RU2016142611A - Пролекарственные средства ингибиторов обратной транскриптазы вич - Google Patents
Пролекарственные средства ингибиторов обратной транскриптазы вич Download PDFInfo
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- RU2016142611A RU2016142611A RU2016142611A RU2016142611A RU2016142611A RU 2016142611 A RU2016142611 A RU 2016142611A RU 2016142611 A RU2016142611 A RU 2016142611A RU 2016142611 A RU2016142611 A RU 2016142611A RU 2016142611 A RU2016142611 A RU 2016142611A
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- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- methyl
- hiv
- chloro
- Prior art date
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- 108010078851 HIV Reverse Transcriptase Proteins 0.000 title claims 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title claims 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- -1 5 - ((5- (3-chloro-5-cyanophenoxy) -4- (difluoromethyl) -6-oxopyrimidin-1 (6H) -yl) methyl) -3- (difluoromethyl) -6-oxopyridazin-1 (6H) -yl Chemical group 0.000 claims 8
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims 6
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims 3
- 229940124411 anti-hiv antiviral agent Drugs 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 230000000840 anti-viral effect Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000002835 hiv fusion inhibitor Substances 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims 1
- 229940126252 HIV maturation inhibitor Drugs 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003084 hiv integrase inhibitor Substances 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 239000012678 infectious agent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
-
- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further 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
- A61K31/495—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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further 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
- A61K31/495—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
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Claims (38)
1. Соединение структурной формулы I или его фармацевтически приемлемая соль:
где R 1 представляет собой 
;
R 2 представляет собой галоген или -C1-3-алкил, замещенный 1-3 -F;
R 3 представляет собой (a) галоген, (b) -C1-3-алкил, замещенный 1-3 -F, или (3) фенил, замещенный галогеном; и
R 4 представляет собой 
.
2. Соединение по п. 1 или его фармацевтически приемлемая соль,
где R 1 представляет собой 
.
3. Соединение по п. 1 или его фармацевтически приемлемая соль,
где R 1 представляет собой 
.
4. Соединение по любому из пп. 1-3 или его фармацевтически приемлемая соль,
где R 2 представляет собой метил, замещенный 1, 2 или 3 -F; или этил, замещенный 1, 2 или 3 -F.
5. Соединение по п. 4 или его фармацевтически приемлемая соль,
где R 2 представляет собой -CHF2, -CF3 или -CF2CH3.
6. Соединение по любому из пп. 1-5 или его фармацевтически приемлемая соль,
где R 3 представляет собой -F; -Cl; метил, замещенный 1, 2 или 3 -F; этил, замещенный 1, 2 или 3 -F; или фенил, замещенный -F.
7. Соединение по п. 6 или его фармацевтически приемлемая соль,
где R 3 представляет собой -Cl, -CHF2, -CF3, -CF2CH3 или фенил, замещенный -F.
8. Соединение по любому из пп. 1-7 или его фармацевтически приемлемая соль,
где R 4 представляет собой:
где X+ и X2+ представляют собой положительные противоионы.
9. Соединение по п. 1, которое представляет собой:
1) (5-((5-(3-хлор-5-цианофенокси)-4-(дифторметил)-6-оксопиримидин-1(6H)-ил)метил)-3-(дифторметил)-6-оксопиридазин-1(6H)-ил)метилдигидрофосфат;
2) (3-хлор-5-((5-(3-хлор-5-цианофенокси)-4-(дифторметил)-6-оксопиримидин-1(6H)-ил)метил)-6-оксопиридазин-1(6H)-ил)метилдигидрофосфат;
3) 3-хлор-5-((5-(3-хлор-5-цианофенокси)-6-оксо-4-(трифторметил)пиримидин-1(6H)-ил)метил)-6-оксопиридазин-1(6H)-ил)метилдигидрофосфат;
4) (5-((5-(3-хлор-5-цианофенокси)-6-оксо-4-(трифторметил)пиримидин-1(6H)-ил)метил)-3-(дифторметил)-6-оксопиридазин-1(6H)-ил)метилдигидрофосфат;
5) (5-((5-(3-хлор-5-цианофенокси)-6-оксо-4-(трифторметил)пиримидин-1(6H)-ил)метил)-3-(1,1-дифторэтил)-6-оксопиридазин-1(6H)-ил)метилдигидрофосфат;
6) (3-((5-(3-хлор-5-цианофенокси)-6-оксо-4-(трифторметил)пиримидин-1(6H)-ил)метил)-6-оксо-5-(трифторметил)пиридазин-1(6H)-ил)метилфосфат;
7) (3-((5-(3-хлор-5-цианофенокси)-6-оксо-4-(трифторметил)пиримидин-1(6H)-ил)метил)-5-(4-фторфенил)-6-оксопиридазин-1(6H)-ил)метилдигидрофосфат; или
8) (5-((5-(3-хлор-5-цианофенокси)-4-(1,1-дифторэтил)-6-оксопиримидин-1(6H)-ил)метил)-3-(1,1-дифторэтил)-6-оксопиридазин-1(6H)-ил)метилдигидрофосфат;
или его фармацевтически приемлемая соль.
10. Фармацевтическая композиция, содержащая эффективное количество соединения по любому из пп. 1-9 или его фармацевтически приемлемой соли и фармацевтически приемлемый носитель.
11. Фармацевтическая композиция, содержащая эффективное количество соединения по любому из пп. 1-9 или его фармацевтически приемлемой соли и фармацевтически приемлемый носитель и дополнительно содержащая эффективное количество средства против ВИЧ, выбранного из противовирусного средства против ВИЧ, иммуномодулятора или противоинфекционного средства.
12. Фармацевтическая композиция по п. 11, где противовирусное средство против ВИЧ представляет собой ингибитор протеазы ВИЧ, ингибитор обратной транскриптазы ВИЧ, ингибитор интегразы ВИЧ, ингибитор слияния ВИЧ, ингибитор вхождения ВИЧ или ингибитор созревания ВИЧ.
13. Способ ингибирования репликации ВИЧ у нуждающегося в этом индивидуума, который включает введение индивидууму эффективного количества соединения по любому из пп. 1-9 или его фармацевтически приемлемой соли.
14. Способ лечения или профилактики инфекции ВИЧ или лечения, профилактики или задержки начала СПИДа у нуждающегося в этом индивидуума, который включает введение индивидууму эффективного количества соединения по любому из пп. 1-9 или его фармацевтически приемлемой соли.
15. Применение соединения по любому из пп. 1-9 или его фармацевтически приемлемой соли в производстве лекарственного средства, пригодного для ингибирования репликации ВИЧ, для лечения или профилактики инфекции ВИЧ или для лечения, профилактики или задержки начала СПИДа.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461973689P | 2014-04-01 | 2014-04-01 | |
| US61/973,689 | 2014-04-01 | ||
| PCT/US2015/022868 WO2015153304A1 (en) | 2014-04-01 | 2015-03-27 | Prodrugs of hiv reverse transcriptase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2016142611A true RU2016142611A (ru) | 2018-05-03 |
| RU2016142611A3 RU2016142611A3 (ru) | 2018-12-26 |
| RU2693622C2 RU2693622C2 (ru) | 2019-07-03 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2016142611A RU2693622C2 (ru) | 2014-04-01 | 2015-03-27 | Пролекарственные средства ингибиторов обратной транскриптазы вич |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US10004740B2 (ru) |
| EP (2) | EP3785714A1 (ru) |
| JP (1) | JP6342011B2 (ru) |
| KR (1) | KR102440843B1 (ru) |
| CN (1) | CN106456639B (ru) |
| AU (1) | AU2015241247B2 (ru) |
| BR (1) | BR112016022722B8 (ru) |
| CA (1) | CA2944187C (ru) |
| CY (1) | CY1123582T1 (ru) |
| DK (1) | DK3125894T3 (ru) |
| ES (1) | ES2828951T3 (ru) |
| HR (1) | HRP20201780T1 (ru) |
| HU (1) | HUE051848T2 (ru) |
| LT (1) | LT3125894T (ru) |
| MX (1) | MX2016012915A (ru) |
| PL (1) | PL3125894T3 (ru) |
| PT (1) | PT3125894T (ru) |
| RS (1) | RS61016B1 (ru) |
| RU (1) | RU2693622C2 (ru) |
| SI (1) | SI3125894T1 (ru) |
| WO (1) | WO2015153304A1 (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JO3470B1 (ar) | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| BR112016022722B8 (pt) | 2014-04-01 | 2023-11-21 | Merck Sharp & Dohme | Composto, composição farmacêutica que o comprende e uso do mesmo |
| CN106008362B (zh) * | 2016-05-24 | 2018-08-10 | 杰达维（上海）医药科技发展有限公司 | 一种嘧啶衍生物的制备方法 |
| BR112020012168B1 (pt) | 2017-12-22 | 2024-01-23 | Sumitomo Chemical Company, Limited | Composto heterocíclico e composição para controlar um artrópode nocivo |
| AU2019402998B2 (en) * | 2018-12-18 | 2022-12-15 | Merck Sharp & Dohme Llc | Pyrimidone derivatives as selective cytotoxic agents against HIV infected cells |
| US20220135537A1 (en) | 2019-02-20 | 2022-05-05 | Sumitomo Chemical Company, Limited | Ether compound and harmful arthropod-controlling composition containing same |
| US20220242847A1 (en) | 2019-05-22 | 2022-08-04 | Merck Sharp & Dohme Corp. | Pyridinone derivatives as selective cytotoxic agents against hiv infected cells |
| TW202304919A (zh) | 2021-03-31 | 2023-02-01 | 印度商皮埃企業有限公司 | 稠合雜環化合物及其作為害蟲控制劑之用途 |
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| SE9904045D0 (sv) | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| US20070021449A1 (en) | 2003-02-07 | 2007-01-25 | Jan Heeres | Pyrimidine derivatives for the prevention of hiv infection |
| TW200423930A (en) | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| EP1608629A1 (en) | 2003-03-24 | 2005-12-28 | F. Hoffmann-La Roche Ag | Benzyl-pyridazinons as reverse transcriptase inhibitors |
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| AR057455A1 (es) | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
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| EP2074117A2 (en) | 2006-11-24 | 2009-07-01 | Takeda Pharmaceutical Company Limited | Heteromonocyclic compound and use thereof |
| TW200831085A (en) | 2006-12-13 | 2008-08-01 | Merck & Co Inc | Non-nucleoside reverse transcriptase inhibitors |
| US8404253B2 (en) | 2006-12-28 | 2013-03-26 | Newport Laboratories, Inc. | Modified live (JMSO strain) Haemophilus parasuis vaccine |
| DE102007032507A1 (de) * | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| EP2222661B1 (en) | 2007-11-20 | 2016-04-20 | Merck Sharp & Dohme Corp. | Non-nucleoside reverse transcriptase inhibitors |
| CA2710987A1 (en) * | 2008-01-08 | 2009-07-16 | Merck Sharp & Dohme Corp. | Process for preparing n-substituted hydroxypyrimidinone carboxamides |
| PL2924034T3 (pl) * | 2010-03-30 | 2017-07-31 | Merck Canada Inc. | Kompozycja farmaceutyczna zawierająca nienukleozydowy inhibitor odwrotnej transkryptazy |
| US20130040914A1 (en) * | 2010-04-08 | 2013-02-14 | Samson M. Jolly | Prodrugs of an hiv reverse transcriptase inhibitor |
| JO3470B1 (ar) | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| BR112016022722B8 (pt) | 2014-04-01 | 2023-11-21 | Merck Sharp & Dohme | Composto, composição farmacêutica que o comprende e uso do mesmo |
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2015
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- 2015-03-27 PL PL15774282T patent/PL3125894T3/pl unknown
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- 2015-03-27 WO PCT/US2015/022868 patent/WO2015153304A1/en active Application Filing
- 2015-03-27 CN CN201580029171.XA patent/CN106456639B/zh active Active
- 2015-03-27 EP EP20194453.5A patent/EP3785714A1/en active Pending
- 2015-03-27 PT PT157742826T patent/PT3125894T/pt unknown
- 2015-03-27 MX MX2016012915A patent/MX2016012915A/es active IP Right Grant
- 2015-03-27 SI SI201531408T patent/SI3125894T1/sl unknown
- 2015-03-27 CA CA2944187A patent/CA2944187C/en active Active
- 2015-03-27 RS RS20201323A patent/RS61016B1/sr unknown
- 2015-03-27 RU RU2016142611A patent/RU2693622C2/ru active
- 2015-03-27 KR KR1020167030064A patent/KR102440843B1/ko active IP Right Grant
- 2015-03-27 EP EP15774282.6A patent/EP3125894B1/en active Active
- 2015-03-27 LT LTEP15774282.6T patent/LT3125894T/lt unknown
- 2015-03-27 HU HUE15774282A patent/HUE051848T2/hu unknown
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2020
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- 2020-11-11 CY CY20201101068T patent/CY1123582T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3785714A1 (en) | 2021-03-03 |
| BR112016022722A2 (pt) | 2017-10-31 |
| RU2693622C2 (ru) | 2019-07-03 |
| HRP20201780T1 (hr) | 2021-06-25 |
| EP3125894A4 (en) | 2017-12-13 |
| CA2944187A1 (en) | 2015-10-08 |
| MX2016012915A (es) | 2016-12-07 |
| DK3125894T3 (da) | 2020-11-16 |
| JP2017512802A (ja) | 2017-05-25 |
| US10004740B2 (en) | 2018-06-26 |
| KR102440843B1 (ko) | 2022-09-29 |
| AU2015241247A1 (en) | 2016-10-06 |
| CY1123582T1 (el) | 2022-03-24 |
| EP3125894B1 (en) | 2020-09-09 |
| WO2015153304A1 (en) | 2015-10-08 |
| KR20160133000A (ko) | 2016-11-21 |
| RU2016142611A3 (ru) | 2018-12-26 |
| US20170173015A1 (en) | 2017-06-22 |
| CA2944187C (en) | 2018-06-19 |
| HUE051848T2 (hu) | 2021-03-29 |
| PT3125894T (pt) | 2020-11-05 |
| EP3125894A1 (en) | 2017-02-08 |
| CN106456639B (zh) | 2019-05-10 |
| ES2828951T3 (es) | 2021-05-28 |
| JP6342011B2 (ja) | 2018-06-13 |
| PL3125894T3 (pl) | 2021-02-08 |
| RS61016B1 (sr) | 2020-12-31 |
| AU2015241247B2 (en) | 2017-09-14 |
| BR112016022722B8 (pt) | 2023-11-21 |
| CN106456639A (zh) | 2017-02-22 |
| LT3125894T (lt) | 2020-12-10 |
| BR112016022722B1 (pt) | 2023-03-07 |
| SI3125894T1 (sl) | 2020-12-31 |
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