JP2015518890A5 - - Google Patents
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- Publication number
- JP2015518890A5 JP2015518890A5 JP2015516121A JP2015516121A JP2015518890A5 JP 2015518890 A5 JP2015518890 A5 JP 2015518890A5 JP 2015516121 A JP2015516121 A JP 2015516121A JP 2015516121 A JP2015516121 A JP 2015516121A JP 2015518890 A5 JP2015518890 A5 JP 2015518890A5
- Authority
- JP
- Japan
- Prior art keywords
- crystalline form
- xrpd
- ray powder
- powder diffraction
- pattern
- 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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- 238000000634 powder X-ray diffraction Methods 0.000 claims description 136
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 44
- 238000002411 thermogravimetry Methods 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- -1 6-Cyano-5-trifluoromethylpyridin-3-yl Chemical group 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 238000001757 thermogravimetry curve Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 206010060862 Prostate cancer Diseases 0.000 claims description 9
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 7
- HJBWBFZLDZWPHF-UHFFFAOYSA-N apalutamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1N1C2(CCC2)C(=O)N(C=2C=C(C(C#N)=NC=2)C(F)(F)F)C1=S HJBWBFZLDZWPHF-UHFFFAOYSA-N 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940088597 hormone Drugs 0.000 claims description 3
- 239000005556 hormone Substances 0.000 claims description 3
- 208000018821 hormone-resistant prostate carcinoma Diseases 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 239000006186 oral dosage form Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- NAGFMACWWJYORB-UHFFFAOYSA-N 2-fluoro-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1F NAGFMACWWJYORB-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261656888P | 2012-06-07 | 2012-06-07 | |
| US61/656,888 | 2012-06-07 | ||
| PCT/US2013/044116 WO2013184681A1 (en) | 2012-06-07 | 2013-06-04 | Crystalline forms of an androgen receptor modulator |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017025746A Division JP6345821B2 (ja) | 2012-06-07 | 2017-02-15 | アンドロゲン受容体変調剤の結晶質形態 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015518890A JP2015518890A (ja) | 2015-07-06 |
| JP2015518890A5 true JP2015518890A5 (enExample) | 2016-06-02 |
| JP6182209B2 JP6182209B2 (ja) | 2017-08-16 |
Family
ID=49712550
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015516121A Active JP6182209B2 (ja) | 2012-06-07 | 2013-06-04 | アンドロゲン受容体変調剤の結晶質形態 |
| JP2017025746A Active JP6345821B2 (ja) | 2012-06-07 | 2017-02-15 | アンドロゲン受容体変調剤の結晶質形態 |
| JP2018098638A Pending JP2018141009A (ja) | 2012-06-07 | 2018-05-23 | アンドロゲン受容体変調剤の結晶質形態 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017025746A Active JP6345821B2 (ja) | 2012-06-07 | 2017-02-15 | アンドロゲン受容体変調剤の結晶質形態 |
| JP2018098638A Pending JP2018141009A (ja) | 2012-06-07 | 2018-05-23 | アンドロゲン受容体変調剤の結晶質形態 |
Country Status (45)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008119015A2 (en) | 2007-03-27 | 2008-10-02 | Sloan-Kettering Institute For Cancer Research | Synthesis of thiohydantoins |
| PE20150099A1 (es) | 2011-12-16 | 2015-01-30 | Olema Pharmaceuticals Inc | Compuestos novedosos de benzopirano, composiciones y usos de los mismos |
| ES2809738T3 (es) | 2012-06-07 | 2021-03-05 | Aragon Pharmaceuticals Inc | Formas cristalinas de un modulador de receptor de andrógenos |
| WO2014043208A1 (en) | 2012-09-11 | 2014-03-20 | Medivation Prostate Therapeutics, Inc. | Formulations of enzalutamide |
| PT3305285T (pt) | 2012-09-26 | 2020-11-24 | Aragon Pharmaceuticals Inc | Antiandrogénios para o tratamento de cancro da próstata resistente à castração não metastático |
| JOP20200097A1 (ar) | 2013-01-15 | 2017-06-16 | Aragon Pharmaceuticals Inc | معدل مستقبل أندروجين واستخداماته |
| CN106795152B (zh) * | 2014-08-26 | 2020-01-31 | 安斯达尔生物技术有限责任公司 | 蛋白激酶抑制剂 |
| CR20170217A (es) | 2014-12-05 | 2017-08-30 | Aragon Pharmaceuticals Inc | Composiciones anticancerígenas |
| CA2969675C (en) | 2014-12-05 | 2023-06-06 | Aragon Pharmaceuticals, Inc. | Anticancer compositions |
| BR112017011788A2 (pt) | 2014-12-05 | 2017-12-26 | Aragon Pharmaceuticals Inc | composições anticâncer |
| WO2016100905A1 (en) | 2014-12-19 | 2016-06-23 | Lutron Electronics Co., Inc. | Multi-channel lighting fixture having multiple light-emitting diode drivers |
| TW201808287A (zh) | 2016-06-03 | 2018-03-16 | 美商艾瑞岡醫藥公司 | 抗癌組成物 |
| ES2952770T3 (es) | 2016-12-13 | 2023-11-06 | Watson Lab Inc | Formas de estado sólido de apalutamida |
| EP4438126A3 (en) | 2017-10-16 | 2025-01-01 | Aragon Pharmaceuticals, Inc. | Anti-androgens for the treatment of non-metastatic castration-resistant prostate cancer |
| WO2019135254A1 (en) | 2018-01-02 | 2019-07-11 | Mylan Laboratories Limited | Apalutamide polymorphs and their preparation thereof |
| WO2019242439A1 (zh) * | 2018-06-20 | 2019-12-26 | 苏州科睿思制药有限公司 | Arn-509的晶型及其制备方法和用途 |
| WO2020049598A2 (en) | 2018-09-08 | 2020-03-12 | Cipla Limited | Apalutamide polymorphs |
| IT201900003839A1 (it) | 2019-03-15 | 2020-09-15 | Olon Spa | Sintesi di apalutamide amorfa stabile |
| WO2020234817A1 (en) * | 2019-05-21 | 2020-11-26 | Laurus Labs Limited | Polymorphic forms of apalutamide and its preparation thereof |
| IT201900010593A1 (it) | 2019-07-01 | 2021-01-01 | Dipharma Francis Srl | Forma cristallina di un inibitore di recettori degli androgeni |
| EP4017848A1 (en) * | 2019-08-22 | 2022-06-29 | Dr. Reddy's Laboratories Ltd. | Process for the preparation of apalutamide |
| IT201900015974A1 (it) | 2019-09-10 | 2021-03-10 | Olon Spa | Apalutamide cristallina stabile in forma pura e processo per la sua preparazione |
| CN110590740A (zh) * | 2019-09-20 | 2019-12-20 | 武汉大学 | 一种阿帕鲁胺化合物及其药物制剂 |
| WO2022049265A1 (en) | 2020-09-04 | 2022-03-10 | Synthon B.V. | Improved process for preparation of apalutamide |
| CN112679468A (zh) * | 2021-01-05 | 2021-04-20 | 四川科伦药物研究院有限公司 | 阿帕他胺的晶体形式、制备方法和用途 |
| WO2023143090A1 (zh) * | 2022-01-25 | 2023-08-03 | 成都苑东生物制药股份有限公司 | 一种阿帕他胺溶剂化物新晶型及其制备方法 |
| CN115536634B (zh) * | 2022-10-17 | 2024-06-11 | 上海博悦生物科技有限公司 | 一种阿帕他胺的合成方法 |
| CN116332907A (zh) * | 2023-03-16 | 2023-06-27 | 奥锐特药业股份有限公司 | 一种无定形阿帕他胺的制备方法 |
| WO2025153768A1 (en) * | 2024-01-18 | 2025-07-24 | Nanoform Finland Oyj | Composition comprising crystalline nanosized apalutamide |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5323907A (en) | 1992-06-23 | 1994-06-28 | Multi-Comp, Inc. | Child resistant package assembly for dispensing pharmaceutical medications |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| CN101032483B (zh) * | 2006-03-09 | 2011-05-04 | 陈德桂 | 调节雄激素受体活性的乙内酰脲衍生物及其应用 |
| PL3412290T3 (pl) | 2006-03-27 | 2021-09-06 | The Regents Of The University Of California | Modulator receptora androgenowego do leczenia raka gruczołu krokowego i chorób związanych z receptorem androgenowym |
| CA2648139A1 (en) * | 2006-03-29 | 2007-11-08 | The Regents Of The University Of California | Diaryl thiohydantoin compounds and their use in the treatment of hyperproliferative disorders |
| WO2008119015A2 (en) * | 2007-03-27 | 2008-10-02 | Sloan-Kettering Institute For Cancer Research | Synthesis of thiohydantoins |
| EA028869B1 (ru) | 2010-02-16 | 2018-01-31 | Арагон Фармасьютикалс, Инк. | Модуляторы рецептора андрогенов и их применение |
| ES2809738T3 (es) | 2012-06-07 | 2021-03-05 | Aragon Pharmaceuticals Inc | Formas cristalinas de un modulador de receptor de andrógenos |
| WO2019242439A1 (zh) | 2018-06-20 | 2019-12-26 | 苏州科睿思制药有限公司 | Arn-509的晶型及其制备方法和用途 |
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2013
- 2013-06-04 ES ES18157435T patent/ES2809738T3/es active Active
- 2013-06-04 TW TW102119817A patent/TWI532732B/zh active
- 2013-06-04 CA CA3114726A patent/CA3114726A1/en active Pending
- 2013-06-04 CA CA2875767A patent/CA2875767C/en active Active
- 2013-06-04 ME MEP-2020-163A patent/ME03815B/me unknown
- 2013-06-04 CN CN202110417935.XA patent/CN113135892A/zh active Pending
- 2013-06-04 US US14/406,520 patent/US9481663B2/en active Active
- 2013-06-04 RS RS20210739A patent/RS61988B1/sr unknown
- 2013-06-04 SM SM20180311T patent/SMT201800311T1/it unknown
- 2013-06-04 DK DK18157435.1T patent/DK3348553T3/da active
- 2013-06-04 SG SG10201610249TA patent/SG10201610249TA/en unknown
- 2013-06-04 SI SI201331894T patent/SI3533792T1/sl unknown
- 2013-06-04 LT LTEP19169275.5T patent/LT3533792T/lt unknown
- 2013-06-04 HR HRP20180902TT patent/HRP20180902T1/hr unknown
- 2013-06-04 SI SI201331788T patent/SI3348553T1/sl unknown
- 2013-06-04 CN CN201610202980.2A patent/CN105693692A/zh active Pending
- 2013-06-04 PE PE2019002096A patent/PE20200725A1/es unknown
- 2013-06-04 IL IL320522A patent/IL320522A/en unknown
- 2013-06-04 PL PL13800681T patent/PL2858985T3/pl unknown
- 2013-06-04 CR CR20190331A patent/CR20190331A/es unknown
- 2013-06-04 CN CN201380041652.3A patent/CN104619692A/zh active Pending
- 2013-06-04 EP EP18157435.1A patent/EP3348553B1/en not_active Revoked
- 2013-06-04 HU HUE13800681A patent/HUE038082T2/hu unknown
- 2013-06-04 PL PL19169275T patent/PL3533792T3/pl unknown
- 2013-06-04 SG SG11201408140QA patent/SG11201408140QA/en unknown
- 2013-06-04 WO PCT/US2013/044116 patent/WO2013184681A1/en not_active Ceased
- 2013-06-04 IL IL267608A patent/IL267608B2/en unknown
- 2013-06-04 PT PT138006812T patent/PT2858985T/pt unknown
- 2013-06-04 EP EP21171579.2A patent/EP3922629A1/en active Pending
- 2013-06-04 LT LTEP18157435.1T patent/LT3348553T/lt unknown
- 2013-06-04 HK HK15111086.5A patent/HK1210175A1/xx unknown
- 2013-06-04 AU AU2013271751A patent/AU2013271751B2/en active Active
- 2013-06-04 ES ES13800681.2T patent/ES2670683T3/es active Active
- 2013-06-04 IN IN10084DEN2014 patent/IN2014DN10084A/en unknown
- 2013-06-04 MX MX2014015005A patent/MX356754B/es active IP Right Grant
- 2013-06-04 LT LTEP13800681.2T patent/LT2858985T/lt unknown
- 2013-06-04 ES ES19169275T patent/ES2875932T3/es active Active
- 2013-06-04 SM SM20200496T patent/SMT202000496T1/it unknown
- 2013-06-04 SM SM20210355T patent/SMT202100355T1/it unknown
- 2013-06-04 EP EP19169275.5A patent/EP3533792B1/en active Active
- 2013-06-04 SG SG10201610248SA patent/SG10201610248SA/en unknown
- 2013-06-04 HU HUE19169275A patent/HUE054595T2/hu unknown
- 2013-06-04 DK DK19169275.5T patent/DK3533792T3/da active
- 2013-06-04 PT PT181574351T patent/PT3348553T/pt unknown
- 2013-06-04 PL PL18157435T patent/PL3348553T3/pl unknown
- 2013-06-04 EA EA201492272A patent/EA028791B1/ru unknown
- 2013-06-04 EA EA201992010A patent/EA201992010A1/ru unknown
- 2013-06-04 RS RS20200913A patent/RS60617B1/sr unknown
- 2013-06-04 JP JP2015516121A patent/JP6182209B2/ja active Active
- 2013-06-04 PE PE2014002383A patent/PE20150631A1/es active IP Right Grant
- 2013-06-04 PE PE2020000234A patent/PE20200795A1/es unknown
- 2013-06-04 UA UAA201500086A patent/UA115665C2/uk unknown
- 2013-06-04 KR KR1020157000266A patent/KR102062024B1/ko active Active
- 2013-06-04 PT PT191692755T patent/PT3533792T/pt unknown
- 2013-06-04 RS RS20180680A patent/RS57370B1/sr unknown
- 2013-06-04 HU HUE18157435A patent/HUE050357T2/hu unknown
- 2013-06-04 CA CA3008345A patent/CA3008345C/en active Active
- 2013-06-04 TR TR2018/08939T patent/TR201808939T4/tr unknown
- 2013-06-04 SI SI201331010T patent/SI2858985T1/sl unknown
- 2013-06-04 KR KR1020197033592A patent/KR102195916B1/ko active Active
- 2013-06-04 NZ NZ702203A patent/NZ702203A/en unknown
- 2013-06-04 UA UAA201702779A patent/UA123142C2/uk unknown
- 2013-06-04 DK DK13800681.2T patent/DK2858985T3/en active
- 2013-06-04 EA EA201791592A patent/EA033956B1/ru unknown
- 2013-06-04 EP EP13800681.2A patent/EP2858985B1/en active Active
- 2013-06-04 ME MEP-2018-158A patent/ME03081B/me unknown
- 2013-06-04 CA CA3055660A patent/CA3055660A1/en not_active Abandoned
- 2013-06-04 BR BR112014030678A patent/BR112014030678A2/pt not_active Application Discontinuation
- 2013-06-04 NZ NZ717683A patent/NZ717683A/en unknown
- 2013-06-04 MY MYPI2014703627A patent/MY187500A/en unknown
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2014
- 2014-12-01 CR CR20140549A patent/CR20140549A/es unknown
- 2014-12-04 IL IL236055A patent/IL236055A0/en unknown
- 2014-12-04 NI NI201400142A patent/NI201400142A/es unknown
- 2014-12-04 PH PH12014502714A patent/PH12014502714B1/en unknown
- 2014-12-05 EC ECIEPI201430098A patent/ECSP14030098A/es unknown
- 2014-12-05 CL CL2014003331A patent/CL2014003331A1/es unknown
- 2014-12-05 GT GT201400283A patent/GT201400283A/es unknown
- 2014-12-09 CO CO14270612A patent/CO7240407A2/es unknown
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2015
- 2015-01-06 ZA ZA2015/00076A patent/ZA201500076B/en unknown
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2016
- 2016-07-26 PH PH12016501470A patent/PH12016501470B1/en unknown
- 2016-09-12 US US15/262,522 patent/US9994545B2/en active Active
- 2016-12-19 HK HK16114389.2A patent/HK1226066A1/zh unknown
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2017
- 2017-01-17 AU AU2017200298A patent/AU2017200298B2/en active Active
- 2017-02-15 JP JP2017025746A patent/JP6345821B2/ja active Active
- 2017-12-22 AU AU2017279807A patent/AU2017279807B2/en active Active
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2018
- 2018-05-09 US US15/975,449 patent/US10308630B2/en active Active
- 2018-05-23 JP JP2018098638A patent/JP2018141009A/ja active Pending
- 2018-05-31 IL IL259738A patent/IL259738B/en active IP Right Grant
- 2018-07-06 CY CY20181100712T patent/CY1120393T1/el unknown
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2019
- 2019-04-15 US US16/384,002 patent/US10526310B2/en active Active
- 2019-07-10 US US16/507,780 patent/US10556882B2/en active Active
- 2019-12-11 US US16/710,785 patent/US10766875B2/en active Active
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2020
- 2020-06-15 IL IL275413A patent/IL275413A/en unknown
- 2020-07-29 US US16/942,069 patent/US10934271B2/en active Active
- 2020-08-31 HR HRP20201387TT patent/HRP20201387T1/hr unknown
- 2020-09-23 CY CY20201100901T patent/CY1123427T1/el unknown
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2021
- 2021-01-26 US US17/158,806 patent/US12018008B2/en active Active
- 2021-06-08 HR HRP20210909TT patent/HRP20210909T1/hr unknown
- 2021-07-02 CY CY20211100595T patent/CY1124831T1/el unknown
- 2021-11-02 NO NO2021046C patent/NO2021046I1/no unknown
- 2021-11-02 LU LU00236C patent/LUC00236I2/fr unknown
- 2021-11-03 FR FR21C1050C patent/FR21C1050I2/fr active Active
- 2021-11-03 LT LTPA2021525C patent/LTC3533792I2/lt unknown
- 2021-11-03 NL NL301144C patent/NL301144I2/nl unknown
- 2021-11-04 HU HUS2100047C patent/HUS2100047I1/hu unknown
- 2021-11-04 CY CY2021032C patent/CY2021032I2/el unknown
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2024
- 2024-05-13 US US18/662,345 patent/US20250092011A1/en not_active Abandoned
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