JP2016513111A5 - - Google Patents
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- Publication number
- JP2016513111A5 JP2016513111A5 JP2015558185A JP2015558185A JP2016513111A5 JP 2016513111 A5 JP2016513111 A5 JP 2016513111A5 JP 2015558185 A JP2015558185 A JP 2015558185A JP 2015558185 A JP2015558185 A JP 2015558185A JP 2016513111 A5 JP2016513111 A5 JP 2016513111A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- cycloalkyl
- methyl
- 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 226
- -1 tetrahydro-2H-pyran-4-yl Chemical group 0.000 claims 99
- 125000003118 aryl group Chemical group 0.000 claims 93
- 125000001072 heteroaryl group Chemical group 0.000 claims 77
- 125000005843 halogen group Chemical group 0.000 claims 62
- 229910052799 carbon Inorganic materials 0.000 claims 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 52
- 229910052739 hydrogen Inorganic materials 0.000 claims 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 41
- 229910052757 nitrogen Inorganic materials 0.000 claims 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 27
- 229910052801 chlorine Inorganic materials 0.000 claims 27
- 229910052731 fluorine Inorganic materials 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 26
- 150000002367 halogens Chemical class 0.000 claims 26
- 125000004076 pyridyl group Chemical group 0.000 claims 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 25
- 125000005842 heteroatom Chemical group 0.000 claims 24
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 23
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 22
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 20
- 239000003814 drug Substances 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 17
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 15
- 229940079593 drug Drugs 0.000 claims 15
- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 claims 14
- 125000002720 diazolyl group Chemical group 0.000 claims 14
- 125000001425 triazolyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 125000003386 piperidinyl group Chemical group 0.000 claims 13
- 229910052794 bromium Inorganic materials 0.000 claims 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 12
- 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 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 11
- 150000003839 salts Chemical group 0.000 claims 11
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 11
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 10
- 125000002757 morpholinyl group Chemical group 0.000 claims 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 9
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 125000000732 arylene group Chemical group 0.000 claims 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 8
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 8
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000005549 heteroarylene group Chemical group 0.000 claims 7
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- 125000005551 pyridylene group Chemical group 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims 6
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 235000010290 biphenyl Nutrition 0.000 claims 6
- 239000004305 biphenyl Substances 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 6
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000004419 alkynylene group Chemical group 0.000 claims 5
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000001769 aryl amino group Chemical group 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000001207 fluorophenyl group Chemical group 0.000 claims 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 5
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- RGTBLCLLSZPOKR-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC=NO1 RGTBLCLLSZPOKR-UHFFFAOYSA-N 0.000 claims 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 3
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 102100022422 cGMP-dependent protein kinase 1 Human genes 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 claims 3
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 3
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 2
- 208000018631 connective tissue disease Diseases 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 2
- 210000005003 heart tissue Anatomy 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- 201000006938 muscular dystrophy Diseases 0.000 claims 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 201000006935 Becker muscular dystrophy Diseases 0.000 claims 1
- 102100024316 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A Human genes 0.000 claims 1
- 102100024318 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B Human genes 0.000 claims 1
- 102100024317 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C Human genes 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- 208000007530 Essential hypertension Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101001117044 Homo sapiens Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A Proteins 0.000 claims 1
- 101001117099 Homo sapiens Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B Proteins 0.000 claims 1
- 101001117094 Homo sapiens Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C Proteins 0.000 claims 1
- 206010020880 Hypertrophy Diseases 0.000 claims 1
- 201000009342 Limb-girdle muscular dystrophy Diseases 0.000 claims 1
- 208000001826 Marfan syndrome Diseases 0.000 claims 1
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 1
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims 1
- 201000004239 Secondary hypertension Diseases 0.000 claims 1
- 206010042957 Systolic hypertension Diseases 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000006430 alkyl cyclopropyl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000006383 alkylpyridyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000004706 cardiovascular dysfunction Effects 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019050842A JP6964107B2 (ja) | 2013-02-17 | 2019-03-19 | 新規使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361765804P | 2013-02-17 | 2013-02-17 | |
| US61/765,804 | 2013-02-17 | ||
| PCT/US2014/016741 WO2014127331A1 (en) | 2013-02-17 | 2014-02-17 | Novel uses |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019050842A Division JP6964107B2 (ja) | 2013-02-17 | 2019-03-19 | 新規使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016513111A JP2016513111A (ja) | 2016-05-12 |
| JP2016513111A5 true JP2016513111A5 (https=) | 2017-03-23 |
| JP6549040B2 JP6549040B2 (ja) | 2019-07-24 |
Family
ID=51354608
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015558185A Active JP6549040B2 (ja) | 2013-02-17 | 2014-02-17 | 新規使用 |
| JP2019050842A Active JP6964107B2 (ja) | 2013-02-17 | 2019-03-19 | 新規使用 |
| JP2021129279A Withdrawn JP2021176918A (ja) | 2013-02-17 | 2021-08-05 | 新規使用 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019050842A Active JP6964107B2 (ja) | 2013-02-17 | 2019-03-19 | 新規使用 |
| JP2021129279A Withdrawn JP2021176918A (ja) | 2013-02-17 | 2021-08-05 | 新規使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US9801882B2 (https=) |
| EP (1) | EP2956141A4 (https=) |
| JP (3) | JP6549040B2 (https=) |
| WO (1) | WO2014127331A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012526810A (ja) | 2009-05-13 | 2012-11-01 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| EP2576551A4 (en) | 2010-05-31 | 2014-04-16 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| US9801882B2 (en) | 2013-02-17 | 2017-10-31 | Intra-Cellular Therapies, Inc. | Phosphodiesterase-1 inhibitors and their use in treatment of cardiovascular diseases |
| US10285992B2 (en) | 2014-08-07 | 2019-05-14 | Intra-Cellular Therapies, Inc. | Combinations of PDE1 inhibitors and NEP inhibitors and associated methods |
| US9546175B2 (en) | 2014-08-07 | 2017-01-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US10131671B2 (en) | 2014-08-07 | 2018-11-20 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| JP7134168B6 (ja) * | 2016-09-12 | 2024-02-02 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規使用 |
| JP7401442B2 (ja) | 2018-01-31 | 2023-12-19 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規使用 |
| WO2019241141A1 (en) * | 2018-06-11 | 2019-12-19 | The United States Government As Represented By The Department Of Veterans Affairs | Method for treating myocardial reperfusion injury using an inhibitor of the cyclic nucleotide phosphodiesterase pde1 |
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| EP0077372A1 (de) | 1981-04-22 | 1983-04-27 | Byk Gulden Lomberg Chemische Fabrik GmbH | NEUE PYRAZOLO(3,4-d)PYRIMIDINE, VERFAHREN ZU DEREN HERSTELLUNG UND SIE ENTHALTENDE ARZNEIMITTEL |
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-
2014
- 2014-02-17 US US14/767,489 patent/US9801882B2/en active Active
- 2014-02-17 EP EP14752171.0A patent/EP2956141A4/en active Pending
- 2014-02-17 WO PCT/US2014/016741 patent/WO2014127331A1/en not_active Ceased
- 2014-02-17 JP JP2015558185A patent/JP6549040B2/ja active Active
-
2017
- 2017-09-19 US US15/709,258 patent/US10398698B2/en active Active
-
2019
- 2019-03-19 JP JP2019050842A patent/JP6964107B2/ja active Active
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2021
- 2021-08-05 JP JP2021129279A patent/JP2021176918A/ja not_active Withdrawn
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