ES2721302T3 - Inhibidores de PI3k y mTOR conformacionalmente restringidos - Google Patents
Inhibidores de PI3k y mTOR conformacionalmente restringidos Download PDFInfo
- Publication number
- ES2721302T3 ES2721302T3 ES14786817T ES14786817T ES2721302T3 ES 2721302 T3 ES2721302 T3 ES 2721302T3 ES 14786817 T ES14786817 T ES 14786817T ES 14786817 T ES14786817 T ES 14786817T ES 2721302 T3 ES2721302 T3 ES 2721302T3
- Authority
- ES
- Spain
- Prior art keywords
- cr8r9
- nr5r6
- alkyl
- aryl
- heterocyclyl
- 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.)
- Active
Links
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 title 1
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 abstract 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 4
- 125000006413 ring segment Chemical group 0.000 abstract 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 3
- 239000005977 Ethylene Substances 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004452 carbocyclyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- 101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 abstract 1
- 108091008648 NR7C Proteins 0.000 abstract 1
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61K31/535—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
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—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 sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Compuestos de fórmula (I) e (II), **(Ver fórmula)** y estereoisómeros, isómeros geométricos, tautómeros, solvatos y sales farmacéuticamente aceptables de los mismos, en las que R1 es **(Ver fórmula)** X e Y se seleccionan independientemente del grupo que consiste en C(R8)2, O, S, SO, SO2, y NR7; R3x, R3y, R3z, R3p y R4 se seleccionan independientemente del grupo que consiste en hidrógeno, D, F, Cl, Br, I, alquilo C1-C12, alquenilo C2-C8, alquinilo C2-C8, -(alquileno C1-C12)-(carbociclilo C3-C12), -(alquileno C1- C12)-(heterociclilo que tiene 3-20 átomos en el anillo), -(alquileno C1-C12)-C(=O)-(heterociclilo que tiene 3-20 átomos en el anillo), -(alquileno C1-C12)-(arilo C6-C20) y -(alquileno C1-C12)-(heteroarilo que tiene 5-20 átomos en el anillo), -C(alquil C1-C6)2NR5R6, -(CR8R9)tNR5R6, -(CR8R9)nNR7C(=Z)R8, (CR8R9)nNR7S(O)2R5, - CH(OR5)R6, -(CR8R9)nOR5, -(CR8R9)nS(O)2R5, -(CR8R9)nS(O)2NR5R6, -C(=Z)R5, -C(=Z)OR5, C(=Z)NR5R6, - C(=Z)NR7OR5, -C(=O)NR7S(O)2R5, -C(=O)NR7(CR8R9)mNR5R6, -NO2, -NHR7, -NR7C(=Z)R5, -NR7C(=Z)OR5, -NR7C(=Z)NR5R6, -NR7S(O)2R5, -NR7SO2NR5R6, -S(O)2R5, -S(O)2NR5R6, -SC(=Z)R5, -SC(=Z)OR5, carbociclilo C3-C12, heterociclilo C2-C20, arilo C6-C20, y C1-C=NR7, OR5, -OC(=Z)R5, -OC(=Z)OR5, - OC(=Z)NR5R6, y -OS(O)2(OR5); R4x, R4y, R4z, y R4p se seleccionan independientemente del grupo que consiste en hidrógeno, D, F, Cl, Br, I, alquilo C1-C12, alquenilo C2-C8, alquinilo C2-C8, o uno o dos de R4x, R4y, R4z, y R4p son dos sustituyentes geminales metilo y los demás son hidrógeno, o R4x y R4y, o R4z y R4p forman juntos un anillo de carbociclilo, heterociclilo, arilo o heteroarilo de cinco o seis miembros anular, o R4x y R4y forman juntos etileno o metileno puenteado, R4p y R4z forman juntos etileno o metileno puenteado, o R4y y R4p forman juntos etileno o metileno puenteado; en las que dicho alquilo, alquenilo, alquinilo, carbociclilo, heterociclilo, arilo y heteroarilo están sustituidos opcionalmente con uno o más grupos seleccionados independientemente de F, Cl, Br, I, CN, CF3, NO2, oxo, -C(=Z)R5, -C(=Z)OR5, -C(=Z)NR5R6, -(CR8R9)nNR5R6, -(CR8R9)nC(=Z)NR5R6, -(CR8R9)nC(=Z)OR5, - (CR8R9)nNR7SO2R5, -(CR8R9)nOR5, -(CR8R9)nR5, -(CR8R9)nSO2R5, -NR5R6, -NR7C(=Z)R5, -NR7C(=Z)OR5, - NR7C(=Z)NR5R6, -NR7SO2R5,), -OP(OR5)(OR6), SR5, -S(O)R5, -S(O)2R5. -S(O)2NR5R6, -S(O)(OR5), - S(O)2(OR5), -SC(=Z)R5, -SC(=Z)OR5, -SC(=Z)NR5R6, alquilo C1-C12, alquenilo C2-C8, alquinilo C2-C8, carbociclilo C3-C12, heterociclilo C2-C20, arilo C6-C20, y heteroarilo C1-C20; R5, R6 y R7 se seleccionan independientemente de H, D, alquilo C1-C12, alquenilo C2-C8, alquinilo C3-C8, carbociclilo C3-C12, heterociclilo C2-C20, arilo C6-C20, y heteroarilo C1-C20, o R5 y R6 junto con el nitrógeno al que están unidos forman un anillo heterocíclico C3-C20 que contiene opcionalmente uno o más átomos en el anillo adicionales seleccionados de N, O o S, en las que dicho anillo heterocíclico está opcionalmente sustituido con uno o más grupos seleccionados independientemente de oxo, CF3, F, Cl, Br, I, alquilo C1-C12, alquenilo C2-C8, alquinilo C2-C8, carbociclilo C3-C12, heterociclilo C2-C20, arilo C6-C20 y heteroarilo C1-C20; R8 y R9 se seleccionan independientemente de H, D, alquilo C1-C12, y -(CH2)n-arilo, o R8 y R9 junto con los átomos a los que están unidos forman un anillo carbocíclico C3-C12 saturado o parcialmente insaturado; m es 0, 1, 2, 3, 4, 5 o 6; n es 1, 2, 3, 4, 5, o 6; t es 2, 3, 4, 5 o 6; y R2 se selecciona independientemente de los grupos que consisten en un arilo o heteroarilo monocíclico o bicíclico con 1-6 heteroátomos seleccionados de O, N, S, con 1-4 sustituyentes seleccionados de alquilo C1-C4, D, F, Cl, Br, I, -OR5, -COOH, COOR5, -CONR5R6, -SO2NR5R6, CN, CF3, CHF2, CFH2, OCF3, OCOR5, NR7COR5, NR7SO2R5, NR5R6, SO2R5, SOR5, y SR5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13187386 | 2013-10-04 | ||
| PCT/EP2014/071227 WO2015049369A1 (en) | 2013-10-04 | 2014-10-03 | Conformationally restricted pi3k and mtor inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2721302T3 true ES2721302T3 (es) | 2019-07-30 |
Family
ID=49303818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14786817T Active ES2721302T3 (es) | 2013-10-04 | 2014-10-03 | Inhibidores de PI3k y mTOR conformacionalmente restringidos |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9556203B2 (es) |
| EP (1) | EP3052504B1 (es) |
| JP (1) | JP6426745B2 (es) |
| KR (1) | KR102369925B1 (es) |
| CN (1) | CN105593231B (es) |
| AU (1) | AU2014331049B2 (es) |
| BR (1) | BR112016007122A2 (es) |
| CA (1) | CA2925497C (es) |
| ES (1) | ES2721302T3 (es) |
| HK (1) | HK1220971A1 (es) |
| IL (1) | IL244708B (es) |
| MX (1) | MX364558B (es) |
| PH (1) | PH12016500569B1 (es) |
| RU (1) | RU2669696C2 (es) |
| SG (1) | SG11201602602RA (es) |
| WO (1) | WO2015049369A1 (es) |
| ZA (1) | ZA201602084B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK3389662T3 (da) | 2015-12-16 | 2022-02-28 | Genentech Inc | Fremgangsmåde til fremstilling af tricykliske PI3K-inhibitorforbindelser og fremgangsmåder til anvendelse af disse til behandling af cancer |
| US10722484B2 (en) | 2016-03-09 | 2020-07-28 | K-Gen, Inc. | Methods of cancer treatment |
| ES2863250T3 (es) | 2016-05-18 | 2021-10-11 | Torqur Ag | Tratamiento de trastornos neurológicos |
| CA3049402A1 (en) | 2017-01-06 | 2018-07-12 | Palvella Therapeutics Llc | Anhydrous compositions of mtor inhibitors and methods of use |
| EP3817743A4 (en) | 2018-07-02 | 2022-07-06 | Palvella Therapeutics, Inc. | ANHYDROUS COMPOSITIONS OF MTOR INHIBITORS AND METHODS OF USE |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| AUPO903897A0 (en) | 1997-09-08 | 1997-10-02 | Commonwealth Scientific And Industrial Research Organisation | Organic boronic acid derivatives |
| RU2246496C1 (ru) * | 2003-09-12 | 2005-02-20 | Тец Виктор Вениаминович | Вещество с противовирусной и антибактериальной активностью на основе производных 2,8-дитиоксо-1h-пирано[2,3-d, 6,5-d`] дипиримидина и их 10-аза-аналогов |
| US20060188498A1 (en) * | 2005-02-18 | 2006-08-24 | Genentech, Inc. | Methods of using death receptor agonists and EGFR inhibitors |
| WO2006125179A1 (en) * | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Tricyclic compounds and their uses as therapeutic agents |
| KR20140104060A (ko) * | 2006-10-19 | 2014-08-27 | 시그날 파마소티칼 엘엘씨 | 헤테로아릴 화합물, 이들의 조성물 그리고 단백질 키나아제 억제제로서의 이들의 용도 |
| FR2933983B1 (fr) * | 2008-07-15 | 2010-08-27 | Servier Lab | Nouveaux derives tricycliques,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| TWI378933B (en) * | 2008-10-14 | 2012-12-11 | Daiichi Sankyo Co Ltd | Morpholinopurine derivatives |
| US9475812B2 (en) * | 2011-06-04 | 2016-10-25 | Xuanzhu Pharma Co., Ltd. | Pyridonaphthyridine type dual PI3K and mTOR inhibitor and its preparation and use |
| CN103030653A (zh) * | 2011-09-30 | 2013-04-10 | 上海恒瑞医药有限公司 | 杂芳基并嘧啶类衍生物及其可药用盐、其制备方法及其在医药上的应用 |
-
2014
- 2014-10-03 ES ES14786817T patent/ES2721302T3/es active Active
- 2014-10-03 WO PCT/EP2014/071227 patent/WO2015049369A1/en active Application Filing
- 2014-10-03 MX MX2016004203A patent/MX364558B/es active IP Right Grant
- 2014-10-03 CA CA2925497A patent/CA2925497C/en active Active
- 2014-10-03 JP JP2016546166A patent/JP6426745B2/ja active Active
- 2014-10-03 RU RU2016112164A patent/RU2669696C2/ru active
- 2014-10-03 BR BR112016007122A patent/BR112016007122A2/pt not_active Application Discontinuation
- 2014-10-03 EP EP14786817.8A patent/EP3052504B1/en active Active
- 2014-10-03 AU AU2014331049A patent/AU2014331049B2/en active Active
- 2014-10-03 US US15/026,431 patent/US9556203B2/en active Active
- 2014-10-03 CN CN201480054702.6A patent/CN105593231B/zh active Active
- 2014-10-03 SG SG11201602602RA patent/SG11201602602RA/en unknown
- 2014-10-03 KR KR1020167011969A patent/KR102369925B1/ko active IP Right Grant
-
2016
- 2016-03-22 IL IL244708A patent/IL244708B/en active IP Right Grant
- 2016-03-29 PH PH12016500569A patent/PH12016500569B1/en unknown
- 2016-03-29 ZA ZA2016/02084A patent/ZA201602084B/en unknown
- 2016-07-28 HK HK16109050.0A patent/HK1220971A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL244708A0 (en) | 2016-04-21 |
| WO2015049369A1 (en) | 2015-04-09 |
| NZ718614A (en) | 2021-11-26 |
| EP3052504A1 (en) | 2016-08-10 |
| AU2014331049A1 (en) | 2016-04-28 |
| US20160244463A1 (en) | 2016-08-25 |
| CN105593231A (zh) | 2016-05-18 |
| PH12016500569A1 (en) | 2016-06-13 |
| BR112016007122A2 (pt) | 2017-08-01 |
| KR20160067946A (ko) | 2016-06-14 |
| JP6426745B2 (ja) | 2018-11-21 |
| EP3052504B1 (en) | 2019-02-06 |
| PH12016500569B1 (en) | 2016-06-13 |
| AU2014331049B2 (en) | 2018-03-29 |
| KR102369925B1 (ko) | 2022-03-03 |
| JP2016531947A (ja) | 2016-10-13 |
| CA2925497A1 (en) | 2015-04-09 |
| RU2016112164A (ru) | 2017-11-09 |
| RU2016112164A3 (es) | 2018-05-22 |
| US9556203B2 (en) | 2017-01-31 |
| IL244708B (en) | 2019-06-30 |
| ZA201602084B (en) | 2017-05-31 |
| CA2925497C (en) | 2022-12-06 |
| CN105593231B (zh) | 2018-06-05 |
| MX2016004203A (es) | 2016-12-16 |
| MX364558B (es) | 2019-04-29 |
| SG11201602602RA (en) | 2016-04-28 |
| HK1220971A1 (zh) | 2017-05-19 |
| RU2669696C2 (ru) | 2018-10-15 |
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