HRP20201985T1 - Piridonski spoj kao c-met inhibitor - Google Patents
Piridonski spoj kao c-met inhibitor Download PDFInfo
- Publication number
- HRP20201985T1 HRP20201985T1 HRP20201985TT HRP20201985T HRP20201985T1 HR P20201985 T1 HRP20201985 T1 HR P20201985T1 HR P20201985T T HRP20201985T T HR P20201985TT HR P20201985 T HRP20201985 T HR P20201985T HR P20201985 T1 HRP20201985 T1 HR P20201985T1
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- Croatia
- Prior art keywords
- compound
- pharmaceutically acceptable
- image
- acceptable salt
- group
- Prior art date
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- -1 Pyridone compound Chemical class 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 1
- YKPQUSLRUFLVDA-UHFFFAOYSA-N $l^{2}-azanylmethane Chemical compound [NH]C YKPQUSLRUFLVDA-UHFFFAOYSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 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
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Claims (17)
1. Spoj predstavljen formulom (I) ili farmaceutski prihvatljiva sol,
[image]
R1 je odabran između H ili F;
R2 je odabran između H ili CH3;
dok R2 nije H, konfiguracija atoma ugljika vezana za R2 je R ili S;
A je odabran iz skupine koju čine fenil, piridil, pirazolil, izoksazolil, izotiazolil i tiazolil, svaki od kojih je po izboru supstituiran s 1, 2 ili 3 R3;
R3 je odabran između CN, halogena, C(=O)NH2, ili je odabran iz skupine koju čine C1-6 alkil, C1-6 heteroalkil, i C3-6 cikloalkil, od kojih je svaki po izboru supstituiran s 1, 2 ili 3 R0;
R0je odabran između F, Cl, Br, I, OH, CN, NH2, C(=O)NH2 ili je odabran iz skupine koju čine C1-3 alkil, i C1-3 heteroalkil, od kojih je svaki po izboru supstituiran s 1, 2 ili 3 R';
R’se bira između F, Cl, Br, I, CN, OH, NH2, CH3, CH3CH2, CF3, CHF2 ili CH2F;
"hetero" u C1-3 heteroalkilu ili C1-6 heteroalkilu je odabran iz skupine koju čine -O-,
-C(=O)NR'-, -C(=O)NH-, -NR’- i -NH-;
u bilo kojem od gore navedenih slučajeva, broj heteroatoma ili heteroatomske skupine se neovisno bira od 1, 2 ili 3.
2. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 1, naznačeni time da je R0 odabran od F, Cl, Br, I, OH, CN, NH2, C(=O)NH2, CH3, CH3CH2, CF3, CHF2, CH2F, NH2CH2, (NH2)2CH, CH3O, CH3CH2O, CH3OCH2, CH3NH ili (CH3)2N.
3. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 1 ili 2, naznačeni time da je R1 H.
4. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 1 ili 2, naznačeni time da je R1 F.
5. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 1 ili 2, naznačeni time da je R2 H.
6. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 1 ili 2, naznačeni time da je R2 CH3.
7. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 6, naznačeni time da je konfiguracija atoma ugljika vezanog za R2 R.
8. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 6, naznačeni time da je konfiguracija atoma ugljika vezanog za R2 S.
9. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 1 ili 2, naznačeni time da je R3 odabran od CN, halogena, C(=O)NH2, ili je odabran iz skupine koju čine C1-3 alkil i C1-3heteroalkil, od kojih je svaki opcionalno supstituiran s 1, 2 ili 3 R0.
10. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 9, naznačeni time da je R3 odabran od CN, F, Cl, Br, CH3, CH3CH2, CF3, CHF2, CH2F, CH3O ili C(=O)NH2.
11. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 1 ili 2, naznačeni time da je A odabran iz skupine koju čine
[image]
koji je svaki opcionalno supstituiran s 1, 2 ili 3 R3.
12. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 11, naznačeni time da je A odabran iz skupine koju čine
[image]
[image]
13. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 12, naznačeni time da je A odabran iz skupine koju čine
[image]
i
[image]
14. Spoj ili farmaceutski prihvatljiva sol kako je definirano u zahtjevu 10 ili 13, naznačeni time da je A odabran iz skupine koju čine
[image]
[image]
15. Spoj kako je definiran u zahtjevu 1 odabran iz skupine koja se sastoji od
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
16. Farmaceutski pripravak, naznačen time što sadrži terapijski učinkovitu količinu spoja ili njegove farmaceutski prihvatljive soli kako je definirano u bilo kojem od zahtjeva 1-15, kao i farmaceutski prihvatljiv nosač.
17. Upotreba spoja ili njegove farmaceutski prihvatljive soli kako je definirano u bilo kojem od zahtjeva 1-15 ili farmaceutskog pripravka kako je definirano u zahtjevu 16 u proizvodnji lijeka za tretiranje tumora.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610954377 | 2016-10-27 | ||
| PCT/CN2017/107964 WO2018077227A1 (zh) | 2016-10-27 | 2017-10-27 | 作为c-MET抑制剂的吡啶酮类化合物 |
| EP17864813.5A EP3533787B1 (en) | 2016-10-27 | 2017-10-27 | Pyridone compound as c-met inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20201985T1 true HRP20201985T1 (hr) | 2021-02-05 |
Family
ID=62024383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20201985TT HRP20201985T1 (hr) | 2016-10-27 | 2020-12-10 | Piridonski spoj kao c-met inhibitor |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US10501443B2 (hr) |
| EP (1) | EP3533787B1 (hr) |
| JP (1) | JP6719679B2 (hr) |
| KR (1) | KR102070748B1 (hr) |
| CN (1) | CN109311812B (hr) |
| AU (1) | AU2017348810B2 (hr) |
| BR (1) | BR112019008415B1 (hr) |
| CA (1) | CA3041164C (hr) |
| CO (1) | CO2019005165A2 (hr) |
| DK (1) | DK3533787T3 (hr) |
| EA (1) | EA038108B1 (hr) |
| ES (1) | ES2835301T3 (hr) |
| HR (1) | HRP20201985T1 (hr) |
| HU (1) | HUE051734T2 (hr) |
| IL (1) | IL266126B (hr) |
| LT (1) | LT3533787T (hr) |
| MX (1) | MX2019004626A (hr) |
| MY (1) | MY189557A (hr) |
| PE (1) | PE20190912A1 (hr) |
| PH (1) | PH12019500875A1 (hr) |
| PL (1) | PL3533787T3 (hr) |
| PT (1) | PT3533787T (hr) |
| RS (1) | RS61126B1 (hr) |
| SG (1) | SG11201903801YA (hr) |
| SI (1) | SI3533787T1 (hr) |
| UA (1) | UA122737C2 (hr) |
| WO (1) | WO2018077227A1 (hr) |
| ZA (1) | ZA201903074B (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102374933B1 (ko) * | 2018-04-26 | 2022-03-15 | 푸젠 코선터 파마슈티컬 컴퍼니 리미티드 | c-Met 억제제의 결정형과 이의 염 형태 및 제조 방법 |
| CN113365997B (zh) * | 2019-02-01 | 2022-06-07 | 南京明德新药研发有限公司 | 作为c-Met抑制剂的含嘧啶基团的三并环类化合物 |
| WO2022063869A2 (en) | 2020-09-24 | 2022-03-31 | Merck Patent Gmbh | Compounds for the treatment of viral infections |
| WO2022253935A1 (en) | 2021-06-04 | 2022-12-08 | Merck Patent Gmbh | Compounds for the treatment of glioblastoma |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002002519A2 (en) | 2000-06-29 | 2002-01-10 | Bristol-Myers Squibb Pharma Company | THROMBIN OR FACTOR Xa INHIBITORS |
| CA2558272C (en) | 2004-03-05 | 2011-02-15 | Banyu Pharmaceutical Co., Ltd. | Pyridone derivative |
| MX2009008531A (es) * | 2007-02-16 | 2009-08-26 | Amgen Inc | Cetonas de heterociclilo que contienen nitrogeno y su uso como inhibidores de c-met. |
| DE102007032507A1 (de) * | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008062826A1 (de) * | 2008-12-23 | 2010-07-01 | Merck Patent Gmbh | Pyridazinonderivate |
| WO2013057101A1 (de) | 2011-10-17 | 2013-04-25 | Bayer Intellectual Property Gmbh | Substituierte oxadiazolylpyridinone und - pyridazinone als hif - hemmer |
| AU2013234767B2 (en) * | 2012-03-19 | 2017-02-23 | Merck Patent Gmbh | Combination of a 6-oxo-1,6-dihydro-pyridazine derivative having anti-cancer activity with other anti-tumor compounds |
| ES2679372T3 (es) * | 2012-10-11 | 2018-08-24 | Merck Patent Gmbh | Combinación de un derivado de 6-oxo-1,6-dihidro-piridazina que tiene actividad contra el cáncer con un inhibidor de MEK |
| SG11201704763SA (en) * | 2014-12-11 | 2017-07-28 | Merck Patent Gmbh | Combination of a 6-oxo-1,6-dihydro-pyridazine derivative having anti-cancer activity with a quinazoline derivative |
-
2017
- 2017-10-27 PL PL17864813T patent/PL3533787T3/pl unknown
- 2017-10-27 JP JP2019540379A patent/JP6719679B2/ja active Active
- 2017-10-27 US US16/343,387 patent/US10501443B2/en active Active
- 2017-10-27 CA CA3041164A patent/CA3041164C/en active Active
- 2017-10-27 EA EA201990952A patent/EA038108B1/ru unknown
- 2017-10-27 MY MYPI2019002142A patent/MY189557A/en unknown
- 2017-10-27 BR BR112019008415-0A patent/BR112019008415B1/pt active IP Right Grant
- 2017-10-27 MX MX2019004626A patent/MX2019004626A/es active IP Right Grant
- 2017-10-27 UA UAA201904417A patent/UA122737C2/uk unknown
- 2017-10-27 RS RS20201448A patent/RS61126B1/sr unknown
- 2017-10-27 AU AU2017348810A patent/AU2017348810B2/en active Active
- 2017-10-27 EP EP17864813.5A patent/EP3533787B1/en active Active
- 2017-10-27 PT PT178648135T patent/PT3533787T/pt unknown
- 2017-10-27 WO PCT/CN2017/107964 patent/WO2018077227A1/zh unknown
- 2017-10-27 DK DK17864813.5T patent/DK3533787T3/da active
- 2017-10-27 CN CN201780036464.XA patent/CN109311812B/zh active Active
- 2017-10-27 SG SG11201903801YA patent/SG11201903801YA/en unknown
- 2017-10-27 LT LTEP17864813.5T patent/LT3533787T/lt unknown
- 2017-10-27 PE PE2019000855A patent/PE20190912A1/es unknown
- 2017-10-27 HU HUE17864813A patent/HUE051734T2/hu unknown
- 2017-10-27 ES ES17864813T patent/ES2835301T3/es active Active
- 2017-10-27 KR KR1020197014236A patent/KR102070748B1/ko active IP Right Grant
- 2017-10-27 SI SI201730558T patent/SI3533787T1/sl unknown
-
2019
- 2019-04-18 IL IL266126A patent/IL266126B/en active IP Right Grant
- 2019-04-22 PH PH12019500875A patent/PH12019500875A1/en unknown
- 2019-05-16 ZA ZA2019/03074A patent/ZA201903074B/en unknown
- 2019-05-21 CO CONC2019/0005165A patent/CO2019005165A2/es unknown
-
2020
- 2020-12-10 HR HRP20201985TT patent/HRP20201985T1/hr unknown
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