HRP20230081T1 - Kristalni monohidratni kompleks od 1-cijano-2-(4-ciklopropil-benzil)-4-(beta-d-glukopiranoz-1-il)-benzena i l- prolina u kristalnoj vodi (1:1:1), postupci za njegovu pripravu i njegova uporaba kao sglt inhibitora - Google Patents
Kristalni monohidratni kompleks od 1-cijano-2-(4-ciklopropil-benzil)-4-(beta-d-glukopiranoz-1-il)-benzena i l- prolina u kristalnoj vodi (1:1:1), postupci za njegovu pripravu i njegova uporaba kao sglt inhibitora Download PDFInfo
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- HRP20230081T1 HRP20230081T1 HRP20230081TT HRP20230081T HRP20230081T1 HR P20230081 T1 HRP20230081 T1 HR P20230081T1 HR P20230081T T HRP20230081T T HR P20230081TT HR P20230081 T HRP20230081 T HR P20230081T HR P20230081 T1 HRP20230081 T1 HR P20230081T1
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- diffraction pattern
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- ray powder
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- PESZPPAQWQMZAM-XNBWIAOKSA-N 2-[(4-cyclopropylphenyl)methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(C#N)C(CC=2C=CC(=CC=2)C2CC2)=C1 PESZPPAQWQMZAM-XNBWIAOKSA-N 0.000 title claims 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 title claims 4
- 239000013078 crystal Substances 0.000 title claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims 2
- 150000004682 monohydrates Chemical class 0.000 title 1
- 229940121377 sodium-glucose co-transporter inhibitor Drugs 0.000 title 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 9
- 230000005855 radiation Effects 0.000 claims 6
- 102000034534 Cotransporters Human genes 0.000 claims 2
- 108020003264 Cotransporters Proteins 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229930182821 L-proline Natural products 0.000 claims 1
- 108091006269 SLC5A2 Proteins 0.000 claims 1
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 1
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 1
- 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 229960002429 proline Drugs 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Claims (11)
1. Kristalni kompleks između 1-cijano-2-(4-ciklopropil-benzil)-4-(ß-D-glukopiranoz-1-il)-benzena i jedne ili više prirodnih aminokiselina, naznačen time, da prirodna aminokiselina je L-prolin, i time, da kristalni kompleks je kompleks (1:1) između 1-cijano-2-(4-ciklopropil-benzil)-4-(ß-D-glukopiranoz-1-il)-benzena i L-prolina, i time, da kristalni kompleks je kristalni hidrat, i time, da molarni omjer kristalnog kompleksa od 1-cijano-2-(4-ciklopropil-benzil)-4-(ß-D-glukopiranoz-1-il)-benzena i L-prolina prema kristalnoj vodi iznosi 1:1.
2. Kristalni kompleks prema patentnom zahtjevu 1, naznačen time, da posjeduje uzorak rendgenske difrakcije na prahu koji ima maksimume na 20,28, 21,14 i 21,64 stupnja 2Θ (±0,1 stupanj 2Θ), pri čemu se navedeni uzorak rendgenske difrakcije na prahu izrađuje uporabom CuKα1 radijacije.
3. Kristalni kompleks prema patentnom zahtjevu 1 ili 2, naznačen time, da uzorak rendgenske difrakcije na prahu nadalje ima maksimume na 4,99 i 23,23 stupnja 2Θ (±0,1 stupanj 2Θ), pri čemu se navedeni uzorak rendgenske difrakcije na prahu izrađuje uporabom CuKα1 radijacije.
4. Kristalni kompleks prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da uzorak rendgenske difrakcije na prahu nadalje ima maksimume na 17,61, 17,77 i 27,66 stupnjeva 2Θ (±0,1 stupanj 2Θ), pri čemu se navedeni uzorak rendgenske difrakcije na prahu izrađuje uporabom CuKα1 radijacije.
5. Kristalni kompleks prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da uzorak rendgenske difrakcije na prahu ima maksimume na 4,99, 15,12, 17,61, 17,77, 18,17, 20,28, 21,14, 21,64, 23,23 i 27,66 stupnjeva 2Θ (±0,1 stupanj 2Θ), pri čemu se navedeni uzorak rendgenske difrakcije na prahu izrađuje uporabom CuKα1 radijacije.
6. Kristalni kompleks prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da njegov uzorak rendgenske difrakcije na prahu, koji se izrađuje uporabom CuKα1 radijacije, ima maksimume na stupnjevima 2Θ (±0,1 stupanj 2Θ) kako slijedi:
[image]
7. Kristalni kompleks prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time, da njegov uzorak rendgenske difrakcije na prahu, koji se izrađuje uporabom CuKα1 radijacije, ima maksimume na stupnjevima 2Θ (±0,1 stupanj 2Θ) kako je prikazano na Slici 1.
8. Farmaceutski pripravak, naznačen time, da sadrži jedan ili više kristalnih kompleksa u skladu s jednim ili više od patentnih zahtjeva 1 do 7.
9. Kristalni kompleks prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da se upotrebljava kao lijek.
10. Kristalni kompleks prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da je za uporabu u liječenju ili prevenciji bolesti ili stanja na koja se može utjecati putem inhibicije o natriju ovisnog SGLT kotransportera glukoze.
11. Kristalni kompleks prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da je za uporabu u liječenju ili prevenciji bolesti ili stanja na koja se može utjecati putem inhibicije o natriju ovisnog SGLT2 kotransportera glukoze.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12177944 | 2012-07-26 | ||
| EP18155079.9A EP3351539B1 (en) | 2012-07-26 | 2013-07-25 | Crystalline monohydrate complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(beta-d-glucopyranos-1-yl)-benzene and l-proline in crystal water (1:1:1), methods for its preparation and its use as an sglt inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20230081T1 true HRP20230081T1 (hr) | 2023-03-17 |
Family
ID=48874313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20230081TT HRP20230081T1 (hr) | 2012-07-26 | 2013-07-25 | Kristalni monohidratni kompleks od 1-cijano-2-(4-ciklopropil-benzil)-4-(beta-d-glukopiranoz-1-il)-benzena i l- prolina u kristalnoj vodi (1:1:1), postupci za njegovu pripravu i njegova uporaba kao sglt inhibitora |
| HRP20181972TT HRP20181972T1 (hr) | 2012-07-26 | 2018-11-23 | KRISTALNI KOMPLEKS IZ 1-CIJANO-2-(4-CIKLOPROPIL-BENZIL)-4-(ß-D-GLUKOPIRANOZ-1-IL)-BENZENA, POSTUPCI ZA NJEGOVU PROIZVODNJU I NJEGOVA UPORABA ZA PRIPRAVLJANJE LIJEKOVA |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20181972TT HRP20181972T1 (hr) | 2012-07-26 | 2018-11-23 | KRISTALNI KOMPLEKS IZ 1-CIJANO-2-(4-CIKLOPROPIL-BENZIL)-4-(ß-D-GLUKOPIRANOZ-1-IL)-BENZENA, POSTUPCI ZA NJEGOVU PROIZVODNJU I NJEGOVA UPORABA ZA PRIPRAVLJANJE LIJEKOVA |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9145434B2 (hr) |
| EP (3) | EP3351539B1 (hr) |
| JP (2) | JP6538556B2 (hr) |
| CN (2) | CN108774200A (hr) |
| AR (1) | AR091908A1 (hr) |
| AU (1) | AU2013294947B2 (hr) |
| BR (1) | BR112015001327B1 (hr) |
| CA (1) | CA2878698C (hr) |
| DK (2) | DK2877460T3 (hr) |
| EA (2) | EA201600506A1 (hr) |
| ES (2) | ES2694675T3 (hr) |
| FI (1) | FI3351539T3 (hr) |
| HR (2) | HRP20230081T1 (hr) |
| HU (1) | HUE061450T2 (hr) |
| LT (1) | LT3351539T (hr) |
| MX (1) | MX357906B (hr) |
| PL (2) | PL3351539T3 (hr) |
| PT (2) | PT3351539T (hr) |
| RS (1) | RS63881B1 (hr) |
| SG (1) | SG11201500574QA (hr) |
| SI (2) | SI3351539T1 (hr) |
| TW (1) | TW201418275A (hr) |
| WO (1) | WO2014016381A1 (hr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9145434B2 (en) | 2012-07-26 | 2015-09-29 | Boehringer Ingelheim International Gmbh | Crystalline complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(ss-d-glucopyranos-1-yl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| EP4245765A3 (en) | 2013-04-04 | 2024-03-20 | Boehringer Ingelheim Vetmedica GmbH | Treatment of metabolic disorders in equine animals |
| DK3082829T3 (da) * | 2013-12-17 | 2021-05-03 | Boehringer Ingelheim Vetmedica Gmbh | Sglt2-inhibitorer til behandlingen af metaboliske lidelser i kattedyr |
| LT3485890T (lt) | 2014-01-23 | 2023-07-25 | Boehringer Ingelheim Vetmedica Gmbh | Sglt2 inhibitoriai, skirti šuninių gyvūnų medžiagų apykaitos sutrikimų gydymui |
| MX2016012705A (es) | 2014-04-01 | 2016-12-16 | Boehringer Ingelheim Vetmedica Gmbh | Tratamiento de trastornos metabolicos en animales equinos. |
| CN103965020B (zh) * | 2014-05-06 | 2015-09-09 | 启东东岳药业有限公司 | 制备5-碘-2-溴苄醇的方法 |
| EP3197429B1 (en) * | 2014-09-25 | 2024-05-22 | Boehringer Ingelheim Vetmedica GmbH | Combination treatment of sglt2 inhibitors and dopamine agonists for preventing metabolic disorders in equine animals |
| PT3202772T (pt) * | 2014-09-30 | 2020-11-20 | Jiangsu Hengrui Medicine Co | Cristal de um complexo de l-prolina/inibidor do cotransportador de sódio-glicose 2 |
| CZ2015110A3 (cs) * | 2015-02-18 | 2016-08-31 | Zentiva, K.S. | Pevné formy empagliflozinu |
| AU2016310535B2 (en) | 2015-08-27 | 2021-08-19 | Boehringer Ingelheim Vetmedica Gmbh | Liquid pharmaceutical compositions comprising SGLT-2 inhibitors |
| WO2017203457A1 (en) * | 2016-05-26 | 2017-11-30 | Dr. Reddy's Laboratories Limited | Solid state forms of empagliflozin |
| EP3466940B1 (en) * | 2016-05-28 | 2021-11-17 | Ji Lin Hui Sheng Bio-Pharmaceutical Co., Ltd. | Crystal form of sodium-glucose cotransporter 2 inhibitor |
| CA3085671A1 (en) | 2017-12-19 | 2019-06-27 | Boehringer Ingelheim Vetmedica Gmbh | Synthesis of the 1:1:1 co-crystal of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(beta-d-glucopyranos-1 -yl)-benzene, l-proline and water |
| MX2022006490A (es) | 2019-11-28 | 2022-07-04 | Boehringer Ingelheim Vetmedica Gmbh | Uso de inhibidores de sglt-2 en el secado de mamiferos no humanos. |
| EP4106744A1 (en) | 2020-02-17 | 2022-12-28 | Boehringer Ingelheim Vetmedica GmbH | Use of sglt-2 inhibitors for the prevention and/or treatment of cardiac diseases in felines |
| CA3224673A1 (en) | 2021-07-28 | 2023-02-02 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of renal diseases in non-human mammals |
| CN117715640A (zh) | 2021-07-28 | 2024-03-15 | 勃林格殷格翰动物保健有限公司 | Sglt-2抑制剂用于在不包括猫科动物的非人哺乳动物，特别是犬科动物中预防和/或治疗心脏疾病的用途 |
| WO2023006745A1 (en) | 2021-07-28 | 2023-02-02 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of hypertension in non-human mammals |
| WO2023227492A1 (en) | 2022-05-25 | 2023-11-30 | Boehringer Ingelheim Vetmedica Gmbh | Aqueous pharmaceutical compositions comprising sglt-2 inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6774112B2 (en) * | 2001-04-11 | 2004-08-10 | Bristol-Myers Squibb Company | Amino acid complexes of C-aryl glucosides for treatment of diabetes and method |
| US7927613B2 (en) * | 2002-02-15 | 2011-04-19 | University Of South Florida | Pharmaceutical co-crystal compositions |
| CN101260130A (zh) * | 2003-01-03 | 2008-09-10 | 布里斯托尔-迈尔斯斯奎布公司 | 制备c-芳基葡糖苷sglt2抑制剂的方法 |
| EP2360165A3 (de) * | 2004-03-16 | 2012-01-04 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituierte Benzol-Derivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| BRPI0615882A2 (pt) * | 2005-09-08 | 2011-05-31 | Boehringer Ingelheim Int | formas cristalinas de 1-cloro-4-(beta-d-glicopiranos-1-il)-2-(4-etinil-benzil)- benzeno, métodos para sua preparação e o uso para preparar medicamentos do mesmo |
| KR20080102395A (ko) * | 2006-02-15 | 2008-11-25 | 베링거 인겔하임 인터내셔날 게엠베하 | 글루코피라노실-치환된 벤조니트릴 유도체, 당해 화합물을 함유하는 약제학적 조성물, 이들의 용도 및 이들의 제조방법 |
| TWI370818B (en) * | 2006-04-05 | 2012-08-21 | Astellas Pharma Inc | Cocrystal of c-glycoside derivative and l-proline |
| PE20080697A1 (es) * | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| US7919598B2 (en) | 2006-06-28 | 2011-04-05 | Bristol-Myers Squibb Company | Crystal structures of SGLT2 inhibitors and processes for preparing same |
| TW200817424A (en) | 2006-08-04 | 2008-04-16 | Daiichi Sankyo Co Ltd | Benzylphenyl glucopyranoside derivatives |
| AR065809A1 (es) | 2007-03-22 | 2009-07-01 | Bristol Myers Squibb Co | Formulaciones farmaceuticas que contienen un inhibidor sglt2 |
| JP2010528023A (ja) * | 2007-05-18 | 2010-08-19 | ブリストル−マイヤーズ スクイブ カンパニー | Ｓｇｌｔ２阻害剤の結晶構造およびその製造方法 |
| CN103319445B (zh) * | 2007-12-27 | 2016-01-20 | 阿斯利康公司 | Sglt2抑制剂的晶体结构及其制备方法 |
| TWI441831B (zh) * | 2008-08-22 | 2014-06-21 | Theracos Inc | 製備ｓｇｌｔ２抑制劑之方法 |
| AU2009286380B2 (en) | 2008-08-28 | 2011-09-15 | Pfizer Inc. | Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives |
| WO2010048358A2 (en) | 2008-10-22 | 2010-04-29 | Auspex Pharmaceutical, Inc. | Ethoxyphenylmethyl inhibitors of sglt2 |
| WO2011153712A1 (en) * | 2010-06-12 | 2011-12-15 | Theracos, Inc. | Crystalline form of benzylbenzene sglt2 inhibitor |
| US9145434B2 (en) | 2012-07-26 | 2015-09-29 | Boehringer Ingelheim International Gmbh | Crystalline complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(ss-d-glucopyranos-1-yl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| EP4245765A3 (en) | 2013-04-04 | 2024-03-20 | Boehringer Ingelheim Vetmedica GmbH | Treatment of metabolic disorders in equine animals |
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2013
- 2013-07-23 US US13/948,751 patent/US9145434B2/en active Active
- 2013-07-25 ES ES13740309.3T patent/ES2694675T3/es active Active
- 2013-07-25 PL PL18155079.9T patent/PL3351539T3/pl unknown
- 2013-07-25 TW TW102126724A patent/TW201418275A/zh unknown
- 2013-07-25 EA EA201600506A patent/EA201600506A1/ru unknown
- 2013-07-25 PT PT181550799T patent/PT3351539T/pt unknown
- 2013-07-25 EP EP18155079.9A patent/EP3351539B1/en active Active
- 2013-07-25 WO PCT/EP2013/065736 patent/WO2014016381A1/en active Application Filing
- 2013-07-25 CN CN201810468431.9A patent/CN108774200A/zh active Pending
- 2013-07-25 RS RS20230025A patent/RS63881B1/sr unknown
- 2013-07-25 JP JP2015523552A patent/JP6538556B2/ja active Active
- 2013-07-25 LT LTEP18155079.9T patent/LT3351539T/lt unknown
- 2013-07-25 SG SG11201500574QA patent/SG11201500574QA/en unknown
- 2013-07-25 AU AU2013294947A patent/AU2013294947B2/en active Active
- 2013-07-25 ES ES18155079T patent/ES2937665T3/es active Active
- 2013-07-25 PL PL13740309T patent/PL2877460T3/pl unknown
- 2013-07-25 DK DK13740309.3T patent/DK2877460T3/en active
- 2013-07-25 EP EP22202153.7A patent/EP4166548A1/en active Pending
- 2013-07-25 AR ARP130102660A patent/AR091908A1/es unknown
- 2013-07-25 SI SI201332031T patent/SI3351539T1/sl unknown
- 2013-07-25 CA CA2878698A patent/CA2878698C/en active Active
- 2013-07-25 EA EA201500038A patent/EA025438B1/ru not_active IP Right Cessation
- 2013-07-25 PT PT13740309T patent/PT2877460T/pt unknown
- 2013-07-25 EP EP13740309.3A patent/EP2877460B1/en active Active
- 2013-07-25 BR BR112015001327-9A patent/BR112015001327B1/pt active IP Right Grant
- 2013-07-25 SI SI201331237T patent/SI2877460T1/sl unknown
- 2013-07-25 HU HUE18155079A patent/HUE061450T2/hu unknown
- 2013-07-25 MX MX2015000962A patent/MX357906B/es active IP Right Grant
- 2013-07-25 CN CN201380037186.1A patent/CN104470908A/zh active Pending
- 2013-07-25 DK DK18155079.9T patent/DK3351539T3/da active
- 2013-07-25 HR HRP20230081TT patent/HRP20230081T1/hr unknown
-
2018
- 2018-05-08 JP JP2018089968A patent/JP2018135384A/ja active Pending
- 2018-11-23 HR HRP20181972TT patent/HRP20181972T1/hr unknown
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2022
- 2022-07-25 FI FIEP18155079.9T patent/FI3351539T3/fi active
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