JP2016518343A5 - - Google Patents
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- JP2016518343A5 JP2016518343A5 JP2016503395A JP2016503395A JP2016518343A5 JP 2016518343 A5 JP2016518343 A5 JP 2016518343A5 JP 2016503395 A JP2016503395 A JP 2016503395A JP 2016503395 A JP2016503395 A JP 2016503395A JP 2016518343 A5 JP2016518343 A5 JP 2016518343A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- optionally
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 227
- -1 tetrahydro-2H-pyran-4-yl Chemical group 0.000 claims 104
- 125000003118 aryl group Chemical group 0.000 claims 93
- 125000001072 heteroaryl group Chemical group 0.000 claims 81
- 125000005843 halogen group Chemical group 0.000 claims 60
- 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 42
- 125000004076 pyridyl group Chemical group 0.000 claims 35
- 229910052757 nitrogen Inorganic materials 0.000 claims 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 32
- 229910052731 fluorine Inorganic materials 0.000 claims 29
- 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
- 229910052736 halogen Inorganic materials 0.000 claims 26
- 150000002367 halogens Chemical class 0.000 claims 26
- 125000005842 heteroatom Chemical group 0.000 claims 26
- 239000003814 drug Substances 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 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 20
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 19
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 16
- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 claims 16
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 15
- 208000014674 injury Diseases 0.000 claims 15
- 125000002720 diazolyl group Chemical group 0.000 claims 14
- 125000001425 triazolyl group Chemical group 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 208000035475 disorder Diseases 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 11
- 150000003839 salts Chemical group 0.000 claims 11
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 11
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[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
- 208000027418 Wounds and injury Diseases 0.000 claims 10
- 230000006378 damage Effects 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
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 9
- 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
- 208000015114 central nervous system disease Diseases 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 9
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 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
- 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
- 125000004429 atom 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
- 230000003834 intracellular effect Effects 0.000 claims 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 7
- 125000005551 pyridylene group Chemical group 0.000 claims 7
- 208000020431 spinal cord injury Diseases 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 6
- 235000010290 biphenyl Nutrition 0.000 claims 6
- 239000004305 biphenyl Substances 0.000 claims 6
- 208000029028 brain injury Diseases 0.000 claims 6
- 229910052791 calcium Inorganic materials 0.000 claims 6
- 239000011575 calcium Substances 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- RGTBLCLLSZPOKR-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC=NO1 RGTBLCLLSZPOKR-UHFFFAOYSA-N 0.000 claims 5
- 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
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 5
- 230000008733 trauma Effects 0.000 claims 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 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
- 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
- 206010061218 Inflammation Diseases 0.000 claims 3
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 230000004054 inflammatory process Effects 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
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[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
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer 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
- 231100000317 environmental toxin Toxicity 0.000 claims 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 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
- 239000000523 sample Substances 0.000 claims 2
- 238000001356 surgical procedure Methods 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
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims 1
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
- 208000024412 Friedreich ataxia Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 208000001089 Multiple system atrophy Diseases 0.000 claims 1
- 206010033892 Paraplegia Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 102000029797 Prion Human genes 0.000 claims 1
- 108091000054 Prion Proteins 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 206010057430 Retinal injury Diseases 0.000 claims 1
- 208000032930 Spastic paraplegia Diseases 0.000 claims 1
- 208000009415 Spinocerebellar Ataxias 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
- 206010002022 amyloidosis Diseases 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 239000012472 biological sample Substances 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 230000006931 brain damage Effects 0.000 claims 1
- 231100000874 brain damage Toxicity 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 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
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 230000037041 intracellular level Effects 0.000 claims 1
- 125000001288 lysyl group Chemical group 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 208000027232 peripheral nervous system disease Diseases 0.000 claims 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 231100000765 toxin Toxicity 0.000 claims 1
- 239000003053 toxin Substances 0.000 claims 1
- 108700012359 toxins Proteins 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361799603P | 2013-03-15 | 2013-03-15 | |
| US61/799,603 | 2013-03-15 | ||
| PCT/US2014/030412 WO2014145617A2 (en) | 2013-03-15 | 2014-03-17 | Novel uses |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018200930A Division JP2019031544A (ja) | 2013-03-15 | 2018-10-25 | 新規使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016518343A JP2016518343A (ja) | 2016-06-23 |
| JP2016518343A5 true JP2016518343A5 (enExample) | 2017-04-13 |
Family
ID=51538509
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016503395A Withdrawn JP2016518343A (ja) | 2013-03-15 | 2014-03-17 | 新規使用 |
| JP2018200930A Withdrawn JP2019031544A (ja) | 2013-03-15 | 2018-10-25 | 新規使用 |
| JP2020034938A Pending JP2020105186A (ja) | 2013-03-15 | 2020-03-02 | 新規使用 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018200930A Withdrawn JP2019031544A (ja) | 2013-03-15 | 2018-10-25 | 新規使用 |
| JP2020034938A Pending JP2020105186A (ja) | 2013-03-15 | 2020-03-02 | 新規使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (4) | US9545406B2 (enExample) |
| EP (2) | EP2968338B1 (enExample) |
| JP (3) | JP2016518343A (enExample) |
| ES (2) | ES2717688T3 (enExample) |
| WO (1) | WO2014145617A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2968338B1 (en) | 2013-03-15 | 2019-01-09 | Intra-Cellular Therapies, Inc. | Pde1 inhibitors for use in the treatment and/or prevention of cns injuries, and pns diseases, disorders or injuries |
| JP2019510039A (ja) | 2016-03-28 | 2019-04-11 | イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. | 新規組成物および方法 |
| 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 |
| EP3746081A4 (en) * | 2018-01-31 | 2021-10-27 | Intra-Cellular Therapies, Inc. | Novel uses |
| US11980617B2 (en) | 2018-03-16 | 2024-05-14 | Intra-Cellular Therapies, Inc. | Methods of treating acute depression and/or acute anxiety |
| CN112189013A (zh) * | 2018-05-25 | 2021-01-05 | 细胞内治疗公司 | 有机化合物 |
| CA3102948A1 (en) | 2018-06-08 | 2019-12-12 | Intra-Cellular Therapies, Inc. | Novel methods |
| 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 |
| WO2020146384A1 (en) | 2019-01-07 | 2020-07-16 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US11628171B2 (en) * | 2019-03-13 | 2023-04-18 | Children's Medical Center Corporation | Method for treating brain or nerve injury |
| EP4413980A3 (en) * | 2019-09-03 | 2024-10-30 | Intra-Cellular Therapies, Inc. | Novel compounds |
| US20230355625A1 (en) * | 2019-11-27 | 2023-11-09 | Intra-Cellular Therapies, Inc. | Methods of treatment |
| US12364695B2 (en) | 2020-06-02 | 2025-07-22 | Intra-Cellular Therapies, Inc. | Methods of treating inflammatory disease |
| US20250144029A1 (en) * | 2022-01-27 | 2025-05-08 | Intra-Cellular Therapies, Inc. | Novel compositions |
| US20250195510A1 (en) | 2022-05-18 | 2025-06-19 | Intra-Cellular Therapies, Inc. | Novel methods |
| WO2025111568A1 (en) | 2023-11-22 | 2025-05-30 | Intra-Cellular Therapies, Inc. | Lumateperone and analogues, as 5-ht2a or 5-ht2a/d2 receptor modulators, for use in the treatment of psychiatric disorders caused by viral, bacterial, or autoimmune encephalitis, and of psychiatric symptoms thereof |
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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
- 2014-03-17 EP EP14763482.8A patent/EP2968338B1/en active Active
- 2014-03-17 ES ES14763482T patent/ES2717688T3/es active Active
- 2014-03-17 EP EP18205841.2A patent/EP3479825B1/en active Active
- 2014-03-17 JP JP2016503395A patent/JP2016518343A/ja not_active Withdrawn
- 2014-03-17 WO PCT/US2014/030412 patent/WO2014145617A2/en not_active Ceased
- 2014-03-17 ES ES18205841T patent/ES2871327T3/es active Active
- 2014-03-17 US US14/777,448 patent/US9545406B2/en active Active
-
2017
- 2017-01-13 US US15/406,346 patent/US10183023B2/en active Active
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2018
- 2018-10-25 JP JP2018200930A patent/JP2019031544A/ja not_active Withdrawn
- 2018-12-13 US US16/219,589 patent/US10682355B2/en active Active
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2020
- 2020-03-02 JP JP2020034938A patent/JP2020105186A/ja active Pending
- 2020-05-20 US US16/879,676 patent/US11504372B2/en active Active
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