JP2009515995A5 - - Google Patents
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- Publication number
- JP2009515995A5 JP2009515995A5 JP2008541376A JP2008541376A JP2009515995A5 JP 2009515995 A5 JP2009515995 A5 JP 2009515995A5 JP 2008541376 A JP2008541376 A JP 2008541376A JP 2008541376 A JP2008541376 A JP 2008541376A JP 2009515995 A5 JP2009515995 A5 JP 2009515995A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- carbonyl
- amino
- triazin
- pyrrolo
- 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.)
- Granted
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- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims 12
- 125000004104 aryloxy group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000003107 substituted aryl group Chemical group 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 239000002254 cytotoxic agent Substances 0.000 claims 5
- 229940127089 cytotoxic agent Drugs 0.000 claims 5
- 231100000599 cytotoxic agent Toxicity 0.000 claims 5
- 229940127084 other anti-cancer agent Drugs 0.000 claims 5
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 230000002062 proliferating effect Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 150000001602 bicycloalkyls Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 108091008598 receptor tyrosine kinases Proteins 0.000 claims 2
- 102000027426 receptor tyrosine kinases Human genes 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- WRQIIHFURAGCIR-UHFFFAOYSA-N 1-[3-(4-amino-7-bromopyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(2,4-dichlorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(Br)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C=C1Cl WRQIIHFURAGCIR-UHFFFAOYSA-N 0.000 claims 1
- XTLOABAAKWDWKF-UHFFFAOYSA-N 1-[3-(4-amino-7-bromopyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(5-cyclopropyl-2-methylpyrazol-3-yl)urea Chemical compound C1=C(NC(=O)NC=2C=C(C=CC=2)C(=O)C2=C3C(N)=NC=NN3C(Br)=C2)N(C)N=C1C1CC1 XTLOABAAKWDWKF-UHFFFAOYSA-N 0.000 claims 1
- JSLIJLUSLPYLEM-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(2,4-dichlorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C=C1Cl JSLIJLUSLPYLEM-UHFFFAOYSA-N 0.000 claims 1
- DSEJPAOKMPFSDR-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(2,4-dimethylphenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C=C1C DSEJPAOKMPFSDR-UHFFFAOYSA-N 0.000 claims 1
- VPMQPJSTRSFLBC-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C2=C3C(N)=NC=NN3C(C(C)C)=C2)=C1 VPMQPJSTRSFLBC-UHFFFAOYSA-N 0.000 claims 1
- KSVJBSVMTUNSBX-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(2-phenylphenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 KSVJBSVMTUNSBX-UHFFFAOYSA-N 0.000 claims 1
- QZIROKOVAVXJCK-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C(=O)C2=C3C(N)=NC=NN3C(C(C)C)=C2)=C1 QZIROKOVAVXJCK-UHFFFAOYSA-N 0.000 claims 1
- FOFRCQWXOKHOIE-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(3-methylphenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(C)=C1 FOFRCQWXOKHOIE-UHFFFAOYSA-N 0.000 claims 1
- CZMBZBLFVFIDHB-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(4-bromophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Br)C=C1 CZMBZBLFVFIDHB-UHFFFAOYSA-N 0.000 claims 1
- GQLXAGSDBDRKKH-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(4-fluorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(F)C=C1 GQLXAGSDBDRKKH-UHFFFAOYSA-N 0.000 claims 1
- KDQFJIOVEHPENA-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(4-phenoxyphenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 KDQFJIOVEHPENA-UHFFFAOYSA-N 0.000 claims 1
- KKVKEHQMNCTHOL-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(4-phenylmethoxyphenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 KKVKEHQMNCTHOL-UHFFFAOYSA-N 0.000 claims 1
- BZEWXXDOPRVKCS-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(5-cyclopropyl-2-methylpyrazol-3-yl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC(N(N=1)C)=CC=1C1CC1 BZEWXXDOPRVKCS-UHFFFAOYSA-N 0.000 claims 1
- DIGSKJLFEXFWAC-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-(5-tert-butyl-2-methylpyrazol-3-yl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C DIGSKJLFEXFWAC-UHFFFAOYSA-N 0.000 claims 1
- ADYFANLDRLLPSL-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1C(F)(F)F ADYFANLDRLLPSL-UHFFFAOYSA-N 0.000 claims 1
- JVXQFWTWKPFZOB-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(N(C)C)C=C1 JVXQFWTWKPFZOB-UHFFFAOYSA-N 0.000 claims 1
- XPCDUPMKQGWWSS-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 XPCDUPMKQGWWSS-UHFFFAOYSA-N 0.000 claims 1
- SMZVSSCASPEMIK-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-[5-cyclopropyl-2-(2-morpholin-4-ylethyl)pyrazol-3-yl]urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(C2CC2)=NN1CCN1CCOCC1 SMZVSSCASPEMIK-UHFFFAOYSA-N 0.000 claims 1
- MVRBPFWJIWRIQL-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-[5-tert-butyl-2-(2-hydroxyethyl)pyrazol-3-yl]urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1CCO MVRBPFWJIWRIQL-UHFFFAOYSA-N 0.000 claims 1
- DYZUVHQBGUMLKY-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-naphthalen-1-ylurea Chemical compound NC1=NC=NN2C(C(C)C)=CC(C(=O)C=3C=C(NC(=O)NC=4C5=CC=CC=C5C=CC=4)C=CC=3)=C21 DYZUVHQBGUMLKY-UHFFFAOYSA-N 0.000 claims 1
- DFQXDYVZCOUQOI-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-naphthalen-2-ylurea Chemical compound NC1=NC=NN2C(C(C)C)=CC(C(=O)C=3C=C(NC(=O)NC=4C=C5C=CC=CC5=CC=4)C=CC=3)=C21 DFQXDYVZCOUQOI-UHFFFAOYSA-N 0.000 claims 1
- YASCKFXNGQOGHI-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-phenylurea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1 YASCKFXNGQOGHI-UHFFFAOYSA-N 0.000 claims 1
- QWFUHFFGAOBQJP-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)phenyl]-3-pyridin-3-ylurea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CN=C1 QWFUHFFGAOBQJP-UHFFFAOYSA-N 0.000 claims 1
- ZJDBIGLNRMGKMD-UHFFFAOYSA-N 1-[3-[4-amino-7-[3-(dimethylamino)prop-1-ynyl]pyrrolo[2,1-f][1,2,4]triazine-5-carbonyl]phenyl]-3-(5-cyclopropyl-2-methylpyrazol-3-yl)urea Chemical compound C=12C(N)=NC=NN2C(C#CCN(C)C)=CC=1C(=O)C(C=1)=CC=CC=1NC(=O)NC(N(N=1)C)=CC=1C1CC1 ZJDBIGLNRMGKMD-UHFFFAOYSA-N 0.000 claims 1
- ZAUDXAUEKJIQSN-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-(2,4-dichlorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=C(Cl)C=C1Cl ZAUDXAUEKJIQSN-UHFFFAOYSA-N 0.000 claims 1
- HQQXLNNMPJFQTN-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-(2,4-difluorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=C(F)C=C1F HQQXLNNMPJFQTN-UHFFFAOYSA-N 0.000 claims 1
- UMKGTOFMRRZZJG-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-(2-cyanophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=CC=C1C#N UMKGTOFMRRZZJG-UHFFFAOYSA-N 0.000 claims 1
- SJQRRVUSTOILCH-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-(2-fluorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=CC=C1F SJQRRVUSTOILCH-UHFFFAOYSA-N 0.000 claims 1
- XLUCVCLBQLSBSS-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-(2-methyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound CN1N=C(C(C)C)C=C1NC(=O)NC1=CN=CC(C(=O)C2=C3C(N)=NC=NN3C(C(C)C)=C2)=C1 XLUCVCLBQLSBSS-UHFFFAOYSA-N 0.000 claims 1
- NJLDTRRPLUMIPI-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-(4-chlorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=C(Cl)C=C1 NJLDTRRPLUMIPI-UHFFFAOYSA-N 0.000 claims 1
- XSHPLAKMCBWMPR-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=CC=C1C(F)(F)F XSHPLAKMCBWMPR-UHFFFAOYSA-N 0.000 claims 1
- IAPIEYZPBDFEHD-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazine-5-carbonyl)pyridin-3-yl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C=12C(N)=NC=NN2C(C(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=C(N(C)C)C=C1 IAPIEYZPBDFEHD-UHFFFAOYSA-N 0.000 claims 1
- ZKXXMWLEMLPDGZ-UHFFFAOYSA-N 1-[5-[4-amino-7-[3-(dimethylamino)prop-1-ynyl]pyrrolo[2,1-f][1,2,4]triazine-5-carbonyl]pyridin-3-yl]-3-(2,4-dichlorophenyl)urea Chemical compound C=12C(N)=NC=NN2C(C#CCN(C)C)=CC=1C(=O)C(C=1)=CN=CC=1NC(=O)NC1=CC=C(Cl)C=C1Cl ZKXXMWLEMLPDGZ-UHFFFAOYSA-N 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000000172 Medulloblastoma Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 101150111783 NTRK1 gene Proteins 0.000 claims 1
- 101150117329 NTRK3 gene Proteins 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 101150056950 Ntrk2 gene Proteins 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 201000010989 colorectal carcinoma Diseases 0.000 claims 1
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims 1
- 210000004907 gland Anatomy 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000005296 lung carcinoma Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73826905P | 2005-11-18 | 2005-11-18 | |
| US60/738,269 | 2005-11-18 | ||
| US11/560,378 | 2006-11-16 | ||
| US11/560,378 US7514435B2 (en) | 2005-11-18 | 2006-11-16 | Pyrrolotriazine kinase inhibitors |
| PCT/US2006/044756 WO2007061882A2 (en) | 2005-11-18 | 2006-11-17 | Pyrrolotriazine kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009515995A JP2009515995A (ja) | 2009-04-16 |
| JP2009515995A5 true JP2009515995A5 (https=) | 2009-11-26 |
| JP5095626B2 JP5095626B2 (ja) | 2012-12-12 |
Family
ID=38051768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008541376A Expired - Fee Related JP5095626B2 (ja) | 2005-11-18 | 2006-11-17 | ピロロトリアジンキナーゼ阻害剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7514435B2 (https=) |
| EP (1) | EP1948664B1 (https=) |
| JP (1) | JP5095626B2 (https=) |
| KR (1) | KR101392678B1 (https=) |
| CN (1) | CN101365701B (https=) |
| AT (1) | ATE512151T1 (https=) |
| AU (1) | AU2006318682B2 (https=) |
| NO (1) | NO20082023L (https=) |
| WO (1) | WO2007061882A2 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY28931A1 (es) | 2004-06-03 | 2005-12-30 | Bayer Pharmaceuticals Corp | Derivados de pirrolotriazina utiles para tratar trastornos hiper-proliferativos y enfermedades asociadas con angiogenesis |
| WO2007064931A2 (en) | 2005-12-02 | 2007-06-07 | Bayer Healthcare Llc | Substituted 4-amino-pyrrolotriazine derivatives useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
| PE20070855A1 (es) * | 2005-12-02 | 2007-10-14 | Bayer Pharmaceuticals Corp | Derivados de 4-amino-pirrolotriazina sustituida como inhibidores de quinasas |
| US8124759B2 (en) * | 2007-05-09 | 2012-02-28 | Abbott Laboratories | Inhibitors of protein kinases |
| WO2009003590A1 (en) * | 2007-07-03 | 2009-01-08 | Sanofi-Aventis | A process for the palladium-catalyzed coupling of terminal alkynes with heteroaryl tosylates and heteroaryl benzenesulfonates |
| CA2700489A1 (en) | 2007-09-25 | 2009-04-02 | Bayer Healthcare Llc | Pyrrolotriazine derivatives useful for treating cancer through inhibition of aurora kinase |
| EP2206707B1 (en) | 2007-10-24 | 2014-07-23 | Astellas Pharma Inc. | Azolecarboxamide compound or salt thereof |
| CN102245610B (zh) * | 2008-10-08 | 2014-04-30 | 百时美施贵宝公司 | 吡咯并三嗪激酶抑制剂 |
| ES2539620T3 (es) | 2008-12-19 | 2015-07-02 | Cephalon, Inc. | Pirrolotriazina como inhibidor de ALK y de JAK2 |
| US8765754B2 (en) * | 2009-04-29 | 2014-07-01 | Locus Pharmaceuticals, Inc. | Pyrrolotriazine compounds |
| WO2011123493A1 (en) * | 2010-03-31 | 2011-10-06 | Bristol-Myers Squibb Company | Substituted pyrrolotriazines as protein kinase inhibitors |
| CA2835835C (en) | 2011-05-13 | 2019-04-02 | Array Biopharma Inc. | Pyrrolidinyl urea and pyrrolidinyl thiourea compounds as trka kinase inhibitors |
| SG195100A1 (en) | 2011-07-01 | 2013-12-30 | Bayer Ip Gmbh | Hydroxymethylaryl-substituted pyrrolotriazines as alk1 inhibitors |
| UY34484A (es) | 2011-12-15 | 2013-07-31 | Bayer Ip Gmbh | Benzotienilo-pirrolotriazinas disustituidas y sus usos |
| CN104159900B (zh) | 2011-12-15 | 2016-08-24 | 拜耳知识产权有限责任公司 | 取代的苯并噻吩基-吡咯并三嗪及其在癌症治疗中的用途 |
| JP6082033B2 (ja) | 2012-02-23 | 2017-02-15 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換ベンゾチエニル−ピロロトリアジンおよびその使用 |
| CN103450204B (zh) | 2012-05-31 | 2016-08-17 | 中国科学院上海药物研究所 | 吡咯[2，1-f][1，2，4]并三嗪类化合物，其制备方法及用途 |
| US9724352B2 (en) | 2012-05-31 | 2017-08-08 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Pyrrolo[2,1-F[1,2,4]triazine compounds, preparation methods and applications thereof |
| JP2015531395A (ja) | 2012-10-04 | 2015-11-02 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | ピロロ［３，２−ｃ］ピリジントロポミオシン関連キナーゼ阻害剤 |
| US9981959B2 (en) | 2012-11-13 | 2018-05-29 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078372A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078325A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078331A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9822118B2 (en) | 2012-11-13 | 2017-11-21 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078417A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078328A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-bicyclic aryl,n'-pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| MX374242B (es) | 2012-11-13 | 2025-03-05 | Array Biopharma Inc | Compuestos de n-pirrolidinil, n' -pirazolil-urea, tiourea, guanidina y cianoguanidina como inhibidores de trka cinasa. |
| RS55593B1 (sr) | 2012-11-13 | 2017-06-30 | Array Biopharma Inc | Jedinjenja biciklične uree, tiouree, guanidina i cijanoguanidina korisna za lečenje bola |
| WO2014078378A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| EP3054955B1 (en) | 2013-10-11 | 2018-05-30 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| MA40434B1 (fr) | 2014-05-15 | 2019-09-30 | Array Biopharma Inc | 1-((3s,4r)-4-(3-fluorophényl)-1-(2-méthoxyéthyl)pyrrolidin-3-yl)-3-(4-méthyl-3-(2-méthylpyrimidin-5-yl)-1-phényl-1h-pyrazol-5-yl)urée comme inhibiteur de la kinase trka |
| CN104151276A (zh) * | 2014-06-30 | 2014-11-19 | 北京万全德众医药生物技术有限公司 | 一种盐酸决奈达隆代谢杂质的制备方法 |
| EP3209665B1 (en) | 2014-10-22 | 2019-08-14 | Bristol-Myers Squibb Company | Substituted pyrrolotriazine amine compounds as pi3k inhibitors |
| ES2807785T3 (es) | 2014-10-22 | 2021-02-24 | Bristol Myers Squibb Co | Compuestos de heteroarilamina bicíclicos como inhibidores de pi3k |
| KR102483020B1 (ko) | 2016-03-28 | 2023-01-04 | 인사이트 코포레이션 | Tam 저해제로서의 피롤로트리아진 화합물 |
| CN112225723B (zh) * | 2020-12-16 | 2021-03-30 | 北京华氏开元医药科技有限公司 | 一种吲哚类衍生物、制备方法及应用 |
| JP7840066B2 (ja) | 2021-05-03 | 2026-04-03 | ジェービーケーラボ カンパニー リミテッド | ２，６－ジクロロ－４－（４－（４－ヒドロキシシクロヘキシルアミノ）－７ｈ－ピロロ［２，３－ｄ］ピリミジン－５－イル）フェノールを活性成分として含有する、がんを予防、緩和、または処置するための医薬組成物 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3621706B2 (ja) | 1996-08-28 | 2005-02-16 | ファイザー・インク | 置換された６，５―ヘテロ―二環式誘導体 |
| JP4649046B2 (ja) * | 1999-05-21 | 2011-03-09 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼのピロロトリアジン阻害剤 |
| US6787545B1 (en) * | 1999-08-23 | 2004-09-07 | Shiongi & Co., Ltd. | Pyrrolotriazine derivatives having spla2-inhibitory activities |
| US6670357B2 (en) * | 2000-11-17 | 2003-12-30 | Bristol-Myers Squibb Company | Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors |
| US6867300B2 (en) * | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| GEP20063915B (en) | 2000-11-17 | 2006-09-11 | Bristol Myers Squibb Co | PYRROLOTRIAZINE COMPOUNDS USEFUL AS KINASE INHIBITORS AND USE THEREOF FOR TREATING p38 KINASE-ASSOCIATED CONDITIONS |
| EP1430053B1 (en) | 2001-09-27 | 2006-10-25 | SmithKline Beecham Corporation | AZAOXOINDOLE DERIVATIVES AS Trk PROTEIN KINASE INHIBITORS FOR THE TREATMENT OF CANCER AND CHRONIC PAIN |
| TW200300350A (en) * | 2001-11-14 | 2003-06-01 | Bristol Myers Squibb Co | C-5 modified indazolylpyrrolotriazines |
| TW200306841A (en) * | 2002-04-23 | 2003-12-01 | Bristol Myers Squibb Co | Aryl ketone pyrrolo-triazine compounds useful as kinase inhibitors |
| TW200407143A (en) * | 2002-05-21 | 2004-05-16 | Bristol Myers Squibb Co | Pyrrolotriazinone compounds and their use to treat diseases |
| TWI329112B (en) * | 2002-07-19 | 2010-08-21 | Bristol Myers Squibb Co | Novel inhibitors of kinases |
| TWI272271B (en) * | 2002-07-19 | 2007-02-01 | Bristol Myers Squibb Co | Process for preparing certain pyrrolotriazine compounds |
| AU2003265349A1 (en) * | 2002-08-02 | 2004-02-23 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| TW200420565A (en) * | 2002-12-13 | 2004-10-16 | Bristol Myers Squibb Co | C-6 modified indazolylpyrrolotriazines |
| MY141220A (en) | 2003-11-17 | 2010-03-31 | Astrazeneca Ab | Pyrazole derivatives as inhibitors of receptor tyrosine kinases |
| US7102001B2 (en) * | 2003-12-12 | 2006-09-05 | Bristol-Myers Squibb Company | Process for preparing pyrrolotriazine |
| US7064203B2 (en) * | 2003-12-29 | 2006-06-20 | Bristol Myers Squibb Company | Di-substituted pyrrolotriazine compounds |
| UY28931A1 (es) * | 2004-06-03 | 2005-12-30 | Bayer Pharmaceuticals Corp | Derivados de pirrolotriazina utiles para tratar trastornos hiper-proliferativos y enfermedades asociadas con angiogenesis |
| US7102002B2 (en) * | 2004-06-16 | 2006-09-05 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7102003B2 (en) * | 2004-07-01 | 2006-09-05 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds |
| US7151176B2 (en) * | 2004-10-21 | 2006-12-19 | Bristol-Myers Squibb Company | Pyrrolotriazine compounds |
| JP5116687B2 (ja) | 2005-11-02 | 2013-01-09 | バイエル・ファルマ・アクチェンゲゼルシャフト | がんおよび他の過剰増殖性疾患の処置のためのピロロ［２，１−ｆ］［１，２，４］トリアジン−４−イルアミンＩＧＦ−１Ｒキナーゼ阻害剤 |
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- 2006-11-17 AT AT06837967T patent/ATE512151T1/de not_active IP Right Cessation
- 2006-11-17 EP EP06837967A patent/EP1948664B1/en active Active
- 2006-11-17 WO PCT/US2006/044756 patent/WO2007061882A2/en not_active Ceased
- 2006-11-17 JP JP2008541376A patent/JP5095626B2/ja not_active Expired - Fee Related
- 2006-11-17 CN CN2006800513398A patent/CN101365701B/zh not_active Expired - Fee Related
- 2006-11-17 AU AU2006318682A patent/AU2006318682B2/en not_active Ceased
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2008
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- 2008-06-17 KR KR1020087014666A patent/KR101392678B1/ko not_active Expired - Fee Related
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