MXPA05012232A - Nuevos derivados de indol como inhibidores del factor xa. - Google Patents
Nuevos derivados de indol como inhibidores del factor xa.Info
- Publication number
- MXPA05012232A MXPA05012232A MXPA05012232A MXPA05012232A MXPA05012232A MX PA05012232 A MXPA05012232 A MX PA05012232A MX PA05012232 A MXPA05012232 A MX PA05012232A MX PA05012232 A MXPA05012232 A MX PA05012232A MX PA05012232 A MXPA05012232 A MX PA05012232A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- independently
- unsubstituted
- mono
- alkylene
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title description 17
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 10
- 229940123583 Factor Xa inhibitor Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 238000000034 method Methods 0.000 claims abstract description 46
- 230000008569 process Effects 0.000 claims abstract description 21
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 239000003112 inhibitor Substances 0.000 claims abstract description 14
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 13
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
- -1 indoli- it Chemical group 0.000 claims description 551
- 125000000217 alkyl group Chemical group 0.000 claims description 164
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 142
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 135
- 125000000623 heterocyclic group Chemical group 0.000 claims description 134
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 114
- 125000003118 aryl group Chemical group 0.000 claims description 107
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 92
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 92
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 87
- 229910052736 halogen Inorganic materials 0.000 claims description 87
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 84
- 150000002367 halogens Chemical class 0.000 claims description 82
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- 125000002950 monocyclic group Chemical group 0.000 claims description 71
- 125000004122 cyclic group Chemical group 0.000 claims description 69
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 67
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 66
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 66
- 125000002619 bicyclic group Chemical group 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 49
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 45
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 42
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 230000015572 biosynthetic process Effects 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 41
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 41
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 239000011593 sulfur Chemical group 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 229910052760 oxygen Chemical group 0.000 claims description 39
- 239000001301 oxygen Chemical group 0.000 claims description 39
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 37
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 36
- 125000004429 atom Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 36
- 125000001544 thienyl group Chemical group 0.000 claims description 36
- MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 34
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 34
- 125000001041 indolyl group Chemical group 0.000 claims description 34
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 33
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 33
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 32
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 32
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 31
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 30
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 30
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 30
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 30
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 29
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 28
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 28
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 27
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 150000003536 tetrazoles Chemical class 0.000 claims description 26
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 24
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 24
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 24
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 24
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 24
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 24
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 24
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 23
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 23
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 23
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 23
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 22
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 22
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 22
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 22
- 125000002883 imidazolyl group Chemical group 0.000 claims description 22
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 22
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
- 125000000335 thiazolyl group Chemical group 0.000 claims description 22
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 21
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 21
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 21
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 21
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 21
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims description 20
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 20
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 20
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 20
- 125000002971 oxazolyl group Chemical group 0.000 claims description 20
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 19
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 19
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 19
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 19
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 19
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 19
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 18
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 18
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 18
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000002541 furyl group Chemical group 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 15
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 14
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 14
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 14
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 14
- 125000002053 thietanyl group Chemical group 0.000 claims description 14
- 229930192474 thiophene Natural products 0.000 claims description 14
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 13
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 13
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims description 13
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 12
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- CXPUAWQOXQINEX-UHFFFAOYSA-N 1,4-diazocane Chemical compound C1CCNCCNC1 CXPUAWQOXQINEX-UHFFFAOYSA-N 0.000 claims description 11
- ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 claims description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims description 11
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims description 11
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 11
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 11
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 11
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 229960003529 diazepam Drugs 0.000 claims description 11
- WZVHPXGAWGWKTL-UHFFFAOYSA-N diazocan-3-one Chemical compound O=C1CCCCCNN1 WZVHPXGAWGWKTL-UHFFFAOYSA-N 0.000 claims description 11
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- IOJRZKFVJHTXJS-UHFFFAOYSA-N triazetidine Chemical compound C1NNN1 IOJRZKFVJHTXJS-UHFFFAOYSA-N 0.000 claims description 11
- RFOHSZFQYMEWMH-UHFFFAOYSA-N 1,3-diazocan-2-one Chemical compound O=C1NCCCCCN1 RFOHSZFQYMEWMH-UHFFFAOYSA-N 0.000 claims description 10
- CCZDMNTXJXGAEC-UHFFFAOYSA-N 1,3-thiazetidine Chemical compound C1NCS1 CCZDMNTXJXGAEC-UHFFFAOYSA-N 0.000 claims description 10
- BODVRXNXJCWGLR-UHFFFAOYSA-N 2h-1,3-thiazete Chemical compound C1SC=N1 BODVRXNXJCWGLR-UHFFFAOYSA-N 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 10
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 9
- MFVFDTCSVFBOTL-UHFFFAOYSA-N 1,3-diazetidine Chemical compound C1NCN1 MFVFDTCSVFBOTL-UHFFFAOYSA-N 0.000 claims description 9
- AOVLDSGMUKRKDA-UHFFFAOYSA-N 1,3-oxazepane Chemical compound C1CCOCNC1 AOVLDSGMUKRKDA-UHFFFAOYSA-N 0.000 claims description 9
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims description 9
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 9
- QZOUMSXMTWBUKK-UHFFFAOYSA-N 2h-thiazete Chemical compound C1=CSN1 QZOUMSXMTWBUKK-UHFFFAOYSA-N 0.000 claims description 9
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03011306A EP1479677A1 (en) | 2003-05-19 | 2003-05-19 | New indole derivatives as factor xa inhibitors |
| PCT/EP2004/004751 WO2004101554A1 (en) | 2003-05-19 | 2004-05-05 | New indole derivatives as factor xa inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05012232A true MXPA05012232A (es) | 2006-08-18 |
Family
ID=33040953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05012232A MXPA05012232A (es) | 2003-05-19 | 2004-05-05 | Nuevos derivados de indol como inhibidores del factor xa. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7196103B2 (enExample) |
| EP (2) | EP1479677A1 (enExample) |
| JP (1) | JP4676960B2 (enExample) |
| AT (1) | ATE475659T1 (enExample) |
| AU (1) | AU2004238495B2 (enExample) |
| BR (1) | BRPI0410466A (enExample) |
| CA (1) | CA2526066A1 (enExample) |
| CL (1) | CL2004001074A1 (enExample) |
| DE (1) | DE602004028367D1 (enExample) |
| MX (1) | MXPA05012232A (enExample) |
| PA (1) | PA8603601A1 (enExample) |
| PE (1) | PE20050156A1 (enExample) |
| TW (1) | TW200510393A (enExample) |
| UY (1) | UY28325A1 (enExample) |
| WO (1) | WO2004101554A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| US7358268B2 (en) * | 2002-12-04 | 2008-04-15 | Sanofi-Aventis Deutschland Gmbh | Imidazole derivatives as factor Xa inhibitors |
| US7429581B2 (en) | 2002-12-23 | 2008-09-30 | Sanofi-Aventis Deutschland Gmbh | Pyrazole-derivatives as factor Xa inhibitors |
| EP1479675A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Indazole-derivatives as factor Xa inhibitors |
| EP1479677A1 (en) | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | New indole derivatives as factor xa inhibitors |
| US7223780B2 (en) * | 2003-05-19 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Triazole-derivatives as blood clotting enzyme factor Xa inhibitors |
| US7317027B2 (en) * | 2003-05-19 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Azaindole-derivatives as factor Xa inhibitors |
| US7741341B2 (en) | 2003-05-19 | 2010-06-22 | Sanofi-Aventis Deutschland Gmbh | Benzimidazole-derivatives as factor Xa inhibitors |
| EP1571154A1 (en) * | 2004-03-03 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Beta-aminoacid-derivatives as factor Xa inhibitors |
| FR2888847B1 (fr) * | 2005-07-22 | 2007-08-31 | Sanofi Aventis Sa | Derives de n-(heteriaryl)-1-heteorarylalkyl-1h-indole-2- carboxamides, leur preparation et application en therapeutique |
| GB2431927B (en) | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| EP1993559B1 (en) | 2006-02-03 | 2016-06-22 | OPKO Renal, LLC | Treating vitamin d insufficiency and deficiency with 25-hydroxyvitamin d2 and 25-hydroxyvitamin d3 |
| ES2670029T3 (es) | 2006-06-21 | 2018-05-29 | Opko Ireland Global Holdings, Ltd. | Terapia usando agente de repleción de la vitamina D y agente de reemplazo de la hormona de la vitamina D |
| HRP20231142T3 (hr) | 2007-04-25 | 2024-01-05 | Eirgen Pharma Ltd. | Kontrolirano oslobađanje 25-hidroksivitamina d |
| JP2010525080A (ja) | 2007-04-25 | 2010-07-22 | プロヴェンティヴ セラピュティックス リミテッド ライアビリティ カンパニー | 慢性腎臓病における続発性副甲状腺機能亢進症の安全かつ効果的な治療および予防方法 |
| TW200920369A (en) | 2007-10-26 | 2009-05-16 | Amira Pharmaceuticals Inc | 5-lipoxygenase activating protein (flap) inhibitor |
| KR101614723B1 (ko) | 2008-01-11 | 2016-04-22 | 알바니 몰레큘라 리써치, 인크. | Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌 |
| ES2954932T3 (es) | 2008-04-02 | 2023-11-27 | Eirgen Pharma Ltd | Métodos, composiciones, usos y kits útiles para la deficiencia de vitamina D y trastornos relacionados |
| SG190667A1 (en) | 2008-05-23 | 2013-06-28 | Panmira Pharmaceuticals Llc | 5-lipoxygenase-activating protein inhibitor |
| US8546431B2 (en) | 2008-10-01 | 2013-10-01 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| NZ807894A (en) | 2009-04-29 | 2025-08-29 | Amarin Pharmaceuticals Ie Ltd | Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same |
| US8629158B2 (en) * | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| JP2012532144A (ja) * | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| WO2011003021A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| US8618299B2 (en) * | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| WO2011123476A1 (en) | 2010-03-29 | 2011-10-06 | Cytochroma Inc. | Methods and compositions for reducing parathyroid levels |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| KR101847947B1 (ko) | 2013-03-15 | 2018-05-28 | 옵코 아이피 홀딩스 Ⅱ 인코포레이티드 | 안정화되고 변형된 비타민 ｄ 방출 제형 |
| US10220047B2 (en) | 2014-08-07 | 2019-03-05 | Opko Ireland Global Holdings, Ltd. | Adjunctive therapy with 25-hydroxyvitamin D and articles therefor |
| CN108883120A (zh) | 2016-03-28 | 2018-11-23 | 欧普科爱尔兰环球控股有限公司 | 维生素d治疗方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US11469A (en) * | 1854-08-08 | boynton | ||
| US4675332A (en) * | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
| JPH0287282A (ja) * | 1988-09-22 | 1990-03-28 | Nec Corp | グラフ作図レイアウト決定方式 |
| US5506134A (en) | 1990-10-22 | 1996-04-09 | Corvas International, Inc. | Hypridoma and monoclonal antibody which inhibits blood coagulation tissue factor/factor VIIa complex |
| US5788965A (en) | 1991-02-28 | 1998-08-04 | Novo Nordisk A/S | Modified factor VII |
| US5833982A (en) | 1991-02-28 | 1998-11-10 | Zymogenetics, Inc. | Modified factor VII |
| TW229140B (enExample) * | 1992-06-05 | 1994-09-01 | Shell Internat Res Schappej B V | |
| EP1384725A3 (en) | 1994-04-26 | 2007-02-21 | Aventis Pharmaceuticals Inc. | Factor Xa inhibitors |
| FR2763337B1 (fr) * | 1997-05-13 | 1999-08-20 | Sanofi Sa | Nouveaux derives du triazole, un procede pour leur preparation et compositions pharmaceutiques les contenant |
| US20040043995A1 (en) * | 1997-05-13 | 2004-03-04 | Eric Bignon | Novel triazole derivatives, process for their preparation and pharmaceutical compositions containing them |
| RU2225397C2 (ru) * | 1997-12-24 | 2004-03-10 | Авентис Фарма Дойчланд Гмбх | Производные индола как ингибиторы фактора Ха |
| US6608099B1 (en) * | 1998-08-03 | 2003-08-19 | Eli Lilly And Company | Indole sPLA2 inhibitors |
| EP0987274A1 (en) * | 1998-09-15 | 2000-03-22 | Hoechst Marion Roussel Deutschland GmbH | Factor VIIa Inhibitors |
| US6486211B1 (en) * | 1999-10-22 | 2002-11-26 | Smithkline Beecham Corporation | Indole compounds |
| US7053070B2 (en) * | 2000-01-25 | 2006-05-30 | Warner-Lambert Company | Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors |
| US6436965B1 (en) * | 2000-03-02 | 2002-08-20 | Merck Frosst Canada & Co. | PDE IV inhibiting amides, compositions and methods of treatment |
| KR100545507B1 (ko) * | 2000-05-26 | 2006-01-24 | 니뽄 신야쿠 가부시키가이샤 | 복소환 유도체 |
| CN1431999A (zh) * | 2000-05-31 | 2003-07-23 | 阿斯特拉曾尼卡有限公司 | 具有血管损伤活性的吲哚衍生物 |
| WO2001096313A1 (en) * | 2000-06-14 | 2001-12-20 | The Scripps Research Institute | Distamycin a analogs |
| US20030165837A1 (en) * | 2000-06-14 | 2003-09-04 | The Scripps Research Institute | Method for screening DNA binding |
| US6525202B2 (en) * | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| EP1217000A1 (en) * | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| DE10147672A1 (de) * | 2001-09-27 | 2003-04-10 | Bayer Ag | Substituierte 2,5-Diamidoindole und ihre Verwendung |
| US7064135B2 (en) * | 2001-10-12 | 2006-06-20 | Novo Nordisk Inc. | Substituted piperidines |
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| US7358268B2 (en) * | 2002-12-04 | 2008-04-15 | Sanofi-Aventis Deutschland Gmbh | Imidazole derivatives as factor Xa inhibitors |
| US7429581B2 (en) | 2002-12-23 | 2008-09-30 | Sanofi-Aventis Deutschland Gmbh | Pyrazole-derivatives as factor Xa inhibitors |
| US7078419B2 (en) * | 2003-03-10 | 2006-07-18 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cytokine inhibitors |
| US7049323B2 (en) * | 2003-04-25 | 2006-05-23 | Bristol-Myers Squibb Company | Amidoheterocycles as modulators of the melanocortin-4 receptor |
| EP1479677A1 (en) | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | New indole derivatives as factor xa inhibitors |
| US7741341B2 (en) * | 2003-05-19 | 2010-06-22 | Sanofi-Aventis Deutschland Gmbh | Benzimidazole-derivatives as factor Xa inhibitors |
| EP1479675A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Indazole-derivatives as factor Xa inhibitors |
| US7223780B2 (en) * | 2003-05-19 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Triazole-derivatives as blood clotting enzyme factor Xa inhibitors |
| US7405670B2 (en) * | 2005-07-29 | 2008-07-29 | Fitzgerald Timothy W | Method and system for detecting and isolating stray voltage |
-
2003
- 2003-05-19 EP EP03011306A patent/EP1479677A1/en not_active Withdrawn
-
2004
- 2004-05-05 AU AU2004238495A patent/AU2004238495B2/en not_active Expired - Fee Related
- 2004-05-05 BR BRPI0410466-8A patent/BRPI0410466A/pt not_active IP Right Cessation
- 2004-05-05 WO PCT/EP2004/004751 patent/WO2004101554A1/en not_active Ceased
- 2004-05-05 DE DE602004028367T patent/DE602004028367D1/de not_active Expired - Lifetime
- 2004-05-05 AT AT04731170T patent/ATE475659T1/de not_active IP Right Cessation
- 2004-05-05 MX MXPA05012232A patent/MXPA05012232A/es active IP Right Grant
- 2004-05-05 JP JP2006529740A patent/JP4676960B2/ja not_active Expired - Fee Related
- 2004-05-05 EP EP04731170A patent/EP1633746B1/en not_active Expired - Lifetime
- 2004-05-05 CA CA002526066A patent/CA2526066A1/en not_active Abandoned
- 2004-05-14 PE PE2004000500A patent/PE20050156A1/es not_active Application Discontinuation
- 2004-05-17 TW TW093113793A patent/TW200510393A/zh unknown
- 2004-05-17 CL CL200401074A patent/CL2004001074A1/es unknown
- 2004-05-19 US US10/848,743 patent/US7196103B2/en not_active Expired - Lifetime
- 2004-05-19 UY UY28325A patent/UY28325A1/es unknown
- 2004-05-19 PA PA20048603601A patent/PA8603601A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7196103B2 (en) | 2007-03-27 |
| BRPI0410466A (pt) | 2006-05-30 |
| JP4676960B2 (ja) | 2011-04-27 |
| AU2004238495B2 (en) | 2010-07-22 |
| ATE475659T1 (de) | 2010-08-15 |
| UY28325A1 (es) | 2004-12-31 |
| EP1633746B1 (en) | 2010-07-28 |
| EP1479677A1 (en) | 2004-11-24 |
| TW200510393A (en) | 2005-03-16 |
| JP2006528940A (ja) | 2006-12-28 |
| DE602004028367D1 (de) | 2010-09-09 |
| WO2004101554A1 (en) | 2004-11-25 |
| PA8603601A1 (es) | 2004-11-26 |
| CL2004001074A1 (es) | 2005-03-28 |
| US20050033049A1 (en) | 2005-02-10 |
| EP1633746A1 (en) | 2006-03-15 |
| PE20050156A1 (es) | 2005-04-27 |
| AU2004238495A1 (en) | 2004-11-25 |
| CA2526066A1 (en) | 2004-11-25 |
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Legal Events
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| FG | Grant or registration |