HRP20120167T1 - Heteroarilom supstituirani amidi koji sadrže zasićenu spojnicu i njihova upotreba kao farmaceutska sredstva - Google Patents
Heteroarilom supstituirani amidi koji sadrže zasićenu spojnicu i njihova upotreba kao farmaceutska sredstva Download PDFInfo
- Publication number
- HRP20120167T1 HRP20120167T1 HR20120167T HRP20120167T HRP20120167T1 HR P20120167 T1 HRP20120167 T1 HR P20120167T1 HR 20120167 T HR20120167 T HR 20120167T HR P20120167 T HRP20120167 T HR P20120167T HR P20120167 T1 HRP20120167 T1 HR P20120167T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- pyridin
- substituted
- alkyloxy
- dione
- Prior art date
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- 239000003814 drug Substances 0.000 title claims 3
- 150000001408 amides Chemical class 0.000 title 1
- 125000005647 linker group Chemical group 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 67
- 125000001424 substituent group Chemical group 0.000 claims abstract 40
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 35
- 229910052736 halogen Inorganic materials 0.000 claims abstract 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 29
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 22
- 150000002367 halogens Chemical class 0.000 claims abstract 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 19
- -1 pyridinediyl Chemical group 0.000 claims abstract 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 11
- 229910052731 fluorine Chemical group 0.000 claims abstract 10
- 239000011737 fluorine Chemical group 0.000 claims abstract 10
- 125000005843 halogen group Chemical group 0.000 claims abstract 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 7
- 125000004429 atom Chemical group 0.000 claims abstract 6
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 5
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 15
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- HSJZYKQURKAJQK-UHFFFAOYSA-N 1-[2-(6-naphthalen-1-ylpyridin-3-yl)oxyethyl]pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CCOC1=CC=C(C=2C3=CC=CC=C3C=CC=2)N=C1 HSJZYKQURKAJQK-UHFFFAOYSA-N 0.000 claims 1
- CNAZQJHTBNTVGH-UHFFFAOYSA-N 1-[2-(6-naphthalen-2-ylpyridin-3-yl)oxyethyl]pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CCOC1=CC=C(C=2C=C3C=CC=CC3=CC=2)N=C1 CNAZQJHTBNTVGH-UHFFFAOYSA-N 0.000 claims 1
- ASOUFWJYKQEBLA-UHFFFAOYSA-N 1-[2-(6-pyridin-3-ylpyridin-3-yl)oxyethyl]pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CCOC1=CC=C(C=2C=NC=CC=2)N=C1 ASOUFWJYKQEBLA-UHFFFAOYSA-N 0.000 claims 1
- WBDAZYIJYCKIQT-UHFFFAOYSA-N 1-[2-(6-pyrimidin-5-ylpyridin-3-yl)oxyethyl]pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CCOC1=CC=C(C=2C=NC=NC=2)N=C1 WBDAZYIJYCKIQT-UHFFFAOYSA-N 0.000 claims 1
- QKQWMCPVTGEYLI-UHFFFAOYSA-N 1-[2-[5-(2-fluorophenyl)pyridin-2-yl]oxyethyl]pyrrolidin-2-one Chemical compound FC1=CC=CC=C1C(C=N1)=CC=C1OCCN1C(=O)CCC1 QKQWMCPVTGEYLI-UHFFFAOYSA-N 0.000 claims 1
- LIWBZOFPTIHIAB-UHFFFAOYSA-N 1-[2-[6-(2,3-dichlorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound ClC1=CC=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1Cl LIWBZOFPTIHIAB-UHFFFAOYSA-N 0.000 claims 1
- KYBHEZTTZPPARO-UHFFFAOYSA-N 1-[2-[6-(2,4-difluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC1=CC(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O KYBHEZTTZPPARO-UHFFFAOYSA-N 0.000 claims 1
- ZXZVYJRJZLGJTQ-UHFFFAOYSA-N 1-[2-[6-(2,5-difluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC1=CC=C(F)C(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 ZXZVYJRJZLGJTQ-UHFFFAOYSA-N 0.000 claims 1
- NGEHZCHNBNMIKO-UHFFFAOYSA-N 1-[2-[6-(2-fluorophenyl)pyridin-3-yl]oxyethyl]azetidin-2-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CC1 NGEHZCHNBNMIKO-UHFFFAOYSA-N 0.000 claims 1
- NQTZQAQIARQHKC-UHFFFAOYSA-N 1-[2-[6-(2-fluorophenyl)pyridin-3-yl]oxyethyl]piperidin-2-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCCC1 NQTZQAQIARQHKC-UHFFFAOYSA-N 0.000 claims 1
- YPIQGBPULOKXDY-UHFFFAOYSA-N 1-[2-[6-(2-fluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O YPIQGBPULOKXDY-UHFFFAOYSA-N 0.000 claims 1
- OHQFUVSKROYBDE-UHFFFAOYSA-N 1-[2-[6-(2-fluoropyridin-3-yl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC1=NC=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O OHQFUVSKROYBDE-UHFFFAOYSA-N 0.000 claims 1
- CPOCSJVIALVNQU-UHFFFAOYSA-N 1-[2-[6-(3,4,5-trifluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC1=C(F)C(F)=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 CPOCSJVIALVNQU-UHFFFAOYSA-N 0.000 claims 1
- RZQRADIOKVNLFM-UHFFFAOYSA-N 1-[2-[6-(3,4-difluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=C(F)C(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O RZQRADIOKVNLFM-UHFFFAOYSA-N 0.000 claims 1
- MSRGHOCDMCNLBX-UHFFFAOYSA-N 1-[2-[6-(3,4-dimethoxyphenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O MSRGHOCDMCNLBX-UHFFFAOYSA-N 0.000 claims 1
- FSKFZBKDRAMBKW-UHFFFAOYSA-N 1-[2-[6-(3,5-dichlorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound ClC1=CC(Cl)=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 FSKFZBKDRAMBKW-UHFFFAOYSA-N 0.000 claims 1
- AXBXKACDIDKSGC-UHFFFAOYSA-N 1-[2-[6-(3,5-difluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC1=CC(F)=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 AXBXKACDIDKSGC-UHFFFAOYSA-N 0.000 claims 1
- IKAVZYYFUHRLQU-UHFFFAOYSA-N 1-[2-[6-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound CC1=NOC(C)=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O IKAVZYYFUHRLQU-UHFFFAOYSA-N 0.000 claims 1
- FNBJLEQSAVSNPI-UHFFFAOYSA-N 1-[2-[6-(3-chloro-4-fluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=C(Cl)C(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O FNBJLEQSAVSNPI-UHFFFAOYSA-N 0.000 claims 1
- QMNWLFLFYIQRFG-UHFFFAOYSA-N 1-[2-[6-(3-chloropyridin-4-yl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound ClC1=CN=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O QMNWLFLFYIQRFG-UHFFFAOYSA-N 0.000 claims 1
- JPNXWMSUFJGVKE-UHFFFAOYSA-N 1-[2-[6-(3-fluoropyridin-4-yl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC1=CN=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O JPNXWMSUFJGVKE-UHFFFAOYSA-N 0.000 claims 1
- GCOODUBEBPVLGW-UHFFFAOYSA-N 1-[2-[6-(4-ethoxyphenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=CC(OCC)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O GCOODUBEBPVLGW-UHFFFAOYSA-N 0.000 claims 1
- FWQCSRKKYDXBJB-UHFFFAOYSA-N 1-[2-[6-(4-fluoro-2-methylphenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound CC1=CC(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O FWQCSRKKYDXBJB-UHFFFAOYSA-N 0.000 claims 1
- ZKRQEZSJFATACG-UHFFFAOYSA-N 1-[2-[6-(4-fluoro-3-methylphenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=C(F)C(C)=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 ZKRQEZSJFATACG-UHFFFAOYSA-N 0.000 claims 1
- NYKUOEHGVDJNTP-UHFFFAOYSA-N 1-[2-[6-(4-fluorophenyl)pyridin-3-yl]oxyethyl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)C=CC=C1 NYKUOEHGVDJNTP-UHFFFAOYSA-N 0.000 claims 1
- BEBUJPUYZBGOQZ-UHFFFAOYSA-N 1-[2-[6-(4-fluorophenyl)pyridin-3-yl]oxyethyl]pyrrole-2,5-dione Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)C=CC1=O BEBUJPUYZBGOQZ-UHFFFAOYSA-N 0.000 claims 1
- BMCCTPCFPIRPKW-UHFFFAOYSA-N 1-[2-[6-(4-fluorophenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O BMCCTPCFPIRPKW-UHFFFAOYSA-N 0.000 claims 1
- GZVKGAHSKNGCRL-UHFFFAOYSA-N 1-[2-[6-(4-methylthiophen-2-yl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound CC1=CSC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 GZVKGAHSKNGCRL-UHFFFAOYSA-N 0.000 claims 1
- QWIFHWYLEMGQOX-UHFFFAOYSA-N 1-[2-[6-(4-tert-butylphenyl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O QWIFHWYLEMGQOX-UHFFFAOYSA-N 0.000 claims 1
- RFDHDIBQDGJVTE-UHFFFAOYSA-N 1-[2-[6-(6-fluoropyridin-3-yl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=NC(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O RFDHDIBQDGJVTE-UHFFFAOYSA-N 0.000 claims 1
- PAXSIXYVYLBLOO-UHFFFAOYSA-N 1-[2-[6-(6-methoxypyridin-3-yl)pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=NC(OC)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O PAXSIXYVYLBLOO-UHFFFAOYSA-N 0.000 claims 1
- ZBUJWECWURZVLI-UHFFFAOYSA-N 1-[2-[6-[2-(trifluoromethoxy)phenyl]pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC(F)(F)OC1=CC=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O ZBUJWECWURZVLI-UHFFFAOYSA-N 0.000 claims 1
- GXZQOMZABOBSJQ-UHFFFAOYSA-N 1-[2-[6-[2-(trifluoromethyl)phenyl]pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC(F)(F)C1=CC=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O GXZQOMZABOBSJQ-UHFFFAOYSA-N 0.000 claims 1
- NGKUOLKGLDQLPK-UHFFFAOYSA-N 1-[2-[6-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC(F)(F)OC1=CC=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 NGKUOLKGLDQLPK-UHFFFAOYSA-N 0.000 claims 1
- BDQPUVXVBALDDP-UHFFFAOYSA-N 1-[2-[6-[3-(trifluoromethyl)phenyl]pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound FC(F)(F)C1=CC=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 BDQPUVXVBALDDP-UHFFFAOYSA-N 0.000 claims 1
- KKWAPUOVABJBIK-UHFFFAOYSA-N 1-[2-[6-[4-(dimethylamino)phenyl]pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=CC(N(C)C)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O KKWAPUOVABJBIK-UHFFFAOYSA-N 0.000 claims 1
- KZMYEPMXRXYIEG-UHFFFAOYSA-N 1-[2-[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O KZMYEPMXRXYIEG-UHFFFAOYSA-N 0.000 claims 1
- ZZDLMBFWXWSNKW-UHFFFAOYSA-N 1-[2-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxyethyl]pyrrolidine-2,5-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)CCC1=O ZZDLMBFWXWSNKW-UHFFFAOYSA-N 0.000 claims 1
- KYMPPFJXSYBKAO-UHFFFAOYSA-N 1-[2-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]amino]ethyl]imidazolidin-2-one Chemical compound C1=CC(F)=CC=C1C1=CSC(NCCN2C(NCC2)=O)=N1 KYMPPFJXSYBKAO-UHFFFAOYSA-N 0.000 claims 1
- XPJDCZWRPUXTIG-UHFFFAOYSA-N 1-[2-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]amino]ethyl]pyrrolidine-2,5-dione Chemical compound C1=CC(F)=CC=C1C1=CSC(NCCN2C(CCC2=O)=O)=N1 XPJDCZWRPUXTIG-UHFFFAOYSA-N 0.000 claims 1
- AVUPXJHMRLBJAU-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]azepan-2-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCCCC1 AVUPXJHMRLBJAU-UHFFFAOYSA-N 0.000 claims 1
- MMVJIQUSZZSZAO-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]azetidin-2-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CC1 MMVJIQUSZZSZAO-UHFFFAOYSA-N 0.000 claims 1
- GWBGKZYBFLOVCF-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]piperidin-2-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCCC1 GWBGKZYBFLOVCF-UHFFFAOYSA-N 0.000 claims 1
- RWIIWQJEHBEIJN-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]piperidine-2,6-dione Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCCC1=O RWIIWQJEHBEIJN-UHFFFAOYSA-N 0.000 claims 1
- MULMGJCQCLQCOR-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]pyridin-2-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)C=CC=C1 MULMGJCQCLQCOR-UHFFFAOYSA-N 0.000 claims 1
- FBXUGIJTBIOFOY-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]pyrrolidin-2-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCC1 FBXUGIJTBIOFOY-UHFFFAOYSA-N 0.000 claims 1
- KVZHRLYJROSETC-UHFFFAOYSA-N 1-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]pyrrolidine-2,5-dione Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCC1=O KVZHRLYJROSETC-UHFFFAOYSA-N 0.000 claims 1
- VGPSVBCVZJYKHO-UHFFFAOYSA-N 1-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]azepan-2-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCCCC1 VGPSVBCVZJYKHO-UHFFFAOYSA-N 0.000 claims 1
- MXTBJTIXPHOANZ-UHFFFAOYSA-N 1-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]azetidin-2-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CC1 MXTBJTIXPHOANZ-UHFFFAOYSA-N 0.000 claims 1
- SSOZNIGOWZZZQH-UHFFFAOYSA-N 1-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]piperidin-2-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCCC1 SSOZNIGOWZZZQH-UHFFFAOYSA-N 0.000 claims 1
- BQCDCGYCNOHHJI-UHFFFAOYSA-N 1-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]piperidine-2,6-dione Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCCC1=O BQCDCGYCNOHHJI-UHFFFAOYSA-N 0.000 claims 1
- WWPPCIQZRXEOKT-UHFFFAOYSA-N 1-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]pyridin-2-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)C=CC=C1 WWPPCIQZRXEOKT-UHFFFAOYSA-N 0.000 claims 1
- CJMNTPGFQOTGJE-UHFFFAOYSA-N 1-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]pyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCC1 CJMNTPGFQOTGJE-UHFFFAOYSA-N 0.000 claims 1
- WTKGKLZRNCQUKX-UHFFFAOYSA-N 1-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]pyrrolidine-2,5-dione Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CCC1=O WTKGKLZRNCQUKX-UHFFFAOYSA-N 0.000 claims 1
- OIQXPLGUQBVAOW-UHFFFAOYSA-N 3-[2-[6-(2-fluorophenyl)pyridin-3-yl]oxyethyl]imidazolidine-2,4-dione Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1OCCN1C(=O)NCC1=O OIQXPLGUQBVAOW-UHFFFAOYSA-N 0.000 claims 1
- CZZKVBFLEHYBFU-UHFFFAOYSA-N 3-[2-[6-(4-fluorophenyl)pyridin-3-yl]oxyethyl]imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1OCCN1C(=O)NCC1=O CZZKVBFLEHYBFU-UHFFFAOYSA-N 0.000 claims 1
- YJFZXHKBQDDBPD-UHFFFAOYSA-N 3-[2-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]amino]ethyl]imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C1=CSC(NCCN2C(NCC2=O)=O)=N1 YJFZXHKBQDDBPD-UHFFFAOYSA-N 0.000 claims 1
- HXYFMPXQQUWFLZ-UHFFFAOYSA-N 3-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]-1,3-thiazolidine-2,4-dione Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)SCC1=O HXYFMPXQQUWFLZ-UHFFFAOYSA-N 0.000 claims 1
- AYBABRDRFBSFNB-UHFFFAOYSA-N 3-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]imidazolidine-2,4-dione Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)NCC1=O AYBABRDRFBSFNB-UHFFFAOYSA-N 0.000 claims 1
- ULMCZCKYQQRUMG-UHFFFAOYSA-N 3-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)OCC1 ULMCZCKYQQRUMG-UHFFFAOYSA-N 0.000 claims 1
- PMDIPYYMTHMDIJ-UHFFFAOYSA-N 3-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)SCC1=O PMDIPYYMTHMDIJ-UHFFFAOYSA-N 0.000 claims 1
- PEMXZDCTOHCQAU-UHFFFAOYSA-N 3-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)NC(=O)N1CCCC1=CC=C(C=2C=CC(F)=CC=2)N=C1 PEMXZDCTOHCQAU-UHFFFAOYSA-N 0.000 claims 1
- CXOHXDPEHSBBGT-UHFFFAOYSA-N 3-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)NCC1=O CXOHXDPEHSBBGT-UHFFFAOYSA-N 0.000 claims 1
- PFCVTWAOYXTQDC-UHFFFAOYSA-N 3-[5-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]pyridin-2-yl]benzonitrile Chemical compound O=C1CCC(=O)N1CCOC1=CC=C(C=2C=C(C=CC=2)C#N)N=C1 PFCVTWAOYXTQDC-UHFFFAOYSA-N 0.000 claims 1
- UDWVBHXHMWISTI-UHFFFAOYSA-N 4-[3-(6-phenylpyridin-3-yl)propyl]thiomorpholin-3-one Chemical compound O=C1CSCCN1CCCC1=CC=C(C=2C=CC=CC=2)N=C1 UDWVBHXHMWISTI-UHFFFAOYSA-N 0.000 claims 1
- YPJBBXMCCKZEPE-UHFFFAOYSA-N 4-[3-[6-(2-chlorophenyl)pyridin-3-yl]propyl]thiomorpholin-3-one Chemical compound ClC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CSCC1 YPJBBXMCCKZEPE-UHFFFAOYSA-N 0.000 claims 1
- OAXPIOMGNSKPNT-UHFFFAOYSA-N 4-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]-1,4-thiazin-3-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CSC=C1 OAXPIOMGNSKPNT-UHFFFAOYSA-N 0.000 claims 1
- IZQRURBHRVAPIL-UHFFFAOYSA-N 4-[3-[6-(2-fluorophenyl)pyridin-3-yl]propyl]thiomorpholin-3-one Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CSCC1 IZQRURBHRVAPIL-UHFFFAOYSA-N 0.000 claims 1
- BMCJXNPKNJNCRA-UHFFFAOYSA-N 4-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]-1,4-thiazin-3-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CSC=C1 BMCJXNPKNJNCRA-UHFFFAOYSA-N 0.000 claims 1
- NZHVDRPPZAJBHW-UHFFFAOYSA-N 4-[3-[6-(4-fluorophenyl)pyridin-3-yl]propyl]thiomorpholin-3-one Chemical compound C1=CC(F)=CC=C1C(N=C1)=CC=C1CCCN1C(=O)CSCC1 NZHVDRPPZAJBHW-UHFFFAOYSA-N 0.000 claims 1
- NRMPNNPERNHOCL-UHFFFAOYSA-N 4-[5-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]pyridin-2-yl]benzonitrile Chemical compound O=C1CCC(=O)N1CCOC1=CC=C(C=2C=CC(=CC=2)C#N)N=C1 NRMPNNPERNHOCL-UHFFFAOYSA-N 0.000 claims 1
- ITTYDXSBJOBDAR-UHFFFAOYSA-N 5-[5-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]pyridin-2-yl]thiophene-2-carbonitrile Chemical compound O=C1CCC(=O)N1CCOC1=CC=C(C=2SC(=CC=2)C#N)N=C1 ITTYDXSBJOBDAR-UHFFFAOYSA-N 0.000 claims 1
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims 1
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- 201000001068 Prinzmetal angina Diseases 0.000 claims 1
- 201000003099 Renovascular Hypertension Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
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- 201000004239 Secondary hypertension Diseases 0.000 claims 1
- 208000007718 Stable Angina Diseases 0.000 claims 1
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- 201000010099 disease Diseases 0.000 claims 1
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- 229940079593 drug Drugs 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
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- 230000003511 endothelial effect Effects 0.000 claims 1
- 210000003038 endothelium Anatomy 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 230000007087 memory ability Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
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- PYRMMGDIEFGMHP-UHFFFAOYSA-N n-[3-[5-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]pyridin-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2N=CC(OCCN3C(CCC3=O)=O)=CC=2)=C1 PYRMMGDIEFGMHP-UHFFFAOYSA-N 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- 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
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
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- Endocrinology (AREA)
- Hematology (AREA)
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- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05013870A EP1741709A1 (en) | 2005-06-28 | 2005-06-28 | Heteroaryl-substituted amides comprising a saturated linker group, and their use as pharmaceuticals |
PCT/EP2006/005706 WO2007000246A1 (en) | 2005-06-28 | 2006-06-14 | Heteroaryl-substituted amides comprising a saturated linker group, and their use as pharmaceuticals |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20120167T1 true HRP20120167T1 (hr) | 2012-03-31 |
Family
ID=35478793
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20120167T HRP20120167T1 (hr) | 2005-06-28 | 2012-02-20 | Heteroarilom supstituirani amidi koji sadrže zasićenu spojnicu i njihova upotreba kao farmaceutska sredstva |
Country Status (33)
Country | Link |
---|---|
US (1) | US8518976B2 (el) |
EP (2) | EP1741709A1 (el) |
JP (1) | JP5149794B2 (el) |
KR (1) | KR20080027801A (el) |
CN (1) | CN101208328B (el) |
AR (1) | AR054800A1 (el) |
AT (1) | ATE539072T1 (el) |
AU (1) | AU2006264049B2 (el) |
BR (1) | BRPI0613717A2 (el) |
CA (1) | CA2611953A1 (el) |
CY (1) | CY1112869T1 (el) |
DK (1) | DK1899321T3 (el) |
DO (1) | DOP2006000146A (el) |
ES (1) | ES2378894T3 (el) |
GT (1) | GT200600274A (el) |
HK (1) | HK1122551A1 (el) |
HR (1) | HRP20120167T1 (el) |
IL (1) | IL188382A0 (el) |
MA (1) | MA29552B1 (el) |
MX (1) | MX2008000044A (el) |
NO (1) | NO20080523L (el) |
NZ (1) | NZ565041A (el) |
PA (1) | PA8683901A1 (el) |
PE (1) | PE20070102A1 (el) |
PL (1) | PL1899321T3 (el) |
PT (1) | PT1899321E (el) |
RS (1) | RS52266B (el) |
RU (1) | RU2412181C2 (el) |
SI (1) | SI1899321T1 (el) |
TW (1) | TWI378095B (el) |
UY (1) | UY29640A1 (el) |
WO (1) | WO2007000246A1 (el) |
ZA (1) | ZA200710002B (el) |
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EP1939181A1 (en) * | 2006-12-27 | 2008-07-02 | sanofi-aventis | Heteroaryl-substituted carboxamides and use thereof for the stimulation of the expression of NO synthase |
EP2310372B1 (en) | 2008-07-09 | 2012-05-23 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
US8815772B2 (en) | 2012-06-29 | 2014-08-26 | E I Du Pont De Nemours And Company | Fungicidal heterocyclic carboxamides |
EP3722290B1 (en) * | 2013-04-12 | 2023-06-21 | VALENTA-INTELLEKT Limited | Glutarimide derivative, use thereof, pharmaceutical composition based thereon and methods for producing the glutarimide derivative |
RU2552929C1 (ru) * | 2013-11-14 | 2015-06-10 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Фармацевтическая композиция, содержащая производные глутаримидов, и их применение для лечения эозинофильных заболеваний |
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2005
- 2005-06-28 EP EP05013870A patent/EP1741709A1/en not_active Withdrawn
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2006
- 2006-06-14 RS RS20120131A patent/RS52266B/en unknown
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- 2006-06-14 BR BRPI0613717-2A patent/BRPI0613717A2/pt not_active IP Right Cessation
- 2006-06-14 SI SI200631277T patent/SI1899321T1/sl unknown
- 2006-06-14 RU RU2008102966/04A patent/RU2412181C2/ru not_active IP Right Cessation
- 2006-06-14 WO PCT/EP2006/005706 patent/WO2007000246A1/en active Application Filing
- 2006-06-14 PL PL06754352T patent/PL1899321T3/pl unknown
- 2006-06-14 JP JP2008518663A patent/JP5149794B2/ja not_active Expired - Fee Related
- 2006-06-14 DK DK06754352.0T patent/DK1899321T3/da active
- 2006-06-14 ES ES06754352T patent/ES2378894T3/es active Active
- 2006-06-14 CN CN2006800228986A patent/CN101208328B/zh not_active Expired - Fee Related
- 2006-06-14 KR KR1020077030929A patent/KR20080027801A/ko not_active Application Discontinuation
- 2006-06-14 CA CA002611953A patent/CA2611953A1/en not_active Abandoned
- 2006-06-14 PT PT06754352T patent/PT1899321E/pt unknown
- 2006-06-14 AU AU2006264049A patent/AU2006264049B2/en not_active Ceased
- 2006-06-14 AT AT06754352T patent/ATE539072T1/de active
- 2006-06-14 MX MX2008000044A patent/MX2008000044A/es active IP Right Grant
- 2006-06-14 NZ NZ565041A patent/NZ565041A/en not_active IP Right Cessation
- 2006-06-26 GT GT200600274A patent/GT200600274A/es unknown
- 2006-06-26 DO DO2006000146A patent/DOP2006000146A/es unknown
- 2006-06-26 AR ARP060102736A patent/AR054800A1/es not_active Application Discontinuation
- 2006-06-26 TW TW095122876A patent/TWI378095B/zh not_active IP Right Cessation
- 2006-06-27 PE PE2006000748A patent/PE20070102A1/es not_active Application Discontinuation
- 2006-06-28 PA PA20068683901A patent/PA8683901A1/es unknown
- 2006-06-29 UY UY29640A patent/UY29640A1/es not_active Application Discontinuation
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2007
- 2007-11-20 ZA ZA200710002A patent/ZA200710002B/xx unknown
- 2007-12-18 US US11/958,483 patent/US8518976B2/en not_active Expired - Fee Related
- 2007-12-18 MA MA30487A patent/MA29552B1/fr unknown
- 2007-12-24 IL IL188382A patent/IL188382A0/en unknown
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2008
- 2008-01-28 NO NO20080523A patent/NO20080523L/no not_active Application Discontinuation
- 2008-12-12 HK HK08113552.5A patent/HK1122551A1/xx not_active IP Right Cessation
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- 2012-02-20 HR HR20120167T patent/HRP20120167T1/hr unknown
- 2012-03-28 CY CY20121100320T patent/CY1112869T1/el unknown
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