CZ304602B6 - Způsob krystalizace hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (hydrochloridu duloxetinu) - Google Patents
Způsob krystalizace hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (hydrochloridu duloxetinu) Download PDFInfo
- Publication number
- CZ304602B6 CZ304602B6 CZ2009-584A CZ2009584A CZ304602B6 CZ 304602 B6 CZ304602 B6 CZ 304602B6 CZ 2009584 A CZ2009584 A CZ 2009584A CZ 304602 B6 CZ304602 B6 CZ 304602B6
- Authority
- CZ
- Czechia
- Prior art keywords
- duloxetine hydrochloride
- solvent
- crystalline duloxetine
- crystalline
- crystals
- Prior art date
Links
- 229960002496 duloxetine hydrochloride Drugs 0.000 title claims abstract description 86
- 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 86
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002425 crystallisation Methods 0.000 title claims abstract description 26
- 230000008025 crystallization Effects 0.000 title claims abstract description 26
- BFFSMCNJSOPUAY-LMOVPXPDSA-N (S)-duloxetine hydrochloride Chemical compound Cl.C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 BFFSMCNJSOPUAY-LMOVPXPDSA-N 0.000 title description 2
- 239000013078 crystal Substances 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 239000003586 protic polar solvent Substances 0.000 claims abstract description 18
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 11
- 239000011877 solvent mixture Substances 0.000 claims abstract description 9
- 150000002576 ketones Chemical class 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 238000005259 measurement Methods 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 9
- 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 8
- 238000001816 cooling Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 229960002866 duloxetine Drugs 0.000 claims description 7
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 4
- 229940067606 lecithin Drugs 0.000 claims description 4
- 235000010445 lecithin Nutrition 0.000 claims description 4
- 239000000787 lecithin Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- RFAZFSACZIVZDV-UHFFFAOYSA-N butan-2-one Chemical compound CCC(C)=O.CCC(C)=O RFAZFSACZIVZDV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000000527 sonication Methods 0.000 claims 3
- 230000003111 delayed effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 abstract description 10
- 150000002148 esters Chemical class 0.000 abstract description 3
- 239000002245 particle Substances 0.000 description 46
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 17
- 238000009826 distribution Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- JFTURWWGPMTABQ-SFHVURJKSA-N (3s)-n,n-dimethyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCN(C)C)=CC=CS1 JFTURWWGPMTABQ-SFHVURJKSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000000877 morphologic effect Effects 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- PDRNJKDODQMLSW-HZVMSULOSA-N N[C@@H](CCCNC(N)=N)C(O)=O.N[C@@H](CCCNC(N)=N)C(O)=O.Nc1nc2[nH]cc(CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)c2c(=O)[nH]1 Chemical compound N[C@@H](CCCNC(N)=N)C(O)=O.N[C@@H](CCCNC(N)=N)C(O)=O.Nc1nc2[nH]cc(CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)c2c(=O)[nH]1 PDRNJKDODQMLSW-HZVMSULOSA-N 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ZEUITGRIYCTCEM-UHFFFAOYSA-N duloxetine Chemical compound C=1C=CC2=CC=CC=C2C=1OC(CCNC)C1=CC=CS1 ZEUITGRIYCTCEM-UHFFFAOYSA-N 0.000 description 1
- BFFSMCNJSOPUAY-UHFFFAOYSA-N duloxetine hydrochloride Chemical compound Cl.C=1C=CC2=CC=CC=C2C=1OC(CCNC)C1=CC=CS1 BFFSMCNJSOPUAY-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005406 washing 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
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2009-584A CZ304602B6 (cs) | 2009-09-02 | 2009-09-02 | Způsob krystalizace hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (hydrochloridu duloxetinu) |
| EA201290127A EA021528B1 (ru) | 2009-09-02 | 2010-09-02 | Способ кристаллизации (s)-n-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина гидрохлорида (дулоксетина) |
| EP10771629A EP2473497A1 (en) | 2009-09-02 | 2010-09-02 | A method of crystallization of (s)-n-methyl-3-(1-naphthyloxy)-3- (2-thienyl)propylamine hydrochloride (duloxetine) |
| PCT/CZ2010/000099 WO2011026449A1 (en) | 2009-09-02 | 2010-09-02 | A method of crystallization of (s)-n-methyl-3-(1-naphthyloxy)-3- (2-thienyl)propylamine hydrochloride (duloxetine) |
| MX2012002621A MX2012002621A (es) | 2009-09-02 | 2010-09-02 | Un metodo de cristalizacion de clorhidrato de (s)-n-metil-3-(1-naftiloxi)-3-(2-tienil)propilamina (duloxetina). |
| CN2010800392370A CN102482254A (zh) | 2009-09-02 | 2010-09-02 | (s)-n-甲基-3-(1-萘氧基)-3-(2-噻吩基)丙胺盐酸盐(度洛西汀)的结晶方法 |
| KR1020127004225A KR20120047262A (ko) | 2009-09-02 | 2010-09-02 | (ｓ)-ｎ-메틸-3-(1-나프틸옥시)-3-(2-티에닐)프로필아민 하이드로클로라이드(듀록세틴)의 결정화 방법 |
| BR112012004862A BR112012004862A2 (pt) | 2009-09-02 | 2010-09-02 | método para a preparação de um composto , duloxetina cristalina, e, composição farmacêutica |
| JP2012527196A JP2013503823A (ja) | 2009-09-02 | 2010-09-02 | （ｓ）‐ｎ‐メチル‐３‐（１‐ナフチルオキシ）‐３‐（２‐チエニル）プロピルアミン塩酸塩（デュロキセチン）の結晶化方法 |
| IL218329A IL218329A0 (en) | 2009-09-02 | 2012-02-27 | A method of crystallization of (s)-n-methyl-3-(1-naphthyloxy)-3- (2-thienyl)propylamine hydrochloride (duloxetine) |
| ZA2012/01570A ZA201201570B (en) | 2009-09-02 | 2012-03-01 | A method of crystallization of (s)-n-methyl-3-1(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (duloxetine) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2009-584A CZ304602B6 (cs) | 2009-09-02 | 2009-09-02 | Způsob krystalizace hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (hydrochloridu duloxetinu) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ2009584A3 CZ2009584A3 (cs) | 2011-03-09 |
| CZ304602B6 true CZ304602B6 (cs) | 2014-07-30 |
Family
ID=43413356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ2009-584A CZ304602B6 (cs) | 2009-09-02 | 2009-09-02 | Způsob krystalizace hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (hydrochloridu duloxetinu) |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2473497A1 (enExample) |
| JP (1) | JP2013503823A (enExample) |
| KR (1) | KR20120047262A (enExample) |
| CN (1) | CN102482254A (enExample) |
| BR (1) | BR112012004862A2 (enExample) |
| CZ (1) | CZ304602B6 (enExample) |
| EA (1) | EA021528B1 (enExample) |
| IL (1) | IL218329A0 (enExample) |
| MX (1) | MX2012002621A (enExample) |
| WO (1) | WO2011026449A1 (enExample) |
| ZA (1) | ZA201201570B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060276660A1 (en) * | 2005-03-14 | 2006-12-07 | Santiago Ini | Process for the purification of duloxetine hydrochloride |
| WO2007093439A1 (en) * | 2006-02-17 | 2007-08-23 | Krka | Processes for the preparation of crystalline forms of duloxetine hydrochloride |
| WO2007148096A1 (en) * | 2006-06-23 | 2007-12-27 | Arrow International Limited | Crystalline duloxetine hydrochloride |
| WO2008107911A2 (en) * | 2007-03-05 | 2008-09-12 | Lupin Limited | Novel process for preparation of duloxetine hydrochloride |
| CZ300116B6 (cs) * | 2006-12-05 | 2009-02-11 | Zentiva, A. S. | Zpusob cištení hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR880007433A (ko) | 1986-12-22 | 1988-08-27 | 메리 앤 터커 | 3-아릴옥시-3-치환된 프로판아민 |
| US5362886A (en) | 1993-10-12 | 1994-11-08 | Eli Lilly And Company | Asymmetric synthesis |
| DE10212301A1 (de) | 2002-03-20 | 2003-10-02 | Bayer Ag | Verfahren zur Herstellung von Aryl-aminopropanolen |
| DK1539673T3 (da) | 2002-07-09 | 2008-01-21 | Lonza Ag | Fremgangsmåde til fremstilling af N-monosubstituerede beta-aminoalkoholer |
| GB0410470D0 (en) | 2004-05-11 | 2004-06-16 | Cipla Ltd | Pharmaceutical compound and polymorphs thereof |
| 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) |
| GB0612509D0 (en) * | 2006-06-23 | 2006-08-02 | Arrow Int Ltd | Crystalline duloxetine hydrochloride |
-
2009
- 2009-09-02 CZ CZ2009-584A patent/CZ304602B6/cs not_active IP Right Cessation
-
2010
- 2010-09-02 KR KR1020127004225A patent/KR20120047262A/ko not_active Withdrawn
- 2010-09-02 CN CN2010800392370A patent/CN102482254A/zh active Pending
- 2010-09-02 BR BR112012004862A patent/BR112012004862A2/pt not_active IP Right Cessation
- 2010-09-02 WO PCT/CZ2010/000099 patent/WO2011026449A1/en not_active Ceased
- 2010-09-02 EP EP10771629A patent/EP2473497A1/en not_active Withdrawn
- 2010-09-02 MX MX2012002621A patent/MX2012002621A/es not_active Application Discontinuation
- 2010-09-02 EA EA201290127A patent/EA021528B1/ru not_active IP Right Cessation
- 2010-09-02 JP JP2012527196A patent/JP2013503823A/ja active Pending
-
2012
- 2012-02-27 IL IL218329A patent/IL218329A0/en unknown
- 2012-03-01 ZA ZA2012/01570A patent/ZA201201570B/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060276660A1 (en) * | 2005-03-14 | 2006-12-07 | Santiago Ini | Process for the purification of duloxetine hydrochloride |
| WO2007093439A1 (en) * | 2006-02-17 | 2007-08-23 | Krka | Processes for the preparation of crystalline forms of duloxetine hydrochloride |
| WO2007148096A1 (en) * | 2006-06-23 | 2007-12-27 | Arrow International Limited | Crystalline duloxetine hydrochloride |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2473497A1 (en) | 2012-07-11 |
| BR112012004862A2 (pt) | 2015-09-08 |
| JP2013503823A (ja) | 2013-02-04 |
| ZA201201570B (en) | 2013-08-28 |
| MX2012002621A (es) | 2012-07-03 |
| IL218329A0 (en) | 2012-04-30 |
| WO2011026449A1 (en) | 2011-03-10 |
| EA201290127A1 (ru) | 2013-02-28 |
| CZ2009584A3 (cs) | 2011-03-09 |
| CN102482254A (zh) | 2012-05-30 |
| EA021528B1 (ru) | 2015-07-30 |
| KR20120047262A (ko) | 2012-05-11 |
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