RU2203894C2 - Новые производные пиримидина (варианты) - Google Patents
Новые производные пиримидина (варианты) Download PDFInfo
- Publication number
- RU2203894C2 RU2203894C2 RU99122603/04A RU99122603A RU2203894C2 RU 2203894 C2 RU2203894 C2 RU 2203894C2 RU 99122603/04 A RU99122603/04 A RU 99122603/04A RU 99122603 A RU99122603 A RU 99122603A RU 2203894 C2 RU2203894 C2 RU 2203894C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- pyrimidine
- fluorophenylamino
- tetrahydroisoquinolin
- dimethyl
- Prior art date
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- 150000003230 pyrimidines Chemical class 0.000 title claims abstract 4
- -1 C1-3- alkoxyethyl Chemical group 0.000 claims abstract 30
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 11
- 239000001257 hydrogen Substances 0.000 claims abstract 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims abstract 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims 2
- 125000004848 alkoxyethyl group Chemical group 0.000 claims 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 2
- UWUFMRVRQVOJTB-UHFFFAOYSA-N 1-o-ethyl 4-o-[2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] butanedioate Chemical compound C1CC2=CC(OC(=O)CCC(=O)OCC)=CC=C2C(C)N1C(C(=C(C)N=1)C)=NC=1NC1=CC=C(F)C=C1 UWUFMRVRQVOJTB-UHFFFAOYSA-N 0.000 claims 1
- SCFRTKXUMORWLL-UHFFFAOYSA-N 1-o-ethyl 4-o-[2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] butanedioate Chemical compound CC1C2=CC(OC(=O)CCC(=O)OCC)=CC=C2CCN1C(C(=C(C)N=1)C)=NC=1NC1=CC=C(F)C=C1 SCFRTKXUMORWLL-UHFFFAOYSA-N 0.000 claims 1
- OQSQWUHAKPOFAG-UHFFFAOYSA-N 1-o-ethyl 4-o-[[2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl] butanedioate Chemical compound N=1C(N2C(C3=CC=CC=C3CC2)C)=C(C)C(COC(=O)CCC(=O)OCC)=NC=1NC1=CC=C(F)C=C1 OQSQWUHAKPOFAG-UHFFFAOYSA-N 0.000 claims 1
- FEOTVFZHCHZXJX-UHFFFAOYSA-N 2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-ol Chemical compound C1CC2=CC(O)=CC=C2C(C)N1C(C(=C(C)N=1)C)=NC=1NC1=CC=C(F)C=C1 FEOTVFZHCHZXJX-UHFFFAOYSA-N 0.000 claims 1
- PFRMYBINSXRVBK-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-5,6-dimethyl-2-(4-methyl-1,3-thiazol-2-yl)-2H-pyrimidin-1-amine Chemical compound CC=1C(=NC(N(C=1C)N)C=1SC=C(N=1)C)N1CC2=CC=CC=C2CC1 PFRMYBINSXRVBK-UHFFFAOYSA-N 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- HAASDWOKLDBJAK-UHFFFAOYSA-N [2-(4-fluoroanilino)-4-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-5-yl]methanol Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(C)N=1)CO)=NC=1NC1=CC=C(F)C=C1 HAASDWOKLDBJAK-UHFFFAOYSA-N 0.000 claims 1
- MXMLBPWGHPXZRW-UHFFFAOYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methanol Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(CO)N=1)C)=NC=1NC1=CC=C(F)C=C1 MXMLBPWGHPXZRW-UHFFFAOYSA-N 0.000 claims 1
- MELAICPHFIDWPI-LUTIACGYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl (2s)-2-amino-3-methylbutanoate Chemical compound N=1C(N2C(C3=CC=CC=C3CC2)C)=C(C)C(COC(=O)[C@@H](N)C(C)C)=NC=1NC1=CC=C(F)C=C1 MELAICPHFIDWPI-LUTIACGYSA-N 0.000 claims 1
- SZMSHCYQLSFGKE-UHFFFAOYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl 2-phenylmethoxyacetate Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(COC(=O)COCC=1C=CC=CC=1)N=1)C)=NC=1NC1=CC=C(F)C=C1 SZMSHCYQLSFGKE-UHFFFAOYSA-N 0.000 claims 1
- LUWOVCPMNSFXCX-UHFFFAOYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl 3-fluorobenzoate Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(COC(=O)C=1C=C(F)C=CC=1)N=1)C)=NC=1NC1=CC=C(F)C=C1 LUWOVCPMNSFXCX-UHFFFAOYSA-N 0.000 claims 1
- JLSRDGFGQUNHGO-UHFFFAOYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl 3-phenylprop-2-enoate Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(COC(=O)C=CC=1C=CC=CC=1)N=1)C)=NC=1NC1=CC=C(F)C=C1 JLSRDGFGQUNHGO-UHFFFAOYSA-N 0.000 claims 1
- ROJIPTRPEZBVEM-UHFFFAOYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl 4-methylbenzoate Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(COC(=O)C=1C=CC(C)=CC=1)N=1)C)=NC=1NC1=CC=C(F)C=C1 ROJIPTRPEZBVEM-UHFFFAOYSA-N 0.000 claims 1
- DULGCBBSWTWAKF-UHFFFAOYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl 4-pentylbenzoate Chemical compound C1=CC(CCCCC)=CC=C1C(=O)OCC1=NC(NC=2C=CC(F)=CC=2)=NC(N2C(C3=CC=CC=C3CC2)C)=C1C DULGCBBSWTWAKF-UHFFFAOYSA-N 0.000 claims 1
- NZVQGOFXUNABDV-UHFFFAOYSA-N [2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]methyl 4-propylbenzoate Chemical compound C1=CC(CCC)=CC=C1C(=O)OCC1=NC(NC=2C=CC(F)=CC=2)=NC(N2C(C3=CC=CC=C3CC2)C)=C1C NZVQGOFXUNABDV-UHFFFAOYSA-N 0.000 claims 1
- UTRGXAOOUSKFCH-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,3,4,5-tetrafluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC(F)=C(F)C(F)=C1F UTRGXAOOUSKFCH-UHFFFAOYSA-N 0.000 claims 1
- HLNJBKUNHKPSIF-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,3,4-trifluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=C(F)C(F)=C1F HLNJBKUNHKPSIF-UHFFFAOYSA-N 0.000 claims 1
- QQWIJYAHRQQLHU-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,3,6-trifluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=C(F)C=CC(F)=C1F QQWIJYAHRQQLHU-UHFFFAOYSA-N 0.000 claims 1
- ZPFZAPAWVYPQQX-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,3-difluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=CC(F)=C1F ZPFZAPAWVYPQQX-UHFFFAOYSA-N 0.000 claims 1
- NABQSPFBADDJQP-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,4,5-trifluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC(F)=C(F)C=C1F NABQSPFBADDJQP-UHFFFAOYSA-N 0.000 claims 1
- IEOHHYXMYBNALF-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,4,6-trichlorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl IEOHHYXMYBNALF-UHFFFAOYSA-N 0.000 claims 1
- LNNUPAGTHMEMDE-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,4-dichloro-5-fluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC(F)=C(Cl)C=C1Cl LNNUPAGTHMEMDE-UHFFFAOYSA-N 0.000 claims 1
- DJWVXDLCIYVNLH-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,4-difluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=C(F)C=C1F DJWVXDLCIYVNLH-UHFFFAOYSA-N 0.000 claims 1
- ZTNBQDWXKIMGFU-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2,6-difluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=C(F)C=CC=C1F ZTNBQDWXKIMGFU-UHFFFAOYSA-N 0.000 claims 1
- QJEIIVUCEMBHTH-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2-(3-methoxyphenyl)acetate Chemical compound COC1=CC=CC(CC(=O)OC=2C=C3CCN(C(C)C3=CC=2)C=2C(=C(C)N=C(NC=3C=CC(F)=CC=3)N=2)C)=C1 QJEIIVUCEMBHTH-UHFFFAOYSA-N 0.000 claims 1
- PRMHQZZFAQHHOP-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2-(4-methoxyphenyl)acetate Chemical compound C1=CC(OC)=CC=C1CC(=O)OC1=CC=C(C(C)N(CC2)C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)C2=C1 PRMHQZZFAQHHOP-UHFFFAOYSA-N 0.000 claims 1
- ZVOANXVHMLFIDF-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2-chlorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=CC=C1Cl ZVOANXVHMLFIDF-UHFFFAOYSA-N 0.000 claims 1
- DQWINXRKSPEREL-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 2-phenylmethoxyacetate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)COCC1=CC=CC=C1 DQWINXRKSPEREL-UHFFFAOYSA-N 0.000 claims 1
- RXVSMDZYRCAYMM-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 3-(trifluoromethyl)benzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=CC(C(F)(F)F)=C1 RXVSMDZYRCAYMM-UHFFFAOYSA-N 0.000 claims 1
- FGAZRMYWUPYJET-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 3-chlorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=CC(Cl)=C1 FGAZRMYWUPYJET-UHFFFAOYSA-N 0.000 claims 1
- GIJCCRIGUVYBSN-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 3-cyanobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=CC(C#N)=C1 GIJCCRIGUVYBSN-UHFFFAOYSA-N 0.000 claims 1
- HNCRBJUZXJFDON-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 3-fluorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=CC(F)=C1 HNCRBJUZXJFDON-UHFFFAOYSA-N 0.000 claims 1
- KSGDVBXJPNXIKX-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 3-phenylprop-2-enoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C=CC1=CC=CC=C1 KSGDVBXJPNXIKX-UHFFFAOYSA-N 0.000 claims 1
- AIKIFAMWBPZEDX-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 4-butoxybenzoate Chemical compound C1=CC(OCCCC)=CC=C1C(=O)OC1=CC=C(C(C)N(CC2)C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)C2=C1 AIKIFAMWBPZEDX-UHFFFAOYSA-N 0.000 claims 1
- KLBZEZIEIVPJGX-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 4-chlorobenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=C(Cl)C=C1 KLBZEZIEIVPJGX-UHFFFAOYSA-N 0.000 claims 1
- MWCOKDSJYBTTDD-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 4-ethylbenzoate Chemical compound C1=CC(CC)=CC=C1C(=O)OC1=CC=C(C(C)N(CC2)C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)C2=C1 MWCOKDSJYBTTDD-UHFFFAOYSA-N 0.000 claims 1
- PWWLUWYTNHXCDJ-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 4-methylbenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=C(C)C=C1 PWWLUWYTNHXCDJ-UHFFFAOYSA-N 0.000 claims 1
- OFCUEKMVHQOVDC-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 4-pentylbenzoate Chemical compound C1=CC(CCCCC)=CC=C1C(=O)OC1=CC=C(C(C)N(CC2)C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)C2=C1 OFCUEKMVHQOVDC-UHFFFAOYSA-N 0.000 claims 1
- ROKRZOVDIJHWIB-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 4-propylbenzoate Chemical compound C1=CC(CCC)=CC=C1C(=O)OC1=CC=C(C(C)N(CC2)C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)C2=C1 ROKRZOVDIJHWIB-UHFFFAOYSA-N 0.000 claims 1
- WJQGMXFNVJFELI-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-6-yl] 4-tert-butylbenzoate Chemical compound C=1C=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=1OC(=O)C1=CC=C(C(C)(C)C)C=C1 WJQGMXFNVJFELI-UHFFFAOYSA-N 0.000 claims 1
- XTGQLXDKMQDORS-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 2,3-difluorobenzoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C1=CC=CC(F)=C1F XTGQLXDKMQDORS-UHFFFAOYSA-N 0.000 claims 1
- PCNQAMUFPURFQL-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 2-(3-methoxyphenyl)acetate Chemical compound COC1=CC=CC(CC(=O)OC=2C=C3C(C)N(CCC3=CC=2)C=2C(=C(C)N=C(NC=3C=CC(F)=CC=3)N=2)C)=C1 PCNQAMUFPURFQL-UHFFFAOYSA-N 0.000 claims 1
- SKLJBQAVAONXEO-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 2-(4-methoxyphenyl)acetate Chemical compound C1=CC(OC)=CC=C1CC(=O)OC1=CC=C(CCN(C2C)C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)C2=C1 SKLJBQAVAONXEO-UHFFFAOYSA-N 0.000 claims 1
- MIUZSFKJCQNNLJ-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 2-chlorobenzoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C1=CC=CC=C1Cl MIUZSFKJCQNNLJ-UHFFFAOYSA-N 0.000 claims 1
- AFCZJUXSPKGQAK-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 2-phenylmethoxyacetate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)COCC1=CC=CC=C1 AFCZJUXSPKGQAK-UHFFFAOYSA-N 0.000 claims 1
- JURVLKRHZDVLSE-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 3-(trifluoromethyl)benzoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C1=CC=CC(C(F)(F)F)=C1 JURVLKRHZDVLSE-UHFFFAOYSA-N 0.000 claims 1
- AEKZJUBETLRWAH-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 3-cyanobenzoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C1=CC=CC(C#N)=C1 AEKZJUBETLRWAH-UHFFFAOYSA-N 0.000 claims 1
- IGHOKMXMBOWXHL-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 3-fluorobenzoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C1=CC=CC(F)=C1 IGHOKMXMBOWXHL-UHFFFAOYSA-N 0.000 claims 1
- OAIZQPXOXWSTFP-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 3-phenylprop-2-enoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C=CC1=CC=CC=C1 OAIZQPXOXWSTFP-UHFFFAOYSA-N 0.000 claims 1
- ILIPORGEJNIDGJ-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 4-methylbenzoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C1=CC=C(C)C=C1 ILIPORGEJNIDGJ-UHFFFAOYSA-N 0.000 claims 1
- RSBGNYFOPWXZBK-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 4-nitrobenzoate Chemical compound C1=C2C(C)N(C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)CCC2=CC=C1OC(=O)C1=CC=C([N+]([O-])=O)C=C1 RSBGNYFOPWXZBK-UHFFFAOYSA-N 0.000 claims 1
- SMJQMCAVHIEZKG-UHFFFAOYSA-N [2-[2-(4-fluoroanilino)-5,6-dimethylpyrimidin-4-yl]-1-methyl-3,4-dihydro-1h-isoquinolin-7-yl] 4-pentylbenzoate Chemical compound C1=CC(CCCCC)=CC=C1C(=O)OC1=CC=C(CCN(C2C)C=3C(=C(C)N=C(NC=4C=CC(F)=CC=4)N=3)C)C2=C1 SMJQMCAVHIEZKG-UHFFFAOYSA-N 0.000 claims 1
- BGBCLJIKHCPCGO-UHFFFAOYSA-N [[2-(4-fluoroanilino)-5-methyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-4-yl]-thiophen-2-ylmethyl] acetate Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(C(OC(C)=O)C=1SC=CC=1)N=1)C)=NC=1NC1=CC=C(F)C=C1 BGBCLJIKHCPCGO-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 102100021904 Potassium-transporting ATPase alpha chain 1 Human genes 0.000 abstract 1
- 108010083204 Proton Pumps Proteins 0.000 abstract 1
- 230000001262 anti-secretory effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000013037 reversible inhibitor Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR19970010863 | 1997-03-27 | ||
| KR1997/10863 | 1997-03-27 | ||
| KR97/10862 | 1997-03-27 | ||
| KR19970010862 | 1997-03-27 | ||
| KR97/10863 | 1997-03-27 | ||
| KR1997/10862 | 1997-03-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99122603A RU99122603A (ru) | 2001-07-27 |
| RU2203894C2 true RU2203894C2 (ru) | 2003-05-10 |
Family
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| RU99122603/04A RU2203894C2 (ru) | 1997-03-27 | 1998-03-24 | Новые производные пиримидина (варианты) |
Country Status (21)
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| EP (1) | EP1015444B1 (show.php) |
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| CN (1) | CN1118464C (show.php) |
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| AT (1) | ATE241613T1 (show.php) |
| AU (1) | AU720385B2 (show.php) |
| BR (1) | BR9808070A (show.php) |
| CA (1) | CA2284795C (show.php) |
| DE (1) | DE69815126T2 (show.php) |
| DK (1) | DK1015444T3 (show.php) |
| ES (1) | ES2200324T3 (show.php) |
| HU (1) | HUP0000851A3 (show.php) |
| IN (1) | IN188411B (show.php) |
| PT (1) | PT1015444E (show.php) |
| RU (1) | RU2203894C2 (show.php) |
| TR (1) | TR199902383T2 (show.php) |
| TW (1) | TW542831B (show.php) |
| UY (1) | UY24938A1 (show.php) |
| WO (1) | WO1998043968A1 (show.php) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2587493C2 (ru) * | 2011-02-25 | 2016-06-20 | Юхан Корпорэйшн | Производные диаминопиримидина и способы их получения |
| RU2587981C2 (ru) * | 2011-02-25 | 2016-06-27 | Юхан Корпорэйшн | Производные диаминопиримидина и способы их получения |
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| KR100272471B1 (ko) | 1998-11-17 | 2000-11-15 | 김선진 | 신규의 피리미딘 유도체 및 그의 제조방법 |
| US6852739B1 (en) | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
| TW200302728A (en) | 2002-02-01 | 2003-08-16 | Novartis Ag | Substituted amines as IgE inhibitors |
| CA2493618A1 (en) | 2002-08-01 | 2004-02-12 | Nitromed, Inc. | Nitrosated proton pump inhibitors, compositions and methods of use |
| AU2004259346A1 (en) * | 2003-07-22 | 2005-02-03 | Neurogen Corporation | Substituted pyridin-2-ylamine analogues |
| WO2005039506A2 (en) * | 2003-10-24 | 2005-05-06 | Exelixis, Inc. | P70s6 kinase modulators and method of use |
| EP1974730A1 (en) | 2003-11-03 | 2008-10-01 | AstraZeneca AB | Imidazo[1,2-a]pyridine derivatives for use in the treatment of sleep disturbance due to silent gastro-esophageal reflux |
| KR101122376B1 (ko) * | 2005-03-09 | 2012-03-26 | 주식회사유한양행 | 신규의 5,6-다이메틸피리미딘 유도체 및 그의 제조방법 |
| US20090124645A1 (en) * | 2005-10-14 | 2009-05-14 | Neurosearch A/S | Novel Pyrimidine-2,4-Diamine Derivatives and their Use as Modulators of Small-Conductance Calcium-Activated Potassium Channels |
| JP4946482B2 (ja) | 2007-02-08 | 2012-06-06 | 船井電機株式会社 | 緩衝用梱包材及びｔｖ受像機の緩衝用梱包材 |
| US8367684B2 (en) * | 2007-06-13 | 2013-02-05 | Valeant Pharmaceuticals International | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
| ES2459047T3 (es) | 2008-08-05 | 2014-05-07 | Daiichi Sankyo Company, Limited | Derivados de imidazopiridin-2-ona |
| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| EP2640705A2 (en) | 2010-11-15 | 2013-09-25 | Katholieke Universiteit Leuven | Novel antiviral compounds |
| MX2014009933A (es) * | 2012-02-17 | 2015-12-16 | Abbvie Inc | Diaminopirimidinas utiles como inhibidores del virus sincitial respiratorio humano (rsv). |
| US9309271B2 (en) | 2012-05-29 | 2016-04-12 | Momentive Performance Materials Gmbh | Preparation of isocyanato silanes |
| TWI623531B (zh) | 2012-11-21 | 2018-05-11 | Ｐｔｃ治療公司 | 經取代反向嘧啶ｂｍｉ－１抑制劑 |
| EP2970307B1 (en) | 2013-03-13 | 2020-03-11 | Genentech, Inc. | Pyrazolo compounds and uses thereof |
| JP6524094B2 (ja) * | 2013-08-30 | 2019-06-05 | ピーティーシー セラピューティクス， インコーポレイテッド | 置換ピリミジンＢｍｉ−１阻害剤 |
| CN104903312B (zh) * | 2013-10-07 | 2019-01-29 | 卡德门企业有限公司 | Rho激酶抑制剂 |
| US10584115B2 (en) | 2013-11-21 | 2020-03-10 | Ptc Therapeutics, Inc. | Substituted pyridine and pyrazine BMI-1 inhibitors |
| WO2016064970A1 (en) * | 2014-10-22 | 2016-04-28 | The Board Of Regents Of The University Of Texas System | Small-molecule inhibitors targeting discoidin domain receptor 1 and uses thereof |
| CN105669642B (zh) * | 2014-11-19 | 2020-06-09 | 江苏天士力帝益药业有限公司 | 一种盐酸洛氟普啶的制备方法 |
| JP6933322B2 (ja) * | 2016-01-04 | 2021-09-08 | メルク セローノ エス．エー． | ヒドロキシプロピルチアゾリジンカルボキサミド誘導体のｌ−バリネート及びその塩形態、結晶多形 |
| EP3606915A1 (de) * | 2017-04-05 | 2020-02-12 | Bayer CropScience Aktiengesellschaft | 2-amino-5-oxyalkyl-pyrimidinderivate und deren verwendung zur bekämpfung unerwünschten pflanzenwachstums |
| US12023335B2 (en) | 2018-08-17 | 2024-07-02 | Ptc Therapeutics, Inc. | Method for treating pancreatic cancer |
| CN114685369B (zh) * | 2022-05-17 | 2024-02-02 | 河南省科学院高新技术研究中心 | 一种利用离子液体制备1-甲基-1,2,3,4-四氢异喹啉的方法 |
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| WO1994014795A1 (en) * | 1992-12-29 | 1994-07-07 | Yuhan Corporation | Quinazoline derivatives |
| WO1995005363A1 (en) * | 1993-08-12 | 1995-02-23 | Astra Aktiebolag | Amidine derivatives with nitric oxide synthetase activities |
| WO1996005177A1 (en) * | 1994-08-13 | 1996-02-22 | Yuhan Corporation | Novel pyrimidine derivatives and processes for the preparation thereof |
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| GB1182584A (en) | 1966-03-31 | 1970-02-25 | Ici Ltd | Pyrimidine derivates and the use thereof as fungicides |
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-
1998
- 1998-03-23 IN IN724DE1998 patent/IN188411B/en unknown
- 1998-03-24 PT PT98911242T patent/PT1015444E/pt unknown
- 1998-03-24 HU HU0000851A patent/HUP0000851A3/hu unknown
- 1998-03-24 RU RU99122603/04A patent/RU2203894C2/ru not_active IP Right Cessation
- 1998-03-24 EP EP98911242A patent/EP1015444B1/en not_active Expired - Lifetime
- 1998-03-24 DK DK98911242T patent/DK1015444T3/da active
- 1998-03-24 CA CA002284795A patent/CA2284795C/en not_active Expired - Fee Related
- 1998-03-24 TR TR1999/02383T patent/TR199902383T2/xx unknown
- 1998-03-24 JP JP54148798A patent/JP3176379B2/ja not_active Expired - Fee Related
- 1998-03-24 ES ES98911242T patent/ES2200324T3/es not_active Expired - Lifetime
- 1998-03-24 BR BR9808070-9A patent/BR9808070A/pt not_active Application Discontinuation
- 1998-03-24 AU AU65239/98A patent/AU720385B2/en not_active Ceased
- 1998-03-24 WO PCT/KR1998/000058 patent/WO1998043968A1/en not_active Ceased
- 1998-03-24 CN CN98803765A patent/CN1118464C/zh not_active Expired - Fee Related
- 1998-03-24 AT AT98911242T patent/ATE241613T1/de not_active IP Right Cessation
- 1998-03-24 DE DE69815126T patent/DE69815126T2/de not_active Expired - Fee Related
- 1998-03-24 US US09/381,814 patent/US6352993B1/en not_active Expired - Fee Related
- 1998-03-26 UY UY24938A patent/UY24938A1/es not_active IP Right Cessation
- 1998-03-26 AR ARP980101380A patent/AR012181A1/es unknown
- 1998-03-27 KR KR1019980010754A patent/KR100278857B1/ko not_active Expired - Fee Related
- 1998-03-27 TW TW087104605A patent/TW542831B/zh not_active IP Right Cessation
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| WO1992018498A1 (en) * | 1991-04-17 | 1992-10-29 | Pfizer Inc. | Pyrimidine derivatives for enhancing antitumor activity |
| WO1994014795A1 (en) * | 1992-12-29 | 1994-07-07 | Yuhan Corporation | Quinazoline derivatives |
| WO1995005363A1 (en) * | 1993-08-12 | 1995-02-23 | Astra Aktiebolag | Amidine derivatives with nitric oxide synthetase activities |
| WO1996005177A1 (en) * | 1994-08-13 | 1996-02-22 | Yuhan Corporation | Novel pyrimidine derivatives and processes for the preparation thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2587493C2 (ru) * | 2011-02-25 | 2016-06-20 | Юхан Корпорэйшн | Производные диаминопиримидина и способы их получения |
| RU2587981C2 (ru) * | 2011-02-25 | 2016-06-27 | Юхан Корпорэйшн | Производные диаминопиримидина и способы их получения |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE241613T1 (de) | 2003-06-15 |
| AR012181A1 (es) | 2000-09-27 |
| CN1118464C (zh) | 2003-08-20 |
| JP2000513014A (ja) | 2000-10-03 |
| AU6523998A (en) | 1998-10-22 |
| AU720385B2 (en) | 2000-06-01 |
| EP1015444B1 (en) | 2003-05-28 |
| US6352993B1 (en) | 2002-03-05 |
| HUP0000851A1 (hu) | 2001-04-28 |
| EP1015444A1 (en) | 2000-07-05 |
| HUP0000851A3 (en) | 2002-04-29 |
| PT1015444E (pt) | 2003-10-31 |
| UY24938A1 (es) | 2001-01-31 |
| WO1998043968A1 (en) | 1998-10-08 |
| TR199902383T2 (xx) | 2000-06-21 |
| JP3176379B2 (ja) | 2001-06-18 |
| CA2284795A1 (en) | 1998-10-08 |
| DE69815126D1 (de) | 2003-07-03 |
| HK1026418A1 (en) | 2000-12-15 |
| TW542831B (en) | 2003-07-21 |
| ES2200324T3 (es) | 2004-03-01 |
| BR9808070A (pt) | 2000-03-08 |
| KR19980080789A (ko) | 1998-11-25 |
| CN1251586A (zh) | 2000-04-26 |
| IN188411B (show.php) | 2002-09-21 |
| DE69815126T2 (de) | 2004-04-08 |
| CA2284795C (en) | 2004-01-20 |
| KR100278857B1 (ko) | 2001-01-15 |
| DK1015444T3 (da) | 2003-08-18 |
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