ES2600827B9 - Formas cristalinas de bilastina y procedimientos para su preparación - Google Patents
Formas cristalinas de bilastina y procedimientos para su preparación Download PDFInfo
- Publication number
- ES2600827B9 ES2600827B9 ES201690068A ES201690068A ES2600827B9 ES 2600827 B9 ES2600827 B9 ES 2600827B9 ES 201690068 A ES201690068 A ES 201690068A ES 201690068 A ES201690068 A ES 201690068A ES 2600827 B9 ES2600827 B9 ES 2600827B9
- Authority
- ES
- Spain
- Prior art keywords
- bilastine
- crystalline form
- eta
- temperature
- alpha
- 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
- ACCMWZWAEFYUGZ-UHFFFAOYSA-N bilastine Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1C(CC1)CCN1CCC1=CC=C(C(C)(C)C(O)=O)C=C1 ACCMWZWAEFYUGZ-UHFFFAOYSA-N 0.000 title claims abstract description 261
- 229960004314 bilastine Drugs 0.000 title claims abstract description 244
- 238000000034 method Methods 0.000 title claims abstract description 95
- 238000002360 preparation method Methods 0.000 title claims abstract description 37
- 230000008569 process Effects 0.000 claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 208000037273 Pathologic Processes Diseases 0.000 claims abstract description 7
- 229960001340 histamine Drugs 0.000 claims abstract description 7
- 230000001404 mediated effect Effects 0.000 claims abstract description 7
- 230000009054 pathological process Effects 0.000 claims abstract description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 66
- 238000002411 thermogravimetry Methods 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 36
- 230000009466 transformation Effects 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 239000000725 suspension Substances 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- 230000005855 radiation Effects 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000004580 weight loss Effects 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000002636 symptomatic treatment Methods 0.000 claims description 4
- 208000024780 Urticaria Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000001932 seasonal effect Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 7
- 239000003929 acidic solution Substances 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 238000010586 diagram Methods 0.000 description 46
- 239000007787 solid Substances 0.000 description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 238000002441 X-ray diffraction Methods 0.000 description 24
- 238000000113 differential scanning calorimetry Methods 0.000 description 20
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 12
- 238000000634 powder X-ray diffraction Methods 0.000 description 12
- 239000000843 powder Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000010979 pH adjustment Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000007907 direct compression Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 1
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100518501 Mus musculus Spp1 gene Proteins 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 108700041286 delta Proteins 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000004686 pentahydrates Chemical class 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000000547 structure data Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201531103 | 2015-07-24 | ||
| ESP201531103 | 2015-07-24 | ||
| PCT/ES2016/070560 WO2017017301A1 (es) | 2015-07-24 | 2016-07-22 | Formas cristalinas de bilastina y procedimientos para su preparación |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| ES2600827A1 ES2600827A1 (es) | 2017-02-10 |
| ES2600827A8 ES2600827A8 (es) | 2017-06-15 |
| ES2600827B1 ES2600827B1 (es) | 2017-11-24 |
| ES2600827B9 true ES2600827B9 (es) | 2018-03-28 |
Family
ID=57884122
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES201690068A Expired - Fee Related ES2600827B9 (es) | 2015-07-24 | 2016-07-22 | Formas cristalinas de bilastina y procedimientos para su preparación |
| ES16829901T Active ES2874577T3 (es) | 2015-07-24 | 2016-07-22 | Formas cristalinas de bilastina y procedimientos para su preparación |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16829901T Active ES2874577T3 (es) | 2015-07-24 | 2016-07-22 | Formas cristalinas de bilastina y procedimientos para su preparación |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP3327012B1 (enExample) |
| JP (1) | JP7168447B2 (enExample) |
| KR (1) | KR102657147B1 (enExample) |
| CN (1) | CN107849007B (enExample) |
| CA (1) | CA2993134A1 (enExample) |
| CY (1) | CY1124505T1 (enExample) |
| ES (2) | ES2600827B9 (enExample) |
| LT (1) | LT3327012T (enExample) |
| MX (1) | MX382563B (enExample) |
| PL (1) | PL3327012T3 (enExample) |
| PT (1) | PT3327012T (enExample) |
| SI (1) | SI3327012T1 (enExample) |
| WO (1) | WO2017017301A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3452462A4 (en) * | 2016-05-05 | 2019-10-23 | MSN Laboratories Private Limited, R&D Center | Solid state forms of 2-[4-(2-{4-[1-(2-ethoxyethyl)-1h-benzimidazol-2-yl]-1-piperidinyl}ethyl)phenyl]-2-methylpropanoic acid and process for preparation thereof |
| EP3453384B1 (en) | 2017-09-07 | 2020-05-27 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Pharmaceutical tablet composition comprising bilastine |
| ES2835287T3 (es) | 2017-12-18 | 2021-06-22 | Tiefenbacher Alfred E Gmbh & Co Kg | Composición farmacéutica de comprimido que comprende la forma polimórfica 3 de bilastina y aluminometasilicato de magnesio |
| EP3641735B1 (en) | 2017-12-18 | 2021-02-24 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Pharmaceutical tablet composition comprising bilastine form 3 and a water-soluble filler |
| BR112021005403A2 (pt) * | 2018-09-25 | 2021-06-15 | Glenmark Life Sciences Limited | processos para a preparação de forma cristalina 2 de bilastina e para a preparação de solvato de p-xileno de bilastina, e, solvato de p-xileno de bilastina |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2124167B1 (es) * | 1996-06-04 | 1999-09-16 | Espanola Prod Quimicos | Nuevos derivados del bencimidazol con actividad antihistaminica. |
| BRPI0215703B8 (pt) * | 2002-04-19 | 2021-05-25 | Faes Farma Sa | polimorfo de ácido 4-[2-[1-(2-etoxietil)-1h-benzidimazol-2-il]-1-piperidinil]etil]-a, a-dimetil-benzenoacético, preparado farmacêutico, e seu uso do polimorfo 1 |
| CZ307500B6 (cs) * | 2012-08-15 | 2018-10-24 | Zentiva, K.S. | Způsob přípravy derivátu 2-methyl-2´-fenylpropionové kyseliny využívající nové intermediáty |
| CN103214454A (zh) * | 2013-03-30 | 2013-07-24 | 北京万全德众医药生物技术有限公司 | 一种比拉斯汀晶型及制备方法 |
| CN104447682A (zh) * | 2013-09-12 | 2015-03-25 | 天津市汉康医药生物技术有限公司 | 比拉斯汀化合物 |
| CN104447683A (zh) * | 2013-09-12 | 2015-03-25 | 天津市汉康医药生物技术有限公司 | 一种稳定的比拉斯汀化合物 |
| SK7066Y1 (sk) * | 2014-01-29 | 2015-03-03 | Zentiva Ks | Kryštalický dihydrát bilastínu |
| CN103788062A (zh) * | 2014-02-17 | 2014-05-14 | 北京博泽德润医药科技开发有限公司 | 一种比拉斯汀晶型及其制备方法 |
| CN104151290A (zh) * | 2014-06-30 | 2014-11-19 | 北京万全德众医药生物技术有限公司 | 一种制备比拉斯汀新晶型的方法 |
| CN104177331B (zh) * | 2014-09-10 | 2016-08-17 | 北京科莱博医药开发有限责任公司 | 比拉斯汀的制备方法 |
| CN104530002B (zh) * | 2015-01-29 | 2017-06-09 | 天津梅花生物医药科技有限公司 | 比拉斯汀化合物及其制备方法 |
-
2016
- 2016-07-22 EP EP16829901.4A patent/EP3327012B1/en active Active
- 2016-07-22 WO PCT/ES2016/070560 patent/WO2017017301A1/es not_active Ceased
- 2016-07-22 ES ES201690068A patent/ES2600827B9/es not_active Expired - Fee Related
- 2016-07-22 ES ES16829901T patent/ES2874577T3/es active Active
- 2016-07-22 KR KR1020187003411A patent/KR102657147B1/ko active Active
- 2016-07-22 JP JP2018522878A patent/JP7168447B2/ja active Active
- 2016-07-22 MX MX2018000883A patent/MX382563B/es unknown
- 2016-07-22 CN CN201680042950.8A patent/CN107849007B/zh active Active
- 2016-07-22 SI SI201631236T patent/SI3327012T1/sl unknown
- 2016-07-22 LT LTEP16829901.4T patent/LT3327012T/lt unknown
- 2016-07-22 PL PL16829901T patent/PL3327012T3/pl unknown
- 2016-07-22 CA CA2993134A patent/CA2993134A1/en active Pending
- 2016-07-22 PT PT168299014T patent/PT3327012T/pt unknown
-
2021
- 2021-06-16 CY CY20211100536T patent/CY1124505T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2993134A1 (en) | 2017-02-02 |
| ES2874577T3 (es) | 2021-11-05 |
| CN107849007A (zh) | 2018-03-27 |
| WO2017017301A1 (es) | 2017-02-02 |
| ES2600827B1 (es) | 2017-11-24 |
| MX382563B (es) | 2025-03-13 |
| SI3327012T1 (sl) | 2021-10-29 |
| EP3327012A4 (en) | 2018-12-19 |
| PL3327012T3 (pl) | 2021-11-22 |
| JP2018522945A (ja) | 2018-08-16 |
| RU2018104258A3 (enExample) | 2019-12-25 |
| CN107849007B (zh) | 2024-08-09 |
| EP3327012B1 (en) | 2021-03-17 |
| LT3327012T (lt) | 2021-09-10 |
| BR112018001225A2 (pt) | 2018-09-11 |
| KR20180036722A (ko) | 2018-04-09 |
| ES2600827A1 (es) | 2017-02-10 |
| ES2600827A8 (es) | 2017-06-15 |
| RU2018104258A (ru) | 2019-08-26 |
| KR102657147B1 (ko) | 2024-04-12 |
| PT3327012T (pt) | 2021-06-21 |
| JP7168447B2 (ja) | 2022-11-09 |
| CY1124505T1 (el) | 2022-07-22 |
| MX2018000883A (es) | 2018-08-15 |
| EP3327012A1 (en) | 2018-05-30 |
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