MX2013005761A - Derivados de difenilamina: usos, procedimiento de sintesis y composiciones farmaceuticas. - Google Patents
Derivados de difenilamina: usos, procedimiento de sintesis y composiciones farmaceuticas.Info
- Publication number
- MX2013005761A MX2013005761A MX2013005761A MX2013005761A MX2013005761A MX 2013005761 A MX2013005761 A MX 2013005761A MX 2013005761 A MX2013005761 A MX 2013005761A MX 2013005761 A MX2013005761 A MX 2013005761A MX 2013005761 A MX2013005761 A MX 2013005761A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- hydrochloride
- salt
- group
- cancer
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title abstract description 22
- 230000015572 biosynthetic process Effects 0.000 title abstract description 20
- 238000003786 synthesis reaction Methods 0.000 title abstract description 19
- 230000008569 process Effects 0.000 title description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- 150000003839 salts Chemical class 0.000 claims abstract description 70
- 239000012453 solvate Substances 0.000 claims abstract description 28
- 239000000651 prodrug Substances 0.000 claims abstract description 26
- 229940002612 prodrug Drugs 0.000 claims abstract description 26
- 239000003814 drug Substances 0.000 claims abstract description 16
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- -1 heteroaryl radical Chemical class 0.000 claims description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 58
- 229940126214 compound 3 Drugs 0.000 claims description 57
- 206010028980 Neoplasm Diseases 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 206010009944 Colon cancer Diseases 0.000 claims description 18
- 201000011510 cancer Diseases 0.000 claims description 16
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
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- 125000000217 alkyl group Chemical group 0.000 claims description 9
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims description 4
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000003107 substituted aryl group Chemical class 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 3
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 3
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims description 3
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims description 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims description 3
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims description 3
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- JXKAXMCZOZRUQT-UHFFFAOYSA-N n-benzyl-n-ethyl-5,5-diphenylpent-4-en-1-amine Chemical compound C=1C=CC=CC=1CN(CC)CCCC=C(C=1C=CC=CC=1)C1=CC=CC=C1 JXKAXMCZOZRUQT-UHFFFAOYSA-N 0.000 claims description 3
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims description 2
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10382314A EP2465498A1 (en) | 2010-11-23 | 2010-11-23 | Diphenyl-amine derivatives: uses, process of synthesis and pharmaceutical compositions |
| PCT/EP2011/070620 WO2012069442A1 (en) | 2010-11-23 | 2011-11-22 | Diphenyl-amine derivatives: uses, process of synthesis and pharmaceutical compositions |
Publications (1)
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| MX2013005761A true MX2013005761A (es) | 2013-09-26 |
Family
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Family Applications (1)
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| MX2013005761A MX2013005761A (es) | 2010-11-23 | 2011-11-22 | Derivados de difenilamina: usos, procedimiento de sintesis y composiciones farmaceuticas. |
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|---|---|
| US (1) | US20130296346A1 (enExample) |
| EP (2) | EP2465498A1 (enExample) |
| JP (1) | JP2014505662A (enExample) |
| KR (1) | KR20130121888A (enExample) |
| CN (1) | CN103313707A (enExample) |
| AU (1) | AU2011333887A1 (enExample) |
| BR (1) | BR112013012665A2 (enExample) |
| CA (1) | CA2818842A1 (enExample) |
| CL (1) | CL2013001445A1 (enExample) |
| CO (1) | CO6771413A2 (enExample) |
| MA (1) | MA34746B1 (enExample) |
| MX (1) | MX2013005761A (enExample) |
| RU (1) | RU2013128602A (enExample) |
| SA (1) | SA111320943B1 (enExample) |
| UY (1) | UY33745A (enExample) |
| WO (1) | WO2012069442A1 (enExample) |
| ZA (1) | ZA201303692B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS51423B (sr) | 2006-03-31 | 2011-02-28 | Janssen Pharmaceutica N.V. | Benzoimidazol-2-il pirimidini i pirazini kao modulatori histaminskog h4 receptora |
| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
| JP6038882B2 (ja) * | 2011-04-20 | 2016-12-07 | マッパー・リソグラフィー・アイピー・ビー.ブイ. | 光ファイバの構成体及びこのような構成体を形成する方法 |
| JO3516B1 (ar) | 2013-03-06 | 2020-07-05 | Janssen Pharmaceutica Nv | مُعدِّلات بنزإيميدازول-2-يل بيريميدين لمستقبل الهستامين h4 |
| KR101694318B1 (ko) * | 2014-10-02 | 2017-01-09 | 한국과학기술연구원 | 신규한 퓨린 유도체 및 이를 포함하는 암의 예방 또는 치료용 약학 조성물 |
Family Cites Families (7)
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| GB682160A (en) * | 1948-10-18 | 1952-11-05 | Wellcome Found | Improvements in and relating to the preparation of substituted aminoalcohols, alkenylamines, aminoalkanes and quaternary salts thereof |
| US6087346A (en) * | 1993-06-23 | 2000-07-11 | Cambridge Neuroscience, Inc. | Sigma receptor ligands and the use thereof |
| US5795756A (en) | 1995-12-11 | 1998-08-18 | Johnson; Roger A. | Method and compounds for the inhibition of adenylyl cyclase |
| CA2243330A1 (en) * | 1996-01-20 | 1997-07-24 | Ioana Popa | Tamoxifen and analogues thereof |
| DE19756261A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue arylsubstituierte Pyridylalkan-, alken- und alkincarbonsäureamide |
| EP1375502B1 (en) | 2001-04-05 | 2007-06-13 | Sumitomo Chemical Company, Limited | Process for producing 2,6-dihalogenopurine |
| US20050065171A1 (en) | 2003-06-25 | 2005-03-24 | Shakespeare William C. | Substituted purine derivatives |
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2010
- 2010-11-23 EP EP10382314A patent/EP2465498A1/en not_active Withdrawn
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2011
- 2011-11-22 CN CN2011800654202A patent/CN103313707A/zh active Pending
- 2011-11-22 WO PCT/EP2011/070620 patent/WO2012069442A1/en not_active Ceased
- 2011-11-22 CA CA2818842A patent/CA2818842A1/en not_active Abandoned
- 2011-11-22 AU AU2011333887A patent/AU2011333887A1/en not_active Abandoned
- 2011-11-22 KR KR1020137016432A patent/KR20130121888A/ko not_active Withdrawn
- 2011-11-22 UY UY0001033745A patent/UY33745A/es not_active Application Discontinuation
- 2011-11-22 RU RU2013128602/04A patent/RU2013128602A/ru not_active Application Discontinuation
- 2011-11-22 US US13/988,331 patent/US20130296346A1/en not_active Abandoned
- 2011-11-22 EP EP11784710.3A patent/EP2642987A1/en not_active Withdrawn
- 2011-11-22 MX MX2013005761A patent/MX2013005761A/es not_active Application Discontinuation
- 2011-11-22 JP JP2013539296A patent/JP2014505662A/ja active Pending
- 2011-11-22 BR BR112013012665A patent/BR112013012665A2/pt not_active IP Right Cessation
- 2011-11-23 SA SA111320943A patent/SA111320943B1/ar unknown
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2013
- 2013-05-20 CL CL2013001445A patent/CL2013001445A1/es unknown
- 2013-05-21 ZA ZA2013/03692A patent/ZA201303692B/en unknown
- 2013-06-04 CO CO13135212A patent/CO6771413A2/es unknown
- 2013-06-19 MA MA36022A patent/MA34746B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CO6771413A2 (es) | 2013-10-15 |
| AU2011333887A1 (en) | 2013-07-04 |
| CL2013001445A1 (es) | 2014-03-28 |
| KR20130121888A (ko) | 2013-11-06 |
| EP2642987A1 (en) | 2013-10-02 |
| SA111320943B1 (ar) | 2014-12-09 |
| UY33745A (es) | 2012-06-29 |
| US20130296346A1 (en) | 2013-11-07 |
| RU2013128602A (ru) | 2014-12-27 |
| BR112013012665A2 (pt) | 2016-09-06 |
| MA34746B1 (fr) | 2013-12-03 |
| WO2012069442A1 (en) | 2012-05-31 |
| ZA201303692B (en) | 2014-07-30 |
| EP2465498A1 (en) | 2012-06-20 |
| CA2818842A1 (en) | 2012-05-31 |
| CN103313707A (zh) | 2013-09-18 |
| JP2014505662A (ja) | 2014-03-06 |
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