IL226912A - The history of triazole, their preparation and their pharmaceutical preparations - Google Patents
The history of triazole, their preparation and their pharmaceutical preparationsInfo
- Publication number
- IL226912A IL226912A IL226912A IL22691213A IL226912A IL 226912 A IL226912 A IL 226912A IL 226912 A IL226912 A IL 226912A IL 22691213 A IL22691213 A IL 22691213A IL 226912 A IL226912 A IL 226912A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- hal
- denotes
- crc6
- cycloalkyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims 7
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 66
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 39
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000002619 bicyclic group Chemical group 0.000 claims 24
- 125000004432 carbon atom Chemical group C* 0.000 claims 24
- 125000002950 monocyclic group Chemical group 0.000 claims 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 20
- 125000005842 heteroatom Chemical group 0.000 claims 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 20
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 229920006395 saturated elastomer Polymers 0.000 claims 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 201000006417 multiple sclerosis Diseases 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000003003 spiro group Chemical group 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 6
- 150000004677 hydrates Chemical class 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 4
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- 208000015943 Coeliac disease Diseases 0.000 claims 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims 4
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 4
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 4
- 208000005777 Lupus Nephritis Diseases 0.000 claims 4
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 4
- 229910003827 NRaRb Inorganic materials 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 4
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 4
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 4
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 4
- 206010042953 Systemic sclerosis Diseases 0.000 claims 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 4
- 208000002552 acute disseminated encephalomyelitis Diseases 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 2
- 208000007815 Acquired Hyperostosis Syndrome Diseases 0.000 claims 2
- 208000026872 Addison Disease Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010001935 American trypanosomiasis Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 2
- 208000023328 Basedow disease Diseases 0.000 claims 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 2
- 208000005024 Castleman disease Diseases 0.000 claims 2
- 208000024699 Chagas disease Diseases 0.000 claims 2
- 206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- 208000007465 Giant cell arteritis Diseases 0.000 claims 2
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 2
- 208000015023 Graves' disease Diseases 0.000 claims 2
- 208000001204 Hashimoto Disease Diseases 0.000 claims 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 2
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 2
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 2
- 208000010159 IgA glomerulonephritis Diseases 0.000 claims 2
- 206010021263 IgA nephropathy Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 102100026018 Interleukin-1 receptor antagonist protein Human genes 0.000 claims 2
- 101710144554 Interleukin-1 receptor antagonist protein Proteins 0.000 claims 2
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 2
- 208000000209 Isaacs syndrome Diseases 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 208000011200 Kawasaki disease Diseases 0.000 claims 2
- 208000000185 Localized scleroderma Diseases 0.000 claims 2
- 208000003250 Mixed connective tissue disease Diseases 0.000 claims 2
- 206010027982 Morphoea Diseases 0.000 claims 2
- 206010072359 Neuromyotonia Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010034277 Pemphigoid Diseases 0.000 claims 2
- 201000011152 Pemphigus Diseases 0.000 claims 2
- 208000031845 Pernicious anaemia Diseases 0.000 claims 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 2
- 201000004854 SAPHO syndrome Diseases 0.000 claims 2
- 201000010848 Schnitzler Syndrome Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 2
- 206010072148 Stiff-Person syndrome Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 2
- 241000223109 Trypanosoma cruzi Species 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 206010047115 Vasculitis Diseases 0.000 claims 2
- 206010047642 Vitiligo Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 208000004631 alopecia areata Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 2
- 208000027625 autoimmune inner ear disease Diseases 0.000 claims 2
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 2
- 208000000594 bullous pemphigoid Diseases 0.000 claims 2
- 208000002849 chondrocalcinosis Diseases 0.000 claims 2
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims 2
- 208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 201000001981 dermatomyositis Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000002557 hidradenitis Diseases 0.000 claims 2
- 201000007162 hidradenitis suppurativa Diseases 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- -1 methoxy, hydroxy Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 206010072221 mevalonate kinase deficiency Diseases 0.000 claims 2
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 2
- 208000005987 polymyositis Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- 206010043207 temporal arteritis Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims 1
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000002018 overexpression Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
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- 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
- A61K31/445—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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- 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
- A61K31/537—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 spiro-condensed or forming part of bridged ring systems
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- 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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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D403/14—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 three or more hetero rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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| US201061424890P | 2010-12-20 | 2010-12-20 | |
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| PCT/EP2011/073015 WO2012084704A1 (en) | 2010-12-20 | 2011-12-16 | Indazolyl triazole derivatives as irak inhibitors |
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| US9643955B2 (en) | 2012-12-20 | 2017-05-09 | Merck Sharp & Dohme Corp. | 2-pyridyloxy-3-nitrile-4-substituted orexin receptor antagonists |
| WO2014099697A1 (en) * | 2012-12-20 | 2014-06-26 | Merck Sharp & Dohme Corp. | 3-ester-4-substituted orexin receptor antagonists |
| HUE032863T2 (en) * | 2013-02-07 | 2017-11-28 | Merck Patent Gmbh | Piridazinonamid derivatives |
| HRP20171302T1 (hr) * | 2013-02-07 | 2017-10-20 | Merck Patent Gmbh | Makrociklički derivati piridazinona |
| PH12015502383B1 (en) | 2013-04-19 | 2023-02-03 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| TWI667233B (zh) | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| EP3092226B1 (en) * | 2014-01-10 | 2019-03-13 | Aurigene Discovery Technologies Limited | Indazole compounds as irak4 inhibitors |
| LT3466955T (lt) | 2014-01-13 | 2021-02-25 | Aurigene Discovery Technologies Limited | Oksazol[4,5-b]piridino ir tiazol[4,5-b]piridino darinių, kaip irak4 inhibitorių, skirtų vėžio gydymui, gamybos būdas |
| US9969749B2 (en) | 2014-09-30 | 2018-05-15 | Merck Sharp & Dohme Corp. | Inhibitors of IRAK4 activity |
| EP3200790B1 (en) * | 2014-09-30 | 2020-08-26 | Merck Sharp & Dohme Corp. | Inhibitors of irak4 activity |
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| JO3705B1 (ar) * | 2014-11-26 | 2021-01-31 | Bayer Pharma AG | إندازولات مستبدلة جديدة، عمليات لتحضيرها، مستحضرات دوائية تحتوي عليها واستخدامها في إنتاج أدوية |
| EP3233840B1 (en) | 2014-12-16 | 2018-11-21 | Eudendron S.r.l. | Heterocyclic derivatives modulating activity of certain protein kinases |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
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| US11866405B2 (en) | 2020-12-10 | 2024-01-09 | Astrazeneca Ab | Substituted indazoles as IRAK4 inhibitors |
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| KR20240020735A (ko) | 2021-05-07 | 2024-02-15 | 카이메라 쎄라퓨틱스 인코포레이티드 | Cdk2 분해제 및 그 용도 |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
| BR112023025403A2 (pt) | 2021-06-25 | 2024-02-20 | Korea Res Inst Chemical Tech | Composto heterocíclico bifuncional tendo função de degradação de btk por meio da via ubiquitina proteassoma e uso do mesmo |
| CA3236265A1 (en) | 2021-10-29 | 2023-05-04 | William Leong | Irak4 degraders and synthesis thereof |
| CA3243560A1 (en) | 2022-01-31 | 2023-08-03 | Kymera Therapeutics, Inc. | Iraqi Degradation Agents and Their Uses |
| IL315677A (en) | 2022-03-23 | 2024-11-01 | Rigel Pharmaceuticals Inc | Pyrimid-2-yl-pyrazole compounds as irak inhibitors |
| KR102607237B1 (ko) * | 2023-06-07 | 2023-11-30 | 주식회사 젠센 | 신규한 트리아졸이 치환된 인다졸 유도체 및 이의 용도 |
| CN121816348A (zh) * | 2023-08-11 | 2026-04-07 | 深圳众格生物科技有限公司 | 一种降解irak4的蛋白降解靶向嵌合体化合物及其应用 |
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| US20040087642A1 (en) * | 2002-10-24 | 2004-05-06 | Zeldis Jerome B. | Methods of using and compositions comprising a JNK inhibitor for the treatment, prevention, management and/or modification of pain |
| ZA200503242B (en) * | 2002-10-24 | 2006-10-25 | Celgene Corp | Treatment of pain with JNK inhibitors |
| US20050090529A1 (en) | 2003-07-31 | 2005-04-28 | Pfizer Inc | 3,5 Disubstituted indazole compounds with nitrogen-bearing 5-membered heterocycles, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation |
| US6984652B2 (en) * | 2003-09-05 | 2006-01-10 | Warner-Lambert Company Llc | Gyrase inhibitors |
| CA2606110A1 (en) * | 2005-04-29 | 2006-12-07 | Celgene Corporation | Solid forms of 1-(5-(1h-1,2,4-triazol-5-yl)(1h-indazol-3-yl))-3-(2-piperidylethoxy)benzene |
| MX2009013213A (es) | 2007-06-08 | 2010-03-30 | Abbott Lab | Indazoles 5-sustituidos 5-heteroarilo como inhibidores de cinasa. |
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| AU2011347711B2 (en) | 2017-02-02 |
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| HRP20161127T1 (hr) | 2016-11-18 |
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| EP2655357A1 (en) | 2013-10-30 |
| BR112013015460A2 (pt) | 2016-09-20 |
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| BR112013015460B1 (pt) | 2022-01-25 |
| RS55165B1 (sr) | 2017-01-31 |
| HUE029617T2 (en) | 2017-03-28 |
| AU2011347711A1 (en) | 2013-08-01 |
| KR101842098B1 (ko) | 2018-03-26 |
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