crystalline forms of desvenlafaxine succinate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100326 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100326 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20110119 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20110216 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121023 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130122 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130129 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130222 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130319 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130409 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20160419 Year of fee payment: 3 |
|
| LAPS | Cancellation because of no payment of annual fees |