RU2019123279A - Этан-сульфонатная соль производного хинолина - Google Patents
Этан-сульфонатная соль производного хинолина Download PDFInfo
- Publication number
- RU2019123279A RU2019123279A RU2019123279A RU2019123279A RU2019123279A RU 2019123279 A RU2019123279 A RU 2019123279A RU 2019123279 A RU2019123279 A RU 2019123279A RU 2019123279 A RU2019123279 A RU 2019123279A RU 2019123279 A RU2019123279 A RU 2019123279A
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- RU
- Russia
- Prior art keywords
- cancer
- crystal
- pharmaceutical composition
- hexahydro
- dioxo
- Prior art date
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 title 1
- 239000013078 crystal Substances 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- GPXHGUVJPXRRFG-UHFFFAOYSA-N C(C)S(=O)(=O)O.COC=1C=C2C(=CC=NC2=CC1OC)OC=1C=CC(=NC1)NC(=O)C=1C(N(C=2CCCC(C2C1)=O)C1=CC=CC=C1)=O Chemical compound C(C)S(=O)(=O)O.COC=1C=C2C(=CC=NC2=CC1OC)OC=1C=CC(=NC1)NC(=O)C=1C(N(C=2CCCC(C2C1)=O)C1=CC=CC=C1)=O GPXHGUVJPXRRFG-UHFFFAOYSA-N 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- -1 6,7-dimethoxy-4-quinolinyl Chemical group 0.000 claims 1
- 208000036764 Adenocarcinoma of the esophagus Diseases 0.000 claims 1
- 206010004593 Bile duct cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- 206010030137 Oesophageal adenocarcinoma Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010035603 Pleural mesothelioma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 201000005969 Uveal melanoma Diseases 0.000 claims 1
- 206010047741 Vulval cancer Diseases 0.000 claims 1
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims 1
- 208000026900 bile duct neoplasm Diseases 0.000 claims 1
- 201000009036 biliary tract cancer Diseases 0.000 claims 1
- 208000020790 biliary tract neoplasm Diseases 0.000 claims 1
- 206010006007 bone sarcoma Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000028653 esophageal adenocarcinoma Diseases 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000025189 neoplasm of testis Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000003437 pleural cancer Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 206010044412 transitional cell carcinoma Diseases 0.000 claims 1
- 208000023747 urothelial carcinoma Diseases 0.000 claims 1
- 210000001215 vagina Anatomy 0.000 claims 1
- 201000005102 vulva cancer Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (11)
1. N-{5-[(6,7-диметокси-4-хинолинил)окси]-2-пиридинил}-2,5-диоксо-1-фенил-1,2,5,6,7,8-гексагидро-3-хинолинкарбоксамид этансульфонат.
2. Кристалл N-{5-[(6,7-диметокси-4-хинолинил)окси]-2-пиридинил}-2,5-диоксо-1-фенил-1,2,5,6,7,8-гексагидро-3-хинолинкарбоксамид этансульфоната.
3. Кристалл по п. 2, где в порошковой рентгеновской дифрактограмме кристалл имеет пики при 2θ около 7,3, около 7,9, около 9,1, около 10,7, около 11,2, около 12,5, около 13,4, около 15,6, около 16,2, около 16,5, около 17,7, около 18,0, около 18,4, около 19,1, около 20,1, около 20,8, около 21,2, около 21,5, около 22,4, около 23,0, около 23,6, и около 24,0.
4. Кристалл по п. 2 или 3, имеющий характеристики порошковой рентгеновской дифрактограммы, показанной на фиг. 1.
5. Кристалл по пп. 2-4, где в дифференциальной сканирующей калориметрии кристалл имеет эндотермический пик с начальной температурой около 283°C или максимальной температурой около 286°C.
6. Кристалл по пп. 2-5, имеющий характеристики диаграммы дифференциальной сканирующей калориметрии, показанной на фиг. 2.
7. Фармацевтическая композиция, включающая N-{5-[(6,7-диметокси-4-хинолинил)окси]-2-пиридинил}-2,5-диоксо-1-фенил-1,2,5,6,7,8-гексагидро-3-хинолинкарбоксамид этансульфонат или кристалл по любому из пп. 2-6 и фармацевтически приемлемый носитель.
8. Фармацевтическая композиция по п. 7, которая представляет собой ингибитор Axl.
9. Фармацевтическая композиция по п. 7, которая представляет собой средство для профилактики и/или лечения заболевания, связанного с Axl.
10. Фармацевтическая композиция по п. 9, где заболевание, связанное с Axl, представляет собой рак, заболевание иммунной системы или заболевание системы кровообращения.
11. Фармацевтическая композиция по п. 10, где рак представляет собой лейкоз, злокачественную лимфому, множественную миелому, миелодиспластические синдромы, меланому, увеальную злокачественную меланому, рак головы и шеи, рак пищевода, эзофагеальную аденокарциному, рак желудка, рак толстого кишечника, рак толстой кишки, рак прямой кишки, рак печени, рак желчного пузыря и желчных путей, рак желчных протоков, рак поджелудочной железы, рак щитовидной железы, рак легкого, рак молочной железы, рак яичников, рак шейки матки, рак тела матки, рак эндометрия, рак влагалища, рак вульвы, почечно-клеточный рак, уротелиальную карциному, рак простаты, опухоль яичка, саркому костей и мягких тканей, рак кожи, глиому, опухоли головного мозга, мезотелиому плевры или рак с неизвестной первичной локализацией.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017-011835 | 2017-01-26 | ||
| JP2017011835 | 2017-01-26 | ||
| PCT/JP2018/002250 WO2018139527A1 (ja) | 2017-01-26 | 2018-01-25 | キノリン誘導体のエタンスルホン酸塩 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2022123981A Division RU2022123981A (ru) | 2017-01-26 | 2018-01-25 | Этан-сульфонатная соль производного хинолина |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2019123279A true RU2019123279A (ru) | 2021-02-26 |
| RU2019123279A3 RU2019123279A3 (ru) | 2021-03-31 |
Family
ID=62979439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2019123279A RU2019123279A (ru) | 2017-01-26 | 2018-01-25 | Этан-сульфонатная соль производного хинолина |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US10836747B2 (ru) |
| EP (1) | EP3575293B1 (ru) |
| JP (1) | JP6605763B2 (ru) |
| KR (1) | KR102571911B1 (ru) |
| CN (2) | CN119707932A (ru) |
| AU (1) | AU2018211801B2 (ru) |
| CA (1) | CA3051605C (ru) |
| DK (1) | DK3575293T3 (ru) |
| ES (1) | ES2872923T3 (ru) |
| HU (1) | HUE054883T2 (ru) |
| IL (1) | IL268221B (ru) |
| MX (1) | MX379140B (ru) |
| MY (1) | MY196680A (ru) |
| PH (1) | PH12019501693A1 (ru) |
| PL (1) | PL3575293T3 (ru) |
| PT (1) | PT3575293T (ru) |
| RU (1) | RU2019123279A (ru) |
| SG (1) | SG11201906819VA (ru) |
| TW (1) | TWI779007B (ru) |
| WO (1) | WO2018139527A1 (ru) |
| ZA (1) | ZA201904895B (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7156287B2 (ja) * | 2017-08-23 | 2022-10-19 | 小野薬品工業株式会社 | Ａｘｌ阻害剤を有効成分として含むがん治療剤 |
| US11826363B2 (en) | 2017-10-13 | 2023-11-28 | Ono Pharmaceutical Co., Ltd. | Therapeutic agent for solid cancers, which comprises Axl inhibitor as active ingredient |
| WO2024046292A1 (zh) * | 2022-08-30 | 2024-03-07 | 药捷安康(南京)科技股份有限公司 | 喹啉衍生物抑制剂的晶型及其制备方法及用途 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6428234B1 (en) * | 2000-01-07 | 2002-08-06 | Closure Medical Corporation | Adhesive applicator tips with improved flow properties |
| CA2396079A1 (en) | 2000-01-07 | 2001-07-19 | Transform Pharmaceuticals, Inc. | High-throughput formation, identification, and analysis of diverse solid-forms |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| WO2007033196A1 (en) | 2005-09-14 | 2007-03-22 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| WO2008048375A1 (en) | 2006-05-19 | 2008-04-24 | Bayer Healthcare Ag | Pyridonecarboxamide derivatives useful in treating hyper-proliferative and angiogenesis disorders |
| JP2009539878A (ja) | 2006-06-08 | 2009-11-19 | アレイ バイオファーマ、インコーポレイテッド | キノリン化合物および使用方法 |
| ES2391373T3 (es) | 2008-04-16 | 2012-11-23 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Derivados de quinoleína como inhibidores de la cinasa AXL |
| UY31800A (es) | 2008-05-05 | 2009-11-10 | Smithkline Beckman Corp | Metodo de tratamiento de cancer usando un inhibidor de cmet y axl y un inhibidor de erbb |
| JP5699075B2 (ja) | 2008-05-14 | 2015-04-08 | アムジエン・インコーポレーテツド | 癌の治療のためのｖｅｇｆ（ｒ）阻害剤および肝細胞増殖因子（ｃ−ｍｅｔ）阻害剤との組合せ |
| EP2349328A1 (en) | 2008-10-01 | 2011-08-03 | Ludwig Institute For Cancer Research | Methods for the treatment of cancer |
| JP2010178651A (ja) | 2009-02-04 | 2010-08-19 | Eisai R & D Management Co Ltd | Ｈｇｆｒ阻害物質の作用検定方法 |
| JP5525612B2 (ja) | 2010-07-23 | 2014-06-18 | 国立大学法人 東京大学 | 含窒素複素環誘導体 |
| JP5791412B2 (ja) | 2010-07-26 | 2015-10-07 | 日本碍子株式会社 | セラミックヒーター |
| EP2423208A1 (en) | 2010-08-28 | 2012-02-29 | Lead Discovery Center GmbH | Pharmaceutically active compounds as Axl inhibitors |
| DK2835131T3 (en) | 2010-12-14 | 2017-12-04 | Electrophoretics Ltd | Casein kinase 1 delta inhibitors (CK1 delta) |
| CN102816175B (zh) | 2011-06-09 | 2015-12-16 | 上海汇伦生命科技有限公司 | 一种杂环并吡啶酮类化合物,其中间体、制备方法和用途 |
| JP2013074633A (ja) | 2011-09-26 | 2013-04-22 | Oki Electric Ind Co Ltd | スイッチング電源装置及び現金自動預け払い装置 |
| UA114900C2 (uk) | 2011-11-14 | 2017-08-28 | Ігніта, Інк. | Похідні урацилу як інгібітори axl і c-met-кінази |
| TWI649308B (zh) | 2013-07-24 | 2019-02-01 | 小野藥品工業股份有限公司 | 喹啉衍生物 |
-
2018
- 2018-01-25 MX MX2019008787A patent/MX379140B/es unknown
- 2018-01-25 EP EP18744970.7A patent/EP3575293B1/en active Active
- 2018-01-25 WO PCT/JP2018/002250 patent/WO2018139527A1/ja not_active Ceased
- 2018-01-25 PL PL18744970T patent/PL3575293T3/pl unknown
- 2018-01-25 JP JP2018564622A patent/JP6605763B2/ja active Active
- 2018-01-25 AU AU2018211801A patent/AU2018211801B2/en active Active
- 2018-01-25 CA CA3051605A patent/CA3051605C/en active Active
- 2018-01-25 DK DK18744970.7T patent/DK3575293T3/da active
- 2018-01-25 MY MYPI2019004265A patent/MY196680A/en unknown
- 2018-01-25 CN CN202411731946.5A patent/CN119707932A/zh active Pending
- 2018-01-25 CN CN201880008442.7A patent/CN110225908A/zh active Pending
- 2018-01-25 KR KR1020197021641A patent/KR102571911B1/ko active Active
- 2018-01-25 RU RU2019123279A patent/RU2019123279A/ru unknown
- 2018-01-25 HU HUE18744970A patent/HUE054883T2/hu unknown
- 2018-01-25 TW TW107102692A patent/TWI779007B/zh active
- 2018-01-25 US US16/480,514 patent/US10836747B2/en active Active
- 2018-01-25 SG SG11201906819VA patent/SG11201906819VA/en unknown
- 2018-01-25 ES ES18744970T patent/ES2872923T3/es active Active
- 2018-01-25 PT PT187449707T patent/PT3575293T/pt unknown
-
2019
- 2019-07-22 IL IL268221A patent/IL268221B/en unknown
- 2019-07-23 PH PH12019501693A patent/PH12019501693A1/en unknown
- 2019-07-25 ZA ZA2019/04895A patent/ZA201904895B/en unknown
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