JP2017516796A5 - - Google Patents
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- Publication number
- JP2017516796A5 JP2017516796A5 JP2016569766A JP2016569766A JP2017516796A5 JP 2017516796 A5 JP2017516796 A5 JP 2017516796A5 JP 2016569766 A JP2016569766 A JP 2016569766A JP 2016569766 A JP2016569766 A JP 2016569766A JP 2017516796 A5 JP2017516796 A5 JP 2017516796A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methylphenyl
- methylpiperazin
- chloro
- substituted
- 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.)
- Granted
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- -1 monocyclic sulfone Chemical class 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 108091008773 RAR-related orphan receptors γ Proteins 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- QPXPWCFEYAVNKD-INIZCTEOSA-N N-[5-chloro-3-[[(3S)-4-(2-cyclopropylacetyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-6-cyanopyridine-3-carboxamide Chemical compound ClC=1C=C(C(=C(C1)NC(C1=CN=C(C=C1)C#N)=O)C)CN1C[C@@H](N(CC1)C(CC1CC1)=O)C QPXPWCFEYAVNKD-INIZCTEOSA-N 0.000 claims description 4
- GRQJEVKIBDYWST-KRWDZBQOSA-N N-[5-chloro-3-[[(3S)-4-(cyclopentanecarbonyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-2-cyanopyridine-4-carboxamide Chemical compound ClC=1C=C(C(=C(C1)NC(C1=CC(=NC=C1)C#N)=O)C)CN1C[C@@H](N(CC1)C(=O)C1CCCC1)C GRQJEVKIBDYWST-KRWDZBQOSA-N 0.000 claims description 4
- FCRIJMWHPMMORC-KRWDZBQOSA-N N-[5-chloro-3-[[(3S)-4-(cyclopentanecarbonyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-5-cyano-6-methylpyridine-3-carboxamide Chemical compound ClC=1C=C(C(=C(C1)NC(C1=CN=C(C(=C1)C#N)C)=O)C)CN1C[C@@H](N(CC1)C(=O)C1CCCC1)C FCRIJMWHPMMORC-KRWDZBQOSA-N 0.000 claims description 4
- DTZVGKPLTWOKMO-KRWDZBQOSA-N N-[5-chloro-3-[[(3S)-4-(cyclopentanecarbonyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-6-cyanopyridine-3-carboxamide Chemical compound ClC=1C=C(C(=C(C1)NC(C1=CN=C(C=C1)C#N)=O)C)CN1C[C@@H](N(CC1)C(=O)C1CCCC1)C DTZVGKPLTWOKMO-KRWDZBQOSA-N 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- QZQHEPUZEQZTTJ-INIZCTEOSA-N 5-N-[5-chloro-3-[[(3S)-4-(cyclopentanecarbonyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]pyridine-2,5-dicarboxamide Chemical compound ClC=1C=C(C(=C(C=1)NC(=O)C=1C=CC(=NC=1)C(=O)N)C)CN1C[C@@H](N(CC1)C(=O)C1CCCC1)C QZQHEPUZEQZTTJ-INIZCTEOSA-N 0.000 claims description 2
- SQZKZGLNOUAVHJ-AWEZNQCLSA-N 5-chloro-N-[3-[[(3S)-4-(2,2-difluorobutanoyl)-3-methylpiperazin-1-yl]methyl]-5-fluoro-2-methylphenyl]-6-methylpyridine-3-carboxamide Chemical compound ClC=1C(=NC=C(C(=O)NC2=C(C(=CC(=C2)F)CN2C[C@@H](N(CC2)C(C(CC)(F)F)=O)C)C)C=1)C SQZKZGLNOUAVHJ-AWEZNQCLSA-N 0.000 claims description 2
- VIXHYTFENNJPFA-AWEZNQCLSA-N 5-chloro-N-[5-chloro-3-[[(3S)-4-(cyclopropanecarbonyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-6-methylpyridine-3-carboxamide Chemical compound ClC=1C(=NC=C(C(=O)NC2=C(C(=CC(=C2)Cl)CN2C[C@@H](N(CC2)C(=O)C2CC2)C)C)C1)C VIXHYTFENNJPFA-AWEZNQCLSA-N 0.000 claims description 2
- ZBSJAIQLGXOESH-HNNXBMFYSA-N 5-chloro-N-[5-fluoro-2-methyl-3-[[(3S)-3-methyl-4-(2-methylpropanoyl)piperazin-1-yl]methyl]phenyl]-6-methylpyridine-3-carboxamide Chemical compound ClC=1C(=NC=C(C(=O)NC2=C(C(=CC(=C2)F)CN2C[C@@H](N(CC2)C(C(C)C)=O)C)C)C1)C ZBSJAIQLGXOESH-HNNXBMFYSA-N 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- RTDYDXFJLKEJIZ-HNNXBMFYSA-N N-[3-[[(3S)-4-butanoyl-3-methylpiperazin-1-yl]methyl]-5-chloro-2-methylphenyl]-5-fluoro-6-methylpyridine-3-carboxamide Chemical compound C(CCC)(=O)N1[C@H](CN(CC1)CC=1C(=C(C=C(C1)Cl)NC(C1=CN=C(C(=C1)F)C)=O)C)C RTDYDXFJLKEJIZ-HNNXBMFYSA-N 0.000 claims description 2
- OJDMEOSJDNLOGJ-HNNXBMFYSA-N N-[3-[[(3S)-4-butanoyl-3-methylpiperazin-1-yl]methyl]-5-fluoro-2-methylphenyl]-5-chloro-6-methylpyridine-3-carboxamide Chemical compound C(CCC)(=O)N1[C@H](CN(CC1)CC=1C(=C(C=C(C1)F)NC(C1=CN=C(C(=C1)Cl)C)=O)C)C OJDMEOSJDNLOGJ-HNNXBMFYSA-N 0.000 claims description 2
- UDUDCWQNJWSRNE-AWEZNQCLSA-N N-[5-chloro-3-[[(3S)-4-(2,2-difluorobutanoyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-5-fluoro-6-methylpyridine-3-carboxamide Chemical compound ClC=1C=C(C(=C(C=1)NC(C1=CN=C(C(=C1)F)C)=O)C)CN1C[C@@H](N(CC1)C(C(CC)(F)F)=O)C UDUDCWQNJWSRNE-AWEZNQCLSA-N 0.000 claims description 2
- NGKHAJANRHPUJR-KRWDZBQOSA-N N-[5-chloro-3-[[(3S)-4-(cyclopentanecarbonyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-4-cyanobutanamide Chemical compound ClC=1C=C(C(=C(C1)NC(CCCC#N)=O)C)CN1C[C@@H](N(CC1)C(=O)C1CCCC1)C NGKHAJANRHPUJR-KRWDZBQOSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000006006 difluoroethoxy group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 229960003966 nicotinamide Drugs 0.000 claims description 2
- 235000005152 nicotinamide Nutrition 0.000 claims description 2
- 239000011570 nicotinamide Substances 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- JMFJGCIRAZWLAO-UHFFFAOYSA-N 2-cyclopropyl-1-(2-methylpiperazin-1-yl)ethanone Chemical compound CC1CNCCN1C(=O)CC1CC1 JMFJGCIRAZWLAO-UHFFFAOYSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 description 1
- PRLNKBJVTMKIGO-UHFFFAOYSA-N 1-(azetidin-1-yl)propan-1-one Chemical group CCC(=O)N1CCC1 PRLNKBJVTMKIGO-UHFFFAOYSA-N 0.000 description 1
- VKCPQGYMMSAKAQ-INIZCTEOSA-N N-[5-chloro-3-[[(3S)-4-(2-cyclopropylacetyl)-3-methylpiperazin-1-yl]methyl]-2-methylphenyl]-5-cyano-6-methylpyridine-3-carboxamide Chemical compound ClC=1C=C(C(=C(C1)NC(C1=CN=C(C(=C1)C#N)C)=O)C)CN1C[C@@H](N(CC1)C(CC1CC1)=O)C VKCPQGYMMSAKAQ-INIZCTEOSA-N 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2014000540 | 2014-05-28 | ||
| CNPCT/CN2014/000540 | 2014-05-28 | ||
| PCT/CN2015/079753 WO2015180612A1 (en) | 2014-05-28 | 2015-05-26 | Novel compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017516796A JP2017516796A (ja) | 2017-06-22 |
| JP2017516796A5 true JP2017516796A5 (enExample) | 2018-07-05 |
| JP6759110B2 JP6759110B2 (ja) | 2020-09-23 |
Family
ID=54698093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016569766A Active JP6759110B2 (ja) | 2014-05-28 | 2015-05-26 | 新規な化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9902735B2 (enExample) |
| EP (1) | EP3148975B1 (enExample) |
| JP (1) | JP6759110B2 (enExample) |
| KR (1) | KR20170012389A (enExample) |
| CN (1) | CN106536489B (enExample) |
| AU (1) | AU2015267909B2 (enExample) |
| BR (1) | BR112016027732B1 (enExample) |
| CA (1) | CA2950211C (enExample) |
| ES (1) | ES2710487T3 (enExample) |
| MX (1) | MX378098B (enExample) |
| RU (1) | RU2016150535A (enExample) |
| WO (1) | WO2015180612A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3219711A1 (en) | 2012-12-06 | 2017-09-20 | Glaxo Group Limited | Modulators of the retinoid-related orphan receptor gamma (ror-gamma) for use in the treatment of autoimmune and inflammatory diseases |
| AU2015267910B2 (en) | 2014-05-28 | 2017-10-26 | Glaxosmithkline Intellectual Property Development Limited | Novel compounds |
| JP6522665B2 (ja) | 2014-05-28 | 2019-05-29 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 新規化合物 |
| CN110167628A (zh) * | 2016-06-23 | 2019-08-23 | 凯斯勒基金会有限公司 | 睾酮替代疗法与神经肌肉刺激组合 |
| SG11201811107WA (en) * | 2016-07-13 | 2019-01-30 | Leo Pharma As | Heteroaromatic modulators of the retinoid-related orphan receptor gamma |
| EP3560918A4 (en) | 2016-12-21 | 2020-05-20 | Jiangsu Hengrui Medicine Co., Ltd. | TRIAZOLE DERIVATIVE FROM THE CONDENSED CYCLE AZACYCLOBUTYL GROUP, PREPARATION METHOD THEREOF AND USE IN MEDICINE |
| EP3564231A4 (en) | 2016-12-28 | 2020-08-12 | Jiangsu Hengrui Medicine Co., Ltd. | AZABICYCLO-SUBSTITUTE TRIAZOLE DERIVATIVE, METHOD OF PREPARATION AND APPLICATION IN MEDICINE |
| CN109134476B (zh) * | 2017-06-15 | 2021-03-19 | 复旦大学 | 桥环哌嗪类衍生物或其盐及其制备方法和用途 |
| JPWO2019022223A1 (ja) * | 2017-07-28 | 2020-06-11 | 東レ株式会社 | 環状アミン誘導体及びその医薬用途 |
| CN107698462A (zh) * | 2017-10-10 | 2018-02-16 | 重庆科脉生物化工有限公司 | 一种1‑氨基‑1‑环丙腈盐酸盐的制备方法 |
| CN109438423A (zh) * | 2018-09-12 | 2019-03-08 | 通化师范学院 | 一种肺癌靶向化合物azd-3759的合成工艺的新方法 |
| CN115244740A (zh) * | 2020-03-06 | 2022-10-25 | 日产化学株式会社 | 新型催化剂组合物以及具有含氮基团的碳材料 |
| WO2021248231A1 (en) * | 2020-06-09 | 2021-12-16 | Relive Therapeutics Inc. | Compounds comprising a three ring core as pd-1/pd-l1 blockers |
| CN116239445B (zh) * | 2023-01-05 | 2024-10-18 | 万华化学集团股份有限公司 | 一种丙内酯开环加氢合成1,3-丙二醇的方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000502100A (ja) * | 1995-12-18 | 2000-02-22 | 藤沢薬品工業株式会社 | タキキニン拮抗薬としてのピペラジン誘導体 |
| US7790726B2 (en) * | 2005-08-16 | 2010-09-07 | Chemocentryx, Inc. | Monocyclic and bicyclic compounds and methods of use |
| US7825120B2 (en) | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| US20070208000A1 (en) | 2005-12-15 | 2007-09-06 | Morgan Bradley P | Certain chemical entities, compositions and methods |
| US7989455B2 (en) | 2005-12-19 | 2011-08-02 | Cytokinetics, Inc. | Compounds, compositions and methods |
| WO2012027965A1 (en) | 2010-09-01 | 2012-03-08 | Glaxo Group Limited | Novel compounds |
| WO2012028100A1 (en) | 2010-09-01 | 2012-03-08 | Glaxo Group Limited | Novel compounds |
| WO2012100734A1 (en) | 2011-01-24 | 2012-08-02 | Glaxo Group Limited | Compounds useful as retinoid-related orphan receptor gamma modulators |
| WO2012100732A1 (en) | 2011-01-24 | 2012-08-02 | Glaxo Group Limited | Retinoid-related orphan receptor gamma modulators, composition containing them and uses thereof |
| EP2511263A1 (en) * | 2011-04-14 | 2012-10-17 | Phenex Pharmaceuticals AG | Pyrrolo sulfonamide compounds for modulation of orphan nuclear receptor RAR-related orphan receptor-gamma (RORgamma, NR1F3) activity and for the treatment of chronic inflammatory and autoimmune diseases |
| WO2012145254A2 (en) | 2011-04-16 | 2012-10-26 | Board Of Regents, The University Of Texas System | Methods of using inhibitors of rorϒt to treat disease |
| PE20141637A1 (es) | 2011-04-28 | 2014-11-20 | Japan Tobacco Inc | Compuesto de amida y aplicacion farmaceutica para el mismo |
| WO2012158784A2 (en) * | 2011-05-16 | 2012-11-22 | Theodore Mark Kamenecka | Modulators of the nuclear hormone receptor ror |
| EP2753327A4 (en) | 2011-09-09 | 2015-04-08 | Univ New York | AMIDOVER BINDINGS AS RORYT MODULATORS AND ITS USE |
| GB201116641D0 (en) | 2011-09-27 | 2011-11-09 | Glaxo Group Ltd | Novel compounds |
| US9428452B2 (en) | 2012-04-27 | 2016-08-30 | Glaxo Group Limited | Compounds |
| GB201207406D0 (en) | 2012-04-27 | 2012-06-13 | Glaxo Group Ltd | Novel compounds |
| EP3219711A1 (en) | 2012-12-06 | 2017-09-20 | Glaxo Group Limited | Modulators of the retinoid-related orphan receptor gamma (ror-gamma) for use in the treatment of autoimmune and inflammatory diseases |
| WO2013171729A2 (en) | 2013-01-08 | 2013-11-21 | Glenmark Pharmaceuticals S.A. | Aryl and heteroaryl amide compounds as rorgamat modulator |
| JP2016534085A (ja) | 2013-10-25 | 2016-11-04 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | 新規化合物 |
| WO2015061686A2 (en) | 2013-10-25 | 2015-04-30 | St. Jude Children's Research Hospital, Inc. | Retinoid x receptor-gamma agonists and retinoid x receptor-alpha antagonists for treatment of cancer |
| JP6522665B2 (ja) | 2014-05-28 | 2019-05-29 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 新規化合物 |
| AU2015267910B2 (en) | 2014-05-28 | 2017-10-26 | Glaxosmithkline Intellectual Property Development Limited | Novel compounds |
-
2015
- 2015-05-26 MX MX2016015630A patent/MX378098B/es unknown
- 2015-05-26 AU AU2015267909A patent/AU2015267909B2/en not_active Ceased
- 2015-05-26 JP JP2016569766A patent/JP6759110B2/ja active Active
- 2015-05-26 US US15/314,111 patent/US9902735B2/en active Active
- 2015-05-26 WO PCT/CN2015/079753 patent/WO2015180612A1/en not_active Ceased
- 2015-05-26 KR KR1020167036017A patent/KR20170012389A/ko not_active Withdrawn
- 2015-05-26 EP EP15800398.8A patent/EP3148975B1/en active Active
- 2015-05-26 BR BR112016027732-5A patent/BR112016027732B1/pt active IP Right Grant
- 2015-05-26 RU RU2016150535A patent/RU2016150535A/ru not_active Application Discontinuation
- 2015-05-26 ES ES15800398T patent/ES2710487T3/es active Active
- 2015-05-26 CA CA2950211A patent/CA2950211C/en active Active
- 2015-05-26 CN CN201580039564.9A patent/CN106536489B/zh active Active
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