ZA200608123B - Combinations of glycopyrrolate and beta2 adrenoceptor agonists - Google Patents

Combinations of glycopyrrolate and beta2 adrenoceptor agonists Download PDF

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Publication number: ZA200608123B
Authority: ZA; South Africa
Prior art keywords: cio; hydroxy; alkyl; alkoxy; optionally substituted
Prior art date: 2004-05-18

Application number

ZA200608123A

Other languages

English (en)

Inventor

Collingwood Stephen Paul

Original Assignee

Novartisag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-05-18

Filing date

2006-09-29

Publication date

2008-07-30

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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32607514&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200608123(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-09-29 Application filed by Novartisag filed Critical Novartisag

2008-07-30 Publication of ZA200608123B publication Critical patent/ZA200608123B/en

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VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 title claims description 13
229940015042 glycopyrrolate Drugs 0.000 title claims description 12
239000000556 agonist Substances 0.000 title description 6
102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 title description 5
108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 title description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
239000003814 drug Substances 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 34
125000005843 halogen group Chemical group 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 29
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000000843 powder Substances 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 25
239000000443 aerosol Substances 0.000 claims description 23
-1 cyano, hydroxy Chemical group 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000000623 heterocyclic group Chemical group 0.000 claims description 22
239000006185 dispersion Substances 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
239000003380 propellant Substances 0.000 claims description 14
150000003839 salts Chemical group 0.000 claims description 12
239000002775 capsule Substances 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
230000002757 inflammatory effect Effects 0.000 claims description 9
239000012453 solvate Chemical group 0.000 claims description 9
208000027771 Obstructive airways disease Diseases 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
208000027866 inflammatory disease Diseases 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000002245 particle Substances 0.000 claims description 7
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
239000000739 antihistaminic agent Substances 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
238000002648 combination therapy Methods 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
GTTZQULJQRNNER-HNNXBMFYSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[(2-methyl-1-phenylpropan-2-yl)amino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NC(C)(C)CC1=CC=CC=C1 GTTZQULJQRNNER-HNNXBMFYSA-N 0.000 claims description 2
ONNGKMAEIWXVBI-UHFFFAOYSA-N 4-hydroxy-7-[1-hydroxy-2-[2-[4-(4-phenylbutoxy)phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C=1C=C(O)C=2NC(=O)SC=2C=1C(O)CNCCC(C=C1)=CC=C1OCCCCC1=CC=CC=C1 ONNGKMAEIWXVBI-UHFFFAOYSA-N 0.000 claims description 2
AUUXBAOWHVOGFM-FTBISJDPSA-N 5-[(1r)-2-[(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one;hydrochloride Chemical compound Cl.N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 AUUXBAOWHVOGFM-FTBISJDPSA-N 0.000 claims description 2
LKKKXVXXRSMKJD-UHFFFAOYSA-N 5-[2-[(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)amino]-1-hydroxyethyl]-8-(methoxymethoxy)-6-methyl-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C(OCOC)=CC(C)=C2C(O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 LKKKXVXXRSMKJD-UHFFFAOYSA-N 0.000 claims description 2
IAYCRMOPCKGMOQ-UHFFFAOYSA-N 5-[2-[(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-6-methyl-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C(O)=CC(C)=C2C(O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 IAYCRMOPCKGMOQ-UHFFFAOYSA-N 0.000 claims description 2
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 2
230000001387 anti-histamine Effects 0.000 claims description 2
230000003110 anti-inflammatory effect Effects 0.000 claims description 2
239000003434 antitussive agent Substances 0.000 claims description 2
229940124584 antitussives Drugs 0.000 claims description 2
239000004067 bulking agent Substances 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000006184 cosolvent Substances 0.000 claims description 2
239000000850 decongestant Substances 0.000 claims description 2
ZEXCGJJNMGJWDF-FERBBOLQSA-N formic acid;4-hydroxy-7-[(1r)-1-hydroxy-2-[2-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound OC=O.C1([C@H](CNCCC=2C=C3CCCCC3=CC=2)O)=CC=C(O)C2=C1SC(=O)N2 ZEXCGJJNMGJWDF-FERBBOLQSA-N 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
IREJFXIHXRZFER-PCBAQXHCSA-N indacaterol maleate Chemical compound OC(=O)\C=C/C(O)=O.N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 IREJFXIHXRZFER-PCBAQXHCSA-N 0.000 claims description 2
150000002688 maleic acid derivatives Chemical class 0.000 claims description 2
229940071648 metered dose inhaler Drugs 0.000 claims description 2
125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 11
QTWVYUJFBIVOHT-RYQLBKOJSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[[(1s,2r)-2-phenylmethoxycyclopentyl]amino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound O([C@@H]1CCC[C@@H]1NC[C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)CC1=CC=CC=C1 QTWVYUJFBIVOHT-RYQLBKOJSA-N 0.000 claims 1
QTWVYUJFBIVOHT-SZMVWBNQSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[[(1s,2s)-2-phenylmethoxycyclopentyl]amino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound O([C@H]1CCC[C@@H]1NC[C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)CC1=CC=CC=C1 QTWVYUJFBIVOHT-SZMVWBNQSA-N 0.000 claims 1
LNWINKMRDGCDER-UHFFFAOYSA-N 5-[2-[(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-3-methyl-1h-quinolin-2-one Chemical compound N1C(=O)C(C)=CC2=C1C(O)=CC=C2C(O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 LNWINKMRDGCDER-UHFFFAOYSA-N 0.000 claims 1
ZQWNZUAMWNPQGR-UHFFFAOYSA-N 5-[2-[(5,6-diethyl-2,3-dihydro-1h-inden-2-yl)amino]ethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2CCNC1CC(C=C(C(=C2)CC)CC)=C2C1 ZQWNZUAMWNPQGR-UHFFFAOYSA-N 0.000 claims 1
XRZOULQZLDILQH-UHFFFAOYSA-N 5-[2-[(5,6-dimethoxy-2,3-dihydro-1h-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2C(O)CNC1CC(C=C(C(=C2)OC)OC)=C2C1 XRZOULQZLDILQH-UHFFFAOYSA-N 0.000 claims 1
MXCGESVXTRYGMG-SFHVURJKSA-N 8-hydroxy-5-[(1r)-1-hydroxy-2-[(2-methyl-1,3-dihydroinden-2-yl)amino]ethyl]-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1(C)CC2=CC=CC=C2C1 MXCGESVXTRYGMG-SFHVURJKSA-N 0.000 claims 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
239000008186 active pharmaceutical agent Substances 0.000 claims 1
208000006673 asthma Diseases 0.000 claims 1
229940124630 bronchodilator Drugs 0.000 claims 1
239000002552 dosage form Substances 0.000 claims 1
229940088679 drug related substance Drugs 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
239000004480 active ingredient Substances 0.000 description 12
239000005557 antagonist Substances 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
150000002430 hydrocarbons Chemical group 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
238000000034 method Methods 0.000 description 6
239000006199 nebulizer Substances 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
125000005330 8 membered heterocyclic group Chemical group 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
239000008101 lactose Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
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 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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125000000217 alkyl group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
150000003842 bromide salts Chemical class 0.000 description 3
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229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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Classifications

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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
- 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
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/402—1-aryl substituted, e.g. piretanide
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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Publication number	Publication date
CN1953745A (zh)	2007-04-25
CY2020013I2 (el)	2020-11-25
NO2014020I2 (pt)	2014-08-07
LT2228064T (lt)	2020-03-25
KR101360556B9 (ko)	2022-08-12
MA28598B1 (fr)	2007-05-02
IL179013A0 (en)	2007-05-15
HUS1400013I1 (hu)	2016-11-28
LTPA2014015I1 (lt)	2014-04-25
EP1755590A1 (en)	2007-02-28
BRPI0511327A (pt)	2007-12-04
AU2005244439C1 (en)	2014-09-11
FR20C1018I2 (fr)	2023-11-03
NO2014020I1 (no)	2014-08-07
JP5567252B2 (ja)	2014-08-06
CY2014014I1 (el)	2015-11-04
NO20065787L (no)	2006-12-14
US20160101097A1 (en)	2016-04-14
SI2228064T1 (sl)	2020-04-30
DK1755590T3 (da)	2011-12-12
ATE521348T1 (de)	2011-09-15
ES2775979T3 (es)	2020-07-28
FR20C1018I1 (fr)	2020-07-10
NZ550369A (en)	2009-11-27
HK1105579A1 (en)	2008-02-22
RU2006144810A (ru)	2008-06-27
JP2007538036A (ja)	2007-12-27
LUC00155I1 (pt)	2020-05-27
ES2370647T3 (es)	2011-12-21
PL1755590T3 (pl)	2012-01-31
KR20070011519A (ko)	2007-01-24
AU2005244439B2 (en)	2009-07-30
RU2388465C2 (ru)	2010-05-10
PL2228064T3 (pl)	2020-06-01
HUE048936T2 (hu)	2020-09-28
KR20130018429A (ko)	2013-02-21
SE1755590T5 (pt)	2015-01-20
EP2228064A3 (en)	2011-11-02
US20190282561A1 (en)	2019-09-19
AU2005244439A1 (en)	2005-11-24
LTPA2020509I1 (lt)	2020-07-10
JP2012236833A (ja)	2012-12-06
HUS2000014I1 (hu)	2020-07-28
CY2020013I1 (el)	2020-11-25
CY1122863T1 (el)	2020-11-25
PT1755590E (pt)	2011-10-27
EP1755590B1 (en)	2011-08-24
NO334760B1 (no)	2014-05-19
EP2228064A2 (en)	2010-09-15
PT2228064T (pt)	2020-08-25
CY1112086T1 (el)	2015-11-04
LTC1755590I2 (lt)	2018-05-10
MXPA06013382A (es)	2007-03-23
TNSN06377A1 (en)	2008-02-22
CA2563302C (en)	2012-08-28
DK2228064T3 (da)	2020-03-16
GB0411056D0 (en)	2004-06-23
ECSP066950A (es)	2006-12-20
CA2563302A1 (en)	2005-11-24
EP3603634A1 (en)	2020-02-05
SG153836A1 (en)	2009-07-29
US20210236478A1 (en)	2021-08-05
US20080267886A1 (en)	2008-10-30
SI1755590T1 (sl)	2011-12-30
BRPI0511327B8 (pt)	2021-05-25
EP2228064B1 (en)	2019-12-11
IL179013A (en)	2012-02-29
KR101360556B1 (ko)	2014-02-21
US20130237564A1 (en)	2013-09-12
US20180071276A1 (en)	2018-03-15
WO2005110402A1 (en)	2005-11-24
LTC2228064I2 (lt)	2022-05-10
BE2020C517I2 (pt)	2024-08-08
BRPI0511327B1 (pt)	2019-08-06
EP3603634B1 (en)	2025-02-12
LUC00155I2 (pt)	2021-02-17

Publication	Publication Date	Title
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