JP2013545808A5 - - Google Patents
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- Publication number
- JP2013545808A5 JP2013545808A5 JP2013544674A JP2013544674A JP2013545808A5 JP 2013545808 A5 JP2013545808 A5 JP 2013545808A5 JP 2013544674 A JP2013544674 A JP 2013544674A JP 2013544674 A JP2013544674 A JP 2013544674A JP 2013545808 A5 JP2013545808 A5 JP 2013545808A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- alkoxy
- compound
- hetcyc
- 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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- 150000001875 compounds Chemical class 0.000 claims description 163
- 125000000217 alkyl group Chemical group 0.000 claims description 156
- 125000003545 alkoxy group Chemical group 0.000 claims description 101
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 15
- -1 pyridinonyl Chemical group 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 8
- 229910017051 nitrogen difluoride Inorganic materials 0.000 claims description 8
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 230000004761 fibrosis Effects 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 2
- JUQWFONZRDXAAB-UHFFFAOYSA-N 1-methyl-1-oxidopiperazin-1-ium Chemical compound C[N+]1([O-])CCNCC1 JUQWFONZRDXAAB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 150000001723 carbon free-radicals Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000002831 nitrogen free-radicals Chemical class 0.000 claims 1
- 0 *c1n[n](*)c2c1c(NC(C(CCC1CC=C3*)=CN=C1C=C3F)=O)c(*)cc2 Chemical compound *c1n[n](*)c2c1c(NC(C(CCC1CC=C3*)=CN=C1C=C3F)=O)c(*)cc2 0.000 description 4
- 238000000034 method Methods 0.000 description 2
- YSDBJKNOEWSFGA-UHFFFAOYSA-N CC(N1CCN(C)CC1)=O Chemical compound CC(N1CCN(C)CC1)=O YSDBJKNOEWSFGA-UHFFFAOYSA-N 0.000 description 1
- YJKPIKTXJCGEJS-UHFFFAOYSA-N CC(NC1CN(C)CC1)=O Chemical compound CC(NC1CN(C)CC1)=O YJKPIKTXJCGEJS-UHFFFAOYSA-N 0.000 description 1
- HDCCJUCOIKLZNM-UHFFFAOYSA-N CC(NC1CNCC1)=O Chemical compound CC(NC1CNCC1)=O HDCCJUCOIKLZNM-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42254710P | 2010-12-13 | 2010-12-13 | |
| US61/422,547 | 2010-12-13 | ||
| PCT/US2011/064549 WO2012082689A1 (en) | 2010-12-13 | 2011-12-13 | SUBSTITUTED N-(1H-INDAZOL-4-YL)IMIDAZO[1,2-a]PYRIDINE-3-CARBOXAMIDE COMPOUNDS AS TYPE III RECEPTOR TYROSINE KINASE INHIBITORS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015205806A Division JP2016040303A (ja) | 2010-12-13 | 2015-10-19 | ＩＩＩ型受容体チロシンキナーゼ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013545808A JP2013545808A (ja) | 2013-12-26 |
| JP2013545808A5 true JP2013545808A5 (enExample) | 2015-02-05 |
| JP5868996B2 JP5868996B2 (ja) | 2016-02-24 |
Family
ID=45478484
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013544674A Expired - Fee Related JP5868996B2 (ja) | 2010-12-13 | 2011-12-13 | ＩＩＩ型受容体チロシンキナーゼ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
| JP2015205806A Withdrawn JP2016040303A (ja) | 2010-12-13 | 2015-10-19 | ＩＩＩ型受容体チロシンキナーゼ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
| JP2017227134A Withdrawn JP2018065835A (ja) | 2010-12-13 | 2017-11-27 | ＩＩＩ型受容体チロシンキナーゼ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015205806A Withdrawn JP2016040303A (ja) | 2010-12-13 | 2015-10-19 | ＩＩＩ型受容体チロシンキナーゼ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
| JP2017227134A Withdrawn JP2018065835A (ja) | 2010-12-13 | 2017-11-27 | ＩＩＩ型受容体チロシンキナーゼ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
Country Status (32)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101779630B1 (ko) * | 2009-12-21 | 2017-09-18 | 어레이 바이오파마 인크. | ｃＦＭＳ 억제제로서 치환된 Ｎ-（１Ｈ-인다졸-４-일）이미다조［１,２-ａ］피리딘-３-카복사미드 화합물 |
| UY33801A (es) | 2010-12-13 | 2013-06-28 | Array Biopharma Inc | COMPUESTOS SUSTITUIDOS DE N-(1H-INDAZOL-4IL)IMIDAZO[1,2-a]PIRIDIN-3-CARBOXAMIDA COMO INHIBIDORES DE LA TIROSINA QUINASA RECEPTORA DE TIPO III |
| GB201315486D0 (en) * | 2013-08-30 | 2013-10-16 | Ucb Pharma Sa | Antibodies |
| JO3517B1 (ar) | 2014-01-17 | 2020-07-05 | Novartis Ag | ان-ازاسبيرو الكان حلقي كبديل مركبات اريل-ان مغايرة وتركيبات لتثبيط نشاط shp2 |
| CN104496891A (zh) * | 2014-12-06 | 2015-04-08 | 哈尔滨工业大学 | 吡啶衍生物2-叔丁氧基-6-亚甲基氯吡啶的合成方法 |
| CN104974078A (zh) * | 2015-06-25 | 2015-10-14 | 黄荣辉 | 一种2-甲基-6-氯甲基吡啶盐酸盐的制备方法 |
| US10836742B2 (en) | 2015-08-11 | 2020-11-17 | Neomed Institute | N-substituted bicyclic lactams, their preparation and their use as pharmaceuticals |
| US10501438B2 (en) | 2015-08-11 | 2019-12-10 | Neomed Institute | Aryl-substituted dihydroquinolinones, their preparation and their use as pharmaceuticals |
| CN114605387A (zh) | 2015-08-12 | 2022-06-10 | 埃皮吉纳提克斯股份有限公司 | 取代的苯并咪唑、它们的制备和它们作为药物的用途 |
| US10501459B2 (en) | 2015-10-21 | 2019-12-10 | Neomed Institute | Substituted imidazo[1,2-a]pyridines as bromodomain inhibitors |
| EP3974424A1 (en) * | 2015-11-02 | 2022-03-30 | Genase Therapeutics B.V. | Tetrahydroindazoles and medical uses thereof |
| CN105198799A (zh) * | 2015-11-03 | 2015-12-30 | 江苏梦得电镀化学品有限公司 | 一种2-甲基-6-氯甲基吡啶盐酸盐的制备方法 |
| US10519151B2 (en) | 2016-01-28 | 2019-12-31 | Neomed Institute | Substituted [1,2,4]triazolo[4,3-A]pyridines, their preparation and their use as pharmaceuticals |
| RU2744988C2 (ru) | 2016-06-14 | 2021-03-17 | Новартис Аг | Соединения и композиции для подавления активности shp2 |
| CN106187899B (zh) * | 2016-06-28 | 2019-07-16 | 绍兴文理学院 | 一种氟代氮杂芳烃的合成方法 |
| CN109790079B (zh) * | 2016-07-29 | 2022-06-03 | 香港科技大学 | 有机锌试剂与杂环(拟)卤化物的C(sp3)-C(sp2)交叉偶联反应 |
| WO2018083635A2 (en) | 2016-11-04 | 2018-05-11 | Auckland Uniservices Limited | Tricyclic heterocyclic derivatives and uses thereof |
| JP6346368B1 (ja) * | 2016-11-28 | 2018-06-20 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | インダゾール誘導体の塩及びその結晶 |
| WO2018213665A1 (en) | 2017-05-19 | 2018-11-22 | Syndax Pharmaceuticals, Inc. | Combination therapies |
| MD3658552T2 (ro) | 2017-07-28 | 2024-02-29 | Yuhan Corp | Procedeu de obținere a N-(5-((4-(4-((dimetilamino)metil)-3-fenil-1H-pirazol-1-il)pirimidin-2-il)amino)-4-metoxi-2-morfolinofenil)acrilamidei prin prin reacţia aminei corespunzătoare cu clorură de 3-halo-propionil |
| WO2019178129A1 (en) | 2018-03-13 | 2019-09-19 | Shire Human Genetic Therapies, Inc. | Substituted imidazopyridines as inhibitors of plasma kallikrein and uses thereof |
| CN111410654B (zh) * | 2019-01-19 | 2022-05-17 | 江苏新元素医药科技有限公司 | 3-溴-5-(2-乙基咪唑并[1,2-a]吡啶-3-羰基)-2-羟基苯甲腈的合成 |
| TWI841671B (zh) | 2019-01-24 | 2024-05-11 | 日商第一三共股份有限公司 | 具有取代基之脲化合物 |
| TWI759829B (zh) | 2019-08-23 | 2022-04-01 | 財團法人生物技術開發中心 | 作為第iii型受體酪胺酸激酶抑制劑之雜環吡唑衍生物 |
| PT4031547T (pt) | 2019-09-18 | 2024-08-27 | Takeda Pharmaceuticals Co | Inibidores de calicreína plasmática e utilizações dos mesmos |
| WO2021055589A1 (en) | 2019-09-18 | 2021-03-25 | Shire Human Genetic Therapies, Inc. | Heteroaryl plasma kallikrein inhibitors |
| WO2025146196A1 (zh) * | 2024-01-04 | 2025-07-10 | 上海翰森生物医药科技有限公司 | 多环类衍生物抑制剂、其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| IL165262A0 (en) | 2002-05-23 | 2005-12-18 | Cytopia Pty Ltd | Kinase inhibitors |
| CA2672213C (en) * | 2006-12-22 | 2016-02-16 | Astex Therapeutics Limited | Bicyclic amine derivatives as protein tyrosine kinase inhibitors |
| JP5374492B2 (ja) * | 2007-04-03 | 2013-12-25 | アレイ バイオファーマ、インコーポレイテッド | 受容体チロシンキナーゼ阻害薬としてのイミダゾ［１，２−ａ］ピリジン化合物 |
| FR2925901B1 (fr) | 2008-01-02 | 2011-03-04 | Sanofi Aventis | DERIVES DE N-HETEROCYCLIQUE-IMIDAZO°1,2-a!PYRIDINE-2- CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| ES2526966T3 (es) * | 2008-06-05 | 2015-01-19 | Glaxo Group Limited | Compuestos novedosos |
| TW201105669A (en) * | 2009-07-30 | 2011-02-16 | Irm Llc | Compounds and compositions as Syk kinase inhibitors |
| KR101779630B1 (ko) | 2009-12-21 | 2017-09-18 | 어레이 바이오파마 인크. | ｃＦＭＳ 억제제로서 치환된 Ｎ-（１Ｈ-인다졸-４-일）이미다조［１,２-ａ］피리딘-３-카복사미드 화합물 |
| JO3337B1 (ar) | 2010-12-13 | 2019-03-13 | Debiopharm Sa | تركيبات صيدلية تشمل أليسبوريفير |
| UY33801A (es) | 2010-12-13 | 2013-06-28 | Array Biopharma Inc | COMPUESTOS SUSTITUIDOS DE N-(1H-INDAZOL-4IL)IMIDAZO[1,2-a]PIRIDIN-3-CARBOXAMIDA COMO INHIBIDORES DE LA TIROSINA QUINASA RECEPTORA DE TIPO III |
| CN102250246A (zh) * | 2011-06-10 | 2011-11-23 | 常州亚当生物技术有限公司 | 抗VEGF/PDGFRβ双特异性抗体及其应用 |
-
2011
- 2011-12-13 UY UY0001033801A patent/UY33801A/es not_active Application Discontinuation
- 2011-12-13 EP EP11808427.6A patent/EP2651939B1/en active Active
- 2011-12-13 NZ NZ61323511A patent/NZ613235A/en not_active IP Right Cessation
- 2011-12-13 MX MX2013006763A patent/MX2013006763A/es active IP Right Grant
- 2011-12-13 DK DK11808427.6T patent/DK2651939T3/en active
- 2011-12-13 SI SI201130508T patent/SI2651939T1/sl unknown
- 2011-12-13 SG SG2013045349A patent/SG191129A1/en unknown
- 2011-12-13 ME MEP-2015-98A patent/ME02172B/me unknown
- 2011-12-13 MY MYPI2013700991A patent/MY172110A/en unknown
- 2011-12-13 CA CA2821712A patent/CA2821712C/en not_active Expired - Fee Related
- 2011-12-13 CN CN201180067342.XA patent/CN103347882B/zh not_active Expired - Fee Related
- 2011-12-13 CA CA3027814A patent/CA3027814A1/en not_active Abandoned
- 2011-12-13 RS RS20150446A patent/RS54070B1/sr unknown
- 2011-12-13 AU AU2011344001A patent/AU2011344001B2/en not_active Ceased
- 2011-12-13 HR HRP20150571TT patent/HRP20150571T1/hr unknown
- 2011-12-13 RU RU2013132758/04A patent/RU2591195C2/ru active
- 2011-12-13 BR BR112013014854-3A patent/BR112013014854B1/pt not_active IP Right Cessation
- 2011-12-13 US US13/994,048 patent/US9174981B2/en not_active Expired - Fee Related
- 2011-12-13 TW TW100146108A patent/TWI527813B/zh not_active IP Right Cessation
- 2011-12-13 CN CN201811311712.XA patent/CN109608449A/zh active Pending
- 2011-12-13 ES ES11808427.6T patent/ES2540996T3/es active Active
- 2011-12-13 CN CN201610248287.9A patent/CN105924437B/zh not_active Expired - Fee Related
- 2011-12-13 PL PL11808427T patent/PL2651939T3/pl unknown
- 2011-12-13 HU HUE11808427A patent/HUE025416T2/en unknown
- 2011-12-13 PT PT118084276T patent/PT2651939E/pt unknown
- 2011-12-13 WO PCT/US2011/064549 patent/WO2012082689A1/en not_active Ceased
- 2011-12-13 KR KR1020137018492A patent/KR101974665B1/ko not_active Expired - Fee Related
- 2011-12-13 UA UAA201308896A patent/UA112425C2/uk unknown
- 2011-12-13 PH PH1/2013/501221A patent/PH12013501221A1/en unknown
- 2011-12-13 JP JP2013544674A patent/JP5868996B2/ja not_active Expired - Fee Related
-
2013
- 2013-06-13 CL CL2013001712A patent/CL2013001712A1/es unknown
- 2013-06-13 IL IL226911A patent/IL226911A/en active IP Right Grant
- 2013-07-15 CR CR20130349A patent/CR20130349A/es unknown
- 2013-07-15 CO CO13167580A patent/CO6751248A2/es active IP Right Grant
-
2015
- 2015-07-08 SM SM201500165T patent/SMT201500165B/xx unknown
- 2015-09-18 US US14/858,029 patent/US9809590B2/en not_active Expired - Fee Related
- 2015-10-19 JP JP2015205806A patent/JP2016040303A/ja not_active Withdrawn
-
2016
- 2016-09-02 AU AU2016222468A patent/AU2016222468B2/en not_active Ceased
-
2017
- 2017-09-27 US US15/717,700 patent/US10669269B2/en not_active Expired - Fee Related
- 2017-11-27 JP JP2017227134A patent/JP2018065835A/ja not_active Withdrawn
-
2018
- 2018-03-16 AU AU2018201903A patent/AU2018201903B2/en not_active Ceased
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