JP6407288B2 - 抗菌性１ｈ−インダゾール及び１ｈ−インドール誘導体 - Google Patents
抗菌性１ｈ−インダゾール及び１ｈ−インドール誘導体 Download PDFInfo
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- JP6407288B2 JP6407288B2 JP2016541300A JP2016541300A JP6407288B2 JP 6407288 B2 JP6407288 B2 JP 6407288B2 JP 2016541300 A JP2016541300 A JP 2016541300A JP 2016541300 A JP2016541300 A JP 2016541300A JP 6407288 B2 JP6407288 B2 JP 6407288B2
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- JP
- Japan
- Prior art keywords
- hydroxy
- methyl
- methylsulfonyl
- butanamide
- indazol
- 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.)
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- 230000000844 anti-bacterial effect Effects 0.000 title description 13
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- -1 1-amino-cyclopropyl Chemical group 0.000 claims description 466
- 150000001875 compounds Chemical class 0.000 claims description 458
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 65
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 42
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- 208000022362 bacterial infectious disease Diseases 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 230000002265 prevention Effects 0.000 claims description 18
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
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- 239000007787 solid Substances 0.000 description 75
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- 239000000047 product Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
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- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000735 select agent Toxicity 0.000 description 1
- 229940007046 shigella dysenteriae Drugs 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229960001608 teicoplanin Drugs 0.000 description 1
- 229960005240 telavancin Drugs 0.000 description 1
- ONUMZHGUFYIKPM-MXNFEBESSA-N telavancin Chemical compound O1[C@@H](C)[C@@H](O)[C@](NCCNCCCCCCCCCC)(C)C[C@@H]1O[C@H]1[C@H](OC=2C3=CC=4[C@H](C(N[C@H]5C(=O)N[C@H](C(N[C@@H](C6=CC(O)=C(CNCP(O)(O)=O)C(O)=C6C=6C(O)=CC=C5C=6)C(O)=O)=O)[C@H](O)C5=CC=C(C(=C5)Cl)O3)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](NC(=O)[C@@H](CC(C)C)NC)[C@H](O)C3=CC=C(C(=C3)Cl)OC=2C=4)O[C@H](CO)[C@@H](O)[C@@H]1O ONUMZHGUFYIKPM-MXNFEBESSA-N 0.000 description 1
- 108010089019 telavancin Proteins 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- FBQUIIPSWDMUBM-UHFFFAOYSA-N tert-butyl n-[(1-formylcyclopropyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1(C=O)CC1 FBQUIIPSWDMUBM-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 229940072172 tetracycline antibiotic Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- DQOHDRDDPZNSQI-UHFFFAOYSA-N thietan-3-one Chemical compound O=C1CSC1 DQOHDRDDPZNSQI-UHFFFAOYSA-N 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
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- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- YEMJHNYABQHWHL-UHFFFAOYSA-N tributyl(ethynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C#C YEMJHNYABQHWHL-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
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- 229940098232 yersinia enterocolitica Drugs 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/41—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
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13198338 | 2013-12-19 | ||
| EP13198338.9 | 2013-12-19 | ||
| PCT/EP2014/078384 WO2015091741A1 (en) | 2013-12-19 | 2014-12-18 | Antibacterial 1h-indazole and 1h-indole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017500336A JP2017500336A (ja) | 2017-01-05 |
| JP6407288B2 true JP6407288B2 (ja) | 2018-10-17 |
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| EP (1) | EP3083567B1 (enExample) |
| JP (1) | JP6407288B2 (enExample) |
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| AR (1) | AR100032A1 (enExample) |
| AU (1) | AU2014368619B2 (enExample) |
| BR (1) | BR112016014115A8 (enExample) |
| CA (1) | CA2933604A1 (enExample) |
| CL (1) | CL2016001524A1 (enExample) |
| EA (1) | EA030730B1 (enExample) |
| ES (1) | ES2666130T3 (enExample) |
| IL (1) | IL246201A0 (enExample) |
| MA (1) | MA39189A1 (enExample) |
| MX (1) | MX360983B (enExample) |
| PH (1) | PH12016501102A1 (enExample) |
| PL (1) | PL3083567T3 (enExample) |
| SG (1) | SG11201605014YA (enExample) |
| TR (1) | TR201807881T4 (enExample) |
| TW (1) | TW201609641A (enExample) |
| WO (1) | WO2015091741A1 (enExample) |
| ZA (1) | ZA201604968B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| AR099612A1 (es) | 2014-03-04 | 2016-08-03 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona |
| WO2015173329A1 (en) | 2014-05-16 | 2015-11-19 | Actelion Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
| BR112017010474A2 (pt) | 2014-11-19 | 2017-12-26 | Actelion Pharmaceuticals Ltd | derivados antibacterianos de benzotiazol |
| AR105646A1 (es) | 2015-08-11 | 2017-10-25 | Actelion Pharmaceuticals Ltd | Agentes antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituida |
| AR105839A1 (es) * | 2015-08-28 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos pirrolidin-2-ona anulares |
| AR105848A1 (es) * | 2015-08-31 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados heterocíclicos antibacterianos |
| AR105889A1 (es) | 2015-09-03 | 2017-11-22 | Actelion Pharmaceuticals Ltd | Compuestos antibacterianos 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituidos |
| AU2017267194A1 (en) * | 2016-05-17 | 2019-01-17 | Idorsia Pharmaceuticals Ltd | 6-(BUTA-1,3-DIYN-1-YL)benzo[D]thiazole derivatives |
| WO2018216822A1 (en) | 2017-05-25 | 2018-11-29 | Taisho Pharmaceutical Co., Ltd. | Novel imidazole derivatives |
| WO2019086452A1 (en) * | 2017-10-31 | 2019-05-09 | Idorsia Pharmaceuticals Ltd | Antibacterial heteroaromatic compounds |
| CN113666860B (zh) * | 2020-05-14 | 2024-03-15 | 鲁南制药集团股份有限公司 | 一种7-乙基色醇的制备方法 |
| CN119014415B (zh) * | 2024-08-19 | 2025-09-05 | 浙江大学 | 1-甲氧基吲哚在驱避和/或杀灭害虫中的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SG2013013339A (en) | 2002-03-13 | 2014-12-30 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| DE102004017930A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| JP4931823B2 (ja) | 2004-10-18 | 2012-05-16 | アムジエン・インコーポレーテツド | チアジアゾール化合物及び使用方法 |
| PT1863818E (pt) | 2005-03-23 | 2010-04-09 | Hoffmann La Roche | Derivados de acetilenil-pirazolo-pirimidina como antagonistas de mglur2 |
| CA2691987C (en) | 2007-06-12 | 2016-08-16 | Achaogen, Inc. | Antibacterial agents |
| WO2010135536A2 (en) | 2009-05-20 | 2010-11-25 | Ardea Biosciences, Inc. | Methods of modulating uric acid levels |
| CA2774250C (en) * | 2009-10-13 | 2013-12-17 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| JP5793766B2 (ja) | 2009-12-16 | 2015-10-14 | ファイザー・インク | 抗菌剤として有用なｎ−結合型ヒドロキサム酸誘導体 |
| GB2483736B (en) | 2010-09-16 | 2012-08-29 | Aragon Pharmaceuticals Inc | Estrogen receptor modulators and uses thereof |
| EP2638006A1 (en) | 2010-11-10 | 2013-09-18 | Achaogen, Inc. | Hydroxamic acid derivatives and their use in the treatment of bacterial infections |
| KR20120079015A (ko) | 2011-01-03 | 2012-07-11 | 한미약품 주식회사 | Ｇ 단백질-커플링된 수용체의 조절을 위한 신규한 비사이클릭 화합물 |
| AP3336A (en) * | 2011-03-07 | 2015-07-31 | Pfizer | Fluoro-pyridinone derivatives useful as antibacterial agents |
| WO2012137094A1 (en) | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Isoxazole derivatives useful as antibacterial agents |
| WO2012137099A1 (en) * | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents |
| EP2847162A1 (en) | 2012-05-09 | 2015-03-18 | Achaogen, Inc. | Antibacterial agents |
| WO2013170165A1 (en) | 2012-05-10 | 2013-11-14 | Achaogen, Inc. | Antibacterial agents |
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| AR099612A1 (es) | 2014-03-04 | 2016-08-03 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona |
| WO2015173329A1 (en) | 2014-05-16 | 2015-11-19 | Actelion Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
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2014
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- 2014-12-18 EP EP14812752.5A patent/EP3083567B1/en not_active Not-in-force
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Also Published As
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|---|---|
| TW201609641A (zh) | 2016-03-16 |
| IL246201A0 (en) | 2016-08-02 |
| US20170029411A1 (en) | 2017-02-02 |
| MX2016007991A (es) | 2016-10-07 |
| JP2017500336A (ja) | 2017-01-05 |
| EA030730B1 (ru) | 2018-09-28 |
| EP3083567B1 (en) | 2018-03-07 |
| CA2933604A1 (en) | 2015-06-25 |
| AU2014368619A1 (en) | 2016-07-28 |
| SG11201605014YA (en) | 2016-07-28 |
| ZA201604968B (en) | 2018-11-28 |
| CL2016001524A1 (es) | 2017-01-27 |
| EA201600475A1 (ru) | 2016-11-30 |
| MA39189A1 (fr) | 2017-06-30 |
| CN105829288B (zh) | 2019-01-15 |
| AR100032A1 (es) | 2016-09-07 |
| CN105829288A (zh) | 2016-08-03 |
| WO2015091741A1 (en) | 2015-06-25 |
| TR201807881T4 (tr) | 2018-06-21 |
| PH12016501102A1 (en) | 2016-07-11 |
| PL3083567T3 (pl) | 2018-08-31 |
| AU2014368619B2 (en) | 2018-11-22 |
| MX360983B (es) | 2018-11-22 |
| US9624206B2 (en) | 2017-04-18 |
| BR112016014115A2 (enExample) | 2017-08-08 |
| ES2666130T3 (es) | 2018-05-03 |
| BR112016014115A8 (pt) | 2017-12-26 |
| KR20160098503A (ko) | 2016-08-18 |
| EP3083567A1 (en) | 2016-10-26 |
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