HUE032160T2 - Eljárás feniloximetil-nitro-imidazol-származékok elõállítására és ezek alkalmazása - Google Patents
Eljárás feniloximetil-nitro-imidazol-származékok elõállítására és ezek alkalmazása Download PDFInfo
- Publication number
- HUE032160T2 HUE032160T2 HUE12790895A HUE12790895A HUE032160T2 HU E032160 T2 HUE032160 T2 HU E032160T2 HU E12790895 A HUE12790895 A HU E12790895A HU E12790895 A HUE12790895 A HU E12790895A HU E032160 T2 HUE032160 T2 HU E032160T2
- Authority
- HU
- Hungary
- Prior art keywords
- nitro
- fexinidazole
- reaction
- imidazole
- acetone
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 22
- PQWRORAEWZRLNZ-UHFFFAOYSA-N 2-nitro-5-(phenoxymethyl)-1h-imidazole Chemical class N1C([N+](=O)[O-])=NC=C1COC1=CC=CC=C1 PQWRORAEWZRLNZ-UHFFFAOYSA-N 0.000 title description 2
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 46
- MIWWSGDADVMLTG-UHFFFAOYSA-N fexinidazole Chemical compound C1=CC(SC)=CC=C1OCC1=NC=C([N+]([O-])=O)N1C MIWWSGDADVMLTG-UHFFFAOYSA-N 0.000 description 30
- 229950004464 fexinidazole Drugs 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 19
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 17
- 239000012429 reaction media Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- JSAQDPJIVQMBAY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol Chemical compound CN1C(CO)=NC=C1[N+]([O-])=O JSAQDPJIVQMBAY-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 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 8
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000012544 monitoring process Methods 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 208000029080 human African trypanosomiasis Diseases 0.000 description 3
- 150000004957 nitroimidazoles Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- JLZXSFPSJJMRIX-UHFFFAOYSA-N 1-methyl-5-nitroimidazole Chemical compound CN1C=NC=C1[N+]([O-])=O JLZXSFPSJJMRIX-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 206010001935 American trypanosomiasis Diseases 0.000 description 2
- 208000024699 Chagas disease Diseases 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- 241000223109 Trypanosoma cruzi Species 0.000 description 2
- 206010047505 Visceral leishmaniasis Diseases 0.000 description 2
- 229940058965 antiprotozoal agent against amoebiasis and other protozoal diseases nitroimidazole derivative Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229930000044 secondary metabolite Natural products 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- BJNXOHUHVWNFLQ-UHFFFAOYSA-N 1-methyl-5-nitro-2-(phenoxymethyl)imidazole Chemical class C1=C([N+]([O-])=O)N(C)C(COC=2C=CC=CC=2)=N1 BJNXOHUHVWNFLQ-UHFFFAOYSA-N 0.000 description 1
- PDISGXFXQFGQFB-UHFFFAOYSA-N 2-(chloromethyl)-1-methyl-5-nitroimidazole Chemical compound CN1C(CCl)=NC=C1[N+]([O-])=O PDISGXFXQFGQFB-UHFFFAOYSA-N 0.000 description 1
- WQANSZZHQBVXOL-UHFFFAOYSA-N 2-(methoxymethylsulfonyl)-1-methyl-5-nitroimidazole Chemical compound COCS(=O)(=O)C1=NC=C([N+]([O-])=O)N1C WQANSZZHQBVXOL-UHFFFAOYSA-N 0.000 description 1
- KGLOORYXUIFLSZ-UHFFFAOYSA-N 4-(sulfanylmethyl)phenol Chemical compound OC1=CC=C(CS)C=C1 KGLOORYXUIFLSZ-UHFFFAOYSA-N 0.000 description 1
- 208000000230 African Trypanosomiasis Diseases 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000222712 Kinetoplastida Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000005448 Trichomonas Infections Diseases 0.000 description 1
- 206010044620 Trichomoniasis Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- -1 aliphatic ketones Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940095054 ammoniac Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 201000002612 sleeping sickness Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003407 synthetizing effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 208000037972 tropical disease Diseases 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (2)
- Sashalmi sgéstyposaokCl) k'pUîVi i ;·ί 'tîl'2'H-î!Hi!ÎïiKfkâ|>fï>-n ·}»«<' !» J ' >' ck\y?U<'=v:KS a kbXUkOiO k'posçk« fogîa|â îïi&iàh&îK >ts ‘iK ? > MMnfî! '|l rd<'VÎSÎ' *Ή) ,\P ikHiMk ό sav akilsks kiírnak eg>, » ! kot a,ka s ^ w. >\ ^". » ' " a* ' k«' * ^>nK's oktásv.!. J ,tlUss.Ut :S2asgfH.;n?.í6|a jeiettfóu-ben & ruk< iókerOlKifoyeket ágy sa&búiyoxw. bogy 3 «rul»w>***al«nM kí^b:.; 8*&^r víto L o-iIkí V- < / r!vhCl!) #« 0«).; k-pkgu sxskyärÄ vegyítetek; bí sx 1|y kgfsk rekíkésfegyte bîî^Muik 4^mcbbncrk.apm-fc»<ikisk a* a) tepésfesU Ιΐΐβΐί» »kciôkMilmôny^d agy s/shàKoxva, bogy ax (Í) testent vsgyiiMΜ jvptetís \i-g>steîte dímcnzábxlásft íikettííhcto K'tyea. c> s rmkcioetegySw -m ;() keptetss vegyütetet nabob forgója foanójAfcut à; a U ds>'sU*ï«iîv*f 3« v,y'-h.k a akibuk v- »Mî ev?tbe« v otóbbíl rissststjok..
- 2. λ? t xgvnypont serina ey&ate.. a?Kd a «sukkîofü sx«bs»Hücm rcskeibk v^psbÄsäm Ästrsas sxssr-ymwMoxnx egy poláros aptoiikus .verves »USover y Λ .'. igénypont vertets e$hK »P*>i a pol^s apíobkus szerves «tdósxergpí. sifctéfesCkiÖlwao ^ N , <.' ^ ; K' iíi' ^ s ^s'\v'Í0l»svl ΗΛϋν ^AvWifl a. Az I -3. igéoypootok tamteiyike «««at} eljárás, ahol a porstonaöc^kstijstoas k&usrnkÄsÄ: 7k Az 's ·· 4 igAsypansak bí»:íí:eíy=kc iacsaZ; dsánK :shn; * raa-Assz alAaUlsAas iÁsi ázz) llg&lasa sarsMisíí öigászAzsl készüli aldsís fónMíáksk sAko.zs·«::;:® »φΑ hozz® ;« kiazsikzAidraAsaai·!·:;aktro4;nkk;:iasiK'z ügy, lasgy a ísskaloalsgyA |4';: ß-s>ä pzg a<ss« hsMk k#isï#s4klëîgn:taryôli, Á Az l ~ SApzypostok káppök'slíe sasAkk <?f|É#k az: ;p:|épsbsn em!:4 teli oldoszerszl készük aklâpéÂ.! száí^azö S'eskcíöetaívMz ögv, áögv a ís~ zkdéközsgai 2SÖ €-*ől meg feízhalaílö kómémékletég Μ||Φ ék áAstás iäsMkkißalegyal 40^ C-pl insféglpök. í; Az: I - ;>. sgáííViAíspök::báízpsivlke szenkp^skasfas Akik AiA íé|>é|kíH:széí®:;^ az (1) káplAüzagyülsPMk a aj iéfsés szérisg ài^irôklçnli^â#.-«ízét:.Mi%#Ä· k. Az i: - 7. ígégygöSHök káíTssélyska sienmi ellát ég almi a c> lépésbol ïAtnnazè takkàlï^égÿMi a A 7 > kts i ii v\^ s i j Au \ otu <. · v >\ s ^ Kík c **oï» val ^ s. s kvig <1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2012/073321 WO2014079497A1 (en) | 2012-11-22 | 2012-11-22 | Method for preparing phenyloxymethyl-nitro-imidazole derivatives and use of same |
| EP12790895.2A EP2922822B1 (en) | 2012-11-22 | 2012-11-22 | Method for preparing phenyloxymethyl-nitro-imidazole derivatives and use of same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE032160T2 true HUE032160T2 (hu) | 2017-09-28 |
Family
ID=47222105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE12790895A HUE032160T2 (hu) | 2012-11-22 | 2012-11-22 | Eljárás feniloximetil-nitro-imidazol-származékok elõállítására és ezek alkalmazása |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9758488B2 (hu) |
| EP (1) | EP2922822B1 (hu) |
| CN (1) | CN104797562B (hu) |
| AP (1) | AP3759A (hu) |
| BR (1) | BR112015011446A2 (hu) |
| CA (1) | CA2892334C (hu) |
| CR (1) | CR20150286A (hu) |
| CY (1) | CY1118983T1 (hu) |
| EC (1) | ECSP15025960A (hu) |
| ES (1) | ES2618800T3 (hu) |
| HR (1) | HRP20170390T1 (hu) |
| HU (1) | HUE032160T2 (hu) |
| IL (1) | IL238934A (hu) |
| MX (1) | MX365587B (hu) |
| PL (1) | PL2922822T3 (hu) |
| SG (1) | SG11201504047TA (hu) |
| SI (1) | SI2922822T1 (hu) |
| WO (1) | WO2014079497A1 (hu) |
| ZA (1) | ZA201503063B (hu) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111454931A (zh) * | 2012-11-21 | 2020-07-28 | 益普生生物创新有限公司 | 用于制备经蛋白水解处理的多肽的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299090A (en) | 1964-03-27 | 1967-01-17 | Merck & Co Inc | Nitroimidazoles |
| EG11928A (en) * | 1974-12-16 | 1979-03-31 | Hoechst Ag | Process for preparing of 1-alkyl-2-(phenoxy-methyl)-5-nitro-imidazoles |
| DE2459395C2 (de) * | 1974-12-16 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | 1-Alkyl-2-(phenoxymethyl)-5-nitro-imidazole, Verfahren zu ihrer Herstellung und pharmazeutische Mittel |
| EG12284A (en) * | 1975-07-12 | 1978-09-30 | Hoechst Ag | Process for the preparation of 1-methyl-2-(phenyl 6 oxymethyl)-5-nitro-imidazoles |
| KR20050040746A (ko) * | 2003-10-27 | 2005-05-03 | 주식회사 엘지생명과학 | ＰＰＡＲγ와 ＰＰＡＲα의 활성을 항진시키는 신규화합물, 그것의 제조방법, 및 그것을 함유한 약제 조성물 |
| WO2011151651A1 (en) * | 2010-06-03 | 2011-12-08 | Arrow Therapeutics Limited | Benzodiazepine compounds useful for the treatment of hepatitis c |
-
2012
- 2012-11-22 CN CN201280077219.0A patent/CN104797562B/zh not_active Expired - Fee Related
- 2012-11-22 AP AP2015008475A patent/AP3759A/en active
- 2012-11-22 BR BR112015011446A patent/BR112015011446A2/pt not_active Application Discontinuation
- 2012-11-22 HR HRP20170390TT patent/HRP20170390T1/hr unknown
- 2012-11-22 SG SG11201504047TA patent/SG11201504047TA/en unknown
- 2012-11-22 WO PCT/EP2012/073321 patent/WO2014079497A1/en not_active Ceased
- 2012-11-22 CA CA2892334A patent/CA2892334C/en not_active Expired - Fee Related
- 2012-11-22 ES ES12790895.2T patent/ES2618800T3/es active Active
- 2012-11-22 PL PL12790895T patent/PL2922822T3/pl unknown
- 2012-11-22 MX MX2015006519A patent/MX365587B/es active IP Right Grant
- 2012-11-22 EP EP12790895.2A patent/EP2922822B1/en active Active
- 2012-11-22 HU HUE12790895A patent/HUE032160T2/hu unknown
- 2012-11-22 US US14/647,017 patent/US9758488B2/en active Active
- 2012-11-22 SI SI201230891A patent/SI2922822T1/sl unknown
-
2015
- 2015-05-04 ZA ZA2015/03063A patent/ZA201503063B/en unknown
- 2015-05-20 IL IL238934A patent/IL238934A/en active IP Right Grant
- 2015-05-28 CR CR20150286A patent/CR20150286A/es unknown
- 2015-06-17 EC ECIEPI201525960A patent/ECSP15025960A/es unknown
-
2017
- 2017-03-28 CY CY20171100384T patent/CY1118983T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CY1118983T1 (el) | 2018-01-10 |
| CN104797562B (zh) | 2017-10-03 |
| EP2922822B1 (en) | 2016-12-28 |
| AP3759A (en) | 2016-07-31 |
| HRP20170390T1 (hr) | 2017-05-05 |
| ECSP15025960A (es) | 2016-01-29 |
| CR20150286A (es) | 2015-10-19 |
| ES2618800T3 (es) | 2017-06-22 |
| AP2015008475A0 (en) | 2015-05-31 |
| IL238934A (en) | 2017-12-31 |
| ZA201503063B (en) | 2016-01-27 |
| WO2014079497A1 (en) | 2014-05-30 |
| MX365587B (es) | 2019-06-07 |
| SI2922822T1 (sl) | 2017-04-26 |
| CA2892334C (en) | 2019-10-08 |
| IL238934A0 (en) | 2015-07-30 |
| BR112015011446A2 (pt) | 2017-07-11 |
| US20150291536A1 (en) | 2015-10-15 |
| CA2892334A1 (en) | 2014-05-30 |
| CN104797562A (zh) | 2015-07-22 |
| SG11201504047TA (en) | 2015-06-29 |
| EP2922822A1 (en) | 2015-09-30 |
| US9758488B2 (en) | 2017-09-12 |
| MX2015006519A (es) | 2015-07-21 |
| PL2922822T3 (pl) | 2017-06-30 |
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