JP2016529292A5 - - Google Patents
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- Publication number
- JP2016529292A5 JP2016529292A5 JP2016538906A JP2016538906A JP2016529292A5 JP 2016529292 A5 JP2016529292 A5 JP 2016529292A5 JP 2016538906 A JP2016538906 A JP 2016538906A JP 2016538906 A JP2016538906 A JP 2016538906A JP 2016529292 A5 JP2016529292 A5 JP 2016529292A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- diamine
- benzimidazol
- phenyl
- methyl
- Prior art date
- 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.)
- Granted
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- -1 hydroxyl-amino Chemical group 0.000 claims description 128
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 60
- 101100058550 Mus musculus Bmi1 gene Proteins 0.000 claims description 40
- 125000003282 alkyl amino group Chemical group 0.000 claims description 32
- 206010028980 Neoplasm Diseases 0.000 claims description 28
- 210000004027 cell Anatomy 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 201000011510 cancer Diseases 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 15
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 230000001404 mediated effect Effects 0.000 claims description 12
- 210000000130 stem cell Anatomy 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 239000013522 chelant Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 210000004881 tumor cell Anatomy 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- UVHMUJSQWRYWDU-UHFFFAOYSA-N Cl.Cc1nc2ccccc2n1-c1cc(N)nc(Nc2ccc(cc2)C(F)(F)F)n1 Chemical compound Cl.Cc1nc2ccccc2n1-c1cc(N)nc(Nc2ccc(cc2)C(F)(F)F)n1 UVHMUJSQWRYWDU-UHFFFAOYSA-N 0.000 claims description 4
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 102000004243 Tubulin Human genes 0.000 claims description 4
- 108090000704 Tubulin Proteins 0.000 claims description 4
- 239000003470 adrenal cortex hormone Substances 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 230000001028 anti-proliverative effect Effects 0.000 claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 239000003430 antimalarial agent Substances 0.000 claims description 4
- 239000003443 antiviral agent Substances 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 229940124748 beta 2 agonist Drugs 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000003124 biologic agent Substances 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000000812 cholinergic antagonist Substances 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 239000003862 glucocorticoid Substances 0.000 claims description 4
- 229940125697 hormonal agent Drugs 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000002955 immunomodulating agent Substances 0.000 claims description 4
- 229940121354 immunomodulator Drugs 0.000 claims description 4
- 230000002584 immunomodulator Effects 0.000 claims description 4
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000008177 pharmaceutical agent Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 238000001959 radiotherapy Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002294 steroidal antiinflammatory agent Substances 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- ZQXSKIOXBAHJFB-UHFFFAOYSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-6-(2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC=1C=C(C=CC=1C(F)(F)F)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=CC=C2)C)N ZQXSKIOXBAHJFB-UHFFFAOYSA-N 0.000 claims description 2
- GEFKLPJLQJIZIK-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-3-fluorophenyl]-6-(2-ethyl-6-fluorobenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=C(C=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2)F)CC)N)F)F GEFKLPJLQJIZIK-UHFFFAOYSA-N 0.000 claims description 2
- FTLIXSOLZZNVIS-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-3-fluorophenyl]-6-(2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=C(C=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=CC=C2)C)N)F)F FTLIXSOLZZNVIS-UHFFFAOYSA-N 0.000 claims description 2
- ULAPUNCOGWESBX-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-3-fluorophenyl]-6-(5-fluoro-2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=C(C=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=CC(=C2)F)C)N)F)F ULAPUNCOGWESBX-UHFFFAOYSA-N 0.000 claims description 2
- JVBZMYGXBPXIRT-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-3-fluorophenyl]-6-(6-fluoro-2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=C(C=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2)F)C)N)F)F JVBZMYGXBPXIRT-UHFFFAOYSA-N 0.000 claims description 2
- JUCJUKGQBOPFBZ-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-5-fluoro-6-(2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=C(C(=N1)N)F)N1C(=NC2=C1C=CC=C2)C)N)F JUCJUKGQBOPFBZ-UHFFFAOYSA-N 0.000 claims description 2
- IALBUPOOHQBYQP-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(2,5,6-trimethylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine 6-(3,5-dimethyl-1,2-oxazol-4-yl)-2-N-(4-methoxyphenyl)pyrimidine-2,4-diamine Chemical compound CC1=NOC(=C1C1=CC(=NC(=N1)NC1=CC=C(C=C1)OC)N)C.FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C(=C2)C)C)C)N)F IALBUPOOHQBYQP-UHFFFAOYSA-N 0.000 claims description 2
- PMWSONWBUJYXIA-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(2,6-dimethylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2)C)C)N)F PMWSONWBUJYXIA-UHFFFAOYSA-N 0.000 claims description 2
- JJUBGPRIAWLNSG-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(2-ethyl-6-fluorobenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2)F)CC)N)F JJUBGPRIAWLNSG-UHFFFAOYSA-N 0.000 claims description 2
- XNXCLICHUIPSLU-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(2-propan-2-ylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=CC=C2)C(C)C)N)F XNXCLICHUIPSLU-UHFFFAOYSA-N 0.000 claims description 2
- PBLUFQAQWINLBU-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(4,6-difluoro-2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2F)F)C)N)F PBLUFQAQWINLBU-UHFFFAOYSA-N 0.000 claims description 2
- HSGWNSAGTGJEJS-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(4-fluoro-2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=CC=C2F)C)N)F HSGWNSAGTGJEJS-UHFFFAOYSA-N 0.000 claims description 2
- XQUSLGVVYKQHCP-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(5,6-difluoro-2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C(=C2)F)F)C)N)F XQUSLGVVYKQHCP-UHFFFAOYSA-N 0.000 claims description 2
- KVUUOHXNBZDTBU-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(5,7-difluoro-2-methylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C(=CC(=C2)F)F)C)N)F KVUUOHXNBZDTBU-UHFFFAOYSA-N 0.000 claims description 2
- BAKNKXJUSSAYMT-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(5-fluoro-2-propan-2-ylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=CC(=C2)F)C(C)C)N)F BAKNKXJUSSAYMT-UHFFFAOYSA-N 0.000 claims description 2
- ZOEZVBZFTKJNEE-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-(6-fluoro-2-propan-2-ylbenzimidazol-1-yl)-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2)F)C(C)C)N)F ZOEZVBZFTKJNEE-UHFFFAOYSA-N 0.000 claims description 2
- VVVGUDDIVWGFNM-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-[2-(difluoromethyl)-6-fluorobenzimidazol-1-yl]-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2)F)C(F)F)N)F VVVGUDDIVWGFNM-UHFFFAOYSA-N 0.000 claims description 2
- SHHZOXQIHCKAAN-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-[2-(difluoromethyl)benzimidazol-1-yl]-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=CC=C2)C(F)F)N)F SHHZOXQIHCKAAN-UHFFFAOYSA-N 0.000 claims description 2
- JBUUKDJZTHOULF-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-6-[6-fluoro-2-(methoxymethyl)benzimidazol-1-yl]-1H-pyrimidine-2,4-diamine Chemical compound FC(OC1=CC=C(C=C1)C1(NC(=CC(=N1)N)N1C(=NC2=C1C=C(C=C2)F)COC)N)F JBUUKDJZTHOULF-UHFFFAOYSA-N 0.000 claims description 2
- NPGWDGRCAMIOMW-UHFFFAOYSA-N 4-(6-chloro-2-methylbenzimidazol-1-yl)-2-[4-(trifluoromethyl)anilino]-1H-pyrimidin-6-one Chemical compound ClC=1C=CC2=C(N(C(=N2)C)C2=CC(=NC(=N2)NC2=CC=C(C=C2)C(F)(F)F)O)C=1 NPGWDGRCAMIOMW-UHFFFAOYSA-N 0.000 claims description 2
- GSIOXNJEAZAZJI-UHFFFAOYSA-N 5-fluoro-6-(2-methylbenzimidazol-1-yl)-2-N-[4-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound Cc1nc2ccccc2n1-c1nc(Nc2ccc(cc2)C(F)(F)F)nc(N)c1F GSIOXNJEAZAZJI-UHFFFAOYSA-N 0.000 claims description 2
- VHGCPAWEEVYUGT-UHFFFAOYSA-N 6-(2-ethylbenzimidazol-1-yl)-5-fluoro-2-N-[4-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound CCc1nc2ccccc2n1-c1nc(Nc2ccc(cc2)C(F)(F)F)nc(N)c1F VHGCPAWEEVYUGT-UHFFFAOYSA-N 0.000 claims description 2
- BGRHQELBROFBDH-UHFFFAOYSA-N 6-(4-fluoro-2-methylbenzimidazol-1-yl)-2-N-[3-methyl-4-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound FC1=CC=CC=2N(C(=NC=21)C)C1=CC(=NC(=N1)NC1=CC(=C(C=C1)C(F)(F)F)C)N BGRHQELBROFBDH-UHFFFAOYSA-N 0.000 claims description 2
- DCDIAVGFVYOHKM-UHFFFAOYSA-N 6-(5-chloro-2-cyclopropylbenzimidazol-1-yl)-2-N-[4-(difluoromethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound ClC1=CC2=C(N(C(=N2)C2CC2)C2=CC(=NC(=N2)NC2=CC=C(C=C2)OC(F)F)N)C=C1 DCDIAVGFVYOHKM-UHFFFAOYSA-N 0.000 claims description 2
- MUUNVQIOYJNBBB-UHFFFAOYSA-N 6-(5-chloro-2-cyclopropylbenzimidazol-1-yl)-2-N-[4-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound ClC1=CC2=C(N(C(=N2)C2CC2)C2=CC(=NC(=N2)NC2=CC=C(C=C2)C(F)(F)F)N)C=C1 MUUNVQIOYJNBBB-UHFFFAOYSA-N 0.000 claims description 2
- BHHSOANUXVIOGN-UHFFFAOYSA-N 6-(6-chloro-2-cyclopropylbenzimidazol-1-yl)-2-N-[4-(difluoromethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound ClC=1C=CC2=C(N(C(=N2)C2CC2)C2=CC(=NC(=N2)NC2=CC=C(C=C2)OC(F)F)N)C=1 BHHSOANUXVIOGN-UHFFFAOYSA-N 0.000 claims description 2
- NJXICRJXDBDCMY-UHFFFAOYSA-N 6-[2-(methoxymethyl)benzimidazol-1-yl]-2-N-[4-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound COCc1nc2ccccc2n1-c1cc(N)nc(Nc2ccc(cc2)C(F)(F)F)n1 NJXICRJXDBDCMY-UHFFFAOYSA-N 0.000 claims description 2
- GPVJKNAZBWNDCK-UHFFFAOYSA-N C(C)C1=NC2=C(N1C1=C(C(=NC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)F)C=C(C=C2)F Chemical compound C(C)C1=NC2=C(N1C1=C(C(=NC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)F)C=C(C=C2)F GPVJKNAZBWNDCK-UHFFFAOYSA-N 0.000 claims description 2
- RYIZSNJRUYFDTF-UHFFFAOYSA-N C(C)C1=NC2=C(N1C1=CC(=NC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=C(C=C2)F Chemical compound C(C)C1=NC2=C(N1C1=CC(=NC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=C(C=C2)F RYIZSNJRUYFDTF-UHFFFAOYSA-N 0.000 claims description 2
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- PFTWICZZYOGGCM-UHFFFAOYSA-N C1(CC1)C1=NC2=C(N1C1=CC(=NC(=N1)NC1=CC(=C(C=C1)OC(F)F)F)N)C=C(C=C2)F Chemical compound C1(CC1)C1=NC2=C(N1C1=CC(=NC(=N1)NC1=CC(=C(C=C1)OC(F)F)F)N)C=C(C=C2)F PFTWICZZYOGGCM-UHFFFAOYSA-N 0.000 claims description 2
- QNRDNFFQKNHDSS-UHFFFAOYSA-N C1(CC1)C1=NC2=C(N1C1=CC(=NC(=N1)NC1=CC=C(C=C1)C(F)(F)F)C#N)C=C(C(=C2)F)F Chemical compound C1(CC1)C1=NC2=C(N1C1=CC(=NC(=N1)NC1=CC=C(C=C1)C(F)(F)F)C#N)C=C(C(=C2)F)F QNRDNFFQKNHDSS-UHFFFAOYSA-N 0.000 claims description 2
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-
2013
- 2013-11-21 MX MX2016002642A patent/MX370588B/es active IP Right Grant
- 2013-11-21 CN CN201380080643.5A patent/CN105683166B/zh not_active Expired - Fee Related
- 2013-11-21 AU AU2013399092A patent/AU2013399092A1/en not_active Abandoned
- 2013-11-21 KR KR1020167008197A patent/KR102232595B1/ko not_active Expired - Fee Related
- 2013-11-21 EP EP13892399.0A patent/EP3039015B1/en not_active Not-in-force
- 2013-11-21 NZ NZ718055A patent/NZ718055A/en not_active IP Right Cessation
- 2013-11-21 US US14/914,909 patent/US10370371B2/en active Active
- 2013-11-21 EA EA201690502A patent/EA034866B1/ru not_active IP Right Cessation
- 2013-11-21 NZ NZ748260A patent/NZ748260A/en not_active IP Right Cessation
- 2013-11-21 TW TW102142556A patent/TWI692477B/zh not_active IP Right Cessation
- 2013-11-21 AR ARP130104301A patent/AR093580A1/es active IP Right Grant
- 2013-11-21 WO PCT/US2013/071216 patent/WO2015030847A1/en not_active Ceased
- 2013-11-21 CA CA2922657A patent/CA2922657C/en active Active
- 2013-11-21 JP JP2016538906A patent/JP6524094B2/ja not_active Expired - Fee Related
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2016
- 2016-02-28 IL IL244321A patent/IL244321B/en active IP Right Grant
- 2016-02-29 CL CL2016000466A patent/CL2016000466A1/es unknown
- 2016-03-11 ZA ZA2016/01697A patent/ZA201601697B/en unknown
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2018
- 2018-11-27 AU AU2018271277A patent/AU2018271277B2/en not_active Ceased
- 2018-12-14 JP JP2018234524A patent/JP6728321B2/ja not_active Expired - Fee Related
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