BG108206A - Нови инхибитори на тирозинкиназа - Google Patents

Нови инхибитори на тирозинкиназа Download PDF

Info

Publication number: BG108206A
Authority: BG; Bulgaria
Prior art keywords: methyl; hydroxy; pyridin; ethylamino; benzimidazol
Prior art date: 2001-03-28

Application number

BG108206A

Other languages

Bulgarian (bg)

English (en)

Inventor

Mark WITTMAN

Neelakantan Balasubramanian

Upender Velaparthi

Kurt Zimmerman

Mark Saulnier

Peiying Liu

Xiaopeng Sang

David Frennesson

Karen Stoffan

James Tarrant

Original Assignee

Bristol-Myers Squibb Company

Priority date (The priority date 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 date listed.)

2001-03-28

Filing date

2003-09-26

Publication date

2004-11-30

2003-09-26 Application filed by Bristol-Myers Squibb Company filed Critical Bristol-Myers Squibb Company

2004-11-30 Publication of BG108206A publication Critical patent/BG108206A/bg

Links

229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 6
239000005483 tyrosine kinase inhibitor Substances 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 199
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 22
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 22
238000011282 treatment Methods 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 14
239000002246 antineoplastic agent Substances 0.000 claims abstract description 11
201000010099 disease Diseases 0.000 claims abstract description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
-1 sulfoxy, sulfonyl Chemical group 0.000 claims description 449
229910052739 hydrogen Inorganic materials 0.000 claims description 140
239000001257 hydrogen Substances 0.000 claims description 119
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 106
125000000217 alkyl group Chemical group 0.000 claims description 91
150000002431 hydrogen Chemical class 0.000 claims description 80
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 76
125000001072 heteroaryl group Chemical group 0.000 claims description 60
239000000203 mixture Substances 0.000 claims description 54
125000003545 alkoxy group Chemical group 0.000 claims description 52
125000003118 aryl group Chemical group 0.000 claims description 52
239000000460 chlorine Substances 0.000 claims description 50
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
125000003342 alkenyl group Chemical group 0.000 claims description 42
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
125000000753 cycloalkyl group Chemical group 0.000 claims description 38
125000005843 halogen group Chemical group 0.000 claims description 37
125000005309 thioalkoxy group Chemical group 0.000 claims description 35
150000003573 thiols Chemical class 0.000 claims description 33
SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 32
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 31
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 22
229910052731 fluorine Inorganic materials 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
206010028980 Neoplasm Diseases 0.000 claims description 19
125000000304 alkynyl group Chemical group 0.000 claims description 19
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 18
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 17
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
201000011510 cancer Diseases 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000003282 alkyl amino group Chemical group 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 12
239000003112 inhibitor Substances 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
125000000547 substituted alkyl group Chemical group 0.000 claims description 11
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 8
239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 8
108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 8
229960001433 erlotinib Drugs 0.000 claims description 8
AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 8
XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 8
229940084651 iressa Drugs 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
229940002612 prodrug Drugs 0.000 claims description 7
239000000651 prodrug Substances 0.000 claims description 7
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 7
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 7
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 description 6
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 description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
150000002780 morpholines Chemical class 0.000 claims description 6
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 5
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 5
102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 4
WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims description 4
OTOIUCLFSQHFOX-UHFFFAOYSA-N 3-sulfonylmorpholine Chemical compound O=S(=O)=C1COCCN1 OTOIUCLFSQHFOX-UHFFFAOYSA-N 0.000 claims description 4
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
229930012538 Paclitaxel Natural products 0.000 claims description 4
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims description 4
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
239000004037 angiogenesis inhibitor Substances 0.000 claims description 4
229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
229930013356 epothilone Natural products 0.000 claims description 4
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide 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](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 4
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125000001188 haloalkyl group Chemical group 0.000 claims description 4
229940022353 herceptin Drugs 0.000 claims description 4
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
150000004677 hydrates Chemical class 0.000 claims description 4
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
229960001592 paclitaxel Drugs 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
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 description 4
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 3
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 3
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 3
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 description 3
102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
229960004679 doxorubicin Drugs 0.000 claims description 3
229960002949 fluorouracil Drugs 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 claims description 3
229960000485 methotrexate Drugs 0.000 claims description 3
229960001603 tamoxifen Drugs 0.000 claims description 3
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 description 3
229960000303 topotecan Drugs 0.000 claims description 3
239000002525 vasculotropin inhibitor Substances 0.000 claims description 3
ZLEMMUBHALJEGB-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-methoxyethoxy)piperidine-4-carboxamide Chemical compound C1CC(C(=O)NOCCOC)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NCC(O)C=3C=C(Cl)C=CC=3)=O)C2=C1 ZLEMMUBHALJEGB-UHFFFAOYSA-N 0.000 claims description 2
IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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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
- C07D401/04—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
- 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
- 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
- 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)

BG108206A 2001-03-28 2003-09-26 Нови инхибитори на тирозинкиназа BG108206A (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US27932701P	2001-03-28	2001-03-28

Publications (1)

Publication Number	Publication Date
BG108206A true BG108206A (bg)	2004-11-30

Family

ID=23068491

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG108206A BG108206A (bg)	2001-03-28	2003-09-26	Нови инхибитори на тирозинкиназа

Country Status (25)

Country	Link
EP (1)	EP1381598A4 (pl)
JP (1)	JP2004534010A (pl)
KR (1)	KR20030083016A (pl)
CN (1)	CN1514833A (pl)
AR (1)	AR035804A1 (pl)
BG (1)	BG108206A (pl)
BR (1)	BR0208373A (pl)
CA (1)	CA2442428A1 (pl)
CZ (1)	CZ20032615A3 (pl)
EE (1)	EE200300475A (pl)
GE (1)	GEP20053660B (pl)
HR (1)	HRP20030844A2 (pl)
HU (1)	HUP0400323A2 (pl)
IL (1)	IL158041A0 (pl)
IS (1)	IS6968A (pl)
MX (1)	MXPA03008690A (pl)
NO (1)	NO20034308L (pl)
PE (1)	PE20021015A1 (pl)
PL (1)	PL373300A1 (pl)
RU (1)	RU2003131693A (pl)
SK (1)	SK12002003A3 (pl)
UY (1)	UY27234A1 (pl)
WO (1)	WO2002079192A1 (pl)
YU (1)	YU84603A (pl)
ZA (1)	ZA200307466B (pl)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7081454B2 (en) *	2001-03-28	2006-07-25	Bristol-Myers Squibb Co.	Tyrosine kinase inhibitors
IL163515A0 (en)	2002-03-01	2005-12-18	Bristol Myers Squibb Co	Transgenic non-human mammals
CA2488635C (en) *	2002-06-12	2012-10-23	Abbott Laboratories	Antagonists of melanin concentrating hormone receptor
EP1575580A4 (en) *	2002-12-02	2009-06-10	Arqule Inc	METHOD FOR TREATING CARCINOMA
US7189716B2 (en)	2003-01-03	2007-03-13	Bristol-Myers Squibb Company	Tyrosine kinase inhibitors
US7329678B2 (en) *	2003-01-28	2008-02-12	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
WO2005061519A1 (en)	2003-12-19	2005-07-07	Takeda San Diego, Inc.	Kinase inhibitors
DE102004010207A1 (de) *	2004-03-02	2005-09-15	Aventis Pharma S.A.	Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate
TWI378934B (en)	2004-04-02	2012-12-11	Osi Pharm Inc	6,6-bicyclic ring substituted heterobicyclic protein kinase inhibitors
EP1778669A2 (en)	2004-08-18	2007-05-02	Takeda San Diego, Inc.	Kinase inhibitors
CA2591413A1 (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
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
US7538113B2 (en)	2005-02-18	2009-05-26	Wyeth	4-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
US7393667B2 (en)	2005-05-31	2008-07-01	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
EP1910385B1 (en)	2005-08-04	2013-07-24	Sirtris Pharmaceuticals, Inc.	Benzothiazoles and thiazolopyridines as sirtuin modulators
US8093401B2 (en)	2005-08-04	2012-01-10	Sirtris Pharmaceuticals, Inc.	Sirtuin modulating compounds
US8088928B2 (en)	2005-08-04	2012-01-03	Sirtris Pharmaceuticals, Inc.	Sirtuin modulating compounds
JP2009506123A (ja) *	2005-08-29	2009-02-12	バーテックスファーマシューティカルズインコーポレイテッド	非受容体型チロシンキナーゼのｔｅｃファミリーの阻害剤として有用な３，５−二置換ピリド−２−オン
EP1919905B1 (en) *	2005-08-29	2011-02-23	Vertex Pharmaceuticals Incorporated	3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-recptor tyrosine kinases
WO2007027594A1 (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
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
WO2008025526A1 (en) *	2006-08-31	2008-03-06	F. Hoffmann-La Roche Ag	Indole derivatives, their manufacture and use as pharmaceutical agents
EP2145021A2 (en)	2007-05-17	2010-01-20	Bristol-Myers Squibb Company	Biomarkers and methods for determining sensitivity to insulin growth factor-1 receptor modulators
TW200916472A (en)	2007-06-20	2009-04-16	Sirtris Pharmaceuticals Inc	Sirtuin modulating compounds
EP2170859A1 (en) *	2007-06-25	2010-04-07	F. Hoffmann-Roche AG	Benzimidazole amido derivatives as kinase inhibitors
EP2065380A1 (en) *	2007-08-22	2009-06-03	F.Hoffmann-La Roche Ag	Pyridoneamide derivatives as focal adhesion kinase (FAK) inhibitors and their use for the treatment of cancer
US7816540B2 (en) *	2007-12-21	2010-10-19	Hoffmann-La Roche Inc.	Carboxyl- or hydroxyl-substituted benzimidazole derivatives
DK2294065T3 (da) *	2008-01-22	2014-04-28	Vernalis R&D Ltd	Indolyl-pyridonderivater med checkpoint kinase 1 inhibitorisk aktivitet
EP2283020B8 (en)	2008-05-19	2012-12-12	OSI Pharmaceuticals, LLC	Substituted imidazopyr-and imidazotri-azines
EP2376502B1 (en)	2008-12-19	2015-06-17	GlaxoSmithKline LLC	Thiazolopyridine sirtuin modulating compounds
DE102010001064A1 (de) *	2009-03-18	2010-09-23	Bayer Schering Pharma Aktiengesellschaft	Substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung
WO2010123792A1 (en)	2009-04-20	2010-10-28	Osi Pharmaceuticals, Inc.	Preparation of c-pyrazine-methylamines
US8536180B2 (en) *	2009-05-27	2013-09-17	Abbvie Inc.	Pyrimidine inhibitors of kinase activity
EP2494070A2 (en)	2009-10-30	2012-09-05	Bristol-Myers Squibb Company	Methods for treating cancer in patients having igf-1r inhibitor resistance
JP5719028B2 (ja) *	2010-10-06	2015-05-13	グラクソスミスクラインエルエルシー	Ｐｉ３キナーゼ阻害剤としてのベンズイミダゾール誘導体
JP5789888B2 (ja) *	2010-11-01	2015-10-07	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	ロイコトリエン生成のベンゾイミダゾールインヒビター
WO2013056069A1 (en)	2011-10-13	2013-04-18	Bristol-Myers Squibb Company	Methods for selecting and treating cancer in patients with igf-1r/ir inhibitors
CA2915838C (en)	2013-06-21	2023-04-18	Zenith Epigenetics Corp.	Bicyclic bromodomain inhibitors
EP3010918B1 (en)	2013-06-21	2018-08-15	Zenith Epigenetics Ltd.	Novel substituted bicyclic compounds as bromodomain inhibitors
JP6542212B2 (ja)	2013-07-31	2019-07-10	ゼニス・エピジェネティクス・リミテッドＺｅｎｉｔｈＥｐｉｇｅｎｅｔｉｃｓＬｔｄ．	ブロモドメイン阻害剤としての新規キナゾリノン
CN103936719A (zh) *	2014-05-14	2014-07-23	中国药科大学	苯并咪唑类衍生物制备方法及用途
US11920164B2 (en)	2014-07-30	2024-03-05	Yeda Research And Development Co. Ltd.	Media for culturing naive human pluripotent stem cells
EP3227281A4 (en)	2014-12-01	2018-05-30	Zenith Epigenetics Ltd.	Substituted pyridinones as bromodomain inhibitors
EP3230277B1 (en)	2014-12-11	2019-09-18	Zenith Epigenetics Ltd.	Substituted heterocycles as bromodomain inhibitors
HK1245247A1 (zh)	2014-12-17	2018-08-24	恒翼生物医药科技(上海)有限公司	溴结构域的抑制剂
CN107531697A (zh) *	2015-04-16	2018-01-02	默克专利股份公司	3‑(1h‑苯并咪唑‑2‑基)‑1h‑吡啶‑2‑酮衍生物
WO2020152686A1 (en)	2019-01-23	2020-07-30	Yeda Research And Development Co. Ltd.	Culture media for pluripotent stem cells
CN117069696B (zh) *	2023-08-17	2024-04-26	中国药科大学	一种双靶点小分子抑制剂及其制备方法和应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6162804A (en) *	1997-09-26	2000-12-19	Merck & Co., Inc.	Tyrosine kinase inhibitors
SI1194425T1 (sl) *	1999-06-23	2005-12-31	Sanofi Aventis Deutschland	Substituirani benzimidazoli
US7081454B2 (en) *	2001-03-28	2006-07-25	Bristol-Myers Squibb Co.	Tyrosine kinase inhibitors

2002
- 2002-03-26 CN CNA028105168A patent/CN1514833A/zh active Pending
- 2002-03-26 IL IL15804102A patent/IL158041A0/xx unknown
- 2002-03-26 CA CA002442428A patent/CA2442428A1/en not_active Abandoned
- 2002-03-26 GE GE5363A patent/GEP20053660B/en unknown
- 2002-03-26 HR HR20030844A patent/HRP20030844A2/hr not_active Application Discontinuation
- 2002-03-26 RU RU2003131693/04A patent/RU2003131693A/ru not_active Application Discontinuation
- 2002-03-26 KR KR10-2003-7012594A patent/KR20030083016A/ko not_active Withdrawn
- 2002-03-26 EE EEP200300475A patent/EE200300475A/xx unknown
- 2002-03-26 SK SK12002003A patent/SK12002003A3/sk not_active Application Discontinuation
- 2002-03-26 MX MXPA03008690A patent/MXPA03008690A/es unknown
- 2002-03-26 CZ CZ20032615A patent/CZ20032615A3/cs unknown
- 2002-03-26 BR BR0208373-6A patent/BR0208373A/pt not_active IP Right Cessation
- 2002-03-26 JP JP2002577817A patent/JP2004534010A/ja not_active Withdrawn
- 2002-03-26 EP EP02723631A patent/EP1381598A4/en not_active Withdrawn
- 2002-03-26 WO PCT/US2002/009402 patent/WO2002079192A1/en not_active Ceased
- 2002-03-26 PL PL02373300A patent/PL373300A1/pl not_active Application Discontinuation
- 2002-03-26 YU YU84603A patent/YU84603A/sh unknown
- 2002-03-26 HU HU0400323A patent/HUP0400323A2/hu unknown
- 2002-03-27 PE PE2002000244A patent/PE20021015A1/es not_active Application Discontinuation
- 2002-03-27 AR ARP020101167A patent/AR035804A1/es not_active Application Discontinuation
- 2002-03-27 UY UY27234A patent/UY27234A1/es not_active Application Discontinuation
2003
- 2003-09-25 ZA ZA200307466A patent/ZA200307466B/en unknown
- 2003-09-26 IS IS6968A patent/IS6968A/is unknown
- 2003-09-26 NO NO20034308A patent/NO20034308L/no not_active Application Discontinuation
- 2003-09-26 BG BG108206A patent/BG108206A/bg unknown

Also Published As

Publication number	Publication date
BR0208373A (pt)	2005-02-22
GEP20053660B (en)	2005-11-10
ZA200307466B (en)	2005-01-13
HUP0400323A2 (hu)	2005-11-28
CN1514833A (zh)	2004-07-21
PL373300A1 (pl)	2005-08-22
MXPA03008690A (es)	2003-12-12
RU2003131693A (ru)	2005-05-10
PE20021015A1 (es)	2002-11-10
EP1381598A4 (en)	2008-03-19
IS6968A (is)	2003-09-26
YU84603A (sh)	2006-03-03
CZ20032615A3 (en)	2004-03-17
CA2442428A1 (en)	2002-10-10
EP1381598A1 (en)	2004-01-21
HRP20030844A2 (en)	2005-08-31
UY27234A1 (es)	2002-10-31
NO20034308D0 (no)	2003-09-26
JP2004534010A (ja)	2004-11-11
SK12002003A3 (en)	2004-10-05
KR20030083016A (ko)	2003-10-23
EE200300475A (et)	2004-02-16
WO2002079192A1 (en)	2002-10-10
AR035804A1 (es)	2004-07-14
NO20034308L (no)	2003-11-26
IL158041A0 (en)	2004-03-28

Publication	Publication Date	Title
BG108206A (bg)	2004-11-30	Нови инхибитори на тирозинкиназа
US20040044203A1 (en)	2004-03-04	Novel tyrosine kinase inhibitors
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CN106661035B (zh)	2019-11-19	用作布鲁顿氏酪氨酸激酶的抑制剂的吡唑并嘧啶衍生物
US7244735B2 (en)	2007-07-17	Heterocyclic protein kinase inhibitors and uses thereof
US7232826B2 (en)	2007-06-19	Tyrosine kinase inhibitors
CA2994917A1 (en)	2017-02-16	3-indol substituted derivatives, pharmaceutical compositions and methods for use
US7655652B2 (en)	2010-02-02	Imidazolo-5-yl-2-anilinopyrimidines as agents for the inhibition of cell proliferation
AU2004212421A1 (en)	2004-08-26	Heteroaryl substituted pyrolls useful as inhibitors of protein kinases
MXPA04008807A (es)	2004-11-26	Derivados de 4-(imidazol-5-il)-2-(4-sulfonilanilino)pirimidina con actividad inhibidora de cdk.
EP2305651A1 (en)	2011-04-06	2,3,6-trisubstituted-4-pyrimidone derivatives
WO2016041618A1 (en)	2016-03-24	Substituted indazoles and related heterocycles
WO2024028169A1 (en)	2024-02-08	Novel specifically substituted thiophenolic compounds
KR20250151616A (ko)	2025-10-21	아미노피리미딘 유도체 및 이의 아릴 탄화수소 수용체 조절제로서의 용도
AU2016363719B2 (en)	2019-11-14	1,3,4-thiadiazole compounds and their use in treating cancer
JP2000169475A (ja)	2000-06-20	ピラゾ―ル誘導体およびその塩
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AU2002254399A1 (en)	2002-10-15	Novel tyrosine kinase inhibitors
HK1228287A1 (en)	2017-11-03	Quinazoline derivatives as tam family kinase inhibitors