CN109575018A - 一种抗感染化合物 - Google Patents
一种抗感染化合物 Download PDFInfo
- Publication number
- CN109575018A CN109575018A CN201811384685.9A CN201811384685A CN109575018A CN 109575018 A CN109575018 A CN 109575018A CN 201811384685 A CN201811384685 A CN 201811384685A CN 109575018 A CN109575018 A CN 109575018A
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- CN
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- Prior art keywords
- chlorine
- ethyl
- hydrogen
- methyl
- nitrogen
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- 238000011282 treatment Methods 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 151
- 239000000460 chlorine Substances 0.000 claims description 146
- 229910052801 chlorine Inorganic materials 0.000 claims description 146
- 239000001257 hydrogen Substances 0.000 claims description 116
- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 105
- 150000002431 hydrogen Chemical class 0.000 claims description 100
- 229910052757 nitrogen Inorganic materials 0.000 claims description 88
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 47
- 239000001301 oxygen Substances 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
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- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
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- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229960005206 pyrazinamide Drugs 0.000 description 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 229940100618 rectal suppository Drugs 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229950004288 tosilate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 229940120293 vaginal suppository Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| US201361861750P | 2013-08-02 | 2013-08-02 | |
| US61/861,750 | 2013-08-02 | ||
| CN201480054331.1A CN105745208A (zh) | 2013-08-02 | 2014-08-01 | 一种抗感染化合物 |
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| CN201480054331.1A Division CN105745208A (zh) | 2013-08-02 | 2014-08-01 | 一种抗感染化合物 |
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|---|---|
| CN109575018A true CN109575018A (zh) | 2019-04-05 |
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| CN201811384685.9A Pending CN109575018A (zh) | 2013-08-02 | 2014-08-01 | 一种抗感染化合物 |
| CN201480054331.1A Pending CN105745208A (zh) | 2013-08-02 | 2014-08-01 | 一种抗感染化合物 |
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| CN201480054331.1A Pending CN105745208A (zh) | 2013-08-02 | 2014-08-01 | 一种抗感染化合物 |
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| US (1) | US20160185774A1 (enExample) |
| EP (1) | EP3027615B1 (enExample) |
| JP (3) | JP2016525562A (enExample) |
| KR (1) | KR102292293B1 (enExample) |
| CN (2) | CN109575018A (enExample) |
| DK (1) | DK3027615T3 (enExample) |
| ES (1) | ES2883565T3 (enExample) |
| HU (1) | HUE056198T2 (enExample) |
| PH (1) | PH12016500207A1 (enExample) |
| RU (1) | RU2734760C2 (enExample) |
| SG (1) | SG11201600686QA (enExample) |
| WO (1) | WO2015014993A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017001660A1 (en) | 2015-07-02 | 2017-01-05 | Janssen Sciences Ireland Uc | Antibacterial compounds |
| AU2016324598A1 (en) | 2015-09-17 | 2018-03-15 | Marvin J. Miller | Benzyl amine-containing heterocyclic compounds and compositions useful against mycobacterial infection |
| JP2019518046A (ja) * | 2016-06-16 | 2019-06-27 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | 抗菌薬としての複素環式化合物 |
| JP2019518050A (ja) * | 2016-06-16 | 2019-06-27 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | 抗菌薬としての複素環式化合物 |
| WO2018158280A1 (en) | 2017-03-01 | 2018-09-07 | Janssen Sciences Ireland Uc | Combination therapy |
| US11129816B2 (en) | 2017-10-05 | 2021-09-28 | Quretech Bio Ab | Ring-fused thiazolino 2-pyridones in combination with a drug against tuberculosis |
| CN108101828B (zh) * | 2018-01-15 | 2021-05-04 | 西华师范大学 | 3-吲哚基甲酰胺类化合物及其制备方法 |
| CN108159049B (zh) * | 2018-02-01 | 2021-01-05 | 中国科学院广州生物医药与健康研究院 | 一种吡啶类化合物的新用途 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| JPWO2020203609A1 (enExample) * | 2019-03-29 | 2020-10-08 | ||
| JP2022081710A (ja) * | 2019-03-29 | 2022-06-01 | ユーティアイ リミテッド パートナーシップ | 関節リウマチを治療するためのｔ型カルシウムチャネル阻害剤の使用 |
| TWI861208B (zh) * | 2019-09-10 | 2024-11-11 | 日商鹽野義製藥股份有限公司 | 對分枝桿菌感染有用之含苄胺的 5,6-雜芳族化合物 |
| WO2021048342A1 (en) | 2019-09-13 | 2021-03-18 | Janssen Sciences Ireland Unlimited Company | Antibacterial compounds |
| MX2022003814A (es) * | 2019-09-30 | 2022-05-06 | Janssen Sciences Ireland Unlimited Co | Compuestos antibacterianos de 4-quinolinona. |
| CA3151712A1 (en) * | 2019-09-30 | 2021-04-08 | Jerome Emile Georges Guillemont | Cytochrome bd inhibitors as anti-bacterial agents for the treatment of tuberculosis |
| KR102381397B1 (ko) * | 2020-07-10 | 2022-03-30 | 경희대학교 산학협력단 | 신규 나프토퀴논 유도체 화합물 및 이를 포함하는 항균용 조성물 |
| KR20230157400A (ko) | 2021-03-16 | 2023-11-16 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 항박테리아성 화합물 |
| CA3211592A1 (en) | 2021-03-17 | 2022-09-22 | Jerome Emile Georges Guillemont | Antibacterial compounds |
| CN117440958A (zh) * | 2021-03-17 | 2024-01-23 | 爱尔兰詹森科学公司 | 抗菌化合物 |
| CN118159543A (zh) | 2021-10-28 | 2024-06-07 | 爱尔兰詹森科学公司 | 在治疗细菌感染中使用的咪唑并吡啶酰胺和相关化合物 |
| WO2024089170A1 (en) | 2022-10-27 | 2024-05-02 | Janssen Sciences Ireland Unlimited Company | Antibacterial compounds |
| WO2024223859A1 (en) | 2023-04-26 | 2024-10-31 | Janssen Pharmaceutica Nv | Antibacterial compounds |
| WO2025017047A1 (en) | 2023-07-18 | 2025-01-23 | Janssen Pharmaceutica Nv | Combination products of at least three antibiotics comprising bedaquiline, pretomanid or delamanid, and a cytochrome bc1 inhibitor, and their use in the treatment of mycobacterial infections |
Citations (1)
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|---|---|---|---|---|
| CN102869661A (zh) * | 2010-03-18 | 2013-01-09 | 韩国巴斯德研究所 | 抗感染化合物 |
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| FR2906250B1 (fr) * | 2006-09-22 | 2008-10-31 | Sanofi Aventis Sa | Derives de 2-aryl-6phenyl-imidazo(1,2-a) pyridines, leur preparation et leur application en therapeutique |
| US20100298314A1 (en) * | 2006-12-20 | 2010-11-25 | Schering Corporation | Novel jnk inhibitors |
| WO2009140101A2 (en) * | 2008-05-12 | 2009-11-19 | Boehringer Ingelheim International Gmbh | Imidazopyridine compounds useful as mmp-13 inhibitors |
| EP2496578A4 (en) * | 2009-11-05 | 2013-08-21 | Univ Notre Dame Du Lac | IMIDAZO [1,2-A] PYRIDINE COMPOUNDS, THEIR SYNTHESIS AND METHODS OF USE THEREOF |
| US9029389B2 (en) * | 2011-04-21 | 2015-05-12 | Institut Pasteur Korea | Anti-inflammation compounds |
| CN103324035B (zh) * | 2013-06-20 | 2015-07-01 | 深圳市华星光电技术有限公司 | 掩膜板和阵列基板的制作方法 |
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2014
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- 2014-08-01 CN CN201811384685.9A patent/CN109575018A/zh active Pending
- 2014-08-01 KR KR1020167005457A patent/KR102292293B1/ko active Active
- 2014-08-01 EP EP14745158.7A patent/EP3027615B1/en active Active
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- 2014-08-01 US US14/909,663 patent/US20160185774A1/en not_active Abandoned
- 2014-08-01 JP JP2016530547A patent/JP2016525562A/ja not_active Withdrawn
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102869661A (zh) * | 2010-03-18 | 2013-01-09 | 韩国巴斯德研究所 | 抗感染化合物 |
Non-Patent Citations (2)
| Title |
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| KEVIN PETHE ET AL.: "Discovery of Q203,a potent clinical candidate for the treatment of tuberculosis", 《NATURE MEDICINE》 * |
| PRAVIN S. SHIRUDE ET AL.: "Azaindoles: Noncovalent DprE1 Inhibitors from Scaffold Morphing Efforts, Kill Mycobacterium tuberculosis and Are Efficacious in Vivo", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| SG11201600686QA (en) | 2016-02-26 |
| RU2016107378A3 (enExample) | 2018-03-29 |
| JP2018158941A (ja) | 2018-10-11 |
| EP3027615B1 (en) | 2021-07-21 |
| RU2016107378A (ru) | 2017-09-07 |
| JP2019131606A (ja) | 2019-08-08 |
| KR20170082450A (ko) | 2017-07-14 |
| DK3027615T3 (da) | 2021-10-25 |
| WO2015014993A3 (en) | 2015-04-02 |
| PH12016500207A1 (en) | 2016-04-25 |
| JP2016525562A (ja) | 2016-08-25 |
| HUE056198T2 (hu) | 2022-02-28 |
| JP6757768B2 (ja) | 2020-09-23 |
| EP3027615A2 (en) | 2016-06-08 |
| KR102292293B1 (ko) | 2021-08-23 |
| ES2883565T3 (es) | 2021-12-09 |
| WO2015014993A2 (en) | 2015-02-05 |
| CN105745208A (zh) | 2016-07-06 |
| RU2734760C2 (ru) | 2020-10-23 |
| US20160185774A1 (en) | 2016-06-30 |
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