KR20170070197A - 나르제니신 화합물 및 항박테리아제로서의 그의 용도 - Google Patents
나르제니신 화합물 및 항박테리아제로서의 그의 용도 Download PDFInfo
- Publication number
- KR20170070197A KR20170070197A KR1020177013260A KR20177013260A KR20170070197A KR 20170070197 A KR20170070197 A KR 20170070197A KR 1020177013260 A KR1020177013260 A KR 1020177013260A KR 20177013260 A KR20177013260 A KR 20177013260A KR 20170070197 A KR20170070197 A KR 20170070197A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- ring
- optionally substituted
- arya
- heta
- 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.)
- Withdrawn
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- 239000003242 anti bacterial agent Substances 0.000 title description 11
- RBUYHCJZOXFDKG-KFIBIINQSA-N nargenicin Chemical class O([C@@H]1[C@H](C)[C@@H](O)[C@H]2[C@]3\4O[C@H]1[C@@H]2C=C[C@@H]3C[C@@H](C(O[C@@H]([C@H](C)/C=C/4C)[C@@H](C)O)=O)OC)C(=O)C1=CC=C[N]1 RBUYHCJZOXFDKG-KFIBIINQSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
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- 238000000034 method Methods 0.000 claims abstract description 63
- 108010013829 alpha subunit DNA polymerase III Proteins 0.000 claims abstract description 22
- 208000015181 infectious disease Diseases 0.000 claims abstract description 22
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 161
- 125000001424 substituent group Chemical group 0.000 claims description 81
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 80
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- 125000006413 ring segment Chemical group 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 201000008827 tuberculosis Diseases 0.000 claims description 39
- 125000002950 monocyclic group Chemical group 0.000 claims description 38
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- 150000002367 halogens Chemical class 0.000 claims description 37
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 34
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- 125000002619 bicyclic group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical group 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
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- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 125000001544 thienyl group Chemical group 0.000 claims description 4
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000000107 disulfanyl group Chemical group [*]SS[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 241000589291 Acinetobacter Species 0.000 claims 1
- 241000588923 Citrobacter Species 0.000 claims 1
- 241000588914 Enterobacter Species 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 claims 1
- 241000588771 Morganella <proteobacterium> Species 0.000 claims 1
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- 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 abstract description 5
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- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 abstract description 2
- 235000007625 naringenin Nutrition 0.000 abstract description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 239000011541 reaction mixture Substances 0.000 description 82
- 239000000243 solution Substances 0.000 description 77
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- 239000000203 mixture Substances 0.000 description 71
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- 230000002829 reductive effect Effects 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 27
- WRHZVMBBRYBTKZ-UHFFFAOYSA-M pyrrole-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-M 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- 238000000746 purification Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 20
- 239000003643 water by type Substances 0.000 description 19
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 18
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 17
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- 238000004440 column chromatography Methods 0.000 description 14
- 208000027531 mycobacterial infectious disease Diseases 0.000 description 14
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- 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
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- 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
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/16—Halogenated acetic acids
- C07C53/18—Halogenated acetic acids containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged 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
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2014/089204 | 2014-10-22 | ||
| PCT/CN2014/089204 WO2016061772A1 (en) | 2014-10-22 | 2014-10-22 | Nargenicin compounds and uses thereof as antibacterial agents |
| PCT/US2015/056627 WO2016064982A1 (en) | 2014-10-22 | 2015-10-21 | Nargenicin compounds and uses thereof as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20170070197A true KR20170070197A (ko) | 2017-06-21 |
Family
ID=55760063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177013260A Withdrawn KR20170070197A (ko) | 2014-10-22 | 2015-10-21 | 나르제니신 화합물 및 항박테리아제로서의 그의 용도 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US9944654B2 (https=) |
| EP (1) | EP3209667B1 (https=) |
| JP (1) | JP2017533200A (https=) |
| KR (1) | KR20170070197A (https=) |
| CN (1) | CN107108646A (https=) |
| AU (1) | AU2015335992A1 (https=) |
| BR (1) | BR112017008101A2 (https=) |
| CA (1) | CA2964377A1 (https=) |
| MX (1) | MX2017005271A (https=) |
| RU (1) | RU2017117253A (https=) |
| WO (2) | WO2016061772A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220014165A (ko) | 2020-07-28 | 2022-02-04 | 선문대학교 산학협력단 | 나르제니신 a1 유도체를 포함하는 항혈관신생용 조성물 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016061772A1 (en) | 2014-10-22 | 2016-04-28 | Merck Sharp & Dohme Corp. | Nargenicin compounds and uses thereof as antibacterial agents |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4148883A (en) | 1977-08-18 | 1979-04-10 | Pfizer Inc. | Antibiotics produced by new species of nocardia |
| US4360683A (en) * | 1980-08-06 | 1982-11-23 | The Upjohn Company | Antibiotic nodusmicin derivatives |
| US4351769A (en) * | 1980-08-25 | 1982-09-28 | The Upjohn Company | Antibiotic composition of matter |
| US4448970A (en) * | 1981-02-19 | 1984-05-15 | The Upjohn Company | Nargenicin derivatives |
| US4436747A (en) | 1982-10-21 | 1984-03-13 | Pfizer Inc. | Nargenicin C1 |
| US4605624A (en) * | 1982-10-21 | 1986-08-12 | Pfizer Inc. | Nocardia species capable of producing nargenicin C1 |
| ES2258234T3 (es) | 2002-08-12 | 2006-08-16 | PHARMACIA & UPJOHN COMPANY LLC | N-aril-2-oxazolidinonas y sus derivados. |
| GB0227701D0 (en) | 2002-11-28 | 2003-01-08 | Astrazeneca Ab | Chemical compounds |
| MXPA05005522A (es) | 2002-11-28 | 2005-07-25 | Astrazeneca Ab | Oxazolidinonas como agentes antibacterianos. |
| WO2005012270A2 (en) | 2003-07-29 | 2005-02-10 | Rib-X Pharmaceuticals, Inc. | Biaryl heterocyclic amines, amides, and sulfur-containing compounds and methods of making and using the same |
| KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| JP2008500318A (ja) | 2004-05-25 | 2008-01-10 | アストラゼネカ アクチボラグ | 抗菌剤としての３−｛４−（ピリジン−３−イル）フェニル｝−５−（１ｈ−１，２，３−トリアゾール−１−イルメチル）−１，３−オキサゾリジン−２−オン |
| WO2007133803A2 (en) | 2006-05-15 | 2007-11-22 | Rib-X Pharmaceuticals, Inc. | Treatment of mycobacterial infections |
| WO2008069619A1 (en) | 2006-12-08 | 2008-06-12 | Legochem Bioscience Ltd. | Novel oxazolidinone derivatives, process for preparing thereof and pharmaceutical composition containing the same |
| KR101040468B1 (ko) | 2008-02-29 | 2011-06-09 | 조선대학교산학협력단 | 새로운 노카르디아 속 균주 및 그의 발효 배양물의 용도 |
| KR101022564B1 (ko) | 2008-12-19 | 2011-03-16 | 조선대학교산학협력단 | 나르제니신을 포함하는 염증성 신경퇴행성 질환의 치료용 제약 조성물 |
| WO2011139832A2 (en) | 2010-04-28 | 2011-11-10 | Rib-X Pharmaceuticals, Inc. | Method for treating mycobacterial infections |
| KR101561964B1 (ko) | 2013-11-15 | 2015-10-20 | 한국과학기술연구원 | 옥사졸리디논 화합물 및 이를 포함하는 c형 간염 예방 또는 치료용 약학 조성물 |
| WO2016061772A1 (en) | 2014-10-22 | 2016-04-28 | Merck Sharp & Dohme Corp. | Nargenicin compounds and uses thereof as antibacterial agents |
-
2014
- 2014-10-22 WO PCT/CN2014/089204 patent/WO2016061772A1/en not_active Ceased
-
2015
- 2015-10-21 CA CA2964377A patent/CA2964377A1/en not_active Abandoned
- 2015-10-21 BR BR112017008101A patent/BR112017008101A2/pt not_active Application Discontinuation
- 2015-10-21 KR KR1020177013260A patent/KR20170070197A/ko not_active Withdrawn
- 2015-10-21 AU AU2015335992A patent/AU2015335992A1/en not_active Abandoned
- 2015-10-21 JP JP2017521550A patent/JP2017533200A/ja active Pending
- 2015-10-21 US US15/517,570 patent/US9944654B2/en active Active
- 2015-10-21 WO PCT/US2015/056627 patent/WO2016064982A1/en not_active Ceased
- 2015-10-21 CN CN201580069971.4A patent/CN107108646A/zh active Pending
- 2015-10-21 MX MX2017005271A patent/MX2017005271A/es unknown
- 2015-10-21 EP EP15853228.3A patent/EP3209667B1/en active Active
- 2015-10-21 RU RU2017117253A patent/RU2017117253A/ru not_active Application Discontinuation
-
2018
- 2018-03-02 US US15/910,571 patent/US10144741B2/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220014165A (ko) | 2020-07-28 | 2022-02-04 | 선문대학교 산학협력단 | 나르제니신 a1 유도체를 포함하는 항혈관신생용 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107108646A (zh) | 2017-08-29 |
| EP3209667A1 (en) | 2017-08-30 |
| CA2964377A1 (en) | 2016-04-28 |
| RU2017117253A (ru) | 2018-11-23 |
| EP3209667A4 (en) | 2018-06-06 |
| JP2017533200A (ja) | 2017-11-09 |
| RU2017117253A3 (https=) | 2019-04-16 |
| AU2015335992A1 (en) | 2017-04-20 |
| US10144741B2 (en) | 2018-12-04 |
| WO2016064982A1 (en) | 2016-04-28 |
| EP3209667B1 (en) | 2025-03-19 |
| US9944654B2 (en) | 2018-04-17 |
| WO2016061772A1 (en) | 2016-04-28 |
| MX2017005271A (es) | 2017-08-15 |
| US20180186808A1 (en) | 2018-07-05 |
| BR112017008101A2 (pt) | 2018-02-20 |
| US20170305924A1 (en) | 2017-10-26 |
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Patent event date: 20170517 Patent event code: PA01051R01D Comment text: International Patent Application |
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