HRP20120857T1 - Derivati 4-(n-azacikloalkil) anilida kao modulatori kalijevog kanala - Google Patents
Derivati 4-(n-azacikloalkil) anilida kao modulatori kalijevog kanala Download PDFInfo
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- HRP20120857T1 HRP20120857T1 HRP20120857AT HRP20120857T HRP20120857T1 HR P20120857 T1 HRP20120857 T1 HR P20120857T1 HR P20120857A T HRP20120857A T HR P20120857AT HR P20120857 T HRP20120857 T HR P20120857T HR P20120857 T1 HRP20120857 T1 HR P20120857T1
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- Prior art keywords
- alkyl
- cycloalkyl
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- 102000004257 Potassium Channel Human genes 0.000 title claims 2
- 108020001213 potassium channel Proteins 0.000 title claims 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title 1
- 150000003931 anilides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- -1 cyano, methyl Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000005412 pyrazyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Claims (16)
1. Spoj formule I
[image]
naznačen time, da najmanje jedan od W i Z jeste N;
pri čemu ostatak dolje je jedna od skupina A ili B
[image]
A
[image]
gdje Ar jeste 1,2-spojeni, šestero-člani prsten aromatske skupine, koji nosi supstituente R1 i R2 kako je dolje definirano i sadrži nula ili jedan prsten dušikovog atoma;
B
[image]
gdje je Ar 1,2-spojeni, šestero-člani prsten aromatske skupine, koji nosi supstituente R1 i R2 kako je dolje definirano i sadžri nula ili jedan presten dušikovog atoma; pri čmeu su R1 i R2, neovisno, H, CN, halogen, CH2CN, OH, NO2, CH2F, CHF2, CF3, CF2CF3, C1-C6 alkil, C(=O)C1-C6 alkil, NH-C1-C6 alkil, NHC(=O)C1-C6 alkil, C(=O)N(CH3)2, C(=O)N(Et)2, C(=O)NH- C1-C6alkil, C(=O)OC1-C6 alkil,OC(=O)C1-C6 alkil, OC1-C6 alkil, SC1-C6 alkil, C3-C6cikloalkil, (CH2)mC3-C6cikloalkil, C3-C6 cikloalkenil, (CH2)mC3-C6 cikloalkenil, C2-C6 alkenil, C2-C6 alkinil, Ar1, (CH2)mAr1, fenil, piridil, pirolil, (CH2)mimidazolil, (CH2)mpirazil, furil, tienil, (CH2)moksazolil, (CH2)misoksazolil, (CH2)mtiazolil, (CH2)mizotiazolil, (CH2)mfenil, (CH2)mpirolil, (CH2)mpiridil, ili (CH2)mpirimidil, koje skupine cikloalkila i rečenog cikloalkenila po izboru sadrže jedan ili dva heteroatoma neovisno odabrana od O, N i S, i koje skupine alkila, cikloalkila, cikloalkenila, alkenila, alkinila, imidazolila, pirazila, oksazolila, izoksazolila, tiazolila, izotiazolila, fenila, pirolila, piridila ili pirimidila su po izboru supstituirane s jednom ili dvije skupine neovisno odabrane od OH, halogena, cijano, metila, etila ili trifluorometila, pri čemu je m nula, 1 ili 2;
ili R1 i R2, zajedno s prstenom ugljikovih atoma za kojeg su vezani tvore 5- ili 6-člani spojeni prsten, gdje prsten može biti zasićen ili nezasićen ili aromatski, koji po izboru sadrži jedan ili dva heteroatoma neovisno odabrana od O, N i S i koji je po izboru supstituiran s halogenom, CF3 ili C1-C3 alkil;
R1 je H, halogen, CF3 ili C1-C3 alkil;
R3 i R4 su, neovisno, H, CN, halogen, CF3, OCF3, O C1-C3 alkil, ili C1-C6 alkil, sve rečene C1-C3 alkilne skupine i rečene C1-C6 alkilne skupine po izboru supstituirane s jednom ili dvije skupine odabrane, neovisno, od OH, halogena, C1-C3 alkila, OC1-C3 alkila ili trifluorometila;
X = O ili S;
Y je O ili S; q = 1 ili 0;
R5 je C1-C6 alkil, (CHR6)wC3-C6 cikloalkil, (CHR6)wCH2 C3-C6 cikloalkil, CH2(CHR6)wC3-C6 cikloalkil, CR6=CH-C3-C6 cikloalkil, CH=CR6-C3-C6 cikloalkil, (CHR6)wC5-C6 cikloalkenil, CH2(CHR6)wC5-C6 cikloalkenil, C2-C6 alkenil, C2-C6 alkinil, Ar1, (CHR6)wAr1, CH2(CHR6)wAr1 ili (CHR6)wCH2Ar1,
Pri čemu je w = 0 - 3, Ar1 je 5-etero do 10-člana mono- ili biciklička aromatska skupina koja po izboru može sadržati 1 - 4 prstenasta heteroatoma neovisno odabrana od N, O i S;
R6 je vodik ili C1-C3 alkil;
gdje sve cikloalkilne i cikloalkenilne skupine po izboru mogu sadržavati jedan ili dva prstenasta heteroatoma neovisno odabrana od N, O i S; gdje su sve alkilne, cikloalkilne, alkenilne, cikloalkenilne, heterocikloalkilne, heterocikloalkenilne, alkinilne, arilne i heteroarilne skupine u R1, R2, R3, R4, R5, R6 ili Ar1 po izboru susptituirane s jednim ili dva supstituenta neovisno odabrana od C1-C3 alkila, halogena, OH, OMe, SMe, CN, CH2F i trifluorometila; gdje, dodatno, su sve cikloalkilne i heterocikloalkilne po izboru supstituirane ilis egzocikličkim ugljik-ugljik dvostrukom vezom ili karbonilnom skupinom; te pri čemu su, dodatno, alkenilne i alkinilne skupine također po izboru supstituirane s fenilom ili C3-C6 cikloalkilom; i njihove farmaceutski prihvatljive soli.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da je skupina
[image]
[image]
3. Spoj u skladu s patentnim zahtjevom 2, naznačen time, da je isti spoj formule IA-1
[image]
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time, da je isti spoj formule IA-1a ili IA-1b:
[image]
5. Spoj u skladu s patentnim zahtjevom 2, naznačen time, da je spoj formule IA2, IA3, IA4 ili IA5:
[image]
[image]
6. Spoj u skladu s patentnim zahtjevom 5, naznačen time, da X je O, Y je O, a q je 0 ili 1.
7. Spoj u skladu s patentnim zahtjevom 4 ili 6, naznačen time, da su R3 i R4 neovisno, H, halogen, metil, metoksi ili trifluorometil.
8. Spoj u skladu s patentnim zahtjevom 7, naznačen time, da su R1 i R2 neovisno, H, halogen, metil ili trifluorometil.
9. Spoj u skladu s patentnim zahtjevom 8, naznačen time, da je R5 C3-C6 alkil ili CH2-C3-C6-cikloalkil, a pri čemu je R5 po izboru supstituiran s halogenenom, hidroksi ili metoksi.
10. Spoj u skladu s patentnim zahtjevom 9, naznačen time, da je R1 H, F, metil ili trifluorometil.
11. Spoj u skladu s patentnim zahtjevom 10, naznačen time, gdje oba W i Z jesu N.
12. Spoj u skladu s patentnim zahtjevom 10, naznačen time, da jedan od W i Z jeste N a drugi je C.
13. Spoj u skladu s patentnim zahtjevom 11 ili zahtjevom 12, naznačen time, da su R3 i R4, neovisno, H, metil ili metoksi.
14. Farmaceutski pripravak, naznačen time, da sadrži spoj formule I u skladu s patentnim zahtjevom 1 s farmaceutski prihvatljivim nosačem.
15. Spoj formule I u skladu s patentnim zahtjevom 1 ili njegova sol ili ester, naznačen time, da je za prevenciju ili liječenje bolesti ili poremećaja koji su izazvani djelovanjem kalijevih kanala.
16. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da ima strukturnu formulu:
[image]
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US93439607P | 2007-06-13 | 2007-06-13 | |
US12/138,251 US8367684B2 (en) | 2007-06-13 | 2008-06-12 | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
PCT/US2008/066984 WO2008157404A2 (en) | 2007-06-13 | 2008-06-13 | Derivatives of 4-(n-azacycloalkyl) anilides as potassium channel modulators |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20120857T1 true HRP20120857T1 (hr) | 2012-11-30 |
Family
ID=40137141
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20120857AT HRP20120857T1 (hr) | 2007-06-13 | 2012-10-23 | Derivati 4-(n-azacikloalkil) anilida kao modulatori kalijevog kanala |
Country Status (18)
Country | Link |
---|---|
US (1) | US8367684B2 (hr) |
EP (1) | EP2170861B1 (hr) |
JP (1) | JP2010530002A (hr) |
KR (1) | KR20100018618A (hr) |
CN (1) | CN101868451A (hr) |
AU (1) | AU2008266009B2 (hr) |
BR (1) | BRPI0812564A2 (hr) |
CA (1) | CA2689208A1 (hr) |
DK (1) | DK2170861T3 (hr) |
ES (1) | ES2392774T3 (hr) |
HR (1) | HRP20120857T1 (hr) |
MX (1) | MX2009013581A (hr) |
PL (1) | PL2170861T3 (hr) |
PT (1) | PT2170861E (hr) |
RU (1) | RU2010100893A (hr) |
SI (1) | SI2170861T1 (hr) |
TW (1) | TW200914452A (hr) |
WO (1) | WO2008157404A2 (hr) |
Families Citing this family (10)
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US8563566B2 (en) * | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
US7786146B2 (en) * | 2007-08-13 | 2010-08-31 | Valeant Pharmaceuticals International | Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators |
WO2010122064A1 (en) | 2009-04-21 | 2010-10-28 | Neurosearch A/S | Substituted naphthyridine derivatives and their medical use |
EP2590961A1 (en) * | 2010-07-08 | 2013-05-15 | Pfizer Inc | Piperidinyl pyrimidine amides as kv7 potassium channel openers |
US9309221B2 (en) | 2012-04-10 | 2016-04-12 | Sumitomo Dainippon Pharma Co., Ltd. | 1-substituted indazole derivative |
CN108250128A (zh) * | 2012-09-27 | 2018-07-06 | 江苏先声药业有限公司 | 作为钾通道调节剂的化合物 |
AU2015401762B2 (en) | 2015-07-07 | 2019-03-14 | Colgate-Palmolive Company | Oral care implement and monofilament bristle for use with the same |
CN110511220B (zh) * | 2018-05-22 | 2022-04-01 | 上海挚盟医药科技有限公司 | 作为钾通道调节剂的对二氨基苯衍生物、其制备方法及其在医药上的应用 |
TW202333693A (zh) * | 2021-12-31 | 2023-09-01 | 大陸商上海翰森生物醫藥科技有限公司 | 苯并哌啶衍生物調節劑、其製備方法和應用 |
CN116535353A (zh) * | 2022-01-25 | 2023-08-04 | 上海挚盟医药科技有限公司 | 作为钾通道调节剂的酰胺类化合物及其制备和应用 |
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-
2008
- 2008-06-12 US US12/138,251 patent/US8367684B2/en active Active
- 2008-06-13 EP EP08771077A patent/EP2170861B1/en not_active Not-in-force
- 2008-06-13 MX MX2009013581A patent/MX2009013581A/es active IP Right Grant
- 2008-06-13 CN CN200880102338A patent/CN101868451A/zh active Pending
- 2008-06-13 DK DK08771077.8T patent/DK2170861T3/da active
- 2008-06-13 WO PCT/US2008/066984 patent/WO2008157404A2/en active Application Filing
- 2008-06-13 BR BRPI0812564-3A2A patent/BRPI0812564A2/pt not_active Application Discontinuation
- 2008-06-13 KR KR1020107000706A patent/KR20100018618A/ko not_active Application Discontinuation
- 2008-06-13 JP JP2010512399A patent/JP2010530002A/ja active Pending
- 2008-06-13 SI SI200830745T patent/SI2170861T1/sl unknown
- 2008-06-13 ES ES08771077T patent/ES2392774T3/es active Active
- 2008-06-13 AU AU2008266009A patent/AU2008266009B2/en not_active Ceased
- 2008-06-13 CA CA002689208A patent/CA2689208A1/en not_active Abandoned
- 2008-06-13 TW TW097122339A patent/TW200914452A/zh unknown
- 2008-06-13 PL PL08771077T patent/PL2170861T3/pl unknown
- 2008-06-13 RU RU2010100893/04A patent/RU2010100893A/ru not_active Application Discontinuation
- 2008-06-13 PT PT08771077T patent/PT2170861E/pt unknown
-
2012
- 2012-10-23 HR HRP20120857AT patent/HRP20120857T1/hr unknown
Also Published As
Publication number | Publication date |
---|---|
WO2008157404A2 (en) | 2008-12-24 |
EP2170861B1 (en) | 2012-08-29 |
ES2392774T3 (es) | 2012-12-13 |
KR20100018618A (ko) | 2010-02-17 |
RU2010100893A (ru) | 2011-07-20 |
CN101868451A (zh) | 2010-10-20 |
JP2010530002A (ja) | 2010-09-02 |
US20080318979A1 (en) | 2008-12-25 |
DK2170861T3 (da) | 2012-11-26 |
TW200914452A (en) | 2009-04-01 |
BRPI0812564A2 (pt) | 2015-02-10 |
PT2170861E (pt) | 2012-09-06 |
PL2170861T3 (pl) | 2013-01-31 |
AU2008266009A1 (en) | 2008-12-24 |
AU2008266009B2 (en) | 2013-06-06 |
MX2009013581A (es) | 2010-01-26 |
WO2008157404A3 (en) | 2009-02-19 |
SI2170861T1 (sl) | 2012-12-31 |
US8367684B2 (en) | 2013-02-05 |
CA2689208A1 (en) | 2008-12-24 |
EP2170861A2 (en) | 2010-04-07 |
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