EA021528B1 - Способ кристаллизации (s)-n-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина гидрохлорида (дулоксетина) - Google Patents
Способ кристаллизации (s)-n-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина гидрохлорида (дулоксетина) Download PDFInfo
- Publication number
- EA021528B1 EA021528B1 EA201290127A EA201290127A EA021528B1 EA 021528 B1 EA021528 B1 EA 021528B1 EA 201290127 A EA201290127 A EA 201290127A EA 201290127 A EA201290127 A EA 201290127A EA 021528 B1 EA021528 B1 EA 021528B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- duloxetine
- product
- crystalline
- crystalline duloxetine
- crystals
- Prior art date
Links
- 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 title claims abstract description 89
- 229960002866 duloxetine Drugs 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims description 36
- 238000002425 crystallisation Methods 0.000 title claims description 18
- 230000008025 crystallization Effects 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 9
- 239000003586 protic polar solvent Substances 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 239000011877 solvent mixture Substances 0.000 claims description 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 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
- -1 methyl-3- (1-naphthyloxy) -3- (2-thienyl) propylamine hydroxide Chemical compound 0.000 claims description 2
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims description 2
- 229940126569 noradrenaline reuptake inhibitor Drugs 0.000 claims description 2
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims description 2
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 abstract description 9
- 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 abstract 1
- 239000002245 particle Substances 0.000 description 48
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 39
- 239000000463 material Substances 0.000 description 17
- 238000009826 distribution Methods 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 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
- 239000002552 dosage form Substances 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007873 sieving Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 208000010201 Exanthema Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 201000005884 exanthem Diseases 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 206010037844 rash Diseases 0.000 description 2
- 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 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 239000002801 charged material Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000001000 micrograph Methods 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 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
- 238000010186 staining Methods 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)
Applications Claiming Priority (2)
| 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) |
| 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) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201290127A1 EA201290127A1 (ru) | 2013-02-28 |
| EA021528B1 true EA021528B1 (ru) | 2015-07-30 |
Family
ID=43413356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201290127A EA021528B1 (ru) | 2009-09-02 | 2010-09-02 | Способ кристаллизации (s)-n-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина гидрохлорида (дулоксетина) |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2473497A1 (cs) |
| JP (1) | JP2013503823A (cs) |
| KR (1) | KR20120047262A (cs) |
| CN (1) | CN102482254A (cs) |
| BR (1) | BR112012004862A2 (cs) |
| CZ (1) | CZ304602B6 (cs) |
| EA (1) | EA021528B1 (cs) |
| IL (1) | IL218329A0 (cs) |
| MX (1) | MX2012002621A (cs) |
| WO (1) | WO2011026449A1 (cs) |
| ZA (1) | ZA201201570B (cs) |
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 (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005108386A1 (en) * | 2004-05-11 | 2005-11-17 | Cipla Limited | Crystalline forms of duloxetine free base |
| WO2006045255A1 (en) * | 2004-10-26 | 2006-05-04 | Zentiva, A.S. | Method of manufacturing (s)-n-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (duloxetine) |
| WO2006099468A2 (en) * | 2005-03-14 | 2006-09-21 | Teva Pharmaceutical Industries Ltd. | 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 |
| WO2007148102A2 (en) * | 2006-06-23 | 2007-12-27 | Arrow International Limited | Crystalline duloxetine hydrochloride |
| WO2007148096A1 (en) * | 2006-06-23 | 2007-12-27 | Arrow International Limited | Crystalline duloxetine hydrochloride |
Family Cites Families (6)
| 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 |
| KR101027358B1 (ko) | 2002-07-09 | 2011-04-11 | 론자 아게 | Ｎ-일치환 β-아미노 알코올의 제조 방법 |
| CZ300116B6 (cs) * | 2006-12-05 | 2009-02-11 | Zentiva, A. S. | Zpusob cištení hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu |
| US8269023B2 (en) * | 2007-03-05 | 2012-09-18 | Lupin Ltd. | Process for preparation of duloxetine hydrochloride |
-
2009
- 2009-09-02 CZ CZ2009-584A patent/CZ304602B6/cs not_active IP Right Cessation
-
2010
- 2010-09-02 JP JP2012527196A patent/JP2013503823A/ja active Pending
- 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 EA EA201290127A patent/EA021528B1/ru not_active IP Right Cessation
- 2010-09-02 MX MX2012002621A patent/MX2012002621A/es not_active Application Discontinuation
- 2010-09-02 KR KR1020127004225A patent/KR20120047262A/ko not_active Withdrawn
- 2010-09-02 EP EP10771629A patent/EP2473497A1/en not_active Withdrawn
- 2010-09-02 WO PCT/CZ2010/000099 patent/WO2011026449A1/en active Application Filing
-
2012
- 2012-02-27 IL IL218329A patent/IL218329A0/en unknown
- 2012-03-01 ZA ZA2012/01570A patent/ZA201201570B/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005108386A1 (en) * | 2004-05-11 | 2005-11-17 | Cipla Limited | Crystalline forms of duloxetine free base |
| WO2006045255A1 (en) * | 2004-10-26 | 2006-05-04 | Zentiva, A.S. | Method of manufacturing (s)-n-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (duloxetine) |
| WO2006099468A2 (en) * | 2005-03-14 | 2006-09-21 | Teva Pharmaceutical Industries Ltd. | Process for the purification of duloxetine hydrochloride |
| WO2006099433A1 (en) * | 2005-03-14 | 2006-09-21 | Teva Pharmaceutical Industries Ltd. | 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 |
| WO2007148102A2 (en) * | 2006-06-23 | 2007-12-27 | Arrow International Limited | Crystalline duloxetine hydrochloride |
| WO2007148096A1 (en) * | 2006-06-23 | 2007-12-27 | Arrow International Limited | Crystalline duloxetine hydrochloride |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120047262A (ko) | 2012-05-11 |
| ZA201201570B (en) | 2013-08-28 |
| BR112012004862A2 (pt) | 2015-09-08 |
| EA201290127A1 (ru) | 2013-02-28 |
| EP2473497A1 (en) | 2012-07-11 |
| JP2013503823A (ja) | 2013-02-04 |
| MX2012002621A (es) | 2012-07-03 |
| IL218329A0 (en) | 2012-04-30 |
| CN102482254A (zh) | 2012-05-30 |
| CZ2009584A3 (cs) | 2011-03-09 |
| WO2011026449A1 (en) | 2011-03-10 |
| CZ304602B6 (cs) | 2014-07-30 |
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