HRP20210417T1 - Pripravci magnezija namijenjeni moduliranju farmakokinetike i farmakodinamike inzulina, te boli na mjestu injekcije - Google Patents
Pripravci magnezija namijenjeni moduliranju farmakokinetike i farmakodinamike inzulina, te boli na mjestu injekcije Download PDFInfo
- Publication number
- HRP20210417T1 HRP20210417T1 HRP20210417TT HRP20210417T HRP20210417T1 HR P20210417 T1 HRP20210417 T1 HR P20210417T1 HR P20210417T T HRP20210417T T HR P20210417TT HR P20210417 T HRP20210417 T HR P20210417T HR P20210417 T1 HRP20210417 T1 HR P20210417T1
- Authority
- HR
- Croatia
- Prior art keywords
- magnesium
- insulin
- acid
- formulation according
- concentration
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims 16
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 title claims 13
- 108090001061 Insulin Proteins 0.000 title claims 6
- 102000004877 Insulin Human genes 0.000 title claims 6
- 229940125396 insulin Drugs 0.000 title claims 6
- 239000011777 magnesium Substances 0.000 title claims 2
- 229910052749 magnesium Inorganic materials 0.000 title claims 2
- 206010022086 Injection site pain Diseases 0.000 title 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 title 1
- 230000003285 pharmacodynamic effect Effects 0.000 title 1
- 238000009472 formulation Methods 0.000 claims 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 9
- 150000002681 magnesium compounds Chemical class 0.000 claims 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 4
- 239000001509 sodium citrate Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 235000015165 citric acid Nutrition 0.000 claims 3
- 230000003381 solubilizing effect Effects 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 239000003381 stabilizer Substances 0.000 claims 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- FCKYPQBAHLOOJQ-UHFFFAOYSA-N Cyclohexane-1,2-diaminetetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)C1CCCCC1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UHFFFAOYSA-N 0.000 claims 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 239000002738 chelating agent Substances 0.000 claims 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 2
- -1 magnesium halides Chemical class 0.000 claims 2
- 239000000347 magnesium hydroxide Substances 0.000 claims 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 2
- 235000012254 magnesium hydroxide Nutrition 0.000 claims 2
- 239000000395 magnesium oxide Substances 0.000 claims 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 2
- 159000000003 magnesium salts Chemical class 0.000 claims 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims 2
- ACTRVOBWPAIOHC-UHFFFAOYSA-N succimer Chemical compound OC(=O)C(S)C(S)C(O)=O ACTRVOBWPAIOHC-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 2
- 229940038773 trisodium citrate Drugs 0.000 claims 2
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 108010073961 Insulin Aspart Proteins 0.000 claims 1
- 108010089308 Insulin Detemir Proteins 0.000 claims 1
- 108010057186 Insulin Glargine Proteins 0.000 claims 1
- 108010065920 Insulin Lispro Proteins 0.000 claims 1
- COCFEDIXXNGUNL-RFKWWTKHSA-N Insulin glargine Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(=O)NCC(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 COCFEDIXXNGUNL-RFKWWTKHSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000000783 alginic acid Substances 0.000 claims 1
- 235000010443 alginic acid Nutrition 0.000 claims 1
- 229960001126 alginic acid Drugs 0.000 claims 1
- 229920000615 alginic acid Polymers 0.000 claims 1
- 150000004781 alginic acids Chemical class 0.000 claims 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims 1
- RCHHVVGSTHAVPF-ZPHPLDECSA-N apidra Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3N=CNC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CNC=N1 RCHHVVGSTHAVPF-ZPHPLDECSA-N 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- XZTWHWHGBBCSMX-UHFFFAOYSA-J dimagnesium;phosphonato phosphate Chemical compound [Mg+2].[Mg+2].[O-]P([O-])(=O)OP([O-])([O-])=O XZTWHWHGBBCSMX-UHFFFAOYSA-J 0.000 claims 1
- 229950007919 egtazic acid Drugs 0.000 claims 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- WNRQPCUGRUFHED-DETKDSODSA-N humalog Chemical compound C([C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(O)=O)C1=CC=C(O)C=C1.C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 WNRQPCUGRUFHED-DETKDSODSA-N 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 229960004717 insulin aspart Drugs 0.000 claims 1
- 239000004026 insulin derivative Substances 0.000 claims 1
- 229960003948 insulin detemir Drugs 0.000 claims 1
- 229960002869 insulin glargine Drugs 0.000 claims 1
- 229960000696 insulin glulisine Drugs 0.000 claims 1
- 108700039926 insulin glulisine Proteins 0.000 claims 1
- 229960002068 insulin lispro Drugs 0.000 claims 1
- UGOZVNFCFYTPAZ-IOXYNQHNSA-N levemir Chemical compound CCCCCCCCCCCCCC(=O)NCCCC[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=2N=CNC=2)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=2N=CNC=2)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=2C=CC=CC=2)C(C)C)CSSC[C@@H]2NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(C)C)CSSC[C@H](NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC2=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CSSC1)C(=O)N[C@@H](CC(N)=O)C(O)=O)CC1=CC=C(O)C=C1 UGOZVNFCFYTPAZ-IOXYNQHNSA-N 0.000 claims 1
- 235000019136 lipoic acid Nutrition 0.000 claims 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 claims 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 claims 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- VOMXSOIBEJBQNF-UTTRGDHVSA-N novorapid Chemical compound C([C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(O)=O)C1=CC=C(O)C=C1.C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 VOMXSOIBEJBQNF-UTTRGDHVSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229960002663 thioctic acid Drugs 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Zoology (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (14)
1. Injekcijska formulacija inzulina, naznačena time što sadrži djelotvornu količinu sredstva za otapanje/stabiliziranje, kojeg se bira između octene kiseline, askorbinske kiseline, limunske kiseline, glutaminske kiseline, asparaginske kiseline, jantarne kiseline, fumarne kiseline, maleinske kiseline, adipinske kiseline, te njihovih soli; djelotvornu količinu cinkovog kelatora; i jedan ili više magnezijevih spojeva, gdje je koncentracija inzulina 100, 200, 400 ili 500 UmL, gdje jedan ili više magnezijevih spojeva čine anorgansku magnezijevu sol, te gdje se koncentracija jednog ili više magnezijevih spojeva kreće od 0,1 do 10 mg/ml.
2. Formulacija u skladu s patentnim zahtjevom 1, naznačena time što je inzulin ljudski rekombinantni inzulin.
3. Formulacija patentnim zahtjevom 1, naznačena time što inzulin je inzulinski analog, kojeg se bira između inzulin-lispro, inzulin-glargina, inzulin-asparta, inzulin-glulizina i inzulin-detemira.
4. Formulacija u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačena time što se anorganske magnezijeve soli bira iz skupine koju čine magnezijev hidroksid (Mg(OH)2), magnezijev sulfat (MgSO4), magnezijevi halogenidi, poput magnezijevog klorida (MgCl2), magnezijevog bromida (MgBr2), te magnezijevog jodida (MgI2); magnezijevog pirofosfata, magnezijevog sulfata heptahidrata, magnezijevog oksida (MgO2), te njihove kombinacije.
5. Formulacija u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što se koncentracija jednog ili više magnezijevih spojeva kreće od 0,1 do 5 mg/ml.
6. Formulacija u skladu s patentnim zahtjevom 5, naznačena time što se koncentracija jednog ili više magnezijevih spojeva kreće od 0,1 do 2 mg/ml.
7. Formulacija u skladu s patentnim zahtjevom 6, naznačena time što se koncentracija jednog ili više magnezijevih spojeva kreće od 0,2 do 2 mg/ml.
8. Formulacija u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačena time što sredstvo za otapanje/stabiliziranje tvori citratne ione, a pH je otprilike 7.
9. Formulacija u skladu s patentnim zahtjevom 1, naznačen time što je sredstvo za otapanje/stabiliziranje limunska kiselina ili natrijev citrat.
10. Formulacija u skladu s patentnim zahtjevom 9, naznačena time što je limunska kiselina ili natrijev citrat u rasponu od 7 x 10–3 M do 2 x 10–2 M.
11. Formulacija u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačena time što dodatno sadrži m-krezol.
12. Formulacija u skladu s patentnim zahtjevom 11, naznačena time što dodatno sadrži glicerol.
13. Formulacija u skladu s bilo kojim od patentnih zahtjeva 1 do 12, naznačena time što se kelator bira između etilendiamintetraoctene kiseline (EDTA), EGTA, alginske kiseline, α-lipoinske kiseline, dimerkaptojantarne kiseline (DMSA), CDTA (1,2-diaminocikloheksantetraoctena kiselina) i trinatrijevog citrata (TSC).
14. Formulacija u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačena time što je namijenjena upotrebi u postupku liječenja osobe s dijabetesom koja se sastoji u injiciranju u osobu djelotvorne količine formulacije.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US201261624844P | 2012-04-16 | 2012-04-16 | |
US201261704066P | 2012-09-21 | 2012-09-21 | |
US13/826,806 US9381247B2 (en) | 2012-04-16 | 2013-03-14 | Magnesium compositions for modulating the pharmacokinetics and pharmacodynamics of insulin and insulin analogs, and injection site pain |
PCT/US2013/036742 WO2013158618A1 (en) | 2012-04-16 | 2013-04-16 | Magnesium compositions for modulating the pharmacokinetics and pharmacodynamics of insulin and insulin analogs, and injection site pain |
EP13721441.7A EP2838506B1 (en) | 2012-04-16 | 2013-04-16 | Magnesium compositions for modulating the pharmacokinetics and pharmacodynamics of insulin, and injection site pain |
Publications (1)
Publication Number | Publication Date |
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HRP20210417T1 true HRP20210417T1 (hr) | 2021-04-30 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HRP20210417TT HRP20210417T1 (hr) | 2012-04-16 | 2021-03-12 | Pripravci magnezija namijenjeni moduliranju farmakokinetike i farmakodinamike inzulina, te boli na mjestu injekcije |
Country Status (25)
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US (1) | US9381247B2 (hr) |
EP (2) | EP2838506B1 (hr) |
JP (2) | JP6422855B2 (hr) |
KR (1) | KR101966484B1 (hr) |
CN (1) | CN104394847A (hr) |
AU (1) | AU2013249495B2 (hr) |
CA (1) | CA2869883A1 (hr) |
CY (1) | CY1123825T1 (hr) |
DK (1) | DK2838506T3 (hr) |
ES (1) | ES2854874T3 (hr) |
HK (2) | HK1203371A1 (hr) |
HR (1) | HRP20210417T1 (hr) |
HU (1) | HUE053303T2 (hr) |
IL (1) | IL234987A0 (hr) |
IN (1) | IN2014DN08417A (hr) |
LT (1) | LT2838506T (hr) |
MX (1) | MX2014012245A (hr) |
PL (1) | PL2838506T3 (hr) |
PT (1) | PT2838506T (hr) |
RS (1) | RS61533B1 (hr) |
RU (1) | RU2014145846A (hr) |
SG (1) | SG11201406491PA (hr) |
SI (1) | SI2838506T1 (hr) |
WO (1) | WO2013158618A1 (hr) |
ZA (1) | ZA201407410B (hr) |
Families Citing this family (30)
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CN104902922B (zh) | 2012-11-13 | 2017-12-12 | 阿道恰公司 | 包含经取代阴离子化合物的速效胰岛素制剂 |
CA2936563A1 (en) * | 2014-01-13 | 2015-07-16 | Thermalin Diabetes, Llc | Rapid action insulin formulations and pharmaceutical delivery systems |
WO2015120457A1 (en) * | 2014-02-10 | 2015-08-13 | Biodel Inc. | Stabilized ultra-rapid-acting insulin formulations |
TWI685348B (zh) * | 2014-05-08 | 2020-02-21 | 美國禮來大藥廠 | 速效胰島素組合物 |
WO2016007935A2 (en) | 2014-07-10 | 2016-01-14 | Companion Medical, Inc. | Medicine administering system including injection pen and companion device |
AR102869A1 (es) | 2014-12-16 | 2017-03-29 | Lilly Co Eli | Composiciones de insulina de rápida acción |
AU2016209405A1 (en) * | 2015-01-20 | 2017-08-24 | Case Western Reserve University | Insulin analogues with selective signaling properties and reduced mitogenicity |
JO3749B1 (ar) * | 2015-08-27 | 2021-01-31 | Lilly Co Eli | تركيبات إنسولين سريعة المفعول |
WO2017132577A1 (en) | 2016-01-29 | 2017-08-03 | Companion Medical, Inc. | Automatic medication delivery tracking |
GB201607918D0 (en) | 2016-05-06 | 2016-06-22 | Arecor Ltd | Novel formulations |
GB201707189D0 (en) * | 2017-05-05 | 2017-06-21 | Arecor Ltd | Novel formulations |
JOP20190277B1 (ar) | 2017-06-01 | 2023-09-17 | Lilly Co Eli | تركيبات إنسولين سريعة المفعول |
EP3635591A4 (en) | 2017-06-09 | 2021-03-24 | Companion Medical, Inc. | SMART DRUG DELIVERY SYSTEMS AND PROCESSES |
EP3694583A4 (en) * | 2017-10-12 | 2021-08-04 | Companion Medical, Inc. | INTELLIGENT DRUG DELIVERY SYSTEMS AND METHODS FOR DOSAGE RECOMMENDATION AND ADMINISTRATION |
US11116899B2 (en) | 2017-12-12 | 2021-09-14 | Bigfoot Biomedical, Inc. | User interface for diabetes management systems and devices |
US11464459B2 (en) | 2017-12-12 | 2022-10-11 | Bigfoot Biomedical, Inc. | User interface for diabetes management systems including flash glucose monitor |
US11090439B2 (en) | 2017-12-12 | 2021-08-17 | Bigfoot Biomedical, Inc. | Therapy management systems, methods, and devices |
US11077243B2 (en) | 2017-12-12 | 2021-08-03 | Bigfoot Biomedical, Inc. | Devices, systems, and methods for estimating active medication from injections |
US11083852B2 (en) | 2017-12-12 | 2021-08-10 | Bigfoot Biomedical, Inc. | Insulin injection assistance systems, methods, and devices |
US10987464B2 (en) | 2017-12-12 | 2021-04-27 | Bigfoot Biomedical, Inc. | Pen cap for insulin injection pens and associated methods and systems |
US10898653B2 (en) | 2018-05-08 | 2021-01-26 | Companion Medical, Inc. | Intelligent medication delivery systems and methods for dose setting and dispensing monitoring |
US11664107B2 (en) | 2018-05-08 | 2023-05-30 | Medtronic Minimed, Inc. | Intelligent medication delivery systems and methods using a prescription-regulated software application |
USD893020S1 (en) | 2018-05-11 | 2020-08-11 | Companion Medical, Inc. | Injection pen |
US11587663B2 (en) | 2018-06-20 | 2023-02-21 | Medtronic Minimed, Inc. | Intelligent medication delivery systems and methods for medicine dose calculation and reporting |
USD892819S1 (en) | 2018-06-20 | 2020-08-11 | Companion Medical, Inc. | Display screen with graphical user interface |
FR3083984A1 (fr) | 2018-07-23 | 2020-01-24 | Adocia | Dispositif pour injecter une solution d'insuline(s) |
WO2019243627A1 (fr) | 2018-06-23 | 2019-12-26 | Adocia | Dispositif pour injecter une solution d'insuline(s) |
FR3083985A1 (fr) | 2018-07-23 | 2020-01-24 | Adocia | Dispositif pour injecter une solution d'insuline(s) |
US11948671B2 (en) | 2019-04-11 | 2024-04-02 | Medtronic Minimed, Inc. | Intelligent accessories for medicine dispensing device |
US11701473B2 (en) | 2021-06-23 | 2023-07-18 | Medtronic Minimed, Inc. | Reusable injection pens |
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PH23446A (en) * | 1986-10-20 | 1989-08-07 | Novo Industri As | Peptide preparations |
DK503386D0 (da) * | 1986-10-20 | 1986-10-20 | Novo Industri As | Peptidpraeparater |
JP2000517188A (ja) | 1996-08-30 | 2000-12-26 | ライフ テクノロジーズ,インコーポレイテッド | 無血清哺乳動物細胞培養培地およびその使用 |
DE69924232D1 (de) * | 1998-01-09 | 2005-04-21 | Novo Nordisk As | Stabilisierte insulin-zubereitungen |
US20080096800A1 (en) | 2004-03-12 | 2008-04-24 | Biodel, Inc. | Rapid mucosal gel or film insulin compositions |
ES2398318T3 (es) | 2004-03-12 | 2013-03-15 | Biodel, Inc. | Composiciones de suministro de fármacos de acción rápida |
US20080090753A1 (en) * | 2004-03-12 | 2008-04-17 | Biodel, Inc. | Rapid Acting Injectable Insulin Compositions |
US20080085298A1 (en) | 2004-03-12 | 2008-04-10 | Biodel, Inc. | Rapid Mucosal Gel or Film Insulin Compositions |
EP2124539A2 (en) | 2007-02-17 | 2009-12-02 | President and Fellows of Harvard College | Compositions and method for tissue preservation |
TWI394580B (zh) | 2008-04-28 | 2013-05-01 | Halozyme Inc | 超快起作用胰島素組成物 |
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FR2943538B1 (fr) * | 2009-03-27 | 2011-05-20 | Adocia | Formulation a action rapide d'insuline recombinante humaine |
CA2805031A1 (en) | 2010-07-07 | 2012-01-12 | Biodel, Inc. | Compositions and methods for modulating the pharmacokinetics and pharmacodynamics of insulin |
-
2013
- 2013-03-14 US US13/826,806 patent/US9381247B2/en active Active
- 2013-04-16 AU AU2013249495A patent/AU2013249495B2/en active Active
- 2013-04-16 IN IN8417DEN2014 patent/IN2014DN08417A/en unknown
- 2013-04-16 PL PL13721441T patent/PL2838506T3/pl unknown
- 2013-04-16 CA CA2869883A patent/CA2869883A1/en not_active Abandoned
- 2013-04-16 SG SG11201406491PA patent/SG11201406491PA/en unknown
- 2013-04-16 DK DK13721441.7T patent/DK2838506T3/da active
- 2013-04-16 RS RS20210209A patent/RS61533B1/sr unknown
- 2013-04-16 PT PT137214417T patent/PT2838506T/pt unknown
- 2013-04-16 CN CN201380029323.7A patent/CN104394847A/zh active Pending
- 2013-04-16 JP JP2015505989A patent/JP6422855B2/ja active Active
- 2013-04-16 MX MX2014012245A patent/MX2014012245A/es unknown
- 2013-04-16 WO PCT/US2013/036742 patent/WO2013158618A1/en active Application Filing
- 2013-04-16 LT LTEP13721441.7T patent/LT2838506T/lt unknown
- 2013-04-16 KR KR1020147032221A patent/KR101966484B1/ko active IP Right Grant
- 2013-04-16 EP EP13721441.7A patent/EP2838506B1/en active Active
- 2013-04-16 EP EP20215156.9A patent/EP3827813A1/en not_active Withdrawn
- 2013-04-16 RU RU2014145846A patent/RU2014145846A/ru not_active Application Discontinuation
- 2013-04-16 HU HUE13721441A patent/HUE053303T2/hu unknown
- 2013-04-16 ES ES13721441T patent/ES2854874T3/es active Active
- 2013-04-16 SI SI201331836T patent/SI2838506T1/sl unknown
-
2014
- 2014-10-05 IL IL234987A patent/IL234987A0/en unknown
- 2014-10-13 ZA ZA2014/07410A patent/ZA201407410B/en unknown
-
2015
- 2015-04-22 HK HK15103911.3A patent/HK1203371A1/xx unknown
- 2015-08-25 HK HK15108257.4A patent/HK1207577A1/xx unknown
-
2018
- 2018-10-16 JP JP2018194834A patent/JP2019023223A/ja active Pending
-
2021
- 2021-02-10 CY CY20211100113T patent/CY1123825T1/el unknown
- 2021-03-12 HR HRP20210417TT patent/HRP20210417T1/hr unknown
Also Published As
Publication number | Publication date |
---|---|
JP2015512952A (ja) | 2015-04-30 |
EP3827813A1 (en) | 2021-06-02 |
CY1123825T1 (el) | 2022-05-27 |
EP2838506B1 (en) | 2021-01-06 |
IL234987A0 (en) | 2014-12-31 |
IN2014DN08417A (hr) | 2015-05-08 |
US20140113856A1 (en) | 2014-04-24 |
CA2869883A1 (en) | 2013-10-24 |
DK2838506T3 (da) | 2021-01-18 |
HK1207577A1 (en) | 2016-02-05 |
SG11201406491PA (en) | 2014-11-27 |
ES2854874T3 (es) | 2021-09-23 |
US9381247B2 (en) | 2016-07-05 |
RU2014145846A (ru) | 2016-06-10 |
ZA201407410B (en) | 2015-06-24 |
HUE053303T2 (hu) | 2021-06-28 |
KR20140146209A (ko) | 2014-12-24 |
WO2013158618A1 (en) | 2013-10-24 |
PL2838506T3 (pl) | 2021-06-28 |
HK1203371A1 (en) | 2015-10-30 |
MX2014012245A (es) | 2015-06-05 |
SI2838506T1 (sl) | 2021-02-26 |
LT2838506T (lt) | 2021-03-25 |
JP2019023223A (ja) | 2019-02-14 |
KR101966484B1 (ko) | 2019-04-05 |
JP6422855B2 (ja) | 2018-11-14 |
RS61533B1 (sr) | 2021-04-29 |
EP2838506A1 (en) | 2015-02-25 |
CN104394847A (zh) | 2015-03-04 |
PT2838506T (pt) | 2021-02-23 |
AU2013249495B2 (en) | 2016-05-12 |
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