HRP20171209T1 - Farmaceutski pripravak za liječenje upalnih bolesti posredovanih putem mcp-1 - Google Patents
Farmaceutski pripravak za liječenje upalnih bolesti posredovanih putem mcp-1 Download PDFInfo
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- HRP20171209T1 HRP20171209T1 HRP20171209TT HRP20171209T HRP20171209T1 HR P20171209 T1 HRP20171209 T1 HR P20171209T1 HR P20171209T T HRP20171209T T HR P20171209TT HR P20171209 T HRP20171209 T HR P20171209T HR P20171209 T1 HRP20171209 T1 HR P20171209T1
- Authority
- HR
- Croatia
- Prior art keywords
- pharmaceutical composition
- group
- composition according
- amlodipine
- diltiazem
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims 11
- 101100504320 Caenorhabditis elegans mcp-1 gene Proteins 0.000 title 1
- 208000027866 inflammatory disease Diseases 0.000 title 1
- 230000001404 mediated effect Effects 0.000 title 1
- -1 2-((1-benzyl-3-indazolyl)methoxy)-2-methyl-propionic acid compound Chemical class 0.000 claims 4
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims 4
- 229960000528 amlodipine Drugs 0.000 claims 4
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims 4
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims 4
- 229960004166 diltiazem Drugs 0.000 claims 4
- 229960001722 verapamil Drugs 0.000 claims 4
- 239000005541 ACE inhibitor Substances 0.000 claims 3
- 239000002083 C09CA01 - Losartan Substances 0.000 claims 3
- 239000002947 C09CA04 - Irbesartan Substances 0.000 claims 3
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims 3
- 229940125364 angiotensin receptor blocker Drugs 0.000 claims 3
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 3
- 229960002198 irbesartan Drugs 0.000 claims 3
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 claims 3
- 229960004773 losartan Drugs 0.000 claims 3
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 claims 3
- 229960003401 ramipril Drugs 0.000 claims 3
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 claims 3
- 229960002855 simvastatin Drugs 0.000 claims 3
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims 3
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims 2
- PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 claims 2
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 claims 2
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 claims 2
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims 2
- 239000002053 C09CA06 - Candesartan Substances 0.000 claims 2
- 108010061435 Enalapril Proteins 0.000 claims 2
- XQLWNAFCTODIRK-UHFFFAOYSA-N Gallopamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C(OC)=C1 XQLWNAFCTODIRK-UHFFFAOYSA-N 0.000 claims 2
- 108010007859 Lisinopril Proteins 0.000 claims 2
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims 2
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims 2
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims 2
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 claims 2
- 229960002992 barnidipine Drugs 0.000 claims 2
- VXMOONUMYLCFJD-DHLKQENFSA-N barnidipine Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@@H]2CN(CC=3C=CC=CC=3)CC2)=CC=CC([N+]([O-])=O)=C1 VXMOONUMYLCFJD-DHLKQENFSA-N 0.000 claims 2
- 229960000932 candesartan Drugs 0.000 claims 2
- SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 claims 2
- 229960000830 captopril Drugs 0.000 claims 2
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229960000873 enalapril Drugs 0.000 claims 2
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 claims 2
- 229960003580 felodipine Drugs 0.000 claims 2
- 229960000457 gallopamil Drugs 0.000 claims 2
- 229960004427 isradipine Drugs 0.000 claims 2
- 229960004340 lacidipine Drugs 0.000 claims 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims 2
- 229960004294 lercanidipine Drugs 0.000 claims 2
- ZDXUKAKRHYTAKV-UHFFFAOYSA-N lercanidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZDXUKAKRHYTAKV-UHFFFAOYSA-N 0.000 claims 2
- 229960002394 lisinopril Drugs 0.000 claims 2
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 claims 2
- 229960004844 lovastatin Drugs 0.000 claims 2
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims 2
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims 2
- 229960003963 manidipine Drugs 0.000 claims 2
- ANEBWFXPVPTEET-UHFFFAOYSA-N manidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANEBWFXPVPTEET-UHFFFAOYSA-N 0.000 claims 2
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims 2
- 229960001783 nicardipine Drugs 0.000 claims 2
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims 2
- 229960001597 nifedipine Drugs 0.000 claims 2
- 229960000715 nimodipine Drugs 0.000 claims 2
- 229960000227 nisoldipine Drugs 0.000 claims 2
- 229960005425 nitrendipine Drugs 0.000 claims 2
- 229960002582 perindopril Drugs 0.000 claims 2
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 claims 2
- 229960002965 pravastatin Drugs 0.000 claims 2
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims 2
- 229960002909 spirapril Drugs 0.000 claims 2
- HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 claims 2
- 108700035424 spirapril Proteins 0.000 claims 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims 2
- 229960004699 valsartan Drugs 0.000 claims 2
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 claims 2
- RKXVEXUAWGRFNP-MUUNZHRXSA-N (2r)-2-[2-[3-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]propoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one Chemical compound S1C2=CC=CC=C2N(C)C(=O)[C@H]1C1=CC(OC)=CC=C1OCCCN(C)CCOC1=CC=C(OCO2)C2=C1 RKXVEXUAWGRFNP-MUUNZHRXSA-N 0.000 claims 1
- NVXFXLSOGLFXKQ-JMSVASOKSA-N (2s)-1-[(2r,4r)-5-ethoxy-2,4-dimethyl-5-oxopentanoyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)[C@H](C)C[C@@H](C)C(=O)OCC)[C@H](C(O)=O)CC2=C1 NVXFXLSOGLFXKQ-JMSVASOKSA-N 0.000 claims 1
- QIJLJZOGPPQCOG-NFAWXSAZSA-N (2s)-1-[(2s)-3-[(2r)-2-(cyclohexanecarbonylamino)propanoyl]sulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylic acid Chemical compound N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(=O)C1CCCCC1 QIJLJZOGPPQCOG-NFAWXSAZSA-N 0.000 claims 1
- AHYHTSYNOHNUSH-GBBGEASQSA-N (2s,3as,7as)-1-[(2s)-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 AHYHTSYNOHNUSH-GBBGEASQSA-N 0.000 claims 1
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 claims 1
- FAKRSMQSSFJEIM-BQBZGAKWSA-N 1-(3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid Chemical compound SC[C@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-BQBZGAKWSA-N 0.000 claims 1
- JQSAYKKFZOSZGJ-UHFFFAOYSA-N 1-[bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCN(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 JQSAYKKFZOSZGJ-UHFFFAOYSA-N 0.000 claims 1
- ZBIAKUMOEKILTF-UHFFFAOYSA-N 2-[4-[4,4-bis(4-fluorophenyl)butyl]-1-piperazinyl]-N-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ZBIAKUMOEKILTF-UHFFFAOYSA-N 0.000 claims 1
- NSVFSAJIGAJDMR-UHFFFAOYSA-N 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CC=1NC(C)=C(C(=O)OCCN(CC=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1P1(=O)OCC(C)(C)CO1 NSVFSAJIGAJDMR-UHFFFAOYSA-N 0.000 claims 1
- NMKSAYKQLCHXDK-UHFFFAOYSA-N 3,3-diphenyl-N-(1-phenylethyl)-1-propanamine Chemical compound C=1C=CC=CC=1C(C)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMKSAYKQLCHXDK-UHFFFAOYSA-N 0.000 claims 1
- ZGRIPYHIFXGCHR-UHFFFAOYSA-N 3-o-[2-[(4-fluorophenyl)methyl-methylamino]ethyl] 5-o-propan-2-yl 4-(1,3-benzodioxol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C=1C=CC=2OCOC=2C=1C1C(C(=O)OC(C)C)=C(C)NC(C)=C1C(=O)OCCN(C)CC1=CC=C(F)C=C1 ZGRIPYHIFXGCHR-UHFFFAOYSA-N 0.000 claims 1
- FHHHOYXPRDYHEZ-COXVUDFISA-N Alacepril Chemical group CC(=O)SC[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 FHHHOYXPRDYHEZ-COXVUDFISA-N 0.000 claims 1
- NCUCGYYHUFIYNU-UHFFFAOYSA-N Aranidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)=O)C1C1=CC=CC=C1[N+]([O-])=O NCUCGYYHUFIYNU-UHFFFAOYSA-N 0.000 claims 1
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- HBNPJJILLOYFJU-VMPREFPWSA-N Mibefradil Chemical compound C1CC2=CC(F)=CC=C2[C@H](C(C)C)[C@@]1(OC(=O)COC)CCN(C)CCCC1=NC2=CC=CC=C2N1 HBNPJJILLOYFJU-VMPREFPWSA-N 0.000 claims 1
- FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 claims 1
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- 239000005477 Pratosartan Substances 0.000 claims 1
- IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 claims 1
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- GYKFWCDBQAFCLJ-RTWAWAEBSA-N [(2s,3s)-8-chloro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=C(Cl)C=C2S1 GYKFWCDBQAFCLJ-RTWAWAEBSA-N 0.000 claims 1
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- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 1
- 239000003529 anticholesteremic agent Substances 0.000 claims 1
- 229940127226 anticholesterol agent Drugs 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
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- QZVNQOLPLYWLHQ-ZEQKJWHPSA-N benidipine Chemical compound C1([C@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@H]2CN(CC=3C=CC=CC=3)CCC2)=CC=CC([N+]([O-])=O)=C1 QZVNQOLPLYWLHQ-ZEQKJWHPSA-N 0.000 claims 1
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- CUZMQPZYCDIHQL-VCTVXEGHSA-L calcium;(2s)-1-[(2s)-3-[(2r)-2-(cyclohexanecarbonylamino)propanoyl]sulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylate Chemical compound [Ca+2].N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C([O-])=O)C(=O)C1CCCCC1.N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C([O-])=O)C(=O)C1CCCCC1 CUZMQPZYCDIHQL-VCTVXEGHSA-L 0.000 claims 1
- 229950005749 ceronapril Drugs 0.000 claims 1
- 229950006523 cilexetil Drugs 0.000 claims 1
- 229950000308 clentiazem Drugs 0.000 claims 1
- VTDCYOLLYVAJSY-UHFFFAOYSA-N cyclohexyl propan-2-yl carbonate Chemical compound CC(C)OC(=O)OC1CCCCC1 VTDCYOLLYVAJSY-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229950003102 efonidipine Drugs 0.000 claims 1
- 229950010020 elgodipine Drugs 0.000 claims 1
- 229960002680 enalaprilat Drugs 0.000 claims 1
- LZFZMUMEGBBDTC-QEJZJMRPSA-N enalaprilat (anhydrous) Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 LZFZMUMEGBBDTC-QEJZJMRPSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229960004351 etafenone Drugs 0.000 claims 1
- OEGDFSLNGABBKJ-UHFFFAOYSA-N etafenone Chemical compound CCN(CC)CCOC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 OEGDFSLNGABBKJ-UHFFFAOYSA-N 0.000 claims 1
- 229960002602 fendiline Drugs 0.000 claims 1
- SMANXXCATUTDDT-QPJJXVBHSA-N flunarizine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C\C=C\C=2C=CC=CC=2)CC1 SMANXXCATUTDDT-QPJJXVBHSA-N 0.000 claims 1
- 229960000326 flunarizine Drugs 0.000 claims 1
- 229960002490 fosinopril Drugs 0.000 claims 1
- 229960001880 fosinopril sodium Drugs 0.000 claims 1
- WOIWWYDXDVSWAZ-RTWAWAEBSA-N fosinoprilat Chemical compound C([C@@H](C[C@H]1C(=O)O)C2CCCCC2)N1C(=O)CP(O)(=O)CCCCC1=CC=CC=C1 WOIWWYDXDVSWAZ-RTWAWAEBSA-N 0.000 claims 1
- 229960003018 fosinoprilat Drugs 0.000 claims 1
- 229960003180 glutathione Drugs 0.000 claims 1
- 108010047748 hemorphin 4 Proteins 0.000 claims 1
- 229950009810 indolapril Drugs 0.000 claims 1
- 229960001941 lidoflazine Drugs 0.000 claims 1
- 229950007692 lomerizine Drugs 0.000 claims 1
- 229950009116 mevastatin Drugs 0.000 claims 1
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 claims 1
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 claims 1
- 229960004438 mibefradil Drugs 0.000 claims 1
- 229950006549 moveltipril Drugs 0.000 claims 1
- 229960005366 nilvadipine Drugs 0.000 claims 1
- 229960005117 olmesartan Drugs 0.000 claims 1
- VTRAEEWXHOVJFV-UHFFFAOYSA-N olmesartan Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 VTRAEEWXHOVJFV-UHFFFAOYSA-N 0.000 claims 1
- 229950008492 pentopril Drugs 0.000 claims 1
- ODAIHABQVKJNIY-PEDHHIEDSA-N perindoprilat Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(O)=O)[C@H]21 ODAIHABQVKJNIY-PEDHHIEDSA-N 0.000 claims 1
- 229960005226 perindoprilat Drugs 0.000 claims 1
- 229950005649 pratosartan Drugs 0.000 claims 1
- KCTFTBCZZUBAKN-UHFFFAOYSA-N pratosartan Chemical compound CCCC1=NC=2CCCCC(=O)C=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 KCTFTBCZZUBAKN-UHFFFAOYSA-N 0.000 claims 1
- 229960001989 prenylamine Drugs 0.000 claims 1
- 229960001455 quinapril Drugs 0.000 claims 1
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 claims 1
- 229960003042 quinapril hydrochloride Drugs 0.000 claims 1
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 claims 1
- FLSLEGPOVLMJMN-YSSFQJQWSA-N quinaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)C(O)=O)CC1=CC=CC=C1 FLSLEGPOVLMJMN-YSSFQJQWSA-N 0.000 claims 1
- 229960001007 quinaprilat Drugs 0.000 claims 1
- KEDYTOTWMPBSLG-HILJTLORSA-N ramiprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 KEDYTOTWMPBSLG-HILJTLORSA-N 0.000 claims 1
- 229960002231 ramiprilat Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229950003367 semotiadil Drugs 0.000 claims 1
- TVTJZMHAIQQZTL-WATAJHSMSA-M sodium;(2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate Chemical compound [Na+].C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C([O-])=O)CCCC1=CC=CC=C1 TVTJZMHAIQQZTL-WATAJHSMSA-M 0.000 claims 1
- FMMDBLMCSDRUPA-BPUTZDHNSA-N spiraprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)C(O)=O)CC1=CC=CC=C1 FMMDBLMCSDRUPA-BPUTZDHNSA-N 0.000 claims 1
- 229950006297 spiraprilat Drugs 0.000 claims 1
- 108700006892 spiraprilat Proteins 0.000 claims 1
- 229960005187 telmisartan Drugs 0.000 claims 1
- UISARWKNNNHPGI-UHFFFAOYSA-N terodiline Chemical compound C=1C=CC=CC=1C(CC(C)NC(C)(C)C)C1=CC=CC=C1 UISARWKNNNHPGI-UHFFFAOYSA-N 0.000 claims 1
- 229960005383 terodiline Drugs 0.000 claims 1
- 229960002051 trandolapril Drugs 0.000 claims 1
- AHYHTSYNOHNUSH-HXFGRODQSA-N trandolaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 AHYHTSYNOHNUSH-HXFGRODQSA-N 0.000 claims 1
- 229960002651 trandolaprilat Drugs 0.000 claims 1
- 229960002769 zofenopril Drugs 0.000 claims 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 claims 1
- 229950001300 zofenoprilat Drugs 0.000 claims 1
- UQWLOWFDKAFKAP-WXHSDQCUSA-N zofenoprilat Chemical compound C1[C@@H](C(O)=O)N(C(=O)[C@@H](CS)C)C[C@H]1SC1=CC=CC=C1 UQWLOWFDKAFKAP-WXHSDQCUSA-N 0.000 claims 1
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Claims (8)
1. Farmaceutski sastav, naznačen time, da obuhvaća sljedeće:
(a) spoj 2-((1-benzil-3-indazolil)metoksi)-2-metil-propionske kiseline, koji ima sljedeću strukturnu formulu:
[image]
(b) najmanje jedno od (i) sredstvo za smanjenje tlaka odabrano od ACE-inhibitora, od sredstava ARB i CCB, i/ili (ii) sredstvo za sniženje kolesterola odabrano od derivata statina, ili njihova bilo koja farmaceutski prihvatljiva sol i njihov takav ester, i
(c) najmanje jedan farmaceutski prikladan nosač;
gdje
navedeni ACE-inhibitor je odabran iz skupine koju čine alacepril, altiopril-kalcij, benzoilkaptopril, kaptopril, kaptopril-cistein, kaptopril-glutation, ceronapril, konverstatin, enalapril, enalaprilat, epikaptopril, fosinopril, fosinopril-natrij, fosinoprilat, hemorfin-4, indolapril, indolaprilat, lizinopril, moveltipril, pentopril, perindopril, perindoprilat, kvinapril, kvinapril-hidroklorid, kvinaprilat, ramipril, ramiprilat, spirapril, spirapril-hidroklorid, spiraprilat, trandolapril, trandolaprilat, zabicipril, zabiciprilat, zofenopril, zofenoprilat,
dok je navedeni ARB odabran iz skupine koju čine kandesartan, cileksetil, irbesartan, losartan, olmesartan, telmisartan, valsartan i pratosartan,
a navedeni CCB je odabran iz skupine koju čine amlodipin, aranidipin, barnidipin, benidipin, kilnidipin, efonidipin, elgodipin, felodipin, izradipin, lacidipin, lerkanidipin, manidipin, nikardipin, nifedipin, nilvadipin, nimodipin, nisoldipin, nitrendipin, diltiazem, klentiazem, bepridil, benciklan, etafenon, flunarizin, lidoflazin, lomerizin, mibefradil, fendilin, prenilamin, semotiadil, terodilin, galopamil i verapamil,
te je derivat statina odabran iz skupine koju čine lovastatin, mevastatin, pravastatin i simvastatin.
2. Farmaceutski sastav prema zahtjevu 1, naznačen time, da je navedeni ACE-inhibitor odabran iz skupine koju čine kaptopril, enalapril, lizinopril, ramipril i perindopril.
3. Farmaceutski sastav prema zahtjevu 1, naznačen time, da je navedeni ARB odabran iz skupine koju čine kandesartan, irbesartan, losartan i valsartan.
4. Farmaceutski sastav prema zahtjevu 1, naznačen time, da je navedeni CCB odabran iz skupine koju čine amlodipin, barnidipin, felodipin, izradipin, lacidipin, lerkanidipin, manidipin, nikardipin, nifedipin, nimodipin,
nisoldipin, nitrendipin, diltiazem, galopamil i verapamil.
5. Farmaceutski sastav prema zahtjevu 1, naznačen time, da je navedeni CCB odabran iz skupine koju čine amlodipin, verapamil i diltiazem.
6. Farmaceutski sastav prema zahtjevu 1, naznačen time, da je navedeni derivat statina odabran iz skupine koju čine lovastatin, pravastatin i simvastatin.
7. Farmaceutski sastav prema bilo kojem od prethodnih zahtjeva,
naznačen time, da navedeni farmaceutski sastav obuhvaća od 300 do 1200 mg bindarita, i jednu količinu od najmanje jednog spoja odabranog iz skupine koju čine ramipril, losartan, irbesartan, amlodipin, verapamil, diltiazem i simvastatin, prema prikazanim vrijednostima u sljedećoj tablici A1:
TABLICA A1
[image]
8. Farmaceutski sastav prema zahtjevu 7, naznačen time, da navedeni farmaceutski sastav obuhvaća maseni omjer između količine bindarita i količine od navedenog najmanje jednog spoja, kako slijedi prema prikazanim vrijednostima u tablici A2:
TABLICA A2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09425368 | 2009-09-23 | ||
| PCT/EP2010/062979 WO2011036047A1 (en) | 2009-09-23 | 2010-09-03 | Pharmaceutical composition for the treatment of mcp-1 mediated inflammatory diseases |
| EP10747897.6A EP2480224B1 (en) | 2009-09-23 | 2010-09-03 | Pharmaceutical composition for the treatment of mcp-1 mediated inflammatory diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171209T1 true HRP20171209T1 (hr) | 2017-10-20 |
Family
ID=41722750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171209TT HRP20171209T1 (hr) | 2009-09-23 | 2017-08-07 | Farmaceutski pripravak za liječenje upalnih bolesti posredovanih putem mcp-1 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US9492542B2 (hr) |
| EP (1) | EP2480224B1 (hr) |
| JP (2) | JP2013505278A (hr) |
| KR (1) | KR101774402B1 (hr) |
| CN (1) | CN102573827B (hr) |
| AR (1) | AR078307A1 (hr) |
| AU (1) | AU2010297405B2 (hr) |
| BR (1) | BR112012006149A2 (hr) |
| CA (1) | CA2760180C (hr) |
| CY (1) | CY1119125T1 (hr) |
| DK (1) | DK2480224T3 (hr) |
| EA (1) | EA021485B1 (hr) |
| ES (1) | ES2637024T3 (hr) |
| GE (1) | GEP20146067B (hr) |
| HR (1) | HRP20171209T1 (hr) |
| HU (1) | HUE033102T2 (hr) |
| IL (1) | IL218001A (hr) |
| LT (1) | LT2480224T (hr) |
| MX (1) | MX347957B (hr) |
| PL (1) | PL2480224T3 (hr) |
| PT (1) | PT2480224T (hr) |
| SG (2) | SG10201405408YA (hr) |
| SI (1) | SI2480224T1 (hr) |
| UA (1) | UA108742C2 (hr) |
| WO (1) | WO2011036047A1 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2262778T (pt) | 2008-03-07 | 2019-11-19 | Acraf | Derivados de 1-benzil-3-hidroximetilindazolo e utilização dos mesmos no tratamento de doenças baseadas na expressão de mcp-1, cxcr1 e p40 |
| JP5509102B2 (ja) | 2008-03-07 | 2014-06-04 | アジェンデ・キミケ・リウニテ・アンジェリニ・フランチェスコ・ア・チ・エレ・ア・エフェ・ソシエタ・ペル・アチオニ | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体およびそのｍｃｐ−１およびｃｘ３ｃｒ１の発現に基づく疾患の治療への使用 |
| US8999292B2 (en) | 2012-05-01 | 2015-04-07 | Translatum Medicus Inc. | Methods for treating and diagnosing blinding eye diseases |
| US11221321B2 (en) * | 2019-05-29 | 2022-01-11 | Imam Abdulrahman Bin Faisal University | Liquid chromatographic method for the simultaneous analysis of antihypertensive and antilipidemic agents and interactions thereof |
| EP3990433A4 (en) | 2019-06-25 | 2023-07-26 | Translatum Medicus Inc. | METHODS FOR THE MANUFACTURE OF 2-((1-BENZYL-1H-INDAZOL-3-YL)METHOXY)-2-METHYLPROPANOIC ACID AND ITS DERIVATIVES |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI88400C (fi) | 1984-08-06 | 1993-05-10 | Upjohn Co | Foerfarande foer framstaellning av renin inhiberande peptider |
| MY103189A (en) | 1986-10-31 | 1993-05-29 | Pfizer | Nor-statine and nor-cyclostatine polypeptides |
| US4927807A (en) | 1987-10-06 | 1990-05-22 | Abbott Laboratories | Glaucoma treatment |
| IT1230441B (it) | 1989-02-07 | 1991-10-23 | Acraf | Eteri della serie dell'indazolo |
| CA2023099A1 (en) | 1989-09-04 | 1991-03-05 | Quirico Branca | Amino acid derivatives |
| US5209933A (en) | 1990-01-10 | 1993-05-11 | Syntex (U.S.A.) Inc. | Long acting calcium channel blocker composition |
| IE68045B1 (en) | 1990-05-11 | 1996-05-15 | Abbott Lab | Renin inhibitors |
| TW198712B (hr) | 1991-04-17 | 1993-01-21 | Hoffmann La Roche | |
| IT1253703B (it) | 1991-04-22 | 1995-08-23 | Angelini Francesco Ist Ricerca | Uso di acidi metossi alcanoici dell'indazolo per preparare un farmaco attivo nel trattamento di malattie autoimmunitarie |
| MY119161A (en) | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
| US5994348A (en) * | 1995-06-07 | 1999-11-30 | Sanofi | Pharmaceutical compositions containing irbesartan |
| IT1276031B1 (it) | 1995-10-31 | 1997-10-24 | Angelini Ricerche Spa | Composizione farmaceutica per il trattamento delle malattie autoimmuni |
| SE9600120D0 (sv) | 1996-01-15 | 1996-01-15 | Astra Ab | Novel medical use |
| IT1293795B1 (it) * | 1997-07-28 | 1999-03-10 | Angelini Ricerche Spa | Farmaco attivo nel ridurre la produzione di proteina mcp-1 |
| US6268377B1 (en) | 1998-09-28 | 2001-07-31 | Merck & Co., Inc. | Method for treating androgen-related conditions |
| GB0111077D0 (en) | 2001-05-04 | 2001-06-27 | Biochemie Gmbh | Organic compounds |
| US20030073705A1 (en) | 2001-05-14 | 2003-04-17 | Shahnaz Shahinfar | Method of treatment |
| US20030060501A1 (en) | 2001-09-19 | 2003-03-27 | Francois Mach | Facilitating tissue grafts with statins (HMG-COa reductase inhibitors) |
| US7183285B2 (en) | 2004-04-29 | 2007-02-27 | Pharmix Corp. | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US20070060549A1 (en) | 2004-08-10 | 2007-03-15 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| US20060046996A1 (en) | 2004-08-31 | 2006-03-02 | Kowa Co., Ltd. | Method for treating hyperlipidemia |
| CN101052402A (zh) | 2004-10-29 | 2007-10-10 | 兴和株式会社 | 肾小球疾病治疗剂 |
| CN101365438A (zh) | 2006-02-07 | 2009-02-11 | 持田制药株式会社 | 预防中风复发的组合物 |
| WO2008084504A2 (en) | 2007-01-12 | 2008-07-17 | Rubicon Research Private Limited | Pharmaceutical compositions of angiotensin ii receptor blockers |
| CA2679446C (en) * | 2007-03-01 | 2016-05-17 | Probiodrug Ag | New use of glutaminyl cyclase inhibitors |
| JP5509102B2 (ja) | 2008-03-07 | 2014-06-04 | アジェンデ・キミケ・リウニテ・アンジェリニ・フランチェスコ・ア・チ・エレ・ア・エフェ・ソシエタ・ペル・アチオニ | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体およびそのｍｃｐ−１およびｃｘ３ｃｒ１の発現に基づく疾患の治療への使用 |
| PL2254870T3 (pl) * | 2008-03-07 | 2016-07-29 | Acraf | Pochodne 1-benzylo-3-hydroksymetyloindazolu i ich zastosowanie w leczeniu chorób opartych na ekspresji MCP-1, CX3CR1 |
| PT2262778T (pt) | 2008-03-07 | 2019-11-19 | Acraf | Derivados de 1-benzil-3-hidroximetilindazolo e utilização dos mesmos no tratamento de doenças baseadas na expressão de mcp-1, cxcr1 e p40 |
-
2010
- 2010-03-09 UA UAA201203482A patent/UA108742C2/uk unknown
- 2010-09-03 SI SI201031512T patent/SI2480224T1/sl unknown
- 2010-09-03 BR BR112012006149A patent/BR112012006149A2/pt not_active Application Discontinuation
- 2010-09-03 PL PL10747897T patent/PL2480224T3/pl unknown
- 2010-09-03 WO PCT/EP2010/062979 patent/WO2011036047A1/en active Application Filing
- 2010-09-03 CA CA2760180A patent/CA2760180C/en not_active Expired - Fee Related
- 2010-09-03 LT LTEP10747897.6T patent/LT2480224T/lt unknown
- 2010-09-03 DK DK10747897.6T patent/DK2480224T3/en active
- 2010-09-03 CN CN201080042390.9A patent/CN102573827B/zh not_active Expired - Fee Related
- 2010-09-03 AU AU2010297405A patent/AU2010297405B2/en not_active Ceased
- 2010-09-03 EP EP10747897.6A patent/EP2480224B1/en active Active
- 2010-09-03 JP JP2012530204A patent/JP2013505278A/ja active Pending
- 2010-09-03 EA EA201270449A patent/EA021485B1/ru not_active IP Right Cessation
- 2010-09-03 SG SG10201405408YA patent/SG10201405408YA/en unknown
- 2010-09-03 GE GEAP201012675A patent/GEP20146067B/en unknown
- 2010-09-03 HU HUE10747897A patent/HUE033102T2/en unknown
- 2010-09-03 ES ES10747897.6T patent/ES2637024T3/es active Active
- 2010-09-03 KR KR1020127007411A patent/KR101774402B1/ko active IP Right Grant
- 2010-09-03 SG SG2012010302A patent/SG178414A1/en unknown
- 2010-09-03 PT PT107478976T patent/PT2480224T/pt unknown
- 2010-09-03 US US13/497,175 patent/US9492542B2/en active Active
- 2010-09-03 MX MX2012003485A patent/MX347957B/es active IP Right Grant
- 2010-09-22 AR ARP100103447A patent/AR078307A1/es unknown
-
2012
- 2012-02-09 IL IL218001A patent/IL218001A/en not_active IP Right Cessation
-
2015
- 2015-07-31 JP JP2015152596A patent/JP6122470B2/ja active Active
-
2017
- 2017-07-28 CY CY20171100808T patent/CY1119125T1/el unknown
- 2017-08-07 HR HRP20171209TT patent/HRP20171209T1/hr unknown
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