JPWO2020109526A5 - - Google Patents
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- Publication number
- JPWO2020109526A5 JPWO2020109526A5 JP2021531335A JP2021531335A JPWO2020109526A5 JP WO2020109526 A5 JPWO2020109526 A5 JP WO2020109526A5 JP 2021531335 A JP2021531335 A JP 2021531335A JP 2021531335 A JP2021531335 A JP 2021531335A JP WO2020109526 A5 JPWO2020109526 A5 JP WO2020109526A5
- Authority
- JP
- Japan
- Prior art keywords
- formulation
- glp
- receptor agonist
- glucagon receptor
- pegylated
- 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.)
- Pending
Links
- 101800001388 Oxyntomodulin Proteins 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 102400000319 Oxyntomodulin Human genes 0.000 claims description 15
- PXZWGQLGAKCNKD-DPNMSELWSA-N molport-023-276-326 Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 PXZWGQLGAKCNKD-DPNMSELWSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 239000000872 buffer Substances 0.000 claims description 11
- 159000000021 acetate salts Chemical class 0.000 claims description 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 239000007853 buffer solution Substances 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims 50
- 239000000203 mixture Substances 0.000 claims 50
- 229940123232 Glucagon receptor agonist Drugs 0.000 claims 20
- 229940089838 Glucagon-like peptide 1 receptor agonist Drugs 0.000 claims 18
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 16
- 102100040918 Pro-glucagon Human genes 0.000 claims 16
- 229920001223 polyethylene glycol Polymers 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 125000005647 linker group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 230000003442 weekly effect Effects 0.000 claims 6
- 230000000368 destabilizing effect Effects 0.000 claims 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- 235000018417 cysteine Nutrition 0.000 claims 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 4
- 239000012634 fragment Substances 0.000 claims 4
- 229940071643 prefilled syringe Drugs 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 235000001014 amino acid Nutrition 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 3
- 229940090047 auto-injector Drugs 0.000 claims 3
- 239000012669 liquid formulation Substances 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 239000008351 acetate buffer Substances 0.000 claims 2
- 239000012062 aqueous buffer Substances 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 210000004369 blood Anatomy 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 239000003755 preservative agent Substances 0.000 claims 2
- 238000004007 reversed phase HPLC Methods 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 125000001433 C-terminal amino-acid group Chemical group 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 108010024044 Glucagon-Like Peptide-2 Receptor Proteins 0.000 claims 1
- 102100032879 Glucagon-like peptide 2 receptor Human genes 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010056997 Impaired fasting glucose Diseases 0.000 claims 1
- 206010022095 Injection Site reaction Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 150000001483 arginine derivatives Chemical class 0.000 claims 1
- 229940072107 ascorbate Drugs 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000005277 cation exchange chromatography Methods 0.000 claims 1
- 239000007979 citrate buffer Substances 0.000 claims 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000010706 fatty liver disease Diseases 0.000 claims 1
- TWSALRJGPBVBQU-PKQQPRCHSA-N glucagon-like peptide 2 Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(O)=O)[C@@H](C)CC)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=CC=C1 TWSALRJGPBVBQU-PKQQPRCHSA-N 0.000 claims 1
- 230000004153 glucose metabolism Effects 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- 150000002741 methionine derivatives Chemical class 0.000 claims 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 238000001542 size-exclusion chromatography Methods 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
- 208000016261 weight loss Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862773651P | 2018-11-30 | 2018-11-30 | |
| US62/773,651 | 2018-11-30 | ||
| US201962821382P | 2019-03-20 | 2019-03-20 | |
| US62/821,382 | 2019-03-20 | ||
| PCT/EP2019/083022 WO2020109526A2 (en) | 2018-11-30 | 2019-11-29 | Oxyntomodulin peptide analog formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2022513176A JP2022513176A (ja) | 2022-02-07 |
| JPWO2020109526A5 true JPWO2020109526A5 (ko) | 2024-06-27 |
Family
ID=68886992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021531335A Pending JP2022513176A (ja) | 2018-11-30 | 2019-11-29 | オキシントモジュリンペプチド類似体製剤 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20200262887A1 (ko) |
| EP (1) | EP3886807A2 (ko) |
| JP (1) | JP2022513176A (ko) |
| KR (1) | KR20210135476A (ko) |
| CN (1) | CN113365606A (ko) |
| AU (1) | AU2019387342A1 (ko) |
| CA (1) | CA3120794A1 (ko) |
| IL (1) | IL283553A (ko) |
| MX (1) | MX2021006259A (ko) |
| PH (1) | PH12021551243A1 (ko) |
| WO (1) | WO2020109526A2 (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW202140061A (zh) * | 2020-01-10 | 2021-11-01 | 英商梅迪繆思有限公司 | 用於治療２型糖尿病中的慢性腎病和糖尿病性腎病的升糖素及ｇｌｐ－１協同促效劑 |
| CN117202924A (zh) * | 2020-12-07 | 2023-12-08 | 斯皮特弗尔制药有限责任公司 | 使用glp-1r和gcgr平衡激动剂降低血糖和/或体重的治疗方案和方法 |
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| US5932462A (en) | 1995-01-10 | 1999-08-03 | Shearwater Polymers, Inc. | Multiarmed, monofunctional, polymer for coupling to molecules and surfaces |
| US6214966B1 (en) | 1996-09-26 | 2001-04-10 | Shearwater Corporation | Soluble, degradable poly(ethylene glycol) derivatives for controllable release of bound molecules into solution |
| US6448369B1 (en) | 1997-11-06 | 2002-09-10 | Shearwater Corporation | Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation |
| US6436386B1 (en) | 2000-11-14 | 2002-08-20 | Shearwater Corporation | Hydroxyapatite-targeting poly (ethylene glycol) and related polymers |
| GB0121709D0 (en) | 2001-09-07 | 2001-10-31 | Imp College Innovations Ltd | Food inhibition agent |
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| US8263084B2 (en) | 2003-11-13 | 2012-09-11 | Hanmi Science Co., Ltd | Pharmaceutical composition for treating obesity-related disease comprising insulinotropic peptide conjugate |
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| AR079344A1 (es) * | 2009-12-22 | 2012-01-18 | Lilly Co Eli | Analogo peptidico de oxintomodulina, composicion farmaceutica que lo comprende y uso para preparar un medicamento util para tratar diabetes no insulinodependiente y/u obesidad |
| AR079345A1 (es) | 2009-12-22 | 2012-01-18 | Lilly Co Eli | Analogo peptidico de oxintomodulina |
| BR112013030933A2 (pt) * | 2011-06-02 | 2018-04-24 | Prolor Biotech Inc | agonistas do receptor de glp-1/glucágon de ação prolongada |
| EP3434687B1 (en) | 2011-06-10 | 2021-03-10 | Hanmi Science Co., Ltd. | Novel oxyntomodulin derivatives and pharmaceutical composition for treating obesity comprising the same |
| RU2014101697A (ru) | 2011-06-22 | 2015-07-27 | Индиана Юниверсити Рисерч Энд Текнолоджи Корпорейшн | Коагонисты рецепторов глюкагона/glp-1 |
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| WO2013163162A1 (en) | 2012-04-24 | 2013-10-31 | Amylin Pharmaceuticals, Llc | Site-specific enzymatic modification of exendins and analogs thereof |
| CN109096387B (zh) | 2012-06-04 | 2021-11-30 | 奥普科生物制品有限公司 | 聚乙二醇化的oxm变体 |
| KR101968344B1 (ko) | 2012-07-25 | 2019-04-12 | 한미약품 주식회사 | 옥신토모듈린 유도체를 포함하는 고지혈증 치료용 조성물 |
| KR101993393B1 (ko) | 2012-11-06 | 2019-10-01 | 한미약품 주식회사 | 옥신토모듈린 유도체를 포함하는 당뇨병 또는 비만성 당뇨병 치료용 조성물 |
| CA2890324C (en) * | 2012-11-06 | 2021-02-23 | Hanmi Pharm. Co., Ltd. | Liquid formulation of protein conjugate comprising the oxyntomodulin and an immunoglobulin fragment |
| KR20140088837A (ko) | 2013-01-03 | 2014-07-11 | 한미약품 주식회사 | Ｎ-말단 전하가 변형된 인슐린 분비 펩티드 유도체 |
| JP6572497B2 (ja) | 2013-12-18 | 2019-09-11 | ザ・スクリップス・リサーチ・インスティテュート | 修飾された治療剤、ステープル留めされたペプチド脂質複合体、及びそれらの組成物 |
| ES2897935T3 (es) | 2014-03-31 | 2022-03-03 | Hanmi Pharm Ind Co Ltd | Método para mejorar la solubilidad de proteína y péptido mediante el uso del enlace a un fragmento Fc de inmunoglobulina |
| CN106519015B (zh) | 2014-09-23 | 2020-04-17 | 深圳市图微安创科技开发有限公司 | 胃泌酸调节素类似物 |
| KR102527180B1 (ko) * | 2014-12-10 | 2023-04-27 | 옵코 바이오로직스 리미티드 | 장기간 작용성 ctp-변형된 성장 호르몬 폴리펩타이드의 제조 방법 |
| EP3468610A1 (en) * | 2016-06-09 | 2019-04-17 | OPKO Biologics Ltd. | Long-acting oxyntomodulin formulation and methods of producing and administering same |
-
2019
- 2019-11-27 US US16/698,329 patent/US20200262887A1/en active Pending
- 2019-11-29 JP JP2021531335A patent/JP2022513176A/ja active Pending
- 2019-11-29 EP EP19820673.2A patent/EP3886807A2/en active Pending
- 2019-11-29 CA CA3120794A patent/CA3120794A1/en active Pending
- 2019-11-29 CN CN201980089205.2A patent/CN113365606A/zh active Pending
- 2019-11-29 AU AU2019387342A patent/AU2019387342A1/en active Pending
- 2019-11-29 MX MX2021006259A patent/MX2021006259A/es unknown
- 2019-11-29 KR KR1020217020458A patent/KR20210135476A/ko active Search and Examination
- 2019-11-29 WO PCT/EP2019/083022 patent/WO2020109526A2/en active Application Filing
-
2021
- 2021-05-28 PH PH12021551243A patent/PH12021551243A1/en unknown
- 2021-05-30 IL IL283553A patent/IL283553A/en unknown
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