JP2016535042A5 - - Google Patents
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- JP2016535042A5 JP2016535042A5 JP2016527174A JP2016527174A JP2016535042A5 JP 2016535042 A5 JP2016535042 A5 JP 2016535042A5 JP 2016527174 A JP2016527174 A JP 2016527174A JP 2016527174 A JP2016527174 A JP 2016527174A JP 2016535042 A5 JP2016535042 A5 JP 2016535042A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- alkyl
- benzo
- carbonitrile
- imidazole
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 claims 20
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 206010061218 Inflammation Diseases 0.000 claims 6
- 206010064930 age-related macular degeneration Diseases 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 230000004054 inflammatory process Effects 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- 206010020751 Hypersensitivity Diseases 0.000 claims 4
- 206010035664 Pneumonia Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 208000026935 allergic disease Diseases 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 230000024203 complement activation Effects 0.000 claims 4
- 208000002780 macular degeneration Diseases 0.000 claims 4
- 230000010410 reperfusion Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 4
- 102000000588 Interleukin-2 Human genes 0.000 claims 3
- 108010002350 Interleukin-2 Proteins 0.000 claims 3
- 230000000295 complement effect Effects 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 230000037361 pathway Effects 0.000 claims 3
- UCKKPCZNZHKBKC-UHFFFAOYSA-N 2-[2,2,2-trifluoro-1-(2-methoxy-4,6-dimethylphenyl)-1-(methylamino)ethyl]-3h-benzimidazole-5-carbonitrile Chemical compound N=1C2=CC=C(C#N)C=C2NC=1C(NC)(C(F)(F)F)C1=C(C)C=C(C)C=C1OC UCKKPCZNZHKBKC-UHFFFAOYSA-N 0.000 claims 2
- JNXUKFKSQBOVHD-UHFFFAOYSA-N 2-[2,2,2-trifluoro-1-methoxy-1-(2-methoxy-4,6-dimethylphenyl)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound FC(C(C1=C(C=C(C=C1C)C)OC)(OC)C1=NC2=C(N1)C=CC(=C2)C#N)(F)F JNXUKFKSQBOVHD-UHFFFAOYSA-N 0.000 claims 2
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000009137 Behcet syndrome Diseases 0.000 claims 2
- 206010006482 Bronchospasm Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 208000008069 Geographic Atrophy Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 2
- 206010070476 Haemodialysis complication Diseases 0.000 claims 2
- 208000000616 Hemoptysis Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010022557 Intermediate uveitis Diseases 0.000 claims 2
- 208000005777 Lupus Nephritis Diseases 0.000 claims 2
- 208000001344 Macular Edema Diseases 0.000 claims 2
- 206010025415 Macular oedema Diseases 0.000 claims 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 2
- 208000010164 Multifocal Choroiditis Diseases 0.000 claims 2
- 208000009525 Myocarditis Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010030924 Optic ischaemic neuropathy Diseases 0.000 claims 2
- 208000030852 Parasitic disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010034277 Pemphigoid Diseases 0.000 claims 2
- 241000721454 Pemphigus Species 0.000 claims 2
- 206010037457 Pulmonary vasculitis Diseases 0.000 claims 2
- 206010063897 Renal ischaemia Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 206010042742 Sympathetic ophthalmia Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 208000001445 Uveomeningoencephalitic Syndrome Diseases 0.000 claims 2
- 208000034705 Vogt-Koyanagi-Harada syndrome Diseases 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 230000007885 bronchoconstriction Effects 0.000 claims 2
- 230000002612 cardiopulmonary effect Effects 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 239000000428 dust Substances 0.000 claims 2
- 238000001631 haemodialysis Methods 0.000 claims 2
- 230000000322 hemodialysis Effects 0.000 claims 2
- 208000007475 hemolytic anemia Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000009610 hypersensitivity Effects 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 201000010230 macular retinal edema Diseases 0.000 claims 2
- 210000003975 mesenteric artery Anatomy 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 201000008383 nephritis Diseases 0.000 claims 2
- 210000005036 nerve Anatomy 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 230000002980 postoperative effect Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 230000008929 regeneration Effects 0.000 claims 2
- 238000011069 regeneration method Methods 0.000 claims 2
- 208000004644 retinal vein occlusion Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 231100000241 scar Toxicity 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000017423 tissue regeneration Effects 0.000 claims 2
- 230000001988 toxicity Effects 0.000 claims 2
- 231100000419 toxicity Toxicity 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- ZMCDQOWTGRFTTD-UHFFFAOYSA-N 2-[(2,6-dimethoxy-4-methylphenyl)-(methylamino)methyl]-3H-benzimidazole-5-carbonitrile Chemical compound COC1=C(C(=CC(=C1)C)OC)C(C1=NC2=C(N1)C=CC(=C2)C#N)NC ZMCDQOWTGRFTTD-UHFFFAOYSA-N 0.000 claims 1
- NCMKKNYDWLDKDG-UHFFFAOYSA-N 2-[1-(3-bromo-6-methoxy-2,4-dimethylphenyl)-2,2,2-trifluoro-1-(methylamino)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound BrC=1C(=C(C(=CC=1C)OC)C(C(F)(F)F)(NC)C1=NC2=C(N1)C=CC(=C2)C#N)C NCMKKNYDWLDKDG-UHFFFAOYSA-N 0.000 claims 1
- AFHFTTWQEBAOCK-UHFFFAOYSA-N 2-[1-(3-bromo-6-methoxy-2,4-dimethylphenyl)-2,2,2-trifluoro-1-hydroxyethyl]-3H-benzimidazole-5-carbonitrile Chemical compound BrC=1C(=C(C(=CC=1C)OC)C(C(F)(F)F)(O)C1=NC2=C(N1)C=CC(=C2)C#N)C AFHFTTWQEBAOCK-UHFFFAOYSA-N 0.000 claims 1
- WMTQFLCFOLOPDJ-UHFFFAOYSA-N 2-[1-(3-chloro-6-methoxy-2,4-dimethylphenyl)-2,2,2-trifluoro-1-(methylamino)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound ClC=1C(=C(C(=CC=1C)OC)C(C(F)(F)F)(NC)C1=NC2=C(N1)C=CC(=C2)C#N)C WMTQFLCFOLOPDJ-UHFFFAOYSA-N 0.000 claims 1
- HIBWVDJGXUSDTF-UHFFFAOYSA-N 2-[1-amino-1-(2-methoxy-4,6-dimethylphenyl)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound NC(C)(C1=C(C=C(C=C1C)C)OC)C1=NC2=C(N1)C=CC(=C2)C#N HIBWVDJGXUSDTF-UHFFFAOYSA-N 0.000 claims 1
- UHLANYZOSFOPQD-UHFFFAOYSA-N 2-[1-amino-2,2,2-trifluoro-1-(2-methoxy-4,6-dimethylphenyl)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound NC(C(F)(F)F)(C1=C(C=C(C=C1C)C)OC)C1=NC2=C(N1)C=CC(=C2)C#N UHLANYZOSFOPQD-UHFFFAOYSA-N 0.000 claims 1
- ZDHYDZQYOXTHDI-UHFFFAOYSA-N 2-[1-hydroxy-1-(2-methoxy-4,6-dimethylphenyl)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound OC(C)(C1=C(C=C(C=C1C)C)OC)C1=NC2=C(N1)C=CC(=C2)C#N ZDHYDZQYOXTHDI-UHFFFAOYSA-N 0.000 claims 1
- MQOBJPBEOVMNLH-UHFFFAOYSA-N 2-[2,2,2-trifluoro-1-(2-methoxy-4-methylphenyl)-1-(methylamino)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound FC(C(NC)(C1=C(C=C(C=C1)C)OC)C1=NC2=C(N1)C=CC(=C2)C#N)(F)F MQOBJPBEOVMNLH-UHFFFAOYSA-N 0.000 claims 1
- LQRITOIKDCFMGX-UHFFFAOYSA-N 2-[2,2,2-trifluoro-1-(2-methoxy-6-methylphenyl)-1-(methylamino)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound FC(C(NC)(C1=C(C=CC=C1C)OC)C1=NC2=C(N1)C=CC(=C2)C#N)(F)F LQRITOIKDCFMGX-UHFFFAOYSA-N 0.000 claims 1
- WOMBWHMMJBYLHH-UHFFFAOYSA-N 2-[2,2,2-trifluoro-1-hydroxy-1-(2-methoxy-4,6-dimethylphenyl)ethyl]-3H-benzimidazole-5-carbonitrile Chemical compound FC(C(C1=C(C=C(C=C1C)C)OC)(O)C1=NC2=C(N1)C=CC(=C2)C#N)(F)F WOMBWHMMJBYLHH-UHFFFAOYSA-N 0.000 claims 1
- JDESVNBQIVCCKU-UHFFFAOYSA-N 2-[amino-(2-methoxy-4,6-dimethylphenyl)methyl]-3H-benzimidazole-5-carbonitrile Chemical compound COc1cc(C)cc(C)c1C(N)c1nc2cc(ccc2[nH]1)C#N JDESVNBQIVCCKU-UHFFFAOYSA-N 0.000 claims 1
- XWIPWDPTJFCDHM-UHFFFAOYSA-N 2-[amino-cyclopropyl-(2-methoxy-4,6-dimethylphenyl)methyl]-3H-benzimidazole-5-carbonitrile Chemical compound NC(C1=NC2=C(N1)C=CC(=C2)C#N)(C1=C(C=C(C=C1C)C)OC)C1CC1 XWIPWDPTJFCDHM-UHFFFAOYSA-N 0.000 claims 1
- ULGNGBHYQFNATA-UHFFFAOYSA-N 2-[hydroxy-(2-methoxy-4,6-dimethylphenyl)methyl]-3H-benzimidazole-5-carbonitrile Chemical compound OC(C1=NC2=C(N1)C=CC(=C2)C#N)C1=C(C=C(C=C1C)C)OC ULGNGBHYQFNATA-UHFFFAOYSA-N 0.000 claims 1
- 208000000059 Dyspnea Diseases 0.000 claims 1
- 206010013975 Dyspnoeas Diseases 0.000 claims 1
- 208000005189 Embolism Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 208000006193 Pulmonary infarction Diseases 0.000 claims 1
- 206010038687 Respiratory distress Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000003352 fibrogenic effect Effects 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 201000006301 pulmonary embolism and infarction Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361897581P | 2013-10-30 | 2013-10-30 | |
| US61/897,581 | 2013-10-30 | ||
| PCT/US2014/063009 WO2015066241A1 (en) | 2013-10-30 | 2014-10-29 | 2-benzyl-benzimidazole complement factor b inhibitors and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016535042A JP2016535042A (ja) | 2016-11-10 |
| JP2016535042A5 true JP2016535042A5 (https=) | 2017-12-07 |
Family
ID=51982745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016527174A Ceased JP2016535042A (ja) | 2013-10-30 | 2014-10-29 | ２−ベンジル−ベンゾイミダゾール補体因子ｂ阻害剤およびその使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9676728B2 (https=) |
| EP (1) | EP3089963A1 (https=) |
| JP (1) | JP2016535042A (https=) |
| CN (1) | CN105849090A (https=) |
| WO (1) | WO2015066241A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR106018A1 (es) | 2015-08-26 | 2017-12-06 | Achillion Pharmaceuticals Inc | Compuestos de arilo, heteroarilo y heterocíclicos para el tratamiento de trastornos médicos |
| WO2017035408A1 (en) | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Compounds for treatment of immune and inflammatory disorders |
| RU2018145364A (ru) | 2016-06-27 | 2020-07-28 | Ачиллион Фармасьютикалс, Инк. | Хиназолиновые и индольные соединения для лечения медицинских нарушений |
| CN110603252A (zh) | 2017-03-01 | 2019-12-20 | 艾其林医药公司 | 用于治疗医学障碍的芳基、杂芳基和杂环药物化合物 |
| MY208400A (en) * | 2018-05-03 | 2025-05-07 | Shanghai hengrui pharmaceutical co ltd | Benzimidazole derivatives as modulators of retinoid-related orphan receptor gamma (ror) and pharmaceutical uses thereof |
| WO2020041301A1 (en) | 2018-08-20 | 2020-02-27 | Achillion Pharmaceuticals, Inc. | Pharmaceutical compounds for the treatment of complement factor d medical disorders |
| US11814363B2 (en) | 2018-09-06 | 2023-11-14 | Achillion Pharmaceuticals, Inc. | Morphic forms of danicopan |
| WO2020051532A2 (en) | 2018-09-06 | 2020-03-12 | Achillion Pharmaceuticals, Inc. | Macrocyclic compounds for the treatment of medical disorders |
| BR112021005506A2 (pt) | 2018-09-25 | 2021-06-15 | Achillion Pharmaceuticals, Inc. | formas mórficas de inibidores de fator complementar d |
| CN109942496B (zh) * | 2019-04-22 | 2022-03-22 | 河南师范大学 | 2-(α-羟基芳基)苯并咪唑类化合物的制备方法 |
| WO2020252407A1 (en) * | 2019-06-12 | 2020-12-17 | The Wistar Institute | Acetyl-coa synthetase 2 (acss2) inhibitors and methods using same |
| WO2021168320A1 (en) | 2020-02-20 | 2021-08-26 | Achillion Pharmaceuticals, Inc. | Heteroaryl compounds for treatment of complement factor d mediated disorders |
| CN114057758A (zh) | 2020-08-07 | 2022-02-18 | 上海美悦生物科技发展有限公司 | 补体因子b抑制剂及其药物组合物、制备方法和用途 |
| EP4194449A4 (en) | 2020-08-07 | 2024-03-20 | Shanghai Meiyue Biotech Development Co., Ltd. | Heterocyclic compound, preparation method therefor and use thereof |
| WO2022066774A1 (en) | 2020-09-23 | 2022-03-31 | Achillion Pharmaceuticals, Inc. | Pharmaceutical compounds for the treatment of complement mediated disorders |
| CA3242815A1 (en) | 2022-01-26 | 2023-08-03 | Shanghai Meiyue Biotech Development Co., Ltd. | Salt type and crystal form of complement factor b inhibitor, and preparation method therefor and application thereof |
| CA3266935A1 (en) | 2022-09-10 | 2024-03-14 | Jiangsu Hansoh Pharmaceutical Group Co., Ltd. | Piperidine derivatives substituted at position 2, their preparation methods and medicinal uses |
| EP4617266A1 (en) | 2022-11-11 | 2025-09-17 | Shanghai Yisheng Biopharmaceutical company Limited | Piperidine-substituted benzoic acid compound, and pharmaceutical composition and use thereof |
| KR20260004425A (ko) | 2023-04-27 | 2026-01-08 | 상하이 한서 바이오메디컬 컴퍼니 리미티드 | 피페리딜인돌 화합물의 염 및 이의 제조 방법 |
| CN119371402A (zh) | 2023-07-26 | 2025-01-28 | 上海美悦生物科技发展有限公司 | 螺环烯基类或氮杂烯基类化合物及其药物组合物、制备方法和用途 |
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-
2014
- 2014-10-29 EP EP14802972.1A patent/EP3089963A1/en not_active Withdrawn
- 2014-10-29 CN CN201480071438.7A patent/CN105849090A/zh active Pending
- 2014-10-29 JP JP2016527174A patent/JP2016535042A/ja not_active Ceased
- 2014-10-29 US US15/032,872 patent/US9676728B2/en not_active Expired - Fee Related
- 2014-10-29 WO PCT/US2014/063009 patent/WO2015066241A1/en not_active Ceased
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