HRP20171687T1 - Postupak pripremanja spojeva alfa-galaktozil keramida - Google Patents
Postupak pripremanja spojeva alfa-galaktozil keramida Download PDFInfo
- Publication number
- HRP20171687T1 HRP20171687T1 HRP20171687TT HRP20171687T HRP20171687T1 HR P20171687 T1 HRP20171687 T1 HR P20171687T1 HR P20171687T T HRP20171687T T HR P20171687TT HR P20171687 T HRP20171687 T HR P20171687T HR P20171687 T1 HRP20171687 T1 HR P20171687T1
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- 238000000034 method Methods 0.000 title claims 14
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000006239 protecting group Chemical group 0.000 claims 11
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 238000010511 deprotection reaction Methods 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- -1 carboxybenzyl group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims 1
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical group OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 125000004036 acetal group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000013595 glycosylation Effects 0.000 claims 1
- 238000006206 glycosylation reaction Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (14)
1. Postupak pripremanja spojeva formule (I):
[image]
koji obuhvaća fazu a) glikozilacije, poželjno u prisutnosti Lewisove kiseline, spoja formule (II):
[image]
sa spojem formule (III):
[image]
pri čemu navedena faza a) daje spoj formule (IV):
[image]
u kojoj :
- R1 predstavlja ravnu ili razgranatu, zasićenu ili nezasićenu C1-C20 alkil skupinu, koja je proizvoljno supstituirana;
- R2 predstavlja ravnu ili razgranatu, zasićenu ili nezasićenu C1-C30 alkil skupinu, koja je proizvoljno supstituirana;
- R3 predstavlja C1-C6 alkil skupinu proizvoljnu supstituiranu, C3-C6 cikloalkil, C1-C6 acil ili benzoil skupinu; R4 predstavlja H ili C1-C6 alkil skupinu koja je proizvoljno supstituirana; ili
- R3 i R4 tvore zajedno s atomom dušika za koji su vezani, C2-C6 heterocikloalkil skupinu ili C1-C5 heteroaril skupinu;
- PG1 predstavlja zaštitnu skupinu hidroksilne funkcije;
- PG2 predstavlja primarnu zaštitnu skupinu amin funkcije;
- PG3 predstavlja zaštitnu skupinu hidroksilne funkcije;
- PG'3 predstavlja zaštitnu skupinu hidroksilne funkcije, proizvoljno tvoreći, zajedno s PG3 i atomima kisika i ugljika za koje su vezani, C3-C6 heterocikloalkil, koji je proizvoljno supstituiran; i
- LG predstavlja odlazeću skupinu,
pri čemu se:
izraz cikloalkil odnosi na zasićene monocikličke ugljikovodikove skupine s 3 do 6 atoma ugljika, kod kojih bilo koji atom prstena koji se može supstituirati, može biti supstituiran s nekim supstituentom;
izraz heterocikloalkil se odnosi na nearomatski 5-7-člani monocikal,
sustav prstena s 1-3 heteroatoma i 2-6 atoma ugljika, pri čemu su navedeni heteroatomi odabrani između O, N, ili S, pri čemu bilo koji atom prstena koji se može supstituirati,
može biti supstituiran s nekim supstituentom; i
izraz heteroaril se odnosi na aromatski 5-6-člani monociklički sustav prstena s 1-4 heteroatoma i 1-5 atoma ugljika, pri čemu su navedeni heteroatomi odabrani između O, N, ili S pri čemu bilo koji atom prstena koji se može supstituirati, može biti supstituiran s nekim supstituentom.
2. Postupak prema zahtjevu 1, naznačen time da se spoj formule (I) dobije iz spoja formule (IV) uklanjanjem zaštite zaštitnih skupina PG1, PG2, PG3 i PG'3, i sprezanjem sa spojem formule R2COCl (VII), u kojoj je R2 kako je definirano u zahtjevu 1.
3. Postupak prema zahtjevu 1, naznačen time da nakon faze a) obuhvaća fazu b) uklanjanja zaštite zaštitnih skupina PG1 i PG2 spoja formule (IV), poželjno hidrogenolizom u prisutnosti metalnog katalizatora,
pri čemu navedena faza b) daje spoj formule (V):
[image]
u kojoj su R1, R3, R4, PG3 i PG'3 kao što je definirano u zahtjevu 1.
4. Postupak prema zahtjevu 3, naznačen time da nakon faze b) obuhvaća:
- fazu c) sprezanja spoja formule (V) sa spojem formule R2COCl (VII), u prisutnosti baze, i
- fazu d) uklanjanja zaštite zaštitnih skupina PG3 i PG'3 proizvoda dobivenog u fazi c),
pri čemu navedene faze daju spoj formule (I).
5. Postupak prema zahtjevu 1, naznačen time da nakon faze a) obuhvaća fazu b') uklanjanja zaštite zaštitnih skupina PG1, PG2, PG3 i PG'3 spoja formule (IV), poželjno hidrogenolizom u prisustvu metalnog katalizatora,
pri čemu navedena faza b') daje spoj formule (VI):
[image]
u kojoj su R1, R3 i R4 kako je definirano u zahtjevu 1.
6. Postupak prema zahtjevu 5, naznačen time da nakon faze b') obuhvaća fazu c') sprezanja spoja formule (VI) sa spojem formule R2COCl (VII), u prisutnosti baze, pri čemu navedena faza c') daje spoj formule (I).
7. Postupak prema zahtjevu 1, naznačen time da LG predstavlja trikloroacetimidat skupinu.
8. Postupak prema zahtjevu 1, naznačen time da R1 predstavlja ravnu zasićenu C1-C20 alkil skupinu, poželjno s formulom -C14H29.
9. Postupak prema zahtjevu 1, naznačen time da R2 predstavlja ravnu zasićenu C1-C20 alkil skupinu, poželjno s formulom -C23H47.
10. Postupak prema zahtjevu 1, naznačen time da:
- R3 je acil grupa, poželjno s formulom -C(O)CH3; i
- R4 je H.
11. Postupak prema zahtjevu 1, naznačen time da zaštitna skupina PG1 predstavlja benzil skupinu, koja je proizvoljno supstituirana.
12. Postupak prema zahtjevu 1, naznačen time da zaštitna skupina PG2 predstavlja karboksibenzil skupinu, koja je proizvoljno supstituirana.
13. Postupak prema zahtjevu 1, naznačen time da zaštitne skupine PG3 i PG'3 tvore zajedno sa dva atoma kisika za koje su vezani, izopropiliden acetal skupinu.
14. Sinteza intermedijera formula (II-3), (II-2), (IV-2), (IV-3), (V), (VI) i (VIII):
[image]
[image]
[image]
naznačena time da su skupine R1, R3, R4, kako su definirane u bilo kojem od zahtjeva 1 do 13,
i u kojima skupine PG1 predstavljaju benzil skupinu (Bn),
PG2 je karboksibenzil skupina,
PG'3 tvori zajedno s PG3 i atomima kisika i ugljika za koje su vezani, C3-C6 heterocikloalkil, proizvoljno supstituiran i
LG je acetimidat formule -O-C(=NH)-CRiRiiRiii, u kojoj su Ri, Rii i Riii, isti ili različiti, odabrani iz skupine koju čine atom vodika, atom klora, atom fluora i metil skupina.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261720098P | 2012-10-30 | 2012-10-30 | |
| EP12306355.4A EP2727929A1 (en) | 2012-10-30 | 2012-10-30 | Method of preparation of alpha galactosyl ceramides compounds |
| EP13783936.1A EP2920194B1 (en) | 2012-10-30 | 2013-10-30 | Method of preparation of alpha-galactosyl ceramides compounds |
| PCT/EP2013/072711 WO2014067995A1 (en) | 2012-10-30 | 2013-10-30 | METHOD OF PREPARATION OF α-GALACTOSYL CERAMIDES COMPOUNDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171687T1 true HRP20171687T1 (hr) | 2017-12-15 |
Family
ID=47172560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171687TT HRP20171687T1 (hr) | 2012-10-30 | 2017-11-06 | Postupak pripremanja spojeva alfa-galaktozil keramida |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US10870671B2 (hr) |
| EP (2) | EP2727929A1 (hr) |
| JP (1) | JP6140830B2 (hr) |
| CN (2) | CN109503682B (hr) |
| AR (1) | AR093270A1 (hr) |
| AU (1) | AU2013340901B2 (hr) |
| BR (1) | BR112015009720B1 (hr) |
| CA (1) | CA2888391C (hr) |
| CU (1) | CU24311B1 (hr) |
| CY (1) | CY1119697T1 (hr) |
| DK (1) | DK2920194T3 (hr) |
| ES (1) | ES2655655T3 (hr) |
| HR (1) | HRP20171687T1 (hr) |
| HU (1) | HUE035530T2 (hr) |
| IL (1) | IL238515B (hr) |
| LT (1) | LT2920194T (hr) |
| MX (1) | MX363944B (hr) |
| PL (1) | PL2920194T3 (hr) |
| PT (1) | PT2920194T (hr) |
| RU (1) | RU2662156C2 (hr) |
| SI (1) | SI2920194T1 (hr) |
| WO (1) | WO2014067995A1 (hr) |
| ZA (1) | ZA201502844B (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11820789B2 (en) * | 2018-06-15 | 2023-11-21 | Carbocode S.A. | Glycosylated sphingoid bases and production thereof |
| CN110479184B (zh) * | 2019-08-05 | 2021-09-07 | 华侨大学 | 一种琼脂糖基乳化剂及其制备方法和应用 |
| CA3212136A1 (en) | 2021-03-01 | 2022-09-09 | Deciduous Therapeutics, Inc. | Compounds for activating invariant natural killer t-cells and methods of use in eliminating inflammatory senescent cells |
| WO2024050020A1 (en) * | 2022-08-31 | 2024-03-07 | Deciduous Therapeutics, Inc. | Invariant natural killer t-cell activators |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758395A (fr) * | 1969-11-03 | 1971-05-03 | Upjohn Co | Procede de conversion d'halogenures de cis-glucosyle peracyles et nouveaux composes en derivant |
| US4310505A (en) * | 1979-11-08 | 1982-01-12 | California Institute Of Technology | Lipid vesicles bearing carbohydrate surfaces as lymphatic directed vehicles for therapeutic and diagnostic substances |
| FR2711138B1 (fr) | 1993-10-12 | 1995-11-24 | Oreal | Céramides, leur procédé de préparation et leurs applications en cosmétique et en dermopharmacie. |
| CN1405172A (zh) * | 2001-08-13 | 2003-03-26 | 青岛海洋大学 | 一种乳糖胺脂及其制备方法和应用 |
| CN101331146B (zh) * | 2005-10-25 | 2012-06-13 | 路德维格癌症研究院 | α-半乳糖神经酰胺的类似物及其用途 |
| ES2397975T3 (es) | 2006-04-07 | 2013-03-12 | The Scrips Research Institute | Galactosilceramida modificada para el tratamiento de enfermedades cancerosas |
| CN101012254A (zh) * | 2006-08-29 | 2007-08-08 | 中国海洋大学 | 一种α－半乳糖鞘糖脂的2’－OH衍生物及其制备方法 |
| ES2654382T3 (es) * | 2011-01-05 | 2018-02-13 | National Taiwan University | Método para la preparación de glucoesfingolípidos |
-
2012
- 2012-10-30 EP EP12306355.4A patent/EP2727929A1/en not_active Withdrawn
-
2013
- 2013-10-30 LT LTEP13783936.1T patent/LT2920194T/lt unknown
- 2013-10-30 WO PCT/EP2013/072711 patent/WO2014067995A1/en active Application Filing
- 2013-10-30 ES ES13783936.1T patent/ES2655655T3/es active Active
- 2013-10-30 CA CA2888391A patent/CA2888391C/en active Active
- 2013-10-30 BR BR112015009720-0A patent/BR112015009720B1/pt active IP Right Grant
- 2013-10-30 DK DK13783936.1T patent/DK2920194T3/en active
- 2013-10-30 US US14/439,642 patent/US10870671B2/en active Active
- 2013-10-30 PT PT137839361T patent/PT2920194T/pt unknown
- 2013-10-30 JP JP2015538504A patent/JP6140830B2/ja active Active
- 2013-10-30 AR ARP130103950A patent/AR093270A1/es active IP Right Grant
- 2013-10-30 CN CN201811555848.5A patent/CN109503682B/zh active Active
- 2013-10-30 CU CUP2015000042A patent/CU24311B1/xx unknown
- 2013-10-30 HU HUE13783936A patent/HUE035530T2/en unknown
- 2013-10-30 PL PL13783936T patent/PL2920194T3/pl unknown
- 2013-10-30 SI SI201330907T patent/SI2920194T1/en unknown
- 2013-10-30 RU RU2015116422A patent/RU2662156C2/ru active
- 2013-10-30 CN CN201380056606.0A patent/CN104812769A/zh active Pending
- 2013-10-30 EP EP13783936.1A patent/EP2920194B1/en active Active
- 2013-10-30 MX MX2015005592A patent/MX363944B/es active IP Right Grant
- 2013-10-30 AU AU2013340901A patent/AU2013340901B2/en active Active
-
2015
- 2015-04-24 ZA ZA2015/02844A patent/ZA201502844B/en unknown
- 2015-04-28 IL IL238515A patent/IL238515B/en active IP Right Grant
-
2017
- 2017-11-06 HR HRP20171687TT patent/HRP20171687T1/hr unknown
- 2017-12-18 CY CY20171101324T patent/CY1119697T1/el unknown
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