AU2013289381A1 - Method for preparing substituted triazolopyridines - Google Patents
Method for preparing substituted triazolopyridines Download PDFInfo
- Publication number
- AU2013289381A1 AU2013289381A1 AU2013289381A AU2013289381A AU2013289381A1 AU 2013289381 A1 AU2013289381 A1 AU 2013289381A1 AU 2013289381 A AU2013289381 A AU 2013289381A AU 2013289381 A AU2013289381 A AU 2013289381A AU 2013289381 A1 AU2013289381 A1 AU 2013289381A1
- Authority
- AU
- Australia
- Prior art keywords
- pyridin
- triazolo
- amino
- benzamide
- phenyt
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 169
- 150000008523 triazolopyridines Chemical class 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 358
- 238000002360 preparation method Methods 0.000 claims abstract description 54
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 294
- -1 hydroxy- Chemical class 0.000 claims description 244
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 233
- 239000000203 mixture Substances 0.000 claims description 230
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 117
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 114
- 125000005843 halogen group Chemical group 0.000 claims description 84
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 73
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 64
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 41
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 37
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 37
- 150000001412 amines Chemical class 0.000 claims description 28
- 238000005859 coupling reaction Methods 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 18
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- 125000003118 aryl group Chemical group 0.000 claims description 15
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- WUDPYZZMQYKTKW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-[2-[2-methoxy-4-(methylsulfonimidoyl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]acetamide Chemical compound COC1=CC(S(C)(=N)=O)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 WUDPYZZMQYKTKW-UHFFFAOYSA-N 0.000 claims description 2
- UCFBXUOGFYVMQX-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-[2-[4-(hydroxymethyl)-2-methoxyanilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]acetamide Chemical compound COC1=CC(CO)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)CC=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 UCFBXUOGFYVMQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- RKHXDXIJRYGZDL-UHFFFAOYSA-N 4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC(C(=O)N)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 RKHXDXIJRYGZDL-UHFFFAOYSA-N 0.000 claims description 2
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- XLAKONHZQDCIEH-UHFFFAOYSA-N n-(2-fluoroethyl)-4-[[6-[4-[(4-fluorophenyl)methylcarbamoyl]phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3-(2,2,2-trifluoroethoxy)benzamide Chemical compound FC(F)(F)COC1=CC(C(=O)NCCF)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 XLAKONHZQDCIEH-UHFFFAOYSA-N 0.000 claims description 2
- KDYHIHMVASSRMF-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[2-[2-methoxy-4-(methylsulfonimidoyl)anilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide Chemical compound COC1=CC(S(C)(=N)=O)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 KDYHIHMVASSRMF-UHFFFAOYSA-N 0.000 claims description 2
- CRTOFESISWFZAU-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[2-[4-(hydroxymethyl)-2-methoxyanilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]benzamide Chemical compound COC1=CC(CO)=CC=C1NC1=NN2C=C(C=3C=CC(=CC=3)C(=O)NCC=3C=CC(F)=CC=3)C=CC2=N1 CRTOFESISWFZAU-UHFFFAOYSA-N 0.000 claims description 2
- XEHCIJQQJFATFU-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CC=C1 XEHCIJQQJFATFU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 229910014033 C-OH Inorganic materials 0.000 claims 6
- 229910014570 C—OH Inorganic materials 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- ZKSYUNLBFSOENV-UHFFFAOYSA-N N-benzoylethanolamine Natural products OCCNC(=O)C1=CC=CC=C1 ZKSYUNLBFSOENV-UHFFFAOYSA-N 0.000 claims 1
- 102220504163 Testis-specific XK-related protein, Y-linked 2_H31L_mutation Human genes 0.000 claims 1
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- AQWOIRBQLOOZGX-UHFFFAOYSA-N triazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=NN21 AQWOIRBQLOOZGX-UHFFFAOYSA-N 0.000 claims 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12175640 | 2012-07-10 | ||
| EP12175640.7 | 2012-07-10 | ||
| EP12185590.2 | 2012-09-24 | ||
| EP12185590 | 2012-09-24 | ||
| EP13170585.7 | 2013-06-05 | ||
| EP13170585 | 2013-06-05 | ||
| PCT/EP2013/064017 WO2014009219A1 (en) | 2012-07-10 | 2013-07-03 | Method for preparing substituted triazolopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2013289381A1 true AU2013289381A1 (en) | 2015-01-22 |
Family
ID=48793197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013289381A Abandoned AU2013289381A1 (en) | 2012-07-10 | 2013-07-03 | Method for preparing substituted triazolopyridines |
Country Status (24)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160264568A1 (en) * | 2013-06-07 | 2016-09-15 | Bayer Pharma Aktiengesellschaft | Substituted triazolopyridines having activity as mps-1 inhibitors |
| CA2914742A1 (en) | 2013-06-11 | 2014-12-18 | Bayer Pharma Aktiengesellschaft | Handovers with co-operating cells configured to provide coordinated multi-point transmission/reception |
| MX2015017119A (es) * | 2013-06-11 | 2016-04-06 | Bayer Pharma AG | Derivados de prodroga de triazolpiridinas sustituidas. |
| ES2966392T3 (es) | 2015-04-17 | 2024-04-22 | Crossfire Oncology Holding B V | Biomarcadores pronósticos para quimioterapia inhibidora de TTK |
| TW201800408A (zh) | 2016-06-15 | 2018-01-01 | 拜耳製藥公司 | Mps-1抑制劑 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20050009812A1 (en) * | 2001-10-05 | 2005-01-13 | Takuya Seko | Remedies for stress diseases comprising mitochondrial benzodiazepine receptor antagonists |
| JP2007537296A (ja) * | 2004-05-14 | 2007-12-20 | アボット・ラボラトリーズ | 治療薬としてのキナーゼ阻害薬 |
| UA89503C2 (uk) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Заміщені похідні аніліну |
| MX2007004179A (es) * | 2004-10-07 | 2007-06-07 | Warner Lambert Co | Derivados de triazolpiridina como agentes antibacterianos. |
| US20060194823A1 (en) * | 2004-12-22 | 2006-08-31 | Georg Kettschau | Sulfonamido-macrocycles as Tie2 inhibitors and the salts thereof, a pharmaceutical composition comprising these compounds, the method of preparing and the use thereof |
| US7557104B2 (en) * | 2006-06-06 | 2009-07-07 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| EP1870416A1 (en) * | 2006-06-21 | 2007-12-26 | Bayer Schering Pharma Aktiengesellschaft | Sulphonamido-macrocycles as tie2 inhibitors |
| WO2008025821A1 (en) | 2006-08-30 | 2008-03-06 | Cellzome Limited | Triazole derivatives as kinase inhibitors |
| JO3598B1 (ar) * | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| WO2009010530A1 (en) | 2007-07-18 | 2009-01-22 | Novartis Ag | Bicyclic heteroaryl compounds and their use as kinase inhibitors |
| AU2008290330A1 (en) | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | 2-anilinopurin-8-ones as inhibitors of TTK/Mps1 for the treatment of proliferative disorders |
| MX2010002312A (es) | 2007-08-31 | 2010-03-18 | Merck Serono Sa | Compuestos de triazolopiridina y su uso como inhibidores de cinasa reguladora de señal de apoptosis. |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| GB0724342D0 (en) * | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
| WO2009137322A2 (en) * | 2008-05-05 | 2009-11-12 | The Trustees Of The University Of Pennsylvania | Processes for the preparation of biphenyl compounds |
| US20110212053A1 (en) * | 2008-06-19 | 2011-09-01 | Dapeng Qian | Phosphatidylinositol 3 kinase inhibitors |
| US20120041195A1 (en) | 2009-02-13 | 2012-02-16 | Fovea Pharmaceuticals | Heterocyclic compounds |
| WO2010124826A1 (en) | 2009-04-29 | 2010-11-04 | Bayer Schering Pharma Aktiengesellschaft | Substituted imidazoquinoxalines |
| WO2010141360A1 (en) * | 2009-06-05 | 2010-12-09 | Merck Sharp & Dohme Corp. | Biaryl benzotriazole derivatives |
| EP2438066A2 (en) * | 2009-06-05 | 2012-04-11 | Cephalon, Inc. | PREPARATION AND USES OF 1,2,4-TRIAZOLO [1,5a]PYRIDINE DERIVATIVES |
| CA2772790C (en) | 2009-09-04 | 2017-06-27 | Benjamin Bader | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
| EP2343295A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridine derivates |
| EP2343297A1 (en) * | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| EP2343294A1 (en) * | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
| UY33452A (es) * | 2010-06-16 | 2012-01-31 | Bayer Schering Pharma Ag | Triazolopiridinas sustituidas |
| WO2012044567A2 (en) * | 2010-09-30 | 2012-04-05 | Merck Sharp & Dohme Corp. | Imidazole derivatives |
| PL2699575T3 (pl) * | 2011-04-21 | 2015-08-31 | Bayer Ip Gmbh | Triazolopirydyny |
| WO2012160029A1 (en) * | 2011-05-23 | 2012-11-29 | Bayer Intellectual Property Gmbh | Substituted triazolopyridines |
| UA112096C2 (uk) * | 2011-12-12 | 2016-07-25 | Байєр Інтеллектуал Проперті Гмбх | Заміщені триазолопіридини та їх застосування як інгібіторів ttk |
-
2013
- 2013-07-03 IN IN85DEN2015 patent/IN2015DN00085A/en unknown
- 2013-07-03 NZ NZ703020A patent/NZ703020A/en not_active IP Right Cessation
- 2013-07-03 MX MX2015000348A patent/MX2015000348A/es unknown
- 2013-07-03 EP EP13737181.1A patent/EP2872506A1/en not_active Withdrawn
- 2013-07-03 HK HK15107242.4A patent/HK1206731A1/xx unknown
- 2013-07-03 EA EA201590116A patent/EA027544B1/ru not_active IP Right Cessation
- 2013-07-03 KR KR20157000338A patent/KR20150040845A/ko not_active Withdrawn
- 2013-07-03 PE PE2015000017A patent/PE20150354A1/es not_active Application Discontinuation
- 2013-07-03 CN CN201380045913.9A patent/CN104603136B/zh not_active Expired - Fee Related
- 2013-07-03 WO PCT/EP2013/064017 patent/WO2014009219A1/en active Application Filing
- 2013-07-03 CA CA2878481A patent/CA2878481A1/en not_active Abandoned
- 2013-07-03 BR BR112015000308A patent/BR112015000308A2/pt not_active IP Right Cessation
- 2013-07-03 JP JP2015520907A patent/JP6238979B2/ja not_active Expired - Fee Related
- 2013-07-03 AU AU2013289381A patent/AU2013289381A1/en not_active Abandoned
- 2013-07-03 AP AP2014008177A patent/AP3778A/en active
- 2013-07-03 SG SG11201408419QA patent/SG11201408419QA/en unknown
- 2013-07-03 US US14/414,164 patent/US9388177B2/en not_active Expired - Fee Related
-
2014
- 2014-12-15 IL IL236265A patent/IL236265A/en not_active IP Right Cessation
-
2015
- 2015-01-07 TN TNP2015000008A patent/TN2015000008A1/fr unknown
- 2015-01-08 CL CL2015000038A patent/CL2015000038A1/es unknown
- 2015-01-09 CO CO15004251A patent/CO7160002A2/es unknown
- 2015-01-09 CR CR20150006A patent/CR20150006A/es unknown
- 2015-01-09 PH PH12015500061A patent/PH12015500061A1/en unknown
- 2015-01-09 DO DO2015000007A patent/DOP2015000007A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TN2015000008A1 (en) | 2016-06-29 |
| US20150148542A1 (en) | 2015-05-28 |
| US9388177B2 (en) | 2016-07-12 |
| EA201590116A1 (ru) | 2015-07-30 |
| SG11201408419QA (en) | 2015-01-29 |
| AP3778A (en) | 2016-08-31 |
| CO7160002A2 (es) | 2015-01-15 |
| WO2014009219A1 (en) | 2014-01-16 |
| EP2872506A1 (en) | 2015-05-20 |
| CN104603136A (zh) | 2015-05-06 |
| AP2014008177A0 (en) | 2014-12-31 |
| JP2015523372A (ja) | 2015-08-13 |
| IL236265A (en) | 2017-07-31 |
| CR20150006A (es) | 2015-02-16 |
| PE20150354A1 (es) | 2015-03-21 |
| JP6238979B2 (ja) | 2017-11-29 |
| NZ703020A (en) | 2017-08-25 |
| MX2015000348A (es) | 2015-04-14 |
| IL236265A0 (en) | 2015-02-26 |
| HK1206731A1 (en) | 2016-01-15 |
| KR20150040845A (ko) | 2015-04-15 |
| IN2015DN00085A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-05-29 |
| CL2015000038A1 (es) | 2015-03-13 |
| DOP2015000007A (es) | 2015-02-15 |
| CN104603136B (zh) | 2017-06-27 |
| CA2878481A1 (en) | 2014-01-16 |
| EA027544B1 (ru) | 2017-08-31 |
| BR112015000308A2 (pt) | 2017-06-27 |
| PH12015500061A1 (en) | 2015-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |