SG11201811506UA - Process of preparing a peptide epoxyketone immunoproteasome inhibitor, and precursors thereof - Google Patents
Process of preparing a peptide epoxyketone immunoproteasome inhibitor, and precursors thereofInfo
- Publication number
- SG11201811506UA SG11201811506UA SG11201811506UA SG11201811506UA SG11201811506UA SG 11201811506U A SG11201811506U A SG 11201811506UA SG 11201811506U A SG11201811506U A SG 11201811506UA SG 11201811506U A SG11201811506U A SG 11201811506UA SG 11201811506U A SG11201811506U A SG 11201811506UA
- Authority
- SG
- Singapore
- Prior art keywords
- international
- preparing
- pct
- precursors
- english
- Prior art date
Links
- 229940126097 immunoproteasome inhibitor Drugs 0.000 title abstract 2
- 239000002243 precursor Substances 0.000 title abstract 2
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- BYPRQOWKWXRIBW-GKAPJAKFSA-N 2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound N1(CCOCC1)CC(=O)N[C@H](C(=O)NC(C(=O)N)C)C BYPRQOWKWXRIBW-GKAPJAKFSA-N 0.000 abstract 1
- 235000001543 Corylus americana Nutrition 0.000 abstract 1
- 240000007582 Corylus avellana Species 0.000 abstract 1
- 235000007466 Corylus avellana Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008520 organization Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/46—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by amide or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property 111111101111 0 1110101011111 011101 0 011111111111111H1111111011111111111110111111 Organization International Bureau (10) International Publication Number (43) International Publication Date .....0\"\"\" WO 2018/005781 Al 04 January 2018 (04.01.2018) W I PO I PCT (51) International Patent Classification: C07D 295/15 (2006.01) C07D 303/46 (2006.01) Published: C07D 303/12 (2006.01) CO7C 69/612 (2006.01) — with international search report (Art. 21(3)) — before the expiration of the time limit for amending the (21) International Application Number: claims and to be republished in the event of receipt of PCT/US2017/039975 amendments (Rule 48.2(h)) (22) International Filing Date: 29 June 2017 (29.06.2017) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 62/356,178 29 June 2016 (29.06.2016) US (71) Applicant: KEZAR LIFE SCIENCES [US/US]; 300 Utah Ave, Suite 105, South San Francisco, CA 94080 (US). (72) Inventors: JOHNSON, Henry; 360 Hazel Avenue, San Bruno, CA 94066 (US). DALZIEL, Sean; 1220 Balboa Avenue, Burlington, CA 94010 (US). MCMINN, Dustin; 255 Kent Road, Pacifica, CA 94044 (US). (74) Agent: BERKOWSKI, Kimberly L. et al.; Marshall, Ger- = stein & Borun Llp, 233 S. Wacker Drive, 6300 Willis Tow- er, Chicago, IL 60606-6357 (US). = (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, = CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, _ DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. = = = = = _ Designated States (unless otherwise indicated, for every — (84) _ _ kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). = = = = — = 1-1 (54) Title: PROCESS OF PREPARING A PEPTIDE EPDXYKETONE IMMUNOPROTEASOME INHIBITOR, AND PRE- I l CURSORS THEREOF GC IN (57) : Disclosed herein are methods for preparing kr) il [(2S,3R)-N-[(25)-3-(cyclopent- 1-en-l-y1)-1-[(2R)-2-methyloxi- 0 - ' - '\"i 0 ran-2-yl] -1 -oxopropan-2-y1]-3-hydroxy-3-(4-methoxypheny1)-2- H --.... 1-1 IL)-L N ,,, N (G) [(2S)-2-[2-(morpholin-4-yl)acetamido]propanamido]propanamide H (compound \"G\"): and precursors thereof. 0 0 ei AMIlk HO so OM e
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662356178P | 2016-06-29 | 2016-06-29 | |
| PCT/US2017/039975 WO2018005781A1 (en) | 2016-06-29 | 2017-06-29 | Process of preparing a peptide epoxyketone immunoproteasome inhibitor, and precursors thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG11201811506UA true SG11201811506UA (en) | 2019-01-30 |
Family
ID=59351085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG11201811506UA SG11201811506UA (en) | 2016-06-29 | 2017-06-29 | Process of preparing a peptide epoxyketone immunoproteasome inhibitor, and precursors thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US10781192B2 (en) |
| EP (2) | EP4296257A3 (en) |
| JP (2) | JP7065044B2 (en) |
| KR (2) | KR102524751B1 (en) |
| CN (1) | CN109641860B (en) |
| AR (1) | AR108919A1 (en) |
| AU (1) | AU2017290147B2 (en) |
| BR (1) | BR112018077250A2 (en) |
| CA (1) | CA3029418A1 (en) |
| CL (1) | CL2018003873A1 (en) |
| CO (1) | CO2019000866A2 (en) |
| EA (1) | EA201990157A1 (en) |
| IL (2) | IL263771B2 (en) |
| MX (1) | MX2018016386A (en) |
| SG (1) | SG11201811506UA (en) |
| TW (1) | TWI751177B (en) |
| WO (1) | WO2018005781A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL263771B2 (en) * | 2016-06-29 | 2023-09-01 | Kezar Life Sciences | Process of preparing a peptide epoxyketone immunoproteasome inhibitor, and precursors thereof |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| US5340736A (en) | 1991-05-13 | 1994-08-23 | The President & Fellows Of Harvard College | ATP-dependent protease and use of inhibitors for same in the treatment of cachexia and muscle wasting |
| AU4499697A (en) | 1996-09-13 | 1998-04-02 | New York University | Method for treating parasitic diseases with proteasome inhibitors |
| WO2004043374A2 (en) | 2002-11-06 | 2004-05-27 | Dana-Farber Cancer Institute, Inc. | Methods and compositions for treating cancer using proteasome inhibitors |
| US7687456B2 (en) | 2005-11-09 | 2010-03-30 | Proteolix, Inc. | Compounds for enzyme inhibition |
| NZ597545A (en) | 2006-06-19 | 2013-07-26 | Proteolix Inc | Peptide epoxyketones for proteasome inhibition |
| US7442830B1 (en) | 2007-08-06 | 2008-10-28 | Millenium Pharmaceuticals, Inc. | Proteasome inhibitors |
| EP2207791B2 (en) | 2007-10-04 | 2019-08-07 | Onyx Therapeutics, Inc. | Crystalline peptide epoxy ketone protease inhibitors and the synthesis of amino acid keto-epoxides |
| CN101525370A (en) | 2008-03-06 | 2009-09-09 | 海南建邦制药科技有限公司 | Novel efficient condensing agent for synthesizing polypeptide |
| MX368109B (en) | 2008-10-21 | 2019-09-18 | Onyx Therapeutics Inc | Combination therapy with peptide epoxyketones. |
| TWI504598B (en) | 2009-03-20 | 2015-10-21 | Onyx Therapeutics Inc | Crystalline tripeptide epoxy ketone protease inhibitors |
| US8853147B2 (en) | 2009-11-13 | 2014-10-07 | Onyx Therapeutics, Inc. | Use of peptide epoxyketones for metastasis suppression |
| US8697646B2 (en) | 2010-04-07 | 2014-04-15 | Onyx Therapeutics, Inc. | Crystalline peptide epoxyketone immunoproteasome inhibitor |
| US8609610B2 (en) | 2011-02-18 | 2013-12-17 | Trustees Of Dartmouth College | Inhibitors of the trypsin-like site of the proteasome and methods of use thereof |
| EP2705027B1 (en) | 2011-05-02 | 2015-06-03 | Gilead Sciences, Inc. | Amorphous solid salts of Cobicistat (GS-9350) |
| KR20220088949A (en) | 2012-05-08 | 2022-06-28 | 오닉스 세라퓨틱스, 인크. | Cyclodextrin complexation methods for formulating peptide proteasome inhibitors |
| EP2867202B1 (en) | 2012-06-29 | 2017-08-09 | Nissan Chemical Industries, Ltd. | Method for producing stereoselective epoxyketone compound |
| JP2016501831A (en) | 2012-10-11 | 2016-01-21 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ketoamide immunoproteasome inhibitor |
| RU2015117581A (en) | 2012-10-12 | 2016-12-10 | Ф. Хоффманн-Ля Рош Аг | MACROCYCLIC KETOAMIDE INHIBITORS IMMUNOPROTEASOM |
| TW201422255A (en) * | 2012-10-24 | 2014-06-16 | Onyx Therapeutics Inc | Modified release formulations for oprozomib |
| AR095426A1 (en) * | 2013-03-14 | 2015-10-14 | Onyx Therapeutics Inc | TRIPEPTIDE INHIBITORS OF PROTEASA EPOXYCETONE |
| KR102365509B1 (en) * | 2013-03-14 | 2022-02-21 | 오닉스 세라퓨틱스, 인크. | Tripeptide epoxy ketone protease inhibitors |
| TWI662047B (en) | 2013-03-14 | 2019-06-11 | 歐尼克斯治療公司 | Tripeptide epoxy ketone protease inhibitors |
| CN104710507B (en) | 2013-12-11 | 2018-08-14 | 深圳翰宇药业股份有限公司 | A kind of preparation method of Carfilzomib |
| CN104230857A (en) | 2014-08-19 | 2014-12-24 | 上海皓元生物医药科技有限公司 | Preparation method of intermediate compounds of carfilzomib and intermediate compounds |
| IL263771B2 (en) * | 2016-06-29 | 2023-09-01 | Kezar Life Sciences | Process of preparing a peptide epoxyketone immunoproteasome inhibitor, and precursors thereof |
-
2017
- 2017-06-29 IL IL263771A patent/IL263771B2/en unknown
- 2017-06-29 AR ARP170101808A patent/AR108919A1/en unknown
- 2017-06-29 WO PCT/US2017/039975 patent/WO2018005781A1/en unknown
- 2017-06-29 BR BR112018077250-0A patent/BR112018077250A2/en unknown
- 2017-06-29 TW TW106121701A patent/TWI751177B/en active
- 2017-06-29 US US16/312,688 patent/US10781192B2/en active Active
- 2017-06-29 EA EA201990157A patent/EA201990157A1/en unknown
- 2017-06-29 EP EP23191555.4A patent/EP4296257A3/en active Pending
- 2017-06-29 AU AU2017290147A patent/AU2017290147B2/en active Active
- 2017-06-29 KR KR1020197002872A patent/KR102524751B1/en active IP Right Grant
- 2017-06-29 KR KR1020237013160A patent/KR102571568B1/en active IP Right Grant
- 2017-06-29 MX MX2018016386A patent/MX2018016386A/en unknown
- 2017-06-29 EP EP17740180.9A patent/EP3478669B1/en active Active
- 2017-06-29 JP JP2018568194A patent/JP7065044B2/en active Active
- 2017-06-29 SG SG11201811506UA patent/SG11201811506UA/en unknown
- 2017-06-29 IL IL302234A patent/IL302234A/en unknown
- 2017-06-29 CA CA3029418A patent/CA3029418A1/en active Pending
- 2017-06-29 CN CN201780053331.3A patent/CN109641860B/en active Active
-
2018
- 2018-12-28 CL CL2018003873A patent/CL2018003873A1/en unknown
-
2019
- 2019-01-29 CO CONC2019/0000866A patent/CO2019000866A2/en unknown
-
2020
- 2020-09-09 US US17/015,450 patent/US11498907B2/en active Active
-
2022
- 2022-04-25 JP JP2022071492A patent/JP7392031B2/en active Active
- 2022-10-13 US US17/965,064 patent/US11976053B2/en active Active
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