JP5957077B2 - タンキラーゼ阻害剤として使用するための４−ピペリジニル化合物 - Google Patents

タンキラーゼ阻害剤として使用するための４−ピペリジニル化合物 Download PDF

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Publication number: JP5957077B2
Authority: JP; Japan
Prior art keywords: piperidin; oxo; methoxy; pyrrolidin; ylmethyl
Prior art date: 2011-07-13
Legal status (The legal status 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 status listed.): Expired - Fee Related

Application number

JP2014519688A

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English (en)

Japanese (ja)

Other versions

JP2014522855A5 (2

JP2014522855A (ja

Inventor

ヒゥ−タンチェン，クリスティン

チンチン，ノエル

ブイ．ディピエトロ，ルシアン

ファン，ジアンメ

ジーパラーモ，マーク

シュルツ，マイケル，デイビッド

トゥーレ，ベーカリーバレー

Original Assignee

ノバルティスアーゲー

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.)

2011-07-13

Filing date

2012-07-13

Publication date

2016-07-27

2012-07-13 Application filed by ノバルティスアーゲー, ノバルティスアーゲー filed Critical ノバルティスアーゲー

2014-09-08 Publication of JP2014522855A publication Critical patent/JP2014522855A/ja

2015-08-06 Publication of JP2014522855A5 publication Critical patent/JP2014522855A5/ja

2016-07-27 Application granted granted Critical

2016-07-27 Publication of JP5957077B2 publication Critical patent/JP5957077B2/ja

Status Expired - Fee Related legal-status Critical Current

2032-07-13 Anticipated expiration legal-status Critical

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108010017601 Tankyrases Proteins 0.000 title description 55
239000003112 inhibitor Substances 0.000 title description 10
102000004535 Tankyrases Human genes 0.000 title description 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 192
-1 3- (4- (4-methoxybenzoyl) piperidin-1-yl) -2-oxopyrrolidin-1-yl Chemical group 0.000 claims description 86
150000003839 salts Chemical class 0.000 claims description 67
125000000217 alkyl group Chemical group 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 38
206010028980 Neoplasm Diseases 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 28
201000011510 cancer Diseases 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
239000008194 pharmaceutical composition Substances 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 17
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 14
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 12
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 7
QWYIBGOLIBASGM-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 QWYIBGOLIBASGM-UHFFFAOYSA-N 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
PADREXIRIZBNMQ-UHFFFAOYSA-N n-(5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl)-2-[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC(=O)NC=3N4CCSC4=NN=3)CC2)=O)CC1 PADREXIRIZBNMQ-UHFFFAOYSA-N 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
DDIZJESACWEABB-HXUWFJFHSA-N 2-[[(3r)-3-[4-(4-fluorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 DDIZJESACWEABB-HXUWFJFHSA-N 0.000 claims description 3
BVCFVQGPDDYTEY-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxy-3-methylbenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 BVCFVQGPDDYTEY-OAQYLSRUSA-N 0.000 claims description 3
DUCZLEBAUSAZOC-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxy-3-methylbenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-cyclohepta[d]imidazol-4-one Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC4=C(C(C=CC=C4)=O)N=3)CC2)=O)CC1 DUCZLEBAUSAZOC-OAQYLSRUSA-N 0.000 claims description 3
QWYIBGOLIBASGM-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 QWYIBGOLIBASGM-OAQYLSRUSA-N 0.000 claims description 3
FMURKSCWRQGCFO-NRFANRHFSA-N 2-[[(3s)-3-(6-methoxy-3-oxospiro[1h-indene-2,4'-piperidine]-1'-yl)-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1OCCC(N2)=C1C(=O)N=C2CN(C1=O)CC[C@@H]1N(CC1)CCC11C(=O)C2=CC=C(OC)C=C2C1 FMURKSCWRQGCFO-NRFANRHFSA-N 0.000 claims description 3
DDIZJESACWEABB-FQEVSTJZSA-N 2-[[(3s)-3-[4-(4-fluorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 DDIZJESACWEABB-FQEVSTJZSA-N 0.000 claims description 3
FMURKSCWRQGCFO-UHFFFAOYSA-N 2-[[3-(6-methoxy-3-oxospiro[1h-indene-2,4'-piperidine]-1'-yl)-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1OCCC(N2)=C1C(=O)N=C2CN(C1=O)CCC1N(CC1)CCC11C(=O)C2=CC=C(OC)C=C2C1 FMURKSCWRQGCFO-UHFFFAOYSA-N 0.000 claims description 3
LJLQEWDFIMKBSL-UHFFFAOYSA-N 2-[[3-[4-(4-chlorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 LJLQEWDFIMKBSL-UHFFFAOYSA-N 0.000 claims description 3
DDIZJESACWEABB-UHFFFAOYSA-N 2-[[3-[4-(4-fluorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 DDIZJESACWEABB-UHFFFAOYSA-N 0.000 claims description 3
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ZOLNILZRLCDHDN-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-4a,7a-dihydro-3h-thieno[3,2-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4SC=CC4N=3)CC2)=O)CC1 ZOLNILZRLCDHDN-UHFFFAOYSA-N 0.000 claims description 3
HTWNXILBIKZTTF-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(C)=C(C)C(=O)N=3)CC2)=O)CC1 HTWNXILBIKZTTF-UHFFFAOYSA-N 0.000 claims description 3
VNXUSDDWRYWPQI-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-5-methyl-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C(C)=CN=3)CC2)=O)CC1 VNXUSDDWRYWPQI-UHFFFAOYSA-N 0.000 claims description 3
TVSSLHKEVCLVAI-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-6-methyl-1h-pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(C)=CC(=O)N=3)CC2)=O)CC1 TVSSLHKEVCLVAI-UHFFFAOYSA-N 0.000 claims description 3
DVIHZULFCIMZGZ-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-6-methyl-4a,7a-dihydro-3h-thieno[2,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4C=C(C)SC4N=3)CC2)=O)CC1 DVIHZULFCIMZGZ-UHFFFAOYSA-N 0.000 claims description 3
PERWUJINIMBCAY-UHFFFAOYSA-N 2-chloro-5-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3C=C(C(Cl)=CC=3)C#N)CC2)=O)CC1 PERWUJINIMBCAY-UHFFFAOYSA-N 0.000 claims description 3
OXTYNMCLCNPCJW-UHFFFAOYSA-N 2-chloro-6-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3C(=C(Cl)C=CC=3)C#N)CC2)=O)CC1 OXTYNMCLCNPCJW-UHFFFAOYSA-N 0.000 claims description 3
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
BHLYXUCYNUOODH-UHFFFAOYSA-N 6-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1-methyl-5,7a-dihydro-3ah-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4C(N(N=C4)C)N=3)CC2)=O)CC1 BHLYXUCYNUOODH-UHFFFAOYSA-N 0.000 claims description 3
DEGIMKQHUITSSN-UHFFFAOYSA-N 6-ethyl-2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-pyrimidin-4-one Chemical compound N1C(CC)=CC(=O)N=C1CN1C(=O)C(N2CCC(CC2)C(=O)C=2C=CC(OC)=CC=2)CC1 DEGIMKQHUITSSN-UHFFFAOYSA-N 0.000 claims description 3
LWZRQSRLJJMSHR-UHFFFAOYSA-N COC1=CC=C(C=C1)C(=O)C2CCN(CC2)C3CCN(C3=O)CC4CC5CCCCC(=O)C5N4 Chemical compound COC1=CC=C(C=C1)C(=O)C2CCN(CC2)C3CCN(C3=O)CC4CC5CCCCC(=O)C5N4 LWZRQSRLJJMSHR-UHFFFAOYSA-N 0.000 claims description 3
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YUBFIWOTPFWWDX-UHFFFAOYSA-N pyrano[4,3-d]pyrimidin-4-one Chemical compound C1=COC=C2C(=O)N=CN=C21 YUBFIWOTPFWWDX-UHFFFAOYSA-N 0.000 claims description 2
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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
- A61P35/00—Antineoplastic agents
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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JP2014519688A 2011-07-13 2012-07-13 タンキラーゼ阻害剤として使用するための４−ピペリジニル化合物 Expired - Fee Related JP5957077B2 (ja)

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PCT/IB2012/053613 WO2013008217A1 (en)	2011-07-13	2012-07-13	4 - piperidinyl compounds for use as tankyrase inhibitors

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KR (1)	KR20140051944A (2)
CN (1)	CN103797006B (2)
AP (1)	AP2014007400A0 (2)
AU (1)	AU2012282076A1 (2)
BR (1)	BR112014000792A2 (2)
CA (1)	CA2841932A1 (2)
CO (1)	CO6880065A2 (2)
CR (1)	CR20140071A (2)
DO (1)	DOP2014000012A (2)
EA (1)	EA201490272A1 (2)
ES (1)	ES2548513T3 (2)
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2012
- 2012-07-13 AU AU2012282076A patent/AU2012282076A1/en not_active Abandoned
- 2012-07-13 PH PH1/2014/500126A patent/PH12014500126A1/en unknown
- 2012-07-13 US US14/154,173 patent/US9163003B2/en not_active Ceased
- 2012-07-13 CA CA 2841932 patent/CA2841932A1/en not_active Abandoned
- 2012-07-13 WO PCT/IB2012/053613 patent/WO2013008217A1/en not_active Ceased
- 2012-07-13 AP AP2014007400A patent/AP2014007400A0/xx unknown
- 2012-07-13 MX MX2014000536A patent/MX2014000536A/es not_active Application Discontinuation
- 2012-07-13 JP JP2014519688A patent/JP5957077B2/ja not_active Expired - Fee Related
- 2012-07-13 ES ES12742957.9T patent/ES2548513T3/es active Active
- 2012-07-13 BR BR112014000792A patent/BR112014000792A2/pt not_active IP Right Cessation
- 2012-07-13 CN CN201280043558.7A patent/CN103797006B/zh not_active Expired - Fee Related
- 2012-07-13 KR KR20147003628A patent/KR20140051944A/ko not_active Withdrawn
- 2012-07-13 US US15/786,125 patent/USRE46942E1/en active Active
- 2012-07-13 EA EA201490272A patent/EA201490272A1/ru unknown
- 2012-07-13 EP EP12742957.9A patent/EP2731940B1/en not_active Not-in-force
2014
- 2014-01-13 IL IL230430A patent/IL230430A0/en unknown
- 2014-01-15 TN TNP2014000016A patent/TN2014000016A1/en unknown
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- 2014-02-10 MA MA36745A patent/MA35342B1/fr unknown
- 2014-02-12 CR CR20140071A patent/CR20140071A/es unknown
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CO6880065A2 (es)	2014-02-28
US20150126513A1 (en)	2015-05-07
EP2731940B1 (en)	2015-08-19
AU2012282076A1 (en)	2014-02-27
ZA201400374B (en)	2014-10-29
NZ620426A (en)	2015-08-28
WO2013008217A1 (en)	2013-01-17
EA201490272A1 (ru)	2014-05-30
US9163003B2 (en)	2015-10-20
DOP2014000012A (es)	2014-07-31
IL230430A0 (en)	2014-03-31
AP2014007400A0 (en)	2014-01-31
EP2731940A1 (en)	2014-05-21
BR112014000792A2 (pt)	2017-10-31
CA2841932A1 (en)	2013-01-17
PH12014500126A1 (en)	2014-02-24
CN103797006B (zh)	2016-01-27
CN103797006A (zh)	2014-05-14
KR20140051944A (ko)	2014-05-02
USRE46942E1 (en)	2018-07-10
CR20140071A (es)	2014-10-16
MA35342B1 (fr)	2014-08-01
JP2014522855A (ja)	2014-09-08
ES2548513T3 (es)	2015-10-19
TN2014000016A1 (en)	2015-07-01
MX2014000536A (es)	2014-12-05

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