NO321604B1 - Kinazolin-derivater, anvendelse og fremgangsmate for fremstilling derav, samt farmasoytisk preparat - Google Patents
Kinazolin-derivater, anvendelse og fremgangsmate for fremstilling derav, samt farmasoytisk preparat Download PDFInfo
- Publication number
- NO321604B1 NO321604B1 NO20013882A NO20013882A NO321604B1 NO 321604 B1 NO321604 B1 NO 321604B1 NO 20013882 A NO20013882 A NO 20013882A NO 20013882 A NO20013882 A NO 20013882A NO 321604 B1 NO321604 B1 NO 321604B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- methoxy
- yloxy
- quinazoline
- 3alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title abstract description 83
- 230000008569 process Effects 0.000 title abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 228
- 150000001875 compounds Chemical class 0.000 claims abstract description 226
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 155
- 239000001257 hydrogen Substances 0.000 claims abstract description 154
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 107
- 150000003839 salts Chemical class 0.000 claims abstract description 95
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 86
- -1 cyano, amino Chemical group 0.000 claims abstract description 82
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 78
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 60
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 52
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 50
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 50
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 29
- 230000000694 effects Effects 0.000 claims abstract description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 19
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims abstract description 17
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 241001465754 Metazoa Species 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 13
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
- 230000001772 anti-angiogenic effect Effects 0.000 claims abstract description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 112
- 150000002431 hydrogen Chemical class 0.000 claims description 111
- 125000001424 substituent group Chemical group 0.000 claims description 102
- 229910052736 halogen Inorganic materials 0.000 claims description 88
- 150000002367 halogens Chemical class 0.000 claims description 87
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 51
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 50
- 125000004122 cyclic group Chemical group 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 26
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
- 125000002393 azetidinyl group Chemical group 0.000 claims description 24
- 125000004193 piperazinyl group Chemical group 0.000 claims description 24
- 125000003386 piperidinyl group Chemical group 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 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 18
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 18
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 17
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 16
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000004848 alkoxyethyl group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 230000002137 anti-vascular effect Effects 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- RATKYOYWLZOLNN-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-(piperidin-4-ylmethoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCC1CCNCC1 RATKYOYWLZOLNN-UHFFFAOYSA-N 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 241000282412 Homo Species 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- KSYZTLBEZNPWQB-UHFFFAOYSA-N 3-[4-[2-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxyethoxy]piperidin-1-yl]propanenitrile Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCOC1CCN(CCC#N)CC1 KSYZTLBEZNPWQB-UHFFFAOYSA-N 0.000 claims description 3
- ZHWIBBNQOOPMAE-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCN1CCCCC1 ZHWIBBNQOOPMAE-UHFFFAOYSA-N 0.000 claims description 3
- MEBAXCQMZHDHLI-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(2-piperidin-2-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCC1CCCCN1 MEBAXCQMZHDHLI-UHFFFAOYSA-N 0.000 claims description 3
- IFQGZDCTCSXUNK-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(2-pyridin-4-yloxyethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCOC1=CC=NC=C1 IFQGZDCTCSXUNK-UHFFFAOYSA-N 0.000 claims description 3
- JJFONHXJKBVBHW-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 JJFONHXJKBVBHW-UHFFFAOYSA-N 0.000 claims description 3
- GHAQVSSERMFIOD-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 GHAQVSSERMFIOD-UHFFFAOYSA-N 0.000 claims description 3
- FDGLZZQHPXHDGZ-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazoline Chemical compound C1=C2NC=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCOCCOC)=C1 FDGLZZQHPXHDGZ-UHFFFAOYSA-N 0.000 claims description 3
- CPYOLRZYFGXJMZ-UHFFFAOYSA-N 4-[(2,3-dimethyl-1h-indol-5-yl)oxy]-6-methoxy-7-[(1-methylpiperidin-3-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCCN(C)C1 CPYOLRZYFGXJMZ-UHFFFAOYSA-N 0.000 claims description 3
- SUANGBBIESOPQK-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCN1CCCCC1 SUANGBBIESOPQK-UHFFFAOYSA-N 0.000 claims description 3
- KFPBKESUJSJWGU-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCCN1CCCC1 KFPBKESUJSJWGU-UHFFFAOYSA-N 0.000 claims description 3
- AUEYCHJTTCJDQE-UHFFFAOYSA-N 4-[2-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxyethyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN1CCOCC1 AUEYCHJTTCJDQE-UHFFFAOYSA-N 0.000 claims description 3
- SDBHMCYMOMGNFX-UHFFFAOYSA-N 4-[3-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 SDBHMCYMOMGNFX-UHFFFAOYSA-N 0.000 claims description 3
- KCVMXGBFTUIXQZ-UHFFFAOYSA-N 4-[3-[4-(1h-indol-6-yloxy)-6-methoxyquinazolin-7-yl]oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4NC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 KCVMXGBFTUIXQZ-UHFFFAOYSA-N 0.000 claims description 3
- GGRMMRBLTOWVPK-UHFFFAOYSA-N 4-[3-[4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]-1,4-thiazinane 1,1-dioxide Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCCN1CCS(=O)(=O)CC1 GGRMMRBLTOWVPK-UHFFFAOYSA-N 0.000 claims description 3
- XSDHPUDCUTXDOC-UHFFFAOYSA-N 4-[3-[4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]morpholine Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCCN1CCOCC1 XSDHPUDCUTXDOC-UHFFFAOYSA-N 0.000 claims description 3
- RIYQUDOHNPNEGO-UHFFFAOYSA-N 4-[3-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]-1,4-thiazinane 1,1-dioxide Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCS(=O)(=O)CC1 RIYQUDOHNPNEGO-UHFFFAOYSA-N 0.000 claims description 3
- XACHHHFBHKJFTG-UHFFFAOYSA-N 4-[3-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxypropyl]morpholine Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCOCC1 XACHHHFBHKJFTG-UHFFFAOYSA-N 0.000 claims description 3
- JIHDRMRBLXQGCC-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN1CCCCC1 JIHDRMRBLXQGCC-UHFFFAOYSA-N 0.000 claims description 3
- XWZDOLXRLQATMB-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]-7-(2-pyrrolidin-1-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCN1CCCC1 XWZDOLXRLQATMB-UHFFFAOYSA-N 0.000 claims description 3
- BMKBXNMTWNYODF-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 BMKBXNMTWNYODF-UHFFFAOYSA-N 0.000 claims description 3
- VWIOUOMKJGDTHR-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 VWIOUOMKJGDTHR-UHFFFAOYSA-N 0.000 claims description 3
- OTOUXILYJXJWKG-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]-7-(piperidin-4-ylmethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCNCC1 OTOUXILYJXJWKG-UHFFFAOYSA-N 0.000 claims description 3
- WYJRGYROVOJXHG-UHFFFAOYSA-N 6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCN(C)CC1 WYJRGYROVOJXHG-UHFFFAOYSA-N 0.000 claims description 3
- XXXPJLBUNIPWAR-UHFFFAOYSA-N 7-(3-ethylsulfonylpropoxy)-6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazoline Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCCS(=O)(=O)CC)=C1 XXXPJLBUNIPWAR-UHFFFAOYSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- CAINZODQISJWSP-GOSISDBHSA-N (2r)-1-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCCCC1 CAINZODQISJWSP-GOSISDBHSA-N 0.000 claims description 2
- RGMVLDOREVSNEH-QGZVFWFLSA-N (2r)-1-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCCC1 RGMVLDOREVSNEH-QGZVFWFLSA-N 0.000 claims description 2
- BOYNTSOFXPSPNM-LJQANCHMSA-N (2r)-1-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=C(C)NC4=CC=3)=C2C=C1OC)N1CCN(C)CC1 BOYNTSOFXPSPNM-LJQANCHMSA-N 0.000 claims description 2
- RMLKLTNSQXPRTB-GOSISDBHSA-N (2r)-1-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=C(C)NC4=CC=3)=C2C=C1OC)N1CCCC1 RMLKLTNSQXPRTB-GOSISDBHSA-N 0.000 claims description 2
- CAINZODQISJWSP-SFHVURJKSA-N (2s)-1-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCCCC1 CAINZODQISJWSP-SFHVURJKSA-N 0.000 claims description 2
- TUBBLPAJFHZIKS-FQEVSTJZSA-N (2s)-1-[6-methoxy-2-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@H](O)COC1=CC2=NC(OC=3C=C4C=C(C)NC4=CC=3)=NC=C2C=C1OC)N1CCCCC1 TUBBLPAJFHZIKS-FQEVSTJZSA-N 0.000 claims description 2
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Classifications
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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