HRP20200883T1 - Postupak za pripremanje (2z,5z)-5-(3-kloro-4-((r)-2,3-dihidroksipropoksi)benziliden)-2-(propilimino)-3-(o-tolil)tiazolidin-4-ona i međuproizvodi koji se koriste u navedenom postupku - Google Patents
Postupak za pripremanje (2z,5z)-5-(3-kloro-4-((r)-2,3-dihidroksipropoksi)benziliden)-2-(propilimino)-3-(o-tolil)tiazolidin-4-ona i međuproizvodi koji se koriste u navedenom postupku Download PDFInfo
- Publication number
- HRP20200883T1 HRP20200883T1 HRP20200883TT HRP20200883T HRP20200883T1 HR P20200883 T1 HRP20200883 T1 HR P20200883T1 HR P20200883T T HRP20200883T T HR P20200883TT HR P20200883 T HRP20200883 T HR P20200883T HR P20200883 T1 HRP20200883 T1 HR P20200883T1
- Authority
- HR
- Croatia
- Prior art keywords
- chloro
- dihydroxypropoxy
- tolyl
- propylimino
- thiazolidin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 10
- LPAUOXUZGSBGDU-ULCCENQXSA-N (5z)-5-[[3-chloro-4-[(2r)-2,3-dihydroxypropoxy]phenyl]methylidene]-3-(2-methylphenyl)-2-propylimino-1,3-thiazolidin-4-one Chemical compound O=C1N(C=2C(=CC=CC=2)C)C(=NCCC)S\C1=C/C1=CC=C(OC[C@H](O)CO)C(Cl)=C1 LPAUOXUZGSBGDU-ULCCENQXSA-N 0.000 title claims 6
- LGBCRCZEDRZSDA-MRVPVSSYSA-N 3-chloro-4-[(2r)-2,3-dihydroxypropoxy]benzaldehyde Chemical compound OC[C@@H](O)COC1=CC=C(C=O)C=C1Cl LGBCRCZEDRZSDA-MRVPVSSYSA-N 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- OYBHACSOBWDLDC-YPKPFQOOSA-N CCC\N=C1/SCC(=O)N1C1=CC=CC=C1C Chemical compound CCC\N=C1/SCC(=O)N1C1=CC=CC=C1C OYBHACSOBWDLDC-YPKPFQOOSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000002425 crystallisation Methods 0.000 claims 3
- 230000008025 crystallization Effects 0.000 claims 3
- SSZWWUDQMAHNAQ-VKHMYHEASA-N (R)-3-chloro-1,2-propanediol Chemical compound OC[C@@H](O)CCl SSZWWUDQMAHNAQ-VKHMYHEASA-N 0.000 claims 2
- VGSOCYWCRMXQAB-UHFFFAOYSA-N 3-chloro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1Cl VGSOCYWCRMXQAB-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 238000010586 diagram Methods 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- JYKYYPPZLPVIBY-UHFFFAOYSA-N 1-isothiocyanato-2-methylbenzene Chemical compound CC1=CC=CC=C1N=C=S JYKYYPPZLPVIBY-UHFFFAOYSA-N 0.000 claims 1
- PXZPXFHUJCLESQ-UHFFFAOYSA-N 2-(2-methylphenyl)-1,3-thiazolidin-4-one Chemical compound CC1=CC=CC=C1C1SCC(=O)N1 PXZPXFHUJCLESQ-UHFFFAOYSA-N 0.000 claims 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/77—Preparation of chelates of aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Claims (11)
1. Postupak za pripremanje (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehida (1):
[image]
koji postupak uključuje reakciju 3-kloro-4-hidroksibenzaldehida s (R)-3-kloro-1,2-propandiolom i izoliranje dobivenog (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehida putem kristalizacije, pri čemu se reakcija 3-kloro-4-hidroksibenzaldehida s (R)-3-kloro-1,2-propandiolom provodi u prisutnosti baznog kalijevog terc-butoksida i otapala n-propanola, na temperaturi višoj od 50 °C, i pri čemu se dobiveni (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehid kristalizira u vodi sa su-otapalom n-propanolom.
2. Postupak prema patentnom zahtjevu 1, naznačen time što nadalje sadrži reakciju dobivenog (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehida (1) s 2-[(Z)-propilimino]-3-o-tolil-tiazolidin-4-onom da se dobije (2Z,5Z)-5-(3-kloro-4-((R)-2,3-dihidroksipropoksi)benziliden)-2-(propilimino)-3-(o-tolil)tiazolidin-4-on (2):
[image]
3. Postupak prema patentnom zahtjevu 2, naznačen time što se 2-[(Z)-propilimino]-3-o-tolil-tiazolidin-4-on priprema reakcijom o-tolil-izo-tiocijanata s n-propilaminom zatim reakcijom s bromo-acetil bromidom i bazom piridinom, pri čemu ne dolazi do izolacije i/ili pročišćavanja međuproizvoda i pri čemu dobiveni 2-[(Z)-propilimino]-3-o-tolil-tiazolidin-4-on nije izdvojen i/ili pročišćen prije reakcije s (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehidom (1).
4. Postupak prema patentnom zahtjevu 3, naznačen time što (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehid (1) reagira s 2-[(Z)-propilimino]-3-o-tolil-tiazolidin-4-onom u prisutnosti otapala etanola i baze natrijevog acetata, na temperaturi višoj od 50 °C.
5. Postupak prema bilo kojem od patentnih zahtjeva 2 do 4, naznačen time što je (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehid (1) izdvojen pomoću jedne kristalizacije prije reakcije s 2-[(Z)-propilimino]-3-o-tolil-tiazolidin-4-onom.
6. Postupak prema bilo kojem od patentnih zahtjeva 2 do 5, naznačen time što je u prvom koraku izoliranja dobiveni spoj (2) izdvojen pomoću kristalizacije.
7. Postupak prema patentnom zahtjevu 6, naznačen time što se dobiveni kristalni spoj (2) dodatno pročišćava s jednim ili više koraka rekristalizacije.
8. Spoj (R)-3-kloro-4-(2,3-dihidroksipropoksi)-benzaldehid u kristalnom obliku.
9. Kristalni oblik prema patentnom zahtjevu 8, naznačen time što ima vrhove u dijagramu rendgenske difrakcije praha pod sljedećim kutovima refrakcije 2θ: 7.3°, 9.7°, 12.7°, 13.3°, 19.6°, 22.1°, 27.9°, i 28.5°, pri čemu se dijagram difrakcije rendgenskih zraka dobiva primjenom Cu Kα1 zračenja (λ = 1.5406 Å) i uklanjanjem komponente Kα2 i pri čemu je točnost vrijednosti 2θ u rasponu od +/- 0.1-0.2°.
10. Kristalni oblik prema patentnom zahtjevu 8 ili 9, naznačen time što ima talište od 94 ± 5 °C kako je određeno s diferencijalnom pretražnom kalorimetrijom.
11. Uporaba kristalnog oblika prema bilo kojem od zahtjeva 8 do 10, naznačena time što je za dobivanje (2Z,5Z)-5-(3-kloro-4-((R)-2,3-dihidroksipropoksi)benziliden)-2-(propilimino)-3-(o-tolil)tiazolidin-4-ona.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12180920 | 2012-08-17 | ||
| PCT/IB2013/056662 WO2014027330A1 (en) | 2012-08-17 | 2013-08-15 | Process for the preparation of|(2z,5z)-5-(3-chloro-4-((r)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-|(o-tolyl)thiazolidin-4-one and intermediate used in said process |
| EP13779378.2A EP2885266B1 (en) | 2012-08-17 | 2013-08-15 | Process for the preparation of (2z,5z)-5-(3-chloro-4-((r)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-(o-tolyl)thiazolidin-4-one and intermediate used in said process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20200883T1 true HRP20200883T1 (hr) | 2020-09-04 |
Family
ID=46940231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20200883TT HRP20200883T1 (hr) | 2012-08-17 | 2020-06-02 | Postupak za pripremanje (2z,5z)-5-(3-kloro-4-((r)-2,3-dihidroksipropoksi)benziliden)-2-(propilimino)-3-(o-tolil)tiazolidin-4-ona i međuproizvodi koji se koriste u navedenom postupku |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US9340518B2 (hr) |
| EP (1) | EP2885266B1 (hr) |
| JP (2) | JP6322630B2 (hr) |
| KR (1) | KR101731739B1 (hr) |
| CN (1) | CN104540800B (hr) |
| CA (1) | CA2895172C (hr) |
| CY (1) | CY1123300T1 (hr) |
| DK (1) | DK2885266T3 (hr) |
| ES (1) | ES2795105T3 (hr) |
| HR (1) | HRP20200883T1 (hr) |
| HU (1) | HUE050733T2 (hr) |
| IL (1) | IL237198A (hr) |
| LT (1) | LT2885266T (hr) |
| MX (1) | MX350891B (hr) |
| PL (1) | PL2885266T3 (hr) |
| PT (1) | PT2885266T (hr) |
| RS (1) | RS60408B1 (hr) |
| SI (1) | SI2885266T1 (hr) |
| TW (1) | TWI606036B (hr) |
| WO (1) | WO2014027330A1 (hr) |
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| ES2617628T5 (es) | 2008-03-17 | 2020-06-01 | Actelion Pharmaceuticals Ltd | Régimen de dosificación para un agonista selectivo del receptor de S1P1 |
| JP6322630B2 (ja) * | 2012-08-17 | 2018-05-09 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | （２Ｚ，５Ｚ）−５−（３−クロロ−４−（（Ｒ）−２，３−ジヒドロキシプロポキシ）ベンジリデン）−２−（プロピルイミノ）−３−（ｏ−トリル）チアゾリジン−４−オンの製造方法及び前記方法において使用される中間体 |
| MA41139A (fr) | 2014-12-11 | 2017-10-17 | Actelion Pharmaceuticals Ltd | Combinaison pharmaceutique comportant un agoniste sélectif du récepteur sip1 |
| MY188764A (en) | 2014-12-11 | 2021-12-30 | Actelion Pharmaceuticals Ltd | Dosing regimen for a selective s1p1 receptor agonist |
| CA3009713A1 (en) * | 2015-12-25 | 2017-06-29 | Crystal Pharmatech Co., Ltd. | Crystalline forms of ponesimod and preparation method thereof |
| JOP20190207A1 (ar) | 2017-03-14 | 2019-09-10 | Actelion Pharmaceuticals Ltd | تركيبة صيدلانية تشتمل على بونيسيمود |
| US11220488B2 (en) | 2017-09-19 | 2022-01-11 | Teva Pharmaceuticals International Gmbh | Crystalline polymorph of Ponesimod |
| US11186556B1 (en) | 2018-10-16 | 2021-11-30 | Celgene Corporation | Salts of a thiazolidinone compound, solid forms, compositions and methods of use thereof |
| US11014940B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Thiazolidinone and oxazolidinone compounds and formulations |
| US11013723B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Solid forms of a thiazolidinone compound, compositions and methods of use thereof |
| US11014897B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Solid forms comprising a thiazolidinone compound, compositions and methods of use thereof |
| KR102365655B1 (ko) | 2018-11-29 | 2022-02-22 | 원광대학교 산학협력단 | 콩 발효 추출물을 유효성분으로 포함하는 피부 주름 예방 또는 개선용 조성물 |
| AU2020372647A1 (en) | 2019-10-31 | 2022-06-16 | Idorsia Pharmaceuticals Ltd | Combination of a CXCR7 antagonist with an S1P1 receptor modulator |
| WO2023022896A1 (en) | 2021-08-17 | 2023-02-23 | Teva Czech Industries S.R.O | Polymorphs of ponesimod |
| EP4212156A1 (en) | 2022-01-13 | 2023-07-19 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a s1p receptor modulator |
| WO2023152691A1 (en) * | 2022-02-10 | 2023-08-17 | Metrochem Api Pvt Ltd | Process for the preparation of ponesimod and its intermediates thereof |
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| TWI404706B (zh) | 2006-01-11 | 2013-08-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| ATE447568T1 (de) | 2006-01-24 | 2009-11-15 | Actelion Pharmaceuticals Ltd | Neue pyrinderivate |
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| SI2195311T1 (sl) | 2007-08-17 | 2011-07-29 | Actelion Pharmaceuticals Ltd | Derivati piridina kot modulatorji receptorja s1p1/edg1 |
| ES2617628T5 (es) | 2008-03-17 | 2020-06-01 | Actelion Pharmaceuticals Ltd | Régimen de dosificación para un agonista selectivo del receptor de S1P1 |
| GB0819182D0 (en) | 2008-10-20 | 2008-11-26 | Actelion Pharmaceuticals Ltd | Crystalline forms |
| US20100160369A1 (en) | 2008-12-04 | 2010-06-24 | Exelixis, Inc. | S1P1 Agonists and Methods of Making And Using |
| LT3409274T (lt) | 2008-12-22 | 2020-02-10 | Novartis Ag | Dozavimo schema s1p receptoriaus agonistui |
| AR074825A1 (es) | 2008-12-22 | 2011-02-16 | Novartis Ag | Regimen de dosificacion de un agonista de los receptores de s1p, metodo de tratamiento y kit |
| JP6322630B2 (ja) * | 2012-08-17 | 2018-05-09 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | （２Ｚ，５Ｚ）−５−（３−クロロ−４−（（Ｒ）−２，３−ジヒドロキシプロポキシ）ベンジリデン）−２−（プロピルイミノ）−３−（ｏ−トリル）チアゾリジン−４−オンの製造方法及び前記方法において使用される中間体 |
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- 2013-08-15 JP JP2015527061A patent/JP6322630B2/ja active Active
- 2013-08-15 PT PT137793782T patent/PT2885266T/pt unknown
- 2013-08-15 HU HUE13779378A patent/HUE050733T2/hu unknown
- 2013-08-15 MX MX2015002127A patent/MX350891B/es active IP Right Grant
- 2013-08-15 DK DK13779378.2T patent/DK2885266T3/da active
- 2013-08-15 EP EP13779378.2A patent/EP2885266B1/en active Active
- 2013-08-15 PL PL13779378T patent/PL2885266T3/pl unknown
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- 2013-08-15 WO PCT/IB2013/056662 patent/WO2014027330A1/en active Application Filing
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- 2013-08-15 KR KR1020157006474A patent/KR101731739B1/ko active IP Right Grant
- 2013-08-15 US US14/422,167 patent/US9340518B2/en active Active
- 2013-08-15 CN CN201380042658.2A patent/CN104540800B/zh active Active
- 2013-08-15 CA CA2895172A patent/CA2895172C/en active Active
- 2013-08-15 SI SI201331742T patent/SI2885266T1/sl unknown
- 2013-08-15 LT LTEP13779378.2T patent/LT2885266T/lt unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| PT2885266T (pt) | 2020-05-29 |
| MX2015002127A (es) | 2015-05-11 |
| IL237198A0 (en) | 2015-04-30 |
| CA2895172A1 (en) | 2014-02-20 |
| ES2795105T3 (es) | 2020-11-20 |
| TWI606036B (zh) | 2017-11-21 |
| MX350891B (es) | 2017-09-22 |
| TW201408634A (zh) | 2014-03-01 |
| JP2015530373A (ja) | 2015-10-15 |
| CA2895172C (en) | 2020-08-18 |
| LT2885266T (lt) | 2020-07-10 |
| RS60408B1 (sr) | 2020-07-31 |
| WO2014027330A1 (en) | 2014-02-20 |
| JP6424250B2 (ja) | 2018-11-14 |
| JP2017160223A (ja) | 2017-09-14 |
| JP6322630B2 (ja) | 2018-05-09 |
| KR20150042277A (ko) | 2015-04-20 |
| CY1123300T1 (el) | 2021-12-31 |
| US9340518B2 (en) | 2016-05-17 |
| PL2885266T3 (pl) | 2020-11-16 |
| EP2885266B1 (en) | 2020-03-18 |
| CN104540800A (zh) | 2015-04-22 |
| EP2885266A1 (en) | 2015-06-24 |
| SI2885266T1 (sl) | 2020-10-30 |
| HUE050733T2 (hu) | 2021-01-28 |
| US20150203459A1 (en) | 2015-07-23 |
| KR101731739B1 (ko) | 2017-05-11 |
| DK2885266T3 (da) | 2020-06-08 |
| IL237198A (en) | 2017-12-31 |
| CN104540800B (zh) | 2017-05-10 |
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