HRP20171346T1 - Postupak za pripremu 2-trifluorometil izonikotinske kiseline i estera - Google Patents
Postupak za pripremu 2-trifluorometil izonikotinske kiseline i estera Download PDFInfo
- Publication number
- HRP20171346T1 HRP20171346T1 HRP20171346TT HRP20171346T HRP20171346T1 HR P20171346 T1 HRP20171346 T1 HR P20171346T1 HR P20171346T T HRP20171346T T HR P20171346TT HR P20171346 T HRP20171346 T HR P20171346T HR P20171346 T1 HRP20171346 T1 HR P20171346T1
- Authority
- HR
- Croatia
- Prior art keywords
- conversion
- process according
- chloride
- preparation
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 13
- 238000002360 preparation method Methods 0.000 title claims 3
- BZFGKBQHQJVAHS-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(C(F)(F)F)=C1 BZFGKBQHQJVAHS-UHFFFAOYSA-N 0.000 title claims 2
- 150000002148 esters Chemical class 0.000 title claims 2
- 238000006243 chemical reaction Methods 0.000 claims 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical class FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 101000890887 Homo sapiens Trace amine-associated receptor 1 Proteins 0.000 claims 1
- 102100040114 Trace amine-associated receptor 1 Human genes 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
Classifications
-
- 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
- C07D213/02—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 having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- 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
- C07D213/02—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 having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- 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
- C07D213/02—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 having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- C07D213/02—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 having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1. Postupak, naznačen time, da je za pripremu 2-trifluorometil izonikotinske kiseline i estera prema sljedećoj formuli:
[image]
pri čemu R1 predstavlja vodik ili C1-6-alkil i obuhvaća konverziju 2-trifluorometil piridin derivata prema sljedećoj formuli:
[image]
gdje X predstavlja halogen ili -OSO2CY3, dok Y je halogen, s ugljičnim monoksidom (CO);
u prisutnosti reaktanta R1OH, pri čemu R1 ima značenje koje je gore navedeno i u prisutnosti
paladijevog kompleksa koji djeluje kao katalizator odabran iz paladij(II)klorida s ligandom
1,1’-Bis-(difenilfosfino)ferocen (dfff).
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time, da se konverzija obavlja pod CO-tlakom od 5 do 100 bara.
3. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 ili 2, naznačen time, da se konverzija obavlja u prisutnosti baze.
4. Postupak u skladu s bilo kojim od patentnih zahtjeva od 1 do 3, naznačen time, da se konverzija obavlja pri reakcijskoj temperaturi između 50°C i 170°C.
5. Postupak u skladu s bilo kojim od patentnih zahtjeva od 1 do 4, naznačen time, da u slučaju konverzije s reaktantom R1OH, pri čemu R1 je C1-6-alkil, nakon konverzije s ugljičnim monoksidom slijedi obrada u kojoj vodikov klorid proizvodi agens.
6. Postupak u skladu s patentnim zahtjevom 5, naznačen time, da je vodikov klorid koji proizvodi agens, odabran iz tionil klorida ili acetil klorida.
7. Postupak u skladu s patentnim zahtjevom 5 ili 6, naznačen time, da se obrada u kojoj vodikov klorid proizvodi agens, obavlja u uvjetima refluksiranja reakcijske smjese.
8. Postupak u skladu s bilo kojim od patentnih zahtjeva od 1 do 7, naznačen time, da R1 predstavlja vodik, metil, etil ili i-propil.
9. Postupak u skladu s bilo kojim od patentnih zahtjeva od 1 do 8, naznačen time, da R1 predstavlja vodik ili metil.
10. Postupak u skladu s bilo kojim od patentnih zahtjeva od 1 do 9, naznačen time, da X predstavlja fluor, klor, brom, jod ili trifluorometansulfonil.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva od 1 do 10, naznačen time, da X predstavlja klor.
12. Uporaba postupka u skladu s bilo kojem od zahtjeva od 1 do 11, naznačena time, da je za pripravu TAAR1 agonista prema sljedećoj formuli:
[image]
pri čemu
R2 je (CH2)n-(O)o-heterocikloalkil, opcionalno supstituiran s C1-6-alkilom, hidroksidom, halogenom ili
-(CH2)p-arilom;
n je 0, 1, 2;
o je 0, 1;
p je 0, 1, 2;
ili njegova farmaceutski prikladna kiselinska adicijska sol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12193065 | 2012-11-16 | ||
| PCT/EP2013/073715 WO2014076127A1 (en) | 2012-11-16 | 2013-11-13 | Process for the preparation of 2-trifluoromethyl isonicotinic acid and esters |
| EP13792327.2A EP2920150B1 (en) | 2012-11-16 | 2013-11-13 | Process for the preparation of 2-trifluoromethyl isonicotinic acid and esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171346T1 true HRP20171346T1 (hr) | 2017-10-20 |
Family
ID=47189790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171346TT HRP20171346T1 (hr) | 2012-11-16 | 2017-09-06 | Postupak za pripremu 2-trifluorometil izonikotinske kiseline i estera |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9481650B2 (hr) |
| EP (1) | EP2920150B1 (hr) |
| JP (1) | JP6267221B2 (hr) |
| KR (1) | KR20150083864A (hr) |
| CN (1) | CN104781236B (hr) |
| AU (1) | AU2013346882B2 (hr) |
| BR (1) | BR112015010120A2 (hr) |
| CA (1) | CA2885155C (hr) |
| ES (1) | ES2641376T3 (hr) |
| HK (1) | HK1207377A1 (hr) |
| HR (1) | HRP20171346T1 (hr) |
| IL (1) | IL237904A (hr) |
| MX (1) | MX362274B (hr) |
| MY (1) | MY170491A (hr) |
| NZ (1) | NZ706266A (hr) |
| PL (1) | PL2920150T3 (hr) |
| RU (1) | RU2654486C2 (hr) |
| SG (1) | SG11201503573WA (hr) |
| SI (1) | SI2920150T1 (hr) |
| WO (1) | WO2014076127A1 (hr) |
| ZA (1) | ZA201503201B (hr) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4160295B2 (ja) * | 2000-12-08 | 2008-10-01 | 武田薬品工業株式会社 | ３−ピリジル基を有する置換チアゾール誘導体、その製造法および用途 |
| EP1348706B1 (en) * | 2000-12-08 | 2009-08-19 | Takeda Pharmaceutical Company Limited | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| TW200307669A (en) * | 2002-04-15 | 2003-12-16 | Nippon Soda Co | Novel oxime o-ether compound, production process thereof, and agricultural or horticultural bactericide |
| JP4972804B2 (ja) * | 2004-08-31 | 2012-07-11 | Ｍｓｄ株式会社 | 新規置換イミダゾール誘導体 |
| US7745477B2 (en) * | 2006-02-07 | 2010-06-29 | Hoffman-La Roche Inc. | Heteroaryl and benzyl amide compounds |
| WO2010100050A1 (en) * | 2009-03-05 | 2010-09-10 | F. Hoffmann-La Roche Ag | Pyridine-2-yl-carboxylic acid amides |
| CN102724880B (zh) * | 2009-11-13 | 2016-09-14 | 瑞塞普托斯有限责任公司 | 1-磷酸鞘氨醇受体调节剂及手性合成方法 |
| US9132136B2 (en) * | 2010-08-02 | 2015-09-15 | Hoffmann-La Roche Inc. | Pharmaceutical combination |
| JP2012106964A (ja) * | 2010-11-19 | 2012-06-07 | Ishihara Sangyo Kaisha Ltd | ２‐シクロプロピル‐６‐ハロゲノメチル‐４‐トリフルオロメチルピリジン誘導体及びその製造方法 |
| SG190839A1 (en) * | 2010-11-19 | 2013-07-31 | Incyte Corp | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
-
2013
- 2013-11-13 MX MX2015005376A patent/MX362274B/es active IP Right Grant
- 2013-11-13 BR BR112015010120A patent/BR112015010120A2/pt not_active Application Discontinuation
- 2013-11-13 ES ES13792327.2T patent/ES2641376T3/es active Active
- 2013-11-13 MY MYPI2015701543A patent/MY170491A/en unknown
- 2013-11-13 KR KR1020157012637A patent/KR20150083864A/ko active IP Right Grant
- 2013-11-13 AU AU2013346882A patent/AU2013346882B2/en not_active Ceased
- 2013-11-13 NZ NZ70626613A patent/NZ706266A/en not_active IP Right Cessation
- 2013-11-13 US US14/442,971 patent/US9481650B2/en active Active
- 2013-11-13 SG SG11201503573WA patent/SG11201503573WA/en unknown
- 2013-11-13 CN CN201380059373.XA patent/CN104781236B/zh not_active Expired - Fee Related
- 2013-11-13 JP JP2015542256A patent/JP6267221B2/ja not_active Expired - Fee Related
- 2013-11-13 WO PCT/EP2013/073715 patent/WO2014076127A1/en active Application Filing
- 2013-11-13 RU RU2015119876A patent/RU2654486C2/ru active
- 2013-11-13 CA CA2885155A patent/CA2885155C/en not_active Expired - Fee Related
- 2013-11-13 EP EP13792327.2A patent/EP2920150B1/en active Active
- 2013-11-13 SI SI201330776T patent/SI2920150T1/sl unknown
- 2013-11-13 PL PL13792327T patent/PL2920150T3/pl unknown
-
2015
- 2015-03-23 IL IL237904A patent/IL237904A/en active IP Right Grant
- 2015-05-08 ZA ZA2015/03201A patent/ZA201503201B/en unknown
- 2015-08-19 HK HK15108050.3A patent/HK1207377A1/xx not_active IP Right Cessation
-
2017
- 2017-09-06 HR HRP20171346TT patent/HRP20171346T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150083864A (ko) | 2015-07-20 |
| US20150291530A1 (en) | 2015-10-15 |
| CA2885155C (en) | 2021-02-16 |
| MX2015005376A (es) | 2015-07-21 |
| BR112015010120A2 (pt) | 2017-07-11 |
| RU2654486C2 (ru) | 2018-05-21 |
| MY170491A (en) | 2019-08-08 |
| MX362274B (es) | 2019-01-10 |
| SG11201503573WA (en) | 2015-06-29 |
| JP2016500060A (ja) | 2016-01-07 |
| CN104781236B (zh) | 2018-04-24 |
| CN104781236A (zh) | 2015-07-15 |
| AU2013346882B2 (en) | 2017-05-04 |
| NZ706266A (en) | 2019-10-25 |
| IL237904A (en) | 2017-10-31 |
| CA2885155A1 (en) | 2014-05-22 |
| RU2015119876A (ru) | 2017-01-10 |
| JP6267221B2 (ja) | 2018-01-24 |
| ES2641376T3 (es) | 2017-11-08 |
| HK1207377A1 (en) | 2016-01-29 |
| AU2013346882A1 (en) | 2015-04-02 |
| US9481650B2 (en) | 2016-11-01 |
| PL2920150T3 (pl) | 2017-11-30 |
| EP2920150A1 (en) | 2015-09-23 |
| EP2920150B1 (en) | 2017-07-19 |
| SI2920150T1 (sl) | 2017-10-30 |
| ZA201503201B (en) | 2016-09-28 |
| WO2014076127A1 (en) | 2014-05-22 |
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