JP2010518082A5 - - Google Patents
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- JP2010518082A5 JP2010518082A5 JP2009549102A JP2009549102A JP2010518082A5 JP 2010518082 A5 JP2010518082 A5 JP 2010518082A5 JP 2009549102 A JP2009549102 A JP 2009549102A JP 2009549102 A JP2009549102 A JP 2009549102A JP 2010518082 A5 JP2010518082 A5 JP 2010518082A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- aryl
- alkoxy
- hydroxy
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims description 152
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 125000000623 heterocyclic group Chemical group 0.000 claims description 53
- -1 substituted Chemical class 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000001589 carboacyl group Chemical group 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 12
- 150000003904 phospholipids Chemical class 0.000 claims description 11
- 125000003435 aroyl group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002502 liposome Substances 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 8
- MWRBNPKJOOWZPW-CLFAGFIQSA-N dioleoyl phosphatidylethanolamine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-CLFAGFIQSA-N 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- OYCDTPQIKJZGBS-UHFFFAOYSA-N P(O)(O)(O)=O.[O] Chemical compound P(O)(O)(O)=O.[O] OYCDTPQIKJZGBS-UHFFFAOYSA-N 0.000 claims 2
- 238000006735 epoxidation reaction Methods 0.000 claims 2
- 230000033444 hydroxylation Effects 0.000 claims 2
- 238000005805 hydroxylation reaction Methods 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 42
- 238000000034 method Methods 0.000 description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 14
- 108090000765 processed proteins & peptides Proteins 0.000 description 10
- 239000011324 bead Substances 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 7
- 229920002521 macromolecule Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 5
- 102000002689 Toll-like receptor Human genes 0.000 description 5
- 108020000411 Toll-like receptor Proteins 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000539 amino acid group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000000412 dendrimer Substances 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 239000002105 nanoparticle Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 208000035143 Bacterial infection Diseases 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 150000007523 nucleic acids Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000186781 Listeria Species 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 230000000890 antigenic effect Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 241000681036 Barbella Species 0.000 description 1
- 241000711573 Coronaviridae Species 0.000 description 1
- 241000711549 Hepacivirus C Species 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 241000713666 Lentivirus Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 108010020346 Polyglutamic Acid Proteins 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 102100039390 Toll-like receptor 7 Human genes 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical group NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940044616 toll-like receptor 7 agonist Drugs 0.000 description 1
- 229940044655 toll-like receptor 9 agonist Drugs 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
Images
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88869907P | 2007-02-07 | 2007-02-07 | |
| US60/888,699 | 2007-02-07 | ||
| PCT/US2008/001631 WO2008115319A2 (en) | 2007-02-07 | 2008-02-07 | Conjugates of synthetic tlr agonists and uses therefor |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013059721A Division JP2013127004A (ja) | 2007-02-07 | 2013-03-22 | 合成tlrアゴニストの結合体およびそのための使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010518082A JP2010518082A (ja) | 2010-05-27 |
| JP2010518082A5 true JP2010518082A5 (cg-RX-API-DMAC7.html) | 2011-03-31 |
| JP5425642B2 JP5425642B2 (ja) | 2014-02-26 |
Family
ID=39766655
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009549102A Expired - Fee Related JP5425642B2 (ja) | 2007-02-07 | 2008-02-07 | 合成tlrアゴニストの結合体およびそのための使用 |
| JP2013059721A Withdrawn JP2013127004A (ja) | 2007-02-07 | 2013-03-22 | 合成tlrアゴニストの結合体およびそのための使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013059721A Withdrawn JP2013127004A (ja) | 2007-02-07 | 2013-03-22 | 合成tlrアゴニストの結合体およびそのための使用 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US8357374B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP2125007B9 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5425642B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR20090109121A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101790380B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2008227128B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0807196A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2677733A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK2510946T3 (cg-RX-API-DMAC7.html) |
| EA (1) | EA019151B1 (cg-RX-API-DMAC7.html) |
| ES (2) | ES2456964T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUE025555T2 (cg-RX-API-DMAC7.html) |
| IL (1) | IL200240A (cg-RX-API-DMAC7.html) |
| PL (2) | PL2125007T3 (cg-RX-API-DMAC7.html) |
| PT (1) | PT2510946E (cg-RX-API-DMAC7.html) |
| SI (1) | SI2510946T1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008115319A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200906094B (cg-RX-API-DMAC7.html) |
Families Citing this family (122)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101304748A (zh) | 2005-08-22 | 2008-11-12 | 加利福尼亚大学董事会 | Tlr激动剂 |
| CA2653941C (en) | 2006-05-31 | 2013-01-08 | The Regents Of The University Of California | Substituted amino purine derivatives and uses thereof |
| EA019151B1 (ru) | 2007-02-07 | 2014-01-30 | Дзе Регентс Оф Дзе Юниверсити Оф Калифорния | Конъюгаты синтетических агонистов tlr и их применение |
| EP2211841A4 (en) * | 2007-10-15 | 2013-03-13 | Cooperative Res Ct For Asthma | METHOD FOR PROPHYLAXIS AND AGENTS FOR USE THEREIN |
| JP2011511073A (ja) * | 2008-02-07 | 2011-04-07 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | Tlr7活性化物質による膀胱の疾患の治療 |
| WO2010088924A1 (en) | 2009-02-06 | 2010-08-12 | Telormedix Sa | Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration |
| EP2396328A2 (en) | 2009-02-11 | 2011-12-21 | The Regents of The University of California | Toll-like receptor modulators and treatment of diseases |
| EP2435094A2 (en) | 2009-05-27 | 2012-04-04 | Selecta Biosciences, Inc. | Targeted synthetic nanocarriers with ph sensitive release of immunomodulatory agents |
| SI2491035T1 (sl) | 2009-10-22 | 2017-10-30 | Gilead Sciences, Inc. | Derivati purina ali deazapurina uporabni za zdravljenje (med drugimi) virusnih okužb |
| JP2013525431A (ja) * | 2010-04-30 | 2013-06-20 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 合成tlr7アゴニストのリン脂質結合体の使用 |
| AU2011247359A1 (en) * | 2010-04-30 | 2012-11-15 | Telormedix Sa | Methods for inducing an immune response |
| KR20130056249A (ko) * | 2010-04-30 | 2013-05-29 | 텔로메딕스 에스에이 | 인지질 약물 유사체 |
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| TR201815062T4 (tr) | 2011-04-08 | 2018-11-21 | Janssen Sciences Ireland Uc | Viral enfeksiyonların tedavisine yönelik pirimidin deriveleri. |
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| AU2012261959B2 (en) | 2011-06-03 | 2015-12-03 | Solventum Intellectual Properties Company | Hydrazino 1H-imidazoquinolin-4-amines and conjugates made therefrom |
| MX2014001142A (es) | 2011-07-29 | 2014-02-27 | Selecta Biosciences Inc | Nanoportadores sinteticos que generan respuestas inmunitarias humorales y de linfocitos t citotoxicos (ctl). |
| KR102025276B1 (ko) | 2011-11-09 | 2019-09-25 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 바이러스 감염 치료를 위한 퓨린 유도체 |
| EP3563872A1 (en) | 2012-04-05 | 2019-11-06 | Massachusetts Institute Of Technology | Immunostimulatory compositions and methods of use thereof |
| PL2872515T3 (pl) | 2012-07-13 | 2017-05-31 | Janssen Sciences Ireland Uc | Puryny makrocykliczne do leczenia infekcji wirusowych |
| CN103566377A (zh) * | 2012-07-18 | 2014-02-12 | 上海博笛生物科技有限公司 | 癌症的靶向免疫治疗 |
| WO2014052828A1 (en) | 2012-09-27 | 2014-04-03 | The Regents Of The University Of California | Compositions and methods for modulating tlr4 |
| MX386924B (es) | 2012-10-10 | 2025-03-19 | Janssen Sciences Ireland Uc | Derivados pirrolo[3,2-d]pirimidínicos para el tratamiento de infecciones víricas y otras enfermedades. |
| CN105061567B (zh) * | 2012-10-10 | 2021-07-20 | 深圳大学 | 免疫受体调节剂偶联体及其制备方法和应用、制备其的偶联前体以及合成偶联前体的化合物 |
| EA035431B1 (ru) | 2012-11-16 | 2020-06-15 | Янссен Сайенсиз Айрлэнд Юси | Гетероциклические замещенные производные 2-амино-хиназолина в качестве модуляторов tlr7 и/или tlr8 для лечения вирусных инфекций |
| SG11201506639XA (en) | 2013-02-21 | 2015-09-29 | Janssen Sciences Ireland Uc | 2-aminopyrimidine derivatives for the treatment of viral infections |
| EP2958889B1 (en) * | 2013-02-25 | 2017-03-22 | The Scripps Research Institute | Neoseptins: small molecule adjuvants |
| AU2014240165A1 (en) * | 2013-03-14 | 2015-10-01 | Rongfu Wang | Methods and compositions for modulating regulatory T cell function |
| WO2014144365A1 (en) * | 2013-03-15 | 2014-09-18 | University Of Maryland, College Park | Nano-liposomal formulations and methods of use |
| AU2014242954B2 (en) * | 2013-03-29 | 2018-03-15 | Janssen Sciences Ireland Uc | Macrocyclic deaza-purinones for the treatment of viral infections |
| KR102280559B1 (ko) | 2013-05-24 | 2021-07-22 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 바이러스 감염 및 추가적인 질환의 치료를 위한 피리돈 유도체 |
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| EA032824B1 (ru) * | 2014-08-15 | 2019-07-31 | Чиа Тай Тяньцин Фармасьютикал Груп Ко., Лтд. | Пирролопиримидиновые соединения, используемые в качестве агониста tlr7 |
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| AU2011247359A1 (en) | 2010-04-30 | 2012-11-15 | Telormedix Sa | Methods for inducing an immune response |
| KR20130056249A (ko) | 2010-04-30 | 2013-05-29 | 텔로메딕스 에스에이 | 인지질 약물 유사체 |
| BR112013005134A2 (pt) | 2010-09-01 | 2018-04-24 | Novartis Ag | adsorção de imunopotenciadores em sais metálicos insolúveis |
| WO2012038058A1 (en) | 2010-09-21 | 2012-03-29 | Telormedix Sa | Treatment of conditions by toll-like receptor modulators |
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2008
- 2008-02-07 EA EA200901078A patent/EA019151B1/ru unknown
- 2008-02-07 ES ES08799591.6T patent/ES2456964T3/es active Active
- 2008-02-07 PL PL08799591T patent/PL2125007T3/pl unknown
- 2008-02-07 KR KR1020097018499A patent/KR20090109121A/ko not_active Ceased
- 2008-02-07 CA CA002677733A patent/CA2677733A1/en not_active Abandoned
- 2008-02-07 EP EP08799591.6A patent/EP2125007B9/en active Active
- 2008-02-07 WO PCT/US2008/001631 patent/WO2008115319A2/en not_active Ceased
- 2008-02-07 JP JP2009549102A patent/JP5425642B2/ja not_active Expired - Fee Related
- 2008-02-07 PL PL12004181T patent/PL2510946T3/pl unknown
- 2008-02-07 US US12/027,960 patent/US8357374B2/en active Active
- 2008-02-07 BR BRPI0807196-9A2A patent/BRPI0807196A2/pt not_active Application Discontinuation
- 2008-02-07 PT PT120041819T patent/PT2510946E/pt unknown
- 2008-02-07 EP EP12004181.9A patent/EP2510946B1/en active Active
- 2008-02-07 AU AU2008227128A patent/AU2008227128B2/en active Active
- 2008-02-07 HU HUE12004181A patent/HUE025555T2/en unknown
- 2008-02-07 ES ES12004181.9T patent/ES2552471T3/es active Active
- 2008-02-07 SI SI200831521T patent/SI2510946T1/sl unknown
- 2008-02-07 DK DK12004181.9T patent/DK2510946T3/en active
- 2008-02-07 CN CN2008800115258A patent/CN101790380B/zh active Active
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2009
- 2009-08-05 IL IL200240A patent/IL200240A/en active IP Right Grant
- 2009-09-02 ZA ZA2009/06094A patent/ZA200906094B/en unknown
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2013
- 2013-01-08 US US13/736,545 patent/US8790655B2/en active Active
- 2013-03-22 JP JP2013059721A patent/JP2013127004A/ja not_active Withdrawn
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2014
- 2014-06-19 US US14/309,245 patent/US9050376B2/en active Active
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