ES2573299T3 - Derivados de piperazina tiazol útiles en el tratamiento de tauopatías tales como la enfermedad de Alzheimer - Google Patents
Derivados de piperazina tiazol útiles en el tratamiento de tauopatías tales como la enfermedad de Alzheimer Download PDFInfo
- Publication number
- ES2573299T3 ES2573299T3 ES12756402.9T ES12756402T ES2573299T3 ES 2573299 T3 ES2573299 T3 ES 2573299T3 ES 12756402 T ES12756402 T ES 12756402T ES 2573299 T3 ES2573299 T3 ES 2573299T3
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- Prior art keywords
- ethyl
- phenyl
- thiadiazol
- piperazine
- difluoro
- Prior art date
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- 208000024827 Alzheimer disease Diseases 0.000 title claims description 18
- 238000011282 treatment Methods 0.000 title claims description 14
- 208000034799 Tauopathies Diseases 0.000 title description 8
- SQCOTEVTVMIEIC-UHFFFAOYSA-N piperazine;1,3-thiazole Chemical class C1=CSC=N1.C1CNCCN1 SQCOTEVTVMIEIC-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 186
- -1 tetrahydropyran-4-yl Chemical group 0.000 claims abstract description 181
- 150000002367 halogens Chemical group 0.000 claims abstract description 180
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 134
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims abstract description 33
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 32
- 125000001424 substituent group Chemical group 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- WAVNYVVEHJJGGJ-UHFFFAOYSA-N 3-cyclohexyl-5-[4-[2-(4-methoxyphenyl)ethyl]piperazin-1-yl]-1,2,4-thiadiazole Chemical compound C1=CC(OC)=CC=C1CCN1CCN(C=2SN=C(N=2)C2CCCCC2)CC1 WAVNYVVEHJJGGJ-UHFFFAOYSA-N 0.000 claims abstract description 10
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- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- NZNCFXIIEOHIQT-UHFFFAOYSA-N 3-cyclohexyl-5-[4-[2-(3-methoxyphenyl)ethyl]piperazin-1-yl]-1,2,4-thiadiazole Chemical compound COC1=CC=CC(CCN2CCN(CC2)C=2SN=C(N=2)C2CCCCC2)=C1 NZNCFXIIEOHIQT-UHFFFAOYSA-N 0.000 claims abstract description 6
- OLGUNEMEKPJVTK-UHFFFAOYSA-N 3-cyclopropyl-5-[4-[2-(3-methoxyphenyl)ethyl]piperazin-1-yl]-1,2,4-thiadiazole Chemical compound COC1=CC=CC(CCN2CCN(CC2)C=2SN=C(N=2)C2CC2)=C1 OLGUNEMEKPJVTK-UHFFFAOYSA-N 0.000 claims abstract description 5
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 20
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- JNMBEQVBTVHKSO-UHFFFAOYSA-N 3-(4,4-difluoropiperidin-1-yl)-5-[4-[2-(4-methoxyphenyl)ethyl]piperazin-1-yl]-1,2,4-thiadiazole Chemical compound C1=CC(OC)=CC=C1CCN1CCN(C=2SN=C(N=2)N2CCC(F)(F)CC2)CC1 JNMBEQVBTVHKSO-UHFFFAOYSA-N 0.000 claims description 13
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- JXCKUPKPRLUIQX-UHFFFAOYSA-N 5-[4-[2-(3,4-difluorophenyl)ethyl]piperazin-1-yl]-3-(4,4-difluoropiperidin-1-yl)-1,2,4-thiadiazole Chemical compound C1=C(F)C(F)=CC=C1CCN1CCN(C=2SN=C(N=2)N2CCC(F)(F)CC2)CC1 JXCKUPKPRLUIQX-UHFFFAOYSA-N 0.000 claims description 8
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- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 8
- JCLIIXKOVPCLDA-UHFFFAOYSA-N n-(cyclopropylmethyl)-5-[4-[2-(3,4-difluorophenyl)ethyl]piperazin-1-yl]-1,2,4-thiadiazol-3-amine Chemical compound C1=C(F)C(F)=CC=C1CCN1CCN(C=2SN=C(NCC3CC3)N=2)CC1 JCLIIXKOVPCLDA-UHFFFAOYSA-N 0.000 claims description 8
- HILGKYQSOSBIDD-UHFFFAOYSA-N 5-[4-[2-(3,4-difluorophenyl)ethyl]piperazin-1-yl]-3-(oxan-4-yl)-1,2,4-thiadiazole Chemical compound C1=C(F)C(F)=CC=C1CCN1CCN(C=2SN=C(N=2)C2CCOCC2)CC1 HILGKYQSOSBIDD-UHFFFAOYSA-N 0.000 claims description 7
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- DZUNLEMJMDGDBY-UHFFFAOYSA-N 5-[4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-3-[4-(trifluoromethyl)piperidin-1-yl]-1,2,4-thiadiazole Chemical compound C1CC(C(F)(F)F)CCN1C1=NSC(N2CCN(CCC=3C=CC(Cl)=CC=3)CC2)=N1 DZUNLEMJMDGDBY-UHFFFAOYSA-N 0.000 claims description 7
- QJEWVIQTNFMEPI-UHFFFAOYSA-N 5-[4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-n-(cyclopropylmethyl)-1,2,4-thiadiazol-3-amine Chemical compound C1=CC(Cl)=CC=C1CCN1CCN(C=2SN=C(NCC3CC3)N=2)CC1 QJEWVIQTNFMEPI-UHFFFAOYSA-N 0.000 claims description 7
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- 230000008569 process Effects 0.000 claims description 7
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- YEFCKUSLRGHUOF-UHFFFAOYSA-N 5-[4-[2-(3,4-difluorophenyl)ethyl]piperazin-1-yl]-n-[4-(trifluoromethyl)cyclohexyl]-1,2,4-thiadiazol-3-amine Chemical compound C1=C(F)C(F)=CC=C1CCN1CCN(C=2SN=C(NC3CCC(CC3)C(F)(F)F)N=2)CC1 YEFCKUSLRGHUOF-UHFFFAOYSA-N 0.000 claims description 6
- IKRRSWSXAOBWAT-UHFFFAOYSA-N 5-[4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-n-(oxan-4-yl)-1,2,4-thiadiazol-3-amine Chemical compound C1=CC(Cl)=CC=C1CCN1CCN(C=2SN=C(NC3CCOCC3)N=2)CC1 IKRRSWSXAOBWAT-UHFFFAOYSA-N 0.000 claims description 6
- AKIIDXSWHDAZEQ-UHFFFAOYSA-N 5-[4-[2-(4-methoxyphenyl)ethyl]piperazin-1-yl]-3-(oxan-4-yl)-1,2,4-thiadiazole Chemical compound C1=CC(OC)=CC=C1CCN1CCN(C=2SN=C(N=2)C2CCOCC2)CC1 AKIIDXSWHDAZEQ-UHFFFAOYSA-N 0.000 claims description 6
- MIHBBNWDWBWWDR-UHFFFAOYSA-N 3-butyl-5-[4-[2-(3-methoxyphenyl)ethyl]piperazin-1-yl]-1,2,4-thiadiazole Chemical compound CCCCC1=NSC(N2CCN(CCC=3C=C(OC)C=CC=3)CC2)=N1 MIHBBNWDWBWWDR-UHFFFAOYSA-N 0.000 claims description 5
- GYKDRKHTTQCQJD-UHFFFAOYSA-N 5-[4-[2-(3,4-difluorophenyl)ethyl]piperazin-1-yl]-3-(4-fluoropiperidin-1-yl)-1,2,4-thiadiazole Chemical compound C1CC(F)CCN1C1=NSC(N2CCN(CCC=3C=C(F)C(F)=CC=3)CC2)=N1 GYKDRKHTTQCQJD-UHFFFAOYSA-N 0.000 claims description 5
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- 230000007246 mechanism Effects 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
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- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
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- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 208000033510 neuroaxonal dystrophy Diseases 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 208000002593 pantothenate kinase-associated neurodegeneration Diseases 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
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- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11177742 | 2011-08-17 | ||
| EP11177742 | 2011-08-17 | ||
| PCT/EP2012/066136 WO2013024168A1 (en) | 2011-08-17 | 2012-08-17 | Piperazine thiazole derivatives useful in the treatment of tauopathies such as alzheimer's disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2573299T3 true ES2573299T3 (es) | 2016-06-07 |
Family
ID=46826450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12756402.9T Active ES2573299T3 (es) | 2011-08-17 | 2012-08-17 | Derivados de piperazina tiazol útiles en el tratamiento de tauopatías tales como la enfermedad de Alzheimer |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9187440B2 (https=) |
| EP (1) | EP2744798B1 (https=) |
| JP (1) | JP6051218B2 (https=) |
| CN (1) | CN103649062B (https=) |
| AU (1) | AU2012296804B2 (https=) |
| CA (1) | CA2841037C (https=) |
| ES (1) | ES2573299T3 (https=) |
| PL (1) | PL2744798T3 (https=) |
| WO (1) | WO2013024168A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2744798T3 (pl) * | 2011-08-17 | 2016-08-31 | Remynd Nv | Pochodne tiazolu piperazyny użyteczne w leczeniu tauopatii, takich jak choroba alzheimera |
| WO2015140130A1 (en) * | 2014-03-17 | 2015-09-24 | Remynd Nv | Oxadiazole compounds |
| WO2025104092A1 (en) * | 2023-11-13 | 2025-05-22 | Remynd N.V. | Modulators of septin 6 for use in the prevention and/or treatment of neurodegenerative disorders |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004032567A1 (de) | 2004-07-05 | 2006-03-02 | Grünenthal GmbH | Substituierte 1-Propiolyl-piperazine |
| AU2005324024B2 (en) * | 2005-01-07 | 2011-02-17 | F. Hoffmann-La Roche Ag | [4-(Heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (GlyT-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| EP1705474B1 (en) | 2005-03-21 | 2010-04-28 | F.Hoffmann-La Roche Ag | Method for determining lipophilicity |
| PE20070099A1 (es) * | 2005-06-30 | 2007-02-06 | Janssen Pharmaceutica Nv | N-heteroarilpiperazinil ureas como moduladores de la amida hidrolasa del acido graso |
| GB0602335D0 (en) * | 2006-02-07 | 2006-03-15 | Remynd Nv | Thiadiazole Derivatives For The Treatment Of Neurodegenerative Diseases |
| CA2676715A1 (en) * | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
| EP2726470B1 (en) * | 2011-07-01 | 2015-04-29 | reMynd NV | 1,2,4-thiadiazol-5-ylpiperazine derivatives useful in the treatment of neurodegenerative diseases |
| PL2744798T3 (pl) | 2011-08-17 | 2016-08-31 | Remynd Nv | Pochodne tiazolu piperazyny użyteczne w leczeniu tauopatii, takich jak choroba alzheimera |
-
2012
- 2012-08-17 PL PL12756402T patent/PL2744798T3/pl unknown
- 2012-08-17 ES ES12756402.9T patent/ES2573299T3/es active Active
- 2012-08-17 JP JP2014525462A patent/JP6051218B2/ja not_active Expired - Fee Related
- 2012-08-17 US US14/238,905 patent/US9187440B2/en active Active
- 2012-08-17 CN CN201280034129.3A patent/CN103649062B/zh not_active Expired - Fee Related
- 2012-08-17 EP EP12756402.9A patent/EP2744798B1/en active Active
- 2012-08-17 WO PCT/EP2012/066136 patent/WO2013024168A1/en not_active Ceased
- 2012-08-17 CA CA2841037A patent/CA2841037C/en active Active
- 2012-08-17 AU AU2012296804A patent/AU2012296804B2/en not_active Ceased
-
2015
- 2015-10-15 US US14/884,689 patent/US9808456B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HK1192848A1 (zh) | 2014-09-05 |
| US20140206699A1 (en) | 2014-07-24 |
| US9187440B2 (en) | 2015-11-17 |
| CA2841037C (en) | 2020-03-31 |
| US9808456B2 (en) | 2017-11-07 |
| JP6051218B2 (ja) | 2016-12-27 |
| JP2014521737A (ja) | 2014-08-28 |
| AU2012296804A1 (en) | 2014-01-30 |
| US20160101102A1 (en) | 2016-04-14 |
| WO2013024168A1 (en) | 2013-02-21 |
| CA2841037A1 (en) | 2013-02-21 |
| PL2744798T3 (pl) | 2016-08-31 |
| AU2012296804B2 (en) | 2017-04-20 |
| CN103649062B (zh) | 2015-10-07 |
| CN103649062A (zh) | 2014-03-19 |
| EP2744798B1 (en) | 2016-03-30 |
| EP2744798A1 (en) | 2014-06-25 |
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