RU2003131693A - Новые ингибиторы тирозин киназ - Google Patents
Новые ингибиторы тирозин киназ Download PDFInfo
- Publication number
- RU2003131693A RU2003131693A RU2003131693/04A RU2003131693A RU2003131693A RU 2003131693 A RU2003131693 A RU 2003131693A RU 2003131693/04 A RU2003131693/04 A RU 2003131693/04A RU 2003131693 A RU2003131693 A RU 2003131693A RU 2003131693 A RU2003131693 A RU 2003131693A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- pyridin
- benzimidazol
- hydroxyethylamino
- alkyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title 1
- -1 sulfoxy, sulfonyl Chemical group 0.000 claims 83
- 229910052739 hydrogen Inorganic materials 0.000 claims 80
- 239000001257 hydrogen Substances 0.000 claims 70
- 150000001875 compounds Chemical class 0.000 claims 50
- 150000002431 hydrogen Chemical class 0.000 claims 49
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 17
- 125000003342 alkenyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000005309 thioalkoxy group Chemical group 0.000 claims 15
- 150000003573 thiols Chemical class 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 5
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 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 4
- OTOIUCLFSQHFOX-UHFFFAOYSA-N 3-sulfonylmorpholine Chemical compound O=S(=O)=C1COCCN1 OTOIUCLFSQHFOX-UHFFFAOYSA-N 0.000 claims 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- XPTAUSRPHWOZPN-UHFFFAOYSA-N morpholin-4-yl hydrogen sulfate Chemical compound OS(=O)(=O)ON1CCOCC1 XPTAUSRPHWOZPN-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 2
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin 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(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
- HZQLLKQPXMHIMZ-UHFFFAOYSA-N N-[1-[2-[4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazol-5-yl]piperidin-4-yl]-2-fluoroacetamide Chemical compound N=1C=2C(C)=CC(N3CCC(CC3)NC(=O)CF)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 HZQLLKQPXMHIMZ-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- WDELNBOQCPAGPI-KRWDZBQOSA-N (2s)-2-[[6-chloro-5-(6-imidazol-1-yl-4-methyl-1h-benzimidazol-2-yl)pyrimidin-4-yl]amino]-3-phenylpropan-1-ol Chemical compound C([C@@H](CO)NC1=NC=NC(Cl)=C1C=1NC=2C=C(C=C(C=2N=1)C)N1C=NC=C1)C1=CC=CC=C1 WDELNBOQCPAGPI-KRWDZBQOSA-N 0.000 claims 1
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- LWELCYJSAYQTOX-UHFFFAOYSA-N 1-[2-[4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazol-5-yl]-N-(2-fluoroethoxy)piperidine-4-carboxamide Chemical compound N=1C=2C(C)=CC(N3CCC(CC3)C(=O)NOCCF)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 LWELCYJSAYQTOX-UHFFFAOYSA-N 0.000 claims 1
- WKJBSMLANQKUCC-UHFFFAOYSA-N 1-[2-[4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazol-5-yl]-N-methoxypiperidine-4-carboxamide Chemical compound C1CC(C(=O)NOC)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NCC(O)C=3C=C(Cl)C=CC=3)=O)C2=C1 WKJBSMLANQKUCC-UHFFFAOYSA-N 0.000 claims 1
- IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 claims 1
- BKRADANXACAJKT-UHFFFAOYSA-N 2-[4-[2-[4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazol-5-yl]piperazin-1-yl]acetonitrile Chemical compound N=1C=2C(C)=CC(N3CCN(CC#N)CC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 BKRADANXACAJKT-UHFFFAOYSA-N 0.000 claims 1
- NQRCKUVJMDFGCB-KRWDZBQOSA-N 2-[4-[[(2S)-1-(3-chlorophenyl)-3-hydroxypropan-2-yl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)C#N)C1=CC=CC(Cl)=C1 NQRCKUVJMDFGCB-KRWDZBQOSA-N 0.000 claims 1
- HHGVGFMWJQKOFG-KRWDZBQOSA-N 2-[4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)C#N)C1=CC=CC=C1 HHGVGFMWJQKOFG-KRWDZBQOSA-N 0.000 claims 1
- BXPWYRZCEDJCQW-GOSISDBHSA-N 2-[4-[[(2S)-2-hydroxy-2-phenylethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)C#N)=CC=CC=C1 BXPWYRZCEDJCQW-GOSISDBHSA-N 0.000 claims 1
- LQEBRSGCLFNPHN-UHFFFAOYSA-N 2-[4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)C#N)C(=O)NC=C1 LQEBRSGCLFNPHN-UHFFFAOYSA-N 0.000 claims 1
- YETIHONGYJNLSF-UHFFFAOYSA-N 2-[4-[[2-(3-bromophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile Chemical compound N=1C=2C(C)=CC(C#N)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Br)=C1 YETIHONGYJNLSF-UHFFFAOYSA-N 0.000 claims 1
- QEDRKDBUNJAFMZ-UHFFFAOYSA-N 2-[4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile Chemical compound N=1C=2C(C)=CC(C#N)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 QEDRKDBUNJAFMZ-UHFFFAOYSA-N 0.000 claims 1
- BKOVQGMNMPRQPP-UHFFFAOYSA-N 2-[4-[[2-(3-fluorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile Chemical compound N=1C=2C(C)=CC(C#N)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(F)=C1 BKOVQGMNMPRQPP-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims 1
- COZVWKMJBNLADG-HNNXBMFYSA-N 3-(1H-benzimidazol-2-yl)-4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(=O)NC=C1)C=1NC2=CC=CC=C2N=1)C1=CC=CC=C1 COZVWKMJBNLADG-HNNXBMFYSA-N 0.000 claims 1
- XVTGMPIWLFRYCU-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC=CC=C3N=2)C(=O)NC=C1 XVTGMPIWLFRYCU-UHFFFAOYSA-N 0.000 claims 1
- CMYZQDNEXKMVAP-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-4-[[2-(3-bromophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C1=CNC(=O)C(C=2NC3=CC=CC=C3N=2)=C1NCC(O)C1=CC=CC(Br)=C1 CMYZQDNEXKMVAP-UHFFFAOYSA-N 0.000 claims 1
- VVIPLSCLYCWUQT-UHFFFAOYSA-N 3-[4-[2-[4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazol-5-yl]piperazin-1-yl]propanenitrile Chemical compound N=1C=2C(C)=CC(N3CCN(CCC#N)CC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 VVIPLSCLYCWUQT-UHFFFAOYSA-N 0.000 claims 1
- OBHSRNCZUIOTPY-OAQYLSRUSA-N 3-[4-bromo-6-(morpholin-4-ylmethyl)-1H-benzimidazol-2-yl]-4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C([C@@H](O)C=1C=C(Cl)C=CC=1)NC=1C=CNC(=O)C=1C(NC1=C2)=NC1=C(Br)C=C2CN1CCOCC1 OBHSRNCZUIOTPY-OAQYLSRUSA-N 0.000 claims 1
- TUZKEXPUYPJNDF-UHFFFAOYSA-N 3-[6-(4-acetylpiperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-[[2-(3-bromophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C1CN(C(=O)C)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NCC(O)C=3C=C(Br)C=CC=3)=O)C2=C1 TUZKEXPUYPJNDF-UHFFFAOYSA-N 0.000 claims 1
- QIEKBURWQYYQLT-UHFFFAOYSA-N 3-[6-(4-acetylpiperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C1CN(C(=O)C)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NCC(O)C=3C=C(Cl)C=CC=3)=O)C2=C1 QIEKBURWQYYQLT-UHFFFAOYSA-N 0.000 claims 1
- MUZVVLKDYCWGDU-VWLOTQADSA-N 3-[6-(4-benzoylpiperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)N1CCN(CC1)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 MUZVVLKDYCWGDU-VWLOTQADSA-N 0.000 claims 1
- DVSOQVVEQNAVNQ-QHCPKHFHSA-N 3-[6-(4-butylpiperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1H-pyridin-2-one Chemical compound C1CN(CCCC)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3N[C@H](CO)CC=3C=CC=CC=3)=O)C2=C1 DVSOQVVEQNAVNQ-QHCPKHFHSA-N 0.000 claims 1
- QLARNLBZNLHNOT-UHFFFAOYSA-N 3-[6-(aminomethyl)-4-methyl-1H-benzimidazol-2-yl]-4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(CN)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 QLARNLBZNLHNOT-UHFFFAOYSA-N 0.000 claims 1
- HGDHHEZBLVABGA-UHFFFAOYSA-N 3-[6-[4-(2-chloroacetyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CC3)C(=O)CCl)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 HGDHHEZBLVABGA-UHFFFAOYSA-N 0.000 claims 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 1
- CLWRLQRRLJJWJG-JOCHJYFZSA-N 4-[2-[4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazol-5-yl]piperazine-1-carbaldehyde Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(CC2)C=O)C(=O)NC=C1 CLWRLQRRLJJWJG-JOCHJYFZSA-N 0.000 claims 1
- UOEYQBMDBOFQKW-JOCHJYFZSA-N 4-[2-[4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-2-oxo-1H-pyridin-3-yl]-7-methyl-3H-benzimidazol-5-yl]piperazine-1-carbaldehyde Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2CCN(CC2)C=O)=CC=CC(Cl)=C1 UOEYQBMDBOFQKW-JOCHJYFZSA-N 0.000 claims 1
- QCDSKOUKWJFTKU-OFNKIYASSA-N 4-[[(1S,2R)-1-hydroxy-2,3-dihydro-1H-inden-2-yl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound Cc1cc(cc2[nH]c(nc12)-c1c(N[C@@H]2Cc3ccccc3[C@@H]2O)cc[nH]c1=O)-n1ccnc1 QCDSKOUKWJFTKU-OFNKIYASSA-N 0.000 claims 1
- LQRBWXDBMNHGCK-FQEVSTJZSA-N 4-[[(2R)-2-hydroxy-2-phenylethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1([C@@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NC=C2)=CC=CC=C1 LQRBWXDBMNHGCK-FQEVSTJZSA-N 0.000 claims 1
- VULKTEGKCCHBBY-IBGZPJMESA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-(4-methyl-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)N1CCOCC1)C1=CC=CC=C1 VULKTEGKCCHBBY-IBGZPJMESA-N 0.000 claims 1
- SLYJOQJAIBXMFF-FQEVSTJZSA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-(4-methyl-6-piperidin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)N1CCCCC1)C1=CC=CC=C1 SLYJOQJAIBXMFF-FQEVSTJZSA-N 0.000 claims 1
- XBNXAXRVKFHSSL-QFIPXVFZSA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-[4-methyl-6-(2-morpholin-4-ylethylamino)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3N[C@H](CO)CC=3C=CC=CC=3)=O)=NC=2C(C)=CC=1NCCN1CCOCC1 XBNXAXRVKFHSSL-QFIPXVFZSA-N 0.000 claims 1
- QQUOABRZUGYNQT-HSZRJFAPSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-(2-morpholin-4-ylethoxy)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(OCCN4CCOCC4)=CC(C)=C3N=2)C(=O)NC=C1 QQUOABRZUGYNQT-HSZRJFAPSA-N 0.000 claims 1
- DNTQJDXWGFMNLI-OPAMFIHVSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2R)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@@H](C)OCC2)C(=O)NC=C1 DNTQJDXWGFMNLI-OPAMFIHVSA-N 0.000 claims 1
- XTGIVFQBEPPGGX-PGRDOPGGSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CF)OCC2)C(=O)NC=C1 XTGIVFQBEPPGGX-PGRDOPGGSA-N 0.000 claims 1
- LUSNIDFBBMXWAZ-XMSQKQJNSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CO)OCC2)C(=O)NC=C1 LUSNIDFBBMXWAZ-XMSQKQJNSA-N 0.000 claims 1
- ODUJFBNSLMAOSE-AUSIDOKSSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Br)C(OC)=CC=3)=O)C2=C1 ODUJFBNSLMAOSE-AUSIDOKSSA-N 0.000 claims 1
- XTGIVFQBEPPGGX-XMSQKQJNSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@@H](CF)OCC2)C(=O)NC=C1 XTGIVFQBEPPGGX-XMSQKQJNSA-N 0.000 claims 1
- LUSNIDFBBMXWAZ-PGRDOPGGSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound COc1ccc(cc1Br)[C@H](O)CNc1cc[nH]c(=O)c1-c1nc2c(C)cc(cc2[nH]1)N1CCO[C@H](CO)C1 LUSNIDFBBMXWAZ-PGRDOPGGSA-N 0.000 claims 1
- JIADGRLHJMOUEK-HSZRJFAPSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(CCO)CC2)C(=O)NC=C1 JIADGRLHJMOUEK-HSZRJFAPSA-N 0.000 claims 1
- ONIBKFKEUOBONC-KSFYIVLOSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2S)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](C)OCC2)C(=O)NC=C1 ONIBKFKEUOBONC-KSFYIVLOSA-N 0.000 claims 1
- PUHIHKJDRCRYTD-OAQYLSRUSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-(5,6-dihydro-4H-pyrimidin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C=NCCC2)C(=O)NC=C1 PUHIHKJDRCRYTD-OAQYLSRUSA-N 0.000 claims 1
- XNQQOBWDWJLPKE-PGRDOPGGSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CF)OCC2)C(=O)NC=C1 XNQQOBWDWJLPKE-PGRDOPGGSA-N 0.000 claims 1
- RJOLTVNZKRBSOZ-XMSQKQJNSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CO)OCC2)C(=O)NC=C1 RJOLTVNZKRBSOZ-XMSQKQJNSA-N 0.000 claims 1
- PKNHVWJAADMUFX-AUSIDOKSSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C(OC)=CC=3)=O)C2=C1 PKNHVWJAADMUFX-AUSIDOKSSA-N 0.000 claims 1
- XNQQOBWDWJLPKE-XMSQKQJNSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@@H](CF)OCC2)C(=O)NC=C1 XNQQOBWDWJLPKE-XMSQKQJNSA-N 0.000 claims 1
- RJOLTVNZKRBSOZ-PGRDOPGGSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound COc1ccc(cc1Cl)[C@H](O)CNc1cc[nH]c(=O)c1-c1nc2c(C)cc(cc2[nH]1)N1CCO[C@H](CO)C1 RJOLTVNZKRBSOZ-PGRDOPGGSA-N 0.000 claims 1
- PKNHVWJAADMUFX-WMZHIEFXSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C(OC)=CC=3)=O)C2=C1 PKNHVWJAADMUFX-WMZHIEFXSA-N 0.000 claims 1
- GAUMNPIAVGVDBX-HSZRJFAPSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-(2-morpholin-4-ylethoxy)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)=NC=2C(C)=CC=1OCCN1CCOCC1 GAUMNPIAVGVDBX-HSZRJFAPSA-N 0.000 claims 1
- IIJGLRWTELJRPH-OPAMFIHVSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2R)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@H](C)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)C2=C1 IIJGLRWTELJRPH-OPAMFIHVSA-N 0.000 claims 1
- IIJGLRWTELJRPH-KSFYIVLOSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2S)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@@H](C)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)C2=C1 IIJGLRWTELJRPH-KSFYIVLOSA-N 0.000 claims 1
- DACIYZDSXDZZSX-HSZRJFAPSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(4-methylpiperazin-1-yl)methyl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CN(C)CCN1CC1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)C2=C1 DACIYZDSXDZZSX-HSZRJFAPSA-N 0.000 claims 1
- WHJWUUJEQQJCLJ-SIKLNZKXSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C[C@H](CF)OCC2)=CC=CC(Cl)=C1 WHJWUUJEQQJCLJ-SIKLNZKXSA-N 0.000 claims 1
- HHGSXZXKYKUWGJ-DENIHFKCSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C[C@H](CO)OCC2)=CC=CC(Cl)=C1 HHGSXZXKYKUWGJ-DENIHFKCSA-N 0.000 claims 1
- UHOVHYKNOIFMRB-NFBKMPQASA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)C2=C1 UHOVHYKNOIFMRB-NFBKMPQASA-N 0.000 claims 1
- WHJWUUJEQQJCLJ-DENIHFKCSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C[C@@H](CF)OCC2)=CC=CC(Cl)=C1 WHJWUUJEQQJCLJ-DENIHFKCSA-N 0.000 claims 1
- UHOVHYKNOIFMRB-NZQKXSOJSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound COC[C@@H]1CN(CCO1)c1cc(C)c2nc([nH]c2c1)-c1c(NC[C@@H](O)c2cccc(Cl)c2)cc[nH]c1=O UHOVHYKNOIFMRB-NZQKXSOJSA-N 0.000 claims 1
- AATRIKZDGKCSFA-GAJHUEQPSA-N 4-[[(2S)-2-(7-bromo-2,3-dihydro-1-benzofuran-4-yl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3NC[C@@H](O)C=3C=4CCOC=4C(Br)=CC=3)=O)=NC=2C(C)=CC=1N1CCO[C@@H](CF)C1 AATRIKZDGKCSFA-GAJHUEQPSA-N 0.000 claims 1
- AATRIKZDGKCSFA-UZUQRXQVSA-N 4-[[(2S)-2-(7-bromo-2,3-dihydro-1-benzofuran-4-yl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3NC[C@@H](O)C=3C=4CCOC=4C(Br)=CC=3)=O)=NC=2C(C)=CC=1N1CCO[C@H](CF)C1 AATRIKZDGKCSFA-UZUQRXQVSA-N 0.000 claims 1
- LQRBWXDBMNHGCK-HXUWFJFHSA-N 4-[[(2S)-2-hydroxy-2-phenylethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NC=C2)=CC=CC=C1 LQRBWXDBMNHGCK-HXUWFJFHSA-N 0.000 claims 1
- GCHQRFUKBLZIMY-IBGZPJMESA-N 4-[[(2S)-2-hydroxy-2-pyridin-2-ylethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1([C@@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NC=C2)=CC=CC=N1 GCHQRFUKBLZIMY-IBGZPJMESA-N 0.000 claims 1
- FSDYMRXZPHZFJS-UHFFFAOYSA-N 4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCOCC2)C(=O)NC=C1 FSDYMRXZPHZFJS-UHFFFAOYSA-N 0.000 claims 1
- MDBNOVPXWFLVKY-UHFFFAOYSA-N 4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C=NC=C2)C(=O)NC=C1 MDBNOVPXWFLVKY-UHFFFAOYSA-N 0.000 claims 1
- PZSACZRLMBGKSF-VEXWJQHLSA-N 4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2S)-2-morpholin-4-ylpropoxy]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound BrC=1C=C(C=CC1OC)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)OC[C@H](C)N2CCOCC2)O PZSACZRLMBGKSF-VEXWJQHLSA-N 0.000 claims 1
- IMMXVSIPHLGTTG-UHFFFAOYSA-N 4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[4-(3-fluoropropyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(CCCF)CC2)C(=O)NC=C1 IMMXVSIPHLGTTG-UHFFFAOYSA-N 0.000 claims 1
- FKXIIIPVPAGWFJ-UHFFFAOYSA-N 4-[[2-(3-bromophenyl)-2-hydroxyethyl]amino]-3-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CCO)CC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Br)=C1 FKXIIIPVPAGWFJ-UHFFFAOYSA-N 0.000 claims 1
- LGLHDKFGXZEGKW-UHFFFAOYSA-N 4-[[2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl]amino]-3-[6-[4-(3-fluoropropyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CCCF)CC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=C(F)C(Cl)=C1 LGLHDKFGXZEGKW-UHFFFAOYSA-N 0.000 claims 1
- VTMIHYCOXBGSOX-UHFFFAOYSA-N 4-[[2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[4-(3-fluoropropyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(CCCF)CC2)C(=O)NC=C1 VTMIHYCOXBGSOX-UHFFFAOYSA-N 0.000 claims 1
- UYYCMYGVPNHLTH-UHFFFAOYSA-N 4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-(4-propan-2-ylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CN(C(C)C)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NCC(O)C=3C=C(Cl)C=CC=3)=O)C2=C1 UYYCMYGVPNHLTH-UHFFFAOYSA-N 0.000 claims 1
- ZEBVMFXVTKXQJX-VEXWJQHLSA-N 4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2S)-2-morpholin-4-ylpropoxy]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)OC[C@H](C)N2CCOCC2)O ZEBVMFXVTKXQJX-VEXWJQHLSA-N 0.000 claims 1
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- OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229960003881 letrozole Drugs 0.000 claims 1
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- 229960004296 megestrol acetate Drugs 0.000 claims 1
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 claims 1
- 229960001924 melphalan Drugs 0.000 claims 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 claims 1
- 229960004857 mitomycin Drugs 0.000 claims 1
- 150000002780 morpholines Chemical class 0.000 claims 1
- BLCLNMBMMGCOAS-UHFFFAOYSA-N n-[1-[[1-[[1-[[1-[[1-[[1-[[1-[2-[(carbamoylamino)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amin Chemical compound C1CCC(C(=O)NNC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(COC(C)(C)C)NC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 BLCLNMBMMGCOAS-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
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- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 1
- 229960004622 raloxifene Drugs 0.000 claims 1
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
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- 229960001603 tamoxifen Drugs 0.000 claims 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
- 229940063683 taxotere Drugs 0.000 claims 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 1
- 229960005026 toremifene Drugs 0.000 claims 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 claims 1
- 239000002525 vasculotropin inhibitor Substances 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
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Classifications
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| IL (1) | IL158041A0 (enExample) |
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| NO (1) | NO20034308L (enExample) |
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| PL (1) | PL373300A1 (enExample) |
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Cited By (1)
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| RU2493153C2 (ru) * | 2007-12-21 | 2013-09-20 | Ф.Хоффманн-Ля Рош Аг | Карбоксил- или гидроксилзамещенные производные бензимидазола |
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| US7081454B2 (en) * | 2001-03-28 | 2006-07-25 | Bristol-Myers Squibb Co. | Tyrosine kinase inhibitors |
| AU2003218236B2 (en) | 2002-03-01 | 2007-12-06 | Bristol-Myers Squibb Company | Transgenic non-human mammals expressing constitutively activated tyrosine kinase receptors |
| WO2003106452A2 (en) * | 2002-06-12 | 2003-12-24 | Millennium Pharmaceuticals, Inc. | Antagonists of melanin concentrating hormone receptor |
| EP1575580A4 (en) * | 2002-12-02 | 2009-06-10 | Arqule Inc | METHOD FOR TREATING CARCINOMA |
| WO2004063151A2 (en) | 2003-01-03 | 2004-07-29 | Bristol-Myers Squibb Company | Novel tyrosine kinase inhibitors |
| WO2004069160A2 (en) * | 2003-01-28 | 2004-08-19 | Smithkline Beecham Corporation | Chemical compounds |
| US7312215B2 (en) | 2003-07-29 | 2007-12-25 | Bristol-Myers Squibb Company | Benzimidazole C-2 heterocycles as kinase inhibitors |
| EP1663204B1 (en) * | 2003-08-29 | 2014-05-07 | Exelixis, Inc. | C-kit modulators and methods of use |
| US20050075358A1 (en) * | 2003-10-06 | 2005-04-07 | Carboni Joan M. | Methods for treating IGF1R-inhibitor induced hyperglycemia |
| JP2007514759A (ja) | 2003-12-19 | 2007-06-07 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| DE102004010207A1 (de) | 2004-03-02 | 2005-09-15 | Aventis Pharma S.A. | Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate |
| CN1960993A (zh) | 2004-04-02 | 2007-05-09 | Osi制药公司 | 6,6－双环取代的杂双环蛋白激酶抑制剂 |
| WO2006023931A2 (en) | 2004-08-18 | 2006-03-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| WO2006065946A1 (en) * | 2004-12-16 | 2006-06-22 | Vertex Pharmaceuticals Incorporated | Pyrid-2-ones useful as inhibitors of tec family protein kinases for the treatment of inflammatory, proliferative and immunologically-mediated diseases |
| US7538113B2 (en) | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7534796B2 (en) | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7582634B2 (en) | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
| US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
| WO2006130657A2 (en) | 2005-05-31 | 2006-12-07 | Bristol-Myers Squibb Company | Stereoselective reduction process for the preparation of pyrrolotriazine compounds |
| US7855289B2 (en) | 2005-08-04 | 2010-12-21 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| US8093401B2 (en) | 2005-08-04 | 2012-01-10 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| ES2397275T3 (es) | 2005-08-04 | 2013-03-05 | Sirtris Pharmaceuticals, Inc. | Derivados de imidazopiridina como agentes moduladores de la sirtuína |
| US8088928B2 (en) | 2005-08-04 | 2012-01-03 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| ES2361338T3 (es) | 2005-08-29 | 2011-06-16 | Vertex Pharmaceuticals Incorporated | Pirid-2-onas 3,5-disustituidas útiles como inhibidores de la familia tec de tirosina quinasas no ligadas a receptor. |
| WO2007027729A1 (en) | 2005-08-29 | 2007-03-08 | Vertex Pharmaceuticals Incorporated | 3, 5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-receptor tyrosine kinases |
| ATE548363T1 (de) | 2005-08-29 | 2012-03-15 | Vertex Pharma | 3,5-disubstituierte pyrid-2-one, die sich als inhibitoren der tec-familie von nicht-rezeptor- tyrosinkinasen eignen |
| WO2007026720A1 (ja) * | 2005-08-31 | 2007-03-08 | Taisho Pharmaceutical Co., Ltd. | 縮環ピラゾール誘導体 |
| US8575164B2 (en) | 2005-12-19 | 2013-11-05 | OSI Pharmaceuticals, LLC | Combination cancer therapy |
| WO2007145203A1 (ja) * | 2006-06-13 | 2007-12-21 | Daiichi Fine Chemical Co., Ltd. | 光学活性２－アミノ－１－（４－フルオロフェニル）エタノール |
| US8063225B2 (en) | 2006-08-14 | 2011-11-22 | Chembridge Corporation | Tricyclic compound derivatives useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders |
| WO2008022747A1 (en) * | 2006-08-21 | 2008-02-28 | F. Hoffmann-La Roche Ag | Tricyclic lactam derivatives, their manufacture and use as pharmaceutical agents |
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| US6162804A (en) * | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| BR0012450B1 (pt) * | 1999-06-23 | 2011-08-23 | benzimidazóis substituìdos. | |
| US7081454B2 (en) * | 2001-03-28 | 2006-07-25 | Bristol-Myers Squibb Co. | Tyrosine kinase inhibitors |
-
2002
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- 2002-03-26 KR KR10-2003-7012594A patent/KR20030083016A/ko not_active Withdrawn
- 2002-03-26 WO PCT/US2002/009402 patent/WO2002079192A1/en not_active Ceased
- 2002-03-26 MX MXPA03008690A patent/MXPA03008690A/es unknown
- 2002-03-26 PL PL02373300A patent/PL373300A1/xx not_active Application Discontinuation
- 2002-03-26 EP EP02723631A patent/EP1381598A4/en not_active Withdrawn
- 2002-03-26 HU HU0400323A patent/HUP0400323A2/hu unknown
- 2002-03-26 CN CNA028105168A patent/CN1514833A/zh active Pending
- 2002-03-26 YU YU84603A patent/YU84603A/sh unknown
- 2002-03-26 GE GE5363A patent/GEP20053660B/en unknown
- 2002-03-26 EE EEP200300475A patent/EE200300475A/xx unknown
- 2002-03-26 SK SK12002003A patent/SK12002003A3/sk not_active Application Discontinuation
- 2002-03-26 JP JP2002577817A patent/JP2004534010A/ja not_active Withdrawn
- 2002-03-26 CA CA002442428A patent/CA2442428A1/en not_active Abandoned
- 2002-03-26 HR HR20030844A patent/HRP20030844A2/hr not_active Application Discontinuation
- 2002-03-26 CZ CZ20032615A patent/CZ20032615A3/cs unknown
- 2002-03-26 IL IL15804102A patent/IL158041A0/xx unknown
- 2002-03-26 BR BR0208373-6A patent/BR0208373A/pt not_active IP Right Cessation
- 2002-03-27 PE PE2002000244A patent/PE20021015A1/es not_active Application Discontinuation
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- 2002-03-27 AR ARP020101167A patent/AR035804A1/es not_active Application Discontinuation
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- 2003-09-25 ZA ZA200307466A patent/ZA200307466B/en unknown
- 2003-09-26 IS IS6968A patent/IS6968A/is unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2493153C2 (ru) * | 2007-12-21 | 2013-09-20 | Ф.Хоффманн-Ля Рош Аг | Карбоксил- или гидроксилзамещенные производные бензимидазола |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20034308L (no) | 2003-11-26 |
| KR20030083016A (ko) | 2003-10-23 |
| BG108206A (bg) | 2004-11-30 |
| GEP20053660B (en) | 2005-11-10 |
| CN1514833A (zh) | 2004-07-21 |
| BR0208373A (pt) | 2005-02-22 |
| EE200300475A (et) | 2004-02-16 |
| UY27234A1 (es) | 2002-10-31 |
| MXPA03008690A (es) | 2003-12-12 |
| CZ20032615A3 (en) | 2004-03-17 |
| SK12002003A3 (en) | 2004-10-05 |
| EP1381598A1 (en) | 2004-01-21 |
| IL158041A0 (en) | 2004-03-28 |
| JP2004534010A (ja) | 2004-11-11 |
| AR035804A1 (es) | 2004-07-14 |
| PE20021015A1 (es) | 2002-11-10 |
| CA2442428A1 (en) | 2002-10-10 |
| PL373300A1 (en) | 2005-08-22 |
| HUP0400323A2 (hu) | 2005-11-28 |
| EP1381598A4 (en) | 2008-03-19 |
| NO20034308D0 (no) | 2003-09-26 |
| ZA200307466B (en) | 2005-01-13 |
| IS6968A (is) | 2003-09-26 |
| HRP20030844A2 (en) | 2005-08-31 |
| WO2002079192A1 (en) | 2002-10-10 |
| YU84603A (sh) | 2006-03-03 |
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