CA2457838A1 - 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents - Google Patents
2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents Download PDFInfo
- Publication number
- CA2457838A1 CA2457838A1 CA002457838A CA2457838A CA2457838A1 CA 2457838 A1 CA2457838 A1 CA 2457838A1 CA 002457838 A CA002457838 A CA 002457838A CA 2457838 A CA2457838 A CA 2457838A CA 2457838 A1 CA2457838 A1 CA 2457838A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- methoxy
- alkyl
- 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.)
- Abandoned
Links
- -1 2,4-disubstituted pyrimidinyl Chemical class 0.000 title claims description 1269
- 239000002246 antineoplastic agent Substances 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 257
- 238000000034 method Methods 0.000 claims abstract description 92
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 201000011510 cancer Diseases 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 179
- 125000001424 substituent group Chemical group 0.000 claims description 176
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 163
- 125000000623 heterocyclic group Chemical group 0.000 claims description 116
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 55
- 125000001153 fluoro group Chemical group F* 0.000 claims description 55
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000001246 bromo group Chemical group Br* 0.000 claims description 26
- 108091000080 Phosphotransferase Proteins 0.000 claims description 25
- 102000020233 phosphotransferase Human genes 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 20
- 125000005493 quinolyl group Chemical group 0.000 claims description 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 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 17
- 125000002619 bicyclic group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 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
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
- 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 claims description 10
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 10
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 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 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 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
- 241000124008 Mammalia Species 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
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000004306 triazinyl group Chemical group 0.000 claims description 8
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 7
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 7
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 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 6
- 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
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 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
- 125000006620 amino-(C1-C6) alkyl 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
- 125000000753 cycloalkyl group Chemical group 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
- 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 241001465754 Metazoa Species 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
- 239000003937 drug carrier Substances 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
- 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
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 3
- DTHNDCLPGVAAHV-UHFFFAOYSA-N 2-methoxy-4-[[4-(quinolin-3-ylamino)pyrimidin-2-yl]amino]benzamide Chemical compound C1=C(C(N)=O)C(OC)=CC(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)=C1 DTHNDCLPGVAAHV-UHFFFAOYSA-N 0.000 claims description 3
- WJCHDGFPLWWCSO-UHFFFAOYSA-N 2-n-(4-bromophenyl)-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1=CC(Br)=CC=C1NC1=NC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 WJCHDGFPLWWCSO-UHFFFAOYSA-N 0.000 claims description 3
- NELFTZHPBJKPCE-UHFFFAOYSA-N 2-n-[3-(1,3-oxazol-5-yl)phenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C=1N=C2C=CC=CC2=CC=1NC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CN=CO1 NELFTZHPBJKPCE-UHFFFAOYSA-N 0.000 claims description 3
- MYVSNBQIQCKCNF-UHFFFAOYSA-N 2-n-[3-(1,3-oxazol-5-yl)phenyl]-4-n-quinolin-6-ylpyrimidine-2,4-diamine Chemical compound C=1C=C2N=CC=CC2=CC=1NC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CN=CO1 MYVSNBQIQCKCNF-UHFFFAOYSA-N 0.000 claims description 3
- JPCBYJDUJWNKKF-UHFFFAOYSA-N 2-n-[3-[2-(dimethylamino)ethyl]-4-methoxyphenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1=C(CCN(C)C)C(OC)=CC=C1NC1=NC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 JPCBYJDUJWNKKF-UHFFFAOYSA-N 0.000 claims description 3
- POEZKFMAQCYNKJ-UHFFFAOYSA-N 2-n-[3-methoxy-4-(3-pyrrolidin-1-ylpropyl)phenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound COC1=CC(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)=CC=C1CCCN1CCCC1 POEZKFMAQCYNKJ-UHFFFAOYSA-N 0.000 claims description 3
- HVBSOXZAYMWLEN-UHFFFAOYSA-N 2-n-[4-(4-methylpiperazin-1-yl)phenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 HVBSOXZAYMWLEN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 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
- 150000004985 diamines Chemical class 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
- 230000002401 inhibitory effect Effects 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
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 2
- CBZUEGHFJJAXMK-UHFFFAOYSA-N 2-n-(3,4-diethoxyphenyl)-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1=C(OCC)C(OCC)=CC=C1NC1=NC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 CBZUEGHFJJAXMK-UHFFFAOYSA-N 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
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 16
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 12
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- ZQUSYVORYNBGLG-FQEVSTJZSA-N (2s)-2-[[1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)pyrazole-3-carbonyl]amino]-4-methylpentanoic acid Chemical compound COC1=CC=CC(OC)=C1C1=CC(C(=O)N[C@@H](CC(C)C)C(O)=O)=NN1C1=CC=NC2=CC(Cl)=CC=C12 ZQUSYVORYNBGLG-FQEVSTJZSA-N 0.000 claims 3
- YZCPKKLHWNHXIR-UHFFFAOYSA-N 2-n-(4,5-dimethoxy-2-methylphenyl)-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1NC1=NC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 YZCPKKLHWNHXIR-UHFFFAOYSA-N 0.000 claims 3
- QZNAGOWOUWHEEI-UHFFFAOYSA-N 4-n-quinolin-6-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=NC4=CC=3)C=CN=2)=C1 QZNAGOWOUWHEEI-UHFFFAOYSA-N 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 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
- ITAAIYWZNRTZJU-UHFFFAOYSA-N 2-n-(4,5-dimethoxy-2-methylphenyl)-4-n-(6-methoxyquinolin-3-yl)pyrimidine-2,4-diamine Chemical compound C=1C2=CC(OC)=CC=C2N=CC=1NC(N=1)=CC=NC=1NC1=CC(OC)=C(OC)C=C1C ITAAIYWZNRTZJU-UHFFFAOYSA-N 0.000 claims 2
- DVSPTTRZUWIYRH-UHFFFAOYSA-N 2-n-(4,5-dimethoxy-2-methylphenyl)-4-n-[6-(trifluoromethoxy)quinolin-3-yl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1NC1=NC=CC(NC=2C=C3C=C(OC(F)(F)F)C=CC3=NC=2)=N1 DVSPTTRZUWIYRH-UHFFFAOYSA-N 0.000 claims 2
- FWJJHMAXFWUOSQ-UHFFFAOYSA-N 2-n-(4,5-dimethoxy-2-methylphenyl)-4-n-isoquinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1NC1=NC=CC(NC=2N=CC3=CC=CC=C3C=2)=N1 FWJJHMAXFWUOSQ-UHFFFAOYSA-N 0.000 claims 2
- IQUCVLWUEBFYRJ-UHFFFAOYSA-N 2-n-(4-bromo-2-fluorophenyl)-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound FC1=CC(Br)=CC=C1NC1=NC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 IQUCVLWUEBFYRJ-UHFFFAOYSA-N 0.000 claims 2
- NHJCFSFSQWUBQB-UHFFFAOYSA-N 2-n-(6-morpholin-4-ylpyridin-3-yl)-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1COCCN1C(N=C1)=CC=C1NC1=NC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 NHJCFSFSQWUBQB-UHFFFAOYSA-N 0.000 claims 2
- ZDAGLOXKHXHVNA-UHFFFAOYSA-N 2-n-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound COC1=CC(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)=CC=C1C1=CN=CO1 ZDAGLOXKHXHVNA-UHFFFAOYSA-N 0.000 claims 2
- CNBNCMZGQXJKEQ-UHFFFAOYSA-N 2-n-[3-methoxy-4-[2-[1-[4-(quinolin-3-ylamino)pyrimidin-2-yl]piperidin-4-yl]ethoxy]phenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CN=C(N=3)N3CCC(CC3)CCOC3=CC=C(NC=4N=C(NC=5C=C6C=CC=CC6=NC=5)C=CN=4)C=C3OC)=CN=C21 CNBNCMZGQXJKEQ-UHFFFAOYSA-N 0.000 claims 2
- OIDDQVOZLIYYNQ-UHFFFAOYSA-N 2-n-[4-(2-piperidin-1-ylethoxy)phenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C=1C=C(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)C=CC=1OCCN1CCCCC1 OIDDQVOZLIYYNQ-UHFFFAOYSA-N 0.000 claims 2
- FXDWNCFVVOSWKM-UHFFFAOYSA-N 2-n-[4-(3-piperidin-1-ylpropoxy)phenyl]-4-n-quinolin-3-ylpyrimidine-2,4-diamine Chemical compound C=1C=C(NC=2N=C(NC=3C=C4C=CC=CC4=NC=3)C=CN=2)C=CC=1OCCCN1CCCCC1 FXDWNCFVVOSWKM-UHFFFAOYSA-N 0.000 claims 2
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- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31433901P | 2001-08-22 | 2001-08-22 | |
| US60/314,339 | 2001-08-22 | ||
| US10/225,783 | 2002-08-21 | ||
| US10/225,783 US6939874B2 (en) | 2001-08-22 | 2002-08-21 | Substituted pyrimidinyl derivatives and methods of use |
| PCT/US2002/026870 WO2003018021A1 (en) | 2001-08-22 | 2002-08-22 | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2457838A1 true CA2457838A1 (en) | 2003-03-06 |
Family
ID=26919901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002457838A Abandoned CA2457838A1 (en) | 2001-08-22 | 2002-08-22 | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6939874B2 (https=) |
| EP (1) | EP1427421A1 (https=) |
| JP (1) | JP2005505535A (https=) |
| AU (1) | AU2002336390B2 (https=) |
| CA (1) | CA2457838A1 (https=) |
| MX (1) | MXPA04001623A (https=) |
| PL (1) | PL370041A1 (https=) |
| WO (1) | WO2003018021A1 (https=) |
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| GB0321710D0 (en) * | 2003-09-16 | 2003-10-15 | Novartis Ag | Organic compounds |
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| US7303591B2 (en) | 2004-02-27 | 2007-12-04 | L'oreal S.A. | Composition comprising at least one mixed dye comprising at least two chromophores of (hetero) aromatic nitro or cyclic azine type, dyeing process, and mixed dyes |
| US7300471B2 (en) | 2004-02-27 | 2007-11-27 | L'oreal S.A. | Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero) arylmethane type, dyeing process and mixed dyes. |
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| PL370041A1 (en) | 2005-05-16 |
| MXPA04001623A (es) | 2004-07-08 |
| US6939874B2 (en) | 2005-09-06 |
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| US20040063705A1 (en) | 2004-04-01 |
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