JP2014531402A5 - - Google Patents
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- JP2014531402A5 JP2014531402A5 JP2014523855A JP2014523855A JP2014531402A5 JP 2014531402 A5 JP2014531402 A5 JP 2014531402A5 JP 2014523855 A JP2014523855 A JP 2014523855A JP 2014523855 A JP2014523855 A JP 2014523855A JP 2014531402 A5 JP2014531402 A5 JP 2014531402A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethylphenyl
- maleamic
- amino
- group
- methylphenyl
- 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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- CIIBCTSKJNXPLW-UHFFFAOYSA-N 4-[(3-ethoxy-3-oxopropanoyl)amino]benzoic acid Chemical compound CCOC(=O)CC(=O)NC1=CC=C(C(O)=O)C=C1 CIIBCTSKJNXPLW-UHFFFAOYSA-N 0.000 claims description 29
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 29
- 201000005202 lung cancer Diseases 0.000 claims description 29
- -1 3,4-dimethylphenyl Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 25
- 239000011780 sodium chloride Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (E)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 230000001225 therapeutic Effects 0.000 claims description 4
- INUDQMQHGWTQHO-QXMHVHEDSA-N (Z)-N,N'-bis(4-methoxyphenyl)but-2-enediamide Chemical compound C1=CC(OC)=CC=C1NC(=O)\C=C/C(=O)NC1=CC=C(OC)C=C1 INUDQMQHGWTQHO-QXMHVHEDSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- YKPAUWGAECVSMR-FPLPWBNLSA-N (Z)-N,N'-bis(4-fluoro-2-methylphenyl)but-2-enediamide Chemical compound CC1=CC(F)=CC=C1NC(=O)\C=C/C(=O)NC1=CC=C(F)C=C1C YKPAUWGAECVSMR-FPLPWBNLSA-N 0.000 claims 2
- GQWNPHAMJIUWHR-UHFFFAOYSA-N ethyl 3-(2-chloro-4-hydroxyanilino)-2-methyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)C(=O)NC1=CC=C(O)C=C1Cl GQWNPHAMJIUWHR-UHFFFAOYSA-N 0.000 claims 2
- YCYSBRKDNXTJLH-UHFFFAOYSA-N ethyl 3-(2-chloro-4-hydroxyanilino)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NC1=CC=C(O)C=C1Cl YCYSBRKDNXTJLH-UHFFFAOYSA-N 0.000 claims 2
- GKORTMCOANGAOP-UHFFFAOYSA-N ethyl 3-(anthracen-2-ylamino)-2-methyl-3-oxopropanoate Chemical compound C1=CC=CC2=CC3=CC(NC(=O)C(C)C(=O)OCC)=CC=C3C=C21 GKORTMCOANGAOP-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 66
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
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- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine 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 6
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Claims (4)
- N 1,N4-ãã¹(3,4-ãžã¡ãã«ãã§ãã«)ããã«ã¢ããã
N1,N4-ãž-m-ãã«ã€ã«ããã«ã¢ããã
N1-(2,5-ãžã¡ãã«ãã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1,N4-ãž-m-ãã«ã€ã«ãã¬ã¢ããã
N1-(3,4-ãžã¡ãã«ãã§ãã«)-N4-(4-ãã«ãªã-2-ã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(3,4-ãžã¡ãã«ãã§ãã«)-N4-(3-ãã«ãªã-4-ã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(3,5-ãžã¯ãããã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
(Z)-4-(2,4-ãžã¯ãã -6-ã¡ãã«ãã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
N1-(3,4-ãžã¡ãã«ãã§ãã«)-N4-(3,5-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(3-ããã«ãã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(4-ããã¢ãã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(4-ãã«ãªããã§ãã«)-N4-(3,4-ã¡ããã·ãã§ãã«)ãã¬ã¢ããã
N1-(3-ãšãã«ãã§ãã«)-N4-(4-ãã«ãªããã§ãã«)ãã¬ã¢ããã
(Z)-4-(3 -ãã«ãªã-4-ã¡ãã«ãã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
N 1,N4-ãã¹(3-ãã«ãªã-4-ã¡ãã«ãã§ãã«ïŒããã«ã¢ããã
N1,N4-ãã¹(4-ã¡ããã·ãã§ãã«ïŒãã¬ã¢ããã
N1-(3-ãã«ãªã-4-ã¡ããã·ãã§ãã«)-N4-(ãã«ãªããã§ãã«)ãã¬ã¢ããã
N1,N4-ãã¹(4-ãã«ãªã-2-ã¡ãã«ãã§ãã«ïŒãã¬ã¢ããã
N1-(2,5-ãžã¡ãã«ãã§ãã«ïŒ-N3-(3-ã¡ããã·ãã§ãã«)-2-ã¡ãã«ããã³ã¢ããã
N1-(4-ãã«ãªããã§ãã«)-N4-(m-ãã«ã€ã«ïŒãã¬ã¢ããã
N1-(3,5-ãžã¡ãã«ãã§ãã«ïŒ-N3-(3-ã¡ããã·ãã§ãã«)-2-ã¡ãã«ããã³ã¢ããã
ãšãã«3-(ã¢ã³ãã©ã»ã³-2-ã€ã«ã¢ããïŒ-2-ã¡ãã«-3-ãªããœãããã³é žãšã¹ãã«ã
ãšãã«3- (2-ã¯ãã-4-ããããã·ãã§ãã«ïŒã¢ãã-3-ãªããœãããã³é žãšã¹ã«ã
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4-[(3-ãšããã·-1,3-ãžãªããœãããã«)ã¢ãã]-ãã³ãŸé žã
N1,N4-ãã¹(3,4-ãžã¡ãã«ãã§ãã«)ããã«ã¢ããã
N1,N4-ãž-m-ãã«ã€ã«ããã«ã¢ããã
N1-(2,5-ãžã¡ãã«ãã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1,N4-ãž-m-ãã«ã€ã«ãã¬ã¢ããã
N1-(3,4-ãžã¡ãã«ãã§ãã«)-N4-(4-ãã«ãªã-2-ã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(3,4-ãžã¡ãã«ãã§ãã«)-N4-(3-ãã«ãªã-4-ã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(3,5-ãžã¯ãããã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
(Z)-4-2,5-ãžã¡ãã«ãã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
(Z)-4-3,5-ãžã¡ãã«ãã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
(Z)-4-4-ããã«ãã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
(Z)-4-ãªããœ-4-(m-ãã«ã€ã«ã¢ãã)ããŒã-2-ãšãã€ã¯é žã
(Z)-4-(4-ãã«ãªããã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
(Z)-4-(3,5-ãžã¯ãããã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
(Z)-4-(2,4-ãžã¯ãã -6-ã¡ãã«ãã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
N1-(3,4-ãžã¡ãã«ãã§ãã«)-N4-(3,5-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(3-ããã«ãã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(4-ããã¢ãã§ãã«)-N4-(3,4-ãžã¡ãã«ãã§ãã«)ãã¬ã¢ããã
N1-(4-ãã«ãªããã§ãã«)-N4-(3,4-ã¡ããã·ãã§ãã«)ãã¬ã¢ããã
N1-(3-ãšãã«ãã§ãã«)-N4-(4-ãã«ãªããã§ãã«)ãã¬ã¢ããã
(Z)-4-(3 -ãã«ãªã-4-ã¡ãã«ãã§ãã«)ã¢ãã-4-ãªããœããŒã-2-ãšãã€ã¯é žã
N1,N4-ãã¹(3,5-ãžã¯ãããã§ãã«ïŒããã«ã¢ããã
N1,N4-ãã¹(4-ããã¢ãã§ãã«ïŒããã«ã¢ããã
N1,N4-ãã¹(3,4-ãžã¯ãããã§ãã«ïŒããã«ã¢ããã
N1,N4-ãã¹(3-ãã«ãªã-4-ã¡ãã«ãã§ãã«ïŒããã«ã¢ããã
N1,N4-ãã¹(4-ã¡ããã·ãã§ãã«ïŒãã¬ã¢ããã
N1-(3-ãã«ãªã-4-ã¡ããã·ãã§ãã«)-N4-(ãã«ãªããã§ãã«)ãã¬ã¢ããã
N1,N4-ãã¹(4-ãã«ãªã-2-ã¡ãã«ãã§ãã«ïŒãã¬ã¢ããã
N1-(2,5-ãžã¡ãã«ãã§ãã«ïŒ-N3-(3-ã¡ããã·ãã§ãã«)-2-ã¡ãã«ããã³ã¢ããã
N1-(4-ãã«ãªããã§ãã«)-N4-(m-ãã«ã€ã«ïŒãã¬ã¢ããã
N1-(3,5-ãžã¡ãã«ãã§ãã«ïŒ-N3-(3-ã¡ããã·ãã§ãã«)-2-ã¡ãã«ããã³ã¢ããã
ãšãã«3- (2-ã¯ãã-4-ããããã·ãã§ãã«ïŒã¢ãã-3-ãªããœãããã³é žãšã¹ã«ã
ãšãã«3-(2-ã¯ãã-4-ããããã·ãã§ãã«ïŒã¢ãã-2-ã¡ãã«-3-ãªããœãããã³é žãšã¹ãã«ã
ãããªã矀ããéžã°ããè«æ±é ïŒã«èšèŒã®èºçã®äºé²åã¯æ²»ççšè¬åŠççµæç©ã - ãšãã«3-(ã¢ã³ãã©ã»ã³-2-ã€ã«ã¢ããïŒ-2-ã¡ãã«-3-ãªããœãããã³é žãšã¹ãã«ã§ããã¢ããªã³èªå°äœåã¯ããã®è¬åŠçã«èš±å®¹ãããå¡©ãæå¹æåãšããŠå«ãèºçã®äºé²åã¯æ²»ççšè¬åŠççµæç©ã
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2011-0077863 | 2011-08-04 | ||
KR20110077863 | 2011-08-04 | ||
KR20120041622A KR20130016041A (ko) | 2011-08-04 | 2012-04-20 | ì ê·í ìë늰 ì ë첎 ë° ìŽì ì©ë |
KR10-2012-0041622 | 2012-04-20 | ||
PCT/KR2012/006238 WO2013019093A2 (en) | 2011-08-04 | 2012-08-06 | Novel aniline derivatives and use thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014531402A JP2014531402A (ja) | 2014-11-27 |
JP2014531402A5 true JP2014531402A5 (ja) | 2016-05-19 |
Family
ID=47895706
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2014523855A Pending JP2014531402A (ja) | 2011-08-04 | 2012-08-06 | æ°èŠã¢ããªã³èªå°äœåã³ããã®çšéïŒïŒ®ïœïœïœ ïœïœïœïœïœïœïœïœ ïœïœ ïœïœïœïœïœïœïœïœ ïœïœïœïœïœïœïœ ïœïœïœ ïœïœ ïœïœïŒ |
Country Status (6)
Country | Link |
---|---|
US (1) | US20140142333A1 (ja) |
EP (1) | EP2739279A4 (ja) |
JP (1) | JP2014531402A (ja) |
KR (2) | KR20130016041A (ja) |
CN (1) | CN103889412A (ja) |
WO (1) | WO2013019093A2 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20130118612A (ko) * | 2012-04-20 | 2013-10-30 | (죌)ë€ì€ë¯¹ì€ | ì ê·í ìë¯žë žíŒëŠ¬ë ì ë첎 ë° ìŽì ì©ë |
WO2014179943A1 (zh) * | 2013-05-08 | 2014-11-13 | Yang Yongliang | äžç§é©¬æ¥é °èºååç©ãå ¶å¶å€æ¹æ³åå ¶çšé |
KR101762433B1 (ko) | 2013-06-05 | 2017-07-28 | ì¬ëšë²ìž ììœë°ìŽì€ì»šë²ì Œì€ì°êµ¬ëš | ì ê·í ë§ë ìžì° ì ë첎 ë° ìŽì ì ì¡°ë°©ë² ë° ìŽë¥Œ í¬íšíë íìì© ì¡°ì±ë¬Œ |
KR101514320B1 (ko) | 2013-06-14 | 2015-04-22 | ì¬ëšë²ìž ììœë°ìŽì€ì»šë²ì Œì€ì°êµ¬ëš | ì ê·í ì ìë°© ëë ì¹ë£ì© ìœíì ì¡°ì±ë¬Œ |
KR102297505B1 (ko) * | 2016-03-07 | 2021-09-01 | ì¬ëšë²ìž ììœë°ìŽì€ì»šë²ì Œì€ì°êµ¬ëš | Aimp2-dx2ì hsp70ì ê²°í©ì ì íŽíë íìì ì€í¬ëŠ¬ë ë°©ë² |
KR101831435B1 (ko) * | 2016-03-10 | 2018-02-22 | ì¬ëšë²ìž ììœë°ìŽì€ì»šë²ì Œì€ì°êµ¬ëš | Aimp2-dx2 ëšë°±ì§ì í¹ìŽì ìŒë¡ ê²°í©íë í첎 |
CN111606828B (zh) * | 2019-02-22 | 2023-07-28 | æµæ±æµ·æ£è¯äžè¡ä»œæéå ¬åž | (E)-α,β-äžé¥±åé °èºååç©çæ¶ååå ¶å¶å€æ¹æ³åçšé |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5133610B2 (ja) * | 1973-03-15 | 1976-09-21 | ||
US4125398A (en) * | 1975-11-07 | 1978-11-14 | Ciba-Geigy Corporation | N-Phenyl-maleic acid amides for regulating the growth and development of plants |
CH598213A5 (ja) * | 1976-02-11 | 1978-05-12 | Ciba Geigy Ag | |
SK278455B6 (en) * | 1986-03-31 | 1997-06-04 | Rhone Poulenc Bv | Agent for growth regulation of plants |
JPH02183227A (ja) * | 1989-01-10 | 1990-07-17 | Seizo Miyata | ææ©éç·åœ¢å åŠææ |
JP2683404B2 (ja) * | 1989-02-27 | 1997-11-26 | äžäºæ±å§ååŠæ ªåŒäŒç€Ÿ | âãã§ãã«ãã¬ã€ããååç©ã®è£œé æ¹æ³ |
TW321649B (ja) * | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
KR100433156B1 (ko) | 2001-08-28 | 2004-05-28 | ìëìë§ë 죌ìíì¬ | ìŽêµíêž° |
US20070043076A1 (en) * | 2003-10-06 | 2007-02-22 | Cai Sui X | Substituted 2-arylmethylene-n-aryl-n'aryl-malonamides and analogs as activators of caspases and inducers of apoptosis |
CN1934066A (zh) * | 2004-03-22 | 2007-03-21 | é»å å ¬åž | æäžåè£é©±åšèçœæå¶å |
KR100551009B1 (ko) | 2004-05-20 | 2006-02-13 | ìŒì±ìì€ëììŽ ì£Œìíì¬ | íëŒìŠë§ ëì€íë ìŽ íšë곌 ê·žì 구ëë°©ë² |
WO2006122546A1 (de) * | 2005-05-18 | 2006-11-23 | Forschungsverbund Berlin E.V. | Nicht-peptidische inhibitoren der akap-pka-wechselwirkung |
ES2387707T3 (es) * | 2007-12-21 | 2012-09-28 | Genentech, Inc. | Azaindolizinas y procedimientos de uso |
BR112012000660A2 (pt) * | 2009-06-25 | 2016-11-16 | Amgen Inc | compostos heterociclos e seus usos |
EP2445902A2 (en) * | 2009-06-25 | 2012-05-02 | Amgen, Inc | Heterocyclic compounds and their uses as inhibitors of pi3k activity |
CA2781888C (en) * | 2009-12-11 | 2019-06-18 | Nono Inc. | Agents and methods for treating ischemic and other diseases |
KR20130118612A (ko) * | 2012-04-20 | 2013-10-30 | (죌)ë€ì€ë¯¹ì€ | ì ê·í ìë¯žë žíŒëŠ¬ë ì ë첎 ë° ìŽì ì©ë |
-
2012
- 2012-04-20 KR KR20120041622A patent/KR20130016041A/ko unknown
- 2012-08-06 WO PCT/KR2012/006238 patent/WO2013019093A2/en unknown
- 2012-08-06 EP EP12819363.8A patent/EP2739279A4/en not_active Withdrawn
- 2012-08-06 CN CN201280049088.5A patent/CN103889412A/zh active Pending
- 2012-08-06 KR KR20120085685A patent/KR20130016134A/ko not_active Application Discontinuation
- 2012-08-06 JP JP2014523855A patent/JP2014531402A/ja active Pending
-
2014
- 2014-02-04 US US14/172,055 patent/US20140142333A1/en not_active Abandoned
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