ES2620316T3 - Cicloalquenopirazoles sustituidos como inhibidores de BUB1 para el tratamiento del cáncer - Google Patents
Cicloalquenopirazoles sustituidos como inhibidores de BUB1 para el tratamiento del cáncer Download PDFInfo
- Publication number
- ES2620316T3 ES2620316T3 ES13721755.0T ES13721755T ES2620316T3 ES 2620316 T3 ES2620316 T3 ES 2620316T3 ES 13721755 T ES13721755 T ES 13721755T ES 2620316 T3 ES2620316 T3 ES 2620316T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- tetrahydrocyclopenta
- hydrogen
- pyrimidin
- pyrazol
- 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.)
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- 206010028980 Neoplasm Diseases 0.000 title claims description 47
- 238000011282 treatment Methods 0.000 title claims description 44
- 201000011510 cancer Diseases 0.000 title description 16
- 239000003112 inhibitor Substances 0.000 title description 6
- 101000896657 Homo sapiens Mitotic checkpoint serine/threonine-protein kinase BUB1 Proteins 0.000 title description 2
- 102100021691 Mitotic checkpoint serine/threonine-protein kinase BUB1 Human genes 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 356
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 159
- 239000001257 hydrogen Substances 0.000 claims abstract description 158
- 150000003839 salts Chemical class 0.000 claims abstract description 102
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 81
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 75
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 64
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
- 125000003277 amino group Chemical group 0.000 claims abstract description 42
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 38
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
- 150000002367 halogens Chemical class 0.000 claims abstract description 35
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 33
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 25
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 21
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims abstract description 19
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- 125000005842 heteroatom Chemical group 0.000 claims abstract description 15
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 14
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- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical group C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims abstract description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 6
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- -1 4-Ethoxy-2,6-difluorobenzyl Chemical group 0.000 claims description 173
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 83
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
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- 239000011737 fluorine Substances 0.000 claims description 14
- XBLVHTDFJBKJLG-UHFFFAOYSA-N nicotinic acid ethyl ester Natural products CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 6
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 5
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
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Classifications
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- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- 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
- A61K31/695—Silicon compounds
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12167690 | 2012-05-11 | ||
| EP12167690 | 2012-05-11 | ||
| PCT/EP2013/059666 WO2013167698A1 (en) | 2012-05-11 | 2013-05-08 | Substituted cycloalkenopyrazoles as bub1 inhibitors for the treatment of cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2620316T3 true ES2620316T3 (es) | 2017-06-28 |
Family
ID=48407563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13721755.0T Active ES2620316T3 (es) | 2012-05-11 | 2013-05-08 | Cicloalquenopirazoles sustituidos como inhibidores de BUB1 para el tratamiento del cáncer |
Country Status (8)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA111754C2 (uk) | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| CA2859779A1 (en) | 2011-12-21 | 2013-06-27 | Bayer Intellectual Property Gmbh | Substituted benzylpyrazoles |
| EP2976334A1 (en) * | 2013-03-21 | 2016-01-27 | Bayer Pharma Aktiengesellschaft | Diaminoheteroaryl substituted indazoles |
| CA2907594A1 (en) * | 2013-03-21 | 2014-09-25 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted indazoles |
| CA2907592A1 (en) * | 2013-03-21 | 2014-09-25 | Bayer Pharma Aktiengesellschaft | 3-heteroaryl substituted indazoles |
| CN105452237A (zh) | 2013-06-21 | 2016-03-30 | 拜耳制药股份公司 | 杂芳基取代的吡唑 |
| WO2014202586A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Diaminoheteroaryl substituted pyrazoles |
| CN105408324A (zh) | 2013-06-21 | 2016-03-16 | 拜耳制药股份公司 | 取代的苄基吡唑 |
| EP3063138A1 (en) | 2013-10-30 | 2016-09-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| US10428044B2 (en) | 2014-06-17 | 2019-10-01 | Bayer Pharma Aktiengesellschaft | 3-amino-1,5,6,7-tetrahydro-4H-indol-4-ones |
| AP2017009803A0 (en) | 2014-09-19 | 2017-03-31 | Bayer Pharma AG | Benzyl substituted indazoles as bub1 inhibitors |
| CA2974853C (en) | 2015-01-28 | 2023-02-21 | Bayer Pharma Aktiengesellschaft | 4h-pyrrolo[3,2-c]pyridin-4-one derivatives |
| CA2989469A1 (en) * | 2015-06-17 | 2016-12-22 | Bayer Pharma Aktiengesellschaft | 3-amino-1,5,6,7-tetrahydro-4h-indol-4-ones |
| JP2018525375A (ja) * | 2015-08-05 | 2018-09-06 | バイエル ファーマ アクチエンゲゼルシャフト | １ｈ−ピロール−３−アミン類 |
| JP2019504826A (ja) * | 2015-12-16 | 2019-02-21 | バイエル ファーマ アクチエンゲゼルシャフト | ヘテロ−１，５，６，７−テトラヒドロ−４ｈ−インドール−４−オン類 |
| WO2017148995A1 (en) | 2016-03-04 | 2017-09-08 | Bayer Pharma Aktiengesellschaft | 1-(pyrimidin-2-yl)-1h-indazoles having bub1 kinase inhibiting activity |
| WO2017157992A1 (en) | 2016-03-18 | 2017-09-21 | Bayer Pharma Aktiengesellschaft | Annulated pyrazoles as bub1 kinase inhibitors for treating proliferative disorders |
| WO2017157991A1 (en) | 2016-03-18 | 2017-09-21 | Bayer Pharma Aktiengesellschaft | 1-alkyl-pyrazoles and -indazoles as bub1 inhibitors for the treatment of hyperproliferative diseases |
| WO2018122168A1 (en) | 2016-12-29 | 2018-07-05 | Bayer Pharma Aktiengesellschaft | Combinations of bub1 kinase and parp inhibitors |
| WO2018158175A1 (en) | 2017-02-28 | 2018-09-07 | Bayer Pharma Aktiengesellschaft | Combination of bub1 inhibitors |
| WO2018206547A1 (en) | 2017-05-12 | 2018-11-15 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and atr inhibitors |
| WO2018215282A1 (en) | 2017-05-26 | 2018-11-29 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and pi3k inhibitors |
| CA3196712A1 (en) | 2020-09-23 | 2022-03-31 | Scorpion Therapeutics, Inc. | Pyrrolo[3,2-c]pyridin-4-one derivatives useful in the treatment of cancer |
| WO2022072645A2 (en) | 2020-09-30 | 2022-04-07 | Scorpion Therapeutics, Inc. | Methods for treating cancer |
| WO2022072634A1 (en) | 2020-09-30 | 2022-04-07 | Scorpion Therapeutics, Inc. | Bicyclic compounds for use in the treatment cancer |
| KR20230107419A (ko) | 2020-10-09 | 2023-07-14 | 스코르피온 테라퓨틱스, 인코퍼레이티드 | 암 치료 방법 |
| WO2022094271A1 (en) | 2020-10-30 | 2022-05-05 | Scorpion Therapeutics, Inc. | Methods for treating cancer |
| WO2022098992A1 (en) | 2020-11-05 | 2022-05-12 | Scorpion Therapeutics, Inc. | Use of macrocyclic compounds in methods of treating cancer |
| WO2022197913A1 (en) | 2021-03-18 | 2022-09-22 | Scorpion Therapeutics, Inc. | Bicyclic derivatives which can be used to treat cancer |
| WO2023173083A1 (en) | 2022-03-11 | 2023-09-14 | Scorpion Therapeutics, Inc. | Tetrahydroindole derivatives as egfr and/or her2 inhibtors useful for the treatment of cancer |
| EP4293019A1 (en) * | 2022-06-13 | 2023-12-20 | Netherlands Translational Research Center Holding B.V. | 4-substituted (1h-benzo[d]imidazol-2-yl)-1h-pyrazoles as bub1 inhibitors useful for treating cancers |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| GB9911053D0 (en) * | 1999-05-12 | 1999-07-14 | Pharmacia & Upjohn Spa | 4,5,6,7-tetrahydroindazole derivatives process for their preparation and their use as antitumour agents |
| JP2003522753A (ja) | 2000-02-10 | 2003-07-29 | ロンザ ア−ゲ− | アルコキシマロン酸ジニトリルの製造方法 |
| WO2002047690A1 (en) * | 2000-12-12 | 2002-06-20 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US20050209252A1 (en) * | 2002-03-29 | 2005-09-22 | Che-Ming Teng | Cancer treatment |
| FR2875230A1 (fr) * | 2004-09-13 | 2006-03-17 | Sanofi Aventis Sa | Derives de pyrazole condense, leur preparation et leur application en therapeutique |
| EP2049106A2 (en) * | 2006-07-14 | 2009-04-22 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2011115804A1 (en) * | 2010-03-17 | 2011-09-22 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| UA111754C2 (uk) * | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| EP2594270A3 (en) * | 2011-11-18 | 2013-07-31 | BIP Patents | The use of sGC stimulators, sGC activators, alone and combinations with PDE5 inhibitors for the treatment of systemic sclerosis (SSc) |
-
2013
- 2013-05-08 JP JP2015510822A patent/JP2015520143A/ja not_active Ceased
- 2013-05-08 EP EP13721755.0A patent/EP2847180B1/en not_active Not-in-force
- 2013-05-08 ES ES13721755.0T patent/ES2620316T3/es active Active
- 2013-05-08 WO PCT/EP2013/059666 patent/WO2013167698A1/en active Application Filing
- 2013-05-08 US US14/400,315 patent/US20150141372A1/en active Granted
- 2013-05-08 CA CA2872933A patent/CA2872933A1/en not_active Abandoned
- 2013-05-08 CN CN201380036066.XA patent/CN104411701B/zh not_active Expired - Fee Related
-
2015
- 2015-09-01 HK HK15108514.3A patent/HK1207861A1/xx unknown
-
2017
- 2017-03-08 US US15/453,679 patent/US20170275267A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2847180A1 (en) | 2015-03-18 |
| CN104411701A (zh) | 2015-03-11 |
| EP2847180B1 (en) | 2017-01-04 |
| US20150141372A1 (en) | 2015-05-21 |
| US20170275267A1 (en) | 2017-09-28 |
| WO2013167698A1 (en) | 2013-11-14 |
| HK1207861A1 (en) | 2016-02-12 |
| JP2015520143A (ja) | 2015-07-16 |
| CA2872933A1 (en) | 2013-11-14 |
| CN104411701B (zh) | 2017-01-18 |
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