KR20150126659A - 항생제 화합물의 히드로클로리드 염 - Google Patents
항생제 화합물의 히드로클로리드 염 Download PDFInfo
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- KR20150126659A KR20150126659A KR1020157027597A KR20157027597A KR20150126659A KR 20150126659 A KR20150126659 A KR 20150126659A KR 1020157027597 A KR1020157027597 A KR 1020157027597A KR 20157027597 A KR20157027597 A KR 20157027597A KR 20150126659 A KR20150126659 A KR 20150126659A
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- Prior art keywords
- amino
- compound
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- salt
- glycine
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 133
- 239000003242 anti bacterial agent Substances 0.000 title description 6
- 150000003840 hydrochlorides Chemical class 0.000 title description 6
- 230000003115 biocidal effect Effects 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 29
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 87
- 150000003839 salts Chemical class 0.000 claims description 82
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 70
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 46
- 229930006000 Sucrose Natural products 0.000 claims description 46
- 239000005720 sucrose Substances 0.000 claims description 46
- -1 2- amino-5-chloro-4-thiazolyl Chemical group 0.000 claims description 43
- 239000004471 Glycine Substances 0.000 claims description 43
- 239000012458 free base Substances 0.000 claims description 34
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
- 238000003860 storage Methods 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- 108010059993 Vancomycin Proteins 0.000 claims description 17
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 14
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- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 84
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- 206010057190 Respiratory tract infections Diseases 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
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- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 229940124587 cephalosporin Drugs 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
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- 239000008351 acetate buffer Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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- 150000001780 cephalosporins Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
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- 238000004458 analytical method Methods 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000008176 lyophilized powder Substances 0.000 description 7
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- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
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- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
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- 125000006513 pyridinyl methyl group Chemical group 0.000 description 5
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- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- LCTORFDMHNKUSG-XTTLPDOESA-N vancomycin monohydrochloride Chemical compound Cl.O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 LCTORFDMHNKUSG-XTTLPDOESA-N 0.000 description 4
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361779065P | 2013-03-13 | 2013-03-13 | |
| US61/779,065 | 2013-03-13 | ||
| PCT/US2014/021064 WO2014158952A1 (en) | 2013-03-13 | 2014-03-06 | Hydrochloride salts of an antibiotic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150126659A true KR20150126659A (ko) | 2015-11-12 |
Family
ID=50483481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157027597A Withdrawn KR20150126659A (ko) | 2013-03-13 | 2014-03-06 | 항생제 화합물의 히드로클로리드 염 |
Country Status (32)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2980537A1 (en) * | 2015-03-24 | 2016-09-29 | Elevance Renewable Sciences, Inc. | Polyol esters of metathesized fatty acids and uses thereof |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4434287A (en) * | 1975-02-20 | 1984-02-28 | Ciba-Geigy Corporation | Cephalosporin derivatives |
| AR229883A1 (es) | 1978-05-26 | 1983-12-30 | Glaxo Group Ltd | Procedimiento para la preparacion de antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)-acetamido)-3-(1-piridinometil)-cef-3-em-4-carboxilato |
| US4626534A (en) | 1984-07-23 | 1986-12-02 | Eli Lilly And Company | Pharmaceutical formulation |
| DE3801179A1 (de) | 1988-01-18 | 1989-07-27 | Hoechst Ag | Stabilisierung von cephalosporinderivaten durch trocknung mit einem stabilisator sowie stabile zubereitungsformen mit cephalosporinderivaten |
| JPH0331449A (ja) | 1989-06-27 | 1991-02-12 | Yamaha Corp | リードフレーム用Ｆｅ―Ｎｉ合金 |
| DE69004921T2 (de) | 1989-09-30 | 1994-05-05 | Eisai Co Ltd | Injizierbare Cephalosporinpräparate und ihre Anwendung. |
| JPH03193735A (ja) | 1989-12-22 | 1991-08-23 | Shionogi & Co Ltd | グリコペプチド系抗生物質の安定化組成物 |
| JP4142149B2 (ja) | 1997-07-10 | 2008-08-27 | 明治製菓株式会社 | バンコマイシンの凍結乾燥製剤 |
| TWI335332B (en) * | 2001-10-12 | 2011-01-01 | Theravance Inc | Cross-linked vancomycin-cephalosporin antibiotics |
| PL1618114T3 (pl) * | 2003-04-16 | 2010-12-31 | Sandoz Ag | Sposoby otrzymywania cefepimy |
| ATE450540T1 (de) | 2003-05-23 | 2009-12-15 | Theravance Inc | Quervernetzte glycopeptid-cephalosporin- antibiotika |
| US6878868B2 (en) | 2003-06-24 | 2005-04-12 | Mcmillan Stacy L. | Portable high-hat device |
| US7067482B2 (en) | 2003-07-11 | 2006-06-27 | Theravance, Inc. | Cross-linked glycopeptide-cephalosporin antibiotics |
| TWI342312B (en) | 2003-10-22 | 2011-05-21 | Theravance Inc | Hydrochloride salts of a glycopeptide phosphonate derivative |
| EP1656930A1 (en) | 2004-11-10 | 2006-05-17 | Basilea Pharmaceutica AG | Stabilized freeze-dried formulation for cephalosporin derivatives |
| US20080103121A1 (en) | 2006-10-30 | 2008-05-01 | Gole Dilip J | Cephalosporin derivative formulation |
| FR2932177B1 (fr) | 2008-06-06 | 2012-11-30 | Inst Francais Du Petrole | Procede d'hydrogenation selective sur un catalyseur contenant de l'or. |
| JP2010105965A (ja) | 2008-10-30 | 2010-05-13 | Taiyo Yakuhin Kogyo Kk | バンコマイシン製剤 |
| US8431539B2 (en) | 2009-09-17 | 2013-04-30 | Eagle Pharmaceuticals, Inc. | Formulations of daptomycin |
| US20110124551A1 (en) | 2009-11-23 | 2011-05-26 | Eagle Pharmaceuticals, Inc. | Formulations of daptomycin |
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2014
- 2014-03-06 SM SM20170369T patent/SMT201700369T1/it unknown
- 2014-03-06 JP JP2016500713A patent/JP6482523B2/ja active Active
- 2014-03-06 UA UAA201509921A patent/UA115086C2/uk unknown
- 2014-03-06 MD MDA20150101A patent/MD4599C1/ro active IP Right Grant
- 2014-03-06 CN CN201480013969.0A patent/CN105120883B/zh active Active
- 2014-03-06 BR BR112015022716A patent/BR112015022716A2/pt not_active Application Discontinuation
- 2014-03-06 HU HUE14717248A patent/HUE033738T2/hu unknown
- 2014-03-06 EA EA201591697A patent/EA027282B1/ru unknown
- 2014-03-06 GE GEAP201413957A patent/GEP20186874B/en unknown
- 2014-03-06 SI SI201430302T patent/SI2968446T1/sl unknown
- 2014-03-06 RS RS20170621A patent/RS56141B1/sr unknown
- 2014-03-06 TW TW103107730A patent/TWI608845B/zh not_active IP Right Cessation
- 2014-03-06 MX MX2015012170A patent/MX361984B/es active IP Right Grant
- 2014-03-06 KR KR1020157027597A patent/KR20150126659A/ko not_active Withdrawn
- 2014-03-06 HR HRP20171188TT patent/HRP20171188T1/hr unknown
- 2014-03-06 CA CA2902720A patent/CA2902720A1/en not_active Abandoned
- 2014-03-06 WO PCT/US2014/021064 patent/WO2014158952A1/en not_active Ceased
- 2014-03-06 AU AU2014241481A patent/AU2014241481B9/en not_active Ceased
- 2014-03-06 PL PL14717248T patent/PL2968446T3/pl unknown
- 2014-03-06 LT LTEP14717248.0T patent/LT2968446T/lt unknown
- 2014-03-06 US US14/198,956 patent/US9161990B2/en active Active
- 2014-03-06 ES ES14717248.0T patent/ES2633964T3/es active Active
- 2014-03-06 DK DK14717248.0T patent/DK2968446T3/en active
- 2014-03-06 SG SG11201507235YA patent/SG11201507235YA/en unknown
- 2014-03-06 ME MEP-2017-133A patent/ME02854B/me unknown
- 2014-03-06 EP EP14717248.0A patent/EP2968446B1/en active Active
- 2014-03-06 PT PT147172480T patent/PT2968446T/pt unknown
- 2014-03-07 AR ARP140100742A patent/AR095044A1/es unknown
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2015
- 2015-08-18 IL IL240663A patent/IL240663A0/en not_active IP Right Cessation
- 2015-09-11 PH PH12015502060A patent/PH12015502060A1/en unknown
- 2015-09-11 ZA ZA2015/06748A patent/ZA201506748B/en unknown
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2017
- 2017-02-17 JP JP2017028372A patent/JP2017082016A/ja not_active Withdrawn
- 2017-07-28 CY CY20171100810T patent/CY1119316T1/el unknown
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2018
- 2018-08-17 JP JP2018153560A patent/JP2018177817A/ja not_active Withdrawn
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