AR108919A1 - Proceso de preparación del inhibidor de inmunoproteasoma de péptido epoxicetona, y sus precursores - Google Patents
Proceso de preparación del inhibidor de inmunoproteasoma de péptido epoxicetona, y sus precursoresInfo
- Publication number
- AR108919A1 AR108919A1 ARP170101808A ARP170101808A AR108919A1 AR 108919 A1 AR108919 A1 AR 108919A1 AR P170101808 A ARP170101808 A AR P170101808A AR P170101808 A ARP170101808 A AR P170101808A AR 108919 A1 AR108919 A1 AR 108919A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- methyloxiran
- propanamido
- oxopropan
- Prior art date
Links
- 239000002243 precursor Substances 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 9
- ZCANDMMZIHRQCE-AFAVFJNCSA-N (2S,3R)-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanoic acid Chemical compound COc1ccc(cc1)[C@@H](O)[C@H](NC(=O)[C@H](C)NC(=O)CN1CCOCC1)C(O)=O ZCANDMMZIHRQCE-AFAVFJNCSA-N 0.000 abstract 2
- 229910002483 Cu Ka Inorganic materials 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000000634 powder X-ray diffraction Methods 0.000 abstract 2
- 230000005855 radiation Effects 0.000 abstract 2
- ZJMQURXHSNGKDX-GXSJLCMTSA-N (2S)-2-amino-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]propan-1-one Chemical class C[C@@]1(CO1)C(=O)[C@@H](N)CC1=CCCC1 ZJMQURXHSNGKDX-GXSJLCMTSA-N 0.000 abstract 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 abstract 1
- -1 1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-aminium Chemical compound 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- 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
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- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (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
En la presente se describen métodos para preparar [(2S,3R)-N-[(2S)-3-(ciclopent-1-en-1-il)-1-[(2R)-2-metiloxiran-2-il]-1-oxopropan-2-il]-3-hidroxi-3-(4-metoxifenil)-2-[(2S)-2-[2-(morfolin-4-il)acetamido]propanamido]propanamida (compuesto G) de fórmula (1) y sus precursores (compuesto E y compuesto F) de fórmula (2) y (3) respectivamente. Reivindicación 1: Un método de preparación de (2S,3R)-N-[(2S)-3-(ciclopent-1-en-1-il)-1-[(2R)-2-metiloxiran-2-il]-1-oxopropan-2-il]-3-hidroxi-3-(4-metoxifenil)-2-[(2S)-2-[2-(morfolin-4-il)acetamido]propanamido]propanamida (compuesto G) de fórmula (1) que comprende: (a) mezclar una base de amina terciaria y una suspensión de: (i) ácido (2S,3R)-3-hidroxi-3-(4-metoxifenil)-2-((S)-2-(2-morfolino-acetamido)propanamido)propanoico (compuesto E) de fórmula (2), y (ii) sal (S)-3-(ciclopent-1-en-1-il)-1-((R)-2-metiloxiran-2-il)-1-oxopropan-2-aminio (compuesto F) de fórmula (3), donde X⁻ es un contraión; en un solvente aprótico para formar una mezcla y (b) mezclar un agente de acoplamiento y la mezcla de la etapa (a) para formar el compuesto G de fórmula (1); donde la temperatura de cada etapa de mezclado se mantiene a -20ºC a 25ºC. Reivindicación 69: Una forma cristalina de ácido (2S,3R)-3-hidroxi-3-(4-metoxifenil)-2-((S)-2-(2-morfolinoacetamido)propanamido)propanoico (compuesto E) de fórmula (2) caracterizada por un patrón de difracción de rayos X de polvo que comprende picos en 6,2, 8,5, 9,7, 12,7, 13,7, 16,0, 16,9, 17,2, 18,4, 18,9, 19,2, 19,7, 22,5, 24,7, 25,4, 28,7, y 29,7 ± 0,2º 2q usando radiación Cu Ka. Reivindicación 70: Una forma cristalina de sal (S)-3-(ciclopent-1-en-1-il)-1-((R)-2-metiloxiran-2-il)-1-oxopropan-2-aminio (compuesto F) de fórmula (3) donde X⁻ es tosilato, caracterizada por un patrón de difracción de rayos X de polvo que comprende picos en 6,8, 7,1, 7,4, 20,3, 23,0, 23,6, 24,5, 29,3, y 31,2 ± 0,2º 2q usando radiación Cu Ka.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662356178P | 2016-06-29 | 2016-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR108919A1 true AR108919A1 (es) | 2018-10-10 |
Family
ID=59351085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP170101808A AR108919A1 (es) | 2016-06-29 | 2017-06-29 | Proceso de preparación del inhibidor de inmunoproteasoma de péptido epoxicetona, y sus precursores |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US10781192B2 (es) |
| EP (2) | EP3478669B1 (es) |
| JP (2) | JP7065044B2 (es) |
| KR (2) | KR102524751B1 (es) |
| CN (2) | CN109641860B (es) |
| AR (1) | AR108919A1 (es) |
| AU (1) | AU2017290147B2 (es) |
| BR (1) | BR112018077250A2 (es) |
| CA (1) | CA3029418A1 (es) |
| CL (1) | CL2018003873A1 (es) |
| CO (1) | CO2019000866A2 (es) |
| EA (1) | EA201990157A1 (es) |
| IL (2) | IL302234A (es) |
| MX (1) | MX2018016386A (es) |
| SG (1) | SG11201811506UA (es) |
| TW (1) | TWI751177B (es) |
| WO (1) | WO2018005781A1 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102524751B1 (ko) * | 2016-06-29 | 2023-04-21 | 케자르 라이프 사이언스 | 펩티드 에폭시케톤 면역프로테아제 저해제 및 그 전구체의 제조 방법 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| WO1998010779A1 (en) | 1996-09-13 | 1998-03-19 | New York University | Method for treating parasitic diseases with proteasome inhibitors |
| CA2504933C (en) | 2002-11-06 | 2012-10-16 | Dana-Farber Cancer Institute, Inc. | Methods and compositions for treating cancer using proteasome inhibitors |
| AU2006311584B2 (en) | 2005-11-09 | 2012-03-08 | Onyx Therapeutics, Inc. | Compounds for enzyme inhibition |
| AU2007261345B2 (en) | 2006-06-19 | 2012-02-23 | Onyx Therapeutics, Inc. | Peptide epoxyketones for proteasome inhibition |
| US7442830B1 (en) | 2007-08-06 | 2008-10-28 | Millenium Pharmaceuticals, Inc. | Proteasome inhibitors |
| KR20170125413A (ko) | 2007-10-04 | 2017-11-14 | 오닉스 세라퓨틱스, 인크. | 결정형 펩티드 에폭시 케톤 프로테아제 저해제 및 아미노산 케토-에폭시드의 합성 |
| CN101525370A (zh) * | 2008-03-06 | 2009-09-09 | 海南建邦制药科技有限公司 | 一种新型高效多肽合成缩合剂 |
| CA2741312C (en) | 2008-10-21 | 2020-10-27 | Onyx Therapeutics, Inc. | Combination therapy with peptide epoxyketones |
| TWI504598B (zh) | 2009-03-20 | 2015-10-21 | Onyx Therapeutics Inc | 結晶性三肽環氧酮蛋白酶抑制劑 |
| JP5919196B2 (ja) | 2009-11-13 | 2016-05-18 | オニキス セラピューティクス， インク．Ｏｎｙｘ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | 転移抑制のためのペプチドエポキシケトンの使用 |
| MX2012011604A (es) | 2010-04-07 | 2013-02-27 | Onyx Therapeutics Inc | Inhibidor de inmunoproteasoma de péptido epoxicetona cristalino. |
| 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 |
| WO2012151165A1 (en) | 2011-05-02 | 2012-11-08 | Gilead Sciences, Inc. | Amorphous solid salts |
| KR20190137963A (ko) | 2012-05-08 | 2019-12-11 | 오닉스 세라퓨틱스, 인크. | 펩티드 프로테아좀 억제제 제제화를 위한 사이클로덱스트린 복합체화 방법 |
| JP6176259B2 (ja) | 2012-06-29 | 2017-08-09 | 日産化学工業株式会社 | 立体選択的なエポキシケトン化合物の製造方法 |
| BR112015008160A2 (pt) | 2012-10-11 | 2017-07-04 | Hoffmann La Roche | inibidores de imunoproteassoma de cetoamida |
| US20150266920A1 (en) | 2012-10-12 | 2015-09-24 | Hoff-Mann-La Roche Inc. | Macrocyclic ketoamide immunoproteasome inhibitors |
| TW201422255A (zh) * | 2012-10-24 | 2014-06-16 | Onyx Therapeutics Inc | 用於蛋白酶體抑制劑之調整釋放製劑 |
| SG11201507106PA (en) * | 2013-03-14 | 2015-10-29 | Onyx Therapeutics Inc | Dipeptide and tripeptide epoxy ketone protease inhibitors |
| AR095426A1 (es) * | 2013-03-14 | 2015-10-14 | Onyx Therapeutics Inc | Inhibidores tripeptídicos de la epoxicetona proteasa |
| KR102365509B1 (ko) * | 2013-03-14 | 2022-02-21 | 오닉스 세라퓨틱스, 인크. | 트리펩타이드 에폭시 케톤 프로테이스 억제제 |
| CN104710507B (zh) | 2013-12-11 | 2018-08-14 | 深圳翰宇药业股份有限公司 | 一种卡非佐米的制备方法 |
| CN104230857A (zh) | 2014-08-19 | 2014-12-24 | 上海皓元生物医药科技有限公司 | 卡非佐米(Carfilzomib)的中间体化合物的制备方法及其中间体化合物 |
| KR102524751B1 (ko) * | 2016-06-29 | 2023-04-21 | 케자르 라이프 사이언스 | 펩티드 에폭시케톤 면역프로테아제 저해제 및 그 전구체의 제조 방법 |
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2017
- 2017-06-29 KR KR1020197002872A patent/KR102524751B1/ko active IP Right Grant
- 2017-06-29 US US16/312,688 patent/US10781192B2/en active Active
- 2017-06-29 TW TW106121701A patent/TWI751177B/zh active
- 2017-06-29 MX MX2018016386A patent/MX2018016386A/es unknown
- 2017-06-29 SG SG11201811506UA patent/SG11201811506UA/en unknown
- 2017-06-29 BR BR112018077250-0A patent/BR112018077250A2/pt unknown
- 2017-06-29 IL IL302234A patent/IL302234A/en unknown
- 2017-06-29 JP JP2018568194A patent/JP7065044B2/ja active Active
- 2017-06-29 WO PCT/US2017/039975 patent/WO2018005781A1/en unknown
- 2017-06-29 EP EP17740180.9A patent/EP3478669B1/en active Active
- 2017-06-29 AU AU2017290147A patent/AU2017290147B2/en active Active
- 2017-06-29 KR KR1020237013160A patent/KR102571568B1/ko active IP Right Grant
- 2017-06-29 EA EA201990157A patent/EA201990157A1/ru unknown
- 2017-06-29 AR ARP170101808A patent/AR108919A1/es unknown
- 2017-06-29 CA CA3029418A patent/CA3029418A1/en active Pending
- 2017-06-29 IL IL263771A patent/IL263771B2/en unknown
- 2017-06-29 CN CN201780053331.3A patent/CN109641860B/zh active Active
- 2017-06-29 CN CN202410688315.3A patent/CN118684637A/zh active Pending
- 2017-06-29 EP EP23191555.4A patent/EP4296257A3/en active Pending
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2018
- 2018-12-28 CL CL2018003873A patent/CL2018003873A1/es unknown
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2019
- 2019-01-29 CO CONC2019/0000866A patent/CO2019000866A2/es unknown
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2020
- 2020-09-09 US US17/015,450 patent/US11498907B2/en active Active
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2022
- 2022-04-25 JP JP2022071492A patent/JP7392031B2/ja active Active
- 2022-10-13 US US17/965,064 patent/US11976053B2/en active Active
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