RU2013122898A - Похоксимовые конъюгаты, применимые для лечения связанных с hsp90 патологий, композиция и способ лечения с их помощью - Google Patents
Похоксимовые конъюгаты, применимые для лечения связанных с hsp90 патологий, композиция и способ лечения с их помощью Download PDFInfo
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- RU2013122898A RU2013122898A RU2013122898/04A RU2013122898A RU2013122898A RU 2013122898 A RU2013122898 A RU 2013122898A RU 2013122898/04 A RU2013122898/04 A RU 2013122898/04A RU 2013122898 A RU2013122898 A RU 2013122898A RU 2013122898 A RU2013122898 A RU 2013122898A
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- 238000000034 method Methods 0.000 title claims 5
- 101710113864 Heat shock protein 90 Proteins 0.000 title claims 3
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 title 1
- 230000007170 pathology Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
- 239000001257 hydrogen Substances 0.000 claims abstract 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract 11
- 150000002367 halogens Chemical class 0.000 claims abstract 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000003118 aryl group Chemical group 0.000 claims abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 6
- -1 carbonylamino, aminocarbonyl Chemical group 0.000 claims abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- 239000000651 prodrug Substances 0.000 claims abstract 4
- 229940002612 prodrug Drugs 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 239000012453 solvate Substances 0.000 claims abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000006239 protecting group Chemical group 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 5
- 125000000524 functional group Chemical group 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 201000009030 Carcinoma Diseases 0.000 claims 3
- 230000031018 biological processes and functions Effects 0.000 claims 3
- 239000012634 fragment Substances 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 230000001575 pathological effect Effects 0.000 claims 3
- 230000004962 physiological condition Effects 0.000 claims 3
- 210000000664 rectum Anatomy 0.000 claims 3
- 230000008685 targeting Effects 0.000 claims 3
- 201000005569 Gout Diseases 0.000 claims 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 210000000214 mouth Anatomy 0.000 claims 2
- 210000003800 pharynx Anatomy 0.000 claims 2
- 208000003200 Adenoma Diseases 0.000 claims 1
- 206010001233 Adenoma benign Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010023347 Keratoacanthoma Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 208000013058 Weber syndrome Diseases 0.000 claims 1
- 208000009956 adenocarcinoma Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 210000000013 bile duct Anatomy 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000000133 brain stem Anatomy 0.000 claims 1
- 201000007293 brain stem infarction Diseases 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000002889 endothelial cell Anatomy 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 210000002768 hair cell Anatomy 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000007794 irritation Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000003849 large cell carcinoma Diseases 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- 210000000867 larynx Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000000088 lip Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 201000003142 neovascular glaucoma Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 201000010198 papillary carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 1
- 210000002105 tongue Anatomy 0.000 claims 1
- 208000010576 undifferentiated carcinoma Diseases 0.000 claims 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims 1
- 230000006492 vascular dysfunction Effects 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- 0 C*[C@@](CC=CC(Cc1cc(OC)cc(OC)c11)=*OCC(*2CCCCC2)=O)/C=C/C[C@@](C)OC1=O Chemical compound C*[C@@](CC=CC(Cc1cc(OC)cc(OC)c11)=*OCC(*2CCCCC2)=O)/C=C/C[C@@](C)OC1=O 0.000 description 2
- VZVRACFMIZZMJB-SHWGKNIPSA-N C[C@H](C/C=C/CC/C=C/C(/Cc1c2c(O)cc(O)c1)=N/OCC(N1CCCCC1)=O)OC2=O Chemical compound C[C@H](C/C=C/CC/C=C/C(/Cc1c2c(O)cc(O)c1)=N/OCC(N1CCCCC1)=O)OC2=O VZVRACFMIZZMJB-SHWGKNIPSA-N 0.000 description 1
- ACWNYXNFKMOKCW-QRYNJEAHSA-N C[C@H](C/C=C/[C@@H](C/C=C/C(/Cc1cc(O)cc(O)c11)=N\OCC(N2CCCCC2)=O)NC(C)=O)OC1=O Chemical compound C[C@H](C/C=C/[C@@H](C/C=C/C(/Cc1cc(O)cc(O)c11)=N\OCC(N2CCCCC2)=O)NC(C)=O)OC1=O ACWNYXNFKMOKCW-QRYNJEAHSA-N 0.000 description 1
Classifications
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- 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
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- 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
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- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40588210P | 2010-10-22 | 2010-10-22 | |
| US61/405,882 | 2010-10-22 | ||
| PCT/IB2011/002796 WO2012052843A1 (en) | 2010-10-22 | 2011-10-24 | Pochoxime conjugates useful for the treatment of hsp90 related pathologies |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2013122898A true RU2013122898A (ru) | 2014-11-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013122898/04A RU2013122898A (ru) | 2010-10-22 | 2011-10-24 | Похоксимовые конъюгаты, применимые для лечения связанных с hsp90 патологий, композиция и способ лечения с их помощью |
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| JP (2) | JP2013543840A (https=) |
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| US20140079636A1 (en) | 2012-04-16 | 2014-03-20 | Dinesh U. Chimmanamada | Targeted therapeutics |
| EP3035938B1 (en) * | 2013-09-10 | 2020-08-19 | Madrigal Pharmaceuticals, Inc. | Targeted therapeutics |
| WO2015066053A2 (en) | 2013-10-28 | 2015-05-07 | Synta Pharmaceuticals Corp. | Targeted therapeutics |
| WO2015116774A1 (en) | 2014-01-29 | 2015-08-06 | Synta Pharmaceuticals Corp. | Targeted therapeutics |
| AU2015224576A1 (en) | 2014-03-03 | 2016-09-22 | Madrigal Pharmaceuticals, Inc. | Targeted therapeutics |
| WO2015143004A1 (en) | 2014-03-18 | 2015-09-24 | Synta Pharmaceuticals Corp. | Targeted therapeutics |
| WO2016126726A1 (en) | 2015-02-02 | 2016-08-11 | Forma Therapeutics, Inc. | Bicyclic [4,6,0] hydroxamic acids as hdac6 inhibitors |
| SG11201708622UA (en) | 2015-02-02 | 2017-11-29 | Forma Therapeutics Inc | 3-aryl-4-amido-bicyclic [4,5,0] hydroxamic acids as hdac inhibitors |
| EP3472131B1 (en) | 2016-06-17 | 2020-02-19 | Forma Therapeutics, Inc. | 2-spiro-5- and 6-hydroxamic acid indanes as hdac inhibitors |
| CN110799194A (zh) | 2017-06-20 | 2020-02-14 | 马德里加尔制药公司 | 包含靶向治疗剂的联合疗法 |
| EP3641647A4 (en) | 2017-06-20 | 2021-05-05 | Madrigal Pharmaceuticals, Inc. | TARGETED THERAPEUTICS |
| WO2022082108A1 (en) * | 2020-10-16 | 2022-04-21 | The Brigham And Women's Hospital, Inc. | Compositions for inducing tumor immunity and reducing drug tolerance |
| CN119424412A (zh) * | 2024-12-04 | 2025-02-14 | 中国药科大学 | 以prdx1作为药物靶标的天然抑制剂在制备抗乳腺癌药物中的应用 |
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| US5861156A (en) * | 1993-01-08 | 1999-01-19 | Creative Biomolecules | Methods of delivering agents to target cells |
| US5624677A (en) | 1995-06-13 | 1997-04-29 | Pentech Pharmaceuticals, Inc. | Controlled release of drugs delivered by sublingual or buccal administration |
| PT934065E (pt) * | 1996-08-30 | 2006-10-31 | Univ Hawaii | Compostos farmaceuticos |
| CA2245922A1 (en) * | 1996-12-13 | 1998-06-18 | Shun-Ichi Ikeda | Dc 107 derivatives (2) |
| AU2001271567A1 (en) | 2000-06-29 | 2002-01-14 | Trustees Of Boston University | Use of geldanamycin and related compounds for prophylaxis or treatment of fibrogenic disorders |
| ITRM20010079A1 (it) * | 2001-02-16 | 2002-08-16 | Sigma Tau Ind Farmaceuti | Amminoderivati della biotina e loro coniugati con chelanti macrociclici. |
| TWI381852B (zh) * | 2005-09-27 | 2013-01-11 | Sigma Tau Ind Farmaceuti | 生物素二胺基衍生物類及其與大環螯合劑之共軛物 |
| US8329683B2 (en) * | 2006-06-02 | 2012-12-11 | Nexgenix Pharmaceuticals, Llc | Treatment of neurofibromatosis with radicicol and its derivatives |
| CN103539769B (zh) * | 2006-08-11 | 2016-03-16 | 斯特拉斯堡大学 | 用作激酶抑制剂和hsp90抑制剂的大环化合物 |
| MX2010007755A (es) * | 2008-01-15 | 2010-12-21 | Univ Strasbourg | Sintesis de lactonas de acido resorcilico utiles como agentes terapeuticos. |
| CN102015673B (zh) * | 2008-02-21 | 2014-10-29 | 昂科协同公司 | 用作治疗剂的大环前药化合物 |
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2011
- 2011-10-24 US US13/880,878 patent/US20140031302A1/en not_active Abandoned
- 2011-10-24 BR BR112013009614A patent/BR112013009614A2/pt not_active IP Right Cessation
- 2011-10-24 KR KR1020137012551A patent/KR20140021520A/ko not_active Ceased
- 2011-10-24 CN CN201611152551.5A patent/CN107011311A/zh active Pending
- 2011-10-24 AU AU2011319685A patent/AU2011319685B2/en not_active Ceased
- 2011-10-24 WO PCT/IB2011/002796 patent/WO2012052843A1/en not_active Ceased
- 2011-10-24 CA CA2812320A patent/CA2812320A1/en not_active Abandoned
- 2011-10-24 JP JP2013534404A patent/JP2013543840A/ja active Pending
- 2011-10-24 EP EP11797116.8A patent/EP2630132A1/en not_active Withdrawn
- 2011-10-24 RU RU2013122898/04A patent/RU2013122898A/ru unknown
- 2011-10-24 CN CN2011800601830A patent/CN103370311A/zh active Pending
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2013
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2015
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2016
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- 2016-09-12 JP JP2016177446A patent/JP2017039730A/ja active Pending
Also Published As
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| CA2812320A1 (en) | 2012-04-26 |
| WO2012052843A1 (en) | 2012-04-26 |
| AU2011319685B2 (en) | 2016-02-04 |
| CN107011311A (zh) | 2017-08-04 |
| CN103370311A (zh) | 2013-10-23 |
| IL225371A0 (en) | 2013-06-27 |
| KR20140021520A (ko) | 2014-02-20 |
| AU2011319685A1 (en) | 2013-04-11 |
| BR112013009614A2 (pt) | 2016-07-19 |
| JP2017039730A (ja) | 2017-02-23 |
| EP2630132A1 (en) | 2013-08-28 |
| JP2013543840A (ja) | 2013-12-09 |
| US20170174669A1 (en) | 2017-06-22 |
| US20140031302A1 (en) | 2014-01-30 |
| US20150374680A1 (en) | 2015-12-31 |
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