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 |
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| KR19970010862 | 1997-03-27 | ||
| KR1997/10862 | 1997-03-27 | ||
| KR19970010863 | 1997-03-27 | ||
| KR97/10862 | 1997-03-27 | ||
| KR1997/10863 | 1997-03-27 | ||
| KR97/10863 | 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) |
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|---|---|
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| JP (1) | JP3176379B2 (enExample) |
| KR (1) | KR100278857B1 (enExample) |
| CN (1) | CN1118464C (enExample) |
| AR (1) | AR012181A1 (enExample) |
| AT (1) | ATE241613T1 (enExample) |
| AU (1) | AU720385B2 (enExample) |
| BR (1) | BR9808070A (enExample) |
| CA (1) | CA2284795C (enExample) |
| DE (1) | DE69815126T2 (enExample) |
| DK (1) | DK1015444T3 (enExample) |
| ES (1) | ES2200324T3 (enExample) |
| HU (1) | HUP0000851A3 (enExample) |
| IN (1) | IN188411B (enExample) |
| PT (1) | PT1015444E (enExample) |
| RU (1) | RU2203894C2 (enExample) |
| TR (1) | TR199902383T2 (enExample) |
| TW (1) | TW542831B (enExample) |
| UY (1) | UY24938A1 (enExample) |
| WO (1) | WO1998043968A1 (enExample) |
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 |
| AU2003254282A1 (en) | 2002-08-01 | 2004-02-23 | Nitromed, Inc. | Nitrosated proton pump inhibitors, compositions and methods of use |
| WO2005009980A1 (en) * | 2003-07-22 | 2005-02-03 | Neurogen Corporation | Substituted pyridin-2-ylamine analogues |
| US7816353B2 (en) * | 2003-10-24 | 2010-10-19 | Exelixis, Inc. | P70S6 kinase modulators and method of use |
| EP1682133A1 (en) | 2003-11-03 | 2006-07-26 | AstraZeneca AB | Imidazo 1,2-a pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| KR101122376B1 (ko) * | 2005-03-09 | 2012-03-26 | 주식회사유한양행 | 신규의 5,6-다이메틸피리미딘 유도체 및 그의 제조방법 |
| JP2009511548A (ja) * | 2005-10-14 | 2009-03-19 | ノイロサーチ アクティーゼルスカブ | 新規ピリミジン−２，４−ジアミン誘導体及び小コンダクタンスのカルシウム依存性カリウムチャネルのモジュレーターとしてのこれらの使用 |
| 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 |
| DK2308877T3 (da) | 2008-08-05 | 2014-04-22 | Daiichi Sankyo Co Ltd | Imidazopyridin-2-on-derivater |
| 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 |
| KR20140003438A (ko) | 2010-11-15 | 2014-01-09 | 카톨리에케 유니버시테이트 루벤 | 항바이러스성 축합 헤테로사이클릭 화합물 |
| MX2014009933A (es) * | 2012-02-17 | 2015-12-16 | Abbvie Inc | Diaminopirimidinas utiles como inhibidores del virus sincitial respiratorio humano (rsv). |
| CN104334565A (zh) | 2012-05-29 | 2015-02-04 | 莫门蒂夫性能材料有限责任公司 | 异氰酸基硅烷的制备 |
| PH12015501130B1 (en) | 2012-11-21 | 2023-01-27 | Ptc Therapeutics Inc | Substituted reverse pyrimidine bmi-1 inhibitors |
| RU2015143517A (ru) | 2013-03-13 | 2017-04-19 | Дженентек, Инк. | Пиразолсодержащие соединения и их применения |
| MX370588B (es) * | 2013-08-30 | 2019-12-16 | Ptc Therapeutics Inc | Inhibidores de la bmi-1 de pirimidina sustituida. |
| 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 |
| SG10202009723PA (en) * | 2016-01-04 | 2020-11-27 | ObsEva SA | Alpha-amino esters of hydroxypropylthiazolidine carboxamide derivative and salt form, crystal polymorph thereof |
| JP7107962B2 (ja) * | 2017-04-05 | 2022-07-27 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | ２－アミノ－５－オキシアルキル－ピリミジン誘導体および望ましくない植物成長を防除するためのその使用 |
| JP2021535198A (ja) | 2018-08-17 | 2021-12-16 | 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 | 膵臓癌を治療する方法 |
| 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 |
| US3980781A (en) | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
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| GB1383409A (en) | 1972-09-09 | 1974-02-12 | Pfizer Ltd | Derivatives of 2-amino- and 4-amino-quinazoline and pharmaceutical compositions containing them |
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| GB8621425D0 (en) * | 1986-09-05 | 1986-10-15 | Smith Kline French Lab | Compounds |
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| US4966622A (en) | 1988-04-12 | 1990-10-30 | Ciba-Geigy Corporation | N-phenyl-N-pyrimidin-2-ylureas |
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| GB8910722D0 (en) | 1989-05-10 | 1989-06-28 | Smithkline Beckman Intercredit | Compounds |
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| GB9012592D0 (en) | 1990-06-06 | 1990-07-25 | Smithkline Beecham Intercredit | Compounds |
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-
1998
- 1998-03-23 IN IN724DE1998 patent/IN188411B/en unknown
- 1998-03-24 RU RU99122603/04A patent/RU2203894C2/ru not_active IP Right Cessation
- 1998-03-24 CN CN98803765A patent/CN1118464C/zh not_active Expired - Fee Related
- 1998-03-24 AU AU65239/98A patent/AU720385B2/en not_active Ceased
- 1998-03-24 JP JP54148798A patent/JP3176379B2/ja not_active Expired - Fee Related
- 1998-03-24 US US09/381,814 patent/US6352993B1/en not_active Expired - Fee Related
- 1998-03-24 TR TR1999/02383T patent/TR199902383T2/xx unknown
- 1998-03-24 EP EP98911242A patent/EP1015444B1/en not_active Expired - Lifetime
- 1998-03-24 CA CA002284795A patent/CA2284795C/en not_active Expired - Fee Related
- 1998-03-24 WO PCT/KR1998/000058 patent/WO1998043968A1/en not_active Ceased
- 1998-03-24 AT AT98911242T patent/ATE241613T1/de not_active IP Right Cessation
- 1998-03-24 HU HU0000851A patent/HUP0000851A3/hu unknown
- 1998-03-24 DE DE69815126T patent/DE69815126T2/de 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 DK DK98911242T patent/DK1015444T3/da active
- 1998-03-24 PT PT98911242T patent/PT1015444E/pt unknown
- 1998-03-26 AR ARP980101380A patent/AR012181A1/es unknown
- 1998-03-26 UY UY24938A patent/UY24938A1/es not_active IP Right Cessation
- 1998-03-27 TW TW087104605A patent/TW542831B/zh not_active IP Right Cessation
- 1998-03-27 KR KR1019980010754A patent/KR100278857B1/ko not_active Expired - Fee Related
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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 |
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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 |
|---|---|
| UY24938A1 (es) | 2001-01-31 |
| HK1026418A1 (en) | 2000-12-15 |
| KR19980080789A (ko) | 1998-11-25 |
| DE69815126T2 (de) | 2004-04-08 |
| AU6523998A (en) | 1998-10-22 |
| CN1118464C (zh) | 2003-08-20 |
| CA2284795A1 (en) | 1998-10-08 |
| IN188411B (enExample) | 2002-09-21 |
| DE69815126D1 (de) | 2003-07-03 |
| TW542831B (en) | 2003-07-21 |
| HUP0000851A3 (en) | 2002-04-29 |
| HUP0000851A1 (hu) | 2001-04-28 |
| WO1998043968A1 (en) | 1998-10-08 |
| CA2284795C (en) | 2004-01-20 |
| TR199902383T2 (xx) | 2000-06-21 |
| AR012181A1 (es) | 2000-09-27 |
| CN1251586A (zh) | 2000-04-26 |
| BR9808070A (pt) | 2000-03-08 |
| ATE241613T1 (de) | 2003-06-15 |
| EP1015444A1 (en) | 2000-07-05 |
| KR100278857B1 (ko) | 2001-01-15 |
| EP1015444B1 (en) | 2003-05-28 |
| JP3176379B2 (ja) | 2001-06-18 |
| PT1015444E (pt) | 2003-10-31 |
| ES2200324T3 (es) | 2004-03-01 |
| JP2000513014A (ja) | 2000-10-03 |
| AU720385B2 (en) | 2000-06-01 |
| DK1015444T3 (da) | 2003-08-18 |
| US6352993B1 (en) | 2002-03-05 |
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