HRP20191513T1 - Fenotiazinski spojevi za liječenje blagog kognitivnog poremećaja - Google Patents
Fenotiazinski spojevi za liječenje blagog kognitivnog poremećaja Download PDFInfo
- Publication number
- HRP20191513T1 HRP20191513T1 HRP20191513T HRP20191513T1 HR P20191513 T1 HRP20191513 T1 HR P20191513T1 HR P20191513 T HRP20191513 T HR P20191513T HR P20191513 T1 HRP20191513 T1 HR P20191513T1
- Authority
- HR
- Croatia
- Prior art keywords
- unsubstituted
- substituted
- carboaryl
- aliphatic
- independently selected
- Prior art date
Links
- 208000010877 cognitive disease Diseases 0.000 title claims 3
- 208000027061 mild cognitive impairment Diseases 0.000 title claims 3
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 title 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 13
- 125000005488 carboaryl group Chemical group 0.000 claims 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 7
- -1 diaminophenothiazine compound Chemical class 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000000129 anionic group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010001956 Amnestic symptoms Diseases 0.000 claims 1
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims 1
- 229960004373 acetylcholine Drugs 0.000 claims 1
- 229940127243 cholinergic drug Drugs 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000037149 energy metabolism Effects 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000002438 mitochondrial effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Claims (23)
1. Uporaba diaminofenotiazinskog spoja, naznačena time, da je za proizvodnju lijeka za liječenje blagog kognitivnog poremećaja (BKP) kod pacijenta koji od njega boluje, gdje se navedeni spoj bira od spojeva slijedećih formula:
gdje se svaki od R1, R2, R4, R6, R8, i R9 neovisno bira od:
- H;
- F; -Cl; -Br; -I;
- OH; -OR;
- SH; -SR;
- NO2;
- C(=O)R;
- C(=O)OH; -C(=O)OR;
- C(=O)NH2; -C(=O)NHR; -C(=O)NR2; -C(=O)NRN1RN2;
- NH2; -NHR; -NR2; -NRN1RN2;
- NHC(=O)H; -NRC(=O)H; -NHC(=O)R; -NRC(=O)R;
- R;
gdje se svaki R neovisno bira od:
nesupstituiranog alifatskog C1-6alkila; supstituiranog alifatskog C1-6alkila;
nesupstituiranog alifatskog C2-6alkenila; supstituiranog alifatskog C2-6alkenila;
nesupstituiranog C3-6cikloalkila; supstituiranog C3-6cikloalkila;
nesupstituiranog C6-10karboarila; supstituiranog C6-10karboarila;
nesupstituiranog C5-10heteroarila; supstituiranog C5-10heteroarila;
nesupstituiranog C6-10karboarila-C1-4alkila; supstituiranog C6-10karboarila-C1-4alkila;
gdje, kod svake skupine -NRN1RN2, neovisno, RN1 i RN2 se uzimaju zajedno s dušikovom skupinom na koji se vežu tvoreći prsten s 3 do 7 atoma u prstenu;
i gdje, kod svake skupine NR3NA i NR3NB, ako su prisutne:
svaki od R3NA i R3NB se neovisno biraju od:
-H;
nesupstituiranog alifatskog C1-6alkila; supstituiranog alifatskog C1-6alkila;
nesupstituiranog alifatskog C2-6alkenila; supstituiranog alifatskog C2-6alkenila;
nesupstituiranog C3-6cikloalkila; supstituiranog C3-6cikloalkila;
nesupstituiranog C6-10karboarila; supstituiranog C6-10karboarila;
nesupstituiranog C5-10heteroarila; supstituiranog C5-10heteroarila;
nesupstituiranog C6-10karboarila-C1-4alkila; supstituiranog C6-10karboarila-C1-4al kila;
ili; R3NA i R3NB se uzimaju zajedno s dušikovom skupinom na koji se vežu tvoreći prsten s 3 do 7 atoma u prstenu;
i gdje, kod svake skupine =NR3NC, ukoliko je prisutna, -R3NC se neovisno bira od:
-H;
nesupstituiranog alifatskog C1-6alkila; supstituiranog alifatskog C1-6alkila;
nesupstituiranog alifatskog C2-6alkenila; supstituiranog alifatskog C2-6alkenila;
nesupstituiranog C3-6cikloalkila; supstituiranog C3-6cikloalkila;
nesupstituiranog C6-10karboarila; supstituiranog C6-10karboarila;
nesupstituiranog C5-10heteroarila; supstituiranog C5-10heteroarila;
nesupstituiranog C6-10karboarila-C1-4alkila; supstituiranog C6-10karboarila-C1-4alkila;
i gdje kod svake skupine -NR7NAR7NB, ukoliko je prisutna: svaki se R7NA i R7NB neovisno bira od:
-H;
nesupstituiranog alifatskog C1-6alkila; supstituiranog alifatskog C1-6alkila;
nesupstituiranog alifatskog C2-6alkenila; supstituiranog alifatskog C2-6alkenila;
nesupstituiranog C3-6cikloalkila; supstituiranog C3-6cikloalkila;
nesupstituiranog C6-10karboarila; supstituiranog C6-10karboarila;
nesupstituiranog C5-10heteroarila; supstituiranog C5-10heteroarila;
nesupstituiranog C5-10karboarila-C1-4alkila; supstituiranog C6-10karboarila-C1-4alkila;
ili; R7NAi R7NB se uzimaju zajedno s dušikovom skupinom na koji se vežu tvoreći prsten s 3 do 7 atoma u prstenu;
i gdje, kod svake skupine =NR7NC, ukoliko je prisutna, R7NCse neovisno bira od:
-H;
nesupstituiranog alifatskog C1-6alkila; supstituiranog alifatskog C1-6alkila;
nesupstituiranog alifatskog C2-6alkenila; supstituiranog alifatskog C2-6alkenila;
nesupstituiranog C3-6Cikloalkila; supstituiranog C3-6cikloalkila;
nesupstituiranog C6-10karboarila; supstituiranog C6-10karboarila;
nesupstituiranog C5-10heteroarila; supstituiranog C5-10heteroarila;
nesupstituiranog C6-10karboarila-C1-4alkila; supstituiranog C6-10karboarila-C1-4alkila;
i gdje je RN10, ukoliko je prisutna, neovisno se bira od:
-H;
nesupstituiranog alifatskog C1-6alkila; supstituiranog alifatskog C1-6alkila;
nesupstituiranog alifatskog C2-6alkenila; supstituiranog alifatskog C2-6alkenila;
nesupstituiranog C3-6cikloalkila; supstituiranog C3-6cikloalkila;
nesupstituiranog C6-10karboarila; supstituiranog C6-10karboarila;
nesupstituiranog C5-10heteroarila; supstituiranog C5-10heteroarila;
nesupstituiranog C6-10karboarila-C1-4alkila; supstituiranog C6-10karboarila-C1-4al kila;
i gdje X-, ukoliko je prisutan, je jedan ili više anionskih suprotnih iona kako bi se postigla električna neutralnost;
i njihove farmaceutski prihvatljive soli, miješane soli, hidrati i solvati.
2. Uporaba prema patentnom zahtjevu 1, naznačena time, da se svaki od R1, R2, R4, R6, R8, i R9 neovisno biraju od:
-H;
-R.
3. Uporaba prema patentnom zahtjevu 1 ili patentnom zahtjevu 2, naznačena time, da se svaki R neovisno bira od:
nesupstituiranog alifatskog C1-6alkila; supstituiranog alifatskog C1-6alkila.
4. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 3, naznačena time, da se supstituenti na R, ako su prisutni, neovisno biraju od:
- F; -Cl; -Br; -I;
- OH; -OR;
- C(=O)OH; -C(=O)OR';
- R'
gdje se svaki R' neovisno bira od:
nesupstituiranog alifatskog C1-6alkila;
nesupstituiranog alifatskog C2-6alkenila;
nesupstituiranog C3-6 cikloalkila;
nesupstituiranog C6-10 karboarila;
nesupstituiranog C5-10 heteroarila;
nesupstituiranog C6-10 karboaril- C1-4alkila.
5. Uporaba prema patentnom zahtjevu 1, naznačena time, da se svaki od R1, R2, R4, R6, R8, i R9 neovisno biraju od: -H, -Me, -Et, -nPr, i iPr.
6. Uporaba prema patentnom zahtjevu 1, naznačena time, da se svaki od R1, R2, R4, R6, R8, i R9 neovisno biraju od: -H i -Me.
7. Uporaba prema patentnom zahtjevu 1, naznačena time, da je svaki od R1, R2, R4, R6, R8, i R9 i -H.
8. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 7, naznačena time, da se u svakoj skupini -NR3NAR3NB, ukoliko je prisutna, svaka pojedina R3NA i R3NB neovisno bira od: -H, -Me, -Et, -nPr, i iPr.
9. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 7, naznačena time, da se u svakoj skupini -NR3NAR3NB, ukoliko je prisutna, svaka pojedina R3NA i R3NB neovisno bira od: -H, -Me.
10. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 7, naznačena time, da se u svakoj skupini =NR3NC, ukoliko je prisutna, svaka pojedina R3NC neovisno bira od: -H, -Me, -Et, -nPr, i iPr.
11. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 10, naznačena time, da se u svakoj skupini = NR3NC, ukoliko je prisutna, R3NC neovisno bira od: - H i -Me.
12. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 11, naznačena time, da se u svakoj skupini -NR7NAR7NB, ukoliko je prisutna, svaka pojedina R7NA i R7NB neovisno bira od: -H, -Me, -Et, -nPr, i iPr.
13. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 11, naznačena time, da se u svakoj skupini -NR7NAR7NB, ukoliko je prisutna, svaka pojedina R7NA i R7NB neovisno bira od: -H i -Me.
14. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 11, naznačena time, da se u svakoj skupini =NR7NC, ukoliko je prisutna, R7NC neovisno bira od: - H, -Me, -Et, -nPr, i iPr.
15. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 11, naznačena time, da se u svakoj skupini =NR7NC, ukoliko je prisutna, R7NC neovisno bira od: - H i -Me.
16. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 15, naznačena time, da se RN10, ukoliko je prisutna, neovisno bira od: -H, -Me i -Et.
17. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 15, naznačena time, da je RN10, ukoliko je prisutna, neovisno -H.
18. Uporaba prema bilo kojem od patentnih zahtjeva 1 do 17, naznačena time, da je X-, ukoliko je prisutan, jedan ili više anionskih suprotnih iona kako bi se postigla električna neutralnost, opcionalno se bira od Cl-, Br-, ili I-.
19. Uporaba prema patentnom zahtjevu 1, naznačena time, da se spoj bira od slijedećih spojeva, i njegovih farmaceutski prihvatljivih soli, miješanih soli, i solvata:
20. Diaminofenotiazinski spoj kako je opisan u bilo kojem od patentnih zahtjeva 1 do 19, naznačen time, da je za uporabu u postupku liječenja blagog kognitivnog poremećaja (BKP) kod pacijenta koji od njega boluje, koji postupak uključuje primjenu učinkovite količine navedenog diaminofenotiazinskog spoja.
21. Uporaba ili spoj za uporabu prema bilo kojem od patentnih zahtjeva 1 do 20, naznačeni time, da je BKP amnestički i liječenje je za simptomatsko olakšavanje putem ublaživanja amnestičkih simptoma.
22. Uporaba ili spoj za uporabu prema bilo kojem od patentnih zahtjeva 1 do 21, naznačeni time, da se navedeni pacijent bira iz skupine koja se sastoji od:
(i) pacijenata koji nemaju dijagnosticiranu Alzheimerovu bolest i\ili nisu dementni;
(ii) pacijenata koji imaju rezultat testa za ispitivanje mentalnog statusa MMSE (prema engl. Mini-Mental State Examination) manje ili jednako 24, 25, 26, 27, 28 ili 29; i
(iii) pacijenata koji ne boluju od manjkavosti u energetskom metabolizmu mitohondrija.
23. Uporaba ili spoj za uporabu prema bilo kojem od patentnih zahtjeva 1 do 22, naznačeni time, da navedeno liječenje obuhvaća primjenu navedenog diaminofenotiazinskog spoja u kombinaciji s kolinergičkim lijekom koji bilo:
(i) pojačava ili oponaša djelovanje acetilkolina, ili
(ii) je inhibitor kolinesteraze.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94500607P | 2007-06-19 | 2007-06-19 | |
| EP08762390.6A EP2167095B1 (en) | 2007-06-19 | 2008-06-17 | Phenothiazine compounds for treating mild cognitive impairment |
| PCT/GB2008/002066 WO2008155533A2 (en) | 2007-06-19 | 2008-06-17 | Phenothiazine compounds for treating mild cognitive impairment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20191513T1 true HRP20191513T1 (hr) | 2019-11-29 |
Family
ID=39943003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20191513 HRP20191513T1 (hr) | 2007-06-19 | 2019-08-21 | Fenotiazinski spojevi za liječenje blagog kognitivnog poremećaja |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9211294B2 (hr) |
| EP (1) | EP2167095B1 (hr) |
| JP (1) | JP5725605B2 (hr) |
| CN (1) | CN101820884B (hr) |
| AU (1) | AU2008265045B2 (hr) |
| BR (1) | BRPI0813670A2 (hr) |
| CA (1) | CA2690746C (hr) |
| DK (1) | DK2167095T3 (hr) |
| ES (1) | ES2739546T3 (hr) |
| HR (1) | HRP20191513T1 (hr) |
| HU (1) | HUE045460T2 (hr) |
| MY (1) | MY177001A (hr) |
| PL (1) | PL2167095T3 (hr) |
| PT (1) | PT2167095T (hr) |
| SI (1) | SI2167095T1 (hr) |
| WO (1) | WO2008155533A2 (hr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119294B (zh) | 2006-03-29 | 2018-10-30 | 维斯塔实验室有限公司 | 3,7-二氨基-10h-吩噻嗪化合物的制备方法 |
| EP2954932B1 (en) * | 2007-10-03 | 2018-09-19 | WisTa Laboratories Ltd. | Therapeutic use of diaminophenothiazines |
| WO2011137447A1 (en) | 2010-04-30 | 2011-11-03 | Prostetta Antiviral Inc. | Antiviral compounds |
| US8828986B2 (en) | 2011-04-20 | 2014-09-09 | Prosetta Antiviral Inc. | Antiviral compounds |
| SI2673266T1 (sl) * | 2011-02-11 | 2016-11-30 | Wista Laboratories Ltd. | Fenotiazin diaminijeve soli in njihova uporaba |
| CN104955800B (zh) * | 2013-01-30 | 2018-11-06 | 艺康美国股份有限公司 | 硫化氢清除剂 |
| US10304006B2 (en) * | 2013-02-15 | 2019-05-28 | The Charles Stark Draper Laboratory, Inc. | Method for integrating and fusing heterogeneous data types to perform predictive analysis |
| AU2016220096B2 (en) * | 2015-02-17 | 2020-01-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Phenothiazine analogues as mitochondrial therapeutic agents |
| MY201804A (en) * | 2016-07-25 | 2024-03-19 | Wista Laboratories Ltd | Administration and dosage of diaminophenothiazines |
| GB201614834D0 (en) * | 2016-09-01 | 2016-10-19 | Wista Lab Ltd | Treatment of dementia |
| CA3134588A1 (en) * | 2019-04-10 | 2020-10-15 | Genting Taurx Diagnostic Centre Sdn Bhd | Adaptive neurological testing method |
| GB201909493D0 (en) | 2019-07-01 | 2019-08-14 | Wista Lab Ltd | Therapeutic interactions |
| GB201909454D0 (en) | 2019-07-01 | 2019-08-14 | Wista Lab Ltd | Enhancers |
| GB201909506D0 (en) | 2019-07-02 | 2019-08-14 | Wista Lab Ltd | Synaptopathies |
| WO2023232764A1 (en) | 2022-05-31 | 2023-12-07 | Wista Laboratories Ltd. | Treatment of neurodegenerative disorders utilising methylthioninium (mt)-containing compounds |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9506197D0 (en) * | 1995-03-27 | 1995-05-17 | Hoffmann La Roche | Inhibition of tau-tau association. |
| GB0017060D0 (en) * | 2000-07-11 | 2000-08-30 | Hunter Fleming Ltd | Production, stabilisation and use of reduced forms of pharmaceutical compounds |
| GB0101049D0 (en) * | 2001-01-15 | 2001-02-28 | Univ Aberdeen | Materials and methods relating to protein aggregation in neurodegenerative disease |
| US20070037848A1 (en) * | 2003-04-03 | 2007-02-15 | Masters Colin L | Treatment of neurological conditions |
| JP5186212B2 (ja) * | 2004-09-23 | 2013-04-17 | ウィスタ ラボラトリーズ リミテッド | メチルチオニニウム塩化物（ｍｔｃ）などのジアミノフェノチアジニウム化合物を化学合成および精製する方法 |
| WO2006032879A2 (en) | 2004-09-23 | 2006-03-30 | Wista Laboratories Ltd. | Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (mtc) |
| WO2006091728A2 (en) * | 2005-02-24 | 2006-08-31 | The Trustees Of The University Of Pennsylvania | Microtubule stabilizing compounds and methods of their use |
| CN101460222B (zh) * | 2006-03-29 | 2013-12-04 | 维斯塔实验室有限公司 | 锍化合物及其用途 |
| CN104119294B (zh) * | 2006-03-29 | 2018-10-30 | 维斯塔实验室有限公司 | 3,7-二氨基-10h-吩噻嗪化合物的制备方法 |
| CN103735554B (zh) * | 2006-03-29 | 2018-03-20 | 维斯塔实验室有限公司 | 蛋白聚集抑制剂 |
| CN101511803B (zh) * | 2006-07-11 | 2012-10-31 | 维斯塔实验室有限公司 | 二氨基吩噻嗪*化合物的合成和/或纯化方法 |
-
2008
- 2008-06-17 SI SI200832080T patent/SI2167095T1/sl unknown
- 2008-06-17 DK DK08762390.6T patent/DK2167095T3/da active
- 2008-06-17 BR BRPI0813670-0A2A patent/BRPI0813670A2/pt not_active Application Discontinuation
- 2008-06-17 WO PCT/GB2008/002066 patent/WO2008155533A2/en active Application Filing
- 2008-06-17 CN CN2008801031955A patent/CN101820884B/zh active Active
- 2008-06-17 PL PL08762390T patent/PL2167095T3/pl unknown
- 2008-06-17 ES ES08762390T patent/ES2739546T3/es active Active
- 2008-06-17 AU AU2008265045A patent/AU2008265045B2/en active Active
- 2008-06-17 MY MYPI20095255A patent/MY177001A/en unknown
- 2008-06-17 JP JP2010512761A patent/JP5725605B2/ja active Active
- 2008-06-17 EP EP08762390.6A patent/EP2167095B1/en active Active
- 2008-06-17 PT PT08762390T patent/PT2167095T/pt unknown
- 2008-06-17 HU HUE08762390A patent/HUE045460T2/hu unknown
- 2008-06-17 US US12/665,608 patent/US9211294B2/en active Active
- 2008-06-17 CA CA2690746A patent/CA2690746C/en active Active
-
2019
- 2019-08-21 HR HRP20191513 patent/HRP20191513T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2690746A1 (en) | 2008-12-24 |
| ES2739546T3 (es) | 2020-01-31 |
| SI2167095T1 (sl) | 2019-09-30 |
| JP2010530403A (ja) | 2010-09-09 |
| WO2008155533A3 (en) | 2009-02-19 |
| EP2167095A2 (en) | 2010-03-31 |
| CN101820884A (zh) | 2010-09-01 |
| DK2167095T3 (da) | 2019-07-29 |
| US9211294B2 (en) | 2015-12-15 |
| BRPI0813670A2 (pt) | 2014-12-30 |
| PL2167095T3 (pl) | 2019-11-29 |
| AU2008265045B2 (en) | 2014-02-27 |
| EP2167095B1 (en) | 2019-05-29 |
| WO2008155533A2 (en) | 2008-12-24 |
| AU2008265045A1 (en) | 2008-12-24 |
| MY177001A (en) | 2020-09-01 |
| CN101820884B (zh) | 2013-08-28 |
| US20100184752A1 (en) | 2010-07-22 |
| HUE045460T2 (hu) | 2019-12-30 |
| PT2167095T (pt) | 2019-08-06 |
| JP5725605B2 (ja) | 2015-05-27 |
| CA2690746C (en) | 2018-01-02 |
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