HRP20151022T1 - Razdvajanje enantiomera derivata triazina korištenjem vinske kiseline - Google Patents
Razdvajanje enantiomera derivata triazina korištenjem vinske kiseline Download PDFInfo
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- HRP20151022T1 HRP20151022T1 HRP20151022TT HRP20151022T HRP20151022T1 HR P20151022 T1 HRP20151022 T1 HR P20151022T1 HR P20151022T T HRP20151022T T HR P20151022TT HR P20151022 T HRP20151022 T HR P20151022T HR P20151022 T1 HRP20151022 T1 HR P20151022T1
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- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- halogen
- amino
- Prior art date
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- -1 triazine derivatives enantiomers Chemical class 0.000 title claims 26
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims 3
- 238000000926 separation method Methods 0.000 title claims 3
- 235000002906 tartaric acid Nutrition 0.000 title claims 2
- 239000011975 tartaric acid Substances 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical group 0.000 claims 15
- 238000000034 method Methods 0.000 claims 13
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims 12
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 12
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 150000003918 triazines Chemical class 0.000 claims 7
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000003892 tartrate salts Chemical class 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001345 alkine derivatives Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 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 claims 1
- GFICWFZTBXUVIG-UHFFFAOYSA-N 6-n,6-n,4-trimethyl-1,4-dihydro-1,3,5-triazine-2,6-diamine Chemical compound CC1N=C(N)NC(N(C)C)=N1 GFICWFZTBXUVIG-UHFFFAOYSA-N 0.000 claims 1
- UXHLCYMTNMEXKZ-UHFFFAOYSA-N 6-n,6-n,4-trimethyl-1,4-dihydro-1,3,5-triazine-2,6-diamine;hydrochloride Chemical group Cl.CC1N=C(N)NC(N(C)C)=N1 UXHLCYMTNMEXKZ-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims 1
- 239000001358 L(+)-tartaric acid Substances 0.000 claims 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (13)
1. Postupak za razdvajanje enantiomera derivata triazina s formulom (I) ispod:
[image]
pri čemu:
R1, R2, R3 i R4 su odabrani neovisno od slijedećih skupina:
- H;
- (C1-C20) alkila proizvoljno supstituiranog s halogenom, (C1-C5) alkilom, (C1-C5) alkoksi ili (C3-C8) cikloalkilom;
- (C2-C20) alkilena proizvoljno supstituiranog s halogenom, (C1-C5) alkilom ili (C1-C5) alkoksi;
- (C2-C20) alkina proizvoljno supstituiranog s halogenom, (C1-C5) alkilom ili (C1-C5) alkoksi;
- (C3-C8) cikloalkila proizvoljno supstituiranog s (C1-C5) alkilom ili (C1-C5) alkoksi;
- (C3-C8) heterocikloalkila koji ima jedan ili više hetero atoma odabranih od N, O i S i proizvoljno supstituiran s (C1-C5) alkilom ili (C1-C5) alkoksi;
- (C6-C14) arilalkil (C1-C20) proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
- (C6-C14) aril proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom; ili
- (C5-C13) heteroaril koji ima jedan ili više hetero atoma odabranih od N, O i S i proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
R1 i R2, s jedne strane, i R3 i R4, s druge strane, moguće tvore s atomom dušika na koji su spojeni n-člani prsten (n između 3 i 8) koji proizvoljno sadrži jedan ili više hetero atoma odabranih od N, O i S i koji su moguće supstituirani sa amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
R5 je izabran iz sljedećih skupina:
- (C1-C20) alkil proizvoljno supstituiran s amino, hidroksil, tio, halogen, (C1-C5) alkil, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometil, karboksil, karboksimetil ili karboksietil;
- (C2-C20) alkilen proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
- (C2-C20) alkin proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
- (C3-C8) cikloalkil proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
- (C3-C8) heterocikloalkil koji ima jedan ili više hetero atoma odabranih od N, O i S i proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
- (C6-C14) aril proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
- (C5-C13) heteroaril koji ima jedan ili više hetero atoma odabranih od N, O i S i proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom;
- (C6-C14) arilalkil(C1-C5) proizvoljno supstituiran s amino, hidroksilom, tio, halogenom, (C1-C5) alkilom, (C1-C5) alkoksi, (C1-C5) alkiltio, (C1-C5) alkilamino, (C6-C14) ariloksi, (C6-C14) arilalkoksi, (C1-C5), cijano, trifluorometilom, karboksilom, karboksimetilom ili karboksietilom,
ili njihova sol,
naznačen time da sadrži slijedeće korake:
- korak 1: tvorbu diastereoizomerne tartratne soli derivata triazina reakcijom soli derivata triazina sa jednim enantiomerom vinske kiseline,
- korak 2: razdvajanje oba diastereoizomera tartratne soli,
- korak 3: transformaciju najmanje jednog izoliranog diastereoizomera tartratne soli u drugu sol, te
- korak 4: obnavljanje soli triazina dobivene u koraku 3.
2. Postupak prema zahtjevu 1, naznačen time da najmanje jedan od R3 i R4 je vodikov atom, naročito da R3 i R4 su oba atomi vodika.
3. Postupak prema zahtjevu 1 ili 2, naznačen time da R1 i R2 neovisno predstavljaju C1 do C3 alkil skupine, poželjno metil.
4. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da spoj s formulom (I) je u obliku soli, naročito hidrokloridne soli.
5. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da je derivat triazina s formulom (I) odabran između:
2-amino-3,6-dihidro-4-dimetilamino-6-metil-1,3,5-triazina,
2-amino-6-cikloheksil-3,6-dihidro-4-dimetilamino-1,3,5-triazin,a
i njihove soli.
6. Postupak prema zahtjevu 4, naznačen time da derivat triazina je 2-amino-3,6-dihidro-4-dimetilamino-6-metil-1,3,5-triazin hidroklorid.
7. Postupak prema bilo kojem od zahtjeva 1-6, naznačen time da je u reakcijskom mediju prisutna baza.
8. Postupak prema zahtjevu 7, naznačen time da baza je trietilamin.
9. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da se korak 1 provodi pomoću reakcije derivata triazina s formulom (I) sa L-(+)-vinskom kiselinom.
10. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da se korak 1 provodi u otapalu i otapalo iz koraka 1 je poželjno metanol.
11. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da se korak 2 provodi pomoću filtracije ili centrifugiranjem.
12. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da se korak 3 provodi u otapalu i otapalo iz koraka 3 je poželjno etanol.
13. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time da se korak 3 provodi u otapalu i otapalo iz koraka 3 je aceton.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10306327 | 2010-12-01 | ||
| EP11788512.9A EP2646422B1 (en) | 2010-12-01 | 2011-11-30 | Separation of triazine derivatives enantiomers using tartaric acid |
| PCT/EP2011/071347 WO2012072663A1 (en) | 2010-12-01 | 2011-11-30 | Separation of triazine derivatives enantiomers using tartaric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20151022T1 true HRP20151022T1 (hr) | 2015-12-18 |
Family
ID=45047827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20151022TT HRP20151022T1 (hr) | 2010-12-01 | 2015-09-28 | Razdvajanje enantiomera derivata triazina korištenjem vinske kiseline |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US8742103B2 (hr) |
| EP (1) | EP2646422B1 (hr) |
| JP (1) | JP5758010B2 (hr) |
| KR (1) | KR101530924B1 (hr) |
| CN (1) | CN103228635B (hr) |
| AU (1) | AU2011334992B2 (hr) |
| BR (1) | BR112013010115B1 (hr) |
| CA (1) | CA2816357C (hr) |
| CY (1) | CY1117407T1 (hr) |
| DK (1) | DK2646422T3 (hr) |
| EA (1) | EA022300B1 (hr) |
| ES (1) | ES2548038T3 (hr) |
| HR (1) | HRP20151022T1 (hr) |
| HU (1) | HUE026090T2 (hr) |
| IL (1) | IL226053A (hr) |
| ME (1) | ME02208B (hr) |
| MX (1) | MX345822B (hr) |
| PL (1) | PL2646422T3 (hr) |
| PT (1) | PT2646422E (hr) |
| RS (1) | RS54397B1 (hr) |
| SI (1) | SI2646422T1 (hr) |
| SM (1) | SMT201500230B (hr) |
| TW (1) | TWI428311B (hr) |
| WO (1) | WO2012072663A1 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019069230A1 (en) | 2017-10-02 | 2019-04-11 | Poxel | METHODS OF TREATING CARDIAC INSUFFICIENCY WITH PRESERVED EJECTION FRACTION |
| AU2019282727A1 (en) | 2018-06-06 | 2020-11-26 | Metavant Sciences Gmbh | Methods of treating subjects having diabetes with chronic kidney disease |
| MX2020013567A (es) | 2018-06-14 | 2021-05-27 | Poxel | Tableta recubierta con pelicula que comprende un derivado de triazina para su uso en el tratamiento de la diabetes. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2804113B1 (fr) | 2000-01-26 | 2004-06-18 | Lipha | Derives animes de dihydro-1,3,5-triazine et leurs applications en therapeutique |
| FR2853650B1 (fr) * | 2003-04-10 | 2006-07-07 | Merck Sante Sas | Procede de dedoublement d'amines utiles pour le traitement de desordres associes au syndrome d'insulino-resistance |
| US7458318B2 (en) | 2006-02-01 | 2008-12-02 | Speedline Technologies, Inc. | Off-axis illumination assembly and method |
| DE102008007314A1 (de) | 2008-02-02 | 2009-08-06 | Merck Patent Gmbh | Verfahren zur Herstellung von 3,6-Dihydro-1,3,5-triazinderivaten |
| HUE027532T2 (en) | 2008-05-23 | 2016-10-28 | Poxel Sas | Process for the preparation of 3,6-dihydro-1,3,5-triazine derivatives |
-
2011
- 2011-11-30 US US13/990,924 patent/US8742103B2/en active Active
- 2011-11-30 AU AU2011334992A patent/AU2011334992B2/en not_active Ceased
- 2011-11-30 TW TW100144035A patent/TWI428311B/zh active
- 2011-11-30 KR KR1020137017212A patent/KR101530924B1/ko active IP Right Grant
- 2011-11-30 CA CA 2816357 patent/CA2816357C/en active Active
- 2011-11-30 WO PCT/EP2011/071347 patent/WO2012072663A1/en active Application Filing
- 2011-11-30 EA EA201300650A patent/EA022300B1/ru not_active IP Right Cessation
- 2011-11-30 PT PT117885129T patent/PT2646422E/pt unknown
- 2011-11-30 ME MEP-2015-154A patent/ME02208B/me unknown
- 2011-11-30 SI SI201130606T patent/SI2646422T1/sl unknown
- 2011-11-30 RS RS20150615A patent/RS54397B1/en unknown
- 2011-11-30 ES ES11788512.9T patent/ES2548038T3/es active Active
- 2011-11-30 PL PL11788512T patent/PL2646422T3/pl unknown
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