JP2005505535A5 - - Google Patents
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- JP2005505535A5 JP2005505535A5 JP2003522539A JP2003522539A JP2005505535A5 JP 2005505535 A5 JP2005505535 A5 JP 2005505535A5 JP 2003522539 A JP2003522539 A JP 2003522539A JP 2003522539 A JP2003522539 A JP 2003522539A JP 2005505535 A5 JP2005505535 A5 JP 2005505535A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- methoxy
- optionally substituted
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 4-amino-2-methylquinol-6-yl Chemical group 0.000 claims 488
- 125000001424 substituent group Chemical group 0.000 claims 90
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 81
- 125000000623 heterocyclic group Chemical group 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 46
- 125000001309 chloro group Chemical group Cl* 0.000 claims 26
- 125000001153 fluoro group Chemical group F* 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 24
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 22
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 125000001246 bromo group Chemical group Br* 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229920006395 saturated elastomer Polymers 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000005956 isoquinolyl group Chemical group 0.000 claims 10
- 125000005493 quinolyl group Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 8
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 8
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 7
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 6
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000004306 triazinyl group Chemical group 0.000 claims 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 5
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 4
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- KLAKUQBFAVTQQW-UHFFFAOYSA-N 4-quinolin-6-yl-2-N-(3,4,5-trimethoxyphenyl)-1H-pyrimidine-2,4-diamine Chemical compound N1=CC=CC2=CC(=CC=C12)C1(NC(=NC=C1)NC1=CC(=C(C(=C1)OC)OC)OC)N KLAKUQBFAVTQQW-UHFFFAOYSA-N 0.000 claims 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 3
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 3
- FHGHVZKJXBLKMJ-UHFFFAOYSA-N 1-[2-methoxy-4-[[4-(quinolin-3-ylamino)pyrimidin-2-yl]amino]phenyl]-3-pyrrolidin-1-ylpropan-2-one Chemical compound COC1=CC(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)=CC=C1CC(=O)CN1CCCC1 FHGHVZKJXBLKMJ-UHFFFAOYSA-N 0.000 claims 2
- ZCKCQAXSMORVJH-UHFFFAOYSA-N 1-[3,3-dimethyl-6-[[4-(quinolin-3-ylamino)pyrimidin-2-yl]amino]-2h-indol-1-yl]ethanone Chemical compound C1=CC=CC2=CC(NC=3C=CN=C(N=3)NC3=CC=C4C(C)(C)CN(C4=C3)C(=O)C)=CN=C21 ZCKCQAXSMORVJH-UHFFFAOYSA-N 0.000 claims 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 2
- IXSAPURSGZIKPM-UHFFFAOYSA-N 3-pyrimidin-4-ylquinoline Chemical compound C=1C2=CC=CC=C2N=CC=1C1=CC=NC=N1 IXSAPURSGZIKPM-UHFFFAOYSA-N 0.000 claims 2
- DTJAPEZIABVQFP-UHFFFAOYSA-N 4-isoquinolin-3-yl-2-N-(3,4,5-trimethoxyphenyl)-1H-pyrimidine-2,4-diamine Chemical compound C1=NC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=CC(=C(C(=C1)OC)OC)OC)N DTJAPEZIABVQFP-UHFFFAOYSA-N 0.000 claims 2
- FHDPQTHZTKXVCW-UHFFFAOYSA-N 4-n-quinolin-3-yl-2-n-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)=C1 FHDPQTHZTKXVCW-UHFFFAOYSA-N 0.000 claims 2
- GYBIWXCHCBTGJZ-UHFFFAOYSA-N CC1=C(C=C(C(=C1)OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC(F)(F)F)N Chemical compound CC1=C(C=C(C(=C1)OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC(F)(F)F)N GYBIWXCHCBTGJZ-UHFFFAOYSA-N 0.000 claims 2
- FHTUWMWXFOIMDW-UHFFFAOYSA-N CC1=C(C=C(C(=C1)OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC)N Chemical compound CC1=C(C=C(C(=C1)OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC)N FHTUWMWXFOIMDW-UHFFFAOYSA-N 0.000 claims 2
- ZSMVHKNVAMTQBY-UHFFFAOYSA-N CN(CCC=1C=C(C=CC=1OC)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N)C Chemical compound CN(CCC=1C=C(C=CC=1OC)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N)C ZSMVHKNVAMTQBY-UHFFFAOYSA-N 0.000 claims 2
- MGTZKLAOVGADEY-UHFFFAOYSA-N CN1CCN(CC1)C1=CC=C(C=C1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N MGTZKLAOVGADEY-UHFFFAOYSA-N 0.000 claims 2
- NURDJTYBHTXJAJ-UHFFFAOYSA-N COC=1C=C(C=C(C=1OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC(F)(F)F)N Chemical compound COC=1C=C(C=C(C=1OC)OC)C1(NC=CC(=N1)NC=1C=NC2=CC=C(C=C2C=1)OC(F)(F)F)N NURDJTYBHTXJAJ-UHFFFAOYSA-N 0.000 claims 2
- GPBYUURBWXNIHP-UHFFFAOYSA-N COC=1C=C(C=CC=1C1=CN=CO1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N Chemical compound COC=1C=C(C=CC=1C1=CN=CO1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N GPBYUURBWXNIHP-UHFFFAOYSA-N 0.000 claims 2
- SOFYNOMCXZXSKJ-UHFFFAOYSA-N N1(CCCCC1)CCOC1=CC=C(C=C1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N Chemical compound N1(CCCCC1)CCOC1=CC=C(C=C1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N SOFYNOMCXZXSKJ-UHFFFAOYSA-N 0.000 claims 2
- YSDAQRLYNAQAKT-UHFFFAOYSA-N N1(CCOCC1)C1=CC=C(C=N1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N Chemical compound N1(CCOCC1)C1=CC=C(C=N1)C1(NC=CC(=N1)NC=1C=NC2=CC=CC=C2C=1)N YSDAQRLYNAQAKT-UHFFFAOYSA-N 0.000 claims 2
- UHEGWXNCIOAGLJ-UHFFFAOYSA-N O1C=NC=C1C=1C=C(C=CC=1)C1(NC=CC(=N1)NC=1C=C2C=CC=NC2=CC=1)N Chemical compound O1C=NC=C1C=1C=C(C=CC=1)C1(NC=CC(=N1)NC=1C=C2C=CC=NC2=CC=1)N UHEGWXNCIOAGLJ-UHFFFAOYSA-N 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 1
- KUMNUQZUSIYYSI-UHFFFAOYSA-N 2-N,4-di(quinolin-3-yl)-1H-pyrimidine-2,4-diamine Chemical compound N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC=1C=NC2=CC=CC=C2C=1)N KUMNUQZUSIYYSI-UHFFFAOYSA-N 0.000 claims 1
- RTOWKQKISNDKSF-UHFFFAOYSA-N 2-N-(3,4-dimethoxyphenyl)-4-quinolin-3-yl-1H-pyrimidine-2,4-diamine Chemical compound N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=CC(=C(C=C1)OC)OC)N RTOWKQKISNDKSF-UHFFFAOYSA-N 0.000 claims 1
- ZXYZQVYSFPTDKJ-UHFFFAOYSA-N 2-N-(3,4-dimethoxyphenyl)-4-quinolin-6-yl-1H-pyrimidine-2,4-diamine Chemical compound N1=CC=CC2=CC(=CC=C12)C1(NC(=NC=C1)NC1=CC(=C(C=C1)OC)OC)N ZXYZQVYSFPTDKJ-UHFFFAOYSA-N 0.000 claims 1
- UTXOVTTZSJPSAB-UHFFFAOYSA-N 2-N-(4,5-dimethoxy-2-methylphenyl)-4-isoquinolin-3-yl-1H-pyrimidine-2,4-diamine Chemical compound C1=NC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=C(C=C(C(=C1)OC)OC)C)N UTXOVTTZSJPSAB-UHFFFAOYSA-N 0.000 claims 1
- UYFHSODLLKSDLA-UHFFFAOYSA-N 2-N-quinolin-3-yl-4-quinolin-6-yl-1H-pyrimidine-2,4-diamine Chemical compound N1=CC=CC2=CC(=CC=C12)C1(NC(=NC=C1)NC=1C=NC2=CC=CC=C2C=1)N UYFHSODLLKSDLA-UHFFFAOYSA-N 0.000 claims 1
- WPLNQGXOVZEUGW-UHFFFAOYSA-N 2-n-(3,5-dimethoxyphenyl)-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)=C1 WPLNQGXOVZEUGW-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- NNWLZTUCSATJMM-UHFFFAOYSA-N 3-[[4-(naphthalen-2-ylamino)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C4C=CC=CC4=CC=3)C=CN=2)=C1 NNWLZTUCSATJMM-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- JKNBRHLJJZABQI-UHFFFAOYSA-N 4-(1-methoxyisoquinolin-3-yl)-2-N-(3,4,5-trimethoxyphenyl)-1H-pyrimidine-2,4-diamine Chemical compound COC1=NC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=CC(=C(C(=C1)OC)OC)OC)N JKNBRHLJJZABQI-UHFFFAOYSA-N 0.000 claims 1
- RVJYDFFHLBJSDN-UHFFFAOYSA-N 4-(2-methylquinolin-6-yl)-2-N-(3,4,5-trimethoxyphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CC1=NC2=CC=C(C=C2C=C1)C1(NC(=NC=C1)NC1=CC(=C(C(=C1)OC)OC)OC)N RVJYDFFHLBJSDN-UHFFFAOYSA-N 0.000 claims 1
- NQXFNEZBLNNBMG-UHFFFAOYSA-N 4-quinolin-3-yl-2-N-quinolin-6-yl-1H-pyrimidine-2,4-diamine Chemical compound N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC=1C=C2C=CC=NC2=CC=1)N NQXFNEZBLNNBMG-UHFFFAOYSA-N 0.000 claims 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- WOXOVAQJUXBBRF-UHFFFAOYSA-N COC1=CC=CC=C1NC2=NC(C=CN2)(C3=CC4=C(C=C3)N=CC=C4)N Chemical compound COC1=CC=CC=C1NC2=NC(C=CN2)(C3=CC4=C(C=C3)N=CC=C4)N WOXOVAQJUXBBRF-UHFFFAOYSA-N 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- DGYZYDBDRVDHOG-UHFFFAOYSA-N N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=C(C=CC=C1)OC)N Chemical compound N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=C(C=CC=C1)OC)N DGYZYDBDRVDHOG-UHFFFAOYSA-N 0.000 claims 1
- BDRUTAVXYHDDGQ-UHFFFAOYSA-N N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=CC(=C(C=C1)OCC)OCC)N Chemical compound N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=CC(=C(C=C1)OCC)OCC)N BDRUTAVXYHDDGQ-UHFFFAOYSA-N 0.000 claims 1
- NLWGLKDJSAVSBW-UHFFFAOYSA-N N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=CC(=CC=C1)CC)N Chemical compound N1=CC(=CC2=CC=CC=C12)C1(NC(=NC=C1)NC1=CC(=CC=C1)CC)N NLWGLKDJSAVSBW-UHFFFAOYSA-N 0.000 claims 1
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| PCT/US2002/026870 WO2003018021A1 (en) | 2001-08-22 | 2002-08-22 | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
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