TW201412720A - 三（雜）芳基吡唑及其應用 - Google Patents
三（雜）芳基吡唑及其應用 Download PDFInfo
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- TW201412720A TW201412720A TW102129567A TW102129567A TW201412720A TW 201412720 A TW201412720 A TW 201412720A TW 102129567 A TW102129567 A TW 102129567A TW 102129567 A TW102129567 A TW 102129567A TW 201412720 A TW201412720 A TW 201412720A
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- Prior art keywords
- group
- compound
- alkyl
- alkoxy
- halogen
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- JUHMHPOXZAYYJP-UHFFFAOYSA-N ethyl 5-amino-1-(4-methylphenyl)sulfonylpyrazole-4-carboxylate Chemical class NC1=C(C(=O)OCC)C=NN1S(=O)(=O)C1=CC=C(C)C=C1 JUHMHPOXZAYYJP-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000007983 Tris buffer Substances 0.000 title abstract 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 abstract description 66
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- 241001465754 Metazoa Species 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 6
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- 230000001177 retroviral effect Effects 0.000 abstract description 2
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 135
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 111
- 150000002367 halogens Chemical group 0.000 description 99
- 229910052736 halogen Inorganic materials 0.000 description 96
- 150000003839 salts Chemical class 0.000 description 74
- 125000001424 substituent group Chemical group 0.000 description 71
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 69
- 229910052799 carbon Inorganic materials 0.000 description 67
- 239000012453 solvate Substances 0.000 description 67
- -1 hydroxy, methoxy, methyl Chemical group 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
- 125000003282 alkyl amino group Chemical group 0.000 description 51
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 51
- 239000000243 solution Substances 0.000 description 51
- 125000000217 alkyl group Chemical group 0.000 description 50
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 48
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 47
- 239000000047 product Substances 0.000 description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 239000002904 solvent Substances 0.000 description 46
- 125000004076 pyridyl group Chemical group 0.000 description 44
- 229910052757 nitrogen Inorganic materials 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 125000003545 alkoxy group Chemical group 0.000 description 42
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 38
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- 125000004093 cyano group Chemical group *C#N 0.000 description 34
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- 241000700605 Viruses Species 0.000 description 31
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 29
- 238000002953 preparative HPLC Methods 0.000 description 29
- 229910052739 hydrogen Inorganic materials 0.000 description 28
- 239000001257 hydrogen Substances 0.000 description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 28
- 238000012360 testing method Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 229910052731 fluorine Inorganic materials 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 23
- 150000002431 hydrogen Chemical class 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
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- 238000003786 synthesis reaction Methods 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 125000000753 cycloalkyl group Chemical group 0.000 description 20
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- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 17
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 17
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 101710122864 Major tegument protein Proteins 0.000 description 15
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- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 14
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 13
- 150000001204 N-oxides Chemical class 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 13
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- 239000000203 mixture Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 11
- XHZWFUVEKDDQPF-UHFFFAOYSA-N 5-bromo-1h-pyrazole Chemical compound BrC1=CC=NN1 XHZWFUVEKDDQPF-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
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- 208000031886 HIV Infections Diseases 0.000 description 9
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- 229930182555 Penicillin Natural products 0.000 description 9
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 9
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 7
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- KUIPQZLHHGZXTI-UHFFFAOYSA-N CC(C)(C)CCCCCCCCCNC(=O)O Chemical compound CC(C)(C)CCCCCCCCCNC(=O)O KUIPQZLHHGZXTI-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
- 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
-
- 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
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
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| WO2015121413A1 (en) * | 2014-02-14 | 2015-08-20 | Aicuris Gmbh & Co. Kg | New active pharmaceutical ingredient combinations with compounds based on tri(hetero)aryl pyrazoles |
| EP3263567A1 (en) * | 2016-07-01 | 2018-01-03 | AiCuris Anti-infective Cures GmbH | Carboxamide-substituted pyrazoles and tri(hetero)aryl-pyrazoles for use in methods of treating and / or preventing cardiovascular diseases and / or comorbidities thereof |
| SG11202009179TA (en) * | 2018-04-04 | 2020-10-29 | Japan Tobacco Inc | Pyrazole compounds substituted with heteroaryl and pharmaceutical use thereof |
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| IL104311A (en) | 1992-02-05 | 1997-07-13 | Fujisawa Pharmaceutical Co | Pyrazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
| FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| US6277847B1 (en) | 1999-04-02 | 2001-08-21 | Fmc Corporation | Herbicidal isoindolinonyl-and 3,4-dihydroisoquinolonyl-substituted heterocycles |
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| ES2326723B1 (es) | 2005-07-15 | 2010-05-11 | Laboratorios Del Dr. Esteve, S.A. | Uso de compuestos de pirazol sustituidos y combinaciones de los mismos para el tratamiento del sindrome metabolico. |
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| GB0516661D0 (en) | 2005-08-13 | 2005-09-21 | Astrazeneca Ab | Therapeutic agents |
| ES2632940T3 (es) | 2005-09-13 | 2017-09-18 | Janssen Pharmaceutica Nv | Derivados de tiazol sustituidos con 2-anilin-4-arilo |
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| DE102012016908A1 (de) | 2012-08-17 | 2014-02-20 | Aicuris Gmbh & Co. Kg | Tris-(Hetero)Aryl-Pyrazole und ihre Verwendung |
| WO2015121413A1 (en) | 2014-02-14 | 2015-08-20 | Aicuris Gmbh & Co. Kg | New active pharmaceutical ingredient combinations with compounds based on tri(hetero)aryl pyrazoles |
-
2012
- 2012-08-17 DE DE102012016908.6A patent/DE102012016908A1/de not_active Withdrawn
-
2013
- 2013-08-15 AR ARP130102907A patent/AR092145A1/es unknown
- 2013-08-16 KR KR20157006414A patent/KR20150042841A/ko not_active Withdrawn
- 2013-08-16 MA MA37928A patent/MA37928A1/fr unknown
- 2013-08-16 NZ NZ704727A patent/NZ704727A/en not_active IP Right Cessation
- 2013-08-16 WO PCT/EP2013/067201 patent/WO2014027112A1/de not_active Ceased
- 2013-08-16 AP AP2015008325A patent/AP2015008325A0/xx unknown
- 2013-08-16 EA EA201500232A patent/EA201500232A1/ru unknown
- 2013-08-16 CA CA2881997A patent/CA2881997A1/en not_active Abandoned
- 2013-08-16 TW TW102129567A patent/TW201412720A/zh unknown
- 2013-08-16 AU AU2013303993A patent/AU2013303993A1/en not_active Abandoned
- 2013-08-16 EP EP13750087.2A patent/EP2885300A1/de not_active Withdrawn
- 2013-08-16 BR BR112015003115A patent/BR112015003115A2/pt not_active IP Right Cessation
- 2013-08-16 PE PE2015000171A patent/PE20150869A1/es not_active Application Discontinuation
- 2013-08-16 US US14/422,191 patent/US9249148B2/en not_active Expired - Fee Related
- 2013-08-16 SG SG11201501183VA patent/SG11201501183VA/en unknown
- 2013-08-16 UA UAA201502210A patent/UA112488C2/uk unknown
- 2013-08-16 MX MX2015002046A patent/MX2015002046A/es unknown
- 2013-08-16 HK HK15112600.0A patent/HK1212327A1/xx unknown
- 2013-08-16 CN CN201380044128.1A patent/CN104684913B/zh not_active Expired - Fee Related
- 2013-08-16 JP JP2015527004A patent/JP2015524835A/ja not_active Ceased
-
2015
- 2015-02-12 TN TNP2015000045A patent/TN2015000045A1/fr unknown
- 2015-02-13 PH PH12015500322A patent/PH12015500322B1/en unknown
- 2015-02-16 ZA ZA2015/01078A patent/ZA201501078B/en unknown
- 2015-02-16 CL CL2015000362A patent/CL2015000362A1/es unknown
- 2015-02-17 CU CUP2015000015A patent/CU20150015A7/es unknown
- 2015-02-17 IL IL237298A patent/IL237298A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MA37928A1 (fr) | 2017-11-30 |
| IL237298A0 (en) | 2015-04-30 |
| CN104684913B (zh) | 2016-11-23 |
| EA201500232A1 (ru) | 2015-07-30 |
| JP2015524835A (ja) | 2015-08-27 |
| AU2013303993A1 (en) | 2015-03-12 |
| UA112488C2 (uk) | 2016-09-12 |
| CA2881997A1 (en) | 2014-02-20 |
| CL2015000362A1 (es) | 2015-07-10 |
| AR092145A1 (es) | 2015-03-25 |
| BR112015003115A2 (pt) | 2017-07-04 |
| PH12015500322A1 (en) | 2015-03-30 |
| PE20150869A1 (es) | 2015-05-27 |
| NZ704727A (en) | 2016-07-29 |
| MX2015002046A (es) | 2015-06-05 |
| AP2015008325A0 (en) | 2015-03-31 |
| CN104684913A (zh) | 2015-06-03 |
| DE102012016908A1 (de) | 2014-02-20 |
| US20150203500A1 (en) | 2015-07-23 |
| EP2885300A1 (de) | 2015-06-24 |
| HK1212327A1 (en) | 2016-06-10 |
| PH12015500322B1 (en) | 2019-03-25 |
| ZA201501078B (en) | 2017-11-29 |
| US9249148B2 (en) | 2016-02-02 |
| WO2014027112A1 (de) | 2014-02-20 |
| TN2015000045A1 (en) | 2016-06-29 |
| KR20150042841A (ko) | 2015-04-21 |
| SG11201501183VA (en) | 2015-05-28 |
| CU20150015A7 (es) | 2015-11-27 |
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