HRP20221356T1 - Nova alkilirajuća sredstva - Google Patents
Nova alkilirajuća sredstva Download PDFInfo
- Publication number
- HRP20221356T1 HRP20221356T1 HRP20221356TT HRP20221356T HRP20221356T1 HR P20221356 T1 HRP20221356 T1 HR P20221356T1 HR P20221356T T HRP20221356T T HR P20221356TT HR P20221356 T HRP20221356 T HR P20221356T HR P20221356 T1 HRP20221356 T1 HR P20221356T1
- Authority
- HR
- Croatia
- Prior art keywords
- indol
- carbonyl
- thieno
- chloromethyl
- dihydro
- Prior art date
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- 229940100198 alkylating agent Drugs 0.000 title 1
- 239000002168 alkylating agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 3
- IIHLTOJHVNXPRZ-VZYDHVRKSA-N Cl.CN1CCN(CC1)C(=O)Oc1cc2N(C[C@@H](CCl)c2c2c(C)csc12)C(=O)c1cc2cc(NC(=O)c3cc4cc(N)ccc4[nH]3)ccc2[nH]1 Chemical compound Cl.CN1CCN(CC1)C(=O)Oc1cc2N(C[C@@H](CCl)c2c2c(C)csc12)C(=O)c1cc2cc(NC(=O)c3cc4cc(N)ccc4[nH]3)ccc2[nH]1 IIHLTOJHVNXPRZ-VZYDHVRKSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- IIHLTOJHVNXPRZ-FTBISJDPSA-N [(8r)-6-[5-[(5-amino-1h-indole-2-carbonyl)amino]-1h-indole-2-carbonyl]-8-(chloromethyl)-1-methyl-7,8-dihydrothieno[3,2-e]indol-4-yl] 4-methylpiperazine-1-carboxylate;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)OC(C=1SC=C(C)C=11)=CC2=C1[C@@H](CCl)CN2C(=O)C1=CC2=CC(NC(=O)C=3NC4=CC=C(N)C=C4C=3)=CC=C2N1 IIHLTOJHVNXPRZ-FTBISJDPSA-N 0.000 claims 1
- OGFLYTUKSKXWFD-VWLOTQADSA-N [(8r)-8-(chloromethyl)-1-methyl-6-[5-[[5-[(2-methylpropan-2-yl)oxycarbonylamino]-1h-indole-2-carbonyl]amino]-1h-indole-2-carbonyl]-7,8-dihydrothieno[3,2-e]indol-4-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC(C=1SC=C(C)C=11)=CC2=C1[C@@H](CCl)CN2C(=O)C1=CC2=CC(NC(=O)C=3NC4=CC=C(NC(=O)OC(C)(C)C)C=C4C=3)=CC=C2N1 OGFLYTUKSKXWFD-VWLOTQADSA-N 0.000 claims 1
- DLGMWIQPGAEPPC-SFHVURJKSA-N [(8r)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydrothieno[3,2-e]indol-6-yl]-[5-(2-pyrrolidin-1-ylethoxy)-1h-indol-2-yl]methanone Chemical compound C1([C@@H](CCl)C2)=C3C(C)=CSC3=C(O)C=C1N2C(=O)C(NC1=CC=2)=CC1=CC=2OCCN1CCCC1 DLGMWIQPGAEPPC-SFHVURJKSA-N 0.000 claims 1
- OGFLYTUKSKXWFD-RUZDIDTESA-N [(8s)-8-(chloromethyl)-1-methyl-6-[5-[[5-[(2-methylpropan-2-yl)oxycarbonylamino]-1h-indole-2-carbonyl]amino]-1h-indole-2-carbonyl]-7,8-dihydrothieno[3,2-e]indol-4-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC(C=1SC=C(C)C=11)=CC2=C1[C@H](CCl)CN2C(=O)C1=CC2=CC(NC(=O)C=3NC4=CC=C(NC(=O)OC(C)(C)C)C=C4C=3)=CC=C2N1 OGFLYTUKSKXWFD-RUZDIDTESA-N 0.000 claims 1
- DLGMWIQPGAEPPC-GOSISDBHSA-N [(8s)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydrothieno[3,2-e]indol-6-yl]-[5-(2-pyrrolidin-1-ylethoxy)-1h-indol-2-yl]methanone Chemical compound C1([C@H](CCl)C2)=C3C(C)=CSC3=C(O)C=C1N2C(=O)C(NC1=CC=2)=CC1=CC=2OCCN1CCCC1 DLGMWIQPGAEPPC-GOSISDBHSA-N 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- VDJKHEMVOXNSNM-HSZRJFAPSA-N n-[2-[(8s)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydrothieno[3,2-e]indole-6-carbonyl]-1h-indol-5-yl]-5-(2-pyrrolidin-1-ylethoxy)-1h-indole-2-carboxamide Chemical compound C1([C@H](CCl)C2)=C3C(C)=CSC3=C(O)C=C1N2C(=O)C(NC1=CC=2)=CC1=CC=2NC(=O)C(NC1=CC=2)=CC1=CC=2OCCN1CCCC1 VDJKHEMVOXNSNM-HSZRJFAPSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- FGZKXOUQTSCULJ-HXUWFJFHSA-N tert-butyl n-[2-[[2-[(8s)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydrothieno[3,2-e]indole-6-carbonyl]-1h-indol-5-yl]carbamoyl]-1h-indol-5-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C2NC(C(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C4=CC(O)=C5SC=C(C5=C4[C@H](CCl)C3)C)=CC2=C1 FGZKXOUQTSCULJ-HXUWFJFHSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/545—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (4)
1. Spoj formule (II)
[image]
izabran iz grupe sastoji se od:
N-(2-{[(8S)-8-(klorometil)-4-hidroksi-1-metil-7,8-dihidro-6H-tieno[3,2-e]indol-6-il]karbonil}-1H-indol-5-il)-5-[2-(pirolidin-1-il)etoksi]-1H-indol-2-karboksamid,
tert-butil{2-[(2-{[(8S)-8-(klorometil)-4-hidroksi-1-metil-7,8-dihidro-6H-tieno[3,2-e]indol-6-il]karbonil}- 1H-indol-5-il)karbamoil]-1H-indol-5-il}karbamat,
(8S)-6-({5-[({5-[(tert-butoksikarbonil)amino]-1H-indol-2-il}karbonil)amino]-1H-indol-2-il}karbonil)-8- (klorometil)-1-metil-7,8-dihidro-6H-tieno[3,2-e]indol-4- il 4-metilpiperazin-1-karboksilat,
(8S)-6-[(5-{[(5-amino-1H-indol-2-il)karbonil]amino}-1H-indol-2-il)karbonil]-8-(klorometil)-1-metil-7,8- dihidro-6H-tieno[3,2-e]indol-4-il 4-metilpiperazin-1-karboksilat hidroklorid,
(8R)-6-({5-[({5-[(tert-butoksikarbonil)amino]-1H-indol-2-il}karbonil)amino]-1H-indol-2-il}karbonil)-8- (klorometil)-1-metil-7,8-dihidro-6H-tieno[3,2-e]indol-4-il 4-metilpiperazin-1-karboksilat,
(8R)-6-[(5-{[(5-amino-1H-indol-2-il)karbonil]amino}-1H-indol-2-il)karbonil]-8-(klorometil)-1-metil-7,8- dihidro-6H-tieno[3,2-e]indol-4-il 4-metilpiperazin-1-karboksilat hidroklorid,
[(8S)-8-(klorometil)-4-hidroksi-1-metil-7,8-dihidro-6H- tieno[3,2-e]indol-6-il]{5-[2-(pirolidin-1-il)etoksi]- 1H-indol-2-il}metanon,
[(8R)-8-(klorometil)-4-hidroksi-1-metil-7,8-dihidro-6H-tieno[3,2-e]indol-6-il]{5-[2-(pirolidin-1-il)etoksi]- 1H-indol-2-il}metanon,
ili njegova farmaceutski prihvatljiva sol.
2. Farmaceutski pripravak koji sadrži terapeutski učinkovitu količinu spoja formule (II), kako je definirano u zahtjevu 1 i najmanje jedno farmaceutski prihvatljivo vezivo, koje uključuje nosač ili razrjeđivač.
3. Farmaceutski pripravak prema zahtjevu 2, nadalje sadrži jedno ili više kemoterapijskih sredstava.
4. Spoj formule (II) prema zahtjevu 1, za uporabu kod liječenja raka.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12163459 | 2012-04-05 | ||
EP12176162 | 2012-07-12 | ||
EP19184082.6A EP3587426B1 (en) | 2012-04-05 | 2013-03-28 | New alkylating agents |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20221356T1 true HRP20221356T1 (hr) | 2022-12-23 |
Family
ID=48092927
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20221356TT HRP20221356T1 (hr) | 2012-04-05 | 2013-03-28 | Nova alkilirajuća sredstva |
Country Status (11)
Country | Link |
---|---|
US (2) | US9527863B2 (hr) |
EP (2) | EP2836494B1 (hr) |
JP (2) | JP6314128B2 (hr) |
CN (2) | CN107011358B (hr) |
DK (1) | DK2836494T3 (hr) |
ES (2) | ES2929759T3 (hr) |
HK (1) | HK1203957A1 (hr) |
HR (1) | HRP20221356T1 (hr) |
HU (1) | HUE060655T2 (hr) |
RU (1) | RU2632206C2 (hr) |
WO (1) | WO2013149948A1 (hr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2929759T3 (es) | 2012-04-05 | 2022-12-01 | Nerviano Medical Sciences Srl | Nuevos agentes alquilantes |
US9561290B2 (en) * | 2012-04-05 | 2017-02-07 | Nerviano Medical Sciences S.R.L. | Functionalized thieno-indole derivatives for the treatment of cancer |
ES2738657T3 (es) * | 2013-09-25 | 2020-01-24 | Nerviano Medical Sciences Srl | Derivados de tieno[2,3-e]indol como nuevos antitumorales |
JP6782250B2 (ja) | 2015-03-20 | 2020-11-11 | ファイザー・インク | Ctiファーマコフォアを含有する二官能性細胞毒性剤 |
EP3325489B1 (en) * | 2015-07-21 | 2019-11-13 | Nerviano Medical Sciences S.R.L. | Asymmetric process for the preparation of thieno-indoles derivatives |
JP6412906B2 (ja) | 2015-11-03 | 2018-10-24 | 財團法人工業技術研究院Industrial Technology Research Institute | 化合物、リンカー−薬物およびリガンド−薬物複合体 |
WO2018035391A1 (en) * | 2016-08-19 | 2018-02-22 | Bristol-Myers Squibb Company | Seco-cyclopropapyrroloindole compounds, antibody-drug conjugates thereof, and methods of making and use |
EP4221705A1 (en) * | 2020-09-09 | 2023-08-09 | Clinuvel (UK) Ltd. | Pyrrolidine compounds to treat xeroderma pigmentosum |
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TWI461428B (zh) | 2008-07-15 | 2014-11-21 | Genentech Inc | 蔥環黴素衍生結合物,其製備方法及作為抗腫瘤化合物之用途 |
US9561290B2 (en) * | 2012-04-05 | 2017-02-07 | Nerviano Medical Sciences S.R.L. | Functionalized thieno-indole derivatives for the treatment of cancer |
ES2929759T3 (es) | 2012-04-05 | 2022-12-01 | Nerviano Medical Sciences Srl | Nuevos agentes alquilantes |
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2013
- 2013-03-28 ES ES19184082T patent/ES2929759T3/es active Active
- 2013-03-28 RU RU2014143994A patent/RU2632206C2/ru active
- 2013-03-28 DK DK13715931T patent/DK2836494T3/da active
- 2013-03-28 ES ES13715931T patent/ES2755719T3/es active Active
- 2013-03-28 WO PCT/EP2013/056743 patent/WO2013149948A1/en active Application Filing
- 2013-03-28 EP EP13715931.5A patent/EP2836494B1/en active Active
- 2013-03-28 JP JP2015503835A patent/JP6314128B2/ja active Active
- 2013-03-28 HU HUE19184082A patent/HUE060655T2/hu unknown
- 2013-03-28 HR HRP20221356TT patent/HRP20221356T1/hr unknown
- 2013-03-28 CN CN201610942350.9A patent/CN107011358B/zh active Active
- 2013-03-28 US US14/390,644 patent/US9527863B2/en active Active
- 2013-03-28 CN CN201380016674.4A patent/CN104220442B/zh active Active
- 2013-03-28 EP EP19184082.6A patent/EP3587426B1/en active Active
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2015
- 2015-05-15 HK HK15104635.6A patent/HK1203957A1/xx unknown
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2016
- 2016-11-23 US US15/359,703 patent/US10071074B2/en active Active
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2017
- 2017-10-13 JP JP2017199656A patent/JP2018070599A/ja not_active Withdrawn
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JP6314128B2 (ja) | 2018-04-18 |
US10071074B2 (en) | 2018-09-11 |
ES2929759T3 (es) | 2022-12-01 |
EP3587426B1 (en) | 2022-08-10 |
RU2632206C2 (ru) | 2017-10-03 |
JP2018070599A (ja) | 2018-05-10 |
EP2836494A1 (en) | 2015-02-18 |
CN104220442A (zh) | 2014-12-17 |
CN107011358A (zh) | 2017-08-04 |
DK2836494T3 (da) | 2019-11-11 |
EP2836494B1 (en) | 2019-08-21 |
US20150051154A1 (en) | 2015-02-19 |
EP3587426A1 (en) | 2020-01-01 |
JP2015514101A (ja) | 2015-05-18 |
CN107011358B (zh) | 2020-05-05 |
HUE060655T2 (hu) | 2023-04-28 |
CN104220442B (zh) | 2016-11-23 |
US9527863B2 (en) | 2016-12-27 |
WO2013149948A1 (en) | 2013-10-10 |
RU2014143994A (ru) | 2016-05-27 |
ES2755719T3 (es) | 2020-04-23 |
US20170071907A1 (en) | 2017-03-16 |
HK1203957A1 (en) | 2015-11-06 |
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