AU2014273751A1 - Conjugate of benzofuranone and indole or azaindole, and preparation and uses thereof - Google Patents
Conjugate of benzofuranone and indole or azaindole, and preparation and uses thereof Download PDFInfo
- Publication number
- AU2014273751A1 AU2014273751A1 AU2014273751A AU2014273751A AU2014273751A1 AU 2014273751 A1 AU2014273751 A1 AU 2014273751A1 AU 2014273751 A AU2014273751 A AU 2014273751A AU 2014273751 A AU2014273751 A AU 2014273751A AU 2014273751 A1 AU2014273751 A1 AU 2014273751A1
- Authority
- AU
- Australia
- Prior art keywords
- acid
- oxo
- ch2ch
- derivatives
- och
- 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.)
- Abandoned
Links
- 238000002360 preparation method Methods 0.000 title claims description 24
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title claims description 18
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
- 201000010099 disease Diseases 0.000 claims abstract description 31
- -1 oxo indirubin Chemical compound 0.000 claims abstract description 30
- 239000003814 drug Substances 0.000 claims abstract description 29
- 229940079593 drug Drugs 0.000 claims abstract description 22
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 12
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 10
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 5
- 230000035755 proliferation Effects 0.000 claims abstract description 5
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 99
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 23
- 108091007914 CDKs Proteins 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003435 aroyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 17
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 17
- PURZPTHFQRDYLF-UHFFFAOYSA-N C1=CC=C2NC=CC2=C1.C1=CC=C2OC(=O)CC2=C1 Chemical compound C1=CC=C2NC=CC2=C1.C1=CC=C2OC(=O)CC2=C1 PURZPTHFQRDYLF-UHFFFAOYSA-N 0.000 claims description 15
- 125000003147 glycosyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 235000011054 acetic acid Nutrition 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 12
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 12
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000003826 tablet Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
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- 238000001727 in vivo Methods 0.000 claims description 5
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- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 239000011669 selenium Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 230000004163 JAK-STAT signaling pathway Effects 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 102000000887 Transcription factor STAT Human genes 0.000 claims description 4
- 108050007918 Transcription factor STAT Proteins 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 4
- 229940093915 gynecological organic acid Drugs 0.000 claims description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
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- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
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- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 2
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 claims description 2
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- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
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- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 claims description 2
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Landscapes
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Applications Claiming Priority (3)
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| CN201310202029.3 | 2013-05-28 | ||
| CN201310202029.3A CN103333161B (zh) | 2013-05-28 | 2013-05-28 | 1’-氧代靛玉红的制备和用途 |
| PCT/CN2014/000525 WO2014190758A1 (zh) | 2013-05-28 | 2014-05-26 | 苯并呋喃酮与吲哚或氮杂吲哚偶合物及其制备与应用 |
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| AU2014273751A1 true AU2014273751A1 (en) | 2015-10-29 |
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| AU2014273751A Abandoned AU2014273751A1 (en) | 2013-05-28 | 2014-05-26 | Conjugate of benzofuranone and indole or azaindole, and preparation and uses thereof |
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| Country | Link |
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| US (1) | US9868734B2 (enExample) |
| EP (1) | EP3006442A4 (enExample) |
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| CN (2) | CN103333161B (enExample) |
| AU (1) | AU2014273751A1 (enExample) |
| CA (1) | CA2912943A1 (enExample) |
| MX (1) | MX2015016217A (enExample) |
| RU (1) | RU2015140611A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103333161B (zh) * | 2013-05-28 | 2015-09-30 | 滁州市洛达生物科技有限公司 | 1’-氧代靛玉红的制备和用途 |
| CN108721279B (zh) * | 2017-04-19 | 2021-06-29 | 安尼根有限公司 | 包含5′-羟基-5-硝基-靛玉红-3′-肟作为活性成分的乳腺癌治疗剂 |
| CN106946760A (zh) * | 2017-04-28 | 2017-07-14 | 遵义医学院 | 靛玉红衍生物或药学上能接受的盐用于抗肿瘤药物及制备方法 |
| CN111233741B (zh) * | 2020-03-04 | 2021-04-16 | 大连理工大学 | 一种有机催化靛红自缩合制备异靛蓝类化合物的方法 |
| WO2021188855A1 (en) * | 2020-03-19 | 2021-09-23 | Board Of Regents Of The University Of Nebraska | Symbiotic prodrugs for the treatment of cancer and other diseases |
| WO2022171265A1 (en) * | 2021-02-09 | 2022-08-18 | Boehringer Ingelheim International Gmbh | Modulators of complex i |
| CN113072540B (zh) * | 2021-03-29 | 2023-07-14 | 贵州医科大学 | 一种靛玉红衍生的降解剂及其制备与应用 |
| WO2023090935A1 (ko) * | 2021-11-18 | 2023-05-25 | 애니젠 주식회사 | 뉴클레오린에 특이적으로 결합하는 agm 펩타이드를 제조하는 방법 |
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| DE10129028A1 (de) * | 2001-06-11 | 2003-01-02 | Schering Ag | Lösliche Cdk-inhibitorische Indirubinderivate |
| US20050154046A1 (en) * | 2004-01-12 | 2005-07-14 | Longgui Wang | Methods of treating an inflammatory-related disease |
| US20100098702A1 (en) * | 2008-09-16 | 2010-04-22 | Longgui Wang | Method of treating androgen independent prostate cancer |
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| KR100588803B1 (ko) * | 2004-01-27 | 2006-06-12 | 학교법인조선대학교 | 암세포주에 항암활성을 지닌 인디루빈 유도체 |
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| CN101314584A (zh) * | 2007-05-28 | 2008-12-03 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | HGF/c-Met信号通道抑制剂及其制备方法和用途 |
| CN101074229B (zh) | 2007-06-08 | 2010-09-01 | 无锡杰西医药科技有限公司 | 7-氮杂靛玉红和7-氮杂异靛蓝衍生物制备及其药学用途 |
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| EP2379549B1 (en) * | 2008-12-22 | 2016-09-21 | Eisenbrand, Gerhard | 7-azaindirubins, 7'-azaindirubins, 7-7'-diazaindirubin and the corresponding 3'-oxime ether derivates: production thereof, their production and use as a medicament |
| CN101492465A (zh) * | 2009-03-05 | 2009-07-29 | 上海交通大学 | 用于抗肿瘤药物的7，7＇-二氮杂靛玉红类化合物 |
| CN101492448B (zh) * | 2009-03-05 | 2012-09-19 | 上海交通大学 | 用于抗肿瘤药物的7＇-氮杂靛玉红类化合物 |
| CN101492410B (zh) * | 2009-03-05 | 2011-06-22 | 上海交通大学 | 用于抗肿瘤药物的靛玉红类化合物 |
| CN101704813B (zh) * | 2009-11-25 | 2011-11-16 | 上海交通大学 | 1′-硫代靛玉红类化合物、用途及其制备方法 |
| CN101747339B (zh) * | 2009-11-25 | 2012-04-25 | 上海交通大学 | 1′-硫代氮杂靛玉红类化合物、用途及其制备方法 |
| KR101180030B1 (ko) * | 2010-02-05 | 2012-09-05 | 광주과학기술원 | 사이클린-의존적 키나제 저해제로서 항암 활성을 지닌 인디루빈-3'-옥심 유도체 |
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| CN103333161B (zh) * | 2013-05-28 | 2015-09-30 | 滁州市洛达生物科技有限公司 | 1’-氧代靛玉红的制备和用途 |
| CN103627748B (zh) * | 2013-11-21 | 2016-03-30 | 华侨大学 | 一种靛玉红衍生物的制备方法 |
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- 2014-05-26 US US14/779,719 patent/US9868734B2/en not_active Expired - Fee Related
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- 2014-05-26 MX MX2015016217A patent/MX2015016217A/es unknown
- 2014-05-26 KR KR1020157026851A patent/KR20160012984A/ko not_active Withdrawn
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- 2014-05-26 CA CA2912943A patent/CA2912943A1/en not_active Abandoned
- 2014-05-26 RU RU2015140611A patent/RU2015140611A/ru unknown
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| EP3006442A1 (en) | 2016-04-13 |
| EP3006442A4 (en) | 2017-03-08 |
| MX2015016217A (es) | 2016-03-01 |
| CN103333161A (zh) | 2013-10-02 |
| KR20160012984A (ko) | 2016-02-03 |
| US9868734B2 (en) | 2018-01-16 |
| CN103333161B (zh) | 2015-09-30 |
| CN105189486A (zh) | 2015-12-23 |
| CN105189486B (zh) | 2018-07-31 |
| CA2912943A1 (en) | 2014-12-04 |
| RU2015140611A (ru) | 2017-07-04 |
| JP2016519167A (ja) | 2016-06-30 |
| US20160185771A1 (en) | 2016-06-30 |
| WO2014190758A1 (zh) | 2014-12-04 |
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