JP2005505535A - 抗癌剤として使用するための２，４−二置換ピリミジニル誘導体 - Google Patents

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Publication number

JP2005505535A

JP2005505535A JP2003522539A JP2003522539A JP2005505535A JP 2005505535 A JP2005505535 A JP 2005505535A JP 2003522539 A JP2003522539 A JP 2003522539A JP 2003522539 A JP2003522539 A JP 2003522539A JP 2005505535 A JP2005505535 A JP 2005505535A

Authority

JP

Japan

Prior art keywords

phenyl

methoxy

alkyl

optionally substituted

methyl

Prior art date

2001-08-22

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.)

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• -1 2,4-Disubstituted pyrimidinyl Chemical class 0.000 title claims description 1124
• 239000002246 antineoplastic agent Substances 0.000 title description 20
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• 238000000034 method Methods 0.000 claims abstract description 94
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
• 201000011510 cancer Diseases 0.000 claims abstract description 12
• 125000001424 substituent group Chemical group 0.000 claims description 182
• 239000000203 mixture Substances 0.000 claims description 178
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 151
• 125000000623 heterocyclic group Chemical group 0.000 claims description 115
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 55
• 125000001153 fluoro group Chemical group F* 0.000 claims description 55
• 125000003118 aryl group Chemical group 0.000 claims description 54
• 229920006395 saturated elastomer Polymers 0.000 claims description 48
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 42
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 36
• 238000002360 preparation method Methods 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 108091000080 Phosphotransferase Proteins 0.000 claims description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
• 102000020233 phosphotransferase Human genes 0.000 claims description 27
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 26
• 125000005843 halogen group Chemical group 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 25
• 125000001246 bromo group Chemical group Br* 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 21
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 20
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
• 125000005493 quinolyl group Chemical group 0.000 claims description 19
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 18
• 125000004429 atom Chemical group 0.000 claims description 18
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 17
• 125000002619 bicyclic group Chemical group 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 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 description 16
• 230000000694 effects Effects 0.000 claims description 16
• 125000002950 monocyclic group Chemical group 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 13
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 13
• 125000001188 haloalkyl group Chemical group 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 11
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 11
• 125000004043 oxo group Chemical group O=* 0.000 claims description 11
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 9
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 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 description 8
• 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 description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 8
• 125000004306 triazinyl group Chemical group 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 7
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 7
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 7
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
• 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 description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 5
• 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 description 5
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 5
• 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 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 description 4
• 241001465754 Metazoa Species 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
• 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 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
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 3
• 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 description 3
• 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 description 3
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 2
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 2
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 2
• 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
• 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
• 125000004765 (C1-C4) haloalkyl group Chemical group 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
• YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 3
• 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
• 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
• 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
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• 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
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